#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:02:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180220 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/06/7110634.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7110634
loop_
_publ_author_name
'Bilton, Clair'
'Howard, Judith A. K.'
'Laxmi Madhavi, N. N.'
'Nangia, Ashwini'
'Desiraju, Gautam R.'
'Allen, Frank H.'
'Wilson, Chick C.'
_publ_section_title
;
 When is a polymorph not a polymorph? Helical trimeric
 O--H···O synthons in
 trans-1,4-diethynylcyclohexane-1,4-diol
;
_journal_issue                   17
_journal_name_full               'Chemical Communications'
_journal_page_first              1675
_journal_paper_doi               10.1039/a905025f
_journal_year                    1999
_chemical_formula_moiety         'C10 H12 O2'
_chemical_formula_sum            'C10 H12 O2'
_chemical_formula_weight         164.20
_chemical_name_systematic
;
 ?
;
_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                105.689(2)
_cell_angle_beta                 101.838(1)
_cell_angle_gamma                94.736(1)
_cell_formula_units_Z            3
_cell_length_a                   6.4140(2)
_cell_length_b                   9.6367(3)
_cell_length_c                   11.7852(4)
_cell_measurement_reflns_used    510
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      5.12
_cell_volume                     678.98(4)
_computing_cell_refinement       'Brucker SMART'
_computing_data_collection       'Brucker SMART'
_computing_data_reduction        'Brucker SAINT'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 'not relevant'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Brucker SMART CCD'
_diffrn_measurement_method       'ω 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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4754
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0461
_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)+(0.0247P)²+0.4113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                2554
_reflns_number_total             3061
_reflns_threshold_expression     2sigma(I)
_cod_data_source_file            905025fsup1.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7110634
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
O1 O 1.12386(19) 0.68578(12) 0.67689(11) 0.0222(3) Uani 1 1 d
HA H 1.047(4) 0.734(2) 0.721(2) 0.037(6) Uiso 1 1 d
C1 C 0.9697(3) 0.4381(2) 0.81993(18) 0.0353(4) Uani 1 1 d
H1 H 0.940(4) 0.404(3) 0.885(3) 0.068(8) Uiso 1 1 d
C2 C 0.9983(3) 0.48304(17) 0.73940(15) 0.0241(3) Uani 1 1 d
C3 C 1.0257(2) 0.53514(16) 0.63476(14) 0.0190(3) Uani 1 1 d
C4 C 1.1787(3) 0.44656(17) 0.56924(15) 0.0209(3) Uani 1 1 d
C5 C 1.1962(2) 0.48260(17) 0.45247(14) 0.0197(3) Uani 1 1 d
O2 O 0.87712(19) 0.84379(12) 0.81177(10) 0.0214(3) Uani 1 1 d
HB H 0.751(4) 0.835(2) 0.762(2) 0.043(6) Uiso 1 1 d
C11 C 0.5431(3) 0.6511(2) 0.92444(18) 0.0355(4) Uani 1 1 d
H11 H 0.430(4) 0.574(3) 0.916(2) 0.064(8) Uiso 1 1 d
C12 C 0.6809(3) 0.74489(18) 0.93037(15) 0.0239(3) Uani 1 1 d
C13 C 0.8453(2) 0.86397(17) 0.93266(13) 0.0182(3) Uani 1 1 d
C14 C 0.7688(2) 1.01199(17) 0.97783(14) 0.0198(3) Uani 1 1 d
C15 C 0.9362(3) 1.13946(17) 0.98617(14) 0.0201(3) Uani 1 1 d
O3 O 0.49787(19) 0.82035(12) 0.65189(10) 0.0213(3) Uani 1 1 d
HC H 0.378(4) 0.782(3) 0.661(2) 0.050(7) Uiso 1 1 d
C21 C 0.3243(4) 1.1533(2) 0.7464(2) 0.0432(5) Uani 1 1 d
H21 H 0.277(5) 1.233(3) 0.795(3) 0.074(9) Uiso 1 1 d
C22 C 0.3903(3) 1.05744(19) 0.68329(15) 0.0267(4) Uani 1 1 d
C23 C 0.4707(2) 0.93995(16) 0.60130(14) 0.0187(3) Uani 1 1 d
C24 C 0.3142(3) 0.88773(17) 0.47544(15) 0.0211(3) Uani 1 1 d
C25 C 0.6951(2) 0.99377(18) 0.58873(15) 0.0212(3) Uani 1 1 d
H14B H 0.634(3) 1.0140(19) 0.9218(17) 0.021(4) Uiso 1 1 d
H5B H 1.264(3) 0.584(2) 0.4729(17) 0.024(5) Uiso 1 1 d
H15B H 0.959(3) 1.133(2) 0.9030(18) 0.027(5) Uiso 1 1 d
H5A H 1.286(3) 0.4169(18) 0.4094(16) 0.017(4) Uiso 1 1 d
H4A H 1.124(3) 0.3390(19) 0.5508(16) 0.019(4) Uiso 1 1 d
H4B H 1.322(3) 0.466(2) 0.6253(18) 0.027(5) Uiso 1 1 d
H25B H 0.796(3) 1.033(2) 0.6708(18) 0.025(5) Uiso 1 1 d
H15A H 0.886(3) 1.236(2) 1.0198(17) 0.023(5) Uiso 1 1 d
H24B H 0.367(3) 0.799(2) 0.4267(18) 0.031(5) Uiso 1 1 d
H24A H 0.170(3) 0.857(2) 0.4859(18) 0.029(5) Uiso 1 1 d
H14A H 0.739(3) 1.022(2) 1.0598(18) 0.028(5) Uiso 1 1 d
H25A H 0.750(3) 0.906(2) 0.5420(18) 0.028(5) 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'
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
_geom_angle_publ_flag
C3 O1 HA 107.2(14) . . yes
C2 C1 H1 177.2(17) . . yes
C1 C2 C3 177.53(19) . . yes
O1 C3 C2 110.12(13) . . yes
O1 C3 C5 110.28(12) . 2_766 yes
C2 C3 C5 109.15(13) . 2_766 yes
O1 C3 C4 107.28(12) . . yes
C2 C3 C4 109.46(13) . . yes
C5 C3 C4 110.54(12) 2_766 . yes
C5 C4 C3 112.56(13) . . yes
C5 C4 H4A 110.3(10) . . yes
C3 C4 H4A 108.1(10) . . yes
C5 C4 H4B 110.0(11) . . yes
C3 C4 H4B 108.5(11) . . yes
H4A C4 H4B 107.1(15) . . yes
C4 C5 C3 112.23(12) . 2_766 yes
C4 C5 H5B 109.2(11) . . yes
C3 C5 H5B 108.2(11) 2_766 . yes
C4 C5 H5A 109.9(10) . . yes
C3 C5 H5A 108.2(10) 2_766 . yes
H5B C5 H5A 109.1(15) . . yes
C13 O2 HB 108.2(15) . . yes
C12 C11 H11 177.8(16) . . yes
C11 C12 C13 177.03(19) . . yes
O2 C13 C12 109.12(12) . . yes
O2 C13 C15 106.79(12) . 2_777 yes
C12 C13 C15 111.25(13) . 2_777 yes
O2 C13 C14 109.87(12) . . yes
C12 C13 C14 109.64(13) . . yes
C15 C13 C14 110.13(12) 2_777 . yes
C15 C14 C13 111.89(12) . . yes
C15 C14 H14B 109.6(11) . . yes
C13 C14 H14B 108.7(11) . . yes
C15 C14 H14A 109.4(11) . . yes
C13 C14 H14A 109.0(11) . . yes
H14B C14 H14A 108.2(15) . . yes
C14 C15 C13 111.55(13) . 2_777 yes
C14 C15 H15B 109.5(11) . . yes
C13 C15 H15B 107.3(11) 2_777 . yes
C14 C15 H15A 110.6(11) . . yes
C13 C15 H15A 108.8(11) 2_777 . yes
H15B C15 H15A 109.0(15) . . yes
C23 O3 HC 112.1(16) . . yes
C22 C21 H21 176.9(19) . . yes
C21 C22 C23 178.14(19) . . yes
O3 C23 C22 110.22(12) . . yes
O3 C23 C24 110.42(12) . . yes
C22 C23 C24 110.20(13) . . yes
O3 C23 C25 105.86(12) . . yes
C22 C23 C25 110.61(13) . . yes
C24 C23 C25 109.45(12) . . yes
C25 C24 C23 111.99(13) 2_676 . yes
C25 C24 H24B 110.6(11) 2_676 . yes
C23 C24 H24B 106.7(11) . . yes
C25 C24 H24A 110.6(11) 2_676 . yes
C23 C24 H24A 108.1(11) . . yes
H24B C24 H24A 108.6(16) . . yes
C24 C25 C23 111.38(13) 2_676 . yes
C24 C25 H25B 109.0(11) 2_676 . yes
C23 C25 H25B 110.1(11) . . yes
C24 C25 H25A 111.3(11) 2_676 . yes
C23 C25 H25A 106.9(11) . . yes
H25B C25 H25A 108.1(15) . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.4426(18) . yes
O1 HA 0.86(2) . yes
C1 C2 1.184(3) . yes
C1 H1 0.96(3) . yes
C2 C3 1.488(2) . yes
C3 C5 1.542(2) 2_766 yes
C3 C4 1.543(2) . yes
C4 C5 1.531(2) . yes
C4 H4A 1.016(18) . yes
C4 H4B 0.98(2) . yes
C5 C3 1.542(2) 2_766 yes
C5 H5B 0.979(19) . yes
C5 H5A 0.997(17) . yes
O2 C13 1.4441(18) . yes
O2 HB 0.88(2) . yes
C11 C12 1.187(3) . yes
C11 H11 0.96(3) . yes
C12 C13 1.484(2) . yes
C13 C15 1.535(2) 2_777 yes
C13 C14 1.540(2) . yes
C14 C15 1.531(2) . yes
C14 H14B 0.980(19) . yes
C14 H14A 1.00(2) . yes
C15 C13 1.535(2) 2_777 yes
C15 H15B 1.01(2) . yes
C15 H15A 1.014(19) . yes
O3 C23 1.4411(18) . yes
O3 HC 0.86(3) . yes
C21 C22 1.186(3) . yes
C21 H21 0.94(3) . yes
C22 C23 1.480(2) . yes
C23 C24 1.537(2) . yes
C23 C25 1.539(2) . yes
C24 C25 1.530(2) 2_676 yes
C24 H24B 1.02(2) . yes
C24 H24A 0.99(2) . yes
C25 C24 1.530(2) 2_676 yes
C25 H25B 1.00(2) . yes
C25 H25A 1.01(2) . yes
