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_1512270
_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 unk
_chemical_compound_source        local
_chemical_formula_moiety         'C17 H24 O4'
_chemical_formula_sum            'C17 H24 O4'
_chemical_formula_weight         292.38
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             13-02-04
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2013-02-04 - Report on C17 H24 O4 
             by Anthony C. Willis
             for   Xinghua Ma and Martin Banwell

2013-02-04 - passes checkcif tests with warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.619(4)
_cell_length_b                   11.969(9)
_cell_length_c                   29.55(2)
_cell_measurement_reflns_used    61613
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1634(2)
_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    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.95
_diffrn_measured_fraction_theta_max 0.899
_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  0.114
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5080
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         2.678
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.965
_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    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.72
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1950
_refine_ls_R_factor_gt           0.1214
_refine_ls_shift/su_max          0.0347697
_refine_ls_shift/su_mean         0.0101760
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ +11.82P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2917
_refine_ls_wR_factor_gt          0.2353
_refine_ls_wR_factor_ref         0.2917
_reflns_limit_h_max              5
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                880
_reflns_number_total             1601
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.49
_oxford_diffrn_Wilson_scale      3.11
_oxford_refine_ls_r_factor_ref   0.1950
_oxford_refine_ls_scale          0.781(8)
_oxford_reflns_number_all        1599
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'using CCDC 872237's coords'
_cod_data_source_file            np4002866_si_002.cif
_cod_data_source_block           ban1305a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 21 21 21 '
_cod_database_code               1512270
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE O   (   1,X'S) H   ( 901,X'S) 
RIDE O   (   2,X'S) H   ( 902,X'S) 
RIDE O   (   3,X'S) H   ( 903,X'S) 
RIDE C   (   1,X'S) H   ( 162,X'S) 
RIDE C   (   2,X'S) H   ( 163,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   (   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) 
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   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,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                                                                             
;