#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/63/2216330.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_2216330
loop_
_publ_author_name
'Betz, Richard'
'Klüfers, Peter'
_publ_section_title
;
 2,2-Dicyclopropylglycolic acid
;
_journal_coeditor_code           BT2631
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4921
_journal_page_last               o4921
_journal_paper_doi               10.1107/S1600536807061168
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H12 O3'
_chemical_formula_moiety         'C8 H12 O3'
_chemical_formula_sum            'C8 H12 O3'
_chemical_formula_weight         156.18
_chemical_name_common            '2,2-Di(cyclopropyl)glycolic acid'
_chemical_name_systematic
;
2,2-Dicyclopropylglycolic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_cell_angle_alpha                92.107(3)
_cell_angle_beta                 100.758(3)
_cell_angle_gamma                112.263(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8595(3)
_cell_length_b                   7.2955(3)
_cell_length_c                   10.5515(5)
_cell_measurement_reflns_used    3975
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.134
_cell_volume                     407.22(3)
_computing_cell_refinement       'Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2004)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3030
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.096(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0386
_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)+(0.0406P)²+0.1023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                1221
_reflns_number_total             1594
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bt2631.cif
_cod_data_source_block           I
_cod_database_code               2216330
_cod_database_fobs_code          2216330
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 O3 0.45110(17) 0.71307(15) 0.64164(10) 0.0310(3) Uani d . 1
H H83 0.4429 0.6235 0.5865 0.037 Uiso calc R 1
O O1 0.78873(19) 0.61259(16) 0.55317(11) 0.0356(3) Uani d . 1
O O2 1.11508(19) 0.85312(17) 0.68539(12) 0.0388(4) Uani d . 1
H H82 1.1983 0.7962 0.6561 0.047 Uiso calc R 1
C C1 0.8731(3) 0.7539(2) 0.63559(14) 0.0237(4) Uani d . 1
C C2 0.7095(2) 0.8385(2) 0.69426(14) 0.0231(4) Uani d . 1
C C3 0.7557(3) 1.0442(2) 0.65394(15) 0.0304(4) Uani d . 1
H H3 0.7210 1.0464 0.5577 0.037 Uiso calc R 1
C C4 0.9573(3) 1.2317(2) 0.7267(2) 0.0468(5) Uani d . 1
H H4A 1.0446 1.3374 0.6757 0.056 Uiso calc R 1
H H4B 1.0650 1.2212 0.8081 0.056 Uiso calc R 1
C C5 0.6863(3) 1.1889(2) 0.72612(19) 0.0451(5) Uani d . 1
H H5A 0.6063 1.2680 0.6746 0.054 Uiso calc R 1
H H5B 0.6267 1.1517 0.8070 0.054 Uiso calc R 1
C C6 0.7678(3) 0.8316(2) 0.83998(15) 0.0282(4) Uani d . 1
H H6 0.9396 0.9278 0.8863 0.034 Uiso calc R 1
C C7 0.6769(4) 0.6371(3) 0.89413(19) 0.0483(5) Uani d . 1
H H7A 0.5677 0.5164 0.8328 0.058 Uiso calc R 1
H H7B 0.7929 0.6153 0.9674 0.058 Uiso calc R 1
C C8 0.5697(3) 0.7866(3) 0.91947(17) 0.0397(5) Uani d . 1
H H8A 0.6198 0.8577 1.0083 0.048 Uiso calc R 1
H H8B 0.3944 0.7589 0.8736 0.048 Uiso calc R 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
O3 0.0178(5) 0.0361(6) 0.0352(7) 0.0091(5) 0.0027(5) -0.0136(5)
O1 0.0252(6) 0.0375(7) 0.0403(7) 0.0106(5) 0.0055(5) -0.0140(5)
O2 0.0188(6) 0.0469(7) 0.0477(8) 0.0137(5) 0.0024(5) -0.0166(6)
C1 0.0197(7) 0.0277(8) 0.0242(8) 0.0100(6) 0.0044(6) 0.0013(6)
C2 0.0167(7) 0.0257(8) 0.0250(8) 0.0077(6) 0.0026(6) -0.0029(6)
C3 0.0340(9) 0.0326(9) 0.0284(9) 0.0162(7) 0.0088(7) 0.0035(7)
C4 0.0463(11) 0.0298(10) 0.0559(12) 0.0049(8) 0.0130(9) 0.0055(8)
C5 0.0573(12) 0.0325(10) 0.0571(12) 0.0238(9) 0.0257(10) 0.0076(8)
C6 0.0265(8) 0.0331(8) 0.0247(8) 0.0121(7) 0.0043(6) 0.0005(6)
C7 0.0696(13) 0.0442(11) 0.0415(11) 0.0291(10) 0.0203(10) 0.0149(8)
C8 0.0403(10) 0.0526(11) 0.0305(9) 0.0199(8) 0.0142(8) 0.0051(8)
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
C2 O3 H83 109.5
C1 O2 H82 109.5
O1 C1 O2 124.35(13)
O1 C1 C2 123.54(13)
O2 C1 C2 112.11(12)
O3 C2 C3 108.01(12)
O3 C2 C6 109.26(12)
C3 C2 C6 114.76(12)
O3 C2 C1 108.04(11)
C3 C2 C1 109.06(12)
C6 C2 C1 107.53(12)
C4 C3 C5 60.16(12)
C4 C3 C2 124.26(14)
C5 C3 C2 121.31(13)
C4 C3 H3 113.6
C5 C3 H3 113.6
C2 C3 H3 113.6
C3 C4 C5 60.20(11)
C3 C4 H4A 117.8
C5 C4 H4A 117.8
C3 C4 H4B 117.8
C5 C4 H4B 117.8
H4A C4 H4B 114.9
C4 C5 C3 59.63(11)
C4 C5 H5A 117.8
C3 C5 H5A 117.8
C4 C5 H5B 117.8
C3 C5 H5B 117.8
H5A C5 H5B 114.9
C7 C6 C8 59.66(11)
C7 C6 C2 120.19(14)
C8 C6 C2 122.65(13)
C7 C6 H6 114.5
C8 C6 H6 114.5
C2 C6 H6 114.5
C8 C7 C6 60.49(11)
C8 C7 H7A 117.7
C6 C7 H7A 117.7
C8 C7 H7B 117.7
C6 C7 H7B 117.7
H7A C7 H7B 114.8
C7 C8 C6 59.85(11)
C7 C8 H8A 117.8
C6 C8 H8A 117.8
C7 C8 H8B 117.8
C6 C8 H8B 117.8
H8A C8 H8B 114.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C2 1.4273(16)
O3 H83 0.8400
O1 C1 1.2046(17)
O2 C1 1.3139(17)
O2 H82 0.8400
C1 C2 1.525(2)
C2 C3 1.513(2)
C2 C6 1.518(2)
C3 C4 1.489(2)
C3 C5 1.497(2)
C3 H3 1.0000
C4 C5 1.497(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.492(2)
C6 C8 1.501(2)
C6 H6 1.0000
C7 C8 1.489(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 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 H82 O3 1_655 0.84 1.83 2.6387(16) 161
O3 H83 O1 . 0.84 2.15 2.6572(16) 119
O3 H83 O1 2_666 0.84 2.07 2.8067(15) 146
C8 H8B O2 1_455 0.99 2.61 3.470(2) 145
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 O3 4.3(2)
O2 C1 C2 O3 -175.78(12)
O1 C1 C2 C3 -112.91(16)
O2 C1 C2 C3 67.05(16)
O1 C1 C2 C6 122.07(16)
O2 C1 C2 C6 -57.96(16)
O3 C2 C3 C4 154.67(14)
C6 C2 C3 C4 32.5(2)
C1 C2 C3 C4 -88.14(18)
O3 C2 C3 C5 81.55(17)
C6 C2 C3 C5 -40.6(2)
C1 C2 C3 C5 -161.26(15)
C2 C3 C4 C5 -109.52(17)
C2 C3 C5 C4 114.25(17)
O3 C2 C6 C7 44.52(18)
C3 C2 C6 C7 165.97(14)
C1 C2 C6 C7 -72.51(17)
O3 C2 C6 C8 -26.75(19)
C3 C2 C6 C8 94.70(17)
C1 C2 C6 C8 -143.77(15)
C2 C6 C7 C8 -112.50(16)
C2 C6 C8 C7 108.48(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21120478
