"Carbon Assimilation" Inspired Design and Divergent Synthesis of Drimane Meroterpenoid Mimics as Novel Fungicidal Leads.
Zhang, Shasha; Li, Dangdang; Song, Zehua; Zang, Chuanli; Zhang, Lu; Song, Xiushi; Li, Shengkun; Journal of agricultural and food chemistry 65 (2017) 9013–9021; doi:10.1021/acs.jafc.7b03126

data_1547608
_publ_section_title
;
 &quot;Carbon Assimilation&quot; Inspired Design and Divergent Synthesis
 of Drimane Meroterpenoid Mimics as Novel Fungicidal Leads.
;
_journal_issue                   41
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              9013
_journal_page_last               9021
_journal_paper_doi               10.1021/acs.jafc.7b03126
_journal_volume                  65
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H35 N O2'
_chemical_formula_sum            'C24 H35 N O2'
_chemical_formula_weight         369.53
_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     direct
_audit_creation_date             2016-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4847(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.67127(7)
_cell_length_b                   7.05127(7)
_cell_length_c                   15.44464(12)
_cell_measurement_reflns_used    12790
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4260
_cell_measurement_theta_min      5.2600
_cell_volume                     1051.296(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9288
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00-120.00  101
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00   0.00  100
  3  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00  90.00  100
  4  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00   0.00   98
  5  \w     23.00  97.00   1.00    1.00    --   40.98-125.00 120.00   74
  6  \w     13.00 113.00   1.00    1.00    --   40.98  57.00  60.00  100
  7  \w      8.00 117.00   1.00    1.00    --   40.98  77.00 -30.00  109
  8  \w     23.00  97.00   1.00    1.00    --   40.98-125.00-150.00   74
  9  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 -90.00   85
 10  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -90.00  100
 11  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -30.00  104
 12  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  30.00  100
 13  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -90.00  104
 14  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  90.00  104
 15  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -60.00  100
 16  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -60.00  104
 17  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 -30.00   85
 18  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  30.00  104
 19  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -30.00  100
 20  \w     78.00 178.00   1.00    1.00    --  106.95  61.00   0.00  100
 21  \w     74.00 178.00   1.00    1.00    --  106.95  77.00   0.00  104
 22  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  60.00  100
 23  \w     81.00 178.00   1.00    1.00    --  106.95  45.00   0.00   97
 24  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  30.00   97
 25  \w     81.00 171.00   1.00    1.00    --  106.95  45.00 -60.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1486479000
_diffrn_orient_matrix_UB_12      0.0787996000
_diffrn_orient_matrix_UB_13      0.0099507000
_diffrn_orient_matrix_UB_21      0.0131421000
_diffrn_orient_matrix_UB_22      -0.0205128000
_diffrn_orient_matrix_UB_23      -0.0984582000
_diffrn_orient_matrix_UB_31      -0.0565119000
_diffrn_orient_matrix_UB_32      0.2027771000
_diffrn_orient_matrix_UB_33      -0.0138730000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15303
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.619
_diffrn_reflns_theta_min         4.581
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1595 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3930
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0740P)^2^+0.1158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.889
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                3897
_reflns_number_total             3930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf7b03126_si_002.cif
_cod_data_source_block           exp_177
_cod_depositor_comments
'Adding full bibliography for 1547607--1547608.cif.'
_cod_database_code               1547608
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.840
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C10(H10), C6(H6), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C2(H2A,H2B), C17(H17A,H17B), C4(H4A,H4B), C8(H8A,
 H8B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C24(H24), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C13(H13A,H13B,
 H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.558
_oxdiff_exptl_absorpt_empirical_full_min 0.374