#------------------------------------------------------------------------------
#$Date: 2008-02-29 13:03:34 +0200 (Fri, 29 Feb 2008) $
#$Revision: 179 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2015262.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2015262
loop_
_publ_author_name
'Hamann, Uwe'
'K\"ampen, Jan'
'Bubenitschek, Peter'
'Hopf, Henning'
'Jones, Peter G.'
_publ_section_title
;
C\\tb C---H systems as hydrogen-bond donors and acceptors:
<i>trans</i>-1,2-diethynylcyclohexane-1,2-diol and
<i>trans</i>-1,4-diprop-2-ynylcyclohexane-1,4-diol monohydrate
;
_journal_coeditor_code           LN3003
_journal_issue                   4
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              o178
_journal_page_last               o181
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H18 O3'
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26
_chemical_name_systematic
;
trans-1,4-diprop-2-ynylcyclohexane-1,4-diol hydrate
;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                93.384(16)
_cell_angle_beta                 102.410(16)
_cell_angle_gamma                102.309(16)
_cell_formula_units_Z            2
_cell_length_a                   6.6112(18)
_cell_length_b                   7.2474(19)
_cell_length_c                   12.577(3)
_cell_measurement_reflns_used    56
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10
_cell_volume                     571.5(3)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1992)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1992)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe STADI-4'
_diffrn_measurement_method       \w/\q
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2374
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0340
_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/[\s^2^(Fo^2^)+(0.0362P)^2^+0.2046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                1849
_reflns_number_total             2022
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ln3003.cif
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_
_atom_site_type_symbol
_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
O O1 0.84693(14) 0.39717(13) 0.82084(7) 0.0223(2) Uani d D 1
H H01 0.730(3) 0.414(3) 0.7798(14) 0.047(5) Uiso d D 1
C C1 0.81482(19) 0.36043(17) 0.92784(10) 0.0196(3) Uani d . 1
C C2 1.01113(19) 0.30015(17) 0.98931(10) 0.0216(3) Uani d . 1
H H2A 1.0331 0.1909 0.9457 0.026 Uiso calc R 1
H H2B 0.9864 0.2578 1.0598 0.026 Uiso calc R 1
C C3 0.78829(19) 0.53954(17) 0.98833(10) 0.0212(3) Uani d . 1
H H3A 0.6681 0.5832 0.9440 0.025 Uiso calc R 1
H H3B 0.7528 0.5087 1.0588 0.025 Uiso calc R 1
C C4 0.6122(2) 0.20182(18) 0.91501(11) 0.0243(3) Uani d . 1
H H4A 0.5899 0.1765 0.9886 0.029 Uiso calc R 1
H H4B 0.4884 0.2466 0.8754 0.029 Uiso calc R 1
C C5 0.6205(2) 0.02421(19) 0.85603(11) 0.0249(3) Uani d . 1
C C6 0.6284(2) -0.1173(2) 0.80689(12) 0.0296(3) Uani d D 1
H H6 0.633(3) -0.230(2) 0.7677(14) 0.046(5) Uiso d D 1
O O1' 0.49797(14) 0.45806(12) 0.67637(7) 0.0216(2) Uani d D 1
H H01' 0.383(3) 0.477(3) 0.6934(15) 0.049(5) Uiso d D 1
C C1' 0.44261(19) 0.34810(17) 0.57046(10) 0.0193(3) Uani d . 1
C C2' 0.27312(19) 0.41941(18) 0.49225(10) 0.0206(3) Uani d . 1
H H2'1 0.1468 0.4108 0.5237 0.025 Uiso calc R 1
H H2'2 0.2287 0.3366 0.4219 0.025 Uiso calc R 1
C C3' 0.64711(19) 0.37550(18) 0.52919(10) 0.0206(3) Uani d . 1
H H3'1 0.7588 0.3389 0.5842 0.025 Uiso calc R 1
H H3'2 0.6207 0.2906 0.4606 0.025 Uiso calc R 1
C C4' 0.3643(2) 0.13701(18) 0.58442(11) 0.0238(3) Uani d . 1
H H4'1 0.3150 0.0628 0.5112 0.029 Uiso calc R 1
H H4'2 0.4850 0.0905 0.6260 0.029 Uiso calc R 1
C C5' 0.1907(2) 0.10345(18) 0.64148(11) 0.0265(3) Uani d . 1
C C6' 0.0553(2) 0.0849(2) 0.69061(13) 0.0354(4) Uani d D 1
H H6' -0.049(3) 0.073(3) 0.7311(15) 0.053(5) Uiso d D 1
O O3 0.17155(17) 0.58949(16) 0.73225(10) 0.0375(3) Uani d D 1
H H03 0.070(3) 0.536(3) 0.7641(17) 0.071(7) Uiso d D 1
H H04 0.179(4) 0.711(2) 0.739(2) 0.097(9) Uiso d D 1
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
O1 0.0185(5) 0.0289(5) 0.0189(5) 0.0044(4) 0.0042(4) 0.0032(4)
C1 0.0181(6) 0.0219(6) 0.0185(6) 0.0035(5) 0.0044(5) 0.0027(5)
C2 0.0223(6) 0.0198(6) 0.0223(6) 0.0059(5) 0.0039(5) 0.0011(5)
C3 0.0184(6) 0.0243(7) 0.0218(6) 0.0077(5) 0.0043(5) 0.0024(5)
C4 0.0211(7) 0.0247(7) 0.0262(7) 0.0020(5) 0.0071(5) 0.0019(5)
C5 0.0197(6) 0.0257(7) 0.0261(7) -0.0007(5) 0.0037(5) 0.0063(6)
C6 0.0292(7) 0.0230(7) 0.0338(8) 0.0009(6) 0.0066(6) 0.0027(6)
O1' 0.0201(5) 0.0253(5) 0.0193(5) 0.0062(4) 0.0044(4) -0.0005(4)
C1' 0.0198(6) 0.0198(6) 0.0185(6) 0.0054(5) 0.0042(5) 0.0007(5)
C2' 0.0168(6) 0.0239(6) 0.0211(6) 0.0049(5) 0.0042(5) 0.0013(5)
C3' 0.0186(6) 0.0233(6) 0.0216(6) 0.0085(5) 0.0044(5) 0.0036(5)
C4' 0.0246(7) 0.0220(7) 0.0264(7) 0.0071(5) 0.0077(5) 0.0036(5)
C5' 0.0282(7) 0.0215(7) 0.0283(7) 0.0036(5) 0.0053(6) 0.0033(5)
C6' 0.0321(8) 0.0365(8) 0.0381(8) 0.0028(6) 0.0141(7) 0.0054(7)
O3 0.0317(6) 0.0352(6) 0.0502(7) 0.0050(5) 0.0224(5) 0.0035(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.4381(15) y
O1 H01 . 0.871(15) ?
C1 C2 . 1.5242(17) ?
C1 C3 . 1.5273(17) ?
C1 C4 . 1.5396(17) ?
C2 C3 2_767 1.5270(18) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.4646(19) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.182(2) y
C6 H6 . 0.939(16) ?
O1' C1' . 1.4437(15) y
O1' H01' . 0.867(15) ?
C1' C2' . 1.5242(17) ?
C1' C3' . 1.5284(17) ?
C1' C4' . 1.5403(18) ?
C2' C3' 2_666 1.5279(18) ?
C2' H2'1 . 0.9900 ?
C2' H2'2 . 0.9900 ?
C3' H3'1 . 0.9900 ?
C3' H3'2 . 0.9900 ?
C4' C5' . 1.4654(19) ?
C4' H4'1 . 0.9900 ?
C4' H4'2 . 0.9900 ?
C5' C6' . 1.182(2) y
C6' H6' . 0.932(16) ?
O3 H03 . 0.884(16) ?
O3 H04 . 0.872(17) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H01 . . 109.5(12) ?
O1 C1 C2 . . 107.03(10) ?
O1 C1 C3 . . 110.20(10) ?
C2 C1 C3 . . 110.23(10) ?
O1 C1 C4 . . 108.81(10) ?
C2 C1 C4 . . 111.28(10) ?
C3 C1 C4 . . 109.25(10) ?
C1 C2 C3 . 2_767 112.44(10) ?
C1 C2 H2A . . 109.1 ?
C3 C2 H2A 2_767 . 109.1 ?
C1 C2 H2B . . 109.1 ?
C3 C2 H2B 2_767 . 109.1 ?
H2A C2 H2B . . 107.8 ?
C2 C3 C1 2_767 . 112.33(10) ?
C2 C3 H3A 2_767 . 109.1 ?
C1 C3 H3A . . 109.1 ?
C2 C3 H3B 2_767 . 109.1 ?
C1 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.9 ?
C5 C4 C1 . . 113.46(11) ?
C5 C4 H4A . . 108.9 ?
C1 C4 H4A . . 108.9 ?
C5 C4 H4B . . 108.9 ?
C1 C4 H4B . . 108.9 ?
H4A C4 H4B . . 107.7 ?
C6 C5 C4 . . 178.75(14) y
C5 C6 H6 . . 179.4(11) ?
C1' O1' H01' . . 109.5(12) ?
O1' C1' C2' . . 110.06(10) ?
O1' C1' C3' . . 106.34(10) ?
C2' C1' C3' . . 110.48(10) ?
O1' C1' C4' . . 108.92(10) ?
C2' C1' C4' . . 111.30(10) ?
C3' C1' C4' . . 109.61(10) ?
C1' C2' C3' . 2_666 112.21(10) ?
C1' C2' H2'1 . . 109.2 ?
C3' C2' H2'1 2_666 . 109.2 ?
C1' C2' H2'2 . . 109.2 ?
C3' C2' H2'2 2_666 . 109.2 ?
H2'1 C2' H2'2 . . 107.9 ?
C2' C3' C1' 2_666 . 112.22(10) ?
C2' C3' H3'1 2_666 . 109.2 ?
C1' C3' H3'1 . . 109.2 ?
C2' C3' H3'2 2_666 . 109.2 ?
C1' C3' H3'2 . . 109.2 ?
H3'1 C3' H3'2 . . 107.9 ?
C5' C4' C1' . . 113.00(11) ?
C5' C4' H4'1 . . 109.0 ?
C1' C4' H4'1 . . 109.0 ?
C5' C4' H4'2 . . 109.0 ?
C1' C4' H4'2 . . 109.0 ?
H4'1 C4' H4'2 . . 107.8 ?
C6' C5' C4' . . 176.68(15) y
C5' C6' H6' . . 178.2(12) ?
H03 O3 H04 . . 107(2) ?
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_site_symmetry_4
_geom_torsion
O1 C1 C2 C3 2_767 66.02(13)
C3 C1 C2 C3 2_767 -53.83(14)
C4 C1 C2 C3 2_767 -175.21(10)
O1 C1 C3 C2 2_767 -64.15(13)
C2 C1 C3 C2 2_767 53.77(15)
C4 C1 C3 C2 2_767 176.35(10)
O1 C1 C4 C5 . 58.64(14)
C2 C1 C4 C5 . -59.06(14)
C3 C1 C4 C5 . 179.00(11)
O1' C1' C2' C3' 2_666 63.20(13)
C3' C1' C2' C3' 2_666 -53.94(14)
C4' C1' C2' C3' 2_666 -175.95(10)
O1' C1' C3' C2' 2_666 -65.47(13)
C2' C1' C3' C2' 2_666 53.94(15)
C4' C1' C3' C2' 2_666 176.94(10)
O1' C1' C4' C5' . 54.05(14)
C2' C1' C4' C5' . -67.47(14)
C3' C1' C4' C5' . 170.01(11)
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 H01 O1' . 0.871(15) 1.882(15) 2.7470(14) 172.2(17)
O1' H01' O3 . 0.867(15) 1.895(15) 2.7399(15) 164.4(17)
O3 H03 O1 1_455 0.884(16) 1.899(16) 2.7795(15) 174(2)
C6 H6 O1' 1_545 0.939(16) 2.370(17) 3.2516(19) 156.3(15)
C6' H6' O1 1_455 0.932(16) 2.825(18) 3.4004(19) 121.0(14)