Total Synthesis of the Ammosamides
Chambers C. Hughes; William Fenical; Journal of the American Chemical Society 132 (2010) 2528–2529; doi:10.1021/ja9106572

data_4101979
_publ_section_title
;
 Total Synthesis of the Ammosamides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2528
_journal_page_last               2529
_journal_paper_doi               10.1021/ja9106572
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C9 H5 Cl N2 O4'
_chemical_formula_weight         240.60
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.73(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.596(11)
_cell_length_b                   13.08(2)
_cell_length_c                   11.167(18)
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    94(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      3.11
_cell_volume                     943(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      94(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10352
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.63
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.9418
_exptl_absorpt_correction_T_min  0.8550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       Plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.3555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                1452
_reflns_number_total             1766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9106572_si_002.cif
_cod_data_source_block           sio16_0m
_cod_original_cell_volume        944(3)
_cod_database_code               4101979