Densely substituted unnatural l- and d-prolines as catalysts for highly enantioselective stereodivergent (3 + 2) cycloadditions and aldol reactions
Conde, Egoitz; Bello, Davide; de Cózar, Abel; Sánchez, Mirian; Vázquez, Miguel A.; Cossío, Fernando P.; Chemical Science 3 (2012) 1486–; doi:10.1039/c2sc20199b

data_1515227
_publ_section_title
;
 Densely substituted unnatural l- and d-prolines as catalysts for highly
 enantioselective stereodivergent (3 + 2) cycloadditions and aldol
 reactions
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              1486
_journal_paper_doi               10.1039/c2sc20199b
_journal_volume                  3
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C34 H31 Fe1 N2 O4 P1'
_chemical_formula_sum            'C34 H31 Fe N2 O4 P'
_chemical_formula_weight         618.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-03-03T11:26:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.031(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0453(3)
_cell_length_b                   24.2072(8)
_cell_length_c                   9.1599(4)
_cell_measurement_reflns_used    20623
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.35
_cell_measurement_wavelength     0.71073
_cell_volume                     1476.81(11)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_details
;
Wavelength [\%A] : 0.71073
Tube power [kW] : 2.00
Tube voltage [kV] : 50
Tube current [mA] : 40
Collimator size [mm] : 0.5
Temperature [K] : 100.00
Detector distance [mm] : 120.0
Pixelsize [mm] : 0.150
Scanradius [mm] : 4.0 - 170.0
Detector 2Theta : 0.0
Filter usage : when needed
2theta range : 1.91 - 54.78
d(hkl) range [\%A] : 21.331 - 0.772

Reference Run
Phi : 222.0
Omega range : 0.0 - 5.0
Omega increment : 5.0
Exposure time [min] : 1.5
Frames : 1
Interval [h] : 1.00

Run #1
Phi : 222.0
Omega range : 0.0 - 156.0
Omega increment : 1.0
Exposure time [min] : 1.5
Frames : 156

Run #2
Phi : 90.0
Omega range : 148.0 - 180.0
Omega increment : 1.0
Exposure time [min] : 1.5
Frames : 32

Run #3
Phi : 222.0
Omega range : 156.0 - 180.0
Omega increment : 1.0
Exposure time [min] : 1.5
Frames : 24

Run #4
Phi : 90.0
Omega range : 0.0 - 148.0
Omega increment : 1.0
Exposure time [min] : 1.5
Frames : 148

Measured runs : 3 (out of 4)
Measured frames : 266 (out of 360)
Remeasured frames with filter : 0
Measured reference runs : 15
Statistics over all measured frames
Mean minimum pixel intensity : 5.4
Mean average pixel intensity : 11.7
Mean maximum pixel intensity : 16292.0
Total number of overflow pixels : 0

;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15941
_diffrn_reflns_theta_full        26.71
_diffrn_reflns_theta_max         26.71
_diffrn_reflns_theta_min         2.35
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  0.9356
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6137
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0360P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.057
_refine_ls_wR_factor_ref         0.0576
_reflns_number_gt                5762
_reflns_number_total             6137
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c2sc20199b.txt
_cod_data_source_block           cf57trit
_cod_original_cell_volume        1476.81(10)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1515227