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_7230739
_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         'C13 H11 N O5'
_chemical_formula_sum            'C13 H11 N O5'
_chemical_formula_weight         261.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-26
_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                 93.2815(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.36693(18)
_cell_length_b                   7.08624(14)
_cell_length_c                   19.5336(4)
_cell_measurement_reflns_used    5349
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.3430
_cell_measurement_theta_min      6.6300
_cell_volume                     1156.25(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -21.00  69.00   1.00    2.00    --    0.00  57.00 -90.00   90
  2  \w    -69.00  21.00   1.00    2.00    --    0.00 -57.00 -60.00   90
  3  \w    -69.00  21.00   1.00    2.00    --    0.00 -57.00-120.00   90
  4  \w    -18.00  80.00   1.00    8.00    --   54.00 -37.00  90.00   98
  5  \w     28.00 126.00   1.00    8.00    --   54.00  37.00 150.00   98
  6  \w    -18.00  80.00   1.00    8.00    --   54.00 -37.00   0.00   98
  7  \w    -18.00  80.00   1.00    8.00    --   54.00 -37.00 -90.00   98
  8  \w      1.00  96.00   1.00    8.00    --   54.00 -99.00   0.00   95
  9  \w     35.00 125.00   1.00    8.00    --   54.00-147.00-103.00   90
 10  \w     33.00 123.00   1.00    8.00    --   54.00  57.00-120.00   90
 11  \w    100.00 178.00   1.00    8.00    --  108.00 111.00  30.00   78
 12  \w     36.00 146.00   1.00    8.00    --  108.00 -91.00  60.00  110
 13  \w     57.00 151.00   1.00    8.00    --  108.00 178.00  30.00   94
 14  \w     36.00 116.00   1.00    8.00    --  108.00-111.00-180.00   80
 15  \w     35.00 178.00   1.00    8.00    --  108.00 -12.00  60.00  143
 16  \w     40.00 130.00   1.00    8.00    --  108.00 -63.00 -30.00   90
 17  \w     35.00 142.00   1.00    8.00    --  108.00 -25.00 -30.00  107
 18  \w     57.00 151.00   1.00    8.00    --  108.00 178.00 -30.00   94
 19  \w     36.00 116.00   1.00    8.00    --  108.00-111.00   0.00   80
 20  \w    100.00 178.00   1.00    8.00    --  108.00 111.00-120.00   78
 21  \w     36.00 134.00   1.00    8.00    --  108.00 -37.00  90.00   98
 22  \w     36.00 134.00   1.00    8.00    --  108.00 -37.00 -60.00   98
 23  \w    -39.00  26.00   1.00    2.00    --    0.00  94.00  65.00   65
 24  \w    -57.00  -1.00   1.00    2.00    --    0.00 124.00 141.00   56
 25  \w     24.00 124.00   1.00    8.00    --   54.00  77.00  30.00  100
 26  \w     24.00 124.00   1.00    8.00    --   54.00  77.00 150.00  100
 27  \w    -15.00  75.00   1.00    8.00    --   54.00 -57.00-120.00   90
 28  \w     24.00 124.00   1.00    8.00    --   54.00  77.00 -60.00  100
;
_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      -0.0745152000
_diffrn_orient_matrix_UB_12      0.0426779000
_diffrn_orient_matrix_UB_13      -0.0722572000
_diffrn_orient_matrix_UB_21      -0.0290959000
_diffrn_orient_matrix_UB_22      -0.2124247000
_diffrn_orient_matrix_UB_23      -0.0120900000
_diffrn_orient_matrix_UB_31      -0.1659812000
_diffrn_orient_matrix_UB_32      0.0179143000
_diffrn_orient_matrix_UB_33      0.0297190000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12361
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.535
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.1835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3812
_reflns_number_total             4125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc01227j2.cif
_cod_data_source_block           jhc1707
_cod_depositor_comments
'Adding full bibliography for 7230738--7230745.cif.'
_cod_database_code               7230739
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C13 H11 N1 O5'
_chemical_oxdiff_usercomment     'Liam Hughes lmh4NO'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C16(H16A,H16B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C20(H20), C22(H22), C23(H23),
 C25(H25), C26(H26)
;
_shelx_res_checksum              29295
_olex2_date_sample_data_collection 2017-04-24
_olex2_exptl_crystal_mounting_method 'oil on 100 micrometre micromount'
_olex2_submission_original_sample_id lmh4NO
_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 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.885