#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102175.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_2102175
loop_
_publ_author_name
'Madhavi, N. N. L.'
'Desiraju, Gautam R.'
'Bilton, Claire'
'Howard, Judith A. K.'
'Allen, Frank H.'
_publ_section_title
;Crystal engineering in the gem-alkynol family: interplay between
 strong and weak interactions in structures of
 2,3,5,6-tetrahalo[F,Cl,Br]-trans-1,4-diethynylcyclohexa-2,5-diene-1,4-diols
;
_journal_coeditor_code           BM0033
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1063
_journal_page_last               1070
_journal_paper_doi               10.1107/S0108768100011496
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C10 H4 F4 O2'
_chemical_formula_sum            'C10 H4 F4 O2'
_chemical_formula_weight         232.13
_chemical_melting_point          132.5(5)
_chemical_name_systematic
' 2,3,5,6-tetrafluoro-trans-1,4-diethynyl-cyclohexa-2,5-diene-1,4-diol'
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.73(3)
_cell_angle_beta                 98.73(3)
_cell_angle_gamma                114.46(3)
_cell_formula_units_Z            3
_cell_length_a                   8.9002(18)
_cell_length_b                   9.2388(18)
_cell_length_c                   9.6721(19)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      0.16
_cell_volume                     708.3(3)
_computing_cell_refinement       'Bruker SMART (Bruker Systems Inc., 1999a)'
_computing_data_collection       'Bruker SMART (Bruker Systems Inc., 1999a)'
_computing_data_reduction        'Bruker SAINT (Bruker Systems Inc., 1999b)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 'not relevant'
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            8674
_diffrn_reflns_theta_full        29.88
_diffrn_reflns_theta_max         29.88
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.382
_exptl_absorpt_correction_T_min  0.289
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(XPREP in SHELX97; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.080(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0336
_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)+(0.0484P)²+0.2454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                3376
_reflns_number_total             3722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0033.cif
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '132-133' was changed to '132.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '132-133' was changed to '132.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        708.3(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2102175
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
F1 F 0.13140(9) 0.32812(9) 0.85824(8) 0.02992(17) Uani 1 1 d
F2 F 0.10278(9) 0.82232(8) 0.99013(8) 0.02855(17) Uani 1 1 d
F21 F -0.45397(9) -0.00542(9) 0.78559(7) 0.02882(17) Uani 1 1 d
F11 F 0.54677(9) 0.58373(9) 1.23827(7) 0.03106(18) Uani 1 1 d
O21 O -0.70633(11) -0.25896(9) 0.57778(9) 0.02384(17) Uani 1 1 d
F22 F -0.18494(8) 0.15228(9) 0.66778(7) 0.02902(17) Uani 1 1 d
O11 O 0.24851(10) 0.53620(9) 1.34412(8) 0.02313(17) Uani 1 1 d
F12 F 0.18252(8) 0.32907(9) 1.54950(8) 0.03013(17) Uani 1 1 d
O1 O 0.09274(10) 0.60128(10) 0.76376(8) 0.02489(18) Uani 1 1 d
C24 C -0.47257(14) -0.00009(12) 0.64633(10) 0.0204(2) Uani 1 1 d
C3 C 0.13028(13) 0.58530(12) 0.91000(10) 0.0196(2) Uani 1 1 d
C5 C 0.05022(13) 0.66421(12) 0.99688(11) 0.0204(2) Uani 1 1 d
C13 C 0.34702(13) 0.44886(12) 1.37978(11) 0.0197(2) Uani 1 1 d
C23 C -0.65179(13) -0.09123(12) 0.56684(11) 0.0197(2) Uani 1 1 d
C12 C 0.27270(14) 0.29858(13) 1.27786(12) 0.0235(2) Uani 1 1 d
C25 C -0.34131(13) 0.07603(12) 0.58808(11) 0.0205(2) Uani 1 1 d
C14 C 0.52767(13) 0.54587(13) 1.36766(11) 0.0212(2) Uani 1 1 d
C15 C 0.34023(13) 0.40981(12) 1.52821(11) 0.0207(2) Uani 1 1 d
C4 C 0.06470(13) 0.40977(13) 0.92853(11) 0.0205(2) Uani 1 1 d
C22 C -0.76156(14) -0.02754(13) 0.62251(12) 0.0246(2) Uani 1 1 d
C1 C 0.46278(16) 0.73049(19) 0.99717(14) 0.0373(3) Uani 1 1 d
C2 C 0.31531(14) 0.66562(14) 0.95594(11) 0.0248(2) Uani 1 1 d
C21 C -0.85068(17) 0.02473(16) 0.66346(15) 0.0344(3) Uani 1 1 d
C11 C 0.21624(16) 0.17711(15) 1.19891(14) 0.0305(2) Uani 1 1 d
H11A H 0.264(2) 0.601(2) 1.417(2) 0.041(5) Uiso 1 1 d
H11 H 0.175(2) 0.081(2) 1.137(2) 0.046(5) Uiso 1 1 d
H21A H -0.758(3) -0.281(2) 0.642(2) 0.050(5) Uiso 1 1 d
H21 H -0.924(3) 0.069(2) 0.692(2) 0.053(5) Uiso 1 1 d
H1A H -0.018(3) 0.560(2) 0.735(2) 0.051(5) Uiso 1 1 d
H1 H 0.582(3) 0.786(3) 1.037(2) 0.067(6) Uiso 1 1 d
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 F1 F22 90.58(6) . .
C5 F2 F1 59.41(6) . 2_567
C14 F11 F1 122.52(7) . 2_667
C23 O21 H21A 109.3(14) . .
C25 F22 F1 173.72(7) . .
C13 O11 H11A 107.3(12) . .
C15 F12 F11 58.65(6) . 2_668
C15 F12 F1 71.00(7) . 1_554
F11 F12 F1 128.58(3) 2_668 1_554
C3 O1 H1A 109.4(13) . .
C25 C24 F21 121.05(10) . .
C25 C24 C23 125.09(9) . .
F21 C24 C23 113.84(9) . .
O1 C3 C2 107.20(9) . .
O1 C3 C5 110.26(9) . .
C2 C3 C5 109.96(9) . .
O1 C3 C4 110.33(9) . .
C2 C3 C4 110.07(9) . .
C5 C3 C4 109.02(8) . .
C4 C5 F2 120.64(10) 2_567 .
C4 C5 C3 125.45(10) 2_567 .
F2 C5 C3 113.89(9) . .
O11 C13 C12 107.14(9) . .
O11 C13 C15 109.96(9) . .
C12 C13 C15 110.04(9) . .
O11 C13 C14 110.57(9) . .
C12 C13 C14 109.47(9) . .
C15 C13 C14 109.63(9) . .
O21 C23 C22 111.66(9) . .
O21 C23 C24 108.92(9) . .
C22 C23 C24 110.27(9) . .
O21 C23 C25 106.61(9) . 2_456
C22 C23 C25 109.85(9) . 2_456
C24 C23 C25 109.46(9) . 2_456
C11 C12 C13 178.10(12) . .
C24 C25 F22 120.83(10) . .
C24 C25 C23 125.41(10) . 2_456
F22 C25 C23 113.74(9) . 2_456
C15 C14 F11 120.87(10) 2_668 .
C15 C14 C13 125.11(10) 2_668 .
F11 C14 C13 114.01(9) . .
C14 C15 F12 121.33(10) 2_668 .
C14 C15 C13 125.25(10) 2_668 .
F12 C15 C13 113.36(9) . .
C5 C4 F1 120.41(10) 2_567 .
C5 C4 C3 125.46(10) 2_567 .
F1 C4 C3 114.12(9) . .
C21 C22 C23 178.11(13) . .
C2 C1 H1 176.3(13) . .
C1 C2 C3 177.83(12) . .
C22 C21 H21 177.2(12) . .
C12 C11 H11 178.4(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C4 1.3455(12) .
F1 F22 2.8649(17) .
F2 C5 1.3464(12) .
F2 F1 2.6873(14) 2_567
F21 C24 1.3386(12) .
F11 C14 1.3378(12) .
F11 F1 2.9527(13) 2_667
O21 C23 1.4361(13) .
O21 H21A 0.81(2) .
F22 C25 1.3487(13) .
O11 C13 1.4384(12) .
O11 H11A 0.851(19) .
F12 C15 1.3453(13) .
F12 F11 2.7098(15) 2_668
F12 F1 16.294(3) 1_554
O1 C3 1.4348(12) .
O1 H1A 0.88(2) .
C24 C25 1.3221(15) .
C24 C23 1.5085(16) .
C3 C2 1.4775(16) .
C3 C5 1.5091(15) .
C3 C4 1.5128(15) .
C5 C4 1.3203(16) 2_567
C13 C12 1.4833(16) .
C13 C15 1.5069(14) .
C13 C14 1.5099(15) .
C23 C22 1.4782(15) .
C23 C25 1.5084(14) 2_456
C12 C11 1.1832(18) .
C25 C23 1.5084(14) 2_456
C14 C15 1.3238(16) 2_668
C15 C14 1.3238(16) 2_668
C4 C5 1.3203(15) 2_567
C22 C21 1.1862(18) .
C1 C2 1.1829(18) .
C1 H1 0.97(2) .
C21 H21 0.96(2) .
C11 H11 0.936(19) .
