A temporary-bridge strategy for enantioselective organocatalyzed synthesis of aza-seven-membered rings
Sebastien Goudedranche; David Pierrot; Thierry Constantieux; Damien Bonne; Jean Rodriguez; Chem.Commun. 50 (2014) 15605–; doi:10.1039/C4cc07731H

data_7116079
_publ_section_title
;
 A temporary-bridge strategy for enantioselective organocatalyzed
 synthesis of aza-seven-membered rings
;
_journal_name_full               Chem.Commun.
_journal_page_first              15605
_journal_paper_doi               10.1039/C4cc07731H
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 Cl N2 O5'
_chemical_formula_sum            'C21 H21 Cl N2 O5'
_chemical_formula_weight         416.84
_chemical_melting_point          471
_chemical_name_systematic
(1R,2S,3R,5S)-6-(4-chlorophenyl)-1-hydroxy-2-isopropyl-3-(4-nitrophenyl)-8-oxa-6-azabicyclo[3.2.1]octan-7-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date
;
'Tue Apr 15 17:14:35 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   7.85187(17)
_cell_length_b                   19.3756(4)
_cell_length_c                   26.7779(6)
_cell_measurement_reflns_used    6029
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6850
_cell_measurement_theta_min      4.8330
_cell_volume                     4073.85(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega  -70.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5364  125.0000 -150.0000 68

  2 omega  -70.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5364   77.0000   30.0000 89

  3 omega   37.00   91.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -30.0000   90.0000 54

  4 omega   49.00   98.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -45.0000    0.0000 49

  5 omega   38.00  136.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -61.0000 -180.0000 98

  6 omega   36.00   82.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -45.0000  -90.0000 46

  7 omega   35.00  136.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -77.0000   90.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1536279000
_diffrn_orient_matrix_UB_12      -0.0485903000
_diffrn_orient_matrix_UB_13      -0.0071723000
_diffrn_orient_matrix_UB_21      -0.1020309000
_diffrn_orient_matrix_UB_22      0.0595979000
_diffrn_orient_matrix_UB_23      -0.0234472000
_diffrn_orient_matrix_UB_31      0.0670114000
_diffrn_orient_matrix_UB_32      -0.0201993000
_diffrn_orient_matrix_UB_33      -0.0520440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12523
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.645
_diffrn_reflns_theta_min         4.013
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.965
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1744
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          .26
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .06
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         7842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.4594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                7073
_reflns_number_total             7842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07731h2.cif
_cod_data_source_block           sg783
_cod_depositor_comments
;

2017-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4073.84(15)
_cod_original_formula_moiety     '2(C21 H21 Cl N2 O5)'
_cod_original_formula_sum        'C42 H42 Cl2 N4 O10'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     833.69
_cod_database_code               7116079
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 98.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C31(H31), C33(H33), C12(H12), C9(H9), C30(H30), C13(H13), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C42(H42), C20(H20), C21(H21), C41(H41), C38(H38), C17(H17), C39(H39), C2(H2A),
  C27(H27), C24(H24), C3(H3), C6(H6), C18(H18), C23(H23), C5(H5), C26(H26)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C36(H36A,H36B,
 H36C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7), O2(H2)
;
_shelx_res_checksum              79513