Progress toward the Total Synthesis of N-Methylwelwitindolinone B Isothiocyanate.
Cleary, Leah; Pitzen, Jennifer; Brailsford, John A.; Shea, Kenneth J.; Organic letters 16 (2014) 4460–; doi:10.1021/ol5020043

data_1517386
_publ_section_title
;
 Progress toward the Total Synthesis of N-Methylwelwitindolinone B
 Isothiocyanate.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4460
_journal_paper_doi               10.1021/ol5020043
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C22 H27 N O5'
_chemical_formula_weight         385.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                67.5035(6)
_cell_angle_beta                 80.6214(6)
_cell_angle_gamma                86.2284(6)
_cell_formula_units_Z            4
_cell_length_a                   9.6052(5)
_cell_length_b                   14.5858(7)
_cell_length_c                   14.9637(7)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      28.99
_cell_measurement_theta_min      2.43
_cell_volume                     1910.97(16)
_computing_cell_refinement       'Bruker SAINT 8.18c, 2012'
_computing_data_collection       'Bruker APEX2 2012.4-0, 2012'
_computing_data_reduction        'Bruker SAINT 8.18c, 2012'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013/3 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL 2008/4'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23634
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
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_diffrn_reflns_theta_min         1.674
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.282
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         9320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.7591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8191
_reflns_number_total             9320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5020043_si_002.cif
_cod_data_source_block           kjs74
_cod_depositor_comments
;Adding full bibliography for 1517385--1517386.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1517386
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.974
_shelxl_version_number           2013-3
_shelx_res_checksum              32844
_shelx_hkl_checksum              1158