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_4032079
_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 H22 O4'
_chemical_formula_sum            'C17 H22 O4'
_chemical_formula_weight         290.36
_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
_audit_creation_date             14-10-08
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-10-08 - C17 H22 O4
            by Anthony C. Willis
            for Ehab Taher and Martin Banwell

2014-10-08 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 90.035(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7176(2)
_cell_length_b                   11.7310(4)
_cell_length_c                   13.7171(6)
_cell_measurement_reflns_used    5702
_cell_measurement_temperature    150
_cell_measurement_theta_max      71
_cell_measurement_theta_min      5
_cell_volume                     759.13(5)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement
;
CRYSTALS (Betteridge et al., 2003)' 
PLATON (Spek, 2008)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.039
_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            10962
_diffrn_reflns_theta_full        71.497
_diffrn_reflns_theta_max         71.497
_diffrn_reflns_theta_min         4.961
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.22
_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   1.0058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1541
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0801
_refine_ls_shift/su_max          0.0197771
_refine_ls_shift/su_mean         0.0048445
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.16P)^2^ + 1.27P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2203
_refine_ls_wR_factor_gt          0.2202
_refine_ls_wR_factor_ref         0.2203
_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                1536
_reflns_number_total             1556
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.65
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0802
_oxford_refine_ls_scale          12(2)
_oxford_reflns_number_all        1541
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1453SN\Tony_ban1453SN_data At 10:20 on'
_cod_data_source_file            jo6b02372_si_002.cif
_cod_data_source_block           ban1453SN
_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               4032079
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE O   (   1,X'S) H   (   1,X'S) 
RIDE O   (   2,X'S) H   (   2,X'S) 
RIDE O   (   4,X'S) H   (   4,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) H   (  83,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,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                                                                             
;