"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_1547607
_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         'C25 H35 N3 O'
_chemical_formula_sum            'C25 H35 N3 O'
_chemical_formula_weight         393.56
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.04476(8)
_cell_length_b                   13.48040(17)
_cell_length_c                   26.4744(3)
_cell_measurement_reflns_used    6063
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3240
_cell_measurement_theta_min      4.6690
_cell_volume                     2157.29(5)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9882
_diffrn_measured_fraction_theta_max 0.9599
_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   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00  30.00   98
  2  \w    -33.00  65.00   1.00    1.00    --   40.98 -37.00 150.00   98
  3  \w     35.00 136.00   1.00    1.00    --  106.95 -61.00-150.00  101
  4  \w     79.00 178.00   1.00    1.00    --  106.95  30.00  30.00   99
  5  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 -90.00   84
  6  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 -60.00   85
  7  \w     34.00 109.00   1.00    1.00    --  106.95-125.00 120.00   75
;
_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      0.1333283000
_diffrn_orient_matrix_UB_12      -0.0971577000
_diffrn_orient_matrix_UB_13      0.0026709000
_diffrn_orient_matrix_UB_21      -0.0343819000
_diffrn_orient_matrix_UB_22      -0.0036130000
_diffrn_orient_matrix_UB_23      0.0576190000
_diffrn_orient_matrix_UB_31      -0.2144520000
_diffrn_orient_matrix_UB_32      -0.0600881000
_diffrn_orient_matrix_UB_33      -0.0076399000
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8487
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.480
_diffrn_reflns_theta_min         3.679
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74932
_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    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1655 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0612P)^2^+0.2917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                4075
_reflns_number_total             4187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf7b03126_si_003.cif
_cod_data_source_block           exp_176
_cod_depositor_comments
'Adding full bibliography for 1547607--1547608.cif.'
_cod_original_cell_volume        2157.28(5)
_cod_database_code               1547607
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.847
_reflns_odcompleteness_completeness 98.82
_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, All N(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:
 C6(H6), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C15(H15A,H15B), C4(H4A,H4B), C8(H8A,H8B), C2(H2C,H2D), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C25(H25), C24(H24), C22(H22), C17(H17), C23(H23)
2.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C12(H12A,H12B,
 H12C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_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 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.690