#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008153.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_2008153
loop_
_publ_author_name
'Helliwell, Madeleine'
'Dinsmore, Andrew'
'Garner, C. David'
'Joule, John A.'
_publ_contact_author
;
John A. Joule
Chemistry Department
The University of Manchester
Manchester M13 9PL
England
;
_publ_section_title
;
 A 1-alkylated pteridine, C~15~H~19~ClN~6~O~3~
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              254
_journal_page_last               256
_journal_paper_doi               10.1107/S0108270198011883
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C15 H19 Cl N6 O3'
_chemical_formula_weight         366.81
_chemical_name_systematic
;
6-chloro-2-(N,N-dimethylaminomethyleneamino)-1-(2,2-pivaloyloxymethyl)
pteridin-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.623(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7770(11)
_cell_length_b                   9.3742(5)
_cell_length_c                   17.0675(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.0
_cell_measurement_theta_min      14.4
_cell_volume                     1805.5(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1989)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296.2
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.047
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3883
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        79.45
_diffrn_reflns_theta_max         79.45
_diffrn_reflns_theta_min         4.07
_diffrn_standards_decay_%        1.73
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.122
_exptl_absorpt_correction_T_max  0.809
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type
;
\y scans (North et al., 1968)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_description       tabular
_exptl_crystal_F_000             768.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.114
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0489P)^2^+1.562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.167
_reflns_number_gt                2168
_reflns_number_total             3697
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd1002.cif
_cod_data_source_block           s660
_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^)+(0.0489P)^2^+1.562P] 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^)+(0.0489P)^2^+1.562P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2008153
_cod_database_fobs_code          2008153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.08434(9) 0.17990(13) 0.82344(7) 0.0867(4) Uani d . 1 . . Cl
O1 0.5163(2) 0.2705(3) 1.00055(16) 0.0700(8) Uani d . 1 . . O
O2 0.3302(2) -0.1383(3) 1.21625(14) 0.0597(7) Uani d . 1 . . O
O3 0.4398(3) -0.3008(3) 1.30057(17) 0.0764(8) Uani d . 1 . . O
N1 0.4063(2) -0.0556(3) 1.11305(16) 0.0494(7) Uani d . 1 . . N
N2 0.5475(2) 0.1248(3) 1.11056(16) 0.0495(7) Uani d . 1 . . N
N3 0.2870(2) 0.1705(3) 0.93634(16) 0.0519(7) Uani d . 1 . . N
N4 0.2243(3) -0.0702(3) 1.01207(18) 0.0600(8) Uani d . 1 . . N
N5 0.5766(2) -0.0386(3) 1.21891(16) 0.0519(7) Uani d . 1 . . N
N6 0.7560(2) -0.0240(3) 1.31793(17) 0.0567(8) Uani d . 1 . . N
C1 0.5131(3) 0.0151(4) 1.14651(19) 0.0472(8) Uani d . 1 . . C
C2 0.4803(3) 0.1765(4) 1.0375(2) 0.0500(8) Uani d . 1 . . C
C3 0.3610(3) 0.1138(4) 1.00385(18) 0.0455(8) Uani d . 1 . . C
C4 0.1843(3) 0.1059(4) 0.9084(2) 0.0577(10) Uani d . 1 . . C
C5 0.1530(3) -0.0139(4) 0.9445(2) 0.0648(11) Uani d . 1 . . C
H5 0.0798 -0.0563 0.9209 0.078 Uiso calc R 1 . . H
C6 0.3286(3) -0.0033(4) 1.04180(19) 0.0482(8) Uani d . 1 . . C
C7 0.6858(3) 0.0088(4) 1.2468(2) 0.0551(9) Uani d . 1 . . C
H7 0.7143 0.0693 1.2135 0.066 Uiso calc R 1 . . H
C8 0.8783(3) 0.0270(5) 1.3453(3) 0.0806(13) Uani d . 1 . . C
H8A 0.8948 0.0834 1.3029 0.121 Uiso calc R 1 . . H
H8B 0.9313 -0.0530 1.3574 0.121 Uiso calc R 1 . . H
H8C 0.8891 0.0841 1.3935 0.121 Uiso calc R 1 . . H
C9 0.7174(4) -0.1125(6) 1.3747(3) 0.0910(16) Uani d . 1 . . C
H9A 0.6995 -0.0535 1.4156 0.136 Uiso calc R 1 . . H
H9B 0.7792 -0.1784 1.4005 0.136 Uiso calc R 1 . . H
H9C 0.6478 -0.1645 1.3458 0.136 Uiso calc R 1 . . H
C10 0.3790(3) -0.1824(4) 1.1519(2) 0.0586(9) Uani d . 1 . . C
H10A 0.3221 -0.2406 1.1125 0.070 Uiso calc R 1 . . H
H10B 0.4502 -0.2383 1.1743 0.070 Uiso calc R 1 . . H
C11 0.3754(3) -0.1999(4) 1.2901(2) 0.0545(9) Uani d . 1 . . C
C12 0.3328(3) -0.1250(4) 1.3547(2) 0.0588(10) Uani d . 1 . . C
C13 0.3673(4) 0.0329(5) 1.3575(3) 0.0841(13) Uani d . 1 . . C
H13A 0.4512 0.0409 1.3656 0.126 Uiso calc R 1 . . H
H13B 0.3467 0.0788 1.4018 0.126 Uiso calc R 1 . . H
H13C 0.3258 0.0779 1.3069 0.126 Uiso calc R 1 . . H
C14 0.3916(4) -0.1932(5) 1.4373(3) 0.0866(14) Uani d . 1 . . C
H14A 0.3738 -0.2933 1.4347 0.130 Uiso calc R 1 . . H
H14B 0.3622 -0.1492 1.4784 0.130 Uiso calc R 1 . . H
H14C 0.4758 -0.1800 1.4507 0.130 Uiso calc R 1 . . H
C15 0.1988(4) -0.1399(7) 1.3344(3) 0.1033(18) Uani d . 1 . . C
H15A 0.1621 -0.0919 1.2838 0.155 Uiso calc R 1 . . H
H15B 0.1722 -0.0980 1.3773 0.155 Uiso calc R 1 . . H
H15C 0.1778 -0.2391 1.3293 0.155 Uiso calc R 1 . . H
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
Cl1 0.0707(6) 0.0874(8) 0.0753(7) 0.0066(6) -0.0219(5) 0.0030(6)
O1 0.0592(15) 0.0805(19) 0.0625(16) -0.0131(14) 0.0048(12) 0.0178(15)
O2 0.0500(13) 0.0728(18) 0.0541(15) 0.0051(12) 0.0112(11) 0.0181(13)
O3 0.089(2) 0.0612(18) 0.0729(18) 0.0175(16) 0.0144(15) 0.0172(15)
N1 0.0479(15) 0.0514(18) 0.0438(16) -0.0056(13) 0.0049(12) -0.0019(13)
N2 0.0408(14) 0.0592(18) 0.0445(16) -0.0014(13) 0.0060(12) 0.0033(14)
N3 0.0494(15) 0.0560(18) 0.0450(16) 0.0032(14) 0.0049(12) -0.0055(14)
N4 0.0523(17) 0.0592(19) 0.0595(19) -0.0097(15) 0.0016(14) -0.0087(16)
N5 0.0434(15) 0.064(2) 0.0443(16) 0.0025(14) 0.0055(12) 0.0005(14)
N6 0.0425(15) 0.071(2) 0.0489(17) 0.0091(14) 0.0000(13) 0.0015(15)
C1 0.0432(17) 0.055(2) 0.0422(18) 0.0042(16) 0.0101(14) -0.0056(16)
C2 0.0487(18) 0.054(2) 0.0455(19) 0.0001(16) 0.0111(15) -0.0003(17)
C3 0.0424(17) 0.055(2) 0.0361(17) 0.0028(15) 0.0056(13) -0.0080(16)
C4 0.054(2) 0.058(2) 0.053(2) 0.0034(18) 0.0007(16) -0.0120(18)
C5 0.052(2) 0.068(3) 0.062(2) -0.0082(19) -0.0048(18) -0.013(2)
C6 0.0497(18) 0.051(2) 0.0412(18) -0.0026(16) 0.0081(15) -0.0094(16)
C7 0.054(2) 0.057(2) 0.051(2) 0.0037(18) 0.0094(16) 0.0010(18)
C8 0.055(2) 0.091(3) 0.079(3) -0.008(2) -0.008(2) -0.001(3)
C9 0.059(2) 0.147(5) 0.060(3) 0.016(3) 0.008(2) 0.032(3)
C10 0.062(2) 0.052(2) 0.056(2) -0.0058(19) 0.0082(17) 0.0021(18)
C11 0.0436(18) 0.052(2) 0.061(2) -0.0064(17) 0.0036(16) 0.0145(18)
C12 0.0463(19) 0.071(3) 0.058(2) 0.0003(18) 0.0129(16) 0.014(2)
C13 0.093(3) 0.075(3) 0.088(3) 0.006(3) 0.031(3) 0.001(3)
C14 0.089(3) 0.103(4) 0.069(3) 0.007(3) 0.023(2) 0.020(3)
C15 0.053(2) 0.165(5) 0.096(4) -0.004(3) 0.027(2) 0.014(4)
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -2 -4
-1 -3 -1
-2 -2 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
C11 O2 C10 116.9(3) no
C6 N1 C1 119.0(3) no
C6 N1 C10 121.1(3) no
C1 N1 C10 119.9(3) no
C1 N2 C2 121.9(3) no
C4 N3 C3 115.7(3) no
C5 N4 C6 115.2(3) no
C7 N5 C1 115.8(3) no
C7 N6 C9 121.7(3) no
C7 N6 C8 121.9(3) no
C9 N6 C8 116.4(3) no
N2 C1 N5 123.7(3) no
N2 C1 N1 122.8(3) no
N5 C1 N1 113.5(3) no
O1 C2 N2 122.1(3) no
O1 C2 C3 121.0(3) no
N2 C2 C3 116.9(3) no
N3 C3 C6 121.3(3) no
N3 C3 C2 119.2(3) no
C6 C3 C2 119.5(3) no
N3 C4 C5 123.3(3) no
N3 C4 Cl1 117.0(3) no
C5 C4 Cl1 119.7(3) no
N4 C5 C4 121.8(3) no
N4 C5 H5 119.1 no
C4 C5 H5 119.1 no
N4 C6 C3 122.6(3) no
N4 C6 N1 118.0(3) no
C3 C6 N1 119.3(3) no
N6 C7 N5 123.7(4) no
N6 C7 H7 118.2 no
N5 C7 H7 118.2 no
N6 C8 H8A 109.5 no
N6 C8 H8B 109.5 no
H8A C8 H8B 109.5 no
N6 C8 H8C 109.5 no
H8A C8 H8C 109.5 no
H8B C8 H8C 109.5 no
N6 C9 H9A 109.5 no
N6 C9 H9B 109.5 no
H9A C9 H9B 109.5 no
N6 C9 H9C 109.5 no
H9A C9 H9C 109.5 no
H9B C9 H9C 109.5 no
O2 C10 N1 107.7(3) no
O2 C10 H10A 110.2 no
N1 C10 H10A 110.2 no
O2 C10 H10B 110.2 no
N1 C10 H10B 110.2 no
H10A C10 H10B 108.5 no
O3 C11 O2 122.9(4) no
O3 C11 C12 126.1(3) no
O2 C11 C12 111.0(3) no
C11 C12 C14 108.9(3) no
C11 C12 C15 109.4(3) no
C14 C12 C15 109.9(3) no
C11 C12 C13 109.3(3) no
C14 C12 C13 109.3(4) no
C15 C12 C13 110.1(4) no
C12 C13 H13A 109.5 no
C12 C13 H13B 109.5 no
H13A C13 H13B 109.5 no
C12 C13 H13C 109.5 no
H13A C13 H13C 109.5 no
H13B C13 H13C 109.5 no
C12 C14 H14A 109.5 no
C12 C14 H14B 109.5 no
H14A C14 H14B 109.5 no
C12 C14 H14C 109.5 no
H14A C14 H14C 109.5 no
H14B C14 H14C 109.5 no
C12 C15 H15A 109.5 no
C12 C15 H15B 109.5 no
H15A C15 H15B 109.5 no
C12 C15 H15C 109.5 no
H15A C15 H15C 109.5 no
H15B C15 H15C 109.5 no
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
Cl1 C4 . 1.730(4) no
O1 C2 . 1.228(4) no
O2 C11 . 1.349(4) no
O2 C10 . 1.438(4) no
O3 C11 . 1.194(4) no
N1 C6 . 1.386(4) no
N1 C1 . 1.392(4) no
N1 C10 . 1.442(4) no
N2 C1 . 1.318(4) no
N2 C2 . 1.361(4) no
N3 C4 . 1.314(4) no
N3 C3 . 1.340(4) no
N4 C5 . 1.326(4) no
N4 C6 . 1.342(4) no
N5 C7 . 1.314(4) no
N5 C1 . 1.346(4) no
N6 C7 . 1.296(4) no
N6 C9 . 1.445(5) no
N6 C8 . 1.461(4) no
C2 C3 . 1.479(4) no
C3 C6 . 1.383(5) no
C4 C5 . 1.382(5) no
C5 H5 . 0.9300 no
C7 H7 . 0.9300 no
C8 H8A . 0.9600 no
C8 H8B . 0.9600 no
C8 H8C . 0.9600 no
C9 H9A . 0.9600 no
C9 H9B . 0.9600 no
C9 H9C . 0.9600 no
C10 H10A . 0.9700 no
C10 H10B . 0.9700 no
C11 C12 . 1.509(5) no
C12 C14 . 1.522(5) no
C12 C15 . 1.522(5) no
C12 C13 . 1.532(6) no
C13 H13A . 0.9600 no
C13 H13B . 0.9600 no
C13 H13C . 0.9600 no
C14 H14A . 0.9600 no
C14 H14B . 0.9600 no
C14 H14C . 0.9600 no
C15 H15A . 0.9600 no
C15 H15B . 0.9600 no
C15 H15C . 0.9600 no
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
C2 N2 C1 N5 -179.6(3) no
C2 N2 C1 N1 -0.1(5) no
C7 N5 C1 N2 -10.9(5) no
C7 N5 C1 N1 169.5(3) no
C6 N1 C1 N2 -4.6(5) no
C10 N1 C1 N2 174.5(3) no
C6 N1 C1 N5 175.0(3) no
C10 N1 C1 N5 -6.0(4) no
C1 N2 C2 O1 -173.7(3) no
C1 N2 C2 C3 6.0(5) no
C4 N3 C3 C6 -1.4(5) no
C4 N3 C3 C2 177.6(3) no
O1 C2 C3 N3 -6.9(5) no
N2 C2 C3 N3 173.4(3) no
O1 C2 C3 C6 172.2(3) no
N2 C2 C3 C6 -7.5(5) no
C3 N3 C4 C5 -0.7(5) no
C3 N3 C4 Cl1 177.7(2) no
C6 N4 C5 C4 -0.6(6) no
N3 C4 C5 N4 1.8(6) no
Cl1 C4 C5 N4 -176.6(3) no
C5 N4 C6 C3 -1.6(5) no
C5 N4 C6 N1 178.9(3) no
N3 C3 C6 N4 2.7(5) no
C2 C3 C6 N4 -176.3(3) no
N3 C3 C6 N1 -177.8(3) no
C2 C3 C6 N1 3.1(5) no
C1 N1 C6 N4 -177.8(3) no
C10 N1 C6 N4 3.2(5) no
C1 N1 C6 C3 2.7(5) no
C10 N1 C6 C3 -176.3(3) no
C9 N6 C7 N5 -2.6(6) no
C8 N6 C7 N5 177.8(4) no
C1 N5 C7 N6 174.9(3) no
C11 O2 C10 N1 -131.6(3) no
C6 N1 C10 O2 -97.3(3) no
C1 N1 C10 O2 83.7(4) no
C10 O2 C11 O3 -10.9(5) no
C10 O2 C11 C12 169.6(3) no
O3 C11 C12 C14 3.6(5) no
O2 C11 C12 C14 -176.9(3) no
O3 C11 C12 C15 -116.4(4) no
O2 C11 C12 C15 63.1(4) no
O3 C11 C12 C13 122.9(4) no
O2 C11 C12 C13 -57.6(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652221
2 PubChem 10992194