#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/47/2204761.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_2204761
loop_
_publ_author_name
'Arkasish Bandyopadhyay'
'Babu Varghese'
'Sankararaman, Sethuraman'
_publ_section_title
;
 (Z)-3,6-Diethynyl-3,6-dihydroxycyclohexa-1,4-diene
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2247
_journal_page_last               o2248
_journal_paper_doi               10.1107/S1600536804027631
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H8 O2'
_chemical_formula_moiety         'C10 H8 O2'
_chemical_formula_sum            'C10 H8 O2'
_chemical_formula_weight         160.16
_chemical_melting_point          398.1(10)
_chemical_name_systematic
;
(Z)-3,6-Diethynyl-3,6-dihydroxycyclohexa-1,4-diene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.06(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.598(2)
_cell_length_b                   6.2646(10)
_cell_length_c                   14.153(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     918.9(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1999)'
_computing_publication_material  'SHELXL97 and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_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  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1712
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1617
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1702
_refine_ls_R_factor_gt           0.0592
_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)+(0.0602P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                730
_reflns_number_total             1617
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6423.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '124-126 \%C' was changed to
'398.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
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 '124-126 \%C' was changed to
'398.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204761
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
C1 0.7342(3) 0.2621(6) 0.7495(3) 0.0520(9) Uani d D 1 C
C2 0.6918(3) 0.0387(6) 0.7243(2) 0.0456(9) Uani d . 1 C
C3 0.6383(3) -0.0649(6) 0.8033(3) 0.0575(10) Uani d D 1 C
C4 0.6516(4) 0.0164(7) 0.8903(3) 0.0661(11) Uani d D 1 C
C5 0.7126(3) 0.2264(7) 0.9197(2) 0.0619(11) Uani d . 1 C
C6 0.7450(4) 0.3448(6) 0.8364(3) 0.0620(10) Uani d D 1 C
C7 0.8007(4) -0.0879(6) 0.7055(2) 0.0589(10) Uani d . 1 C
C8 0.8867(5) -0.1847(7) 0.6899(3) 0.0927(16) Uani d . 1 C
C9 0.8314(4) 0.2037(6) 0.9943(3) 0.0683(11) Uani d . 1 C
C10 0.9279(4) 0.1899(7) 1.0515(3) 0.0918(15) Uani d . 1 C
O1 0.5881(2) 0.0397(4) 0.64040(16) 0.0634(8) Uani d . 1 O
O2 0.6264(3) 0.3535(5) 0.96314(18) 0.0969(11) Uani d . 1 O
H1 0.756(3) 0.344(4) 0.6977(14) 0.062(10) Uiso d D 1 H
H1' 0.6133 0.0927 0.5947 0.14(2) Uiso calc R 1 H
H2' 0.5604 0.3784 0.9228 0.15(2) Uiso calc R 1 H
H3 0.597(3) -0.200(2) 0.785(2) 0.055(10) Uiso d D 1 H
H4 0.613(3) -0.065(5) 0.935(2) 0.078(12) Uiso d D 1 H
H6 0.763(3) 0.4945(14) 0.845(2) 0.067(12) Uiso d D 1 H
H8 0.9560 -0.2628 0.6772 0.111 Uiso calc R 1 H
H10 1.0048 0.1789 1.0970 0.110 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.058(2) 0.052(3) 0.046(2) -0.0053(19) 0.0095(18) 0.0053(19)
C2 0.0437(18) 0.062(3) 0.0311(17) -0.0071(18) 0.0069(15) 0.0009(17)
C3 0.057(2) 0.062(3) 0.053(2) -0.009(2) 0.0110(18) 0.004(2)
C4 0.063(2) 0.095(3) 0.043(2) 0.005(2) 0.0173(19) 0.016(2)
C5 0.059(2) 0.087(3) 0.039(2) 0.026(2) 0.0079(18) -0.007(2)
C6 0.077(3) 0.053(3) 0.052(2) 0.011(2) 0.0035(19) -0.005(2)
C7 0.061(2) 0.065(3) 0.054(2) 0.000(2) 0.0185(19) -0.005(2)
C8 0.086(3) 0.092(4) 0.108(4) 0.014(3) 0.036(3) -0.012(3)
C9 0.073(3) 0.084(3) 0.046(2) 0.030(2) 0.007(2) -0.008(2)
C10 0.080(3) 0.113(4) 0.074(3) 0.032(3) -0.004(2) -0.011(3)
O1 0.0512(13) 0.099(2) 0.0368(13) -0.0170(15) 0.0023(11) 0.0037(14)
O2 0.0849(19) 0.159(3) 0.0422(14) 0.067(2) 0.0024(14) -0.0175(17)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 123.8(3)
C6 C1 H1 120.9(19)
C2 C1 H1 115.2(18)
O1 C2 C7 110.3(3)
O1 C2 C1 109.5(3)
C7 C2 C1 110.0(3)
O1 C2 C3 105.9(3)
C7 C2 C3 109.5(3)
C1 C2 C3 111.6(3)
C4 C3 C2 123.2(4)
C4 C3 H3 123.0(18)
C2 C3 H3 113.8(18)
C3 C4 C5 124.1(4)
C3 C4 H4 115(2)
C5 C4 H4 120(2)
O2 C5 C9 105.7(3)
O2 C5 C4 109.3(3)
C9 C5 C4 111.9(3)
O2 C5 C6 109.4(3)
C9 C5 C6 108.2(3)
C4 C5 C6 112.1(3)
C1 C6 C5 123.6(4)
C1 C6 H6 119(2)
C5 C6 H6 117(2)
C8 C7 C2 178.9(4)
C7 C8 H8 180.0
C10 C9 C5 177.6(5)
C9 C10 H10 180.0
C2 O1 H1' 109.5
C5 O2 H2' 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.316(5)
C1 C2 1.490(5)
C1 H1 0.96(2)
C2 O1 1.439(4)
C2 C7 1.469(5)
C2 C3 1.504(4)
C3 C4 1.312(5)
C3 H3 0.963(18)
C4 C5 1.487(5)
C4 H4 0.97(3)
C5 O2 1.442(4)
C5 C9 1.470(5)
C5 C6 1.493(5)
C6 H6 0.960(12)
C7 C8 1.154(5)
C8 H8 0.9300
C9 C10 1.168(5)
C10 H10 0.9300
O1 H1' 0.8200
O2 H2' 0.8200
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
O1 H1' O2 4_565 0.82 1.93 2.708(3) 159
O2 H2' O1 2_656 0.82 1.93 2.699(4) 157
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
C6 C1 C2 O1 128.3(3) ?
C6 C1 C2 C7 -110.4(4) ?
C6 C1 C2 C3 11.4(5) y
O1 C2 C3 C4 -131.7(4) ?
C7 C2 C3 C4 109.4(4) ?
C1 C2 C3 C4 -12.7(5) y
C2 C3 C4 C5 4.4(6) y
C3 C4 C5 O2 127.4(4) ?
C3 C4 C5 C9 -115.8(4) ?
C3 C4 C5 C6 5.9(5) y
C2 C1 C6 C5 -1.8(6) y
O2 C5 C6 C1 -128.7(4) ?
C9 C5 C6 C1 116.6(4) ?
C4 C5 C6 C1 -7.2(5) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9919623
