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_2021791
_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 rm
_chemical_formula_moiety         'C13 H18 N2 O4'
_chemical_formula_sum            'C13 H18 N2 O4'
_chemical_formula_weight         266.29
_chemical_name_common            1cu
_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   difmap
_atom_sites_solution_primary     other
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3731(3)
_cell_length_b                   10.1909(4)
_cell_length_c                   18.4972(7)
_cell_measurement_reflns_used    6101
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.26
_cell_measurement_theta_min      7.41
_cell_volume                     1389.85(9)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 goniometer with APEX CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17945
_diffrn_reflns_theta_full        67.026
_diffrn_reflns_theta_max         67.026
_diffrn_reflns_theta_min         4.781
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_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         0.166
_refine_diff_density_min         -0.153
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 879 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_coef       0.0076(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2017 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0379P)^2^+0.0440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0771
_reflns_number_gt                2266
_reflns_number_total             2408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yf3192sup1.cif
_cod_data_source_block           1cu
_cod_database_code               2021791
_cod_database_fobs_code          2021791
_shelx_estimated_absorpt_t_min   0.770
_shelx_estimated_absorpt_t_max   0.809
_shelx_hkl_checksum              99683
_shelx_res_checksum              85707