Stereoselective synthesis of complex polycyclic aziridines: use of the Bronsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency
Priya A. Mathew; Amie L. Williams; John C. Huffman; Jeffrey Johnston; Chem.Commun. 47 (2011) 3975–; doi:10.1039/c0cc05734g

data_7106164
_publ_section_title
;
 Stereoselective synthesis of complex polycyclic aziridines: use of the
 Bronsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally
 protected mitomycin C intermediate with maximal convergency
;
_journal_name_full               Chem.Commun.
_journal_page_first              3975
_journal_paper_doi               10.1039/c0cc05734g
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C46 H37 Cl N2 O4'
_chemical_formula_sum            'C46 H37 Cl N2 O4'
_chemical_formula_weight         717.23
_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                 92.131(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.104(3)
_cell_length_b                   18.720(4)
_cell_length_c                   16.171(4)
_cell_measurement_reflns_used    868
_cell_measurement_temperature    121(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      2.33
_cell_volume                     3661.6(15)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999), XTEL (local program)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      121(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
' 0.30 degree frames measured for 60.17 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_measurement_method       '\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  0.2370
_diffrn_reflns_av_sigmaI/netI    0.3539
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26161
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.617
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         8434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.617
_refine_ls_R_factor_all          0.2098
_refine_ls_R_factor_gt           0.0489
_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
[1.00000+0.00000exp(0.00(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0000P)^2^+0.0000sin\q/\l]
where P = 0.20000Fo^2^ + 0.80000Fc^2^
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                2487
_reflns_number_total             8434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc05734g.txt
_cod_data_source_block           05103
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7106164