#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015261.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_2015261
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          'C10 H12 O2'
_chemical_formula_moiety         'C10 H12 O2'
_chemical_formula_sum            'C10 H12 O2'
_chemical_formula_weight         164.20
_chemical_name_systematic
;
trans-1,2-Diethynylcyclohexane-1,2-diol
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.46(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.563(3)
_cell_length_b                   23.839(6)
_cell_length_c                   7.025(2)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      8.5
_cell_volume                     1765.8(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4400
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.183
_refine_ls_extinction_coef       0.0080(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0446
_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)+(0.0332P)²+0.7551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                2380
_reflns_number_total             3131
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3003.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015261
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_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
C C1 0.83692(18) 0.62268(8) 0.3713(3) 0.0236(4) Uani d . 1
C C2 0.74653(17) 0.60275(7) 0.5244(3) 0.0204(4) Uani d . 1
C C3 0.81572(19) 0.60515(8) 0.7221(3) 0.0266(4) Uani d . 1
H H3A 0.8384 0.6445 0.7530 0.032 Uiso calc R 1
H H3B 0.7583 0.5916 0.8186 0.032 Uiso calc R 1
C C4 0.93575(19) 0.56940(9) 0.7314(3) 0.0324(5) Uani d . 1
H H4A 0.9803 0.5735 0.8587 0.039 Uiso calc R 1
H H4B 0.9125 0.5294 0.7136 0.039 Uiso calc R 1
C C5 1.02384(19) 0.58691(9) 0.5787(3) 0.0347(5) Uani d . 1
H H5A 1.0974 0.5611 0.5810 0.042 Uiso calc R 1
H H5B 1.0561 0.6252 0.6066 0.042 Uiso calc R 1
C C6 0.95592(18) 0.58596(9) 0.3813(3) 0.0293(5) Uani d . 1
H H6A 0.9319 0.5469 0.3480 0.035 Uiso calc R 1
H H6B 1.0145 0.5994 0.2864 0.035 Uiso calc R 1
C C7 0.86975(18) 0.68239(8) 0.4052(3) 0.0267(4) Uani d . 1
C C8 0.8953(2) 0.73001(10) 0.4312(3) 0.0384(5) Uani d D 1
H H8 0.916(3) 0.7683(8) 0.458(4) 0.063(8) Uiso d D 1
C C9 0.70117(17) 0.54546(8) 0.4804(3) 0.0229(4) Uani d . 1
C C10 0.6578(2) 0.50046(9) 0.4479(3) 0.0318(5) Uani d D 1
H H10 0.622(2) 0.4647(9) 0.419(4) 0.064(8) Uiso d D 1
O O1 0.77933(14) 0.61563(6) 0.18327(18) 0.0299(4) Uani d D 1
H H01 0.724(2) 0.6401(9) 0.171(4) 0.049(8) Uiso d D 1
O O2 0.63907(12) 0.63975(6) 0.52862(19) 0.0239(3) Uani d D 1
H H02 0.593(2) 0.6317(11) 0.433(3) 0.058(8) Uiso d D 1
C C1' 0.37595(17) 0.61074(8) 0.1025(3) 0.0226(4) Uani d . 1
C C2' 0.43125(17) 0.64112(8) -0.0689(3) 0.0238(4) Uani d . 1
C C3' 0.32330(19) 0.66407(8) -0.2016(3) 0.0299(5) Uani d . 1
H H3'1 0.3597 0.6856 -0.3056 0.036 Uiso calc R 1
H H3'2 0.2747 0.6323 -0.2599 0.036 Uiso calc R 1
C C4' 0.2336(2) 0.70171(9) -0.0983(3) 0.0359(5) Uani d . 1
H H4'1 0.2793 0.7360 -0.0539 0.043 Uiso calc R 1
H H4'2 0.1624 0.7132 -0.1879 0.043 Uiso calc R 1
C C5' 0.1817(2) 0.67186(9) 0.0713(3) 0.0342(5) Uani d . 1
H H5'1 0.1270 0.6403 0.0256 0.041 Uiso calc R 1
H H5'2 0.1290 0.6982 0.1413 0.041 Uiso calc R 1
C C6' 0.28866(19) 0.64962(8) 0.2053(3) 0.0286(5) Uani d . 1
H H6'1 0.3384 0.6815 0.2603 0.034 Uiso calc R 1
H H6'2 0.2522 0.6291 0.3116 0.034 Uiso calc R 1
C C7' 0.30831(19) 0.55942(8) 0.0360(3) 0.0258(4) Uani d . 1
C C8' 0.2575(2) 0.51775(9) -0.0130(3) 0.0342(5) Uani d D 1
H H8' 0.221(2) 0.4837(8) -0.056(3) 0.045(7) Uiso d D 1
C C9' 0.51511(19) 0.68756(8) 0.0020(3) 0.0285(5) Uani d . 1
C C10' 0.5809(2) 0.72564(9) 0.0496(3) 0.0375(5) Uani d D 1
H H10' 0.627(2) 0.7584(9) 0.084(4) 0.069(9) Uiso d D 1
O O1' 0.47707(13) 0.59540(6) 0.2389(2) 0.0308(4) Uani d D 1
H H01' 0.513(2) 0.5674(9) 0.197(4) 0.059(9) Uiso d D 1
O O2' 0.50258(14) 0.60008(6) -0.1628(2) 0.0314(4) Uani d D 1
H H02' 0.535(2) 0.6170(10) -0.251(3) 0.060(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
_geom_angle_publ_flag
O1 C1 C7 110.12(15) ?
O1 C1 C6 106.12(15) ?
C7 C1 C6 111.03(16) ?
O1 C1 C2 110.98(15) ?
C7 C1 C2 109.26(15) ?
C6 C1 C2 109.30(15) ?
O2 C2 C9 108.99(15) ?
O2 C2 C3 106.99(14) ?
C9 C2 C3 110.86(15) ?
O2 C2 C1 110.19(14) ?
C9 C2 C1 110.08(15) ?
C3 C2 C1 109.67(15) ?
C4 C3 C2 111.60(16) ?
C4 C3 H3A 109.3 ?
C2 C3 H3A 109.3 ?
C4 C3 H3B 109.3 ?
C2 C3 H3B 109.3 ?
H3A C3 H3B 108.0 ?
C5 C4 C3 111.02(17) ?
C5 C4 H4A 109.4 ?
C3 C4 H4A 109.4 ?
C5 C4 H4B 109.4 ?
C3 C4 H4B 109.4 ?
H4A C4 H4B 108.0 ?
C4 C5 C6 111.33(17) ?
C4 C5 H5A 109.4 ?
C6 C5 H5A 109.4 ?
C4 C5 H5B 109.4 ?
C6 C5 H5B 109.4 ?
H5A C5 H5B 108.0 ?
C5 C6 C1 111.96(16) ?
C5 C6 H6A 109.2 ?
C1 C6 H6A 109.2 ?
C5 C6 H6B 109.2 ?
C1 C6 H6B 109.2 ?
H6A C6 H6B 107.9 ?
C8 C7 C1 179.5(2) y
C7 C8 H8 177.6(16) ?
C10 C9 C2 176.1(2) y
C9 C10 H10 178.7(17) ?
C1 O1 H01 105.7(18) ?
C2 O2 H02 105.5(18) ?
O1' C1' C7' 108.99(15) ?
O1' C1' C6' 106.61(15) ?
C7' C1' C6' 111.05(16) ?
O1' C1' C2' 109.68(15) ?
C7' C1' C2' 109.82(15) ?
C6' C1' C2' 110.61(15) ?
O2' C2' C9' 110.29(15) ?
O2' C2' C3' 111.08(16) ?
C9' C2' C3' 110.21(16) ?
O2' C2' C1' 105.92(15) ?
C9' C2' C1' 109.46(16) ?
C3' C2' C1' 109.79(15) ?
C4' C3' C2' 112.54(16) ?
C4' C3' H3'1 109.1 ?
C2' C3' H3'1 109.1 ?
C4' C3' H3'2 109.1 ?
C2' C3' H3'2 109.1 ?
H3'1 C3' H3'2 107.8 ?
C5' C4' C3' 111.27(17) ?
C5' C4' H4'1 109.4 ?
C3' C4' H4'1 109.4 ?
C5' C4' H4'2 109.4 ?
C3' C4' H4'2 109.4 ?
H4'1 C4' H4'2 108.0 ?
C4' C5' C6' 111.02(17) ?
C4' C5' H5'1 109.4 ?
C6' C5' H5'1 109.4 ?
C4' C5' H5'2 109.4 ?
C6' C5' H5'2 109.4 ?
H5'1 C5' H5'2 108.0 ?
C1' C6' C5' 111.56(16) ?
C1' C6' H6'1 109.3 ?
C5' C6' H6'1 109.3 ?
C1' C6' H6'2 109.3 ?
C5' C6' H6'2 109.3 ?
H6'1 C6' H6'2 108.0 ?
C8' C7' C1' 177.8(2) y
C7' C8' H8' 176.3(15) ?
C10' C9' C2' 176.7(2) y
C9' C10' H10' 174.6(17) ?
C1' O1' H01' 107.8(19) ?
C2' O2' H02' 105.4(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.430(2) y
C1 C7 1.481(3) ?
C1 C6 1.530(3) ?
C1 C2 1.555(3) ?
C2 O2 1.439(2) y
C2 C9 1.474(3) ?
C2 C3 1.531(3) ?
C3 C4 1.526(3) ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C5 1.520(3) ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 C6 1.523(3) ?
C5 H5A 0.9900 ?
C5 H5B 0.9900 ?
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 C8 1.178(3) y
C8 H8 0.954(18) ?
C9 C10 1.183(3) y
C10 H10 0.950(18) ?
O1 H01 0.829(18) ?
O2 H02 0.828(19) ?
C1' O1' 1.438(2) y
C1' C7' 1.478(3) ?
C1' C6' 1.520(3) ?
C1' C2' 1.549(3) ?
C2' O2' 1.422(2) y
C2' C9' 1.485(3) ?
C2' C3' 1.530(3) ?
C3' C4' 1.521(3) ?
C3' H3'1 0.9900 ?
C3' H3'2 0.9900 ?
C4' C5' 1.519(3) ?
C4' H4'1 0.9900 ?
C4' H4'2 0.9900 ?
C5' C6' 1.522(3) ?
C5' H5'1 0.9900 ?
C5' H5'2 0.9900 ?
C6' H6'1 0.9900 ?
C6' H6'2 0.9900 ?
C7' C8' 1.171(3) y
C8' H8' 0.940(17) ?
C9' C10' 1.179(3) y
C10' H10' 0.944(18) ?
O1' H01' 0.832(19) ?
O2' H02' 0.832(19) ?
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
O2 H02 O1' . 0.828(19) 1.976(19) 2.787(2) 166(3)
O2' H02' O2 1_554 0.832(19) 2.02(2) 2.837(2) 165(3)
C10 H10 O2' 3_665 0.950(18) 2.66(2) 3.495(3) 147(2)
C8' H8' O1 3_665 0.940(17) 2.529(19) 3.411(3) 156(2)
C10' H10' O2 4_575 0.944(18) 2.46(2) 3.272(3) 144(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
O1 C1 C2 O2 -68.27(19)
C7 C1 C2 O2 53.3(2)
C6 C1 C2 O2 175.02(14)
O1 C1 C2 C9 52.0(2)
C7 C1 C2 C9 173.59(15)
C6 C1 C2 C9 -64.7(2)
O1 C1 C2 C3 174.20(15)
C7 C1 C2 C3 -64.18(19)
C6 C1 C2 C3 57.49(19)
O2 C2 C3 C4 -177.28(15)
C9 C2 C3 C4 64.0(2)
C1 C2 C3 C4 -57.8(2)
C2 C3 C4 C5 56.2(2)
C3 C4 C5 C6 -54.4(2)
C4 C5 C6 C1 56.0(2)
O1 C1 C6 C5 -176.97(16)
C7 C1 C6 C5 63.4(2)
C2 C1 C6 C5 -57.2(2)
O1' C1' C2' O2' 67.18(18)
C7' C1' C2' O2' -52.58(19)
C6' C1' C2' O2' -175.51(15)
O1' C1' C2' C9' -51.7(2)
C7' C1' C2' C9' -171.47(16)
C6' C1' C2' C9' 65.6(2)
O1' C1' C2' C3' -172.81(15)
C7' C1' C2' C3' 67.4(2)
C6' C1' C2' C3' -55.5(2)
O2' C2' C3' C4' 171.72(16)
C9' C2' C3' C4' -65.7(2)
C1' C2' C3' C4' 54.9(2)
C2' C3' C4' C5' -55.0(2)
C3' C4' C5' C6' 54.8(2)
O1' C1' C6' C5' 176.34(15)
C7' C1' C6' C5' -65.1(2)
C2' C1' C6' C5' 57.2(2)
C4' C5' C6' C1' -56.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25900444
