Cyanthiwigin Natural Product Core as a Complex Molecular Scaffold for Comparative Late-Stage C-H Functionalization Studies.
Kim, Kelly E.; Adams, Ashley M.; Chiappini, Nicholas D.; Du Bois, J.; Stoltz, Brian M.; The Journal of organic chemistry 83 (2018) 3023–3033; doi:10.1021/acs.joc.7b03291

data_4033463
_publ_section_title
;
 Cyanthiwigin Natural Product Core as a Complex Molecular Scaffold for
 Comparative Late-Stage C-H Functionalization Studies.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3023
_journal_page_last               3033
_journal_paper_doi               10.1021/acs.joc.7b03291
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H26 O2'
_chemical_formula_weight         262.38
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.507(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4497(4)
_cell_length_b                   6.4699(3)
_cell_length_c                   12.5564(6)
_cell_measurement_reflns_used    6105
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.47
_cell_measurement_theta_min      3.57
_cell_volume                     757.14(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX3 v2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8282
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.508
_diffrn_reflns_theta_min         3.569
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.044
_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). 
 Bayesian Statistics 
 Student_T Nu      100 
 Select Pairs     1357 
 Theta_Min ..     7.73 
 Theta_Max ..    74.33 
 P2(true)....    1.000 
 P3(true)....    1.000 
 P3(rac-twin)  0.9E-06 
 P3(false) ..  0.7E-18 
 G ..........   1.4872 
 G (su) .....   0.2667 
 Hooft y ... -0.24(13) 
;
_refine_ls_abs_structure_Flack   -0.23(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0434P)^2^+0.0815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2814
_reflns_number_total             3039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03291_si_002.cif
_cod_data_source_block           P16423
_cod_depositor_comments          'Adding full bibliography for 4033463.cif.'
_cod_database_code               4033463
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.826
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              94765
_shelx_hkl_checksum              1543