Genome Mining of Alkaloidal Terpenoids from a Hybrid Terpene and Nonribosomal Peptide Biosynthetic Pathway.
Yee, Danielle A.; Kakule, Thomas B.; Cheng, Wei; Chen, Mengbin; Chong, Christine T. Y.; Hai, Yang; Hang, Leibniz F.; Hung, Yiu-Sun; Liu, Nicholas; Ohashi, Masao; Okorafor, Ikechukwu C.; Song, Yongxiang; Tang, ManCheng; Zhang, Zhuan; Tang, Yi; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b13046

data_4133895
_publ_section_title
;
 Genome Mining of Alkaloidal Terpenoids from a Hybrid Terpene and
 Nonribosomal Peptide Biosynthetic Pathway.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13046
_journal_year                    2019
_chemical_formula_moiety         'C15 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.34
_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
_audit_creation_date             2019-09-03
_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            4
_cell_length_a                   9.1845(2)
_cell_length_b                   11.3146(2)
_cell_length_c                   12.5358(3)
_cell_measurement_reflns_used    9642
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.37
_cell_measurement_theta_min      5.27
_cell_volume                     1302.71(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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_temperature      100.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14701
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.299
_diffrn_reflns_theta_min         5.266
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 971 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0429P)^2^+0.3003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2370
_reflns_number_total             2424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13046_si_002.cif
_cod_data_source_block           cu_tang1703s
_cod_database_code               4133895
_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:
 C2(H1), C5(H4), C8(H9), C7(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3(H2A,H2B), C4(H3A,H3B), C10(H6A,H6B), C11(H7A,H7B), C9(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C15(H13A,H13B,H13C), C13(H14A,H14B,H14C), C14(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              72719
_shelx_hkl_checksum              11268
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'