Divergent Total Syntheses of Rhodomyrtosones A and B.
Gervais, Anais; Lazarski, Kiel E.; Porco, Jr, John A; The Journal of organic chemistry 80 (2015) 9584–9591; doi:10.1021/acs.joc.5b01570

data_4036328
_publ_section_title
;
 Divergent Total Syntheses of Rhodomyrtosones A and B.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9584
_journal_page_last               9591
_journal_paper_doi               10.1021/acs.joc.5b01570
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C26 H36 O7'
_chemical_formula_sum            'C26 H36 O7'
_chemical_formula_weight         460.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.23 svn.r3118 for OlexSys, GUI svn.r4973)
;
_audit_update_record
;
2015-02-02 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 94.903(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9488(3)
_cell_length_b                   11.2504(3)
_cell_length_c                   20.0504(5)
_cell_measurement_reflns_used    8058
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.347
_cell_measurement_theta_min      4.053
_cell_volume                     2460.74(11)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 (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  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  Montel
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9339
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.985
_diffrn_reflns_theta_max         66.985
_diffrn_reflns_theta_min         4.052
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.86422
_exptl_absorpt_correction_T_min  0.77250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1299 before and 0.0609 after correction.
 The Ratio of minimum to maximum transmission is 0.89.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 81434 reflections, Rint = 0.0517
 (35678 with I > 3sig(I), Rint = 0.0476)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         9339
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1032P)^2^+0.7826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6243
_reflns_number_total             9339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01570_si_002.cif
_cod_data_source_block           twin4
_cod_database_code               4036328
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9334(6) 0.0666(6)
2. 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
3. Restrained distances
 C12A-C11A = C16-C11A = C4-C11A
 1.54 with sigma of 0.02
 C12B-C11B = C16-C11B = C4-C11B
 1.54 with sigma of 0.02
 C4-C12A
 2.52 with sigma of 0.04
 C4-C16
 2.52 with sigma of 0.04
 C16-C12A
 2.52 with sigma of 0.04
 C4-C12B
 2.52 with sigma of 0.04
 C16-C12B
 2.52 with sigma of 0.04
 C16-C4
 2.52 with sigma of 0.04
4. Rigid bond restraints
 C11A, C12A, C13A, C14A, C14B, C11B, C12B, C13B, C15B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C11A \\sim C12A \\sim C13A \\sim C15A \\sim C14A: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
C11B \\sim C12B \\sim C13B \\sim C15B \\sim C14B: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
Uanis(C11A) \\sim Ueq, Uanis(C11B) \\sim Ueq, Uanis(C12B) \\sim Ueq,
Uanis(C12A) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C13B) \\sim Ueq,
Uanis(C14A) \\sim Ueq, Uanis(C15B) \\sim Ueq, Uanis(C15A) \\sim Ueq,
Uanis(C14B) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C11B) = Uanis(C11A)
6. Others
 Sof(C24B)=Sof(H24B)=Sof(C25B)=Sof(H25D)=Sof(H25E)=Sof(H25F)=Sof(C23B)=
 Sof(H23C)=Sof(H23D)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=
 Sof(H25B)=Sof(H25C)=Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
 Sof(C12B)=Sof(H12C)=Sof(H12D)=Sof(C13B)=Sof(H13B)=Sof(C11B)=Sof(H11B)=
 Sof(C14B)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C15B)=Sof(H15D)=Sof(H15E)=
 Sof(H15F)=1-FVAR(2)
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(H13A)=
 Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C14A)=Sof(H14A)=Sof(H14B)=
 Sof(H14C)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C11A(H11A), C24A(H24A), C13A(H13A), C13B(H13B), C11B(H11B), C24B(H24B)
7.b Secondary CH2 refined with riding coordinates:
 C23A(H23A,H23B), C12A(H12A,H12B), C12B(H12C,H12D), C23B(H23C,H23D)
7.c Aromatic/amide H refined with riding coordinates:
 C20(H20)
7.d Idealised Me refined as rotating group:
 C25A(H25A,H25B,H25C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C26A(H26A,H26B,
 H26C), C15A(H15A,H15B,H15C), C14A(H14A,H14B,H14C), C8(H8A,H8B,H8C), C7(H7A,H7B,
 H7C), C14B(H14D,H14E,H14F), C15B(H15D,H15E,H15F), C25B(H25D,H25E,H25F),
 C26B(H26D,H26E,H26F)
7.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O5(H5), O6(H6)
;
_shelx_res_checksum              25751
_shelx_hkl_checksum              6054
_olex2_submission_special_instructions 'No special instructions were received'