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_4104657
_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 H35 N O4'
_chemical_formula_weight         533.64
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0514(2)
_cell_length_b                   11.9665(2)
_cell_length_c                   29.3775(6)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.01
_cell_volume                     2830.44(10)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16912
_diffrn_reflns_theta_full        55.00
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_correction_T_min  0.8155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       rod
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(16)
_refine_ls_extinction_coef       0.00165(14)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.2390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                4754
_reflns_number_total             5019
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903745s_si_001.cif
_cod_data_source_block           baran79
_cod_database_code               4104657