Micromonohalimanes A and B: Antibacterial Halimane-Type Diterpenoids from a Marine Micromonospora Species
Zhang, Yan; Adnani, Navid; Braun, Doug R.; Ellis, Gregory A.; Barns, Kenneth J.; Parker-Nance, Shirley; Guzei, Ilia A.; Bugni, Tim S.; Journal of Natural Products  (2016) –; doi:10.1021/acs.jnatprod.6b00555

data_1544475
_publ_section_title
;
 Micromonohalimanes A and B: Antibacterial Halimane-Type Diterpenoids from
 a Marine Micromonospora Species
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.6b00555
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H34 O6, H2 O0.87, 0.13(O)'
_chemical_formula_sum            'C22 H36 O7'
_chemical_formula_weight         412.51
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.02.20 svn.r3157 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.987(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2381(5)
_cell_length_b                   6.9763(6)
_cell_length_c                   16.8910(8)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100
_cell_volume                     1088.43(12)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23887
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         73.398
_diffrn_reflns_theta_min         2.616
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.8920
_exptl_absorpt_correction_T_min  0.8209
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1629 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0541P)^2^+0.2072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                3959
_reflns_number_total             4036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00555_si_002.cif
_cod_data_source_block           bugni03
_cod_original_cell_volume        1088.43(13)
_cod_database_code               1544475
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.751
_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, All O(H,H) groups
2. Restrained distances
 O7-H7A = O7-H7B
 0.942 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uiso(O7A) = Uiso(O7B)
4. Others
 1*[Sof(O7)]+1*[Sof(O7A)]+1*[Sof(O7B)]=1 with esd of 0
5.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C16(H16), C20(H20)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C15(H15A,H15B),
 C18(H18A,H18B)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C),
 C22(H22A,H22B,H22C)
5.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'