First Total Synthesis of ent-Asperparaline C and Assignment of the Absolute Configuration of Asperparaline C
Dokli, Irena; Pohl, Radek; Klepetářová, Blanka; Jahn, Ullrich; Chemical Communications  (2019) –; doi:10.1039/C9CC00945K

data_7123115
_publ_section_title
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 First Total Synthesis of ent-Asperparaline C and Assignment of the
 Absolute Configuration of Asperparaline C
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00945K
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 N2 O4'
_chemical_formula_sum            'C19 H24 N2 O4'
_chemical_formula_weight         344.41
_chemical_name_systematic
(6R,7R,8aR)-6-(Furan-3-ylmethyl)-10-(methoxymethyl)-7-(prop-1-en-2-yl)tetrahydro-1H-6,8a-(epiminomethano)indolizine-5,9(6H)-dione
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2018-10-26 deposited with the CCDC.    2019-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2195(2)
_cell_length_b                   11.0955(3)
_cell_length_c                   18.8126(5)
_cell_measurement_reflns_used    214
_cell_measurement_temperature    180
_cell_measurement_theta_max      57.6605
_cell_measurement_theta_min      12.0256
_cell_volume                     1715.70(8)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27100
_diffrn_reflns_theta_full        69.950
_diffrn_reflns_theta_max         69.950
_diffrn_reflns_theta_min         4.627
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.13
_refine_ls_abs_structure_details 'Flack (1983), 1370 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.09(13)
_refine_ls_extinction_coef       50(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0732
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.0045414
_refine_ls_shift/su_mean         0.0010400
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.124 0.914E-01 0.340E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0291
_refine_ls_wR_factor_gt          0.0271
_refine_ls_wR_factor_ref         0.0271
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3196
_reflns_number_total             3244
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.54
_oxford_diffrn_Wilson_scale      20.07
_oxford_refine_ls_r_factor_ref   0.0247
_oxford_refine_ls_scale          0.2213(3)
_oxford_reflns_number_all        3244
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT ENANTIO 
RIDE C   (   9,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 253,X'S) H   ( 252,X'S) H   ( 251,X'S) 
END                                                                             
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_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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_cod_data_source_file            c9cc00945k2.cif
_cod_data_source_block           1
_cod_database_code               7123115