Antroquinonol A: Scalable Synthesis and Preclinical Biology of a Phase 2 Drug Candidate.
Villaume, Matthew T.; Sella, Eran; Saul, Garrett; Borzilleri, Robert M.; Fargnoli, Joseph; Johnston, Kathy A.; Zhang, Haiying; Fereshteh, Mark P.; Dhar, T. G. Murali; Baran, Phil S.; ACS central science 2 (2016) 27–31; doi:10.1021/acscentsci.5b00345

data_4516748
_publ_section_title
;
 Antroquinonol A: Scalable Synthesis and Preclinical Biology of a Phase 2
 Drug Candidate.
;
_journal_issue                   1
_journal_name_full               'ACS central science'
_journal_page_first              27
_journal_page_last               31
_journal_paper_doi               10.1021/acscentsci.5b00345
_journal_volume                  2
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H22 O5'
_chemical_formula_sum            'C14 H22 O5'
_chemical_formula_weight         270.31
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.160(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9867(7)
_cell_length_b                   13.6517(15)
_cell_length_c                   8.5379(9)
_cell_measurement_reflns_used    6848
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.194
_cell_measurement_theta_min      5.221
_cell_volume                     692.35(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 APEX'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9241
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.188
_diffrn_reflns_theta_min         5.221
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1054 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.6923.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       Block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0396P)^2^+0.0812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0743
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2464
_reflns_number_total             2497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            oc5b00345_si_001.cif
_cod_data_source_block           baran480
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4516748
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.881
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C10(H10A,H10B), C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              54850
_shelx_hkl_checksum              23337
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'