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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/68/4506858.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_4506858
loop_
_publ_author_name
'Wells, Kirk E.'
'Weatherhead, Robin A.'
'Murigi, Francis N.'
'Nichol, Gary S.'
'Carducci, Michael D.'
'Selby, Hugh D.'
'Mash, Eugene A.'
_publ_section_title
;
 Organic Crystal Engineering with 1,4-Piperazine-2,5-diones. 8. Synthesis,
 Crystal Packing, and Thermochemistry of Piperazinediones Derived from
 2-Amino-4,7-dialkoxyindan-2-carboxylic Acids
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5056
_journal_paper_doi               10.1021/cg301003p
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C28 H34 N2 O6'
_chemical_formula_sum            'C28 H34 N2 O6'
_chemical_formula_weight         494.57
_chemical_name_common            C2-tail
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.328(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8429(13)
_cell_length_b                   6.1190(8)
_cell_length_c                   21.635(3)
_cell_measurement_reflns_used    4815
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.7515
_cell_measurement_theta_min      2.254
_cell_volume                     1302.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_measurement_specimen_support 'glass fiber'
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12750
_diffrn_reflns_theta_full        26.85
_diffrn_reflns_theta_max         26.85
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0.28
_diffrn_standards_interval_count 1818
_diffrn_standards_number         66
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.955517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0423
_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)+(0.0412P)²+0.5387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                1900
_reflns_number_total             2691
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301003p_si_002.cif
_cod_data_source_block           kw04s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4506858
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 O 0.42405(12) 0.85984(18) 0.06037(5) 0.0299(3) Uani 1 1 d .
O8 O 0.47639(11) 0.86866(19) -0.22686(5) 0.0283(3) Uani 1 1 d .
O5 O 0.96462(11) 0.8396(2) -0.09314(5) 0.0311(3) Uani 1 1 d .
C5 C 0.84830(15) 0.8605(3) -0.12917(7) 0.0228(4) Uani 1 1 d .
C8 C 0.60146(16) 0.8750(3) -0.19685(7) 0.0216(4) Uani 1 1 d .
C4 C 0.74281(16) 0.7177(2) -0.11565(7) 0.0202(4) Uani 1 1 d .
N1 N 0.53260(13) 0.7055(2) -0.01867(6) 0.0212(3) Uani 1 1 d .
H1A H 0.5519(17) 0.842(3) -0.0327(8) 0.025 Uiso 1 1 d .
C9 C 0.62143(15) 0.7250(2) -0.14914(7) 0.0201(4) Uani 1 1 d .
C2 C 0.57954(15) 0.5264(2) -0.05733(7) 0.0194(3) Uani 1 1 d .
C1 C 0.45950(15) 0.6950(2) 0.03233(7) 0.0197(3) Uani 1 1 d .
C3 C 0.73506(15) 0.5494(3) -0.06495(7) 0.0217(4) Uani 1 1 d .
H3A H 0.7802 0.6015 -0.0263 0.026 Uiso 1 1 calc R
H3B H 0.7765 0.4092 -0.0775 0.026 Uiso 1 1 calc R
C7 C 0.70574(17) 1.0173(3) -0.21038(8) 0.0252(4) Uani 1 1 d .
H7A H 0.6938 1.1209 -0.2428 0.030 Uiso 1 1 calc R
C10 C 0.52282(16) 0.5617(3) -0.12396(7) 0.0215(4) Uani 1 1 d .
H10A H 0.5232 0.4241 -0.1480 0.026 Uiso 1 1 calc R
H10B H 0.4293 0.6213 -0.1239 0.026 Uiso 1 1 calc R
C6 C 0.82855(17) 1.0097(3) -0.17671(8) 0.0265(4) Uani 1 1 d .
H6A H 0.8995 1.1082 -0.1865 0.032 Uiso 1 1 calc R
C81 C 0.45075(19) 1.0306(3) -0.27299(9) 0.0357(5) Uani 1 1 d .
H81A H 0.5165 1.0161 -0.3067 0.043 Uiso 1 1 calc R
H81B H 0.4602 1.1785 -0.2549 0.043 Uiso 1 1 calc R
C82 C 0.3087(2) 0.9972(3) -0.29775(10) 0.0463(5) Uani 1 1 d .
H82A H 0.2891 1.1042 -0.3305 0.069 Uiso 1 1 calc R
H82B H 0.2443 1.0166 -0.2643 0.069 Uiso 1 1 calc R
H82C H 0.2998 0.8492 -0.3146 0.069 Uiso 1 1 calc R
C51 C 1.07017(18) 0.9964(3) -0.10212(9) 0.0362(5) Uani 1 1 d .
H51A H 1.0356 1.1461 -0.0952 0.043 Uiso 1 1 calc R
H51B H 1.1036 0.9871 -0.1449 0.043 Uiso 1 1 calc R
C52 C 1.1831(2) 0.9446(4) -0.05634(10) 0.0473(5) Uani 1 1 d .
H52A H 1.2595 1.0442 -0.0628 0.071 Uiso 1 1 calc R
H52B H 1.2132 0.7935 -0.0622 0.071 Uiso 1 1 calc R
H52C H 1.1502 0.9625 -0.0142 0.071 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
C8 O8 C81 116.86(13) . .
C5 O5 C51 117.26(13) . .
O5 C5 C6 125.61(14) . .
O5 C5 C4 115.92(14) . .
C6 C5 C4 118.47(15) . .
O8 C8 C7 125.25(14) . .
O8 C8 C9 116.09(14) . .
C7 C8 C9 118.66(15) . .
C9 C4 C5 120.56(15) . .
C9 C4 C3 110.21(13) . .
C5 C4 C3 129.17(15) . .
C1 N1 C2 128.49(13) . .
C1 N1 H1A 116.2(11) . .
C2 N1 H1A 115.2(11) . .
C4 C9 C8 121.00(14) . .
C4 C9 C10 110.21(13) . .
C8 C9 C10 128.73(14) . .
N1 C2 C1 112.41(12) . 3_665
N1 C2 C10 108.44(12) . .
C1 C2 C10 111.66(13) 3_665 .
N1 C2 C3 108.61(12) . .
C1 C2 C3 112.30(12) 3_665 .
C10 C2 C3 102.93(12) . .
O1 C1 N1 122.22(14) . .
O1 C1 C2 118.70(13) . 3_665
N1 C1 C2 119.07(13) . 3_665
C4 C3 C2 101.90(12) . .
C4 C3 H3A 111.4 . .
C2 C3 H3A 111.4 . .
C4 C3 H3B 111.4 . .
C2 C3 H3B 111.4 . .
H3A C3 H3B 109.3 . .
C8 C7 C6 120.39(15) . .
C8 C7 H7A 119.8 . .
C6 C7 H7A 119.8 . .
C9 C10 C2 102.02(12) . .
C9 C10 H10A 111.4 . .
C2 C10 H10A 111.4 . .
C9 C10 H10B 111.4 . .
C2 C10 H10B 111.4 . .
H10A C10 H10B 109.2 . .
C5 C6 C7 120.91(15) . .
C5 C6 H6A 119.5 . .
C7 C6 H6A 119.5 . .
O8 C81 C82 107.70(15) . .
O8 C81 H81A 110.2 . .
C82 C81 H81A 110.2 . .
O8 C81 H81B 110.2 . .
C82 C81 H81B 110.2 . .
H81A C81 H81B 108.5 . .
C81 C82 H82A 109.5 . .
C81 C82 H82B 109.5 . .
H82A C82 H82B 109.5 . .
C81 C82 H82C 109.5 . .
H82A C82 H82C 109.5 . .
H82B C82 H82C 109.5 . .
O5 C51 C52 107.29(16) . .
O5 C51 H51A 110.3 . .
C52 C51 H51A 110.3 . .
O5 C51 H51B 110.3 . .
C52 C51 H51B 110.3 . .
H51A C51 H51B 108.5 . .
C51 C52 H52A 109.5 . .
C51 C52 H52B 109.5 . .
H52A C52 H52B 109.5 . .
C51 C52 H52C 109.5 . .
H52A C52 H52C 109.5 . .
H52B C52 H52C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2315(19) .
O8 C8 1.3789(19) .
O8 C81 1.425(2) .
O5 C5 1.3761(19) .
O5 C51 1.431(2) .
C5 C6 1.386(2) .
C5 C4 1.393(2) .
C8 C7 1.383(2) .
C8 C9 1.392(2) .
C4 C9 1.384(2) .
C4 C3 1.508(2) .
N1 C1 1.333(2) .
N1 C2 1.460(2) .
N1 H1A 0.911(18) .
C9 C10 1.504(2) .
C2 C1 1.512(2) 3_665
C2 C10 1.549(2) .
C2 C3 1.550(2) .
C1 C2 1.512(2) 3_665
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C7 C6 1.398(2) .
C7 H7A 0.9500 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C6 H6A 0.9500 .
C81 C82 1.500(3) .
C81 H81A 0.9900 .
C81 H81B 0.9900 .
C82 H82A 0.9800 .
C82 H82B 0.9800 .
C82 H82C 0.9800 .
C51 C52 1.505(3) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 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 0.911(18) 1.936(19) 2.8441(18) 174.6(16) 3_675
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_4
C51 O5 C5 C6 5.3(2) . .
C51 O5 C5 C4 -174.54(14) . .
C81 O8 C8 C7 -3.9(2) . .
C81 O8 C8 C9 175.86(14) . .
O5 C5 C4 C9 -179.98(14) . .
C6 C5 C4 C9 0.1(2) . .
O5 C5 C4 C3 3.3(2) . .
C6 C5 C4 C3 -176.64(15) . .
C5 C4 C9 C8 -0.2(2) . .
C3 C4 C9 C8 177.12(14) . .
C5 C4 C9 C10 -177.66(14) . .
C3 C4 C9 C10 -0.33(18) . .
O8 C8 C9 C4 -179.63(14) . .
C7 C8 C9 C4 0.1(2) . .
O8 C8 C9 C10 -2.7(2) . .
C7 C8 C9 C10 177.04(15) . .
C1 N1 C2 C1 -2.2(2) . 3_665
C1 N1 C2 C10 121.74(16) . .
C1 N1 C2 C3 -127.09(16) . .
C2 N1 C1 O1 -178.66(15) . .
C2 N1 C1 C2 2.3(3) . 3_665
C9 C4 C3 C2 -21.29(16) . .
C5 C4 C3 C2 155.75(16) . .
N1 C2 C3 C4 -81.34(14) . .
C1 C2 C3 C4 153.71(13) 3_665 .
C10 C2 C3 C4 33.48(14) . .
O8 C8 C7 C6 179.79(15) . .
C9 C8 C7 C6 0.1(2) . .
C4 C9 C10 C2 21.82(16) . .
C8 C9 C10 C2 -155.38(15) . .
N1 C2 C10 C9 81.23(14) . .
C1 C2 C10 C9 -154.39(12) 3_665 .
C3 C2 C10 C9 -33.72(15) . .
O5 C5 C6 C7 -179.83(15) . .
C4 C5 C6 C7 0.1(2) . .
C8 C7 C6 C5 -0.2(2) . .
C8 O8 C81 C82 -178.23(15) . .
C5 O5 C51 C52 177.97(15) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102456980
