#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/50/2215003.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_2215003
loop_
_publ_author_name
'Betz, Richard'
'Klüfers, Peter'
_publ_section_title
;
 1-Hydroxycyclopropane-1-carboxylic acid
;
_journal_coeditor_code           BT2452
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3891
_journal_page_last               o3891
_journal_paper_doi               10.1107/S1600536807041256
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C4 H6 O3'
_chemical_formula_moiety         'C4 H6 O3'
_chemical_formula_sum            'C4 H6 O3'
_chemical_formula_weight         102.09
_chemical_name_systematic
;
1-Hydroxycyclopropane-1-carboxylic acid
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.119(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0310(3)
_cell_length_b                   4.7250(2)
_cell_length_c                   12.0343(4)
_cell_measurement_reflns_used    5717
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     461.08(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2004)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1956
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.435
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0457
_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)+(0.0567P)²+0.294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                908
_reflns_number_total             1045
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2452.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215003
_cod_database_fobs_code          2215003
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_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 O2 0.03457(13) 0.9329(3) 0.19543(11) 0.0300(3) Uani d . 1
H H2 0.0058 0.8649 0.2474 0.052(3) Uiso calc R 1
O O11 0.28515(15) 1.0745(3) 0.40905(11) 0.0372(4) Uani d . 1
H H11 0.3673 1.1028 0.4773 0.052(3) Uiso calc R 1
O O12 0.46529(15) 0.8034(3) 0.37692(12) 0.0415(4) Uani d . 1
C C1 0.32519(19) 0.9036(3) 0.34354(14) 0.0270(4) Uani d . 1
C C2 0.19178(18) 0.8327(3) 0.21967(14) 0.0252(4) Uani d . 1
C C3 0.2062(2) 0.5619(4) 0.15971(15) 0.0318(4) Uani d . 1
H H31 0.3021 0.4385 0.2069 0.052(3) Uiso calc R 1
H H32 0.1030 0.4601 0.1071 0.052(3) Uiso calc R 1
C C4 0.2377(2) 0.8372(4) 0.11322(15) 0.0305(4) Uani d . 1
H H41 0.1540 0.9057 0.0321 0.052(3) Uiso calc R 1
H H42 0.3531 0.8841 0.1319 0.052(3) 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
O2 0.0224(6) 0.0321(7) 0.0356(6) 0.0007(4) 0.0128(5) 0.0009(5)
O11 0.0331(7) 0.0449(8) 0.0304(6) 0.0060(5) 0.0110(5) -0.0078(5)
O12 0.0273(6) 0.0526(9) 0.0369(7) 0.0089(6) 0.0069(5) -0.0097(6)
C1 0.0267(7) 0.0271(8) 0.0293(8) 0.0010(6) 0.0142(6) 0.0004(6)
C2 0.0233(7) 0.0238(8) 0.0293(8) -0.0002(6) 0.0124(6) -0.0002(6)
C3 0.0341(9) 0.0260(8) 0.0350(9) -0.0027(7) 0.0149(7) -0.0047(7)
C4 0.0320(8) 0.0322(9) 0.0292(8) -0.0018(7) 0.0152(7) -0.0009(7)
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 0.0000 '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 0.0000 '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 O2 H2 109.5
C1 O11 H11 109.5
O12 C1 O11 124.25(15)
O12 C1 C2 120.02(14)
O11 C1 C2 115.72(14)
O2 C2 C1 115.67(13)
O2 C2 C3 118.81(13)
C1 C2 C3 118.08(14)
O2 C2 C4 116.77(13)
C1 C2 C4 116.35(13)
C3 C2 C4 59.37(11)
C4 C3 C2 60.58(11)
C4 C3 H31 117.7
C2 C3 H31 117.7
C4 C3 H32 117.7
C2 C3 H32 117.7
H31 C3 H32 114.8
C3 C4 C2 60.04(10)
C3 C4 H41 117.8
C2 C4 H41 117.8
C3 C4 H42 117.8
C2 C4 H42 117.8
H41 C4 H42 114.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C2 1.4001(18) ?
O2 H2 0.8400 ?
O11 C1 1.287(2) ?
O11 H11 0.8400 ?
O12 C1 1.240(2) ?
C1 C2 1.485(2) y
C2 C3 1.502(2) y
C2 C4 1.510(2) y
C3 C4 1.492(2) ?
C3 H31 0.9900 ?
C3 H32 0.9900 ?
C4 H41 0.9900 ?
C4 H42 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 H2 O2 2_545 0.84 2.23 2.9015(13) 136.5
O11 H11 O12 3_676 0.84 1.80 2.6336(17) 174.5
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
O12 C1 C2 O2 173.88(15)
O11 C1 C2 O2 -7.4(2)
O12 C1 C2 C3 24.3(2)
O11 C1 C2 C3 -156.97(14)
O12 C1 C2 C4 -43.4(2)
O11 C1 C2 C4 135.37(15)
O2 C2 C3 C4 105.77(16)
C1 C2 C3 C4 -105.60(16)
O2 C2 C4 C3 -109.19(16)
C1 C2 C4 C3 108.49(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2014967
