#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006271.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_2006271
loop_
_publ_author_name
'Rath, N. P.'
'Gu, H.'
'Murray, R. W.'
_publ_section_title
;
 1-Acetyl-3-hydroxyadamantane and 1-Carboxy-3-hydroxyadamantane
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              944
_journal_page_last               946
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_weight         196.24
_chemical_name_systematic
;
 ?
;
_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                 106.08(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.675(6)
_cell_length_b                   20.767(19)
_cell_length_c                   7.109(7)
_cell_measurement_reflns_used    17
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.965
_cell_measurement_theta_min      7.552
_cell_volume                     946.9(16)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1995)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '\w scans'
_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  0.0664
_diffrn_reflns_av_sigmaI/netI    0.1036
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3130
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        3.82
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_description       'Irregular plates'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.051
_refine_ls_goodness_of_fit_obs   1.201
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_restrained_S_obs      1.201
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_obs          0.0650
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.1598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1473
_refine_ls_wR_factor_obs         0.1138
_reflns_number_observed          969
_reflns_number_total             1856
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    bk1307.cif
_[local]_cod_data_source_block   5
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        946.9(15)
_cod_database_code               2006271
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_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 0.0562(15) 0.050(2) 0.0467(15) 0.0266(13) -0.0096(12) -0.0110(12)
O2 0.0407(15) 0.055(2) 0.0339(14) 0.0121(13) -0.0129(12) -0.0186(12)
O3 0.062(2) 0.059(2) 0.045(2) 0.0239(14) -0.0276(13) -0.0207(14)
C1 0.0259(14) 0.032(2) 0.025(2) 0.0056(13) -0.0002(13) -0.0053(14)
C2 0.033(2) 0.031(2) 0.034(2) 0.0043(14) -0.0009(15) -0.0025(14)
C3 0.032(2) 0.032(2) 0.027(2) 0.0054(14) -0.0019(14) -0.0052(14)
C4 0.029(2) 0.046(2) 0.040(2) 0.002(2) 0.002(2) -0.004(2)
C5 0.032(2) 0.050(2) 0.035(2) 0.009(2) 0.0077(15) -0.005(2)
C6 0.044(2) 0.037(2) 0.043(2) 0.015(2) -0.005(2) -0.007(2)
C7 0.043(2) 0.032(2) 0.041(2) -0.001(2) 0.002(2) 0.009(2)
C8 0.034(2) 0.034(2) 0.035(2) -0.0036(15) 0.0010(15) -0.004(2)
C9 0.041(2) 0.046(2) 0.028(2) 0.009(2) 0.0013(15) 0.007(2)
C10 0.040(2) 0.046(2) 0.029(2) 0.001(2) 0.006(2) 0.000(2)
C11 0.036(2) 0.037(2) 0.033(2) 0.003(2) 0.001(2) -0.004(2)
loop_
_atom_site_label
_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_occupancy
_atom_site_type_symbol
O1 0.6823(4) 0.02272(12) 1.3418(3) 0.0558(7) Uani d . 1 O
O2 0.0439(4) 0.05938(12) 0.7716(3) 0.0479(7) Uani d . 1 O
H2 0.123(7) 0.037(2) 0.739(6) 0.088(18) Uiso d . 1 H
O3 0.7011(4) 0.10522(13) 1.5351(4) 0.0641(9) Uani d . 1 O
H3 0.815(7) 0.084(2) 1.620(7) 0.109(17) Uiso d . 1 H
C1 0.4258(4) 0.10552(14) 1.2473(4) 0.0292(7) Uani d . 1 C
C2 0.3296(4) 0.06444(15) 1.0677(4) 0.0347(8) Uani d . 1 C
H2A 0.4315(4) 0.05684(15) 0.9959(4) 0.042 Uiso calc R 1 H
H2B 0.2877(4) 0.02311(15) 1.1079(4) 0.042 Uiso calc R 1 H
C3 0.1420(4) 0.09863(15) 0.9379(4) 0.0323(8) Uani d . 1 C
C4 -0.0178(5) 0.1101(2) 1.0465(5) 0.0398(9) Uani d . 1 C
H4A -0.0628(5) 0.0693(2) 1.0873(5) 0.048 Uiso calc R 1 H
H4B -0.1385(5) 0.1315(2) 0.9617(5) 0.048 Uiso calc R 1 H
C5 0.0766(5) 0.1517(2) 1.2245(5) 0.0395(8) Uani d . 1 C
H5 -0.0275(5) 0.1591(2) 1.2960(5) 0.047 Uiso calc R 1 H
C6 0.1425(5) 0.2148(2) 1.1602(5) 0.0444(9) Uani d . 1 C
H6A 0.2013(5) 0.2417(2) 1.2734(5) 0.053 Uiso calc R 1 H
H6B 0.0224(5) 0.2368(2) 1.0765(5) 0.053 Uiso calc R 1 H
C7 0.3020(5) 0.2037(2) 1.0503(5) 0.0406(9) Uani d . 1 C
H7 0.3444(5) 0.2451(2) 1.0076(5) 0.049 Uiso calc R 1 H
C8 0.4902(5) 0.17021(14) 1.1812(5) 0.0360(8) Uani d . 1 C
H8A 0.5515(5) 0.19687(14) 1.2945(5) 0.043 Uiso calc R 1 H
H8B 0.5938(5) 0.16361(14) 1.1107(5) 0.043 Uiso calc R 1 H
C9 0.2087(5) 0.1617(2) 0.8726(4) 0.0401(8) Uani d . 1 C
H9A 0.0896(5) 0.1833(2) 0.7860(4) 0.048 Uiso calc R 1 H
H9B 0.3112(5) 0.1544(2) 0.8012(4) 0.048 Uiso calc R 1 H
C10 0.2647(5) 0.1171(2) 1.3577(4) 0.0393(8) Uani d . 1 C
H10A 0.3247(5) 0.1431(2) 1.4729(4) 0.047 Uiso calc R 1 H
H10B 0.2213(5) 0.0763(2) 1.4002(4) 0.047 Uiso calc R 1 H
C11 0.6143(5) 0.0728(2) 1.3773(4) 0.0368(8) Uani d . 1 C
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
C3 O2 H2 113.(3) ?
C11 O3 H3 114.(3) ?
C11 C1 C10 110.3(3) ?
C11 C1 C2 110.5(3) ?
C10 C1 C2 109.1(3) ?
C11 C1 C8 109.2(2) ?
C10 C1 C8 108.7(3) ?
C2 C1 C8 109.0(3) ?
C3 C2 C1 109.5(3) ?
C3 C2 H2A 109.8(2) ?
C1 C2 H2A 109.8(2) ?
C3 C2 H2B 109.8(2) ?
C1 C2 H2B 109.8(2) ?
H2A C2 H2B 108.2 ?
O2 C3 C9 110.4(3) ?
O2 C3 C4 106.6(3) ?
C9 C3 C4 109.6(3) ?
O2 C3 C2 110.4(3) ?
C9 C3 C2 109.5(3) ?
C4 C3 C2 110.3(3) ?
C3 C4 C5 109.2(3) ?
C3 C4 H4A 109.8(2) ?
C5 C4 H4A 109.8(2) ?
C3 C4 H4B 109.8(2) ?
C5 C4 H4B 109.8(2) ?
H4A C4 H4B 108.3 ?
C6 C5 C4 109.5(3) ?
C6 C5 C10 109.9(3) ?
C4 C5 C10 109.3(3) ?
C6 C5 H5 109.4(2) ?
C4 C5 H5 109.4(2) ?
C10 C5 H5 109.4(2) ?
C5 C6 C7 109.6(3) ?
C5 C6 H6A 109.7(2) ?
C7 C6 H6A 109.7(2) ?
C5 C6 H6B 109.7(2) ?
C7 C6 H6B 109.7(2) ?
H6A C6 H6B 108.2 ?
C6 C7 C8 109.8(3) ?
C6 C7 C9 109.5(3) ?
C8 C7 C9 109.2(3) ?
C6 C7 H7 109.5(2) ?
C8 C7 H7 109.5(2) ?
C9 C7 H7 109.5(2) ?
C7 C8 C1 109.8(3) ?
C7 C8 H8A 109.7(2) ?
C1 C8 H8A 109.7(2) ?
C7 C8 H8B 109.7(2) ?
C1 C8 H8B 109.7(2) ?
H8A C8 H8B 108.2 ?
C3 C9 C7 109.4(3) ?
C3 C9 H9A 109.8(2) ?
C7 C9 H9A 109.8(2) ?
C3 C9 H9B 109.8(2) ?
C7 C9 H9B 109.8(2) ?
H9A C9 H9B 108.2 ?
C1 C10 C5 109.4(3) ?
C1 C10 H10A 109.8(2) ?
C5 C10 H10A 109.8(2) ?
C1 C10 H10B 109.8(2) ?
C5 C10 H10B 109.8(2) ?
H10A C10 H10B 108.2 ?
O1 C11 O3 122.1(3) yes
O1 C11 C1 124.7(3) yes
O3 C11 C1 113.3(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.190(4) yes
O2 C3 1.436(4) yes
O2 H2 0.79(4) ?
O3 C11 1.299(4) yes
O3 H3 0.93(5) ?
C1 C11 1.501(4) yes
C1 C10 1.516(4) ?
C1 C2 1.522(4) ?
C1 C8 1.524(4) ?
C2 C3 1.511(4) ?
C2 H2A 0.97 ?
C2 H2B 0.97 ?
C3 C9 1.499(4) ?
C3 C4 1.499(5) ?
C4 C5 1.517(4) ?
C4 H4A 0.97 ?
C4 H4B 0.97 ?
C5 C6 1.495(5) ?
C5 C10 1.526(4) ?
C5 H5 0.98 ?
C6 C7 1.503(5) ?
C6 H6A 0.97 ?
C6 H6B 0.97 ?
C7 C8 1.510(4) ?
C7 C9 1.518(4) ?
C7 H7 0.98 ?
C8 H8A 0.97 ?
C8 H8B 0.97 ?
C9 H9A 0.97 ?
C9 H9B 0.97 ?
C10 H10A 0.97 ?
C10 H10B 0.97 ?
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
C11 C1 C2 C3 -179.3(3)
C10 C1 C2 C3 59.3(3)
C8 C1 C2 C3 -59.3(3)
C1 C2 C3 O2 -177.6(3)
C1 C2 C3 C9 60.7(3)
C1 C2 C3 C4 -60.0(3)
O2 C3 C4 C5 -179.8(3)
C9 C3 C4 C5 -60.3(3)
C2 C3 C4 C5 60.3(3)
C3 C4 C5 C6 60.3(3)
C3 C4 C5 C10 -60.1(3)
C4 C5 C6 C7 -60.1(3)
C10 C5 C6 C7 59.9(3)
C5 C6 C7 C8 -60.2(3)
C5 C6 C7 C9 59.7(3)
C6 C7 C8 C1 60.2(3)
C9 C7 C8 C1 -59.9(4)
C11 C1 C8 C7 -180.0(3)
C10 C1 C8 C7 -59.6(3)
C2 C1 C8 C7 59.2(3)
O2 C3 C9 C7 177.2(3)
C4 C3 C9 C7 60.0(3)
C2 C3 C9 C7 -61.2(3)
C6 C7 C9 C3 -59.4(3)
C8 C7 C9 C3 60.8(4)
C11 C1 C10 C5 178.8(3)
C2 C1 C10 C5 -59.7(3)
C8 C1 C10 C5 59.1(3)
C6 C5 C10 C1 -59.9(4)
C4 C5 C10 C1 60.3(3)
C10 C1 C11 O1 122.8(4)
C2 C1 C11 O1 2.1(5)
C8 C1 C11 O1 -117.8(4)
C10 C1 C11 O3 -58.1(4)
C2 C1 C11 O3 -178.8(3)
C8 C1 C11 O3 61.3(4)