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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/61/7106100.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_7106100
loop_
_publ_author_name
'Srinivas Tekkam'
'M. A. Alam'
'Subash C. Jonnalagadda'
'Venkatram R. Mereddy'
_publ_section_title
;
 Novel methodologies for the synthesis of functionalized pyroglutamates
;
_journal_name_full               Chem.Commun.
_journal_page_first              3219
_journal_paper_doi               10.1039/c0cc05609j
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C23 H25 N O3'
_chemical_formula_sum            'C23 H25 N O3'
_chemical_formula_weight         363.44
_chemical_name_common            10102a
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.817(2)
_cell_angle_beta                 107.229(2)
_cell_angle_gamma                109.137(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4398(11)
_cell_length_b                   10.1347(13)
_cell_length_c                   13.0478(17)
_cell_measurement_reflns_used    4086
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      2.17
_cell_volume                     986.6(2)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10405
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3997
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0430P)²+0.2709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2776
_reflns_number_total             3997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC05609J.TXT
_cod_data_source_block           10102a
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106100
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.57037(19) 0.14666(16) 0.43381(12) 0.0281(4) Uani 1 1 d D . .
H1A H 0.4723(14) 0.0974(16) 0.4454(14) 0.034 Uiso 1 1 d D . .
O1 O 0.74086(16) 0.03041(14) 0.52893(11) 0.0364(3) Uani 1 1 d . . .
O2 O 0.40132(16) 0.33731(13) 0.42818(10) 0.0342(3) Uani 1 1 d . . .
O3 O 0.50183(16) 0.42758(13) 0.29813(10) 0.0330(3) Uani 1 1 d . . .
C1 C 0.5724(2) 0.23440(18) 0.35108(14) 0.0246(4) Uani 1 1 d . . .
C2 C 0.7193(2) 0.11728(19) 0.47086(14) 0.0286(4) Uani 1 1 d . . .
C3 C 0.8536(2) 0.21049(19) 0.42911(14) 0.0266(4) Uani 1 1 d . . .
C4 C 0.7796(2) 0.31774(18) 0.38241(14) 0.0251(4) Uani 1 1 d . . .
H4A H 0.8142 0.3967 0.4457 0.030 Uiso 1 1 calc R . .
C5 C 1.0053(2) 0.1947(2) 0.43562(15) 0.0357(5) Uani 1 1 d . . .
H5A H 1.0333 0.1210 0.4682 0.054 Uiso 1 1 calc R . .
H5B H 1.0865 0.2570 0.4078 0.054 Uiso 1 1 calc R . .
C6 C 0.8477(2) 0.38738(18) 0.29789(14) 0.0246(4) Uani 1 1 d . . .
C7 C 0.8634(2) 0.31078(19) 0.21025(14) 0.0284(4) Uani 1 1 d . . .
H7A H 0.8307 0.2104 0.2021 0.034 Uiso 1 1 calc R . .
C8 C 0.9262(2) 0.3794(2) 0.13480(15) 0.0330(4) Uani 1 1 d . . .
H8A H 0.9353 0.3257 0.0750 0.040 Uiso 1 1 calc R . .
C9 C 0.9757(2) 0.5250(2) 0.14596(16) 0.0365(5) Uani 1 1 d . . .
H9A H 1.0182 0.5718 0.0939 0.044 Uiso 1 1 calc R . .
C10 C 0.9630(3) 0.6025(2) 0.23314(17) 0.0389(5) Uani 1 1 d . . .
H10A H 0.9981 0.7031 0.2416 0.047 Uiso 1 1 calc R . .
C11 C 0.8994(2) 0.53429(19) 0.30821(15) 0.0324(4) Uani 1 1 d . . .
H11A H 0.8908 0.5887 0.3679 0.039 Uiso 1 1 calc R . .
C12 C 0.4810(2) 0.33756(18) 0.36590(14) 0.0263(4) Uani 1 1 d . . .
C13 C 0.4240(3) 0.5367(2) 0.30141(16) 0.0347(5) Uani 1 1 d . . .
H13A H 0.4592 0.5872 0.3777 0.042 Uiso 1 1 calc R . .
H13B H 0.2920 0.4933 0.2699 0.042 Uiso 1 1 calc R . .
C14 C 0.4967(2) 0.63683(19) 0.23432(15) 0.0312(4) Uani 1 1 d . . .
C15 C 0.6321(3) 0.7673(2) 0.28441(17) 0.0421(5) Uani 1 1 d . . .
H15A H 0.6735 0.7970 0.3618 0.051 Uiso 1 1 calc R . .
C16 C 0.7076(3) 0.8552(2) 0.2220(2) 0.0522(6) Uani 1 1 d . . .
H16A H 0.8011 0.9448 0.2569 0.063 Uiso 1 1 calc R . .
C17 C 0.6482(3) 0.8137(2) 0.1105(2) 0.0528(6) Uani 1 1 d . . .
H17A H 0.7012 0.8743 0.0683 0.063 Uiso 1 1 calc R . .
C18 C 0.5118(3) 0.6845(2) 0.05914(18) 0.0459(5) Uani 1 1 d . . .
H18A H 0.4697 0.6559 -0.0183 0.055 Uiso 1 1 calc R . .
C19 C 0.4366(3) 0.5967(2) 0.12153(16) 0.0364(5) Uani 1 1 d . . .
H19A H 0.3425 0.5075 0.0863 0.044 Uiso 1 1 calc R . .
C20 C 0.4835(2) 0.14020(18) 0.23570(14) 0.0270(4) Uani 1 1 d . . .
H20A H 0.5517 0.0790 0.2286 0.032 Uiso 1 1 calc R . .
H20B H 0.4933 0.2028 0.1817 0.032 Uiso 1 1 calc R . .
C21 C 0.2859(2) 0.0439(2) 0.20535(15) 0.0338(5) Uani 1 1 d . . .
H21A H 0.2675 0.0099 0.2722 0.041 Uiso 1 1 calc R . .
C22 C 0.1597(3) 0.1222(2) 0.16418(19) 0.0508(6) Uani 1 1 d . . .
H22A H 0.1847 0.2021 0.2219 0.076 Uiso 1 1 calc R . .
H22B H 0.0358 0.0563 0.1447 0.076 Uiso 1 1 calc R . .
H22C H 0.1779 0.1583 0.0995 0.076 Uiso 1 1 calc R . .
C23 C 0.2398(3) -0.0854(2) 0.11829(18) 0.0436(5) Uani 1 1 d . . .
H23A H 0.3122 -0.1410 0.1475 0.065 Uiso 1 1 calc R . .
H23B H 0.2646 -0.0538 0.0538 0.065 Uiso 1 1 calc R . .
H23C H 0.1129 -0.1447 0.0975 0.065 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'
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
_geom_angle_publ_flag
C2 N1 C1 113.89(14) . . ?
C2 N1 H1A 120.9(12) . . ?
C1 N1 H1A 123.1(12) . . ?
C12 O3 C13 117.31(13) . . ?
N1 C1 C12 110.09(14) . . ?
N1 C1 C20 110.44(14) . . ?
C12 C1 C20 111.31(14) . . ?
N1 C1 C4 100.74(13) . . ?
C12 C1 C4 110.24(13) . . ?
C20 C1 C4 113.54(13) . . ?
O1 C2 N1 126.39(16) . . ?
O1 C2 C3 126.52(16) . . ?
N1 C2 C3 107.09(14) . . ?
C5 C3 C2 123.26(17) . . ?
C5 C3 C4 130.12(16) . . ?
C2 C3 C4 106.62(14) . . ?
C3 C4 C6 117.62(14) . . ?
C3 C4 C1 101.55(13) . . ?
C6 C4 C1 118.62(13) . . ?
C3 C4 H4A 106.0 . . ?
C6 C4 H4A 106.0 . . ?
C1 C4 H4A 106.0 . . ?
C3 C5 H5A 120.0 . . ?
C3 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
C11 C6 C7 118.13(16) . . ?
C11 C6 C4 119.08(16) . . ?
C7 C6 C4 122.78(15) . . ?
C8 C7 C6 120.64(17) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C9 C8 C7 120.40(18) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 119.58(17) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C9 C10 C11 120.18(18) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C10 C11 C6 121.06(18) . . ?
C10 C11 H11A 119.5 . . ?
C6 C11 H11A 119.5 . . ?
O2 C12 O3 125.23(16) . . ?
O2 C12 C1 125.45(16) . . ?
O3 C12 C1 109.32(14) . . ?
O3 C13 C14 105.32(14) . . ?
O3 C13 H13A 110.7 . . ?
C14 C13 H13A 110.7 . . ?
O3 C13 H13B 110.7 . . ?
C14 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C15 C14 C19 119.02(18) . . ?
C15 C14 C13 120.43(18) . . ?
C19 C14 C13 120.44(17) . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C17 C18 C19 119.3(2) . . ?
C17 C18 H18A 120.3 . . ?
C19 C18 H18A 120.3 . . ?
C14 C19 C18 120.94(19) . . ?
C14 C19 H19A 119.5 . . ?
C18 C19 H19A 119.5 . . ?
C1 C20 C21 115.82(14) . . ?
C1 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
C1 C20 H20B 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C23 C21 C22 109.48(16) . . ?
C23 C21 C20 109.80(15) . . ?
C22 C21 C20 112.47(15) . . ?
C23 C21 H21A 108.3 . . ?
C22 C21 H21A 108.3 . . ?
C20 C21 H21A 108.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.346(2) . ?
N1 C1 1.455(2) . ?
N1 H1A 0.879(3) . ?
O1 C2 1.232(2) . ?
O2 C12 1.198(2) . ?
O3 C12 1.329(2) . ?
O3 C13 1.463(2) . ?
C1 C12 1.520(2) . ?
C1 C20 1.536(2) . ?
C1 C4 1.578(2) . ?
C2 C3 1.491(2) . ?
C3 C5 1.321(2) . ?
C3 C4 1.508(2) . ?
C4 C6 1.512(2) . ?
C4 H4A 1.0000 . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 C11 1.390(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.384(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.378(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.378(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C13 C14 1.494(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.380(3) . ?
C14 C19 1.382(3) . ?
C15 C16 1.385(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.369(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.377(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C21 1.539(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C23 1.521(3) . ?
C21 C22 1.529(3) . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.879(3) 1.982(4) 2.8581(19) 174.2(17) 2_656
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
_geom_torsion_publ_flag
C2 N1 C1 C12 -143.31(15) . . . . ?
C2 N1 C1 C20 93.38(17) . . . . ?
C2 N1 C1 C4 -26.92(19) . . . . ?
C1 N1 C2 O1 -169.37(17) . . . . ?
C1 N1 C2 C3 11.1(2) . . . . ?
O1 C2 C3 C5 11.2(3) . . . . ?
N1 C2 C3 C5 -169.30(18) . . . . ?
O1 C2 C3 C4 -168.63(18) . . . . ?
N1 C2 C3 C4 10.92(19) . . . . ?
C5 C3 C4 C6 23.2(3) . . . . ?
C2 C3 C4 C6 -157.07(15) . . . . ?
C5 C3 C4 C1 154.38(19) . . . . ?
C2 C3 C4 C1 -25.86(17) . . . . ?
N1 C1 C4 C3 30.55(16) . . . . ?
C12 C1 C4 C3 146.83(14) . . . . ?
C20 C1 C4 C3 -87.50(16) . . . . ?
N1 C1 C4 C6 161.14(15) . . . . ?
C12 C1 C4 C6 -82.59(18) . . . . ?
C20 C1 C4 C6 43.1(2) . . . . ?
C3 C4 C6 C11 -133.12(17) . . . . ?
C1 C4 C6 C11 103.99(19) . . . . ?
C3 C4 C6 C7 46.0(2) . . . . ?
C1 C4 C6 C7 -76.9(2) . . . . ?
C11 C6 C7 C8 -1.0(2) . . . . ?
C4 C6 C7 C8 179.88(15) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C6 0.2(3) . . . . ?
C7 C6 C11 C10 0.6(3) . . . . ?
C4 C6 C11 C10 179.77(16) . . . . ?
C13 O3 C12 O2 1.2(2) . . . . ?
C13 O3 C12 C1 -179.36(14) . . . . ?
N1 C1 C12 O2 -7.6(2) . . . . ?
C20 C1 C12 O2 115.18(18) . . . . ?
C4 C1 C12 O2 -117.90(18) . . . . ?
N1 C1 C12 O3 172.92(13) . . . . ?
C20 C1 C12 O3 -64.27(17) . . . . ?
C4 C1 C12 O3 62.65(17) . . . . ?
C12 O3 C13 C14 169.55(14) . . . . ?
O3 C13 C14 C15 -103.35(19) . . . . ?
O3 C13 C14 C19 72.8(2) . . . . ?
C19 C14 C15 C16 -0.9(3) . . . . ?
C13 C14 C15 C16 175.32(17) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C15 C14 C19 C18 0.8(3) . . . . ?
C13 C14 C19 C18 -175.43(17) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
N1 C1 C20 C21 61.27(19) . . . . ?
C12 C1 C20 C21 -61.33(19) . . . . ?
C4 C1 C20 C21 173.57(14) . . . . ?
C1 C20 C21 C23 -154.19(15) . . . . ?
C1 C20 C21 C22 83.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181756
