Stereochemical Assignment of Strigolactone Analogues Confirms Their Selective Biological Activity.
Artuso, Emma; Ghibaudi, Elena; Lace, Beatrice; Marabello, Domenica; Vinciguerra, Daniele; Lombardi, Chiara; Koltai, Hinanit; Kapulnik, Yoram; Novero, Mara; Occhiato, Ernesto G.; Scarpi, Dina; Parisotto, Stefano; Deagostino, Annamaria; Venturello, Paolo; Mayzlish-Gati, Einav; Bier, Ariel; Prandi, Cristina; Journal of natural products 78 (2015) 2624–2633; doi:10.1021/acs.jnatprod.5b00557

data_1540425
_publ_section_title
;
 Stereochemical Assignment of Strigolactone Analogues Confirms Their
 Selective Biological Activity.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2624
_journal_page_last               2633
_journal_paper_doi               10.1021/acs.jnatprod.5b00557
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H14 N O4'
_chemical_formula_sum            'C18 H14 N O4'
_chemical_formula_weight         308.30
_chemical_name_systematic
;(R,E)-4-methyl-2-((4-methyl-5-oxo-2,5-
dihydrofuran-2-yloxy)methylene-1,2-dihydrocyclopenta[b]indol-3(4H)-one'
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.8797(9)
_cell_length_b                   17.320(2)
_cell_length_c                   26.023(3)
_cell_measurement_reflns_used    1417
_cell_measurement_temperature    295
_cell_measurement_theta_max      50.4260
_cell_measurement_theta_min      9.6880
_cell_volume                     3100.8(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega   49.00   78.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000   90.0000 29

  2 omega   -3.00   55.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000 -180.0000 58

  3 omega    6.00   33.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000   90.0000 27

  4 omega  -76.00  -50.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.6882   70.0000  161.7485 26

  5 omega   -3.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882  -70.0000   93.3293 89

  6 omega  -13.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882  -70.0000   46.6653 104

  7 omega   49.00   90.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882  -70.0000 -157.0082 41

  8 omega   37.00  126.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882   37.0000    0.0000 89

  9 omega   57.00   92.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882  -70.0000  131.8447 35

 10 omega   41.00   88.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882  -69.0000  -51.6868 47

 11 omega   55.00  135.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882   37.0000  -90.0000 80

 12 omega  -13.00   22.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882  -70.0000 -157.0082 35

 13 omega    0.00   56.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882  -37.0000   90.0000 56

 14 omega   56.00   81.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       60.6882  -70.0000 -112.8550 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0700102000
_diffrn_orient_matrix_UB_12      -0.0176517000
_diffrn_orient_matrix_UB_13      0.0549901000
_diffrn_orient_matrix_UB_21      0.1347990000
_diffrn_orient_matrix_UB_22      0.0634330000
_diffrn_orient_matrix_UB_23      0.0210821000
_diffrn_orient_matrix_UB_31      -0.1646374000
_diffrn_orient_matrix_UB_32      0.0597220000
_diffrn_orient_matrix_UB_33      -0.0061932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_laue_measured_fraction_full 0.975
_diffrn_reflns_laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4252
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        51.507
_diffrn_reflns_theta_max         51.507
_diffrn_reflns_theta_min         9.733
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       plank
_exptl_crystal_F_000             1288
_exptl_crystal_recrystallization_method
;
Slow evaporation of a methanol solution
;
_exptl_crystal_size_max          0.1596
_exptl_crystal_size_mid          0.0627
_exptl_crystal_size_min          0.0211
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         1634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0566
_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^)+(0.1052P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1828
_reflns_Friedel_coverage         0.681
_reflns_friedel_fraction_full    0.934
_reflns_friedel_fraction_max     0.932
_reflns_number_gt                1250
_reflns_number_total             1634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np5b00557_si_002.cif
_cod_data_source_block           ego10_x2
_cod_depositor_comments          'Adding full bibliography for 1540425.cif.'
_cod_original_cell_volume        3100.7(7)
_cod_database_code               1540425
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C8(H8), C16(H16), C2(H2), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C5(H5A,H5B,H5C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-16
_olex2_submission_special_instructions 'No special instructions were received'