Uncovering biosynthetic relationships between antifungal nonadrides and octadrides
de Mattos-Shipley, Kate M. J.; Spencer, Catherine E.; Greco, Claudio; Heard, David M.; O'Flynn, Daniel E.; Dao, Trong T.; Song, Zhongshu; Mulholland, Nicholas P.; Vincent, Jason L.; Simpson, Thomas J.; Cox, Russell J.; Bailey, Andrew M.; Willis, Christine L.; Chemical Science  (2020) –; doi:10.1039/D0SC04309E

data_1559298
_publ_section_title
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 Uncovering biosynthetic relationships between antifungal nonadrides and
 octadrides
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04309E
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H28 O7'
_chemical_formula_sum            'C22 H28 O7'
_chemical_formula_weight         404.44
_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             2020-06-22
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-06-22 deposited with the CCDC.	2020-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0210(2)
_cell_length_b                   10.0682(2)
_cell_length_c                   29.3914(7)
_cell_measurement_reflns_used    5410
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.088
_cell_measurement_theta_min      2.452
_cell_volume                     2373.56(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            21576
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.936
_diffrn_reflns_theta_min         2.138
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0723 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.8675.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.408
_exptl_crystal_size_min          0.226
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         5685
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0695P)^2^+0.8984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4779
_reflns_number_total             5685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04309e2.cif
_cod_data_source_block           16_scy5_sq
_cod_database_code               1559298
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C14-C13 \\sim C14A-C13 \\sim C15A-C14A \\sim C15-C14 \\sim C16-C15 \\sim
C16A-C15A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C14A \\sim C15A \\sim C14 \\sim C16A \\sim C16 \\sim C15: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C16) \\sim Ueq, Uanis(C16A) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
Uanis(C21) \\sim Ueq, Uanis(C21A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C21A) = Uanis(C21)
4. Others
 Fixed Sof: H13A(0.6409) H13B(0.6409) H13C(0.3591) H13D(0.3591) C14(0.6409)
 H14A(0.6409) H14B(0.6409) C15(0.6409) H15A(0.6409) H15B(0.6409) C16(0.6409)
 H16A(0.6409) H16B(0.6409) H16C(0.6409) H20A(0.47598) H20B(0.47598)
 H20C(0.52402) H20D(0.52402) C21(0.47598) H21A(0.47598) H21B(0.47598)
 C22(0.47598) H22A(0.47598) H22B(0.47598) H22C(0.47598) C21A(0.52402)
 H21C(0.52402) H21D(0.52402) C22A(0.52402) H22D(0.52402) H22E(0.52402)
 H22F(0.52402) C14A(0.3591) H14C(0.3591) H14D(0.3591) C15A(0.3591) H15C(0.3591)
 H15D(0.3591) C16A(0.3591) H16D(0.3591) H16E(0.3591) H16F(0.3591)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B),
 C13(H13C,H13D), C14(H14A,H14B), C15(H15A,H15B), C19(H19A,H19B), C20(H20A,H20B),
  C20(H20C,H20D), C21(H21A,H21B), C21A(H21C,H21D), C14A(H14C,H14D), C15A(H15C,
 H15D)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F), C16A(H16D,
 H16E,H16F)
5.d Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_shelx_res_checksum              63448
_shelx_fab_checksum              89945
_olex2_submission_special_instructions 'No special instructions were received'