#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006094.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006094
loop_
_publ_author_name
'Sood, G.'
'Schwalbe, C. H.'
'Fraser, W.'
_publ_section_title
;
 2,6-Diazido-9-(carboxymethyl)purine Methyl Ester
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              608
_journal_page_last               610
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C8 H6 N10 O2'
_chemical_formula_weight         274.23
_chemical_melting_point          400.0(10)
_chemical_name_systematic
;
N-9-(Carboxymethyl)-2,6-diazidopurine methyl ester
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 102.907(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.761(2)
_cell_length_b                   12.1276(13)
_cell_length_c                   7.9969(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      44.3
_cell_measurement_theta_min      22.2
_cell_volume                     1206.3(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
;
DATREDXL (Brookhaven National Laboratory & University of Birmingham, 1986)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'MULTAN84 (Main, Germain & Woolfson, 1984)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4316
_diffrn_reflns_theta_max         67.7
_diffrn_reflns_theta_min         3.55
_diffrn_standards_decay_%        19
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow--brown'
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    none
_exptl_crystal_description       lath
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.036
_refine_ls_goodness_of_fit_obs   1.119
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_restrained_S_obs      1.119
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_obs          0.0629
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0999P)^2^+0.0504P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1961
_refine_ls_wR_factor_obs         0.1646
_reflns_number_observed          1384
_reflns_number_total             2173
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    bm1122.cif
_[local]_cod_data_source_block   gs42free
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '399-401 K' was changed to
'400.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2006094
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.095(2) 0.0731(15) 0.0659(14) -0.0039(13) 0.0219(14) 0.0007(11)
C2 0.100(2) 0.0631(15) 0.0549(15) -0.0020(15) 0.025(2) 0.0011(11)
N3 0.105(2) 0.0550(11) 0.0539(12) -0.0005(12) 0.0191(13) -0.0007(9)
C4 0.095(2) 0.0615(14) 0.0533(14) -0.0028(14) 0.027(2) -0.0020(11)
C5 0.099(2) 0.0611(15) 0.072(2) -0.0053(15) 0.035(2) -0.0019(13)
C6 0.094(2) 0.077(2) 0.069(2) -0.016(2) 0.027(2) -0.0064(14)
N7 0.111(2) 0.0610(14) 0.089(2) -0.0083(14) 0.033(2) -0.0061(12)
C8 0.114(3) 0.055(2) 0.083(2) 0.006(2) 0.037(2) 0.0015(14)
N9 0.096(2) 0.0564(11) 0.0581(12) 0.0017(12) 0.0241(13) 0.0004(9)
C10 0.104(2) 0.0629(15) 0.0500(13) 0.006(2) 0.0178(15) 0.0008(11)
C11 0.103(2) 0.0521(13) 0.0518(15) 0.0043(14) 0.0166(15) 0.0012(10)
O12 0.127(2) 0.0912(14) 0.0529(11) -0.0210(13) 0.0261(12) -0.0093(9)
O13 0.107(2) 0.0982(15) 0.0619(12) -0.0047(13) 0.0107(13) 0.0081(10)
C14 0.107(3) 0.104(3) 0.106(3) -0.009(2) 0.021(3) 0.011(2)
N21 0.112(2) 0.0704(14) 0.0652(15) 0.0126(15) 0.015(2) 0.0072(11)
N22 0.127(3) 0.075(2) 0.101(2) 0.014(2) 0.019(2) 0.006(2)
N23 0.160(4) 0.111(3) 0.184(5) 0.040(3) 0.000(4) 0.009(3)
N61 0.097(2) 0.095(2) 0.109(2) -0.015(2) 0.010(2) -0.001(2)
N62 0.113(3) 0.125(3) 0.111(3) -0.031(3) 0.004(2) -0.011(2)
N63 0.145(4) 0.186(5) 0.152(4) -0.025(4) -0.027(4) 0.006(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
N1 0.2173(2) 0.4368(2) 0.0400(3) 0.0773(7) Uani d 1 N
C2 0.2953(3) 0.4986(2) 0.1369(3) 0.0716(8) Uani d 1 C
N3 0.3854(2) 0.4657(2) 0.2385(3) 0.0711(7) Uani d 1 N
C4 0.3934(3) 0.3562(2) 0.2419(3) 0.0684(8) Uani d 1 C
C5 0.3212(3) 0.2814(2) 0.1512(4) 0.0750(8) Uani d 1 C
C6 0.2297(3) 0.3284(3) 0.0457(4) 0.0785(9) Uani d 1 C
N7 0.3556(3) 0.1746(2) 0.1886(4) 0.0856(8) Uani d 1 N
C8 0.4468(4) 0.1869(2) 0.2993(5) 0.0815(10) Uani d 1 C
H81 0.489(3) 0.136(3) 0.344(4) 0.084(10) Uiso d 1 H
N9 0.4750(2) 0.2946(2) 0.3370(3) 0.0692(7) Uani d 1 N
C10 0.5693(3) 0.3367(2) 0.4522(3) 0.0723(8) Uani d 1 C
H101 0.608(3) 0.276(3) 0.530(4) 0.095(10) Uiso d 1 H
H102 0.551(2) 0.396(2) 0.515(4) 0.066(7) Uiso d 1 H
C11 0.6500(3) 0.3806(2) 0.3602(3) 0.0690(8) Uani d 1 C
O12 0.6391(2) 0.3854(2) 0.2071(2) 0.0896(7) Uani d 1 O
O13 0.7366(2) 0.4130(2) 0.4727(3) 0.0901(7) Uani d 1 O
C14 0.8224(4) 0.4658(4) 0.4117(6) 0.1060(13) Uani d 1 C
H141 0.864(3) 0.416(4) 0.368(5) 0.109(14) Uiso d 1 H
H142 0.879(4) 0.506(4) 0.546(7) 0.147(15) Uiso d 1 H
H143 0.803(4) 0.530(4) 0.321(7) 0.153(17) Uiso d 1 H
N21 0.2811(3) 0.6133(2) 0.1319(3) 0.0834(8) Uani d 1 N
N22 0.1975(3) 0.6439(3) 0.0376(5) 0.1023(10) Uani d 1 N
N23 0.1247(4) 0.6822(4) -0.0488(8) 0.158(2) Uani d 1 N
N61 0.1538(3) 0.2599(3) -0.0553(5) 0.1024(10) Uani d 1 N
N62 0.0804(4) 0.3138(3) -0.1502(6) 0.1197(12) Uani d 1 N
N63 0.0109(4) 0.3546(5) -0.2393(8) 0.171(2) Uani d 1 N
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_publ_flag
C6 N1 C2 117.8(3) ?
N3 C2 N1 128.4(3) yes
N3 C2 N21 114.1(3) yes
N1 C2 N21 117.5(3) yes
C2 N3 C4 111.6(3) ?
N3 C4 N9 127.0(3) ?
N3 C4 C5 127.3(3) ?
N9 C4 C5 105.7(2) ?
C4 C5 N7 111.1(3) ?
C4 C5 C6 114.8(3) ?
N7 C5 C6 134.1(3) ?
N1 C6 N61 120.8(3) yes
N1 C6 C5 120.1(3) yes
N61 C6 C5 119.1(3) yes
C8 N7 C5 103.5(3) ?
N7 C8 N9 114.1(3) ?
C4 N9 C8 105.6(3) ?
C4 N9 C10 126.0(2) ?
C8 N9 C10 128.4(3) ?
N9 C10 C11 112.5(2) ?
O12 C11 O13 124.6(3) ?
O12 C11 C10 125.7(3) ?
O13 C11 C10 109.6(2) ?
C11 O13 C14 119.0(3) ?
N22 N21 C2 114.2(3) ?
N23 N22 N21 173.2(4) ?
N62 N61 C6 111.8(3) ?
N63 N62 N61 174.7(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 1.324(4) yes
N1 C2 1.345(4) yes
C2 N3 1.313(4) yes
C2 N21 1.402(4) yes
N3 C4 1.331(3) yes
C4 N9 1.367(4) yes
C4 C5 1.379(4) yes
C5 N7 1.379(4) yes
C5 C6 1.400(5) yes
C6 N61 1.389(4) yes
N7 C8 1.304(5) yes
C8 N9 1.371(4) yes
N9 C10 1.436(4) yes
C10 C11 1.490(4) yes
C11 O12 1.203(3) yes
C11 O13 1.319(4) yes
O13 C14 1.444(5) yes
N21 N22 1.219(5) yes
N22 N23 1.127(5) yes
N61 N62 1.250(5) yes
N62 N63 1.121(6) yes
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_publ_flag
C6 N1 C2 N3 0.7(4) ?
C6 N1 C2 N21 -179.2(2) ?
N1 C2 N3 C4 -1.6(4) ?
N21 C2 N3 C4 178.3(2) ?
C2 N3 C4 N9 -178.3(2) ?
C2 N3 C4 C5 1.5(3) ?
N3 C4 C5 N7 -179.3(2) ?
N9 C4 C5 N7 0.5(3) ?
N3 C4 C5 C6 -0.5(4) ?
N9 C4 C5 C6 179.3(2) ?
C2 N1 C6 N61 -178.0(2) ?
C2 N1 C6 C5 0.5(4) ?
C4 C5 C6 N1 -0.6(4) ?
N7 C5 C6 N1 177.9(3) ?
C4 C5 C6 N61 177.9(2) ?
N7 C5 C6 N61 -3.6(5) ?
C4 C5 N7 C8 -0.2(3) ?
C6 C5 N7 C8 -178.7(3) ?
C5 N7 C8 N9 -0.2(3) ?
N3 C4 N9 C8 179.2(2) ?
C5 C4 N9 C8 -0.5(2) ?
N3 C4 N9 C10 -0.4(4) ?
C5 C4 N9 C10 179.8(2) ?
N7 C8 N9 C4 0.5(3) ?
N7 C8 N9 C10 -179.9(2) ?
C4 N9 C10 C11 -76.8(3) yes
C8 N9 C10 C11 103.6(3) yes
N9 C10 C11 O12 2.5(4) ?
N9 C10 C11 O13 -177.0(2) ?
O12 C11 O13 C14 4.9(5) ?
C10 C11 O13 C14 -175.7(3) ?
N3 C2 N21 N22 180.0(3) ?
N1 C2 N21 N22 -0.1(4) yes
C2 N21 N22 N23 -163.(4) ?
N1 C6 N61 N62 2.8(5) yes
C5 C6 N61 N62 -175.7(3) ?
C6 N61 N62 N63 -176.(6) ?