Synthesis of tetronic acids from propargylic alcohols and CO<sub>2</sub>.
Shen, Guo; Zhou, Wen-Jun; Zhang, Xiao-Bo; Cao, Guang-Mei; Zhang, Zhen; Ye, Jian-Heng; Liao, Li-Li; Li, Jing; Yu, Da-Gang; Chemical communications (Cambridge, England) 54 (2018) 5610–5613; doi:10.1039/c8cc03039a

data_7121627
_publ_section_title
;
 Synthesis of tetronic acids from propargylic alcohols and CO<sub>2</sub>.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5610
_journal_page_last               5613
_journal_paper_doi               10.1039/c8cc03039a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C12 H12 O3'
_chemical_formula_sum            'C12 H12 O3'
_chemical_formula_weight         204.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-15
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
;
2018-01-09 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                87.679(8)
_cell_angle_beta                 83.576(7)
_cell_angle_gamma                73.938(9)
_cell_formula_units_Z            2
_cell_length_a                   6.7868(6)
_cell_length_b                   8.5848(10)
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_cell_measurement_reflns_used    2260
_cell_measurement_temperature    290.8(6)
_cell_measurement_theta_max      27.5650
_cell_measurement_theta_min      3.6030
_cell_volume                     525.10(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   35.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5845  178.0000 -120.0000 81

  2 omega  -48.00   60.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5845  -57.0000 -150.0000 108

  3 omega   -9.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5845   57.0000   90.0000 109

  4 omega  -55.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5845  -77.0000 -150.0000 121

  5 omega   35.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5845  178.0000    0.0000 81

  6 omega  -55.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5845  -77.0000  -30.0000 121

  7 omega   -9.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5845   57.0000  -90.0000 109

  8 omega  -20.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.5220  -99.0000  120.0000 46

  9 omega  -20.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.5220  -99.0000  -60.0000 46
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0039706000
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_diffrn_orient_matrix_UB_22      -0.0799444000
_diffrn_orient_matrix_UB_23      0.0076228000
_diffrn_orient_matrix_UB_31      -0.0885446000
_diffrn_orient_matrix_UB_32      -0.0280752000
_diffrn_orient_matrix_UB_33      0.0185791000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6297
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         3.305
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0479
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+0.0552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1794
_reflns_number_total             2152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03039a2.cif
_cod_data_source_block           ydg-zxb-1-62
_cod_depositor_comments          'Adding full bibliography for 7121627.cif.'
_cod_database_code               7121627
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00F(H00j)
2.b Idealised Me refined as rotating group:
 C00D(H00d,H00e,H00f), C00E(H00g,H00h,H00i)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              47272
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-09-14
_olex2_submission_special_instructions 'No special instructions were received'