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#$Date: 2022-03-18 10:39:25 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104791.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_8104791
loop_
_publ_author_name
'Hou, Xuehui'
'Wang, Qinglong'
'Wang, Jianling'
'Li, Aiqin'
'Ding, Degang'
'Lv, Quanjian'
_publ_section_title
;
 Crystal structure of
 3-(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C9H12O5
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              651
_journal_page_last               652
_journal_paper_doi               10.1515/ncrs-2021-0027
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C9 H12 O5'
_chemical_formula_sum            'C9 H12 O5'
_chemical_formula_weight         200.19
_chemical_name_systematic
;
(1R,2R,3S,4R)-3-(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic 
acid, C9H12O5, C₉H₁₂O₅
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_cell_angle_alpha                102.238(8)
_cell_angle_beta                 95.381(8)
_cell_angle_gamma                90.940(9)
_cell_formula_units_Z            2
_cell_length_a                   5.6537(6)
_cell_length_b                   7.7954(8)
_cell_length_c                   10.6841(9)
_cell_measurement_reflns_used    2097
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9810
_cell_measurement_theta_min      4.2340
_cell_volume                     457.83(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)[2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[2]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[3]'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)[4]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0832364000
_diffrn_orient_matrix_UB_12      0.0650857000
_diffrn_orient_matrix_UB_13      -0.1227964000
_diffrn_orient_matrix_UB_21      -0.0506090000
_diffrn_orient_matrix_UB_22      0.1802607000
_diffrn_orient_matrix_UB_23      0.0827522000
_diffrn_orient_matrix_UB_31      0.2559463000
_diffrn_orient_matrix_UB_32      0.0649275000
_diffrn_orient_matrix_UB_33      -0.0077508000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3149
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.255
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)[1]
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1345P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2279
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2411
_reflns_number_total             3149
_cod_data_source_file            suppl_j_ncrs-2021-0027_suppl.cif
_cod_data_source_block           exp_1115
_cod_database_code               8104791
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0546(4) 1.1100(3) 0.6853(3) 0.0410(7) Uani 1 1 d . . . . .
O2 O -0.0577(5) 0.7088(4) 0.5760(3) 0.0517(8) Uani 1 1 d . . . . .
O3 O 0.2902(6) 0.5800(4) 0.5636(4) 0.0649(10) Uani 1 1 d . . . . .
H3 H 0.206(11) 0.505(8) 0.530(6) 0.078 Uiso 1 1 d R . . . .
O4 O -0.1939(5) 0.8982(4) 0.8723(3) 0.0475(7) Uani 1 1 d . . . . .
O5 O 0.0380(5) 0.6669(3) 0.8405(3) 0.0508(8) Uani 1 1 d . . . . .
C1 C 0.2580(6) 1.0339(5) 0.6267(4) 0.0406(9) Uani 1 1 d . . . . .
H1 H 0.2371 1.0082 0.5325 0.049 Uiso 1 1 calc R . . . .
C2 C 0.4569(7) 1.1704(5) 0.6848(4) 0.0466(10) Uani 1 1 d . . . . .
H2A H 0.4583 1.2654 0.6390 0.056 Uiso 1 1 calc R . . . .
H2B H 0.6113 1.1181 0.6854 0.056 Uiso 1 1 calc R . . . .
C3 C 0.3857(7) 1.2340(5) 0.8223(4) 0.0484(10) Uani 1 1 d . . . . .
H3A H 0.5052 1.2080 0.8863 0.058 Uiso 1 1 calc R . . . .
H3B H 0.3587 1.3590 0.8409 0.058 Uiso 1 1 calc R . . . .
C4 C 0.1554(7) 1.1262(5) 0.8162(3) 0.0385(8) Uani 1 1 d . . . . .
H4 H 0.0493 1.1798 0.8798 0.046 Uiso 1 1 calc R . . . .
C5 C 0.2086(6) 0.9352(4) 0.8203(3) 0.0341(8) Uani 1 1 d . . . . .
H5 H 0.3396 0.9324 0.8867 0.041 Uiso 1 1 calc R . . . .
C6 C 0.2944(6) 0.8689(5) 0.6838(3) 0.0376(8) Uani 1 1 d . . . . .
H6 H 0.4642 0.8454 0.6928 0.045 Uiso 1 1 calc R . . . .
C7 C 0.1598(7) 0.7092(5) 0.6033(3) 0.0403(9) Uani 1 1 d . . . . .
C8 C -0.0075(6) 0.8362(5) 0.8467(3) 0.0372(8) Uani 1 1 d . . . . .
C9 C -0.1669(9) 0.5516(6) 0.8394(6) 0.0660(13) Uani 1 1 d . . . . .
H9A H -0.2946 0.5783 0.7817 0.099 Uiso 1 1 calc GR . . . .
H9B H -0.2162 0.5685 0.9246 0.099 Uiso 1 1 calc GR . . . .
H9C H -0.1252 0.4316 0.8112 0.099 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 C4 96.0(3) . .
C7 O3 H3 106(5) . .
C8 O5 C9 115.8(3) . .
O1 C1 H1 113.6 . .
O1 C1 C2 102.7(3) . .
O1 C1 C6 102.9(3) . .
C2 C1 H1 113.6 . .
C2 C1 C6 109.4(3) . .
C6 C1 H1 113.6 . .
C1 C2 H2A 111.5 . .
C1 C2 H2B 111.5 . .
C1 C2 C3 101.2(3) . .
H2A C2 H2B 109.4 . .
C3 C2 H2A 111.5 . .
C3 C2 H2B 111.5 . .
C2 C3 H3A 111.5 . .
C2 C3 H3B 111.5 . .
H3A C3 H3B 109.3 . .
C4 C3 C2 101.3(3) . .
C4 C3 H3A 111.5 . .
C4 C3 H3B 111.5 . .
O1 C4 C3 103.3(3) . .
O1 C4 H4 113.3 . .
O1 C4 C5 102.0(3) . .
C3 C4 H4 113.3 . .
C3 C4 C5 110.6(3) . .
C5 C4 H4 113.3 . .
C4 C5 H5 109.7 . .
C4 C5 C6 100.8(3) . .
C6 C5 H5 109.7 . .
C8 C5 C4 111.8(3) . .
C8 C5 H5 109.7 . .
C8 C5 C6 114.9(3) . .
C1 C6 C5 100.5(3) . .
C1 C6 H6 109.5 . .
C5 C6 H6 109.5 . .
C7 C6 C1 112.7(3) . .
C7 C6 C5 114.8(3) . .
C7 C6 H6 109.5 . .
O2 C7 O3 124.3(4) . .
O2 C7 C6 121.3(3) . .
O3 C7 C6 114.3(3) . .
O4 C8 O5 123.4(4) . .
O4 C8 C5 125.9(3) . .
O5 C8 C5 110.7(3) . .
O5 C9 H9A 109.5 . .
O5 C9 H9B 109.5 . .
O5 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.438(4) .
O1 C4 1.438(4) .
O2 C7 1.237(5) .
O3 H3 0.75(6) .
O3 C7 1.280(5) .
O4 C8 1.197(4) .
O5 C8 1.338(5) .
O5 C9 1.453(5) .
C1 H1 0.9800 .
C1 C2 1.527(6) .
C1 C6 1.545(5) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.541(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C3 C4 1.526(5) .
C4 H4 0.9800 .
C4 C5 1.532(5) .
C5 H5 0.9800 .
C5 C6 1.566(5) .
C5 C8 1.514(5) .
C6 H6 0.9800 .
C6 C7 1.504(5) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
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
O3 H3 O2 0.75(6) 1.94(7) 2.671(4) 166(6) 2_566
C6 H6 O4 0.98 2.56 3.342(4) 137.3 1_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 36.0(4) . . . .
O1 C1 C6 C5 -32.5(3) . . . .
O1 C1 C6 C7 90.2(3) . . . .
O1 C4 C5 C6 38.0(3) . . . .
O1 C4 C5 C8 -84.4(3) . . . .
C1 O1 C4 C3 55.7(3) . . . .
C1 O1 C4 C5 -59.1(3) . . . .
C1 C2 C3 C4 -1.6(4) . . . .
C1 C6 C7 O2 -56.2(5) . . . .
C1 C6 C7 O3 121.7(4) . . . .
C2 C1 C6 C5 76.1(3) . . . .
C2 C1 C6 C7 -161.1(3) . . . .
C2 C3 C4 O1 -33.1(4) . . . .
C2 C3 C4 C5 75.3(4) . . . .
C3 C4 C5 C6 -71.3(4) . . . .
C3 C4 C5 C8 166.2(3) . . . .
C4 O1 C1 C2 -56.8(3) . . . .
C4 O1 C1 C6 56.9(3) . . . .
C4 C5 C6 C1 -3.2(3) . . . .
C4 C5 C6 C7 -124.4(3) . . . .
C4 C5 C8 O4 -5.9(5) . . . .
C4 C5 C8 O5 175.4(3) . . . .
C5 C6 C7 O2 58.1(5) . . . .
C5 C6 C7 O3 -123.9(4) . . . .
C6 C1 C2 C3 -72.8(4) . . . .
C6 C5 C8 O4 -120.0(4) . . . .
C6 C5 C8 O5 61.4(4) . . . .
C8 C5 C6 C1 117.1(3) . . . .
C8 C5 C6 C7 -4.1(4) . . . .
C9 O5 C8 O4 12.7(6) . . . .
C9 O5 C8 C5 -168.6(4) . . . .
