#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/52/2015262.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_2015262
loop_
_publ_author_name
'Hamann, Uwe'
'Kämpen, Jan'
'Bubenitschek, Peter'
'Hopf, Henning'
'Jones, Peter G.'
_publ_section_title
;
 C[tripleC---H systems as hydrogen-bond donors and acceptors:
 trans-1,2-diethynylcyclohexane-1,2-diol and
 trans-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_paper_doi               10.1107/S0108270106005063
_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
;
_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   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       ω/θ
_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/[σ²(Fo²)+(0.0362P)²+0.2046P] where P=(Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            ln3003.cif
_cod_data_source_block           IV
_cod_database_code               2015262
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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_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_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_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)
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)
