Harzianic acid, an antifungal and plant growth promoting metabolite from Trichoderma harzianum.
Vinale, Francesco; Flematti, Gavin; Sivasithamparam, Krishnapillai; Lorito, Matteo; Marra, Roberta; Skelton, Brian W.; Ghisalberti, Emilio L.; Journal of natural products 72 (2009) 2032–2035; doi:10.1021/np900548p

data_1503708
_publ_section_title
;
 Harzianic acid, an antifungal and plant growth promoting metabolite from
 Trichoderma harzianum.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2032
_journal_page_last               2035
_journal_paper_doi               10.1021/np900548p
_journal_volume                  72
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H27 N O6'
_chemical_formula_sum            'C19 H27 N O6'
_chemical_formula_weight         365.42
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-07-07T13:56:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.323(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5570(2)
_cell_length_b                   20.0101(4)
_cell_length_c                   7.6041(2)
_cell_measurement_reflns_used    15024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.0611
_cell_measurement_theta_min      4.4131
_cell_volume                     962.24(5)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1590348731
_diffrn_orient_matrix_UB_12      -0.0579238309
_diffrn_orient_matrix_UB_13      -0.0168998974
_diffrn_orient_matrix_UB_21      -0.1755628043
_diffrn_orient_matrix_UB_22      0.0443522027
_diffrn_orient_matrix_UB_23      -0.1181776
_diffrn_orient_matrix_UB_31      0.0574340729
_diffrn_orient_matrix_UB_32      -0.0246351387
_diffrn_orient_matrix_UB_33      -0.1730753214
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20616
_diffrn_reflns_theta_full        67.45
_diffrn_reflns_theta_max         67.45
_diffrn_reflns_theta_min         6.43
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Analytical numeric absorption correction using a multifaceted crystal
    model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.1443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                3349
_reflns_number_total             3396
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            np900548p_si_001.cif
_cod_data_source_block           fv1
_cod_original_sg_symbol_Hall     p_2yb
_cod_database_code               1503708