#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:52:57 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180159 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/55/7105526.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_7105526
loop_
_publ_author_name
'Prajapati, Rajneesh Kumar'
'Kumar, Jitendra'
'Verma, Sandeep'
_publ_section_title
;
 Silver-catalyzed intramolecular cyclization of 9-propargyladenine via
 N3 alkylation
;
_journal_issue                   19
_journal_name_full               'Chemical Communications'
_journal_page_first              3312
_journal_page_last               3314
_journal_paper_doi               10.1039/c001947j
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C8 H8 N6 O3'
_chemical_formula_weight         236.20
_chemical_name_systematic
;
?
;
_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                93.040(10)
_cell_angle_beta                 97.088(10)
_cell_angle_gamma                101.559(10)
_cell_formula_units_Z            2
_cell_length_a                   5.536(3)
_cell_length_b                   6.938(4)
_cell_length_c                   12.729(7)
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3.01
_cell_volume                     473.8(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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2428
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.09(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0751
_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)+(0.1216P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1776
_refine_ls_wR_factor_ref         0.1971
_reflns_number_gt                1242
_reflns_number_total             1643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c001947j.txt
_cod_data_source_block           complex2
_cod_database_code               7105526
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
C2 C 0.2488(6) 0.6062(4) 1.1201(2) 0.0217(7) Uani 1 1 d . . .
H2 H 0.0918 0.5272 1.1200 0.026 Uiso 1 1 calc R . .
C4 C 0.6161(6) 0.7792(4) 1.2102(2) 0.0191(7) Uani 1 1 d . . .
C5 C 0.7066(6) 0.8354(4) 1.1186(2) 0.0196(7) Uani 1 1 d . . .
C6 C 0.5500(6) 0.7679(4) 1.0228(2) 0.0201(7) Uani 1 1 d . . .
C8 C 0.9811(5) 0.9615(4) 1.2497(2) 0.0227(7) Uani 1 1 d . . .
H8 H 1.1264 1.0319 1.2902 0.027 Uiso 1 1 calc R . .
C9 C 0.7439(6) 0.8234(5) 1.4036(2) 0.0241(8) Uani 1 1 d . . .
H9A H 0.7582 0.9492 1.4435 0.029 Uiso 1 1 calc R . .
H9B H 0.8679 0.7573 1.4373 0.029 Uiso 1 1 calc R . .
C10 C 0.4902(6) 0.7000(5) 1.4029(2) 0.0246(8) Uani 1 1 d . . .
H10 H 0.4414 0.6724 1.4688 0.029 Uiso 1 1 calc R . .
C11 C 0.3290(6) 0.6265(4) 1.3196(2) 0.0230(7) Uani 1 1 d . . .
H11 H 0.1758 0.5490 1.3278 0.028 Uiso 1 1 calc R . .
N1 N 0.3176(4) 0.6515(4) 1.02781(17) 0.0200(7) Uani 1 1 d . . .
N2 N 0.2868(5) 0.7006(4) 0.67436(18) 0.0218(6) Uani 1 1 d . . .
N3 N 0.3895(4) 0.6659(4) 1.21504(17) 0.0194(6) Uani 1 1 d . . .
N6 N 0.6094(5) 0.8090(3) 0.92779(17) 0.0212(7) Uani 1 1 d . . .
H6A H 0.5053 0.7639 0.8719 0.025 Uiso 1 1 calc R . .
H6B H 0.7522 0.8808 0.9219 0.025 Uiso 1 1 calc R . .
N7 N 0.9422(4) 0.9535(4) 1.14518(18) 0.0220(7) Uani 1 1 d . . .
N9 N 0.7862(4) 0.8558(4) 1.29283(18) 0.0198(6) Uani 1 1 d . . .
O1 O 0.2455(4) 0.6113(3) 0.75672(15) 0.0267(6) Uani 1 1 d . . .
O2 O 0.1272(4) 0.6686(3) 0.59475(15) 0.0305(7) Uani 1 1 d . . .
O3 O 0.4873(4) 0.8193(3) 0.67478(16) 0.0290(6) Uani 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'
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
N1 C2 N3 124.8(3) . . ?
N9 C4 N3 125.9(3) . . ?
N9 C4 C5 109.0(3) . . ?
N3 C4 C5 125.1(3) . . ?
C4 C5 N7 108.5(3) . . ?
C4 C5 C6 116.8(3) . . ?
N7 C5 C6 134.7(3) . . ?
N6 C6 N1 117.7(3) . . ?
N6 C6 C5 124.2(3) . . ?
N1 C6 C5 118.1(2) . . ?
N7 C8 N9 113.3(3) . . ?
N9 C9 C10 108.9(2) . . ?
C11 C10 C9 126.9(3) . . ?
C10 C11 N3 119.8(3) . . ?
C2 N1 C6 120.3(2) . . ?
O2 N2 O3 120.9(2) . . ?
O2 N2 O1 119.7(2) . . ?
O3 N2 O1 119.4(2) . . ?
C2 N3 C4 115.0(2) . . ?
C2 N3 C11 128.7(3) . . ?
C4 N3 C11 116.3(2) . . ?
C8 N7 C5 104.1(2) . . ?
C4 N9 C8 105.1(2) . . ?
C4 N9 C9 122.2(2) . . ?
C8 N9 C9 132.7(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
C2 N1 1.314(3) . ?
C2 N3 1.351(4) . ?
C4 N9 1.330(4) . ?
C4 N3 1.351(4) . ?
C4 C5 1.371(4) . ?
C5 N7 1.386(4) . ?
C5 C6 1.404(4) . ?
C6 N6 1.323(3) . ?
C6 N1 1.386(4) . ?
C8 N7 1.318(4) . ?
C8 N9 1.369(4) . ?
C9 N9 1.479(3) . ?
C9 C10 1.490(4) . ?
C10 C11 1.307(4) . ?
C11 N3 1.439(3) . ?
N2 O2 1.238(3) . ?
N2 O3 1.241(3) . ?
N2 O1 1.268(3) . ?
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
N9 C4 C5 N7 -0.6(4) . . . . ?
N3 C4 C5 N7 178.8(3) . . . . ?
N9 C4 C5 C6 -179.8(2) . . . . ?
N3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 N6 180.0(3) . . . . ?
N7 C5 C6 N6 1.0(6) . . . . ?
C4 C5 C6 N1 0.3(4) . . . . ?
N7 C5 C6 N1 -178.7(3) . . . . ?
N9 C9 C10 C11 1.4(5) . . . . ?
C9 C10 C11 N3 -1.1(5) . . . . ?
N3 C2 N1 C6 0.3(5) . . . . ?
N6 C6 N1 C2 -180.0(3) . . . . ?
C5 C6 N1 C2 -0.3(4) . . . . ?
N1 C2 N3 C4 -0.4(5) . . . . ?
N1 C2 N3 C11 179.0(3) . . . . ?
N9 C4 N3 C2 179.7(3) . . . . ?
C5 C4 N3 C2 0.4(5) . . . . ?
N9 C4 N3 C11 0.2(5) . . . . ?
C5 C4 N3 C11 -179.0(3) . . . . ?
C10 C11 N3 C2 -179.1(3) . . . . ?
C10 C11 N3 C4 0.2(4) . . . . ?
N9 C8 N7 C5 0.2(3) . . . . ?
C4 C5 N7 C8 0.2(3) . . . . ?
C6 C5 N7 C8 179.3(3) . . . . ?
N3 C4 N9 C8 -178.8(3) . . . . ?
C5 C4 N9 C8 0.6(3) . . . . ?
N3 C4 N9 C9 0.1(5) . . . . ?
C5 C4 N9 C9 179.5(3) . . . . ?
N7 C8 N9 C4 -0.5(4) . . . . ?
N7 C8 N9 C9 -179.2(3) . . . . ?
C10 C9 N9 C4 -0.8(4) . . . . ?
C10 C9 N9 C8 177.7(3) . . . . ?
