Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer
Noah Z. Burns; Irina N. Krylova; Rami N. Hannoush; Phil S. Baran; Journal of the American Chemical Society 131 (2009) 9172–9173; doi:10.1021/ja903745s

data_4104659
_publ_section_title
;
 Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its
 Atropisomer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9172
_journal_page_last               9173
_journal_paper_doi               10.1021/ja903745s
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C35 H33 N O4'
_chemical_formula_weight         531.62
_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                 108.383(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.538(7)
_cell_length_b                   28.664(19)
_cell_length_c                   9.364(6)
_cell_measurement_reflns_used    6286
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.64
_cell_volume                     2684(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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_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  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20579
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.10
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0087(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0680P)^2^+0.7473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1348
_reflns_number_gt                4193
_reflns_number_total             5161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903745s_si_003.cif
_cod_data_source_block           baran94
_cod_database_code               4104659