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#$Date: 2023-03-24 12:32:31 +0200 (Fri, 24 Mar 2023) $
#$Revision: 282050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106988.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_8106988
loop_
_publ_author_name
'Makhathini, Sifiso. S.'
'Samipillai, Marivel'
'Kruger, Hendrik G.'
'Govender, Thavendran'
'Naicker, Tricia'
_publ_section_title
;
 Crystal structure of 2-ethyl-1-tert-butyl
 3-oxo-2-[phenyl(tert-butoxycarbonylamino)methyl]-1,2-pyrrolidinedicarboxylate,
 C24H34N2O7
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              725
_journal_page_last               727
_journal_paper_doi               10.1515/ncrs-2015-0249
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C24 H34 N2 O7'
_chemical_formula_sum            'C24 H34 N2 O7'
_chemical_formula_weight         462.53
_chemical_name_systematic
;   
2-ethyl-1-tert-butyl 3-oxo-2-[phenyl(tert-butoxycarbonylamino)methyl]-1,2-pyrrolidinedicarboxylate
;
_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   mixed
_cell_angle_alpha                95.143(4)
_cell_angle_beta                 109.970(3)
_cell_angle_gamma                112.229(4)
_cell_formula_units_Z            2
_cell_length_a                   9.9562(8)
_cell_length_b                   10.7465(9)
_cell_length_c                   13.7925(11)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.42
_cell_volume                     1242.62(19)
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'Mercury 3.5.1 (2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22730
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.552
_diffrn_reflns_theta_min         1.623
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0460
_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)+(0.0602P)²+0.4413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5104
_reflns_number_total             6107
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0249_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1242.62(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106988
_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   0.972
_shelx_estimated_absorpt_t_max   0.984
_exptl_absorpt_special_details
;
?
;
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.02112(13) 0.87529(11) 0.13056(8) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.83768(12) 0.51481(10) 0.02935(8) 0.0331(2) Uani 1 1 d . . . . .
C2 C 1.10216(17) 0.86582(15) 0.06067(11) 0.0294(3) Uani 1 1 d . . . . .
H2A H 1.2118 0.8794 0.1026 0.035 Uiso 1 1 calc R U . . .
H2B H 1.1062 0.9359 0.0184 0.035 Uiso 1 1 calc R U . . .
C3 C 1.00040(19) 0.71966(15) -0.01089(11) 0.0330(3) Uani 1 1 d . . . . .
H3A H 0.9264 0.7204 -0.0801 0.040 Uiso 1 1 calc R U . . .
H3B H 1.0678 0.6780 -0.0242 0.040 Uiso 1 1 calc R U . . .
C4 C 0.91027(15) 0.63931(14) 0.04811(10) 0.0262(3) Uani 1 1 d . . . . .
C5 C 0.92225(14) 0.74169(12) 0.14132(9) 0.0218(2) Uani 1 1 d . . . . .
C6 C 1.05310(15) 1.00231(13) 0.18504(10) 0.0237(2) Uani 1 1 d . . . . .
O7 O 1.14645(12) 1.11067(10) 0.17901(8) 0.0322(2) Uani 1 1 d . . . . .
O8 O 0.96537(11) 0.98803(9) 0.24228(7) 0.0266(2) Uani 1 1 d . . . . .
C9 C 0.99721(16) 1.10813(14) 0.32284(11) 0.0281(3) Uani 1 1 d . . . . .
C10 C 1.16536(18) 1.16203(17) 0.40714(12) 0.0397(4) Uani 1 1 d . . . . .
H10A H 1.1786 1.0864 0.4377 0.060 Uiso 1 1 calc R U . . .
H10B H 1.1848 1.2372 0.4635 0.060 Uiso 1 1 calc R U . . .
H10C H 1.2412 1.1973 0.3746 0.060 Uiso 1 1 calc R U . . .
C11 C 0.9667(2) 1.21872(18) 0.27030(15) 0.0463(4) Uani 1 1 d . . . . .
H11B H 1.0539 1.2685 0.2500 0.069 Uiso 1 1 calc R U . . .
H11A H 0.9599 1.2844 0.3204 0.069 Uiso 1 1 calc R U . . .
H11C H 0.8665 1.1747 0.2066 0.069 Uiso 1 1 calc R U . . .
C12 C 0.87654(18) 1.04292(16) 0.36890(13) 0.0360(3) Uani 1 1 d . . . . .
H12A H 0.7690 1.0102 0.3136 0.054 Uiso 1 1 calc R U . . .
H12B H 0.8930 1.1121 0.4284 0.054 Uiso 1 1 calc R U . . .
H12C H 0.8897 0.9643 0.3944 0.054 Uiso 1 1 calc R U . . .
C13 C 0.75149(15) 0.72188(14) 0.11854(10) 0.0269(3) Uani 1 1 d . . . . .
O14 O 0.68589(12) 0.69308(12) 0.17685(9) 0.0385(3) Uani 1 1 d . . . . .
O15 O 0.68621(12) 0.73465(13) 0.01981(9) 0.0410(3) Uani 1 1 d . . . . .
C16 C 0.5183(2) 0.7043(2) -0.01980(15) 0.0527(5) Uani 1 1 d . . . . .
H16A H 0.4640 0.6326 0.0117 0.063 Uiso 1 1 calc R U . . .
H16B H 0.4678 0.6675 -0.0982 0.063 Uiso 1 1 calc R U . . .
C17 C 0.5002(3) 0.8321(3) 0.0084(3) 0.0861(9) Uani 1 1 d . . . . .
H17A H 0.5473 0.8668 0.0861 0.129 Uiso 1 1 calc R U . . .
H17B H 0.3872 0.8107 -0.0197 0.129 Uiso 1 1 calc R U . . .
H17C H 0.5544 0.9032 -0.0226 0.129 Uiso 1 1 calc R U . . .
C18 C 1.00019(14) 0.71243(12) 0.25073(9) 0.0216(2) Uani 1 1 d . . . . .
H18 H 1.0062 0.7813 0.3078 0.026 Uiso 1 1 calc R U . . .
C19 C 1.16920(15) 0.73394(13) 0.27269(9) 0.0229(2) Uani 1 1 d . . . . .
C20 C 1.19829(17) 0.63220(15) 0.22525(11) 0.0332(3) Uani 1 1 d . . . . .
H20 H 1.1115 0.5478 0.1791 0.040 Uiso 1 1 calc R U . . .
C21 C 1.35244(19) 0.65274(18) 0.24461(13) 0.0395(4) Uani 1 1 d . . . . .
H21 H 1.3701 0.5839 0.2098 0.047 Uiso 1 1 calc R U . . .
C22 C 1.47976(18) 0.77249(17) 0.31408(14) 0.0395(3) Uani 1 1 d . . . . .
H22 H 1.5852 0.7854 0.3287 0.047 Uiso 1 1 calc R U . . .
C23 C 1.45293(17) 0.87367(16) 0.36239(14) 0.0390(3) Uani 1 1 d . . . . .
H23 H 1.5404 0.9565 0.4104 0.047 Uiso 1 1 calc R U . . .
C24 C 1.29830(16) 0.85508(14) 0.34120(11) 0.0305(3) Uani 1 1 d . . . . .
H24 H 1.2813 0.9260 0.3740 0.037 Uiso 1 1 calc R U . . .
N25 N 0.90344(13) 0.57511(11) 0.25539(9) 0.0261(2) Uani 1 1 d . . . . .
H25 H 0.861(2) 0.5054(19) 0.2004(14) 0.034(4) Uiso 1 1 d . . . . .
C26 C 0.84183(15) 0.55846(13) 0.32979(10) 0.0254(3) Uani 1 1 d . . . . .
O27 O 0.87863(12) 0.65023(10) 0.40521(8) 0.0341(2) Uani 1 1 d . . . . .
O28 O 0.73836(12) 0.42433(10) 0.30790(8) 0.0322(2) Uani 1 1 d . . . . .
C29 C 0.65244(17) 0.37687(15) 0.37576(12) 0.0328(3) Uani 1 1 d . . . . .
C30 C 0.5564(2) 0.22215(16) 0.32452(17) 0.0476(4) Uani 1 1 d . . . . .
H30A H 0.4860 0.2072 0.2503 0.071 Uiso 1 1 calc R U . . .
H30B H 0.4927 0.1796 0.3636 0.071 Uiso 1 1 calc R U . . .
H30C H 0.6285 0.1797 0.3266 0.071 Uiso 1 1 calc R U . . .
C31 C 0.7677(3) 0.4028(2) 0.48876(16) 0.0592(5) Uani 1 1 d . . . . .
H31A H 0.8437 0.3659 0.4882 0.089 Uiso 1 1 calc R U . . .
H31B H 0.7092 0.3565 0.5296 0.089 Uiso 1 1 calc R U . . .
H31C H 0.8250 0.5029 0.5218 0.089 Uiso 1 1 calc R U . . .
C32 C 0.5429(2) 0.44562(19) 0.3676(2) 0.0537(5) Uani 1 1 d . . . . .
H32A H 0.6061 0.5463 0.3956 0.080 Uiso 1 1 calc R U . . .
H32B H 0.4806 0.4102 0.4092 0.080 Uiso 1 1 calc R U . . .
H32C H 0.4710 0.4249 0.2928 0.080 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 N1 C5 126.00(10) . .
C6 N1 C2 119.56(11) . .
C5 N1 C2 114.19(10) . .
N1 C2 C3 103.68(11) . .
N1 C2 H2A 111.0 . .
C3 C2 H2A 111.0 . .
N1 C2 H2B 111.0 . .
C3 C2 H2B 111.0 . .
H2A C2 H2B 109.0 . .
C4 C3 C2 105.68(10) . .
C4 C3 H3A 110.6 . .
C2 C3 H3A 110.6 . .
C4 C3 H3B 110.6 . .
C2 C3 H3B 110.6 . .
H3A C3 H3B 108.7 . .
O2 C4 C3 127.47(12) . .
O2 C4 C5 122.97(12) . .
C3 C4 C5 109.57(11) . .
N1 C5 C13 112.84(10) . .
N1 C5 C4 101.58(10) . .
C13 C5 C4 106.72(9) . .
N1 C5 C18 112.78(10) . .
C13 C5 C18 111.54(10) . .
C4 C5 C18 110.77(10) . .
O7 C6 O8 126.75(12) . .
O7 C6 N1 123.15(12) . .
O8 C6 N1 110.08(11) . .
C6 O8 C9 120.78(10) . .
O8 C9 C12 102.19(11) . .
O8 C9 C10 108.94(11) . .
C12 C9 C10 110.78(12) . .
O8 C9 C11 110.76(11) . .
C12 C9 C11 110.65(13) . .
C10 C9 C11 112.98(14) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11B 109.5 . .
C9 C11 H11A 109.5 . .
H11B C11 H11A 109.5 . .
C9 C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O14 C13 O15 125.58(12) . .
O14 C13 C5 125.78(12) . .
O15 C13 C5 108.54(11) . .
C13 O15 C16 116.13(13) . .
O15 C16 C17 110.34(17) . .
O15 C16 H16A 109.6 . .
C17 C16 H16A 109.6 . .
O15 C16 H16B 109.6 . .
C17 C16 H16B 109.6 . .
H16A C16 H16B 108.1 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N25 C18 C19 111.76(10) . .
N25 C18 C5 111.04(10) . .
C19 C18 C5 110.95(10) . .
N25 C18 H18 107.6 . .
C19 C18 H18 107.6 . .
C5 C18 H18 107.6 . .
C24 C19 C20 118.29(12) . .
C24 C19 C18 120.67(11) . .
C20 C19 C18 121.03(11) . .
C21 C20 C19 120.88(13) . .
C21 C20 H20 119.6 . .
C19 C20 H20 119.6 . .
C22 C21 C20 120.30(14) . .
C22 C21 H21 119.9 . .
C20 C21 H21 119.9 . .
C21 C22 C23 119.49(14) . .
C21 C22 H22 120.3 . .
C23 C22 H22 120.3 . .
C22 C23 C24 120.44(14) . .
C22 C23 H23 119.8 . .
C24 C23 H23 119.8 . .
C19 C24 C23 120.57(13) . .
C19 C24 H24 119.7 . .
C23 C24 H24 119.7 . .
C26 N25 C18 120.65(11) . .
C26 N25 H25 117.2(12) . .
C18 N25 H25 119.6(12) . .
O27 C26 O28 126.14(13) . .
O27 C26 N25 124.64(12) . .
O28 C26 N25 109.20(11) . .
C26 O28 C29 120.81(11) . .
O28 C29 C31 110.59(13) . .
O28 C29 C32 109.08(13) . .
C31 C29 C32 113.25(17) . .
O28 C29 C30 102.61(12) . .
C31 C29 C30 110.53(14) . .
C32 C29 C30 110.25(13) . .
C29 C30 H30A 109.5 . .
C29 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C29 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C29 C31 H31A 109.5 . .
C29 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C29 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C29 C32 H32A 109.5 . .
C29 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C29 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.3612(16) .
N1 C5 1.4564(16) .
N1 C2 1.4718(16) .
O2 C4 1.2075(17) .
C2 C3 1.517(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.500(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.5556(16) .
C5 C13 1.5439(17) .
C5 C18 1.5647(17) .
C6 O7 1.2158(16) .
C6 O8 1.3421(15) .
O8 C9 1.4811(15) .
C9 C12 1.517(2) .
C9 C10 1.519(2) .
C9 C11 1.519(2) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11B 0.9800 .
C11 H11A 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 O14 1.1916(17) .
C13 O15 1.3386(17) .
O15 C16 1.4603(19) .
C16 C17 1.486(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 N25 1.4469(16) .
C18 C19 1.5237(17) .
C18 H18 1.0000 .
C19 C24 1.3869(18) .
C19 C20 1.3958(18) .
C20 C21 1.389(2) .
C20 H20 0.9500 .
C21 C22 1.377(2) .
C21 H21 0.9500 .
C22 C23 1.382(2) .
C22 H22 0.9500 .
C23 C24 1.395(2) .
C23 H23 0.9500 .
C24 H24 0.9500 .
N25 C26 1.3569(17) .
N25 H25 0.868(18) .
C26 O27 1.2130(16) .
C26 O28 1.3477(16) .
O28 C29 1.4732(17) .
C29 C31 1.511(2) .
C29 C32 1.513(2) .
C29 C30 1.518(2) .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{516c985e-c633-4486-b4b2-c42c79727732} ? ? ?
{2a92af92-4d4d-4f9a-bc3a-3a077b2cb682} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{516c985e-c633-4486-b4b2-c42c79727732} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EE
