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_4034399
_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      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             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                 100.178(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4256(8)
_cell_length_b                   5.0334(3)
_cell_length_c                   12.3473(8)
_cell_measurement_reflns_used    4468
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      27.5420
_cell_measurement_theta_min      3.5640
_cell_volume                     637.74(8)
_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 0.993
_diffrn_measured_fraction_theta_max 0.938
_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    -13.00  87.00   1.00   25.00    --   16.75  77.00-120.00  100
  2  \w    -13.00  87.00   1.00   25.00    --   16.75  77.00  60.00  100
  3  \w    -13.00  87.00   1.00   25.00    --   16.75  77.00-150.00  100
  4  \w    -47.00  53.00   1.00   25.00    --  -17.30  77.00 -30.00  100
  5  \w    -47.00  53.00   1.00   25.00    --  -17.30  77.00-120.00  100
  6  \w    -47.00  53.00   1.00   25.00    --  -17.30  77.00  60.00  100
  7  \w     -5.00  86.00   1.00   25.00    --   16.75  57.00   0.00   91
  8  \w    -56.00  43.00   1.00   25.00    --   16.75 -37.00 120.00   99
  9  \w    -25.00  25.00   1.00   25.00    --  -17.30 -99.00  90.00   50
 10  \w    -38.00  52.00   1.00   25.00    --  -17.30  57.00 -60.00   90
 11  \w    -25.00  25.00   1.00   25.00    --  -17.30 -99.00 -60.00   50
 12  \w    -25.00  59.00   1.00   25.00    --   16.75 -99.00  30.00   84
 13  \w    -25.00  59.00   1.00   25.00    --   16.75 -99.00-150.00   84
 14  \w     35.00  93.00   1.00   25.00    --   16.75 178.00-150.00   58
 15  \w    -56.00  90.00   1.00   25.00    --   16.75   0.00-180.00  146
 16  \w    -38.00  52.00   1.00   25.00    --  -17.30  57.00 -30.00   90
 17  \w    -56.00 -13.00   1.00   25.00    --   16.75   0.00-120.00   43
 18  \w    -56.00  90.00   1.00   25.00    --   16.75   0.00-150.00  146
;
_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      -0.0586738000
_diffrn_orient_matrix_UB_12      -0.0059235000
_diffrn_orient_matrix_UB_13      0.0214833000
_diffrn_orient_matrix_UB_21      -0.0100928000
_diffrn_orient_matrix_UB_22      -0.1324266000
_diffrn_orient_matrix_UB_23      -0.0192467000
_diffrn_orient_matrix_UB_31      0.0351811000
_diffrn_orient_matrix_UB_32      -0.0479075000
_diffrn_orient_matrix_UB_33      0.0507127000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20319
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         28.437
_diffrn_reflns_theta_min         3.353
_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  0.90449
_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    1.220
_exptl_crystal_description       needle
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0362P)^2^+0.1166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                2546
_reflns_number_total             2936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00961_si_002.cif
_cod_data_source_block           10
_cod_original_cell_volume        637.73(8)
_cod_database_code               4034399
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C17H13O2
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C14(H14A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C15(H15)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O14(H14)
;
_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 1.117
_oxdiff_exptl_absorpt_empirical_full_min 0.921