Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.
Khatri, Hem Raj; Bhattarai, Bijay; Kaplan, Will; Li, Zhongzheng; Curtis Long, Marcus John; Aye, Yimon; Nagorny, Pavel; Journal of the American Chemical Society 141 (2019) 4849–4860; doi:10.1021/jacs.8b12870

data_4129024
_publ_section_title
;
 Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of
 Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of
 Oxygenation.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4849
_journal_page_last               4860
_journal_paper_doi               10.1021/jacs.8b12870
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H34 O7'
_chemical_formula_sum            'C23 H34 O7'
_chemical_formula_weight         422.50
_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   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.3143(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.36657(8)
_cell_length_b                   9.85708(14)
_cell_length_c                   14.28520(19)
_cell_measurement_reflns_used    9574
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.7710
_cell_measurement_theta_min      3.0900
_cell_volume                     1034.35(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15889
_diffrn_reflns_point_group_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.499
_diffrn_reflns_theta_min         3.102
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 1177 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 

Space Group       P21
Wavelength    1.54184
Flack x .... -0.01(14)
Parsons z ..  -0.02(9)
 
 
Bijvoet Pairs    1268
Coverage ...       70
DiffCalcMax.    20.46
Outlier Crit    40.91
Scatter Plot
Sigma Crit..     0.25
Select Pairs      146
Number Plus        89
Number Minus       57
Aver. Ratio     1.080
Slope ......    1.193
 
 
Student-T Prob. Plot
Sample Size.     1258
Corr. Coeff.    0.997
Intercept ..    0.129
Slope ......    1.109
 
 
Bayesian Statistics
Student_T Nu     7.59
Select Pairs     1268
P2(true)....    1.000
P3(true)....    1.000
P3(rac-twin)  0.8E-06
P3(false) ..  0.2E-23
G ..........   1.0169
G (su) .....   0.1914
Hooft y .... -0.01(10)

;
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0623P)^2^+0.2678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_full    0.712
_reflns_Friedel_fraction_max     0.700
_reflns_number_gt                3233
_reflns_number_total             3311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12870_si_006.cif
_cod_data_source_block           hk3169
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129024
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.894
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              21181
_shelx_hkl_checksum              62309