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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/4/50/17/4501787.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_4501787
loop_
_publ_author_name
'Kumar, Jitendra'
'Awasthi, Shubhra'
'Verma, Sandeep'
_publ_section_title
;
 Contrasting Crystallographic Signatures of 9-Carboxypropyl Adeninium
 Cation: Adenine Dimerization vs Carboxylic Group Interaction
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3555
_journal_paper_doi               10.1021/cg100470u
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C8 H10 N5 O2, H2 O, Cl'
_chemical_formula_sum            'C8 H12 Cl N5 O3'
_chemical_formula_weight         261.68
_chemical_name_common            '3-(N9-adeninyl)propanoic acid.HCl'
_chemical_name_systematic
;
 6-amino-9-(2-carboxyethyl)-9H-purin-1-ium chloride
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2ac -2n'
_symmetry_space_group_name_H-M   'P n 21 a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.697(4)
_cell_length_b                   15.767(2)
_cell_length_c                   5.1080(7)
_cell_measurement_reflns_used    4044
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.58
_cell_volume                     2311.2(5)
_computing_cell_refinement       'SMART 5.628 (Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT+ 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'diamond 3.1d'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area Detector'
_diffrn_measurement_method       'Phi-Omega 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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12043
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.9357
_exptl_absorpt_correction_T_min  0.9357
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4044
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0936P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                3071
_reflns_number_total             4044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100470u_si_002.cif
_cod_data_source_block           adduct1
_cod_database_code               4501787
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, y, -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
C2 C 0.0650(2) 0.0030(5) 0.7444(7) 0.0484(18) Uani 1 1 d .
H2 H 0.0647 -0.0358 0.8815 0.058 Uiso 1 1 calc R
C2' C 0.18394(19) 0.3532(5) 0.2716(8) 0.0490(18) Uani 1 1 d .
H2' H 0.1843 0.3924 0.1354 0.059 Uiso 1 1 calc R
C4' C 0.21776(12) 0.2589(3) 0.5271(7) 0.0434(9) Uani 1 1 d .
C4 C 0.03113(12) 0.0958(3) 0.4842(7) 0.0422(8) Uani 1 1 d .
C5 C 0.07127(12) 0.1136(3) 0.3449(8) 0.0415(9) Uani 1 1 d .
C5' C 0.17773(12) 0.2419(3) 0.6681(9) 0.0424(9) Uani 1 1 d .
C6' C 0.13733(12) 0.2868(3) 0.6040(7) 0.0421(9) Uani 1 1 d .
C6 C 0.11172(12) 0.0696(3) 0.4162(7) 0.0442(9) Uani 1 1 d .
C8' C 0.23056(15) 0.1632(4) 0.8240(10) 0.0508(11) Uani 1 1 d .
H8' H 0.2462 0.1234 0.9258 0.061 Uiso 1 1 calc R
C8 C 0.01882(14) 0.1916(4) 0.1872(9) 0.0490(11) Uani 1 1 d .
H8 H 0.0032 0.2311 0.0842 0.059 Uiso 1 1 calc R
C10 C -0.05233(11) 0.1431(3) 0.4373(8) 0.0508(10) Uani 1 1 d .
H10A H -0.0663 0.1978 0.4002 0.061 Uiso 1 1 calc R
H10B H -0.0570 0.1306 0.6214 0.061 Uiso 1 1 calc R
C10' C 0.30112(12) 0.2116(3) 0.5658(8) 0.0504(10) Uani 1 1 d .
H10C H 0.3051 0.2250 0.3819 0.060 Uiso 1 1 calc R
H10D H 0.3152 0.1566 0.5981 0.060 Uiso 1 1 calc R
C11' C 0.32542(18) 0.2790(5) 0.7331(8) 0.0471(14) Uani 1 1 d .
H11C H 0.3098 0.3330 0.7092 0.057 Uiso 1 1 calc R
H11D H 0.3228 0.2635 0.9163 0.057 Uiso 1 1 calc R
C11 C -0.07504(19) 0.0766(5) 0.2754(9) 0.0485(15) Uani 1 1 d .
H11A H -0.0589 0.0233 0.3023 0.058 Uiso 1 1 calc R
H11B H -0.0718 0.0916 0.0921 0.058 Uiso 1 1 calc R
C12 C -0.12622(14) 0.0642(3) 0.3367(10) 0.0508(10) Uani 1 1 d .
C12' C 0.37509(14) 0.2883(3) 0.6643(10) 0.0542(10) Uani 1 1 d .
N1' N 0.14227(11) 0.3410(3) 0.3999(7) 0.0494(8) Uani 1 1 d .
H1' H 0.1183 0.3691 0.3482 0.059 Uiso 1 1 calc R
N1 N 0.10629(10) 0.0160(2) 0.6194(6) 0.0465(8) Uani 1 1 d .
H1 H 0.1303 -0.0115 0.6733 0.056 Uiso 1 1 calc R
N3 N 0.02604(12) 0.0408(3) 0.6867(8) 0.0491(9) Uani 1 1 d .
N3' N 0.22270(12) 0.3147(3) 0.3244(8) 0.0511(10) Uani 1 1 d .
N6 N 0.15245(12) 0.0775(4) 0.2938(7) 0.0500(11) Uani 1 1 d .
H6A H 0.1760 0.0480 0.3441 0.060 Uiso 1 1 calc R
H6B H 0.1552 0.1120 0.1644 0.060 Uiso 1 1 calc R
N6' N 0.09649(13) 0.2790(4) 0.7258(7) 0.0509(12) Uani 1 1 d .
H6'A H 0.0729 0.3084 0.6752 0.061 Uiso 1 1 calc R
H6'B H 0.0937 0.2444 0.8552 0.061 Uiso 1 1 calc R
N7 N 0.06339(10) 0.1749(3) 0.1596(8) 0.0493(8) Uani 1 1 d .
N7' N 0.18618(10) 0.1814(3) 0.8544(7) 0.0486(8) Uani 1 1 d .
N9' N 0.25134(10) 0.2082(3) 0.6291(7) 0.0466(8) Uani 1 1 d .
N9 N -0.00267(10) 0.1461(3) 0.3797(7) 0.0475(8) Uani 1 1 d .
O1 O -0.14571(13) 0.0038(4) 0.1983(8) 0.0752(14) Uani 1 1 d D
O1' O 0.39480(13) 0.3485(4) 0.8046(9) 0.0769(14) Uani 1 1 d D
O2' O 0.39614(11) 0.2472(3) 0.5095(7) 0.0809(11) Uani 1 1 d .
O2 O -0.14723(11) 0.1065(3) 0.4917(7) 0.0791(11) Uani 1 1 d .
O1W O 0.18639(13) -0.0631(4) 0.7782(7) 0.0664(15) Uani 1 1 d D
O2W O 0.06261(16) 0.4170(4) 0.2479(7) 0.0709(17) Uani 1 1 d D
Cl1 Cl -0.24967(4) -0.01878(14) 0.2214(2) 0.0582(4) Uani 1 1 d .
Cl1' Cl 0.49859(4) 0.37434(15) 0.7502(2) 0.0567(4) Uani 1 1 d .
H1'A H 0.4248(9) 0.347(9) 0.775(16) 0.16(4) Uiso 1 1 d D
H1A H -0.1767(7) 0.003(5) 0.216(9) 0.064(18) Uiso 1 1 d D
H1W1 H 0.2093(14) -0.067(5) 0.664(8) 0.11(2) Uiso 1 1 d D
H1W2 H 0.040(3) 0.419(15) 0.14(2) 0.33(8) Uiso 1 1 d D
H2W1 H 0.2063(12) -0.054(4) 0.903(6) 0.069(15) Uiso 1 1 d D
H2W2 H 0.044(3) 0.398(8) 0.362(17) 0.21(5) Uiso 1 1 d D
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
N3 C2 N1 124.9(5)
N3 C2 H2 117.5
N1 C2 H2 117.5
N3' C2' N1' 125.5(5)
N3' C2' H2' 117.2
N1' C2' H2' 117.2
N9' C4' N3' 126.7(3)
N9' C4' C5' 106.0(3)
N3' C4' C5' 127.3(4)
N3 C4 N9 126.5(3)
N3 C4 C5 127.7(4)
N9 C4 C5 105.9(3)
N7 C5 C4 111.1(4)
N7 C5 C6 131.7(3)
C4 C5 C6 117.1(4)
N7' C5' C4' 110.5(3)
N7' C5' C6' 131.5(3)
C4' C5' C6' 118.0(4)
N6' C6' N1' 120.7(4)
N6' C6' C5' 124.9(4)
N1' C6' C5' 114.4(3)
N6 C6 N1 121.5(4)
N6 C6 C5 124.0(4)
N1 C6 C5 114.5(3)
N7' C8' N9' 113.4(4)
N7' C8' H8' 123.3
N9' C8' H8' 123.3
N7 C8 N9 114.3(4)
N7 C8 H8 122.8
N9 C8 H8 122.8
N9 C10 C11 109.9(4)
N9 C10 H10A 109.7
C11 C10 H10A 109.7
N9 C10 H10B 109.7
C11 C10 H10B 109.7
H10A C10 H10B 108.2
N9' C10' C11' 110.3(3)
N9' C10' H10C 109.6
C11' C10' H10C 109.6
N9' C10' H10D 109.6
C11' C10' H10D 109.6
H10C C10' H10D 108.1
C12' C11' C10' 112.1(4)
C12' C11' H11C 109.2
C10' C11' H11C 109.2
C12' C11' H11D 109.2
C10' C11' H11D 109.2
H11C C11' H11D 107.9
C10 C11 C12 113.6(4)
C10 C11 H11A 108.8
C12 C11 H11A 108.8
C10 C11 H11B 108.8
C12 C11 H11B 108.8
H11A C11 H11B 107.7
O2 C12 O1 123.1(4)
O2 C12 C11 123.6(5)
O1 C12 C11 113.3(4)
O2' C12' O1' 122.5(4)
O2' C12' C11' 126.5(5)
O1' C12' C11' 110.9(5)
C6' N1' C2' 123.0(4)
C6' N1' H1' 118.5
C2' N1' H1' 118.5
C6 N1 C2 123.8(4)
C6 N1 H1 118.1
C2 N1 H1 118.1
C2 N3 C4 111.9(4)
C2' N3' C4' 111.8(4)
C6 N6 H6A 120.0
C6 N6 H6B 120.0
H6A N6 H6B 120.0
C6' N6' H6'A 120.0
C6' N6' H6'B 120.0
H6'A N6' H6'B 120.0
C8 N7 C5 103.2(4)
C8' N7' C5' 104.0(3)
C4' N9' C8' 106.1(3)
C4' N9' C10' 125.9(3)
C8' N9' C10' 127.4(3)
C4 N9 C8 105.5(3)
C4 N9 C10 126.8(4)
C8 N9 C10 127.3(3)
C12 O1 H1A 112(4)
C12' O1' H1'A 108(8)
H1W1 O1W H2W1 91(3)
H1W2 O2W H2W2 89(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N3 1.301(7)
C2 N1 1.361(6)
C2 H2 0.9300
C2' N3' 1.295(7)
C2' N1' 1.377(6)
C2' H2' 0.9300
C4' N9' 1.356(5)
C4' N3' 1.367(6)
C4' C5' 1.382(5)
C4 N3 1.357(6)
C4 N9 1.362(5)
C4 C5 1.383(5)
C5 N7 1.372(6)
C5 C6 1.401(6)
C5' N7' 1.369(6)
C5' C6' 1.398(6)
C6' N6' 1.333(5)
C6' N1' 1.355(5)
C6 N6 1.332(5)
C6 N1 1.347(5)
C8' N7' 1.315(5)
C8' N9' 1.360(6)
C8' H8' 0.9300
C8 N7 1.313(5)
C8 N9 1.364(6)
C8 H8 0.9300
C10 N9 1.456(4)
C10 C11 1.486(8)
C10 H10A 0.9700
C10 H10B 0.9700
C10' N9' 1.466(4)
C10' C11' 1.532(8)
C10' H10C 0.9700
C10' H10D 0.9700
C11' C12' 1.475(6)
C11' H11C 0.9700
C11' H11D 0.9700
C11 C12 1.514(7)
C11 H11A 0.9700
C11 H11B 0.9700
C12 O2 1.198(5)
C12 O1 1.311(7)
C12' O2' 1.188(5)
C12' O1' 1.317(7)
N1' H1' 0.8600
N1 H1 0.8600
N6 H6A 0.8600
N6 H6B 0.8600
N6' H6'A 0.8600
N6' H6'B 0.8600
O1 H1A 0.893(19)
O1' H1'A 0.87(2)
O1W H1W1 0.883(19)
O1W H2W1 0.869(19)
O2W H1W2 0.86(2)
O2W H2W2 0.86(2)
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
N3 C4 C5 N7 -177.9(4)
N9 C4 C5 N7 1.1(5)
N3 C4 C5 C6 0.8(7)
N9 C4 C5 C6 179.8(4)
N9' C4' C5' N7' -0.2(5)
N3' C4' C5' N7' 179.3(4)
N9' C4' C5' C6' 179.4(4)
N3' C4' C5' C6' -1.2(7)
N7' C5' C6' N6' 1.1(9)
C4' C5' C6' N6' -178.3(5)
N7' C5' C6' N1' -178.5(5)
C4' C5' C6' N1' 2.1(6)
N7 C5 C6 N6 -4.4(8)
C4 C5 C6 N6 177.3(4)
N7 C5 C6 N1 176.8(5)
C4 C5 C6 N1 -1.5(6)
N9' C10' C11' C12' -176.5(4)
N9 C10 C11 C12 175.6(4)
C10 C11 C12 O2 3.4(8)
C10 C11 C12 O1 -178.2(5)
C10' C11' C12' O2' -3.8(8)
C10' C11' C12' O1' 177.9(5)
N6' C6' N1' C2' 178.3(5)
C5' C6' N1' C2' -2.1(6)
N3' C2' N1' C6' 1.1(9)
N6 C6 N1 C2 -177.3(5)
C5 C6 N1 C2 1.6(7)
N3 C2 N1 C6 -0.8(9)
N1 C2 N3 C4 -0.1(8)
N9 C4 N3 C2 -178.8(5)
C5 C4 N3 C2 0.0(7)
N1' C2' N3' C4' 0.1(8)
N9' C4' N3' C2' 179.4(5)
C5' C4' N3' C2' 0.0(7)
N9 C8 N7 C5 0.7(6)
C4 C5 N7 C8 -1.1(6)
C6 C5 N7 C8 -179.6(5)
N9' C8' N7' C5' -0.1(6)
C4' C5' N7' C8' 0.1(6)
C6' C5' N7' C8' -179.3(5)
N3' C4' N9' C8' -179.3(5)
C5' C4' N9' C8' 0.1(5)
N3' C4' N9' C10' 9.0(7)
C5' C4' N9' C10' -171.6(4)
N7' C8' N9' C4' 0.0(6)
N7' C8' N9' C10' 171.5(4)
C11' C10' N9' C4' 84.4(5)
C11' C10' N9' C8' -85.6(6)
N3 C4 N9 C8 178.4(4)
C5 C4 N9 C8 -0.6(5)
N3 C4 N9 C10 -9.3(7)
C5 C4 N9 C10 171.7(4)
N7 C8 N9 C4 -0.1(6)
N7 C8 N9 C10 -172.4(4)
C11 C10 N9 C4 -83.6(5)
C11 C10 N9 C8 87.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144755
