#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/70/2207061.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_2207061
loop_
_publ_author_name
'Myint, Mo Aung'
'Blackman, Allan G.'
'Tan, Eng Wui'
_publ_section_title
;
 (+-)-Adamantane-1,2-diyl diacetate
;
_journal_coeditor_code           SG6027
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3154
_journal_page_last               o3155
_journal_paper_doi               10.1107/S1600536805027509
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H20 O4'
_chemical_formula_moiety         'C14 H20 O4'
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_chemical_name_common            adamantane-1,2-diacetate
_chemical_name_systematic
;
(+-)-adamantane-1,2-diyl diacetate
;
_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
_cell_angle_alpha                90.000
_cell_angle_beta                 102.934(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   8.699(5)
_cell_length_b                   12.618(5)
_cell_length_c                   11.835(5)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      33.31
_cell_measurement_theta_min      2.89
_cell_volume                     1266.1(10)
_computing_cell_refinement       'APEX-II and SAINT (Bruker, 2001)'
_computing_data_collection       'APEX-II (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.818
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26090
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.30
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular chip'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0334
_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)+(0.0517P)²+0.3507P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                3699
_reflns_number_total             3997
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg6027.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207061
_cod_database_fobs_code          2207061
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_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
_atom_site_type_symbol
O1 -0.25583(6) 0.01495(4) 0.81193(5) 0.01594(11) Uani d . 1 O
O2 -0.33618(6) 0.12926(4) 0.61053(5) 0.01474(11) Uani d . 1 O
C9 0.09378(8) 0.04534(6) 0.71586(6) 0.01481(14) Uani d . 1 C
H9 0.1582 -0.0110 0.6930 0.018 Uiso calc R 1 H
C11 0.06989(8) 0.24196(6) 0.74048(6) 0.01531(14) Uani d . 1 C
H11 0.1186 0.3108 0.7326 0.018 Uiso calc R 1 H
C1 -0.38855(8) 0.01489(6) 0.85309(6) 0.01675(14) Uani d . 1 C
O4 -0.28263(7) 0.14644(5) 0.43214(5) 0.02051(13) Uani d . 1 O
O3 -0.44730(8) 0.09334(5) 0.88291(6) 0.02790(15) Uani d . 1 O
C6 -0.18213(8) 0.11664(5) 0.80057(6) 0.01327(13) Uani d . 1 C
H6 -0.2452 0.1739 0.8231 0.016 Uiso calc R 1 H
C10 0.16906(8) 0.15341(6) 0.70285(7) 0.01673(14) Uani d . 1 C
H10A 0.1748 0.1641 0.6227 0.020 Uiso calc R 1 H
H10B 0.2755 0.1554 0.7504 0.020 Uiso calc R 1 H
C14 -0.07328(8) 0.04181(6) 0.63738(6) 0.01357(13) Uani d . 1 C
H14A -0.0679 0.0511 0.5570 0.016 Uiso calc R 1 H
H14B -0.1218 -0.0263 0.6449 0.016 Uiso calc R 1 H
C2 -0.45344(10) -0.09514(7) 0.85567(8) 0.02358(17) Uani d . 1 C
H2A -0.4908 -0.1046 0.9254 0.035 Uiso calc R 1 H
H2B -0.3719 -0.1459 0.8536 0.035 Uiso calc R 1 H
H2C -0.5391 -0.1053 0.7896 0.035 Uiso calc R 1 H
C12 -0.09753(8) 0.23938(6) 0.66314(6) 0.01427(13) Uani d . 1 C
H12A -0.1613 0.2945 0.6869 0.017 Uiso calc R 1 H
H12B -0.0932 0.2522 0.5831 0.017 Uiso calc R 1 H
C5 -0.17133(8) 0.13073(5) 0.67405(6) 0.01207(13) Uani d . 1 C
C8 0.08447(9) 0.02928(6) 0.84270(6) 0.01633(14) Uani d . 1 C
H8A 0.1897 0.0309 0.8921 0.020 Uiso calc R 1 H
H8B 0.0382 -0.0393 0.8516 0.020 Uiso calc R 1 H
C7 -0.01647(8) 0.11724(6) 0.87894(6) 0.01481(14) Uani d . 1 C
H7 -0.0234 0.1064 0.9596 0.018 Uiso calc R 1 H
C13 0.05908(8) 0.22556(6) 0.86704(7) 0.01679(14) Uani d . 1 C
H13A -0.0042 0.2814 0.8901 0.020 Uiso calc R 1 H
H13B 0.1637 0.2285 0.9173 0.020 Uiso calc R 1 H
C4 -0.55074(9) 0.14430(7) 0.45141(7) 0.02208(16) Uani d . 1 C
H4A -0.5800 0.2103 0.4122 0.033 Uiso calc R 1 H
H4B -0.6003 0.1385 0.5159 0.033 Uiso calc R 1 H
H4C -0.5843 0.0867 0.3987 0.033 Uiso calc R 1 H
C3 -0.37498(8) 0.14026(6) 0.49433(6) 0.01568(14) 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
C1 O1 C6 117.67(6)
C3 O2 C5 121.06(5)
C8 C9 C10 109.41(6)
C8 C9 C14 109.68(6)
C10 C9 C14 109.34(6)
C8 C9 H9 109.5
C10 C9 H9 109.5
C14 C9 H9 109.5
C13 C11 C10 110.21(6)
C13 C11 C12 108.73(6)
C10 C11 C12 109.30(6)
C13 C11 H11 109.5
C10 C11 H11 109.5
C12 C11 H11 109.5
O3 C1 O1 124.01(7)
O3 C1 C2 124.66(7)
O1 C1 C2 111.32(7)
O1 C6 C7 108.88(6)
O1 C6 C5 108.52(6)
C7 C6 C5 109.68(6)
O1 C6 H6 109.9
C7 C6 H6 109.9
C5 C6 H6 109.9
C9 C10 C11 109.69(6)
C9 C10 H10A 109.7
C11 C10 H10A 109.7
C9 C10 H10B 109.7
C11 C10 H10B 109.7
H10A C10 H10B 108.2
C5 C14 C9 108.57(6)
C5 C14 H14A 110.0
C9 C14 H14A 110.0
C5 C14 H14B 110.0
C9 C14 H14B 110.0
H14A C14 H14B 108.4
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C5 C12 C11 109.14(6)
C5 C12 H12A 109.9
C11 C12 H12A 109.9
C5 C12 H12B 109.9
C11 C12 H12B 109.9
H12A C12 H12B 108.3
O2 C5 C14 112.93(6)
O2 C5 C12 110.45(6)
C14 C5 C12 111.21(6)
O2 C5 C6 103.50(6)
C14 C5 C6 110.63(6)
C12 C5 C6 107.75(6)
C9 C8 C7 109.67(6)
C9 C8 H8A 109.7
C7 C8 H8A 109.7
C9 C8 H8B 109.7
C7 C8 H8B 109.7
H8A C8 H8B 108.2
C6 C7 C8 110.32(6)
C6 C7 C13 108.25(6)
C8 C7 C13 109.54(7)
C6 C7 H7 109.6
C8 C7 H7 109.6
C13 C7 H7 109.6
C11 C13 C7 109.27(6)
C11 C13 H13A 109.8
C7 C13 H13A 109.8
C11 C13 H13B 109.8
C7 C13 H13B 109.8
H13A C13 H13B 108.3
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O4 C3 O2 125.44(7)
O4 C3 C4 123.93(8)
O2 C3 C4 110.64(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3499(10)
O1 C6 1.4539(9)
O2 C3 1.3478(11)
O2 C5 1.4626(11)
C9 C8 1.5347(12)
C9 C10 1.5354(11)
C9 C14 1.5402(12)
C9 H9 0.9800
C11 C13 1.5358(12)
C11 C10 1.5372(11)
C11 C12 1.5373(12)
C11 H11 0.9800
C1 O3 1.2027(11)
C1 C2 1.5016(12)
O4 C3 1.2074(10)
C6 C7 1.5293(12)
C6 C5 1.5315(12)
C6 H6 0.9800
C10 H10A 0.9700
C10 H10B 0.9700
C14 C5 1.5299(10)
C14 H14A 0.9700
C14 H14B 0.9700
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C12 C5 1.5315(11)
C12 H12A 0.9700
C12 H12B 0.9700
C8 C7 1.5348(11)
C8 H8A 0.9700
C8 H8B 0.9700
C7 C13 1.5366(11)
C7 H7 0.9800
C13 H13A 0.9700
C13 H13B 0.9700
C4 C3 1.5002(13)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
