Total Synthesis of (-)-Carinatine A and (+)-Lycopladine A.
Meng, Lingxing; The Journal of organic chemistry 81 (2016) 7784–7789; doi:10.1021/acs.joc.6b01435

data_4037085
_publ_section_title
;
 Total Synthesis of (-)-Carinatine A and (+)-Lycopladine A.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7784
_journal_page_last               7789
_journal_paper_doi               10.1021/acs.joc.6b01435
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H22 O3'
_chemical_formula_sum            'C16 H22 O3'
_chemical_formula_weight         262.33
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.141(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.946(2)
_cell_length_b                   11.256(3)
_cell_length_c                   8.207(2)
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.01
_cell_measurement_theta_min      2.53
_cell_volume                     720.2(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7046
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.441
_diffrn_reflns_theta_min         2.529
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0742 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.7396. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0690P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                3468
_reflns_number_total             4082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01435_si_003.cif
_cod_data_source_block           mo_dm15450_0m
_cod_original_cell_volume        720.3(3)
_cod_database_code               4037085
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C8(H8A,H8B), C10(H10A,H10B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'