#------------------------------------------------------------------------------
#$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/56/2005677.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_2005677
loop_
_publ_author_name
'Vaissermann, J.'
'Lomas, J. S.'
_publ_section_title
;
 A Highly Strained Tertiary Acetate: 2,2'-Spirobiadamant-1-yl Acetate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2837
_journal_page_last               2839
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C21 H30 O2'
_chemical_formula_structural     'C21 H30 O2'
_chemical_formula_sum            'C21 H30 O2'
_chemical_formula_weight         314.47
_chemical_melting_point          127
_chemical_name_systematic
;
2,2'-spirobitricyclo[3.3.1.1^3,7^]decanyl acetate
;
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 98.78(3)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   7.267(2)
_cell_length_b                   17.837(7)
_cell_length_c                   12.975(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      11
_cell_volume                     1662.1(12)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'CRYSTALS (Watkin, Carruthers & Bettridge, 1988)'
_computing_molecular_graphics    'CAMERON (Pearce, Watkin & Prout, 1992)'
_computing_publication_material  CRYSTALS
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3290
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.26
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.61
_refine_ls_extinction_coef       167(10)
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_obs   3.55
_refine_ls_hydrogen_treatment    'refxyz and one overall U~iso~ parameter'
_refine_ls_number_parameters     300
_refine_ls_number_reflns         1972
_refine_ls_R_factor_obs          0.0422
_refine_ls_shift/esd_max         0.41
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.0405
_reflns_number_observed          1972
_reflns_number_total             2931
_reflns_observed_criterion       F^2^>3\s(F)^2^
_[local]_cod_data_source_file    pa1240.cif
_[local]_cod_data_source_block   lomas4
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1662.1(1.2)
_cod_database_code               2005677
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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
O(1) 0.0921(2) 0.6358(1) 0.8014(1) 0.0383
O(2) 0.3032(3) 0.7306(1) 0.8220(2) 0.0598
C(1) -0.0274(3) 0.6624(1) 0.7066(2) 0.0344
C(2) -0.1791(3) 0.5997(1) 0.6753(2) 0.0301
C(3) -0.2996(4) 0.6335(2) 0.5748(2) 0.0386
C(4) -0.3905(4) 0.7077(2) 0.5971(2) 0.0455
C(5) -0.2397(4) 0.7658(2) 0.6322(2) 0.0475
C(6) -0.1220(4) 0.7775(2) 0.5459(2) 0.0483
C(7) -0.0329(4) 0.7034(2) 0.5216(2) 0.0439
C(8) 0.0893(4) 0.6748(2) 0.6194(2) 0.0393
C(9) -0.1173(4) 0.7366(1) 0.7301(2) 0.0399
C(10) -0.1845(4) 0.6459(2) 0.4870(2) 0.0427
C(11) -0.3057(3) 0.5833(1) 0.7600(2) 0.0359
C(12) -0.4675(4) 0.5317(2) 0.7140(2) 0.0434
C(13) -0.3919(4) 0.4572(2) 0.6814(2) 0.0474
C(14) -0.2886(4) 0.4181(2) 0.7778(3) 0.0492
C(15) -0.1273(4) 0.4682(2) 0.8270(2) 0.0445
C(16) 0.0034(4) 0.4813(2) 0.7464(2) 0.0416
C(17) -0.0982(4) 0.5217(1) 0.6502(2) 0.0381
C(18) -0.2033(4) 0.5434(2) 0.8569(2) 0.0381
C(19) -0.2580(4) 0.4691(2) 0.6026(2) 0.0456
C(20) 0.2436(4) 0.6725(2) 0.8500(2) 0.0426
C(21) 0.3257(5) 0.6300(2) 0.9430(2) 0.0520
H(31) -0.394(4) 0.597(2) 0.548(2) 0.052(1)
H(41) -0.461(4) 0.703(2) 0.649(2) 0.052(1)
H(42) -0.468(4) 0.725(1) 0.530(2) 0.052(1)
H(51) -0.294(4) 0.814(2) 0.654(2) 0.052(1)
H(61) -0.030(4) 0.816(2) 0.569(2) 0.052(1)
H(62) -0.195(4) 0.798(1) 0.481(2) 0.052(1)
H(71) 0.044(4) 0.712(1) 0.462(2) 0.052(1)
H(81) 0.147(4) 0.629(2) 0.606(2) 0.052(1)
H(82) 0.175(4) 0.711(2) 0.645(2) 0.052(1)
H(91) -0.183(4) 0.732(2) 0.788(2) 0.052(1)
H(92) -0.025(4) 0.771(2) 0.756(2) 0.052(1)
H(101) -0.132(4) 0.595(2) 0.463(2) 0.052(1)
H(102) -0.261(4) 0.665(2) 0.427(2) 0.052(1)
H(111) -0.356(4) 0.631(2) 0.784(2) 0.052(1)
H(121) -0.541(4) 0.525(1) 0.774(2) 0.052(1)
H(122) -0.541(4) 0.556(2) 0.656(2) 0.052(1)
H(131) -0.486(4) 0.426(2) 0.647(2) 0.052(1)
H(141) -0.367(4) 0.411(1) 0.832(2) 0.052(1)
H(142) -0.242(4) 0.369(2) 0.757(2) 0.052(1)
H(151) -0.057(4) 0.444(1) 0.894(2) 0.052(1)
H(161) 0.110(4) 0.510(2) 0.779(2) 0.052(1)
H(162) 0.043(4) 0.432(2) 0.720(2) 0.052(1)
H(171) -0.016(4) 0.528(1) 0.596(2) 0.052(1)
H(181) -0.282(4) 0.534(1) 0.906(2) 0.052(1)
H(182) -0.102(4) 0.575(2) 0.897(2) 0.052(1)
H(191) -0.317(4) 0.489(2) 0.536(2) 0.052(1)
H(192) -0.203(4) 0.420(2) 0.585(2) 0.052(1)
H(211) 0.279(4) 0.575(2) 0.944(2) 0.052(1)
H(212) 0.289(4) 0.649(2) 0.996(2) 0.052(1)
H(213) 0.446(4) 0.638(2) 0.961(2) 0.052(1)
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
O(1) 0.0355(9) 0.0430(10) 0.0370(10) -0.0054(8) 0.0001(8) 0.0020(8)
O(2) 0.0630(10) 0.0610(10) 0.0680(10) -0.0260(10) -0.0080(10) 0.0100(10)
C(1) 0.0350(10) 0.0360(10) 0.0320(10) -0.0010(10) 0.0030(10) 0.0010(10)
C(2) 0.0310(10) 0.0310(10) 0.0290(10) 0.0000(10) 0.0070(10) -0.0010(10)
C(3) 0.0360(10) 0.0420(10) 0.038(2) -0.0050(10) 0.0010(10) 0.0040(10)
C(4) 0.040(2) 0.051(2) 0.049(2) 0.0080(10) 0.0060(10) 0.0110(10)
C(5) 0.056(2) 0.036(2) 0.056(2) 0.0100(10) 0.0090(10) 0.0040(10)
C(6) 0.060(2) 0.043(2) 0.048(2) -0.0070(10) 0.0040(10) 0.0130(10)
C(7) 0.049(2) 0.053(2) 0.037(2) -0.0070(10) 0.0130(10) 0.0060(10)
C(8) 0.0360(10) 0.043(2) 0.042(2) -0.0060(10) 0.0120(10) 0.0000(10)
C(9) 0.049(2) 0.0330(10) 0.040(2) -0.0030(10) 0.0090(10) -0.0030(10)
C(10) 0.051(2) 0.049(2) 0.0310(10) -0.0050(10) 0.0020(10) 0.0030(10)
C(11) 0.0350(10) 0.0370(10) 0.0380(10) 0.0020(10) 0.0110(10) 0.0000(10)
C(12) 0.0340(10) 0.056(2) 0.046(2) -0.0050(10) 0.0070(10) 0.0070(10)
C(13) 0.051(2) 0.045(2) 0.053(2) -0.0180(10) 0.0020(10) -0.0030(10)
C(14) 0.061(2) 0.037(2) 0.057(2) -0.0100(10) 0.009(2) 0.0050(10)
C(15) 0.051(2) 0.039(2) 0.044(2) 0.0000(10) 0.0020(10) 0.0070(10)
C(16) 0.042(2) 0.0330(10) 0.053(2) 0.0060(10) 0.0070(10) -0.0040(10)
C(17) 0.0400(10) 0.0380(10) 0.0390(10) 0.0000(10) 0.0100(10) -0.0050(10)
C(18) 0.043(2) 0.043(2) 0.0340(10) -0.0030(10) 0.0120(10) 0.0030(10)
C(19) 0.055(2) 0.041(2) 0.043(2) -0.0050(10) 0.0040(10) -0.0090(10)
C(20) 0.0410(10) 0.047(2) 0.040(2) -0.0060(10) 0.0030(10) -0.0030(10)
C(21) 0.046(2) 0.068(2) 0.045(2) -0.007(2) -0.0030(10) -0.001(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
'C   ' 0.0020 0.0020
'H   ' 0.0000 0.0000
'O   ' 0.0080 0.0060
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
C(1) O(1) C(20) 124.6(2) no
O(1) C(1) C(2) 106.6(2) no
O(1) C(1) C(8) 110.0(2) no
C(2) C(1) C(8) 110.8(2) no
O(1) C(1) C(9) 109.2(2) no
C(2) C(1) C(9) 111.2(2) no
C(8) C(1) C(9) 109.0(2) no
C(1) C(2) C(3) 102.7(2) yes
C(1) C(2) C(11) 114.4(2) yes
C(3) C(2) C(11) 109.9(2) yes
C(1) C(2) C(17) 114.4(2) yes
C(3) C(2) C(17) 110.3(2) yes
C(11) C(2) C(17) 105.1(2) yes
C(2) C(3) C(4) 112.1(2) no
C(2) C(3) C(10) 112.0(2) no
C(4) C(3) C(10) 108.5(2) no
C(2) C(3) H(31) 108.3(16) no
C(4) C(3) H(31) 110.1(16) no
C(10) C(3) H(31) 105.7(16) no
C(3) C(4) C(5) 109.5(2) no
C(3) C(4) H(41) 111.2(18) no
C(5) C(4) H(41) 107.7(18) no
C(3) C(4) H(42) 107.7(15) no
C(5) C(4) H(42) 108.9(15) no
H(41) C(4) H(42) 112.(2) no
C(4) C(5) C(6) 109.4(3) no
C(4) C(5) C(9) 108.5(2) no
C(6) C(5) C(9) 109.7(2) no
C(4) C(5) H(51) 111.5(15) no
C(6) C(5) H(51) 112.4(15) no
C(9) C(5) H(51) 105.3(15) no
C(5) C(6) C(7) 109.6(2) no
C(5) C(6) H(61) 108.0(16) no
C(7) C(6) H(61) 112.2(16) no
C(5) C(6) H(62) 112.7(15) no
C(7) C(6) H(62) 109.3(16) no
H(61) C(6) H(62) 105.(2) no
C(6) C(7) C(8) 109.3(2) no
C(6) C(7) C(10) 109.5(2) no
C(8) C(7) C(10) 108.9(2) no
C(6) C(7) H(71) 109.1(15) no
C(8) C(7) H(71) 111.3(14) no
C(10) C(7) H(71) 108.7(15) no
C(1) C(8) C(7) 110.3(2) no
C(1) C(8) H(81) 108.7(17) no
C(7) C(8) H(81) 110.7(17) no
C(1) C(8) H(82) 104.3(17) no
C(7) C(8) H(82) 109.9(17) no
H(81) C(8) H(82) 113.(2) no
C(1) C(9) C(5) 110.0(2) no
C(1) C(9) H(91) 111.6(17) no
C(5) C(9) H(91) 112.5(16) no
C(1) C(9) H(92) 109.7(17) no
C(5) C(9) H(92) 111.9(17) no
H(91) C(9) H(92) 101.(2) no
C(3) C(10) C(7) 109.4(2) no
C(3) C(10) H(101) 111.6(15) no
C(7) C(10) H(101) 112.6(14) no
C(3) C(10) H(102) 110.1(17) no
C(7) C(10) H(102) 107.5(17) no
H(101) C(10) H(102) 105.(2) no
C(2) C(11) C(12) 109.6(2) no
C(2) C(11) C(18) 113.5(2) no
C(12) C(11) C(18) 106.6(2) no
C(2) C(11) H(111) 110.0(15) no
C(12) C(11) H(111) 109.9(15) no
C(18) C(11) H(111) 107.2(15) no
C(11) C(12) C(13) 110.1(2) no
C(11) C(12) H(121) 103.5(15) no
C(13) C(12) H(121) 111.4(15) no
C(11) C(12) H(122) 109.9(17) no
C(13) C(12) H(122) 110.9(17) no
H(121) C(12) H(122) 111.(2) no
C(12) C(13) C(14) 108.9(3) no
C(12) C(13) C(19) 111.0(2) no
C(14) C(13) C(19) 109.1(3) no
C(12) C(13) H(131) 112.7(16) no
C(14) C(13) H(131) 109.8(16) no
C(19) C(13) H(131) 105.1(16) no
C(13) C(14) C(15) 108.9(2) no
C(13) C(14) H(141) 112.2(16) no
C(15) C(14) H(141) 105.4(16) no
C(13) C(14) H(142) 109.2(16) no
C(15) C(14) H(142) 111.1(16) no
H(141) C(14) H(142) 110.(2) no
C(14) C(15) C(16) 108.5(2) no
C(14) C(15) C(18) 109.6(2) no
C(16) C(15) C(18) 109.0(2) no
C(14) C(15) H(151) 110.5(15) no
C(16) C(15) H(151) 111.1(15) no
C(18) C(15) H(151) 108.1(15) no
C(15) C(16) C(17) 110.9(2) no
C(15) C(16) H(161) 108.6(16) no
C(17) C(16) H(161) 110.8(16) no
C(15) C(16) H(162) 109.5(15) no
C(17) C(16) H(162) 105.3(15) no
H(161) C(16) H(162) 112.(2) no
C(2) C(17) C(16) 113.5(2) no
C(2) C(17) C(19) 109.9(2) no
C(16) C(17) C(19) 106.2(2) no
C(2) C(17) H(171) 109.5(15) no
C(16) C(17) H(171) 111.3(15) no
C(19) C(17) H(171) 106.2(15) no
C(11) C(18) C(15) 110.5(2) no
C(11) C(18) H(181) 111.8(16) no
C(15) C(18) H(181) 107.8(17) no
C(11) C(18) H(182) 113.3(15) no
C(15) C(18) H(182) 110.6(15) no
H(181) C(18) H(182) 103.(2) no
C(13) C(19) C(17) 109.4(2) no
C(13) C(19) H(191) 114.0(16) no
C(17) C(19) H(191) 109.7(16) no
C(13) C(19) H(192) 110.7(16) no
C(17) C(19) H(192) 108.6(15) no
H(191) C(19) H(192) 104.(2) no
O(1) C(20) O(2) 125.7(2) no
O(1) C(20) C(21) 109.4(2) no
O(2) C(20) C(21) 124.9(3) no
C(20) C(21) H(211) 113.9(15) no
C(20) C(21) H(212) 109.(2) no
H(211) C(21) H(212) 103.(3) no
C(20) C(21) H(213) 113.8(18) no
H(211) C(21) H(213) 117.(2) no
H(212) C(21) H(213) 98.(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.472(3) no
O(1) C(20) 1.351(3) no
O(2) C(20) 1.201(3) no
C(1) C(2) 1.580(3) yes
C(1) C(8) 1.530(3) no
C(1) C(9) 1.526(3) no
C(2) C(3) 1.575(3) yes
C(2) C(11) 1.565(3) yes
C(2) C(17) 1.564(3) yes
C(3) C(4) 1.528(4) no
C(3) C(10) 1.529(4) no
C(3) H(31) 0.97(3) no
C(4) C(5) 1.526(4) no
C(4) H(41) 0.91(3) no
C(4) H(42) 1.02(3) no
C(5) C(6) 1.524(4) no
C(5) C(9) 1.526(4) no
C(5) H(51) 1.00(3) no
C(6) C(7) 1.527(4) no
C(6) H(61) 0.97(3) no
C(6) H(62) 1.00(3) no
C(7) C(8) 1.522(4) no
C(7) C(10) 1.521(4) no
C(7) H(71) 1.03(3) no
C(8) H(81) 0.95(3) no
C(8) H(82) 0.93(3) no
C(9) H(91) 0.95(3) no
C(9) H(92) 0.93(3) no
C(10) H(101) 1.05(3) no
C(10) H(102) 0.94(3) no
C(11) C(12) 1.540(4) no
C(11) C(18) 1.534(4) no
C(11) H(111) 1.00(3) no
C(12) C(13) 1.522(4) no
C(12) H(121) 1.02(3) no
C(12) H(122) 0.95(3) no
C(13) C(14) 1.526(4) no
C(13) C(19) 1.530(4) no
C(13) H(131) 0.94(3) no
C(14) C(15) 1.533(4) no
C(14) H(141) 0.98(3) no
C(14) H(142) 0.99(3) no
C(15) C(16) 1.534(4) no
C(15) C(18) 1.523(4) no
C(15) H(151) 1.04(3) no
C(16) C(17) 1.531(4) no
C(16) H(161) 0.97(3) no
C(16) H(162) 1.01(3) no
C(17) C(19) 1.546(4) no
C(17) H(171) 1.00(3) no
C(18) H(181) 0.94(3) no
C(18) H(182) 1.00(3) no
C(19) H(191) 0.97(3) no
C(19) H(192) 1.00(3) no
C(20) C(21) 1.472(4) no
C(21) H(211) 1.04(3) no
C(21) H(212) 0.85(3) no
C(21) H(213) 0.88(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
O(1) O(2) 2.271(2) no
O(1) C(2) 2.448(3) no
O(1) C(3) 3.768(3) no
O(1) C(5) 3.794(3) no
O(1) C(7) 3.802(3) no
O(1) C(8) 2.459(3) no
O(1) C(9) 2.444(3) no
O(1) C(11) 3.008(3) no
O(1) C(15) 3.428(3) no
O(1) C(16) 2.894(3) no
O(1) C(17) 3.013(3) no
O(1) C(18) 2.883(3) no
O(1) C(21) 2.305(3) no
O(1) H(81) 2.63(3) no
O(1) H(82) 2.58(3) no
O(1) H(91) 2.62(3) no
O(1) H(92) 2.59(3) no
O(1) H(111) 3.23(3) no
O(1) H(151) 3.84(3) no
O(1) H(161) 2.26(3) yes
O(1) H(162) 3.80(3) no
O(1) H(171) 3.29(3) no
O(1) H(181) 3.69(3) no
O(1) H(182) 2.29(3) yes
O(1) H(211) 2.38(3) no
O(1) H(212) 2.72(3) no
O(1) H(213) 3.05(3) no
O(2) C(1) 2.898(3) no
O(2) C(8) 3.012(3) no
O(2) C(9) 3.108(3) no
O(2) C(21) 2.373(4) no
O(2) H(81) 3.39(3) no
O(2) H(82) 2.36(3) yes
O(2) H(91) 3.49(3) no
O(2) H(92) 2.51(3) yes
O(2) H(211) 3.21(3) no
O(2) H(212) 2.70(3) no
O(2) H(213) 2.55(3) no
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
C(2) C(1) O(1) C(20) 177.1(2) yes
C(1) O(1) C(20) O(2) -1.4(2) yes
C(1) O(1) C(20) C(21) 178.9(2) yes
C(9) C(1) O(1) C(20) -62.67 no
C(8) C(1) O(1) C(20) 56.86 no
C(3) C(2) C(1) O(1) 179.54 no
C(5) C(9) C(1) O(1) 179.17 no
C(7) C(8) C(1) O(1) -179.19 no
C(11) C(2) C(1) O(1) 60.42 no
C(17) C(2) C(1) O(1) -60.93 no