Development of pharmaceutically relevant bio-based intermediates though aldol condensation and Claisen–Schmidt reactions of dihydrolevoglucosenone (Cyrene®)
Hughes, Liam; McElroy, Con R.; Whitwood, Adrian C.; Hunt, Andrew J.; Green Chemistry 20 (2018) 4423–; doi:10.1039/C8GC01227J

data_7230738
_publ_section_title
;
 Development of pharmaceutically relevant bio-based intermediates though
 aldol condensation and Claisen--Schmidt reactions of
 dihydrolevoglucosenone (Cyrene&#x00AE;)
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              4423
_journal_paper_doi               10.1039/C8GC01227J
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H10 O4'
_chemical_formula_sum            'C11 H10 O4'
_chemical_formula_weight         206.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.22158(15)
_cell_length_b                   9.60997(16)
_cell_length_c                   13.4791(3)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    109.95(10)
_cell_measurement_theta_max      70.8130
_cell_measurement_theta_min      5.6500
_cell_volume                     935.44(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      5.00  51.00   1.00    1.00    --    0.00  57.00  60.00   46
  2  \w     39.00  88.00   1.00    1.00    --   54.00  57.00 150.00   49
  3  \w    100.00 130.00   1.00    1.00    --  108.00 111.00 150.00   30
  4  \w    118.00 158.00   1.00    1.00    --  108.00 111.00  90.00   40
  5  \w    103.00 177.00   1.00    1.00    --  108.00 111.00  60.00   74
  6  \w     83.00 175.00   1.00    1.00    --  108.00  37.00-120.00   92
  7  \w     66.00 121.00   1.00    1.00    --   54.00  57.00-180.00   55
  8  \w     14.00  76.00   1.00    1.00    --   54.00 -77.00-150.00   62
  9  \w     73.00 110.00   1.00    1.00    --  108.00-111.00-180.00   37
 10  \w     40.00  87.00   1.00    1.00    --  108.00-111.00  30.00   47
 11  \w    -10.00  30.00   1.00    1.00    --    0.00  57.00-180.00   40
 12  \w     40.00  66.00   1.00    1.00    --   54.40 -57.00-180.00   26
 13  \w    -16.00  57.00   1.00    1.00    --   54.40 -77.00 150.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0872353000
_diffrn_orient_matrix_UB_12      0.0033126000
_diffrn_orient_matrix_UB_13      0.1041546000
_diffrn_orient_matrix_UB_21      -0.1942161000
_diffrn_orient_matrix_UB_22      0.0142366000
_diffrn_orient_matrix_UB_23      0.0463448000
_diffrn_orient_matrix_UB_31      -0.0153106000
_diffrn_orient_matrix_UB_32      -0.1597147000
_diffrn_orient_matrix_UB_33      0.0062315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2614
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.022
_diffrn_reflns_theta_max         67.022
_diffrn_reflns_theta_min         5.654
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0247
_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/[\s^2^(Fo^2^)+(0.0407P)^2^+0.1195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0646
_reflns_Friedel_coverage         0.493
_reflns_Friedel_fraction_full    0.720
_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                1435
_reflns_number_total             1484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc01227j2.cif
_cod_data_source_block           jhc1703
_cod_depositor_comments
'Adding full bibliography for 7230738--7230745.cif.'
_cod_database_code               7230738
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C11 H10 O4'
_chemical_oxdiff_usercomment     'Liam Hughes lmhfurfural'
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_olex2_date_sample_data_collection 2017-04-18
_olex2_date_sample_submission    2017-04-05
_olex2_submission_original_sample_id lmhfurfural
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.129
_oxdiff_exptl_absorpt_empirical_full_min 0.866