Formal Total Synthesis of Actinoranone: Synthesis Approaches and Cytotoxic Studies.
Novaes, Luiz F. T.; Gonçalves, Kaliandra de Almeida; Trivella, Daniela B. B.; Pastre, Julio C.; The Journal of organic chemistry 83 (2018) 5160–5176; doi:10.1021/acs.joc.8b00514

data_4035525
_publ_section_title
;
 Formal Total Synthesis of Actinoranone: Synthesis Approaches and
 Cytotoxic Studies.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5160
_journal_page_last               5176
_journal_paper_doi               10.1021/acs.joc.8b00514
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H33 N O3'
_chemical_formula_sum            'C18 H33 N O3'
_chemical_formula_weight         311.47
_chemical_name_systematic
2-((1R,2S,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-N-methoxy-N-methylacetamide
_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_Int_Tables_number      4
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-04-12 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 110.710(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7535(5)
_cell_length_b                   6.9720(3)
_cell_length_c                   12.6570(6)
_cell_measurement_reflns_used    5258
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.812
_cell_measurement_theta_min      3.733
_cell_volume                     887.62(7)
_computing_cell_refinement       'SAINT v8.34A (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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.8520
_diffrn_measured_fraction_theta_max 0.8520
_diffrn_measurement_device_type  'Bruker Apex CCD Detector'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6361
_diffrn_reflns_theta_full        67.9856
_diffrn_reflns_theta_max         67.99
_diffrn_reflns_theta_min         3.73
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1380 before and 0.0483 after correction. The Ratio of minimum to maximum transmission is 0.8525. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1653
_exptl_crystal_description       needle
_exptl_crystal_F_000             345.0250
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.2170
_refine_diff_density_min         -0.2105
_refine_diff_density_rms         0.0650
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.15(17)
_refine_ls_d_res_high            0.8315
_refine_ls_d_res_low             11.8391
_refine_ls_goodness_of_fit_ref   0.9079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9079
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.735
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              8
_reflns_limit_k_min              -7
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                2682
_reflns_number_total             2757
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b00514_si_002.cif
_cod_data_source_block           cu_17JAN09_LUIZ_FER_LN223_Cr5_0m
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               4035525
_olex2_refinement_description
;
;
_olex2_submission_original_sample_id LN223
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;