#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/15/2101558.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_2101558
loop_
_publ_author_name
'Yufit, D. S.'
'Mallinson, P. R.'
'Muir, K. W.'
'Kozhushkov, S. I.'
'De Meijere, A.'
_publ_section_title
;
 Experimental charge density study of 7-dispiro[2.0.2.1]heptane
 carboxylic acid
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              668
_journal_page_last               676
_journal_paper_doi               10.1107/S010876819600105X
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C8 H10 O2'
_chemical_formula_sum            'C8 H10 O2'
_chemical_formula_weight         138.17
_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           'Clementi & Roetti (1974)'
_cell_angle_alpha                90
_cell_angle_beta                 103.780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3860(10)
_cell_length_b                   11.2640(10)
_cell_length_c                   10.1050(10)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      19
_cell_volume                     705.95(15)
_diffrn_measurement_device       'Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11899
_diffrn_reflns_theta_max         50
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  '120 min'
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   'Not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.14
_refine_diff_density_min         -13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.52
_refine_ls_hydrogen_treatment    'See text'
_refine_ls_number_parameters     135
_refine_ls_number_reflns         5539
_refine_ls_R_factor_obs          0.0377
_refine_ls_shift/esd_max         0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      '\S w(|F~o~| - k|F~c~|^2^'
_refine_ls_wR_factor_obs         0.0472
_reflns_number_observed          5539
_reflns_number_total             7085
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            ha0142.cif
_cod_data_source_block           1
_cod_original_cell_volume        706.00(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2101558
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(1) 0.62988(5) 0.96561(3) 0.16458(4) 0.016
O(2) 0.64329(5) 0.87544(3) -0.03067(3) 0.017
C(1) 1.26751(4) 0.75054(3) 0.18035(3) 0.017
C(2) 1.16180(4) 0.79982(3) 0.03900(3) 0.018
C(3) 1.03018(4) 0.74961(2) 0.12744(2) 0.012
C(4) 0.85055(4) 0.66975(2) 0.11774(2) 0.012
C(5) 0.80856(5) 0.54807(2) 0.16041(3) 0.017
C(6) 0.70452(5) 0.59415(2) 0.01723(3) 0.017
C(7) 0.83667(4) 0.79125(2) 0.17846(2) 0.012
C(8) 0.69426(4) 0.88241(2) 0.09865(2) 0.011
H(1O) 0.53100 1.02496 0.10488 0.030
H(2O) 0.52812 0.93436 -0.07569 0.029
H(11) 1.34838 0.66441 0.18416 0.032
H(12) 1.33682 0.81444 0.26043 0.031
H(21) 1.17850 0.74839 -0.04998 0.025
H(22) 1.15805 0.89598 0.02221 0.032
H(51) 0.94116 0.48443 0.17200 0.027
H(52) 0.71001 0.53869 0.23487 0.025
H(61) 0.76167 0.55836 -0.06864 0.024
H(62) 0.53078 0.61130 -0.00568 0.029
H(7) 0.85300 0.79998 0.28844 0.022
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(8) O(1) H(1O) 114.00(10)
C(8) O(2) H(2O) 113.70(10)
C(2) C(1) C(3) 58.70(10)
C(2) C(1) H(11) 117.00(10)
C(2) C(1) H(12) 117.50(10)
C(3) C(1) H(11) 116.10(10)
C(3) C(1) H(12) 118.00(10)
H(11) C(1) H(12) 116.90(10)
C(1) C(2) C(3) 59.00(10)
C(1) C(2) H(21) 117.80(10)
C(1) C(2) H(22) 119.40(10)
C(3) C(2) H(21) 118.30(10)
C(3) C(2) H(22) 118.50(10)
H(21) C(2) H(22) 113.50(10)
C(1) C(3) C(2) 62.30(10)
C(1) C(3) C(4) 139.20(10)
C(1) C(3) C(7) 135.90(10)
C(2) C(3) C(4) 139.10(10)
C(2) C(3) C(7) 135.40(10)
C(4) C(3) C(7) 61.20(10)
C(3) C(4) C(5) 138.90(10)
C(3) C(4) C(6) 140.30(10)
C(3) C(4) C(7) 62.00(10)
C(5) C(4) C(6) 62.40(10)
C(5) C(4) C(7) 133.50(10)
C(6) C(4) C(7) 135.60(10)
C(4) C(5) C(6) 58.60(10)
C(4) C(5) H(51) 116.60(10)
C(4) C(5) H(52) 117.60(10)
C(6) C(5) H(51) 118.30(10)
C(6) C(5) H(52) 119.40(10)
H(51) C(5) H(52) 114.80(10)
C(4) C(6) C(5) 59.00(10)
C(4) C(6) H(61) 118.90(10)
C(4) C(6) H(62) 119.10(10)
C(5) C(6) H(61) 118.20(10)
C(5) C(6) H(62) 116.70(10)
H(61) C(6) H(62) 114.20(10)
C(3) C(7) C(4) 56.80(10)
C(3) C(7) C(8) 118.20(10)
C(3) C(7) H(7) 118.90(10)
C(4) C(7) C(8) 119.70(10)
C(4) C(7) H(7) 119.50(10)
C(8) C(7) H(7) 112.90(10)
O(1) C(8) O(2) 123.20(10)
O(1) C(8) C(7) 117.40(10)
O(2) C(8) C(7) 119.40(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(1) C(8) 1.2730(10)
O(1) H(1O) 1.0140(10)
O(2) C(8) 1.2720(10)
O(2) H(2O) 1.0140(10)
C(1) C(2) 1.5310(10)
C(1) C(3) 1.4820(10)
C(1) H(11) 1.0950(10)
C(1) H(12) 1.0950(10)
C(2) C(3) 1.4770(10)
C(2) H(21) 1.0960(10)
C(2) H(22) 1.0960(10)
C(3) C(4) 1.4430(10)
C(3) C(7) 1.5220(10)
C(4) C(5) 1.4800(10)
C(4) C(6) 1.4750(10)
C(4) C(7) 1.5110(10)
C(5) C(6) 1.5320(10)
C(5) H(51) 1.0940(10)
C(5) H(52) 1.0950(10)
C(6) H(61) 1.0950(10)
C(6) H(62) 1.0950(10)
C(7) C(8) 1.4770(10)
C(7) H(7) 1.0960(10)
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
H(1O) O(1) C(8) O(2) 1.40(10)
H(1O) O(1) C(8) C(7) -179.20(10)
H(2O) O(2) C(8) O(1) -9.20(10)
H(2O) O(2) C(8) C(7) 171.40(10)
C(2) C(1) C(3) C(2) 0.00(10)
C(3) C(1) C(2) C(3) 0.00(10)
C(2) C(1) C(3) C(4) 134.20(10)
C(2) C(1) C(3) C(7) -127.90(10)
C(3) C(1) C(2) H(21) -108.00(10)
C(3) C(1) C(2) H(22) 107.50(10)
H(11) C(1) C(2) C(3) 105.50(10)
H(11) C(1) C(2) H(21) -2.50(10)
H(11) C(1) C(2) H(22) -147.00(10)
H(12) C(1) C(2) C(3) -107.70(10)
H(12) C(1) C(2) H(21) 144.30(10)
H(12) C(1) C(2) H(22) -0.20(10)
H(11) C(1) C(3) C(2) -107.00(10)
H(11) C(1) C(3) C(4) 27.20(10)
H(11) C(1) C(3) C(7) 125.10(10)
H(12) C(1) C(3) C(2) 106.80(10)
H(12) C(1) C(3) C(4) -119.00(10)
H(12) C(1) C(3) C(7) -21.10(10)
C(1) C(2) C(3) C(1) 0.00(10)
C(1) C(2) C(3) C(4) -134.40(10)
C(1) C(2) C(3) C(7) 128.60(10)
H(21) C(2) C(3) C(1) 107.10(10)
H(21) C(2) C(3) C(4) -27.30(10)
H(21) C(2) C(3) C(7) -124.30(10)
H(22) C(2) C(3) C(1) -109.00(10)
H(22) C(2) C(3) C(4) 116.60(10)
H(22) C(2) C(3) C(7) 19.60(10)
C(1) C(3) C(4) C(5) 3.00(10)
C(1) C(3) C(4) C(6) -103.10(10)
C(1) C(3) C(4) C(7) 128.20(10)
C(1) C(3) C(7) C(4) -132.40(10)
C(1) C(3) C(7) C(8) 118.80(10)
C(1) C(3) C(7) H(7) -24.30(10)
C(2) C(3) C(4) C(5) 107.50(10)
C(2) C(3) C(4) C(6) 1.40(10)
C(2) C(3) C(4) C(7) -127.30(10)
C(2) C(3) C(7) C(4) 132.10(10)
C(2) C(3) C(7) C(8) 23.30(10)
C(2) C(3) C(7) H(7) -119.80(10)
C(4) C(3) C(7) C(4) 0.00(10)
C(7) C(3) C(4) C(5) -125.20(10)
C(7) C(3) C(4) C(6) 128.70(10)
C(7) C(3) C(4) C(7) 0.00(10)
C(4) C(3) C(7) C(8) -108.70(10)
C(4) C(3) C(7) H(7) 108.20(10)
C(3) C(4) C(5) C(6) -136.20(10)
C(3) C(4) C(5) H(51) -27.80(10)
C(3) C(4) C(5) H(52) 114.60(10)
C(3) C(4) C(6) C(5) 134.60(10)
C(3) C(4) C(6) H(61) 27.30(10)
C(3) C(4) C(6) H(62) -120.00(10)
C(3) C(4) C(7) C(3) 0.00(10)
C(3) C(4) C(7) C(8) 106.10(10)
C(3) C(4) C(7) H(7) -107.00(10)
C(5) C(4) C(6) C(5) 0.00(10)
C(6) C(4) C(5) C(6) 0.00(10)
C(6) C(4) C(5) H(51) 108.30(10)
C(6) C(4) C(5) H(52) -109.30(10)
C(5) C(4) C(6) H(61) -107.30(10)
C(5) C(4) C(6) H(62) 105.40(10)
C(5) C(4) C(7) C(3) 132.20(10)
C(7) C(4) C(5) C(6) 127.90(10)
C(5) C(4) C(7) C(8) -121.60(10)
C(7) C(4) C(5) H(51) -123.70(10)
C(7) C(4) C(5) H(52) 18.70(10)
C(5) C(4) C(7) H(7) 25.20(10)
C(6) C(4) C(7) C(3) -134.50(10)
C(7) C(4) C(6) C(5) -125.20(10)
C(6) C(4) C(7) C(8) -28.40(10)
C(7) C(4) C(6) H(61) 127.50(10)
C(7) C(4) C(6) H(62) -19.80(10)
C(6) C(4) C(7) H(7) 118.50(10)
C(4) C(5) C(6) C(4) 0.00(10)
C(4) C(5) C(6) H(61) 108.50(10)
C(4) C(5) C(6) H(62) -109.40(10)
H(51) C(5) C(6) C(4) -105.60(10)
H(51) C(5) C(6) H(61) 2.90(10)
H(51) C(5) C(6) H(62) 145.00(10)
H(52) C(5) C(6) C(4) 106.20(10)
H(52) C(5) C(6) H(61) -145.30(10)
H(52) C(5) C(6) H(62) -3.20(10)
C(3) C(7) C(8) O(1) -137.40(10)
C(3) C(7) C(8) O(2) 42.00(10)
C(4) C(7) C(8) O(1) 156.70(10)
C(4) C(7) C(8) O(2) -23.90(10)
H(7) C(7) C(8) O(1) 7.80(10)
H(7) C(7) C(8) O(2) -172.80(10)
