A Concise Synthesis of the Naphthalene Portion of Purpuromycin
Andrew N. Lowell; Michael W. Fennie; Marisa C. Kozlowski; Journal of Organic Chemistry 73 (2008) 1911–1918; doi:10.1021/jo7024114

data_4023318
_publ_section_title
;
 A Concise Synthesis of the Naphthalene Portion of Purpuromycin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1911
_journal_page_last               1918
_journal_paper_doi               10.1021/jo7024114
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C23 H24 O7'
_chemical_formula_weight         412.42
_chemical_melting_point          121.5(5)
_chemical_name_common
' Cpd 2: 3-(Benzyloxy)-1,4,5,6,8-pentamethoxynaphthalene-2-carbaldehyde '
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.162(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4788(14)
_cell_length_b                   19.010(3)
_cell_length_c                   12.1060(19)
_cell_measurement_temperature    143(1)
_cell_volume                     2020.3(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0895
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7701
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.828
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0344P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                1789
_reflns_number_total             3543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7024114-File001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '121-122' was changed to '121.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_database_code               4023318