Chemoenzymatic total synthesis of the phytotoxic geranylcyclohexentriol (-)-phomentrioloxin.
Ma, Xinghua; Banwell, Martin G.; Willis, Anthony C.; Journal of natural products 76 (2013) 1514–1518; doi:10.1021/np4002866

data_1512271
_publ_section_title
;
 Chemoenzymatic total synthesis of the phytotoxic geranylcyclohexentriol
 (-)-phomentrioloxin.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              1514
_journal_page_last               1518
_journal_paper_doi               10.1021/np4002866
_journal_volume                  76
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C19 H35 I O4 Si'
_chemical_formula_sum            'C19 H35 I O4 Si'
_chemical_formula_weight         482.47
_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             12-10-03
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-10-04 - Report on C19 H35 I O4 Si 
             by Anthony C. Willis
             for   Xinghua Ma and Martin Banwell

2012-10-04 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1171(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5122(2)
_cell_length_b                   15.1148(2)
_cell_length_c                   16.0879(3)
_cell_measurement_reflns_used    30386
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2.6
_cell_volume                     2313.03(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.045
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            53779
_diffrn_reflns_theta_full        30.003
_diffrn_reflns_theta_max         30.003
_diffrn_reflns_theta_min         2.695
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.454
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.641
_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    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.08
_refine_diff_density_min         -1.25
_refine_ls_abs_structure_details 'Flack (1983), 6493 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.024(11)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9766
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         13460
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.0215548
_refine_ls_shift/su_mean         0.0005576
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.26P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0790
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0790
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              21
_reflns_limit_k_min              -21
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                10768
_reflns_number_total             13460
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.32
_oxford_diffrn_Wilson_scale      8.36
_oxford_refine_ls_r_factor_ref   0.0508
_oxford_refine_ls_scale          0.3949(2)
_oxford_reflns_number_all        13460
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '10021501 ban1234a'
_cod_data_source_file            np4002866_si_003.cif
_cod_data_source_block           ban1234a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               1512271
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, I(1,U'S) UNTIL C(33) 
CONT C(34,U'S,OCC) UNTIL C(36) 
CONT C(37,U'S) UNTIL C(39) 
CONT C(341,U'S,OCC) UNTIL C(361) 
CONT ENANTIO 
EQUIV C(34,OCC) UNTIL C(36) C(341,OCC) UNTIL C(361) 
WEIGHT -1 C(341,OCC) UNTIL C(361) 
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   (   8,X'S) H   (  81,X'S) H   (  82,X'S) H   (  83,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) H   (  93,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,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) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) H   ( 283,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) H   ( 293,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) H   ( 303,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) H   ( 333,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) H   ( 353,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) H   ( 363,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) H   ( 383,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 392,X'S) H   ( 393,X'S) 
RIDE C   (  341,X'S) H   ( 3411,X'S) 
RIDE C   (  351,X'S) H   ( 3511,X'S) H   ( 3512,X'S) H   ( 3513,X'S) 
RIDE C   (  361,X'S) H   ( 3611,X'S) H   ( 3612,X'S) H   ( 3613,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 1.88, .02 = SI(2) TO C(34), SI(2) TO C(341) 
DIST 1.54, .02 = C(34) TO C(35), C(34) TO C(36) 
CONT  C(341) TO C(351), C(341) TO C(361) 
ANGLE 111, 2. = C(35) TO C(34) TO C(36), C(351) TO C(341) TO C(361) 
ANGLE 114, 2. = SI(2) TO C(34) TO C(35), SI(2) TO C(34) TO C(36) 
ANGLE 114, 2. = SI(2) TO C(341) TO C(351), SI(2) TO C(341) TO C(361) 
REM 
U(IJ) 0.0, .01 = C(34) TO C(341) 
U(IJ) 0.0, .01 = C(35) TO C(351) 
U(IJ) 0.0, .01 = C(36) TO C(361) 
VIBR 0.0, .01 = C(341) TO C(351), C(341) TO C(351) 
REM 
LIMIT C(361,Y) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;