#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/59/7105919.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_7105919
loop_
_publ_author_name
'N. Nagapradeep'
'Sandeep Verma'
_publ_section_title
;
 Characterization of an unprecedented organomercury adduct via
 Hg(II)-mediated cyclization of N9-propargylguanine
;
_journal_name_full               Chem.Commun.
_journal_page_first              1755
_journal_paper_doi               10.1039/c0cc03123b
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         ' C8 H8 N5 O, Cl O4, H2 O '
_chemical_formula_sum            'C8 H10 Cl N5 O6'
_chemical_formula_weight         307.66
_chemical_name_common            '7-protonated 9-propargylguanine'
_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                72.577(4)
_cell_angle_beta                 84.086(5)
_cell_angle_gamma                76.667(4)
_cell_formula_units_Z            4
_cell_length_a                   7.4810(18)
_cell_length_b                   13.111(3)
_cell_length_c                   13.431(3)
_cell_measurement_reflns_used    5671
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.6
_cell_volume                     1222.2(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_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.931
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7842
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.9333
_exptl_absorpt_correction_T_min  0.9238
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5671
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0597
_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)+(0.1232P)²+2.8260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.2393
_reflns_number_gt                4694
_reflns_number_total             5671
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03123B.TXT
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7105919
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
Cl1' Cl 0.48345(11) 0.35133(7) -0.38453(6) 0.0202(2) Uani 1 1 d . . .
Cl1 Cl 0.14376(11) 1.13370(7) -0.75892(6) 0.0214(2) Uani 1 1 d . . .
O1 O 0.0797(3) 0.59286(19) -0.67751(19) 0.0216(5) Uani 1 1 d . . .
O5' O 0.3282(4) 0.3961(2) -0.4508(2) 0.0260(6) Uani 1 1 d . . .
O1W O 0.0801(4) 0.5861(2) -0.40728(19) 0.0214(5) Uani 1 1 d D . .
O3 O 0.1713(4) 1.1934(2) -0.6903(2) 0.0294(6) Uani 1 1 d . . .
O1' O 0.1307(4) 1.5968(2) -0.9432(2) 0.0270(6) Uani 1 1 d . . .
O5 O -0.0032(4) 1.1989(2) -0.8279(2) 0.0334(7) Uani 1 1 d . . .
O2' O 0.4880(4) 0.4236(2) -0.3230(2) 0.0320(6) Uani 1 1 d . . .
O2 O 0.3075(4) 1.1107(3) -0.8209(2) 0.0303(6) Uani 1 1 d . . .
O4' O 0.4663(4) 0.2463(2) -0.3152(2) 0.0317(6) Uani 1 1 d . . .
N1 N -0.0463(4) 0.7305(2) -0.8180(2) 0.0234(6) Uani 1 1 d . . .
H1 H -0.0113 0.6869 -0.8564 0.028 Uiso 1 1 calc R . .
O3' O 0.6481(4) 0.3391(2) -0.4485(2) 0.0282(6) Uani 1 1 d . . .
N2' N 0.4464(5) 1.3563(3) -0.6611(2) 0.0271(7) Uani 1 1 d . . .
H2C H 0.5201 1.2973 -0.6293 0.033 Uiso 1 1 calc R . .
H2D H 0.3911 1.4019 -0.6276 0.033 Uiso 1 1 calc R . .
N9 N -0.2216(4) 0.9286(2) -0.6422(2) 0.0224(6) Uani 1 1 d . . .
O2W O 0.1147(4) 1.5852(2) -1.2027(2) 0.0304(6) Uani 1 1 d D . .
N1' N 0.2966(4) 1.4721(2) -0.8058(2) 0.0240(6) Uani 1 1 d . . .
H1' H 0.2514 1.5137 -0.7666 0.029 Uiso 1 1 calc R . .
N2 N -0.1669(5) 0.8565(3) -0.9671(2) 0.0311(8) Uani 1 1 d . . .
H2A H -0.2265 0.9201 -1.0003 0.037 Uiso 1 1 calc R . .
H2B H -0.1257 0.8077 -0.9992 0.037 Uiso 1 1 calc R . .
N3 N -0.2019(4) 0.9093(2) -0.8168(2) 0.0215(6) Uani 1 1 d . . .
N7 N -0.0725(4) 0.7670(2) -0.5579(2) 0.0215(6) Uani 1 1 d . . .
H7 H -0.0234 0.7119 -0.5083 0.026 Uiso 1 1 calc R . .
O4 O 0.0952(4) 1.0323(2) -0.6985(2) 0.0343(7) Uani 1 1 d . . .
N3' N 0.5035(4) 1.3068(2) -0.8130(2) 0.0221(6) Uani 1 1 d . . .
N9' N 0.5140(4) 1.2815(2) -0.9849(2) 0.0216(6) Uani 1 1 d . . .
C4 C -0.1658(5) 0.8726(3) -0.7148(3) 0.0207(7) Uani 1 1 d . . .
C10 C -0.3389(6) 1.0835(3) -0.5740(3) 0.0304(8) Uani 1 1 d . . .
C8 C -0.1622(5) 0.8633(3) -0.5473(3) 0.0203(7) Uani 1 1 d . . .
H8 H -0.1812 0.8827 -0.4853 0.024 Uiso 1 1 calc R . .
N7' N 0.3186(4) 1.4293(3) -1.0648(2) 0.0243(6) Uani 1 1 d . . .
H7' H 0.2529 1.4784 -1.1126 0.029 Uiso 1 1 calc R . .
C5' C 0.3246(5) 1.4309(3) -0.9628(3) 0.0233(7) Uani 1 1 d . . .
C2' C 0.4180(5) 1.3772(3) -0.7617(3) 0.0231(7) Uani 1 1 d . . .
C11' C 0.7213(6) 1.1121(3) -1.1351(3) 0.0292(8) Uani 1 1 d . . .
H11' H 0.7430 1.0907 -1.1961 0.035 Uiso 1 1 calc R . .
C9' C 0.6512(5) 1.1776(3) -0.9632(3) 0.0254(7) Uani 1 1 d . . .
H9C H 0.7627 1.1878 -0.9401 0.031 Uiso 1 1 calc R . .
H9D H 0.6040 1.1227 -0.9076 0.031 Uiso 1 1 calc R . .
C4' C 0.4498(5) 1.3373(3) -0.9132(3) 0.0214(7) Uani 1 1 d . . .
C6 C -0.0036(5) 0.6887(3) -0.7131(3) 0.0192(6) Uani 1 1 d . . .
C9 C -0.3247(5) 1.0435(3) -0.6655(3) 0.0243(7) Uani 1 1 d . . .
H9A H -0.2626 1.0890 -0.7226 0.029 Uiso 1 1 calc R . .
H9B H -0.4470 1.0484 -0.6870 0.029 Uiso 1 1 calc R . .
C8' C 0.4321(5) 1.3388(3) -1.0765(3) 0.0228(7) Uani 1 1 d . . .
H8' H 0.4520 1.3180 -1.1378 0.027 Uiso 1 1 calc R . .
C11 C -0.3421(6) 1.1135(3) -0.4990(3) 0.0345(9) Uani 1 1 d . . .
H11 H -0.3445 1.1370 -0.4400 0.041 Uiso 1 1 calc R . .
C10' C 0.6935(5) 1.1395(3) -1.0567(3) 0.0250(7) Uani 1 1 d . . .
C5 C -0.0712(5) 0.7699(3) -0.6605(3) 0.0217(7) Uani 1 1 d . . .
C6' C 0.2384(5) 1.5082(3) -0.9094(3) 0.0226(7) Uani 1 1 d . . .
C2 C -0.1384(5) 0.8338(3) -0.8660(3) 0.0226(7) Uani 1 1 d . . .
H2W1 H 0.0965 1.6509 -1.1986 0.034 Uiso 1 1 d D . .
H2W2 H 0.1407 1.5941 -1.2635 0.084 Uiso 1 1 d D . .
H1W1 H 0.177(4) 0.567(4) -0.437(3) 0.026(11) Uiso 1 1 d D . .
H1W2 H 0.025(10) 0.529(6) -0.403(6) 0.07(2) Uiso 1 1 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3' Cl1' O4' 109.43(17) . . ?
O3' Cl1' O5' 108.91(16) . . ?
O4' Cl1' O5' 109.93(17) . . ?
O3' Cl1' O2' 110.82(17) . . ?
O4' Cl1' O2' 108.64(18) . . ?
O5' Cl1' O2' 109.10(17) . . ?
O3 Cl1 O2 110.68(17) . . ?
O3 Cl1 O4 109.58(18) . . ?
O2 Cl1 O4 109.15(18) . . ?
O3 Cl1 O5 108.97(17) . . ?
O2 Cl1 O5 108.71(18) . . ?
O4 Cl1 O5 109.72(19) . . ?
C2 N1 C6 126.3(3) . . ?
C8 N9 C4 109.1(3) . . ?
C8 N9 C9 126.1(3) . . ?
C4 N9 C9 124.8(3) . . ?
C2' N1' C6' 126.2(3) . . ?
C2 N3 C4 112.4(3) . . ?
C8 N7 C5 108.7(3) . . ?
C2' N3' C4' 112.0(3) . . ?
C8' N9' C4' 108.3(3) . . ?
C8' N9' C9' 127.6(3) . . ?
C4' N9' C9' 124.1(3) . . ?
N3 C4 N9 126.5(3) . . ?
N3 C4 C5 127.7(3) . . ?
N9 C4 C5 105.8(3) . . ?
C11 C10 C9 176.9(4) . . ?
N7 C8 N9 108.6(3) . . ?
C8' N7' C5' 108.4(3) . . ?
N7' C5' C4' 106.8(3) . . ?
N7' C5' C6' 132.4(3) . . ?
C4' C5' C6' 120.7(3) . . ?
N2' C2' N3' 119.8(3) . . ?
N2' C2' N1' 116.3(3) . . ?
N3' C2' N1' 123.9(3) . . ?
C10' C9' N9' 110.8(3) . . ?
N3' C4' N9' 125.5(3) . . ?
N3' C4' C5' 127.3(3) . . ?
N9' C4' C5' 107.2(3) . . ?
O1 C6 N1 120.9(3) . . ?
O1 C6 C5 129.1(3) . . ?
N1 C6 C5 110.0(3) . . ?
C10 C9 N9 110.8(3) . . ?
N7' C8' N9' 109.3(3) . . ?
C11' C10' C9' 177.0(4) . . ?
N7 C5 C4 107.9(3) . . ?
N7 C5 C6 132.0(3) . . ?
C4 C5 C6 120.0(3) . . ?
O1' C6' N1' 121.6(3) . . ?
O1' C6' C5' 128.6(3) . . ?
N1' C6' C5' 109.7(3) . . ?
N3 C2 N2 119.8(3) . . ?
N3 C2 N1 123.6(3) . . ?
N2 C2 N1 116.6(3) . . ?
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
Cl1' O3' 1.433(3) . ?
Cl1' O4' 1.438(3) . ?
Cl1' O5' 1.439(3) . ?
Cl1' O2' 1.440(3) . ?
Cl1 O3 1.431(3) . ?
Cl1 O2 1.434(3) . ?
Cl1 O4 1.440(3) . ?
Cl1 O5 1.449(3) . ?
O1 C6 1.240(4) . ?
O1' C6' 1.238(4) . ?
N1 C2 1.366(5) . ?
N1 C6 1.392(4) . ?
N2' C2' 1.325(5) . ?
N9 C8 1.357(4) . ?
N9 C4 1.368(4) . ?
N9 C9 1.481(4) . ?
N1' C2' 1.369(5) . ?
N1' C6' 1.408(5) . ?
N2 C2 1.329(5) . ?
N3 C2 1.323(4) . ?
N3 C4 1.342(4) . ?
N7 C8 1.327(4) . ?
N7 C5 1.367(4) . ?
N3' C2' 1.325(4) . ?
N3' C4' 1.359(4) . ?
N9' C8' 1.358(5) . ?
N9' C4' 1.363(4) . ?
N9' C9' 1.474(5) . ?
C4 C5 1.388(5) . ?
C10 C11 1.182(6) . ?
C10 C9 1.459(5) . ?
N7' C8' 1.332(5) . ?
N7' C5' 1.382(5) . ?
C5' C4' 1.392(5) . ?
C5' C6' 1.412(5) . ?
C11' C10' 1.194(5) . ?
C9' C10' 1.465(5) . ?
C6 C5 1.419(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181685
