Synthetic Approaches to the Microtubule-Stabilizing Sponge Alkaloid Ceratamine A and Desbromo Analogues
Matt Nodwell; Alban Pereira; Jenna L. Riffell; Carla Zimmerman; Brian O. Patrick; Michel Roberge; Raymond J. Andersen; Journal of Organic Chemistry 74 (2009) 995–1006; doi:10.1021/jo802322s

data_4024307
_publ_section_title
;
Synthetic Approaches to the Microtubule-Stabilizing Sponge Alkaloid
Ceratamine A and Desbromo Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              995
_journal_page_last               1006
_journal_paper_doi               10.1021/jo802322s
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C24 H22 Cl N3 O3'
_chemical_formula_weight         435.90
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.678(7)
_cell_angle_beta                 103.672(8)
_cell_angle_gamma                92.025(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8404(14)
_cell_length_b                   9.4642(16)
_cell_length_c                   13.031(2)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.58
_cell_volume                     1054.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26522
_diffrn_reflns_theta_full        28.08
_diffrn_reflns_theta_max         28.08
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.036(2)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.3104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                4184
_reflns_number_total             4994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802322s_si_001.cif
_cod_data_source_block           ra032
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024307