The crystal structure of 3-hydroxy-5-oxo-4-propanoylcyclohex-3-ene-1-carboxylic monohydrate, C10H14O6
Huang, Li-Ming; Xia, Ying-Fan; Wang, Hai-Bin; Lin, Shu-Ting; Zhang, Jia-Rong; Jiang, Cheng-Jun; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 157–158; doi:10.1515/ncrs-2022-0507

data_8107380
_publ_section_title
;
 The crystal structure of
 3-hydroxy-5-oxo-4-propanoylcyclohex-3-ene-1-carboxylic monohydrate,
 C10H14O6
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              157
_journal_page_last               158
_journal_paper_doi               10.1515/ncrs-2022-0507
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C10 H12 O5, H2 O'
_chemical_formula_sum            'C10 H14 O6'
_chemical_formula_weight         230.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                61.8330(10)
_cell_angle_beta                 68.6230(10)
_cell_angle_gamma                86.5750(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5531(2)
_cell_length_b                   9.3964(3)
_cell_length_c                   9.5089(3)
_cell_measurement_reflns_used    8224
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.48
_cell_volume                     548.80(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \? scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.145
_diffrn_reflns_theta_min         2.482
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1349 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.9252.
The \?/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0818P)^2^+0.2008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2265
_reflns_number_total             2427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0507_suppl.cif
_cod_data_source_block           mo_2
_cod_database_code               8107380
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H9A,H9B} of C9, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H3,H6A} of C2A, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O3-H3
 0.88 with sigma of 0.02
 O6-H6A
 0.87 with sigma of 0.02
 O2-H2
 0.84 with sigma of 0.02
 O1-C1 \\sim O1A-C1A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2
 with sigma of 0.02
 C1-C2A \\sim C1A-C2A
 with sigma of 0.02
 O1-C2 \\sim O1A-C2
 with sigma of 0.04
 O1-C2A \\sim O1A-C2A
 with sigma of 0.04
 O2-C1 \\sim O2A-C1A
 with sigma of 0.02
 O1-O2 \\sim O1A-O2A
 with sigma of 0.04
 O2-C2 \\sim O2A-C2
 with sigma of 0.04
 O2-C2A \\sim O2A-C2A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim C1 \\sim C2 \\sim O1A \\sim O2A \\sim C1A \\sim C2A: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Sof(H3BC)=Sof(H3BD)=Sof(H7BC)=Sof(H7BD)=Sof(O1A)=Sof(O2A)=Sof(H2AA)=Sof(C1A)=
 Sof(C2A)=Sof(H2AB)=1-FVAR(1)
 Sof(H3AA)=Sof(H3AB)=Sof(H7AA)=Sof(H7AB)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=
 Sof(H2A)=Sof(H2)=FVAR(1)
5.a Free rotating group:
 O6(H6B)
5.b Ternary CH refined with riding coordinates:
 C2(H2A), C2A(H2AB)
5.c Secondary CH2 refined with riding coordinates:
 C3(H3AA,H3AB), C3(H3BC,H3BD), C7(H7AA,H7AB), C7(H7BC,H7BD), C9(H9A,H9B)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
5.e Idealised tetrahedral OH refined as rotating group:
 O2A(H2AA)
;
_shelx_res_checksum              4000