Synthesis of the ABC Substructure of Brevenal by Sequential exo-Mode Oxacyclizations of Acyclic Polyene Precursors.
Hurtak, Jessica A.; McDonald, Frank E.; Organic letters 19 (2017) 6036–6039; doi:10.1021/acs.orglett.7b02538

data_1547824
_publ_section_title
;
 Synthesis of the ABC Substructure of Brevenal by Sequential exo-Mode
 Oxacyclizations of Acyclic Polyene Precursors.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6036
_journal_page_last               6039
_journal_paper_doi               10.1021/acs.orglett.7b02538
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H25 I O5'
_chemical_formula_sum            'C15 H25 I O5'
_chemical_formula_weight         412.25
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-07-04
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.06.08 svn.r3296 for OlexSys, GUI svn.r5188)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.02693(17)
_cell_length_b                   11.10793(17)
_cell_length_c                   14.3797(3)
_cell_measurement_reflns_used    22130
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.2680
_cell_measurement_theta_min      1.8360
_cell_volume                     1601.59(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -6.76 199.24   0.50   10.00    --   31.63  73.80 109.24  412
  2  \w     -6.76 199.24   0.50   10.00    --   31.63  73.80  19.24  412
  3  \w     -6.76 199.24   0.50   10.00    --   31.63  73.80 154.24  412
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0701475000
_diffrn_orient_matrix_UB_12      -0.0036229000
_diffrn_orient_matrix_UB_13      -0.0058092000
_diffrn_orient_matrix_UB_21      0.0016749000
_diffrn_orient_matrix_UB_22      -0.0515886000
_diffrn_orient_matrix_UB_23      0.0290626000
_diffrn_orient_matrix_UB_31      -0.0089783000
_diffrn_orient_matrix_UB_32      -0.0374254000
_diffrn_orient_matrix_UB_33      -0.0394476000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20884
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         2.317
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.021
_exptl_absorpt_correction_T_max  0.33311
_exptl_absorpt_correction_T_min  0.31215
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Spherical absorption correction using equivalent radius and absorption coefficient. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.322
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 2085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4889
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0238
_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^)+(0.0391P)^2^+0.8084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0613
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4848
_reflns_number_total             4889
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02538_si_003.cif
_cod_data_source_block           jah-11-102
_cod_depositor_comments
'Adding full bibliography for 1547823--1547824.cif.'
_cod_database_code               1547824
_chemical_oxdiff_formula         C15H25IO5
_cell_oxdiff_angle_alpha         89.9650(11)
_cell_oxdiff_angle_beta          89.9235(11)
_cell_oxdiff_angle_gamma         89.9425(11)
_cell_oxdiff_length_a            10.02693(14)
_cell_oxdiff_length_b            11.11111(15)
_cell_oxdiff_length_c            14.3756(2)
_cell_oxdiff_measurement_reflns_used 22130
_cell_oxdiff_volume              1601.59(4)
_shelx_estimated_absorpt_t_max   0.563
_shelx_estimated_absorpt_t_min   0.317
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 O5-H5
 0.975 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C7(H7), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C15(H15A,H15B), C11(H11A,H11B), C3(H3A,H3B), C14(H14A,H14B),
 C1(H1A,H1B), C4(H4A,H4B)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id JAH-11-102
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.385
_oxdiff_exptl_absorpt_empirical_full_min 0.773
_shelx_res_checksum              6241
_shelx_hkl_checksum              78399