Syntheses of chloroisosulochrin and isosulochrin and biomimetic elaboration to maldoxin, maldoxone, dihydromaldoxin, and dechlorodihydromaldoxin.
Yu, Min; Snider, Barry B.; Organic letters 13 (2011) 4224–4227; doi:10.1021/ol201561w

data_1502326
_publ_section_title
;
 Syntheses of chloroisosulochrin and isosulochrin and biomimetic
 elaboration to maldoxin, maldoxone, dihydromaldoxin, and
 dechlorodihydromaldoxin.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4224
_journal_page_last               4227
_journal_paper_doi               10.1021/ol201561w
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C17 H14 O8'
_chemical_formula_sum            'C17 H14 O8'
_chemical_formula_weight         346.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_audit_creation_date             11-04-30
_audit_creation_method           CRYSTALS_ver_14.15
_cell_angle_alpha                79.872(2)
_cell_angle_beta                 85.732(2)
_cell_angle_gamma                61.496(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1082(3)
_cell_length_b                   8.1290(3)
_cell_length_c                   12.9822(5)
_cell_measurement_reflns_used    7493
_cell_measurement_temperature    120
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     740.19(5)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14011
_diffrn_reflns_theta_full        27.145
_diffrn_reflns_theta_max         27.984
_diffrn_reflns_theta_min         1.593
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'plate fragment'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.652
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0193
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.0050108
_refine_ls_shift/su_mean         0.0011483
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.36P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0937
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0937
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3436
_reflns_number_total             3552
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.80
_oxford_diffrn_Wilson_scale      13.75
_oxford_refine_ls_r_factor_ref   0.0376
_oxford_refine_ls_scale          0.2616(2)
_oxford_reflns_number_all        3552
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ym8_143_2_0m in P-1'
_cod_data_source_file            ol201561w_si_002.cif
_cod_data_source_block           ym8_143_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_primary' value 'Other' changed to
'other' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1502326
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE O   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,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) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,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                                                                             
;