#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102177.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_2102177
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 Br4 O2'
_chemical_formula_sum            'C10 H4 Br4 O2'
_chemical_formula_weight         475.77
_chemical_melting_point          205.5(5)
_chemical_name_systematic
2,3,5,6-tetrabromo-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
_cell_angle_alpha                85.738(1)
_cell_angle_beta                 69.625(1)
_cell_angle_gamma                72.72(1)
_cell_formula_units_Z            4
_cell_length_a                   8.9147(3)
_cell_length_b                   12.6402(5)
_cell_length_c                   12.6547(5)
_cell_measurement_reflns_used    510
_cell_measurement_temperature    150
_cell_measurement_theta_max      23.72
_cell_measurement_theta_min      5.10
_cell_volume                     1275.75(11)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14367
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    12.599
_exptl_absorpt_correction_T_max  0.0737
_exptl_absorpt_correction_T_min  0.0180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.797
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0218P)²+4.0324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                4966
_reflns_number_total             5818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0033.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '205-206' was changed to '205.5(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 '205-206' was changed to '205.5(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        1275.76(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2102177
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
Br32 Br 0.23387(6) 0.17095(4) 0.93445(4) 0.02955(11) Uani 1 1 d
Br21 Br 0.26974(6) 0.38542(4) 1.13043(4) 0.02820(11) Uani 1 1 d
Br22 Br 0.40392(6) 0.42595(5) 0.85341(4) 0.03255(12) Uani 1 1 d
Br11 Br 0.78564(6) 0.43745(4) 0.62350(4) 0.03124(12) Uani 1 1 d
Br31 Br 0.40744(6) -0.09732(4) 0.86395(4) 0.02761(11) Uani 1 1 d
Br1 Br 0.79084(7) -0.18445(4) 0.59429(4) 0.03404(12) Uani 1 1 d
Br2 Br 0.84216(7) -0.08758(5) 0.33470(4) 0.03575(13) Uani 1 1 d
Br12 Br 0.48669(6) 0.68322(4) 0.67843(4) 0.02516(10) Uani 1 1 d
O3 O -0.0988(4) 0.3802(3) 1.1712(3) 0.0233(7) Uani 1 1 d
O1 O 1.0803(5) -0.1357(3) 0.6498(3) 0.0273(7) Uani 1 1 d
C34 C 0.1752(5) -0.0377(3) 0.9406(3) 0.0187(8) Uani 1 1 d
C25 C 0.1746(5) 0.4672(3) 0.9417(4) 0.0183(8) Uani 1 1 d
C4 C 0.9092(5) -0.0793(4) 0.5363(4) 0.0218(9) Uani 1 1 d
C13 C 0.6262(5) 0.3856(3) 0.4816(3) 0.0186(8) Uani 1 1 d
C3 C 0.9714(5) -0.0412(3) 0.6199(3) 0.0185(8) Uani 1 1 d
C5 C 0.9306(6) -0.0423(4) 0.4334(4) 0.0215(9) Uani 1 1 d
C35 C 0.1068(5) 0.0694(3) 0.9688(3) 0.0187(8) Uani 1 1 d
C14 C 0.6176(5) 0.4770(4) 0.5572(3) 0.0178(8) Uani 1 1 d
C15 C 0.5043(5) 0.5748(4) 0.5760(3) 0.0183(8) Uani 1 1 d
C23 C -0.0620(5) 0.4806(3) 1.1266(3) 0.0182(8) Uani 1 1 d
C33 C 0.0778(5) -0.1231(3) 0.9671(3) 0.0163(8) Uani 1 1 d
C24 C 0.1214(5) 0.4505(3) 1.0519(3) 0.0187(8) Uani 1 1 d
O4 O 0.0960(4) -0.1677(3) 0.8614(2) 0.0207(6) Uani 1 1 d
O2 O 0.7898(4) 0.3546(3) 0.3984(3) 0.0202(6) Uani 1 1 d
C22 C -0.0946(5) 0.5578(3) 1.2199(4) 0.0201(8) Uani 1 1 d
C2 C 0.8281(6) 0.0123(4) 0.7218(4) 0.0240(9) Uani 1 1 d
C32 C 0.1482(6) -0.2131(4) 1.0344(4) 0.0222(9) Uani 1 1 d
C21 C -0.1280(6) 0.6166(4) 1.2985(4) 0.0268(10) Uani 1 1 d
C12 C 0.5913(6) 0.2906(4) 0.5515(4) 0.0233(9) Uani 1 1 d
C1 C 0.7190(7) 0.0528(5) 0.8056(4) 0.0330(11) Uani 1 1 d
C11 C 0.5609(7) 0.2152(5) 0.6053(5) 0.0385(13) Uani 1 1 d
C31 C 0.2033(8) -0.2869(5) 1.0836(5) 0.0367(13) Uani 1 1 d
H1A H 1.056(8) -0.133(5) 0.708(6) 0.038(19) Uiso 1 1 d
H1 H 0.632(8) 0.085(5) 0.867(6) 0.047(18) Uiso 1 1 d
H4A H 0.094(7) -0.229(5) 0.869(5) 0.030(15) Uiso 1 1 d
H11 H 0.561(8) 0.153(5) 0.633(5) 0.045(18) Uiso 1 1 d
H21 H -0.158(8) 0.673(5) 1.357(5) 0.045(17) Uiso 1 1 d
H4 H 0.240(8) -0.334(5) 1.109(5) 0.040(19) Uiso 1 1 d
H3A H -0.141(8) 0.378(5) 1.225(5) 0.029(17) Uiso 1 1 d
H2A H 0.786(13) 0.306(8) 0.390(8) 0.10(4) 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'
Br Br -0.2901 2.4595 '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
C23 O3 H3A 120(5) . .
C3 O1 H1A 106(5) . .
C35 C34 C33 124.3(4) . .
C35 C34 Br31 121.5(3) . .
C33 C34 Br31 114.2(3) . .
C24 C25 C23 125.0(4) . 2_567
C24 C25 Br22 122.0(3) . .
C23 C25 Br22 112.9(3) 2_567 .
C5 C4 C3 124.5(4) . .
C5 C4 Br1 122.0(3) . .
C3 C4 Br1 113.5(3) . .
O2 C13 C12 111.3(4) . .
O2 C13 C14 107.8(3) . .
C12 C13 C14 109.0(3) . .
O2 C13 C15 109.7(3) . 2_666
C12 C13 C15 108.0(4) . 2_666
C14 C13 C15 111.1(3) . 2_666
O1 C3 C2 110.5(4) . .
O1 C3 C4 107.8(3) . .
C2 C3 C4 110.4(4) . .
O1 C3 C5 108.6(4) . 2_756
C2 C3 C5 108.8(3) . 2_756
C4 C3 C5 110.8(3) . 2_756
C4 C5 C3 124.7(4) . 2_756
C4 C5 Br2 122.9(3) . .
C3 C5 Br2 112.5(3) 2_756 .
C34 C35 C33 124.7(4) . 2_557
C34 C35 Br32 122.3(3) . .
C33 C35 Br32 113.0(3) 2_557 .
C15 C14 C13 124.1(4) . .
C15 C14 Br11 122.4(3) . .
C13 C14 Br11 113.5(3) . .
C14 C15 C13 124.6(4) . 2_666
C14 C15 Br12 123.3(3) . .
C13 C15 Br12 112.1(3) 2_666 .
O3 C23 C22 110.0(3) . .
O3 C23 C25 107.9(3) . 2_567
C22 C23 C25 109.8(3) . 2_567
O3 C23 C24 107.7(3) . .
C22 C23 C24 110.6(4) . .
C25 C23 C24 110.8(3) 2_567 .
O4 C33 C32 109.9(3) . .
O4 C33 C35 109.2(3) . 2_557
C32 C33 C35 109.8(3) . 2_557
O4 C33 C34 106.7(3) . .
C32 C33 C34 110.1(3) . .
C35 C33 C34 111.1(3) 2_557 .
C25 C24 C23 124.1(4) . .
C25 C24 Br21 122.3(3) . .
C23 C24 Br21 113.5(3) . .
C33 O4 H4A 108(4) . .
C13 O2 H2A 93(9) . .
C21 C22 C23 176.0(5) . .
C1 C2 C3 176.9(5) . .
C31 C32 C33 176.9(5) . .
C22 C21 H21 173(4) . .
C11 C12 C13 178.2(6) . .
C2 C1 H1 177(4) . .
C12 C11 H11 167(5) . .
C32 C31 H4 175(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br32 C35 1.886(4) .
Br21 C24 1.887(4) .
Br22 C25 1.888(4) .
Br11 C14 1.889(4) .
Br31 C34 1.892(4) .
Br1 C4 1.889(4) .
Br2 C5 1.889(4) .
Br12 C15 1.891(4) .
O3 C23 1.431(5) .
O3 H3A 0.66(6) .
O1 C3 1.419(5) .
O1 H1A 0.69(6) .
C34 C35 1.329(6) .
C34 C33 1.526(6) .
C25 C24 1.330(6) .
C25 C23 1.522(6) 2_567
C4 C5 1.318(6) .
C4 C3 1.517(6) .
C13 O2 1.429(5) .
C13 C12 1.481(6) .
C13 C14 1.522(6) .
C13 C15 1.525(6) 2_666
C3 C2 1.491(6) .
C3 C5 1.537(6) 2_756
C5 C3 1.537(6) 2_756
C35 C33 1.522(6) 2_557
C14 C15 1.319(6) .
C15 C13 1.525(6) 2_666
C23 C22 1.481(6) .
C23 C25 1.522(6) 2_567
C23 C24 1.523(6) .
C33 O4 1.428(5) .
C33 C32 1.488(6) .
C33 C35 1.522(6) 2_557
O4 H4A 0.78(6) .
O2 H2A 0.64(9) .
C22 C21 1.185(6) .
C2 C1 1.183(7) .
C32 C31 1.164(7) .
C21 H21 0.98(6) .
C12 C11 1.172(7) .
C1 H1 0.90(7) .
C11 H11 0.83(7) .
C31 H4 0.70(7) .
