Absolute structure of the chiral pyrrolidine derivative (2S)-methyl (Z)-5-(2-tert-butoxy-1-cyano-2-oxoethylidene)pyrrolidine-2-carboxylate, a compound with low resonant scattering
Wang, Ai; Englert, Ulli; Acta Crystallographica Section C Structural Chemistry 75 (2019) –; doi:10.1107/S2053229619012324

data_2021790
_publ_section_title
;
 Absolute structure of the chiral pyrrolidine derivative (2S)-methyl
 (Z)-5-(2-tert-butoxy-1-cyano-2-oxoethylidene)pyrrolidine-2-carboxylate, a
 compound with low resonant scattering
;
_journal_coeditor_code           YF3192
_journal_issue                   11
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229619012324
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C13 H18 N2 O4'
_chemical_formula_moiety         'C13 H18 N2 O4'
_chemical_formula_sum            'C13 H18 N2 O4'
_chemical_formula_weight         266.29
_chemical_name_common            1mo
_chemical_name_systematic
;(2<i>S</i>)-Methyl
(<i>Z</i>)-5-(2-<i>tert</i>-butoxy-1-cyano-2-oxoethylidene)pyrrolidine-2-carboxylate
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.347(4)
_cell_length_b                   10.197(6)
_cell_length_c                   18.477(10)
_cell_measurement_reflns_used    1389
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.42
_cell_measurement_theta_min      2.28
_cell_volume                     1384.2(13)
_computing_cell_refinement
;
SMART (Bruker, 2001)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_publication_material
;
SHELXL2017 (Sheldrick, 2015) and
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 goniometer with APEX CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10626
_diffrn_reflns_theta_full        24.479
_diffrn_reflns_theta_max         24.479
_diffrn_reflns_theta_min         2.205
_diffrn_source                   'Incoatec microsource'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.4725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.182
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 710 quotients [(I+)-(I)-]/[(I+)+(I)-]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0228P)^2^+0.6063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                2051
_reflns_number_total             2290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yf3192sup1.cif
_cod_data_source_block           1mo
_cod_original_cell_volume        1384.1(13)
_cod_database_code               2021790
_cod_database_fobs_code          2021790
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.974
_shelx_hkl_checksum              45367
_shelx_res_checksum              50600