A Model System for the Synthesis of Complanadine Alkaloids by "Diverted Kondrat'eva" Oxazole-Olefin Cycloaddition
Mario Uosis-Martin; G. Dan Pantoş; Mary F. Mahon; Simon E. Lewis; Journal of Organic Chemistry 78 (2013) 6253–6263; doi:10.1021/jo401014n

data_4028380
_publ_section_title
;
 A Model System for the Synthesis of Complanadine Alkaloids by "Diverted
 Kondrat'eva" Oxazole-Olefin Cycloaddition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6253
_journal_page_last               6263
_journal_paper_doi               10.1021/jo401014n
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C16.375 H23.375 Cl1.125 N O2'
_chemical_formula_weight         306.11
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.729(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8975(16)
_cell_length_b                   7.3862(4)
_cell_length_c                   30.776(3)
_cell_measurement_reflns_used    3934
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      62.7503
_cell_measurement_theta_min      2.8956
_cell_volume                     3355.7(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3795
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) x-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1109
_diffrn_reflns_av_sigmaI/netI    0.1074
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11535
_diffrn_reflns_theta_full        58.93
_diffrn_reflns_theta_max         58.93
_diffrn_reflns_theta_min         4.94
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       tabloid
_exptl_crystal_F_000             1310
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         4690
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.1043
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2796
_refine_ls_wR_factor_ref         0.3348
_reflns_number_gt                3004
_reflns_number_total             4690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401014n_si_002.cif
_cod_data_source_block           p10sel2
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32.75 H46.75 Cl2.25 N2 O4'
_cod_original_formula_weight         612.23
_cod_original_formula_units_Z            4
_cod_database_code               4028380