A concise synthesis of herbertenolide
Hu, Jiadong; Ji, Kai; Yan, Lihong; Yang, Siyu; Li, Yin; Wen, Wen; Chen, Le; Wu, Xiaohui; Hu, Youcai; Xie, Weiqing; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00041E

data_7158533
_publ_section_title
;
 A concise synthesis of herbertenolide
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00041E
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-06 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.30150(10)
_cell_length_b                   11.6303(2)
_cell_length_c                   28.2622(3)
_cell_measurement_reflns_used    34618
_cell_measurement_temperature    172.97(13)
_cell_measurement_theta_max      74.2760
_cell_measurement_theta_min      4.0900
_cell_volume                     2399.99(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      172.97(13)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_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    -72.00 -20.00   1.00    1.00    --    0.00 -57.00  60.00   52
  2  \w    -30.00  80.00   1.00    1.00    --    0.00  77.00 -60.00  110
  3  \w    -22.00  29.00   1.00    1.00    --    0.00  57.00 150.00   51
  4  \w     43.00  72.00   1.00    1.00    --    0.00  57.00 150.00   29
  5  \w    -24.00  26.00   1.00    1.00    --    0.00  19.00  60.00   50
  6  \w    -24.00  84.00   1.00    1.00    --    0.00  19.00 -90.00  108
  7  \w    -44.00  23.00   1.00    1.00    --    0.00 -57.00 120.00   67
  8  \w    -12.00  22.00   1.00    1.00    --    0.00 -57.00  60.00   34
  9  \w    -30.00  89.00   1.00    1.00    --    0.00  77.00  60.00  119
 10  \w     50.00  75.00   1.00    1.00    --    0.00  19.00  60.00   25
 11  \w    107.00 133.00   1.00    1.00    --   95.80  68.00   0.88   26
 12  \w    125.00 180.00   1.00    1.00    --   95.80  80.00-106.68   55
 13  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  73.91   25
 14  \w    101.00 175.00   1.00    1.00    --   95.80  82.00  73.91   74
 15  \w     64.00  94.00   1.00    1.00    --   95.80  80.00-106.68   30
 16  \w     68.00 101.00   1.00    1.00    --   95.80  68.00   0.88   33
 17  \w     72.00 185.00   1.00    1.00    --   95.80  59.00 -10.51  113
 18  \w    110.00 185.00   1.00    1.00    --   95.80  74.00 139.46   75
 19  \w     82.00 127.00   1.00    1.00    --   95.80 -82.00-120.00   45
 20  \w     37.00 102.00   1.00    1.00    --   95.80 -61.00-180.00   65
 21  \w     66.00  92.00   1.00    1.00    --   95.80  77.00-120.00   26
 22  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 23  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 24  \w    144.00 180.00   1.00    1.00    --   95.80  82.00-180.00   36
 25  \w     66.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00   62
 26  \w     30.00 126.00   1.00    1.00    --   95.80 -82.00  90.00   96
 27  \w     65.00 102.00   1.00    1.00    --   95.80  77.00 -90.00   37
 28  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 29  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 30  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 31  \w     66.00  91.00   1.00    1.00    --   95.80  74.00 139.46   25
 32  \w    153.00 184.00   1.00    1.00    --   95.80  74.00-124.92   31
 33  \w     43.00 127.00   1.00    1.00    --   95.80 -82.00 171.84   84
 34  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 35  \w     75.00 185.00   1.00    1.00    --   95.80  45.00-120.00  110
 36  \w    137.00 173.00   1.00    1.00    --   95.80  63.00  39.87   36
 37  \w     75.00 102.00   1.00    1.00    --   95.80  45.00 150.00   27
 38  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 39  \w     66.00 169.00   1.00    1.00    --   95.80  74.00 -42.65  103
 40  \w     65.00 165.00   1.00    1.00    --   95.80  77.00 150.00  100
 41  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 43  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 44  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 45  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-150.00   26
 46  \w     77.00 114.00   1.00    1.00    --   95.80 -77.00  30.00   37
 47  \w     76.00 184.00   1.00    1.00    --   95.80  45.00-150.00  108
 48  \w     70.00 132.00   1.00    1.00    --   95.80  63.00  39.87   62
 49  \w     65.00  91.00   1.00    1.00    --   95.80  82.00-120.00   26
 50  \w     71.00 108.00   1.00    1.00    --   95.80  61.00 150.00   37
 51  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 150.00   26
 52  \w     96.00 183.00   1.00    1.00    --   95.80  82.00  90.00   87
 53  \w     65.00 173.00   1.00    1.00    --   95.80  78.00  47.31  108
 54  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 55  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 56  \w    143.00 173.00   1.00    1.00    --   95.80  68.00   0.88   30
 57  \w     66.00  91.00   1.00    1.00    --   95.80  74.00-124.92   25
 58  \w     69.00 172.00   1.00    1.00    --   95.80  65.00 -56.66  103
 59  \w     43.00 104.00   1.00    1.00    --   95.80 -82.00  30.00   61
 60  \w     71.00  97.00   1.00    1.00    --   95.80  61.00  90.00   26
 61  \w     71.00  96.00   1.00    1.00    --   95.80  59.00-158.82   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0213272000
_diffrn_orient_matrix_UB_12      0.0100364000
_diffrn_orient_matrix_UB_13      0.0540596000
_diffrn_orient_matrix_UB_21      0.2098795000
_diffrn_orient_matrix_UB_22      0.0040877000
_diffrn_orient_matrix_UB_23      0.0053682000
_diffrn_orient_matrix_UB_31      -0.0047078000
_diffrn_orient_matrix_UB_32      0.1320359000
_diffrn_orient_matrix_UB_33      -0.0043187000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            54055
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.110
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0372P)^2^+0.5088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4179
_reflns_number_total             4292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00041e2.cif
_cod_data_source_block           exp_2527
_cod_database_code               7158533
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.822
_shelx_estimated_absorpt_t_min   0.765
_reflns_odcompleteness_completeness 99.88
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C22(H22A,H22B), C23(H23A,H23B),
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C16(H16), C17(H17), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_shelx_res_checksum              3363
_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 609.711
_oxdiff_exptl_absorpt_empirical_full_min 0.353