A short synthesis of (±)-antroquinonol in an unusual scaffold of 4-hydroxy-2-cyclohexenone.
Hsu, Che-Sheng; Chou, Ho-Hsuan; Fang, Jim-Min; Organic & biomolecular chemistry 13 (2015) 5510–5519; doi:10.1039/c5ob00411j

data_7154399
_publ_section_title
;
 A short synthesis of (+-)-antroquinonol in an unusual scaffold of
 4-hydroxy-2-cyclohexenone.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5510
_journal_page_last               5519
_journal_paper_doi               10.1039/c5ob00411j
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_audit_update_record
;
2014-11-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                73.977(7)
_cell_angle_beta                 81.811(6)
_cell_angle_gamma                78.873(7)
_cell_formula_units_Z            2
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_cell_length_b                   8.4612(7)
_cell_length_c                   13.1167(9)
_cell_measurement_reflns_used    1817
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      74.3710
_cell_measurement_theta_min      5.5140
_cell_volume                     727.84(10)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0228
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_diffrn_reflns_limit_k_max       10
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_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4603
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_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+0.1055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                2010
_reflns_number_total             2643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00411j2.cif
_cod_data_source_block           ic16473
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

 Adding full bibliography for 7154396--7154401.cif.
;
_cod_original_cell_volume        727.84(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7154399