Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?
Barton, Naomi A.; Marsh, Benjamin J.; Lewis, William; Narraidoo, Nathalie; Seymour, Graham B.; Fray, Rupert; Hayes, Christopher J.; Chem. Sci. 7 (2016) 3102–; doi:10.1039/C5SC03463A

data_1542318
_publ_section_title
;
 Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the
 taxol biosynthetic pathway?
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3102
_journal_paper_doi               10.1039/C5SC03463A
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H32 O2'
_chemical_formula_sum            'C20 H32 O2'
_chemical_formula_weight         304.45
_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     iterative
_audit_creation_date             2014-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-10-24 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1378(3)
_cell_length_b                   11.3745(2)
_cell_length_c                   13.5667(3)
_cell_measurement_reflns_used    12745
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      77.1368
_cell_measurement_theta_min      3.2548
_cell_volume                     1718.72(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -65.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   38.0000  150.0000 90

  2 omega   22.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   42.0000  -68.0000 79

  3 omega   38.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127 -125.0000   60.0000 41

  4 omega   42.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -150.0000 33

  5 omega   43.00   71.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   60.0000 28

  6 omega   41.00   71.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000    0.0000 30

  7 omega   46.00   73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 27

  8 omega   90.00  135.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  120.0000 45

  9 omega   72.00  142.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000 -150.0000 70

 10 omega   82.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -30.0000 25

 11 omega  117.00  156.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -30.0000 39

 12 omega   77.00  130.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000    0.0000    0.0000 53

 13 omega   42.00   70.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   90.0000 28

 14 omega   93.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000   60.0000 27

 15 omega   90.00  157.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -150.0000 67

 16 omega   43.00   74.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -42.0000 -111.0000 31

 17 omega  122.00  147.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  111.0000  -60.0000 25

 18 omega  104.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  -30.0000 40

 19 omega   41.00   77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  120.0000 36

 20 omega   51.00   78.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -20.0000  168.0000 27

 21 omega   99.00  131.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -20.0000  168.0000 32

 22 omega   66.00  110.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -112.0000  111.0000 44

 23 omega   72.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  120.0000 25

 24 omega  133.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  120.0000 25

 25 omega   59.00   98.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -58.0000  -80.0000 39

 26 omega  100.00  126.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -60.0000 26

 27 omega   53.00   79.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -120.0000    2.0000 26

 28 omega   93.00  138.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -66.0000   28.0000 45

 29 omega   48.00   74.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -66.0000   28.0000 26

 30 omega -113.00  -54.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127 -155.0000  116.0000 59

 31 omega   20.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   54.0000  167.0000 92

 32 omega   14.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   77.0000  -60.0000 101

 33 omega    2.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127 -125.0000   30.0000 96

 34 omega   14.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   77.0000   30.0000 101

 35 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -120.0000 77

 36 omega   89.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -30.0000 69

 37 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000    0.0000 77

 38 omega   41.00   77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -60.0000 36

 39 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -150.0000 77

 40 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   60.0000 77

 41 omega   80.00   86.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   79.0000  111.0000 6
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0979634000
_diffrn_orient_matrix_UB_12      0.0750827000
_diffrn_orient_matrix_UB_13      -0.0496098000
_diffrn_orient_matrix_UB_21      -0.0962831000
_diffrn_orient_matrix_UB_22      -0.0882174000
_diffrn_orient_matrix_UB_23      0.0342779000
_diffrn_orient_matrix_UB_31      -0.0161048000
_diffrn_orient_matrix_UB_32      0.0701880000
_diffrn_orient_matrix_UB_33      0.0962320000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18845
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.347
_diffrn_reflns_theta_min         5.074
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2915
_exptl_crystal_size_mid          0.2064
_exptl_crystal_size_min          0.2002
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0734P)^2^+0.3065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3555
_reflns_number_total             3624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc03463a2.cif
_cod_data_source_block           nhcjhb
_cod_depositor_comments          'Adding full bibliography for 1542318.cif.'
_cod_original_cell_volume        1718.73(7)
_cod_database_code               1542318
_nottingham_internal_coll_name   NHCJHB
_nottingham_internal_coll_number 10024
_nottingham_internal_coll_client NH/CJH
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.6 and 6.4s'
_nottingham_internal_coll_frame_width '1 degree'
_nottingham_internal_coll_user   wl
_nottingham_internal_coll_date   4/1/2011
_nottingham_internal_process_date 05/01/2011
_nottingham_internal_process_user wl
_nottingham_internal_solution_date 5/1/2011
_nottingham_internal_solution_user WL
_nottingham_internal_refinement_date 7/1/2011
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_date 24/10/2014
_nottingham_internal_validation_user WL
_nottingham_internal_archive_date 24/10/2011
_chemical_oxdiff_formula         'C20 H32 O2'
_chemical_oxdiff_usercomment
'NHCJHB #10024 IN FOMBLIN FILM ON MICROMOUNT FOR NH/CJH'
_reflns_odcompleteness_completeness 93.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_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:
 C1(H1), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,
 H13B), C14(H14A,H14B)
2.c X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              45928
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'