Total Synthesis of (±)-Hyphodermins A and D
Wendy A. Loughlin; Ian D. Jenkins; Luke C. Henderson; Marc R. Campitelli; Peter C. Healy; Journal of Organic Chemistry 73 (2008) 3435–3440; doi:10.1021/jo800227p

data_4023394
_publ_section_title
;
 Total Synthesis of (+-)-Hyphodermins A and D
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3435
_journal_page_last               3440
_journal_paper_doi               10.1021/jo800227p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C16 H17 Br O5'
_chemical_formula_sum            'C16 H17 Br O5'
_chemical_formula_weight         369.20
_chemical_name_systematic
; 
1-(ethoxycarbonyl)-7-bromo-5,6,7,8-tetrahydro-5,6-dimethyl-8-oxonapthelene
-2-carboxylic acid

;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.915(6)
_cell_length_b                   19.022(10)
_cell_length_c                   10.736(5)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    295
_cell_measurement_theta_max      16.8
_cell_measurement_theta_min      12.6
_cell_volume                     3250(3)
_computing_cell_refinement       'MSC/AFC7 Diffractometer Control (MSC, 1999)'
_computing_data_collection       'MSC/AFC7 Diffractometer Control (MSC, 1999)'
_computing_data_reduction        'teXsan for Windows (MSC, 2001)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material
'teXsan for Windows (MSC, 2001); PLATON (Spek, 2003)'
_computing_structure_refinement
'teXsan for Windows (MSC, 2001); SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'teXsan for Windows (MSC, 2001)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Rigaku AFC7R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0763
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3697
_diffrn_reflns_reduction_process ' ?'
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0.66
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.549
_exptl_absorpt_correction_T_max  0.568
_exptl_absorpt_correction_T_min  0.515
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+5.4504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1621
_reflns_number_gt                1582
_reflns_number_total             2861
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo800227p-File003_1.cif
_cod_data_source_block           13_850wl69_LH6-90
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4023394