Biomimetic Synthesis of Mitchellenes B-H from the Abundant Biological Precursor 14-Hydroxy-6,12-muuroloadien-15-oic Acid.
Klepp, Julian; Sadgrove, Nicholas J.; Legendre, Sarah V. A.-M.; Sumby, Christopher J.; Greatrex, Ben W.; The Journal of organic chemistry 84 (2019) 9637–9647; doi:10.1021/acs.joc.9b00961

data_4034401
_publ_section_title
;
 Biomimetic Synthesis of Mitchellenes B-H from the Abundant Biological
 Precursor 14-Hydroxy-6,12-muuroloadien-15-oic Acid.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9637
_journal_page_last               9647
_journal_paper_doi               10.1021/acs.joc.9b00961
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 O2'
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_weight         234.32
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   8.21878(12)
_cell_length_b                   15.8290(2)
_cell_length_c                   29.2661(4)
_cell_measurement_reflns_used    20160
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      29.1970
_cell_measurement_theta_min      3.6950
_cell_volume                     3807.38(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1695
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.942
_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    -45.00  52.50   0.75    5.43    --  -19.50  37.00 -30.00  130
  2  \w    -92.00  25.00   0.75    5.43    --  -19.50 -19.00   0.00  156
  3  \w    -54.00  45.00   0.75    5.43    --   18.95 -37.00  90.00  132
  4  \w     32.00  95.00   0.75    5.43    --   18.95-178.00 -60.00   84
  5  \w     32.00  95.00   0.75    5.43    --   18.95-178.00 120.00   84
  6  \w     -2.00  88.00   0.75    5.43    --   18.95  57.00-120.00  120
  7  \w    -25.00  21.50   0.75    5.43    --  -19.50 -99.00 -60.00   62
  8  \w    -25.00  21.50   0.75    5.43    --  -19.50 -99.00 120.00   62
  9  \w    -25.00  60.50   0.75    5.43    --   18.95 -99.00  90.00  114
 10  \w    -25.00  48.50   0.75    5.43    --   18.95 -99.00 -60.00   98
 11  \w    -88.00   2.00   0.75    5.43    --  -19.50 -57.00 -60.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0263385000
_diffrn_orient_matrix_UB_12      -0.0303107000
_diffrn_orient_matrix_UB_13      -0.0162561000
_diffrn_orient_matrix_UB_21      -0.0632525000
_diffrn_orient_matrix_UB_22      -0.0276024000
_diffrn_orient_matrix_UB_23      0.0069758000
_diffrn_orient_matrix_UB_31      -0.0524933000
_diffrn_orient_matrix_UB_32      0.0180708000
_diffrn_orient_matrix_UB_33      -0.0165691000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            68028
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.345
_diffrn_reflns_theta_min         3.488
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 3455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         9588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0472P)^2^+0.6668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.881
_reflns_number_gt                8654
_reflns_number_total             9588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00961_si_002.cif
_cod_data_source_block           15a
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3807.37(9)
_cod_original_formula_moiety     '3(C15 H22 O2)'
_cod_original_formula_sum        'C45 H66 O6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     702.97
_cod_database_code               4034401
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C15H22O2
_chemical_oxdiff_usercomment     'Dihydro mitchellene B'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.55
_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.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C4A(H4A), C4B(H4B), C4C(H4C), C5A(H5A),
 C5B(H5B), C5C(H5C), C6A(H6A), C6B(H6B), C6C(H6C), C7A(H7A), C7B(H7B), C7C(H7C),
  C10A(H10A), C10B(H10B), C10C(H10C), C12A(H12A), C12B(H12B), C12C(H12C),
 C14A(H14A), C14B(H14B), C14C(H14C)
2.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2B(H2BA,H2BB), C2C(H2CA,H2CB), C3A(H3AA,H3AB), C3B(H3BA,
 H3BB), C3C(H3CA,H3CB), C8A(H8AA,H8AB), C8B(H8BA,H8BB), C8C(H8CA,H8CB),
 C9A(H9AA,H9AB), C9B(H9BA,H9BB), C9C(H9CA,H9CB)
2.c Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C11B(H11D,H11E,H11F), C11C(H11G,H11H,H11I), C13A(H13A,
 H13B,H13C), C13B(H13D,H13E,H13F), C13C(H13G,H13H,H13I)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.070
_oxdiff_exptl_absorpt_empirical_full_min 0.928