#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/83/2208379.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_2208379
loop_
_publ_author_name
'Mo Aung Myint'
'Price, Jason R.'
'Eng Wui Tan'
_publ_section_title
;
 Adamantane-1,2-diol
;
_journal_coeditor_code           LH6588
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1139
_journal_page_last               o1140
_journal_paper_doi               10.1107/S1600536806003734
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H16 O2'
_chemical_formula_moiety         'C10 H16 O2'
_chemical_formula_sum            'C10 H16 O2'
_chemical_formula_weight         168.23
_chemical_name_systematic
;
adamantane-1,2-diol
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.6159(3)
_cell_length_b                   20.6781(7)
_cell_length_c                   8.3921(2)
_cell_measurement_reflns_used    2252
_cell_measurement_temperature    83(2)
_cell_measurement_theta_max      32.63
_cell_measurement_theta_min      3.37
_cell_volume                     1668.67(9)
_computing_cell_refinement       'APEXII and SAINT (Bruker  2004)'
_computing_data_collection       'APEXII (Bruker 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and POV-Ray (Persistence of Vision,
2004)
;
_computing_publication_material  'enCIFer (Allen et al.,  2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      83(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker Kappa-APEX-II area-detector'
_diffrn_measurement_method       'φ and ω '
_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  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            41081
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         32.70
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.369
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0791P)²+1.9937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1758
_reflns_number_gt                2252
_reflns_number_total             2845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6588.cif
_cod_data_source_block           I
_cod_database_code               2208379
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
O O1 -0.13529(11) 0.53630(5) 0.09461(12) 0.0133(2) Uani d . 1
H H1A -0.2032 0.5204 0.1438 0.020 Uiso calc R 1
O O2 0.13649(12) 0.51341(5) 0.22384(13) 0.0182(3) Uani d . 1
H H2A 0.1086 0.5052 0.1312 0.027 Uiso calc R 1
C C1 -0.06880(14) 0.58392(6) 0.19276(15) 0.0095(2) Uani d . 1
C C2 0.03234(15) 0.55025(7) 0.30695(16) 0.0134(3) Uani d . 1
H H2B -0.0214 0.5206 0.3782 0.016 Uiso calc R 1
C C3 0.10813(15) 0.60078(7) 0.41011(16) 0.0146(3) Uani d . 1
H H3A 0.1749 0.5786 0.4833 0.017 Uiso calc R 1
C C4 0.18742(16) 0.64722(8) 0.30032(18) 0.0173(3) Uani d . 1
H H4A 0.2563 0.6227 0.2367 0.021 Uiso calc R 1
H H4B 0.2382 0.6795 0.3653 0.021 Uiso calc R 1
C C5 0.08549(16) 0.68195(7) 0.18849(17) 0.0163(3) Uani d . 1
H H5A 0.1376 0.7126 0.1184 0.020 Uiso calc R 1
C C6 -0.02213(17) 0.71906(7) 0.28638(18) 0.0179(3) Uani d . 1
H H6A -0.0885 0.7409 0.2140 0.021 Uiso calc R 1
H H6B 0.0250 0.7526 0.3509 0.021 Uiso calc R 1
C C7 -0.10082(15) 0.67278(7) 0.39624(17) 0.0144(3) Uani d . 1
H H7A -0.1707 0.6974 0.4604 0.017 Uiso calc R 1
C C8 0.00006(16) 0.63765(7) 0.50756(17) 0.0155(3) Uani d . 1
H H8A 0.0472 0.6694 0.5773 0.019 Uiso calc R 1
H H8B -0.0520 0.6071 0.5760 0.019 Uiso calc R 1
C C9 0.01004(15) 0.63076(7) 0.08472(16) 0.0148(3) Uani d . 1
H H9A -0.0558 0.6524 0.0114 0.018 Uiso calc R 1
H H9B 0.0788 0.6067 0.0199 0.018 Uiso calc R 1
C C10 -0.17528(15) 0.62165(7) 0.29281(17) 0.0140(3) Uani d . 1
H H10A -0.2271 0.5914 0.3622 0.017 Uiso calc R 1
H H10B -0.2428 0.6432 0.2214 0.017 Uiso calc R 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
C1 O1 H1A 109.5
C2 O2 H2A 109.5
O1 C1 C9 108.40(10)
O1 C1 C2 109.27(10)
C9 C1 C2 110.13(11)
O1 C1 C10 111.43(11)
C9 C1 C10 109.45(11)
C2 C1 C10 108.17(10)
O2 C2 C1 112.28(10)
O2 C2 C3 107.60(11)
C1 C2 C3 110.09(11)
O2 C2 H2B 108.9
C1 C2 H2B 108.9
C3 C2 H2B 108.9
C8 C3 C4 110.34(12)
C8 C3 C2 108.53(12)
C4 C3 C2 108.80(11)
C8 C3 H3A 109.7
C4 C3 H3A 109.7
C2 C3 H3A 109.7
C3 C4 C5 110.04(12)
C3 C4 H4A 109.7
C5 C4 H4A 109.7
C3 C4 H4B 109.7
C5 C4 H4B 109.7
H4A C4 H4B 108.2
C6 C5 C4 109.80(12)
C6 C5 C9 109.14(12)
C4 C5 C9 108.82(12)
C6 C5 H5A 109.7
C4 C5 H5A 109.7
C9 C5 H5A 109.7
C5 C6 C7 110.18(12)
C5 C6 H6A 109.6
C7 C6 H6A 109.6
C5 C6 H6B 109.6
C7 C6 H6B 109.6
H6A C6 H6B 108.1
C6 C7 C8 110.58(12)
C6 C7 C10 108.60(12)
C8 C7 C10 108.19(11)
C6 C7 H7A 109.8
C8 C7 H7A 109.8
C10 C7 H7A 109.8
C3 C8 C7 109.98(11)
C3 C8 H8A 109.7
C7 C8 H8A 109.7
C3 C8 H8B 109.7
C7 C8 H8B 109.7
H8A C8 H8B 108.2
C1 C9 C5 109.36(11)
C1 C9 H9A 109.8
C5 C9 H9A 109.8
C1 C9 H9B 109.8
C5 C9 H9B 109.8
H9A C9 H9B 108.2
C1 C10 C7 110.23(11)
C1 C10 H10A 109.6
C7 C10 H10A 109.6
C1 C10 H10B 109.6
C7 C10 H10B 109.6
H10A C10 H10B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4343(15)
O1 H1A 0.8400
O2 C2 1.4387(17)
O2 H2A 0.8400
C1 C9 1.5279(18)
C1 C2 1.5327(19)
C1 C10 1.5369(19)
C2 C3 1.540(2)
C2 H2B 1.0000
C3 C8 1.526(2)
C3 C4 1.534(2)
C3 H3A 1.0000
C4 C5 1.535(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.528(2)
C5 C9 1.551(2)
C5 H5A 1.0000
C6 C7 1.529(2)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.530(2)
C7 C10 1.544(2)
C7 H7A 1.0000
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
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 H2A O1 . 0.84 2.45 2.8688(15) 112
O1 H1A O2 4_465 0.84 2.02 2.8625(15) 176
O2 H2A O1 5_565 0.84 2.10 2.8633(14) 152
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 58.47(14)
C9 C1 C2 O2 -60.49(14)
C10 C1 C2 O2 179.94(11)
O1 C1 C2 C3 178.32(11)
C9 C1 C2 C3 59.36(14)
C10 C1 C2 C3 -60.21(14)
O2 C2 C3 C8 -176.45(11)
C1 C2 C3 C8 60.90(14)
O2 C2 C3 C4 63.46(14)
C1 C2 C3 C4 -59.19(14)
C8 C3 C4 C5 -58.53(15)
C2 C3 C4 C5 60.44(15)
C3 C4 C5 C6 58.54(16)
C3 C4 C5 C9 -60.85(15)
C4 C5 C6 C7 -58.44(16)
C9 C5 C6 C7 60.76(15)
C5 C6 C7 C8 58.37(15)
C5 C6 C7 C10 -60.20(15)
C4 C3 C8 C7 57.96(15)
C2 C3 C8 C7 -61.17(15)
C6 C7 C8 C3 -57.91(15)
C10 C7 C8 C3 60.90(15)
O1 C1 C9 C5 -178.82(11)
C2 C1 C9 C5 -59.32(14)
C10 C1 C9 C5 59.47(14)
C6 C5 C9 C1 -60.02(14)
C4 C5 C9 C1 59.79(15)
O1 C1 C10 C7 -179.64(10)
C9 C1 C10 C7 -59.76(14)
C2 C1 C10 C7 60.24(14)
C6 C7 C10 C1 59.48(14)
C8 C7 C10 C1 -60.59(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10287761
