(+)-Thalianatriene and (-)-Retigeranin B Catalyzed by Sesterterpene Synthases from Arabidopsis thaliana.
Shao, Jie; Chen, Qing-Wen; Lv, Hua-Jun; He, Juan; Liu, Zhi-Feng; Lu, Yan-Na; Liu, Hai-Li; Wang, Guo-Dong; Wang, Yong; Organic letters  (2017) –; doi:10.1021/acs.orglett.7b00586

data_1546604
_publ_section_title
;
 (+)-Thalianatriene and (-)-Retigeranin B Catalyzed by Sesterterpene
 Synthases from Arabidopsis thaliana.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b00586
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H40 O2'
_chemical_formula_sum            'C25 H40 O2'
_chemical_formula_weight         372.57
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5273)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.6640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0327(2)
_cell_length_b                   8.5099(2)
_cell_length_c                   13.3176(3)
_cell_measurement_reflns_used    9301
_cell_measurement_temperature    205
_cell_measurement_theta_max      71.16
_cell_measurement_theta_min      3.38
_cell_volume                     1124.05(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      205
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.991
_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       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13519
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        64.991
_diffrn_reflns_theta_max         64.991
_diffrn_reflns_theta_min         3.357
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1309 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.8589. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3453
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.1274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.802
_reflns_number_gt                3378
_reflns_number_total             3453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00586_si_002.cif
_cod_data_source_block           mm
_cod_database_code               1546604
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.904
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C10(H10), C12(H12), C14(H14), C18(H18), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C13(H13A,
 H13B), C16(H16A,H16B), C17(H17A,H17B)
2.c X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              56469
_shelx_hkl_checksum              45813
_olex2_submission_special_instructions 'No special instructions were received'