#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/34/2103431.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_2103431
loop_
_publ_author_name
'Kálmán, Alajos'
'Fábián, László'
'Argay, Gyula'
'Bernáth, Gábor'
'Gyarmati, Zsuzsanna'
_publ_section_title
;
 Predictable close-packing similarities between cis- and
 trans-2-hydroxy-1-cyclooctanecarboxylic acids and
 trans-2-hydroxy-1-cyclooctanecarboxamide
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              855
_journal_page_last               863
_journal_paper_doi               10.1107/S0108768102009631
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C9 H16 O3'
_chemical_formula_sum            'C9 H16 O3'
_chemical_formula_weight         172.22
_chemical_name_systematic
;
 (1R*,2S*)-cis-2-hydroxy-1-cyclooctanecarboxylic 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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0820(10)
_cell_length_b                   7.6180(10)
_cell_length_c                   11.5790(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.84
_cell_measurement_theta_min      16.23
_cell_volume                     941.20(18)
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express'
_computing_data_reduction        'XCAD4 (Harms 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'MO k\a'
_diffrn_radiation_wavelength     0.710730
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4372
_diffrn_reflns_theta_full        34.95
_diffrn_reflns_theta_max         34.95
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.847
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         4074
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      0.837
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0502
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                2100
_reflns_number_total             4074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            de0017.cif
_cod_data_source_block           8C
_cod_original_cell_volume        941.20(17)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2103431
_cod_database_fobs_code          2103431
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 0.00245(6) 0.22080(10) 0.11454(7) 0.03749(19) Uani d U 1 O
H1 -0.0107 0.1985 0.0429 0.049 Uiso calc R 1 H
O2 0.07036(8) -0.17111(10) 0.13317(7) 0.0418(2) Uani d U 1 O
O3 0.14942(8) -0.06238(11) 0.31595(7) 0.0475(2) Uani d U 1 O
H3 0.1048 -0.1382 0.3333 0.062 Uiso calc R 1 H
C1 0.20784(9) 0.08228(13) 0.15978(8) 0.03058(19) Uani d U 1 C
H1A 0.2892 0.0920 0.2195 0.040 Uiso calc R 1 H
C2 0.13409(10) 0.25314(13) 0.16540(9) 0.0339(2) Uani d U 1 C
H2 0.1465 0.2825 0.2502 0.044 Uiso calc R 1 H
C3 0.17177(13) 0.41215(15) 0.10455(13) 0.0490(3) Uani d U 1 C
H3A 0.1116 0.5047 0.1042 0.064 Uiso calc R 1 H
H3B 0.1643 0.3816 0.0216 0.064 Uiso calc R 1 H
C4 0.30256(15) 0.4869(2) 0.15783(16) 0.0659(4) Uani d U 1 C
H4A 0.3075 0.5981 0.1186 0.086 Uiso calc R 1 H
H4B 0.3111 0.5121 0.2418 0.086 Uiso calc R 1 H
C5 0.41537(15) 0.3764(3) 0.15052(16) 0.0709(4) Uani d U 1 C
H5A 0.4314 0.2906 0.2148 0.092 Uiso calc R 1 H
H5B 0.4880 0.4528 0.1653 0.092 Uiso calc R 1 H
C6 0.40454(14) 0.2802(2) 0.03419(15) 0.0679(4) Uani d U 1 C
H6A 0.3448 0.3425 -0.0293 0.088 Uiso calc R 1 H
H6B 0.4851 0.2857 0.0165 0.088 Uiso calc R 1 H
C7 0.36447(12) 0.0883(2) 0.03002(13) 0.0558(3) Uani d U 1 C
H7A 0.4235 0.0279 0.0951 0.073 Uiso calc R 1 H
H7B 0.3739 0.0387 -0.0442 0.073 Uiso calc R 1 H
C8 0.23276(10) 0.04339(15) 0.03808(10) 0.0389(2) Uani d U 1 C
H8A 0.2178 -0.0805 0.0205 0.051 Uiso calc R 1 H
H8B 0.1728 0.1087 -0.0234 0.051 Uiso calc R 1 H
C9 0.13589(9) -0.06453(13) 0.19924(9) 0.0317(2) Uani d U 1 C
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
O1 0.0377(4) 0.0430(4) 0.0329(4) 0.0057(3) 0.0116(3) -0.0072(3)
O2 0.0545(5) 0.0348(4) 0.0360(4) -0.0087(3) 0.0123(3) -0.0054(3)
O3 0.0591(5) 0.0547(5) 0.0298(4) -0.0231(4) 0.0142(3) -0.0013(3)
C1 0.0319(4) 0.0335(4) 0.0272(4) -0.0001(4) 0.0094(3) 0.0011(3)
C2 0.0404(5) 0.0325(5) 0.0282(4) 0.0006(4) 0.0084(4) -0.0035(4)
C3 0.0580(7) 0.0342(5) 0.0534(7) -0.0001(5) 0.0123(6) 0.0077(5)
C4 0.0755(10) 0.0462(7) 0.0744(10) -0.0216(7) 0.0175(8) -0.0033(7)
C5 0.0572(8) 0.0814(10) 0.0695(10) -0.0275(8) 0.0091(7) 0.0028(8)
C6 0.0537(8) 0.0890(11) 0.0685(9) -0.0161(8) 0.0292(7) 0.0076(8)
C7 0.0439(6) 0.0772(9) 0.0537(7) 0.0001(6) 0.0258(6) -0.0004(7)
C8 0.0401(5) 0.0469(6) 0.0341(5) 0.0010(4) 0.0177(4) -0.0025(4)
C9 0.0353(4) 0.0314(4) 0.0291(4) 0.0016(4) 0.0100(3) 0.0007(3)
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 O1 H1 109.5
C9 O3 H3 109.5
C9 C1 C8 111.98(8)
C9 C1 C2 106.34(8)
C8 C1 C2 115.38(8)
C9 C1 H1A 107.6
C8 C1 H1A 107.6
C2 C1 H1A 107.6
O1 C2 C3 108.82(9)
O1 C2 C1 109.10(8)
C3 C2 C1 115.96(9)
O1 C2 H2 107.5
C3 C2 H2 107.5
C1 C2 H2 107.5
C2 C3 C4 117.49(11)
C2 C3 H3A 107.9
C4 C3 H3A 107.9
C2 C3 H3B 107.9
C4 C3 H3B 107.9
H3A C3 H3B 107.2
C5 C4 C3 118.33(13)
C5 C4 H4A 107.7
C3 C4 H4A 107.7
C5 C4 H4B 107.7
C3 C4 H4B 107.7
H4A C4 H4B 107.1
C4 C5 C6 116.60(14)
C4 C5 H5A 108.1
C6 C5 H5A 108.1
C4 C5 H5B 108.1
C6 C5 H5B 108.1
H5A C5 H5B 107.3
C7 C6 C5 116.50(13)
C7 C6 H6A 108.2
C5 C6 H6A 108.2
C7 C6 H6B 108.2
C5 C6 H6B 108.2
H6A C6 H6B 107.3
C6 C7 C8 119.21(12)
C6 C7 H7A 107.5
C8 C7 H7A 107.5
C6 C7 H7B 107.5
C8 C7 H7B 107.5
H7A C7 H7B 107.0
C7 C8 C1 115.13(10)
C7 C8 H8A 108.5
C1 C8 H8A 108.5
C7 C8 H8B 108.5
C1 C8 H8B 108.5
H8A C8 H8B 107.5
O2 C9 O3 122.51(9)
O2 C9 C1 125.34(9)
O3 C9 C1 112.13(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.4393(12)
O1 H1 0.8200
O2 C9 1.2131(12)
O3 C9 1.3189(12)
O3 H3 0.8200
C1 C9 1.5140(14)
C1 C8 1.5363(13)
C1 C2 1.5476(14)
C1 H1A 0.9800
C2 C3 1.5157(16)
C2 H2 0.9800
C3 C4 1.5239(19)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.528(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.509(2)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.525(2)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.5263(16)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
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
O1 H1 O2 3 0.82 1.98 2.7876(11) 169.5
O3 H3 O1 4_556 0.82 1.82 2.6344(11) 170.9
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
C9 C1 C2 O1 -43.91(11)
C8 C1 C2 O1 80.90(11)
C9 C1 C2 C3 -167.16(9)
C8 C1 C2 C3 -42.36(13)
O1 C2 C3 C4 170.74(11)
C1 C2 C3 C4 -65.86(14)
C2 C3 C4 C5 67.30(18)
C3 C4 C5 C6 41.1(2)
C4 C5 C6 C7 -96.78(17)
C5 C6 C7 C8 66.10(19)
C6 C7 C8 C1 -67.83(17)
C9 C1 C8 C7 -137.14(11)
C2 C1 C8 C7 101.04(12)
C8 C1 C9 O2 -22.54(14)
C2 C1 C9 O2 104.33(11)
C8 C1 C9 O3 159.09(9)
C2 C1 C9 O3 -74.04(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16221976
