Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class.
Lu, Hai-Hua; Pronin, Sergey V.; Antonova-Koch, Yevgeniya; Meister, Stephan; Winzeler, Elizabeth A.; Shenvi, Ryan A.; Journal of the American Chemical Society 138 (2016) 7268–7271; doi:10.1021/jacs.6b03899

data_4130475
_publ_section_title
;
 Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial
 Activity of the Isocyanoterpene Class.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7268
_journal_page_last               7271
_journal_paper_doi               10.1021/jacs.6b03899
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H30 O2'
_chemical_formula_sum            'C19 H30 O2'
_chemical_formula_weight         290.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-12-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.16840(10)
_cell_length_b                   17.2700(4)
_cell_length_c                   36.9053(8)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.114
_cell_measurement_theta_min      2.825
_cell_volume                     3294.10(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.10-0 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            36814
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.266
_diffrn_reflns_theta_min         2.394
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1526 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.9056.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2398 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0518P)^2^+0.6039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5846
_reflns_number_total             6024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03899_si_003.cif
_cod_data_source_block           shenvi62
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4130475
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C17(H17),
 C5'(H5'), C6'(H6'), C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12'), C15'(H15'),
 C17'(H17')
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C13(H13A,H13B), C14(H14A,H14B),
 C18(H18A,H18B), C3'(H3'A,H3'B), C4'(H4'A,H4'B), C8'(H8'A,H8'B), C13'(H13C,
 H13D), C14'(H14C,H14D), C18'(H18C,H18D)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C19(H19A,H19B,H19C), C1'(H1'A,H1'B,H1'C),
 C7'(H7'A,H7'B,H7'C), C19'(H19D,H19E,H19F)
;
_shelx_res_checksum              21482
_shelx_hkl_checksum              67455
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'