#------------------------------------------------------------------------------
#$Date: 2020-05-30 08:05:39 +0300 (Sat, 30 May 2020) $
#$Revision: 252483 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243415.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243415
loop_
_publ_author_name
'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.'
_publ_section_title
;
 1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: crystal
 structure, Hirshfeld surface analysis and computational chemistry
;
_journal_coeditor_code           HB7916
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              967
_journal_page_last               972
_journal_paper_doi               10.1107/S205698902000701X
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C13 H19 N O8'
_chemical_formula_moiety         'C13 H19 N O8'
_chemical_formula_sum            'C13 H19 N O8'
_chemical_formula_weight         317.29
_chemical_name_systematic
;
1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                100.607(11)
_cell_angle_beta                 99.011(10)
_cell_angle_gamma                105.054(7)
_cell_formula_units_Z            2
_cell_length_a                   6.8291(5)
_cell_length_b                   7.8670(11)
_cell_length_c                   15.814(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      18.15
_cell_measurement_theta_min      10.77
_cell_volume                     787.5(2)
_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), MarvinSketch
(ChemAxon, 2010) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
PublCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2014 (Burla et al.,  2015)
;
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.988
_diffrn_reflns_theta_min         2.684
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       irregular
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0419
_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/[σ²(Fo²)+(0.0579P)²+0.0763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                2571
_reflns_number_total             4573
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7916sup1.cif
_cod_data_source_block           I
_cod_database_code               2243415
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.28490(19) 0.08131(19) 0.64555(9) 0.0568(3) Uani d 1 . .
O O2 0.12213(18) 0.24723(18) 0.57354(8) 0.0513(3) Uani d 1 . .
O O3 0.35221(19) 0.33818(18) 0.83767(9) 0.0586(3) Uani d 1 . .
O O4 0.20434(18) 0.14935(17) 0.91551(8) 0.0504(3) Uani d 1 . .
O O5 -0.5275(2) -0.0729(2) 0.83254(9) 0.0662(4) Uani d 1 . .
O O6 -0.32790(16) -0.06328(15) 0.73314(7) 0.0424(3) Uani d 1 . .
O O7 -0.2014(3) 0.6135(2) 0.78612(11) 0.0753(4) Uani d 1 . .
O O8 -0.08692(17) 0.40628(15) 0.84074(7) 0.0426(3) Uani d 1 . .
N N1 0.0250(2) 0.1764(2) 0.69258(9) 0.0433(3) Uani d 1 . .
C C1 0.0322(2) 0.0990(2) 0.76913(10) 0.0372(3) Uani d 1 . .
H H1 0.041065 -0.024702 0.752792 0.045 Uiso calc 1 . .
C C2 -0.1782(2) 0.0948(2) 0.79177(10) 0.0357(3) Uani d 1 . .
H H2 -0.177363 0.096071 0.853908 0.043 Uiso calc 1 . .
C C3 -0.2178(2) 0.2626(2) 0.76694(10) 0.0388(3) Uani d 1 . .
H H3 -0.364464 0.257939 0.758613 0.047 Uiso calc 1 . .
C C4 -0.1353(2) 0.2683(2) 0.68313(11) 0.0430(4) Uani d 1 . .
H H4A -0.244190 0.204920 0.631224 0.052 Uiso calc 1 . .
H H4B -0.076679 0.392201 0.679209 0.052 Uiso calc 1 . .
C C5 0.1565(2) 0.1615(2) 0.63798(10) 0.0424(4) Uani d 1 . .
C C6 0.2518(3) 0.2410(3) 0.50973(13) 0.0631(5) Uani d 1 . .
H H6A 0.234590 0.116529 0.480776 0.076 Uiso calc 1 . .
H H6B 0.396809 0.298206 0.538377 0.076 Uiso calc 1 . .
C C7 0.1853(4) 0.3399(4) 0.44469(15) 0.0818(7) Uani d 1 . .
H H7A 0.041201 0.282919 0.417435 0.123 Uiso calc 1 . .
H H7B 0.266749 0.337723 0.400460 0.123 Uiso calc 1 . .
H H7C 0.204764 0.463198 0.474089 0.123 Uiso calc 1 . .
C C8 0.2155(2) 0.2132(2) 0.84352(11) 0.0404(3) Uani d 1 . .
C C9 0.3834(3) 0.2283(4) 0.98760(14) 0.0766(7) Uani d 1 . .
H H9A 0.506912 0.224946 0.966399 0.115 Uiso calc 1 . .
H H9B 0.370682 0.160845 1.032257 0.115 Uiso calc 1 . .
H H9C 0.391528 0.351722 1.012025 0.115 Uiso calc 1 . .
C C10 -0.4972(2) -0.1374(2) 0.76304(12) 0.0461(4) Uani d 1 . .
C C11 -0.6347(3) -0.3050(3) 0.69971(16) 0.0697(6) Uani d 1 . .
H H11A -0.581462 -0.404559 0.706145 0.104 Uiso calc 1 . .
H H11B -0.639848 -0.289168 0.640732 0.104 Uiso calc 1 . .
H H11C -0.771979 -0.329842 0.711270 0.104 Uiso calc 1 . .
C C12 -0.0926(3) 0.5768(2) 0.84243(13) 0.0500(4) Uani d 1 . .
C C13 0.0585(4) 0.7066(3) 0.92107(15) 0.0696(6) Uani d 1 . .
H H13A 0.194942 0.735689 0.908739 0.104 Uiso calc 1 . .
H H13B 0.058933 0.652183 0.970653 0.104 Uiso calc 1 . .
H H13C 0.018502 0.815216 0.934292 0.104 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O2 C6 . . 115.92(14) ?
C8 O4 C9 . . 115.73(15) ?
C10 O6 C2 . . 116.20(12) ?
C12 O8 C3 . . 118.19(13) ?
C5 N1 C1 . . 121.34(13) ?
C5 N1 C4 . . 125.77(13) ?
C1 N1 C4 . . 112.89(12) ?
N1 C1 C8 . . 111.47(13) ?
N1 C1 C2 . . 102.32(12) ?
C8 C1 C2 . . 113.23(13) ?
N1 C1 H1 . . 109.9 ?
C8 C1 H1 . . 109.9 ?
C2 C1 H1 . . 109.9 ?
O6 C2 C3 . . 108.78(12) ?
O6 C2 C1 . . 106.68(12) ?
C3 C2 C1 . . 103.23(12) ?
O6 C2 H2 . . 112.5 ?
C3 C2 H2 . . 112.5 ?
C1 C2 H2 . . 112.5 ?
O8 C3 C2 . . 102.26(11) ?
O8 C3 C4 . . 111.80(12) ?
C2 C3 C4 . . 103.54(13) ?
O8 C3 H3 . . 112.8 ?
C2 C3 H3 . . 112.8 ?
C4 C3 H3 . . 112.8 ?
N1 C4 C3 . . 103.35(12) ?
N1 C4 H4A . . 111.1 ?
C3 C4 H4A . . 111.1 ?
N1 C4 H4B . . 111.1 ?
C3 C4 H4B . . 111.1 ?
H4A C4 H4B . . 109.1 ?
O1 C5 O2 . . 125.04(15) ?
O1 C5 N1 . . 124.93(15) ?
O2 C5 N1 . . 110.02(14) ?
O2 C6 C7 . . 106.76(17) ?
O2 C6 H6A . . 110.4 ?
C7 C6 H6A . . 110.4 ?
O2 C6 H6B . . 110.4 ?
C7 C6 H6B . . 110.4 ?
H6A C6 H6B . . 108.6 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O3 C8 O4 . . 124.90(16) ?
O3 C8 C1 . . 125.34(15) ?
O4 C8 C1 . . 109.73(13) ?
O4 C9 H9A . . 109.5 ?
O4 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O4 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O5 C10 O6 . . 122.72(16) ?
O5 C10 C11 . . 125.62(16) ?
O6 C10 C11 . . 111.66(16) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O7 C12 O8 . . 122.72(18) ?
O7 C12 C13 . . 126.78(18) ?
O8 C12 C13 . . 110.46(16) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.2098(19) ?
O2 C5 . 1.345(2) ?
O2 C6 . 1.446(2) ?
O3 C8 . 1.1961(19) ?
O4 C8 . 1.3312(19) ?
O4 C9 . 1.445(2) ?
O5 C10 . 1.195(2) ?
O6 C10 . 1.3499(19) ?
O6 C2 . 1.4385(18) ?
O7 C12 . 1.195(2) ?
O8 C12 . 1.348(2) ?
O8 C3 . 1.4496(19) ?
N1 C5 . 1.351(2) ?
N1 C1 . 1.4518(19) ?
N1 C4 . 1.464(2) ?
C1 C8 . 1.524(2) ?
C1 C2 . 1.528(2) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.521(2) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.523(2) ?
C3 H3 . 0.9800 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C6 C7 . 1.484(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.483(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.496(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9B O5 2_557 0.96 2.53 3.403(3) 151
C3 H3 O1 1_455 0.98 2.62 3.419(2) 139
C3 H3 O3 1_455 0.98 2.61 3.453(2) 144
C11 H11A O7 1_545 0.96 2.66 3.329(3) 127
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C8 . . . . 76.02(19) ?
C4 N1 C1 C8 . . . . -103.88(15) ?
C5 N1 C1 C2 . . . . -162.67(14) ?
C4 N1 C1 C2 . . . . 17.43(18) ?
C10 O6 C2 C3 . . . . -96.72(15) ?
C10 O6 C2 C1 . . . . 152.54(13) ?
N1 C1 C2 O6 . . . . 80.73(14) ?
C8 C1 C2 O6 . . . . -159.17(12) ?
N1 C1 C2 C3 . . . . -33.83(15) ?
C8 C1 C2 C3 . . . . 86.27(14) ?
C12 O8 C3 C2 . . . . -176.59(13) ?
C12 O8 C3 C4 . . . . 73.23(17) ?
O6 C2 C3 O8 . . . . 168.91(11) ?
C1 C2 C3 O8 . . . . -78.04(13) ?
O6 C2 C3 C4 . . . . -74.78(14) ?
C1 C2 C3 C4 . . . . 38.26(15) ?
C5 N1 C4 C3 . . . . -173.74(15) ?
C1 N1 C4 C3 . . . . 6.15(18) ?
O8 C3 C4 N1 . . . . 82.01(15) ?
C2 C3 C4 N1 . . . . -27.36(15) ?
C6 O2 C5 O1 . . . . -0.3(3) ?
C6 O2 C5 N1 . . . . -179.62(15) ?
C1 N1 C5 O1 . . . . 2.0(3) ?
C4 N1 C5 O1 . . . . -178.13(17) ?
C1 N1 C5 O2 . . . . -178.67(14) ?
C4 N1 C5 O2 . . . . 1.2(2) ?
C5 O2 C6 C7 . . . . 178.98(17) ?
C9 O4 C8 O3 . . . . -6.4(3) ?
C9 O4 C8 C1 . . . . 171.57(15) ?
N1 C1 C8 O3 . . . . -8.7(2) ?
C2 C1 C8 O3 . . . . -123.40(18) ?
N1 C1 C8 O4 . . . . 173.33(13) ?
C2 C1 C8 O4 . . . . 58.60(17) ?
C2 O6 C10 O5 . . . . 3.0(2) ?
C2 O6 C10 C11 . . . . -176.72(15) ?
C3 O8 C12 O7 . . . . 0.4(2) ?
C3 O8 C12 C13 . . . . -177.58(14) ?

_cod_database_fobs_code 2243415
