A Concise Enantioselective Synthesis and Cytotoxic Evaluation of the Anticancer Rotenoid Deguelin Enabled by a Tandem Knoevenagel/Conjugate Addition/Decarboxylation Sequence.
Farmer, Rebecca L.; Scheidt, Karl A.; Chemical science (Royal Society of Chemistry : 2010) 4 (2013) 3304–3309; doi:10.1039/C3SC50424G

data_1514761
_publ_section_title
;
 A Concise Enantioselective Synthesis and Cytotoxic Evaluation of the
 Anticancer Rotenoid Deguelin Enabled by a Tandem Knoevenagel/Conjugate
 Addition/Decarboxylation Sequence.
;
_journal_issue                   8
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              3304
_journal_page_last               3309
_journal_paper_doi               10.1039/C3SC50424G
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.27380(10)
_cell_length_b                   11.20700(10)
_cell_length_c                   19.0373(2)
_cell_measurement_temperature    100(2)
_cell_volume                     2191.93(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43646
_diffrn_reflns_theta_full        30.23
_diffrn_reflns_theta_max         30.23
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9519
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.2704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                2664
_reflns_number_total             3245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc50424g.txt
_cod_data_source_block           n0680_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               1514761