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_4032221
_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 ad
_chemical_compound_source        local
_chemical_formula_moiety         'C7 H11 I O4, H2 O'
_chemical_formula_sum            'C7 H13 I O5'
_chemical_formula_weight         304.08
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-08-22
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-08-23 - Report on C7 H13 I1 O5
            by Anthony C. Willis
            for  Ehab Taher and Martin Banwell

2013-08-23 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 120.5922(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8154(8)
_cell_length_b                   4.5652(2)
_cell_length_c                   15.7010(8)
_cell_measurement_reflns_used    46057
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1037.53(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 0.992
_diffrn_measured_fraction_theta_max 0.989
_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  0.056
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10233
_diffrn_reflns_theta_full        29.507
_diffrn_reflns_theta_max         30.110
_diffrn_reflns_theta_min         2.814
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.077
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.72
_refine_diff_density_min         -1.02
_refine_ls_abs_structure_details 'Flack (1983), 1331 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         3020
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.0013642
_refine_ls_shift/su_mean         0.0001512
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 3.78P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0734
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0734
_reflns_limit_h_max              20
_reflns_limit_h_min              -23
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2812
_reflns_number_total             3024
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.80
_oxford_diffrn_Wilson_scale      5.17
_oxford_refine_ls_r_factor_ref   0.0339
_oxford_refine_ls_scale          0.4973(7)
_oxford_reflns_number_all        3020
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1360 At 12:20 on 22/ 8/13'
_cod_data_source_file            jo6b02372_si_006.cif
_cod_data_source_block           ban1360
_cod_original_sg_symbol_Hall     'C 2y '
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_database_code               4032221
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O   (   2,X'S) H   ( 921,X'S) 
RIDE O   (   3,X'S) H   ( 931,X'S) 
RIDE O   (   5,X'S) H   ( 951,X'S) H   ( 952,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   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,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                                                                             
;