#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/14/4021458.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4021458
loop_
_publ_author_name
'Natalia Pérez-Hernández'
'Martín Febles'
'Cirilo Pérez'
'Matías L. Rodríguez'
'Concepción Foces-Foces'
'Julio D. Martín'
_publ_section_title
;
 Synthesis and Structure of Hydroxyl Acids of General Structure
 7,7-Alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane-
 1-carboxylic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1139
_journal_page_last               1151
_journal_paper_doi               10.1021/jo052237p
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C13 H18 O4'
_chemical_formula_sum            'C13 H18 O4'
_chemical_formula_weight         238.27
_chemical_name_systematic
;
 (1R*, 5R*)-7,7-divinyl-5-hydroxymethyl-6-
oxabicyclo[3.2.1]octane-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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 128.818(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9310(12)
_cell_length_b                   14.491(3)
_cell_length_c                   12.0300(13)
_cell_measurement_reflns_used    2878
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.59
_cell_volume                     1213.1(3)
_computing_cell_refinement
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 2000)'
_computing_data_reduction
'HKL Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97, WinGX (Farrugia, 1999) and PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2788
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9581
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.7667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                2415
_reflns_number_total             2788
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052237psi20051102_104042_3.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021458
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.26592(15) 0.25270(7) 0.56433(11) 0.0158(3) Uani 1 1 d .
O2 O -0.01641(16) 0.10104(7) 0.40645(12) 0.0196(3) Uani 1 1 d .
H2 H -0.0376 0.1034 0.4653 0.029 Uiso 1 1 calc R
O3 O -0.00449(16) 0.37942(8) 0.14070(12) 0.0216(3) Uani 1 1 d .
O4 O 0.20585(17) 0.48283(8) 0.30345(13) 0.0265(3) Uani 1 1 d .
H4 H 0.1372 0.5196 0.2349 0.040 Uiso 1 1 calc R
C1 C 0.2721(2) 0.18469(10) 0.47826(16) 0.0149(3) Uani 1 1 d .
C2 C 0.4801(2) 0.16703(11) 0.54046(18) 0.0206(4) Uani 1 1 d .
H2A H 0.4821 0.1249 0.4766 0.025 Uiso 1 1 calc R
H2B H 0.5493 0.1365 0.6344 0.025 Uiso 1 1 calc R
C3 C 0.5835(2) 0.25687(12) 0.55824(18) 0.0233(4) Uani 1 1 d .
H3A H 0.6954 0.2419 0.5627 0.028 Uiso 1 1 calc R
H3B H 0.6330 0.2856 0.6502 0.028 Uiso 1 1 calc R
C4 C 0.4566(2) 0.32746(11) 0.43804(17) 0.0193(3) Uani 1 1 d .
H4A H 0.4578 0.3133 0.3581 0.023 Uiso 1 1 calc R
H4B H 0.5122 0.3898 0.4739 0.023 Uiso 1 1 calc R
C5 C 0.2463(2) 0.32827(10) 0.38150(16) 0.0148(3) Uani 1 1 d .
C6 C 0.1638(2) 0.23109(10) 0.33364(16) 0.0154(3) Uani 1 1 d .
H6A H 0.0232 0.2302 0.2806 0.018 Uiso 1 1 calc R
H6B H 0.1935 0.2026 0.2747 0.018 Uiso 1 1 calc R
C7 C 0.1339(2) 0.39846(10) 0.26228(17) 0.0165(3) Uani 1 1 d .
C8 C 0.1855(2) 0.09577(10) 0.48133(17) 0.0190(3) Uani 1 1 d .
H8A H 0.2111 0.0459 0.4390 0.023 Uiso 1 1 calc R
H8B H 0.2501 0.0790 0.5819 0.023 Uiso 1 1 calc R
C9 C 0.2298(2) 0.34303(10) 0.50281(17) 0.0168(3) Uani 1 1 d .
C10 C 0.3728(3) 0.41171(12) 0.6164(2) 0.0267(4) Uani 1 1 d .
H10 H 0.3690 0.4730 0.5868 0.032 Uiso 1 1 calc R
C11 C 0.5019(3) 0.39237(15) 0.7532(2) 0.0374(5) Uani 1 1 d .
H11A H 0.5099 0.3318 0.7867 0.045 Uiso 1 1 calc R
H11B H 0.5870 0.4390 0.8183 0.045 Uiso 1 1 calc R
C12 C 0.0317(3) 0.37647(12) 0.4435(2) 0.0246(4) Uani 1 1 d .
H12 H -0.0085 0.4343 0.3957 0.030 Uiso 1 1 calc R
C13 C -0.0894(3) 0.33310(13) 0.4521(2) 0.0285(4) Uani 1 1 d .
H13A H -0.0555 0.2751 0.4990 0.034 Uiso 1 1 calc R
H13B H -0.2111 0.3597 0.4115 0.034 Uiso 1 1 calc R
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
C9 O1 C1 110.29(11)
C8 O2 H2 109.5
C7 O4 H4 109.5
O1 C1 C8 108.12(12)
O1 C1 C6 103.55(11)
C8 C1 C6 115.87(12)
O1 C1 C2 109.98(12)
C8 C1 C2 109.16(12)
C6 C1 C2 109.94(12)
C1 C2 C3 111.58(13)
C1 C2 H2A 109.3
C3 C2 H2A 109.3
C1 C2 H2B 109.3
C3 C2 H2B 109.3
H2A C2 H2B 108.0
C2 C3 C4 114.16(13)
C2 C3 H3A 108.7
C4 C3 H3A 108.7
C2 C3 H3B 108.7
C4 C3 H3B 108.7
H3A C3 H3B 107.6
C3 C4 C5 113.26(12)
C3 C4 H4A 108.9
C5 C4 H4A 108.9
C3 C4 H4B 108.9
C5 C4 H4B 108.9
H4A C4 H4B 107.7
C7 C5 C6 112.71(12)
C7 C5 C4 108.84(12)
C6 C5 C4 108.98(12)
C7 C5 C9 113.33(12)
C6 C5 C9 99.91(11)
C4 C5 C9 112.83(12)
C1 C6 C5 99.58(11)
C1 C6 H6A 111.9
C5 C6 H6A 111.9
C1 C6 H6B 111.9
C5 C6 H6B 111.9
H6A C6 H6B 109.6
O3 C7 O4 123.28(14)
O3 C7 C5 123.88(14)
O4 C7 C5 112.81(13)
O2 C8 C1 113.69(12)
O2 C8 H8A 108.8
C1 C8 H8A 108.8
O2 C8 H8B 108.8
C1 C8 H8B 108.8
H8A C8 H8B 107.7
O1 C9 C12 110.67(12)
O1 C9 C10 110.08(13)
C12 C9 C10 106.84(13)
O1 C9 C5 103.46(11)
C12 C9 C5 111.63(13)
C10 C9 C5 114.20(12)
C11 C10 C9 124.67(16)
C11 C10 H10 117.7
C9 C10 H10 117.7
C10 C11 H11A 120.0
C10 C11 H11B 120.0
H11A C11 H11B 120.0
C13 C12 C9 126.02(16)
C13 C12 H12 117.0
C9 C12 H12 117.0
C12 C13 H13A 120.0
C12 C13 H13B 120.0
H13A C13 H13B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.4374(18)
O1 C1 1.4554(18)
O2 C8 1.4257(19)
O2 H2 0.8400
O3 C7 1.2152(19)
O4 C7 1.3243(19)
O4 H4 0.8400
C1 C8 1.515(2)
C1 C6 1.518(2)
C1 C2 1.528(2)
C2 C3 1.532(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.539(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.546(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C7 1.515(2)
C5 C6 1.525(2)
C5 C9 1.571(2)
C6 H6A 0.9900
C6 H6B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C12 1.514(2)
C9 C10 1.517(2)
C10 C11 1.318(3)
C10 H10 0.9500
C11 H11A 0.9500
C11 H11B 0.9500
C12 C13 1.309(2)
C12 H12 0.9500
C13 H13A 0.9500
C13 H13B 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.84 1.95 2.7671(17) 162.4 4_566
O4 H4 O2 0.84 1.77 2.6109(16) 173.5 2
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 O1 C1 C8 -144.52(12)
C9 O1 C1 C6 -21.08(15)
C9 O1 C1 C2 96.37(14)
O1 C1 C2 C3 -54.12(17)
C8 C1 C2 C3 -172.59(13)
C6 C1 C2 C3 59.28(17)
C1 C2 C3 C4 -37.2(2)
C2 C3 C4 C5 36.2(2)
C3 C4 C5 C7 -178.90(13)
C3 C4 C5 C6 -55.61(17)
C3 C4 C5 C9 54.40(17)
O1 C1 C6 C5 42.38(13)
C8 C1 C6 C5 160.57(12)
C2 C1 C6 C5 -75.10(14)
C7 C5 C6 C1 -167.01(12)
C4 C5 C6 C1 72.05(14)
C9 C5 C6 C1 -46.42(13)
C6 C5 C7 O3 -1.5(2)
C4 C5 C7 O3 119.48(16)
C9 C5 C7 O3 -114.11(16)
C6 C5 C7 O4 -179.70(13)
C4 C5 C7 O4 -58.68(17)
C9 C5 C7 O4 67.74(17)
O1 C1 C8 O2 69.22(16)
C6 C1 C8 O2 -46.42(18)
C2 C1 C8 O2 -171.15(13)
C1 O1 C9 C12 110.93(14)
C1 O1 C9 C10 -131.19(13)
C1 O1 C9 C5 -8.76(15)
C7 C5 C9 O1 154.88(12)
C6 C5 C9 O1 34.74(14)
C4 C5 C9 O1 -80.85(14)
C7 C5 C9 C12 35.85(17)
C6 C5 C9 C12 -84.30(14)
C4 C5 C9 C12 160.12(13)
C7 C5 C9 C10 -85.48(17)
C6 C5 C9 C10 154.38(13)
C4 C5 C9 C10 38.80(18)
O1 C9 C10 C11 -4.6(2)
C12 C9 C10 C11 115.7(2)
C5 C9 C10 C11 -120.40(19)
O1 C9 C12 C13 3.4(2)
C10 C9 C12 C13 -116.4(2)
C5 C9 C12 C13 118.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11506958
