Synthesis of (−)-Melodinine K: A Case Study of Efficiency in Natural Product Synthesis
Walia, Manish; Teijaro, Christiana N.; Gardner, Alex; Tran, Thi; Kang, Jinfeng; Zhao, Senzhi; O’Connor, Sarah E.; Courdavault, Vincent; Andrade, Rodrigo B.; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00310

data_1558691
_publ_section_title
;
 Synthesis of (&#x2212;)-Melodinine K: A Case Study of Efficiency in
 Natural Product Synthesis
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00310
_journal_year                    2020
_chemical_formula_moiety         'C30 H38 N2 O4 S2'
_chemical_formula_sum            'C30 H38 N2 O4 S2'
_chemical_formula_weight         554.74
_chemical_melting_point          ?
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 113.499(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5202(18)
_cell_length_b                   14.868(3)
_cell_length_c                   10.981(2)
_cell_measurement_reflns_used    4005
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.812
_cell_measurement_theta_min      2.333
_cell_volume                     1425.4(5)
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_collection       'COSMO (Bruker-AXS)'
_computing_data_reduction        'SADABS (Bruker-AXS)'
_computing_molecular_graphics    XP
_computing_publication_material  'APEX2 Report Generator (Bruker-AXS)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Kappa APEX II DUO'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9972
_diffrn_reflns_point_group_measured_fraction_full 0.807
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.051
_diffrn_reflns_theta_min         2.022
_diffrn_source                   'fine-focused sealed tube'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
9995 Corrected reflections written to file mo_3095_0m.hkl
 Estimated minimum and maximum transmission:  0.6007  0.7456
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  0.2000
 Lambda/2 correction factor = 0.00150
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_description       bar
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5240
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0354P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.492
_reflns_Friedel_fraction_full    0.607
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                4471
_reflns_number_total             5240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00310_si_002.cif
_cod_data_source_block           mo_3095_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not determined' was
changed to '?' -- the value is undefined or not given.

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

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1558691
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              1056
_shelx_hkl_checksum              2834