The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents.
Taher, Ehab S.; Guest, Prue; Benton, Amanda; Ma, Xinghua; Banwell, Martin G.; Willis, Anthony C.; Seiser, Tobias; Newton, Trevor W.; Hutzler, Johannes; The Journal of organic chemistry 82 (2017) 211–233; doi:10.1021/acs.joc.6b02372

data_4032078
_publ_section_title
;
 The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation
 as Herbicidal Agents.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              211
_journal_page_last               233
_journal_paper_doi               10.1021/acs.joc.6b02372
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_compound_source        local
_chemical_formula_moiety         'C17 H20 O4'
_chemical_formula_sum            'C17 H20 O4'
_chemical_formula_weight         288.34
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             14-03-17
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-03-17 - Report on C17 H20 O4
            by Anthony C. Willis
            for  Ehab Taher and Martin Banwell

2014-03-17 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 90.470(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.6659(3)
_cell_length_b                   11.9898(9)
_cell_length_c                   13.6730(10)
_cell_measurement_reflns_used    16304
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     764.89(9)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8883
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_min         3.398
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details
;
The enantiomer has been assigned by reference to an unchanging chiral
centre in the synthetic procedure.
;
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0336
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1423
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.0042637
_refine_ls_shift/su_mean         0.0003903
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.18P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0832
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0832
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1295
_reflns_number_total             1423
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.19
_oxford_diffrn_Wilson_scale      0.60
_oxford_refine_ls_r_factor_ref   0.0414
_oxford_refine_ls_scale          1.298(9)
_oxford_reflns_number_all        1423
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1407 At 10: 0 on 17/ 3'
_cod_data_source_file            jo6b02372_si_001.cif
_cod_data_source_block           ban1407
_cod_depositor_comments
'Adding full bibliography for 4032077--4032079.cif.'
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4032078
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT H(1,X'S) UNTIL H(4) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;