#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/41/2004107.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_2004107
loop_
_publ_author_name
'Chan, D. M. C.'
'Schwalbe, C. H.'
'Sood, G.'
'Fraser, W.'
_publ_section_title
;
 9-(Carboxymethyl)-2,6-dichloropurine Ethyl Ester. An Intermediate for
 Peptidic Nucleic Acid Synthesis
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2383
_journal_page_last               2386
_journal_paper_doi               10.1107/S0108270195008705
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C9 H8 Cl2 N4 O2'
_chemical_formula_weight         275.09
_chemical_melting_point          394.1(10)
_chemical_name_systematic
;
 9-(carboxymethyl)-2,6-dichloropurine ethyl ester
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 104.03(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.5850(14)
_cell_length_b                   11.841(2)
_cell_length_c                   8.012(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.2
_cell_measurement_theta_min      9.7
_cell_volume                     2354.8(10)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
;
DATREDXL (Brookhaven National Laboratory & Univ. of Birmingham, 1986)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'MULTAN80 (Main et al., 1980)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2524
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'very pale yellow'
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       tabular
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.207
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.015
_refine_ls_goodness_of_fit_obs   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_restrained_S_obs      1.048
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_obs          0.0353
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0583P)^2^ + 0.5523P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1064
_refine_ls_wR_factor_obs         0.0906
_reflns_number_observed          1462
_reflns_number_total             2055
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cf1024.cif
_cod_data_source_block           gita
_cod_depositor_comments
;
 Changing the _atom_site_occupancy data item value from '.' to '1'
 for all fully occupied atom sites.

 Antanas Vaitkus,
 2017-02-10

The following automatic conversions were performed:

'_chemical_melting_point' value '120-122_C' was changed to
'394.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
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_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2004107
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_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_type_symbol
N1 1 0.09837(8) 0.3243(2) 0.5420(3) 0.0461(5) Uani d N
C2 1 0.13531(10) 0.2584(2) 0.6414(3) 0.0420(6) Uani d C
Cl2 1 0.11702(3) 0.11776(6) 0.64249(10) 0.0571(2) Uani d Cl
N3 1 0.18326(8) 0.2842(2) 0.7380(3) 0.0402(5) Uani d N
C4 1 0.19291(9) 0.3944(2) 0.7313(3) 0.0377(5) Uani d C
C5 1 0.15866(10) 0.4748(2) 0.6351(3) 0.0417(6) Uani d C
C6 1 0.11059(10) 0.4330(2) 0.5391(3) 0.0443(6) Uani d C
Cl6 1 0.06350(3) 0.51922(8) 0.40991(10) 0.0688(3) Uani d Cl
N7 1 0.18100(9) 0.5814(2) 0.6631(3) 0.0505(6) Uani d N
C8 1 0.22708(11) 0.5640(2) 0.7722(4) 0.0475(6) Uani d C
N9 1 0.23691(8) 0.4528(2) 0.8188(3) 0.0399(5) Uani d N
C10 1 0.28615(10) 0.4061(2) 0.9266(3) 0.0420(6) Uani d C
C11 1 0.32372(10) 0.3645(2) 0.8221(3) 0.0401(6) Uani d C
O11 1 0.31164(7) 0.3516(2) 0.6690(2) 0.0543(5) Uani d O
O12 1 0.37172(7) 0.3472(2) 0.9250(2) 0.0483(5) Uani d O
C13 1 0.41401(12) 0.3045(4) 0.8490(5) 0.0610(8) Uani d C
C14 1 0.46559(14) 0.3184(5) 0.9798(8) 0.097(2) Uani d C
H1 1 0.2513(11) 0.6230(23) 0.8213(34) 0.044(7) . . H
H2 1 0.3047(11) 0.4641(23) 1.0065(37) 0.048(7) . . H
H3 1 0.2765(12) 0.3444(27) 0.9916(40) 0.062(9) . . H
H4 1 0.4130(14) 0.3554(30) 0.7429(46) 0.075(10) . . H
H5 1 0.4051(16) 0.2329(34) 0.8204(48) 0.088(13) . . H
H6 1 0.4922(18) 0.2793(34) 0.9262(48) 0.096(12) . . H
H7 1 0.4757(20) 0.4061(45) 0.9878(64) 0.129(18) . . H
H8 1 0.4658(22) 0.2937(53) 1.0848(65) 0.147(26) . . H
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C6 N1 C2 116.3(2) yes
N3 C2 N1 129.8(2) yes
N3 C2 Cl2 115.8(2) yes
N1 C2 Cl2 114.4(2) yes
C2 N3 C4 111.0(2) yes
N3 C4 N9 127.9(2) yes
N3 C4 C5 126.5(2) yes
N9 C4 C5 105.6(2) yes
C6 C5 N7 134.3(2) yes
C6 C5 C4 114.9(2) yes
N7 C5 C4 110.8(2) yes
N1 C6 C5 121.5(2) yes
N1 C6 Cl6 116.9(2) yes
C5 C6 Cl6 121.6(2) yes
C8 N7 C5 103.6(2) yes
N7 C8 N9 114.2(2) yes
C4 N9 C8 105.8(2) yes
C4 N9 C10 127.0(2) ?
C8 N9 C10 126.9(2) ?
N9 C10 C11 111.9(2) ?
O11 C11 O12 126.1(2) ?
O11 C11 C10 124.8(2) ?
O12 C11 C10 109.1(2) ?
C11 O12 C13 117.8(2) ?
O12 C13 C14 106.9(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 1.326(4) yes
N1 C2 1.331(3) yes
C2 N3 1.318(3) yes
C2 Cl2 1.730(3) yes
N3 C4 1.331(3) yes
C4 N9 1.361(3) yes
C4 C5 1.393(3) yes
C5 C6 1.375(4) yes
C5 N7 1.381(3) yes
C6 Cl6 1.721(2) yes
N7 C8 1.303(3) yes
C8 N9 1.376(3) yes
N9 C10 1.453(3) yes
C10 C11 1.502(4) yes
C11 O11 1.200(3) yes
C11 O12 1.319(3) yes
O12 C13 1.455(4) yes
C13 C14 1.482(5) 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 -0.8(4) ?
C6 N1 C2 Cl2 179.3(2) ?
N1 C2 N3 C4 1.5(4) ?
Cl2 C2 N3 C4 -178.6(2) ?
C2 N3 C4 N9 177.1(2) ?
C2 N3 C4 C5 -0.9(4) ?
N3 C4 C5 C6 -0.2(4) ?
N9 C4 C5 C6 -178.6(2) ?
N3 C4 C5 N7 178.2(2) ?
N9 C4 C5 N7 -0.2(3) ?
C2 N1 C6 C5 -0.6(4) ?
C2 N1 C6 Cl6 179.5(2) ?
N7 C5 C6 N1 -176.9(3) ?
C4 C5 C6 N1 1.0(4) ?
N7 C5 C6 Cl6 3.0(4) ?
C4 C5 C6 Cl6 -179.1(2) ?
C6 C5 N7 C8 178.0(3) ?
C4 C5 N7 C8 0.1(3) ?
C5 N7 C8 N9 0.0(3) ?
N3 C4 N9 C8 -178.1(3) ?
C5 C4 N9 C8 0.2(3) ?
N3 C4 N9 C10 6.9(4) ?
C5 C4 N9 C10 -174.7(2) ?
N7 C8 N9 C4 -0.2(3) ?
N7 C8 N9 C10 174.8(2) ?
C4 N9 C10 C11 81.0(3) yes
C8 N9 C10 C11 -92.9(3) yes
N9 C10 C11 O11 -12.8(4) ?
N9 C10 C11 O12 166.0(2) ?
O11 C11 O12 C13 -2.3(4) ?
C10 C11 O12 C13 178.9(3) ?
C11 O12 C13 C14 166.8(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21138689
