#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/79/2007906.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_2007906
loop_
_publ_author_name
'Sood, Geeta'
'Schwalbe, Carl H.'
'Fraser, William'
_publ_section_title
;
 9-(Carboxymethyl)-6-chloropurine Ethyl Ester
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1907
_journal_page_last               1909
_journal_paper_doi               10.1107/S0108270198012360
_journal_volume                  54
_journal_year                    1998
_chemical_formula_analytical     'C9 H9 Cl N4 O2'
_chemical_formula_structural     'C9 H9 Cl N4 O2'
_chemical_formula_sum            'C9 H9 Cl N4 O2'
_chemical_formula_weight         240.65
_chemical_melting_point          .367E-305
_chemical_name_common
;
 Methyl 6-Chloro-9-purine-9-acetate
;
_chemical_name_systematic
;
ethyl 6-chloropurine-9-acetate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                105.01(2)
_cell_angle_beta                 93.85(2)
_cell_angle_gamma                105.00(2)
_cell_formula_units_Z            4
_cell_length_a                   5.872(2)
_cell_length_b                   10.529(2)
_cell_length_c                   19.096(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.2
_cell_measurement_theta_min      19.7
_cell_volume                     1090.0(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CADABS (Gould & Smith, 1986)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'MULTAN84 (Main et al., 1984)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.077
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3890
_diffrn_reflns_theta_max         67.92
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        9
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.066
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_correction_T_min  0.473
_exptl_absorpt_correction_type
;
empirical via \y scans (North et al., 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.627
_refine_ls_extinction_coef       0.0075(16)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.099
_refine_ls_goodness_of_fit_obs   1.148
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_restrained_S_obs      1.148
_refine_ls_R_factor_all          0.087
_refine_ls_R_factor_obs          0.078
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1616P)²+0.5288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.234
_refine_ls_wR_factor_obs         0.226
_reflns_number_observed          3245
_reflns_number_total             3826
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            cf1279.cif
_cod_data_source_block           gsa5204
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.1616P)^2^+0.5288P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.1616P)^2^+0.5288P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1090.1(5)
_cod_database_code               2007906
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1A 0.2646(6) 0.2583(3) 1.0160(2) 0.0576(8) Uani d . 1 . N
C2A 0.4904(7) 0.3408(4) 1.0356(2) 0.0540(9) Uani d . 1 . C
H2A 0.5462(7) 0.3715(4) 1.0856(2) 0.065 Uiso calc R 1 . H
N3A 0.6428(5) 0.3834(3) 0.99248(14) 0.0482(7) Uani d . 1 . N
C4A 0.5485(6) 0.3363(3) 0.9223(2) 0.0426(7) Uani d . 1 . C
C5A 0.3162(6) 0.2497(3) 0.8940(2) 0.0454(7) Uani d . 1 . C
C6A 0.1814(6) 0.2138(4) 0.9461(2) 0.0495(8) Uani d . 1 . C
Cl6A -0.1066(2) 0.10674(11) 0.91953(6) 0.0722(4) Uani d . 1 . Cl
N7A 0.2782(5) 0.2209(3) 0.8186(2) 0.0531(7) Uani d . 1 . N
C8A 0.4811(6) 0.2878(4) 0.8034(2) 0.0520(8) Uani d . 1 . C
H8A 0.5074(6) 0.2875(4) 0.7559(2) 0.062 Uiso calc R 1 . H
N9A 0.6510(5) 0.3581(3) 0.86309(14) 0.0459(7) Uani d . 1 . N
C10A 0.8861(6) 0.4484(4) 0.8642(2) 0.0467(8) Uani d . 1 . C
H101 0.9788(6) 0.3960(4) 0.8354(2) 0.056 Uiso calc R 1 . H
H102 0.9676(6) 0.4853(4) 0.9142(2) 0.056 Uiso calc R 1 . H
C11A 0.8704(6) 0.5646(4) 0.8338(2) 0.0488(8) Uani d . 1 . C
O12A 0.6927(5) 0.5789(3) 0.8073(2) 0.0640(7) Uani d . 1 . O
O13A 1.0868(5) 0.6505(3) 0.8418(2) 0.0659(8) Uani d . 1 . O
C14A 1.1030(10) 0.7750(5) 0.8187(3) 0.087(2) Uani d . 1 . C
H141 1.0977(10) 0.7541(5) 0.7660(3) 0.105 Uiso calc R 1 . H
H142 0.9704(10) 0.8106(5) 0.8322(3) 0.105 Uiso calc R 1 . H
C15A 1.3270(11) 0.8760(6) 0.8552(4) 0.102(2) Uani d . 1 . C
H151 1.353(5) 0.953(3) 0.836(2) 0.152 Uiso calc R 1 . H
H152 1.4552(15) 0.8353(17) 0.847(2) 0.152 Uiso calc R 1 . H
H153 1.321(4) 0.906(4) 0.9068(5) 0.152 Uiso calc R 1 . H
N1B 0.7461(5) 0.2544(3) 0.5159(2) 0.0571(8) Uani d . 1 . N
C2B 0.5375(7) 0.1907(4) 0.5343(2) 0.0541(9) Uani d . 1 . C
H2B 0.5282(7) 0.2097(4) 0.5842(2) 0.065 Uiso calc R 1 . H
N3B 0.3443(5) 0.1046(3) 0.49027(15) 0.0484(7) Uani d . 1 . N
C4B 0.3749(6) 0.0819(3) 0.4204(2) 0.0448(7) Uani d . 1 . C
C5B 0.5787(7) 0.1397(4) 0.3931(2) 0.0505(8) Uani d . 1 . C
C6B 0.7646(6) 0.2283(4) 0.4458(2) 0.0532(8) Uani d . 1 . C
Cl6B 1.0279(2) 0.31052(13) 0.42132(7) 0.0796(4) Uani d . 1 . Cl
N7B 0.5456(7) 0.0948(4) 0.3176(2) 0.0670(9) Uani d . 1 . N
C8B 0.3294(8) 0.0130(4) 0.3009(2) 0.0658(11) Uani d . 1 . C
H8B 0.2584(8) -0.0331(4) 0.2528(2) 0.079 Uiso calc R 1 . H
N9B 0.2145(5) 0.0006(3) 0.36030(15) 0.0521(7) Uani d . 1 . N
C10B -0.0174(6) -0.0901(4) 0.3608(2) 0.0513(8) Uani d . 1 . C
H103 -0.1362(6) -0.0747(4) 0.3287(2) 0.062 Uiso calc R 1 . H
H104 -0.0589(6) -0.0692(4) 0.4100(2) 0.062 Uiso calc R 1 . H
C11B -0.0199(6) -0.2379(3) 0.3360(2) 0.0450(7) Uani d . 1 . C
O12B 0.1333(5) -0.2802(3) 0.30807(14) 0.0573(7) Uani d . 1 . O
O13B -0.2193(4) -0.3158(2) 0.34962(13) 0.0520(6) Uani d . 1 . O
C14B -0.2477(7) -0.4628(4) 0.3312(2) 0.0632(10) Uani d . 1 . C
H143 -0.1054(7) -0.4798(4) 0.3508(2) 0.076 Uiso calc R 1 . H
H144 -0.2753(7) -0.5027(4) 0.2784(2) 0.076 Uiso calc R 1 . H
C15B -0.4562(9) -0.5241(5) 0.3642(3) 0.0787(13) Uani d . 1 . C
H154 -0.494(4) -0.6223(5) 0.3477(17) 0.118 Uiso calc R 1 . H
H155 -0.591(2) -0.496(3) 0.3497(18) 0.118 Uiso calc R 1 . H
H156 -0.418(3) -0.494(3) 0.4167(3) 0.118 Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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
C6A N1A C2A 117.3(3) n
N3A C2A N1A 128.0(3) yes
C4A N3A C2A 112.2(3) n
N3A C4A N9A 128.5(3) ?
N3A C4A C5A 125.9(3) n
N9A C4A C5A 105.6(3) yes
C6A C5A N7A 135.0(3) ?
C6A C5A C4A 114.6(3) n
N7A C5A C4A 110.3(3) yes
N1A C6A C5A 122.0(3) n
N1A C6A Cl6A 118.1(3) ?
C5A C6A Cl6A 119.9(3) ?
C8A N7A C5A 103.5(3) yes
N7A C8A N9A 114.6(3) yes
C4A N9A C8A 106.0(3) yes
C4A N9A C10A 126.5(3) ?
C8A N9A C10A 127.2(3) ?
N9A C10A C11A 111.4(3) ?
O12A C11A O13A 125.0(3) ?
O12A C11A C10A 125.8(3) ?
O13A C11A C10A 109.2(3) ?
C11A O13A C14A 116.5(3) ?
C15A C14A O13A 108.0(4) ?
C6B N1B C2B 117.1(3) n
N3B C2B N1B 128.2(3) yes
C4B N3B C2B 111.7(3) n
N3B C4B N9B 127.8(3) ?
N3B C4B C5B 126.6(3) n
N9B C4B C5B 105.6(3) yes
N7B C5B C6B 134.3(3) ?
N7B C5B C4B 110.7(3) n
C6B C5B C4B 115.0(3) yes
N1B C6B C5B 121.4(3) n
N1B C6B Cl6B 117.7(3) ?
C5B C6B Cl6B 120.9(3) ?
C8B N7B C5B 103.8(3) yes
N7B C8B N9B 114.3(3) yes
C4B N9B C8B 105.5(3) yes
C4B N9B C10B 126.2(3) ?
C8B N9B C10B 128.0(3) ?
N9B C10B C11B 111.4(3) ?
O12B C11B O13B 124.9(3) ?
O12B C11B C10B 125.7(3) ?
O13B C11B C10B 109.4(3) ?
C11B O13B C14B 116.8(3) ?
O13B C14B C15B 107.0(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1A C6A . 1.308(5) n
N1A C2A . 1.349(5) n
C2A N3A . 1.329(5) n
N3A C4A . 1.328(4) n
C4A N9A . 1.359(4) n
C4A C5A . 1.409(4) n
C5A C6A . 1.380(5) n
C5A N7A . 1.381(4) n
C6A Cl6A . 1.729(4) n
N7A C8A . 1.311(5) yes
C8A N9A . 1.367(4) yes
N9A C10A . 1.455(4) n
C10A C11A . 1.505(5) ?
C11A O12A . 1.190(4) ?
C11A O13A . 1.328(4) ?
O13A C14A . 1.470(5) ?
C14A C15A . 1.454(7) ?
N1B C6B . 1.313(5) n
N1B C2B . 1.353(5) n
C2B N3B . 1.327(5) n
N3B C4B . 1.326(4) n
C4B N9B . 1.366(4) n
C4B C5B . 1.394(5) n
C5B N7B . 1.380(5) n
C5B C6B . 1.383(5) n
C6B Cl6B . 1.724(4) n
N7B C8B . 1.301(6) yes
C8B N9B . 1.377(5) yes
N9B C10B . 1.449(4) n
C10B C11B . 1.501(5) ?
C11B O12B . 1.200(4) ?
C11B O13B . 1.329(4) ?
O13B C14B . 1.458(5) ?
C14B C15B . 1.490(6) ?
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
C6A N1A C2A N3A -0.1(6) ?
N1A C2A N3A C4A 0.7(6) ?
C2A N3A C4A N9A -179.8(3) ?
C2A N3A C4A C5A -0.7(5) ?
N3A C4A C5A C6A 0.2(5) ?
N9A C4A C5A C6A 179.5(3) ?
N3A C4A C5A N7A -180.0(3) ?
N9A C4A C5A N7A -0.7(4) ?
C2A N1A C6A C5A -0.5(6) ?
C2A N1A C6A Cl6A 179.4(3) ?
N7A C5A C6A N1A -179.4(4) ?
C4A C5A C6A N1A 0.4(5) ?
N7A C5A C6A Cl6A 0.8(6) ?
C4A C5A C6A Cl6A -179.4(2) ?
C6A C5A N7A C8A -180.0(4) ?
C4A C5A N7A C8A 0.2(4) ?
C5A N7A C8A N9A 0.3(4) ?
N3A C4A N9A C8A -179.9(3) ?
C5A C4A N9A C8A 0.8(4) ?
N3A C4A N9A C10A -5.0(6) ?
C5A C4A N9A C10A 175.7(3) ?
N7A C8A N9A C4A -0.8(4) ?
N7A C8A N9A C10A -175.6(3) ?
C4A N9A C10A C11A -115.7(4) ?
C8A N9A C10A C11A 58.2(5) yes
N9A C10A C11A O12A -4.8(5) ?
N9A C10A C11A O13A 174.6(3) yes
O12A C11A O13A C14A 2.7(6) ?
C10A C11A O13A C14A -176.6(4) yes
C11A O13A C14A C15A 159.4(5) yes
C6B N1B C2B N3B -0.7(6) ?
N1B C2B N3B C4B 1.0(6) ?
C2B N3B C4B N9B -179.3(3) ?
C2B N3B C4B C5B -0.8(5) ?
N3B C4B C5B N7B -178.9(3) ?
N9B C4B C5B N7B -0.2(4) ?
N3B C4B C5B C6B 0.4(5) ?
N9B C4B C5B C6B 179.2(3) ?
C2B N1B C6B C5B 0.1(6) ?
C2B N1B C6B Cl6B 179.1(3) ?
N7B C5B C6B N1B 179.1(4) ?
C4B C5B C6B N1B 0.0(5) ?
N7B C5B C6B Cl6B 0.1(6) ?
C4B C5B C6B Cl6B -179.0(3) ?
C6B C5B N7B C8B -179.2(4) ?
C4B C5B N7B C8B -0.1(5) ?
C5B N7B C8B N9B 0.3(5) ?
N3B C4B N9B C8B 179.1(4) ?
C5B C4B N9B C8B 0.3(4) ?
N3B C4B N9B C10B -6.9(6) ?
C5B C4B N9B C10B 174.4(3) ?
N7B C8B N9B C4B -0.4(5) ?
N7B C8B N9B C10B -174.3(4) ?
C4B N9B C10B C11B -107.7(4) ?
C8B N9B C10B C11B 65.1(5) yes
N9B C10B C11B O12B -11.2(5) ?
N9B C10B C11B O13B 168.9(3) yes
O12B C11B O13B C14B 2.1(5) ?
C10B C11B O13B C14B -177.9(3) yes
C11B O13B C14B C15B 169.1(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 203956
