#------------------------------------------------------------------------------
#$Date: 2023-02-14 12:21:10 +0200 (Tue, 14 Feb 2023) $
#$Revision: 280885 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106780.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106780
loop_
_publ_author_name
'Bhatt, Nilay'
'Samipillai, Marivale'
'Das, Sukant Kishore'
'Kruger, Hendrik Gert'
'Govender, Thavendran'
'Maguire, Glenn E.M.'
_publ_section_title
;
 Crystal structure of
 2-(ethoxycarbonyl)-2-(2-nitro-1-phenylethyl)-3-oxopyrrolidinium chloride,
 C15H19N2O5Cl
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              43
_journal_page_last               45
_journal_paper_doi               10.1515/ncrs-2014-9095
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C15 H19 Cl N2 O5'
_chemical_formula_weight         342.77
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2014-10-28 # Formatted by publCIF
;
_cell_angle_alpha                101.450(5)
_cell_angle_beta                 100.713(5)
_cell_angle_gamma                100.508(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2232(9)
_cell_length_b                   8.5833(10)
_cell_length_c                   12.5916(13)
_cell_measurement_reflns_used    29079
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.65
_cell_volume                     833.39(16)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT program (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'OLEX2 (Dolomanov, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29079
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9671
_exptl_absorpt_correction_T_min  0.9120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0380P)²+0.3007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0870
_reflns_number_gt                3343
_reflns_number_total             3956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2014-9095_suppl.cif
_cod_data_source_block           ns_1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106780
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.24337(4) 0.47941(4) 0.58480(2) 0.03075(10) Uani 1 1 d . . .
O1 O 0.38176(12) 0.50693(12) 0.16648(8) 0.0339(2) Uani 1 1 d . . .
O2 O 0.01854(12) 0.32383(13) 0.04996(8) 0.0361(2) Uani 1 1 d . . .
O3 O -0.13671(11) 0.42017(12) 0.16694(7) 0.0308(2) Uani 1 1 d . . .
O4 O 0.49417(18) 0.09410(15) 0.41908(10) 0.0542(3) Uani 1 1 d . . .
O5 O 0.42175(14) 0.04683(13) 0.24075(9) 0.0417(3) Uani 1 1 d . . .
N1 N 0.09851(14) 0.49689(13) 0.34737(9) 0.0230(2) Uani 1 1 d . . .
H1 H 0.153(2) 0.474(2) 0.4109(15) 0.038(4) Uiso 1 1 d . . .
H2 H -0.012(2) 0.4756(19) 0.3445(13) 0.033(4) Uiso 1 1 d . . .
N2 N 0.42723(14) 0.12602(13) 0.33382(10) 0.0300(2) Uani 1 1 d . . .
C1 C 0.15936(19) 0.67858(16) 0.36050(12) 0.0327(3) Uani 1 1 d . . .
H1A H 0.1811 0.7386 0.4393 0.039 Uiso 1 1 calc R . .
H1B H 0.0747 0.7215 0.3148 0.039 Uiso 1 1 calc R . .
C2 C 0.3230(2) 0.69317(18) 0.31962(14) 0.0403(3) Uani 1 1 d . . .
H2A H 0.3416 0.7883 0.2863 0.048 Uiso 1 1 calc R . .
H2B H 0.4218 0.7057 0.3817 0.048 Uiso 1 1 calc R . .
C3 C 0.29883(15) 0.53732(15) 0.23393(10) 0.0248(3) Uani 1 1 d . . .
C4 C 0.14552(15) 0.41036(14) 0.24573(9) 0.0210(2) Uani 1 1 d . . .
C5 C 0.00081(15) 0.37917(15) 0.14118(10) 0.0230(2) Uani 1 1 d . . .
C6 C -0.28649(17) 0.3896(2) 0.07469(12) 0.0368(3) Uani 1 1 d . . .
H6A H -0.2503 0.4221 0.0100 0.044 Uiso 1 1 calc R . .
H6B H -0.3653 0.4571 0.0978 0.044 Uiso 1 1 calc R . .
C7 C -0.3769(2) 0.2134(3) 0.04132(17) 0.0602(5) Uani 1 1 d . . .
H7A H -0.3025 0.1473 0.0119 0.090 Uiso 1 1 calc R . .
H7B H -0.4806 0.1981 -0.0162 0.090 Uiso 1 1 calc R . .
H7C H -0.4069 0.1794 0.1064 0.090 Uiso 1 1 calc R . .
C8 C 0.19639(15) 0.24659(14) 0.25108(10) 0.0219(2) Uani 1 1 d . . .
H8 H 0.2324 0.2095 0.1805 0.026 Uiso 1 1 calc R . .
C9 C 0.35225(16) 0.27277(15) 0.34572(11) 0.0263(3) Uani 1 1 d . . .
H9A H 0.4382 0.3693 0.3448 0.032 Uiso 1 1 calc R . .
H9B H 0.3192 0.2939 0.4180 0.032 Uiso 1 1 calc R . .
C10 C 0.04997(15) 0.11102(15) 0.25368(10) 0.0231(2) Uani 1 1 d . . .
C11 C -0.01581(18) 0.10917(16) 0.34835(11) 0.0313(3) Uani 1 1 d . . .
H11 H 0.0310 0.1945 0.4137 0.038 Uiso 1 1 calc R . .
C12 C -0.14953(19) -0.01723(18) 0.34713(13) 0.0372(3) Uani 1 1 d . . .
H12 H -0.1941 -0.0171 0.4115 0.045 Uiso 1 1 calc R . .
C13 C -0.21804(18) -0.14314(17) 0.25275(13) 0.0357(3) Uani 1 1 d . . .
H13 H -0.3098 -0.2287 0.2521 0.043 Uiso 1 1 calc R . .
C14 C -0.15207(18) -0.14371(17) 0.15930(12) 0.0340(3) Uani 1 1 d . . .
H14 H -0.1981 -0.2303 0.0945 0.041 Uiso 1 1 calc R . .
C15 C -0.01819(17) -0.01758(16) 0.16003(11) 0.0285(3) Uani 1 1 d . . .
H15 H 0.0271 -0.0194 0.0958 0.034 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 O3 C6 116.83(10) . .
H1 N1 H2 108.1(15) . .
C1 N1 H1 106.2(10) . .
C1 N1 H2 108.3(10) . .
C4 N1 H1 112.0(10) . .
C4 N1 H2 114.2(10) . .
C4 N1 C1 107.71(9) . .
O4 N2 O5 123.51(12) . .
O4 N2 C9 117.27(11) . .
O5 N2 C9 119.20(11) . .
N1 C1 H1A 111.0 . .
N1 C1 H1B 111.0 . .
N1 C1 C2 103.85(10) . .
H1A C1 H1B 109.0 . .
C2 C1 H1A 111.0 . .
C2 C1 H1B 111.0 . .
C1 C2 H2A 110.7 . .
C1 C2 H2B 110.7 . .
H2A C2 H2B 108.8 . .
C3 C2 C1 105.11(11) . .
C3 C2 H2A 110.7 . .
C3 C2 H2B 110.7 . .
O1 C3 C2 128.06(12) . .
O1 C3 C4 122.95(11) . .
C2 C3 C4 108.98(10) . .
N1 C4 C3 103.04(9) . .
N1 C4 C5 111.03(9) . .
N1 C4 C8 116.13(10) . .
C5 C4 C3 108.05(9) . .
C5 C4 C8 108.07(9) . .
C8 C4 C3 110.22(9) . .
O2 C5 O3 126.94(12) . .
O2 C5 C4 121.48(11) . .
O3 C5 C4 111.59(10) . .
O3 C6 H6A 109.4 . .
O3 C6 H6B 109.4 . .
O3 C6 C7 111.25(13) . .
H6A C6 H6B 108.0 . .
C7 C6 H6A 109.4 . .
C7 C6 H6B 109.4 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C4 C8 H8 106.3 . .
C9 C8 C4 110.61(10) . .
C9 C8 H8 106.3 . .
C10 C8 C4 113.78(10) . .
C10 C8 H8 106.3 . .
C10 C8 C9 113.04(10) . .
N2 C9 C8 110.56(10) . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
C11 C10 C8 122.18(11) . .
C15 C10 C8 119.17(11) . .
C15 C10 C11 118.62(12) . .
C10 C11 H11 119.9 . .
C12 C11 C10 120.28(12) . .
C12 C11 H11 119.9 . .
C11 C12 H12 119.8 . .
C13 C12 C11 120.50(13) . .
C13 C12 H12 119.8 . .
C12 C13 H13 120.2 . .
C14 C13 C12 119.64(13) . .
C14 C13 H13 120.2 . .
C13 C14 H14 119.9 . .
C13 C14 C15 120.13(13) . .
C15 C14 H14 119.9 . .
C10 C15 C14 120.81(12) . .
C10 C15 H15 119.6 . .
C14 C15 H15 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.2028(16) .
O2 C5 1.1988(15) .
O3 C5 1.3206(15) .
O3 C6 1.4712(15) .
O4 N2 1.2176(15) .
O5 N2 1.2208(15) .
N1 H1 0.916(18) .
N1 H2 0.886(17) .
N1 C1 1.5140(17) .
N1 C4 1.5001(15) .
N2 C9 1.4939(16) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.521(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C2 C3 1.4978(19) .
C3 C4 1.5594(16) .
C4 C5 1.5435(16) .
C4 C8 1.5483(17) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.496(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8 1.0000 .
C8 C9 1.5278(17) .
C8 C10 1.5244(16) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.3992(18) .
C10 C15 1.3910(17) .
C11 H11 0.9500 .
C11 C12 1.3923(19) .
C12 H12 0.9500 .
C12 C13 1.384(2) .
C13 H13 0.9500 .
C13 C14 1.384(2) .
C14 H14 0.9500 .
C14 C15 1.3935(18) .
C15 H15 0.9500 .
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
N(1) H(1) Cl(1) . 0.917(18) 2.166(18) 3.0494(12) 161.5(15)
N(1) H(2) O(3) . 0.886(17) 2.196(16) 2.5776(14) 105.4(12)
N(1) H(2) Cl(1) 2_566 0.886(17) 2.307(17) 3.1156(13) 151.7(14)
C(2) H(2A) O(5) 1_565 0.99 2.41 3.385(2) 169
C(6) H(6A) O(1) 2_565 0.99 2.52 3.3263(18) 138
C(6) H(6B) O(1) 1_455 0.99 2.47 3.3918(18) 155
C(8) H(8) O(5) . 1.00 2.39 2.7479(17) 100
C(9) H(9A) Cl(1) 2_666 0.99 2.60 3.4565(14) 145
C(9) H(9B) Cl(1) . 0.99 2.62 3.5315(14) 153
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C3 C4 N1 173.46(12) . . . .
O1 C3 C4 C5 -68.97(15) . . . .
O1 C3 C4 C8 48.92(16) . . . .
O4 N2 C9 C8 -147.42(12) . . . .
O5 N2 C9 C8 34.00(16) . . . .
N1 C1 C2 C3 29.90(15) . . . .
N1 C4 C5 O2 173.63(12) . . . .
N1 C4 C5 O3 -6.56(14) . . . .
N1 C4 C8 C9 -60.71(13) . . . .
N1 C4 C8 C10 67.80(13) . . . .
C1 N1 C4 C3 24.42(12) . . . .
C1 N1 C4 C5 -91.03(12) . . . .
C1 N1 C4 C8 145.01(11) . . . .
C1 C2 C3 O1 165.91(13) . . . .
C1 C2 C3 C4 -15.42(15) . . . .
C2 C3 C4 N1 -5.29(13) . . . .
C2 C3 C4 C5 112.28(12) . . . .
C2 C3 C4 C8 -129.83(12) . . . .
C3 C4 C5 O2 61.33(15) . . . .
C3 C4 C5 O3 -118.86(11) . . . .
C3 C4 C8 C9 55.94(12) . . . .
C3 C4 C8 C10 -175.55(10) . . . .
C4 N1 C1 C2 -34.53(14) . . . .
C4 C8 C9 N2 -165.86(10) . . . .
C4 C8 C10 C11 -73.39(15) . . . .
C4 C8 C10 C15 108.27(13) . . . .
C5 O3 C6 C7 78.35(16) . . . .
C5 C4 C8 C9 173.81(10) . . . .
C5 C4 C8 C10 -57.68(12) . . . .
C6 O3 C5 O2 2.3(2) . . . .
C6 O3 C5 C4 -177.48(11) . . . .
C8 C4 C5 O2 -57.93(15) . . . .
C8 C4 C5 O3 121.88(11) . . . .
C8 C10 C11 C12 -179.90(13) . . . .
C8 C10 C15 C14 179.99(12) . . . .
C9 C8 C10 C11 53.87(16) . . . .
C9 C8 C10 C15 -124.47(12) . . . .
C10 C8 C9 N2 65.23(13) . . . .
C10 C11 C12 C13 0.5(2) . . . .
C11 C10 C15 C14 1.6(2) . . . .
C11 C12 C13 C14 0.5(2) . . . .
C12 C13 C14 C15 -0.5(2) . . . .
C13 C14 C15 C10 -0.6(2) . . . .
C15 C10 C11 C12 -1.6(2) . . . .
