4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry
Dallasta Pedroso, Sofia; Caracelli, Ignez; Zukerman-Schpector, Julio; Soto-Monsalve, Monica; De Almeida Santos, Regina H.; Correia, Carlos Roque D.; Llanes Garcia, Ariel L.; Kwong, Huey Chong; Tiekink, Edward R. T.; Acta Crystallographica Section E 76 (2020) 1080–1086; doi:10.1107/S2056989020007914

data_2243439
_publ_section_title
;
 4-Nitrobenzyl
 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal
 structure, Hirshfeld surface analysis and computational chemistry
;
_journal_coeditor_code           HB7923
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1080
_journal_page_last               1086
_journal_paper_doi               10.1107/S2056989020007914
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C23 H24 N2 O9'
_chemical_formula_moiety         'C23 H24 N2 O9'
_chemical_formula_sum            'C23 H24 N2 O9'
_chemical_formula_weight         472.44
_chemical_name_systematic
;
4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 110.0130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.6396(5)
_cell_length_b                   8.2906(2)
_cell_length_c                   24.7683(5)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.62
_cell_volume                     4561.13(18)
_computing_cell_refinement
;
CAD-4 EXPRESS (Enraf--Nonius, 1989)
;
_computing_data_collection
;
CAD-4 EXPRESS (Enraf--Nonius, 1989)
;
_computing_data_reduction
;
XCAD4 (Harms & Wocadlo, 1995)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), <i>MarvinSketch</i>
(ChemAxon, 2010) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2014 (Burla <i>et al.</i>,  2015)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius TurboCAD-4'
_diffrn_measurement_method       'non-profiled \w/2\q scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22357
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.390
_diffrn_reflns_theta_min         1.750
_diffrn_source                   'Enraf--Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+5.1476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                3646
_reflns_number_total             4172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7923sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243439
_cod_database_fobs_code          2243439
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              97179
_shelx_res_checksum              84122