#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/57/2005790.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_2005790
loop_
_publ_author_name
'Boss, C.'
'Stoeckli-Evans, H.'
'Keese, R.'
_publ_section_title
;
 The First Crystal Structure Analysis of
 Cyclododeca-2,8-diyne-1,10-diols
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              3069
_journal_page_last               3073
_journal_paper_doi               10.1107/S0108270196009080
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C14 H20 O2'
_chemical_formula_sum            'C14 H20 O2'
_chemical_formula_weight         220.30
_chemical_melting_point          417.15
_chemical_name_systematic
;
 rac. 1,10-dimethyl-cyclododeca-2,8-diyne-1,10-diol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 94.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.115(2)
_cell_length_b                   10.4765(11)
_cell_length_c                   15.093(4)
_cell_measurement_reflns_used    7
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.0
_cell_measurement_theta_min      17.5
_cell_volume                     1279.0(5)
_computing_cell_refinement       STADI4
_computing_data_collection       'STADI4 (Stoe, 1986, 1996)'
_computing_data_reduction        'X-RED (Stoe, 1986, 1996)'
_computing_molecular_graphics    'PLUTON/PLATON (Spek, 1990)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Stoe AED2 4-circle diffractometer'
_diffrn_measurement_method       ω/2θ
_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
_diffrn_reflns_av_sigmaI/netI    0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1666
_diffrn_reflns_theta_max         22.49
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    none
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.149
_refine_ls_extinction_coef       0.0139(18)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.215
_refine_ls_goodness_of_fit_obs   1.221
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.215
_refine_ls_restrained_S_obs      1.221
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_obs          0.0515
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
 calc w = 1/[\s^2^(Fo^2^)+(0.0292P)^2^+0.7847P]
 where P = (Fo^2^+2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.1094
_refine_ls_wR_factor_obs         0.1053
_reflns_number_observed          1537
_reflns_number_total             1666
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            kh1110.cif
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '144\%C' was changed to '417.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1279.1(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2005790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
O1 1 0.4214(2) 0.6269(2) 0.40731(13) 0.0499(6) Uani d . O
H1 1 0.4808(39) 0.6443(30) 0.4494(21) 0.071(11) Uiso d . H
O10 1 0.1487(2) 0.8711(2) 0.05671(11) 0.0447(5) Uani d . O
H10 1 0.1484(36) 0.9478(31) 0.0742(20) 0.065(10) Uiso d . H
C1 1 0.3392(3) 0.7353(2) 0.36387(15) 0.0355(6) Uani d . C
C2 1 0.4475(3) 0.8486(2) 0.3738(2) 0.0380(6) Uani d . C
C3 1 0.5410(3) 0.9363(3) 0.3774(2) 0.0416(7) Uani d . C
C4 1 0.6566(3) 1.0438(2) 0.3751(2) 0.0494(7) Uani d . C
H4A 1 0.7595(3) 1.0220(2) 0.4089(2) 0.059 Uiso calc R H
H4B 1 0.6103(3) 1.1177(2) 0.4028(2) 0.059 Uiso calc R H
C5 1 0.6912(3) 1.0766(2) 0.2800(2) 0.0470(7) Uani d . C
H5A 1 0.5869(3) 1.0913(2) 0.2455(2) 0.056 Uiso calc R H
H5B 1 0.7539(3) 1.1555(2) 0.2804(2) 0.056 Uiso calc R H
C6 1 0.7863(3) 0.9737(3) 0.2344(2) 0.0494(7) Uani d . C
H6A 1 0.9035(3) 0.9925(3) 0.2427(2) 0.059 Uiso calc R H
H6B 1 0.7680(3) 0.8922(3) 0.2624(2) 0.059 Uiso calc R H
C7 1 0.7359(3) 0.9630(3) 0.1355(2) 0.0601(8) Uani d . C
H7A 1 0.7390(3) 1.0469(3) 0.1084(2) 0.072 Uiso calc R H
H7B 1 0.8140(3) 0.9088(3) 0.1078(2) 0.072 Uiso calc R H
C8 1 0.5685(3) 0.9092(3) 0.1196(2) 0.0476(7) Uani d . C
C9 1 0.4337(3) 0.8642(2) 0.1132(2) 0.0398(6) Uani d . C
C10 1 0.2711(3) 0.8002(2) 0.11050(15) 0.0341(6) Uani d . C
C11 1 0.2161(3) 0.7905(2) 0.20503(15) 0.0344(6) Uani d . C
H11A 1 0.1012(3) 0.7641(2) 0.20158(15) 0.041 Uiso calc R H
H11B 1 0.2226(3) 0.8746(2) 0.23192(15) 0.041 Uiso calc R H
C12 1 0.3177(3) 0.6974(2) 0.26574(15) 0.0364(6) Uani d . C
H12A 1 0.2650(3) 0.6143(2) 0.26122(15) 0.044 Uiso calc R H
H12B 1 0.4264(3) 0.6889(2) 0.24393(15) 0.044 Uiso calc R H
C13 1 0.1753(3) 0.7566(3) 0.4037(2) 0.0505(7) Uani d . C
H13A 1 0.1086(3) 0.6811(3) 0.3959(2) 0.061 Uiso calc R H
H13B 1 0.1185(3) 0.8271(3) 0.3743(2) 0.061 Uiso calc R H
H13C 1 0.1951(3) 0.7750(3) 0.4659(2) 0.061 Uiso calc R H
C14 1 0.2819(3) 0.6710(2) 0.0651(2) 0.0471(7) Uani d . C
H14A 1 0.1763(3) 0.6294(2) 0.0634(2) 0.056 Uiso calc R H
H14B 1 0.3632(3) 0.6192(2) 0.0978(2) 0.056 Uiso calc R H
H14C 1 0.3129(3) 0.6830(2) 0.0056(2) 0.056 Uiso calc R H
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 C2 109.6(2) yes
O1 C1 C13 108.8(2) yes
C2 C1 C13 112.0(2) yes
O1 C1 C12 104.4(2) yes
C2 C1 C12 109.1(2) yes
C13 C1 C12 112.7(2) yes
C3 C2 C1 175.5(3) yes
C2 C3 C4 175.9(3) yes
C3 C4 C5 111.2(2) yes
C6 C5 C4 113.9(2) yes
C7 C6 C5 113.0(2) yes
C8 C7 C6 111.1(2) yes
C9 C8 C7 175.3(3) yes
C8 C9 C10 175.3(3) yes
O10 C10 C9 110.9(2) yes
O10 C10 C14 105.5(2) yes
C9 C10 C14 109.4(2) yes
O10 C10 C11 108.7(2) yes
C9 C10 C11 109.3(2) yes
C14 C10 C11 113.0(2) yes
C10 C11 C12 114.6(2) yes
C1 C12 C11 115.3(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.447(3) yes
O10 C10 1.438(3) yes
C1 C2 1.478(4) yes
C1 C13 1.519(4) yes
C1 C12 1.530(3) yes
C2 C3 1.190(3) yes
C3 C4 1.467(4) yes
C4 C5 1.525(4) yes
C5 C6 1.522(4) yes
C6 C7 1.520(4) yes
C7 C8 1.473(4) yes
C8 C9 1.188(3) yes
C9 C10 1.478(4) yes
C10 C14 1.523(3) yes
C10 C11 1.532(3) yes
C11 C12 1.533(3) yes
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
_geom_torsion_publ_flag
O1 C1 C2 C3 75.(3) no
C13 C1 C2 C3 -164.(3) no
C12 C1 C2 C3 -39.(3) no
C1 C2 C3 C4 38(6) yes
C2 C3 C4 C5 4.(4) no
C3 C4 C5 C6 -67.2(3) no
C4 C5 C6 C7 145.7(2) yes
C5 C6 C7 C8 -70.2(3) no
C6 C7 C8 C9 -8.(4) no
C7 C8 C9 C10 -41(6) yes
C8 C9 C10 O10 175.(3) no
C8 C9 C10 C14 -69.(3) no
C8 C9 C10 C11 55.(3) no
O10 C10 C11 C12 169.5(2) no
C9 C10 C11 C12 -69.4(3) no
C14 C10 C11 C12 52.7(3) no
O1 C1 C12 C11 173.8(2) no
C2 C1 C12 C11 -69.2(3) no
C13 C1 C12 C11 55.9(3) no
C10 C11 C12 C1 146.8(2) yes
