#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:02:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180220 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/06/7110635.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_7110635
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 H14 O3'
_chemical_formula_sum            'C10 H14 O3'
_chemical_formula_weight         182.00
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.925(2)
_cell_length_b                   6.1343(12)
_cell_length_c                   16.725(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150
_cell_volume                     987.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'Time of flight LAUE diffraction'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.5-5.0
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9863
_diffrn_reflns_theta_max         23.54
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
The linear absorption coefficient is wavelength dependent and it is
calculated as:
mu = 1.17 + 1.09 * lambda [cm^-1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             126
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          2
_exptl_crystal_size_min          1.5
_refine_diff_density_max         2.242
_refine_diff_density_min         -1.708
_refine_diff_density_rms         0.341
_refine_ls_extinction_coef       0.23
_refine_ls_extinction_method     'Becker-Coppens Lorentzian model'
_refine_ls_goodness_of_fit_ref   3.792
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.792
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0888
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                2659
_reflns_number_total             2661
_reflns_threshold_expression     2sigma(I)
_cod_data_source_file            905025fsup1.cif
_cod_data_source_block           3
_cod_original_cell_volume        987.5(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7110635
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_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 0.5801(3) 0.0888(4) 0.85373(17) 0.0159(5) Uani 1 1 d
HA H 0.6079(6) -0.0334(8) 0.8222(3) 0.0292(10) Uani 1 1 d
C1 C 0.3001(3) -0.2507(4) 0.83121(17) 0.0247(5) Uani 1 1 d
H1 H 0.2194(7) -0.3582(10) 0.7981(5) 0.0556(18) Uani 1 1 d
C2 C 0.3916(2) -0.1333(4) 0.86785(15) 0.0160(4) Uani 1 1 d
C3 C 0.5089(2) 0.0038(3) 0.91205(14) 0.0126(4) Uani 1 1 d
C4 C 0.6073(2) -0.1359(4) 0.97772(14) 0.0148(4) Uani 1 1 d
H4A H 0.6394(6) -0.2792(8) 0.9481(3) 0.0325(11) Uani 1 1 d
H4B H 0.6998(5) -0.0353(8) 1.0031(3) 0.0281(10) Uani 1 1 d
C5 C 0.5409(2) -0.2021(3) 1.04709(14) 0.0141(4) Uani 1 1 d
H5A H 0.6164(5) -0.2963(8) 1.0940(3) 0.0307(11) Uani 1 1 d
H5B H 0.4490(5) -0.3051(8) 1.0232(3) 0.0309(11) Uani 1 1 d
O2 O 0.7598(3) -0.5574(4) 0.87393(18) 0.0193(5) Uani 1 1 d
HB H 0.7106(5) -0.7004(8) 0.8710(3) 0.0298(11) Uani 1 1 d
C11 C 1.0574(3) -0.7927(5) 0.8400(2) 0.0386(7) Uani 1 1 d
H11 H 1.1209(10) -0.8862(18) 0.8088(6) 0.088(3) Uani 1 1 d
C12 C 0.9860(3) -0.6958(4) 0.87693(18) 0.0241(5) Uani 1 1 d
C13 C 0.8997(2) -0.5704(3) 0.92163(15) 0.0156(4) Uani 1 1 d
C14 C 0.9528(2) -0.3356(4) 0.93489(16) 0.0180(5) Uani 1 1 d
H14A H 0.9541(6) -0.2630(8) 0.8757(3) 0.0350(12) Uani 1 1 d
H14B H 0.8757(5) -0.2439(8) 0.9601(4) 0.0336(12) Uani 1 1 d
C15 C 0.9033(2) -0.6780(4) 1.00513(16) 0.0189(5) Uani 1 1 d
H15A H 0.8719(6) -0.8473(9) 0.9963(4) 0.0377(13) Uani 1 1 d
H15B H 0.8261(5) -0.5960(9) 1.0322(4) 0.0361(13) Uani 1 1 d
O3 O 0.3478(3) 0.2265(5) 0.2343(2) 0.0210(5) Uani 1 1 d
HC H 0.4305(6) 0.2810(10) 0.2742(4) 0.0389(13) Uani 1 1 d
HD H 0.3101(6) 0.3525(9) 0.2017(4) 0.0384(13) Uani 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 6.646 'International Tables Vol C Tables 4.4.4.1'
H H -3.739 'International Tables Vol C Tables 4.4.4.1'
O O 5.803 'International Tables Vol C Tables 4.4.4.1'
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 109.4(4) . . yes
C2 C1 H1 178.9(5) . . yes
C1 C2 C3 177.3(2) . . yes
O1 C3 C2 109.0(2) . . yes
O1 C3 C5 106.25(18) . 3_657 yes
C2 C3 C5 111.95(17) . 3_657 yes
O1 C3 C4 110.79(19) . . yes
C2 C3 C4 108.97(17) . . yes
C5 C3 C4 109.90(18) 3_657 . yes
C5 C4 C3 112.01(17) . . yes
C5 C4 H4A 111.0(4) . . yes
C3 C4 H4A 109.2(3) . . yes
C5 C4 H4B 109.3(4) . . yes
C3 C4 H4B 106.7(3) . . yes
H4A C4 H4B 108.5(4) . . yes
C4 C5 C3 111.94(17) . 3_657 yes
C4 C5 H5A 109.6(3) . . yes
C3 C5 H5A 109.5(3) 3_657 . yes
C4 C5 H5B 110.5(3) . . yes
C3 C5 H5B 106.8(3) 3_657 . yes
H5A C5 H5B 108.4(4) . . yes
C13 O2 HB 112.0(4) . . yes
C12 C11 H11 177.1(8) . . yes
C11 C12 C13 178.3(3) . . yes
O2 C13 C12 110.5(2) . . yes
O2 C13 C14 106.4(2) . . yes
C12 C13 C14 109.9(2) . . yes
O2 C13 C15 109.7(2) . . yes
C12 C13 C15 110.32(19) . . yes
C14 C13 C15 109.96(19) . . yes
C13 C14 C15 112.25(19) . 3_747 yes
C13 C14 H14A 109.5(3) . . yes
C15 C14 H14A 110.9(3) 3_747 . yes
C13 C14 H14B 106.7(3) . . yes
C15 C14 H14B 109.9(4) 3_747 . yes
H14A C14 H14B 107.4(5) . . yes
C14 C15 C13 112.47(18) 3_747 . yes
C14 C15 H15A 109.4(4) 3_747 . yes
C13 C15 H15A 110.2(4) . . yes
C14 C15 H15B 109.6(4) 3_747 . yes
C13 C15 H15B 108.2(4) . . yes
H15A C15 H15B 106.7(5) . . yes
HC O3 HD 104.8(6) . . 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 1.435(3) . yes
O1 HA 0.993(6) . yes
C1 C2 1.203(3) . yes
C1 H1 1.080(6) . yes
C2 C3 1.479(3) . yes
C3 C5 1.535(3) 3_657 yes
C3 C4 1.540(3) . yes
C4 C5 1.523(3) . yes
C4 H4A 1.094(5) . yes
C4 H4B 1.102(5) . yes
C5 C3 1.535(3) 3_657 yes
C5 H5A 1.107(5) . yes
C5 H5B 1.101(6) . yes
O2 C13 1.425(4) . yes
O2 HB 1.000(6) . yes
C11 C12 1.205(4) . yes
C11 H11 1.076(8) . yes
C12 C13 1.482(4) . yes
C13 C14 1.531(3) . yes
C13 C15 1.537(3) . yes
C14 C15 1.534(3) 3_747 yes
C14 H14A 1.089(6) . yes
C14 H14B 1.112(6) . yes
C15 C14 1.534(3) 3_747 yes
C15 H15A 1.084(6) . yes
C15 H15B 1.102(6) . yes
O3 HC 0.982(8) . yes
O3 HD 0.967(7) . yes
