#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/04/7150421.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_7150421
loop_
_publ_author_name
'Hornillo-Araujo, Ana R'
'Burrell, Adam J. M.'
'Aiertza, Miren K.'
'Shibata, Takayuki'
'Hammond, David M.'
'Edmont, Dolorès'
'Adams, Harry'
'Margison, Geoffrey P.'
'Williams, David M.'
_publ_section_title
;
 The syntheses and properties of tricyclic pyrrolo[2,3-d]pyrimidine
 analogues of S6-methylthioguanine and O6-methylguanine.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1723
_journal_page_last               1729
_journal_paper_doi               10.1039/b516447h
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C10 H12 N4 O'
_chemical_formula_weight         204.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9420(17)
_cell_length_b                   13.862(3)
_cell_length_c                   8.4623(19)
_cell_measurement_reflns_used    3463
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      54.322
_cell_measurement_theta_min      5.640
_cell_volume                     931.6(4)
_computing_cell_refinement       'Bruker smart'
_computing_data_collection       'Bruker smart'
_computing_data_reduction        'Bruker saint'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker smart1000'
_diffrn_measurement_method       'ω 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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9204
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1141
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0450
_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)+(0.0557P)²+0.7603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                1001
_reflns_number_total             1141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b516447h.txt
_cod_data_source_block           odw32
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7150421
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'
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
N2 N 0.1733(3) 0.73321(19) 0.5579(3) 0.0206(6) Uani 1 1 d . . .
N3 N 0.1030(3) 0.88869(19) 0.4547(3) 0.0201(6) Uani 1 1 d . . .
N4 N 0.0374(4) 1.02768(19) 0.3162(4) 0.0261(6) Uani 1 1 d . . .
H4A H 0.0600 1.0617 0.4014 0.031 Uiso 1 1 calc R . .
H4B H 0.0048 1.0569 0.2291 0.031 Uiso 1 1 calc R . .
N5 N 0.0184(3) 0.88467(18) 0.1803(4) 0.0193(6) Uani 1 1 d . . .
O6 O -0.0114(3) 0.75115(17) 0.0350(3) 0.0224(5) Uani 1 1 d . . .
C1 C 0.1754(4) 0.6390(2) 0.4992(4) 0.0203(7) Uani 1 1 d . . .
H1A H 0.2141 0.5842 0.5561 0.024 Uiso 1 1 calc R . .
C4 C 0.0530(4) 0.9297(2) 0.3192(4) 0.0195(7) Uani 1 1 d . . .
C7 C -0.0427(4) 0.6481(2) 0.0244(5) 0.0257(7) Uani 1 1 d . . .
H7A H -0.0770 0.6328 -0.0853 0.031 Uiso 1 1 calc R . .
H7B H -0.1387 0.6321 0.0942 0.031 Uiso 1 1 calc R . .
C8 C 0.1050(4) 0.5836(2) 0.0684(4) 0.0219(7) Uani 1 1 d . . .
H8A H 0.2115 0.6187 0.0489 0.026 Uiso 1 1 calc R . .
H8B H 0.1042 0.5256 0.0000 0.026 Uiso 1 1 calc R . .
C9 C 0.0984(4) 0.5522(2) 0.2414(4) 0.0207(7) Uani 1 1 d . . .
H9A H -0.0097 0.5189 0.2620 0.025 Uiso 1 1 calc R . .
H9B H 0.1908 0.5060 0.2625 0.025 Uiso 1 1 calc R . .
C10 C 0.1146(4) 0.6369(2) 0.3502(4) 0.0178(6) Uani 1 1 d . . .
C11 C 0.0745(4) 0.7358(2) 0.3101(4) 0.0179(6) Uani 1 1 d . . .
C12 C 0.0262(4) 0.7886(2) 0.1779(4) 0.0178(6) Uani 1 1 d . . .
C13 C 0.1152(4) 0.7921(2) 0.4428(4) 0.0174(6) Uani 1 1 d . . .
C14 C 0.2494(4) 0.7649(2) 0.7052(4) 0.0236(7) Uani 1 1 d . . .
H14A H 0.2304 0.8343 0.7188 0.035 Uiso 1 1 calc R . .
H14B H 0.3706 0.7520 0.7026 0.035 Uiso 1 1 calc R . .
H14C H 0.1984 0.7299 0.7937 0.035 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0241(13) 0.0229(14) 0.0148(13) -0.0018(12) -0.0025(11) 0.0008(10)
N3 0.0206(12) 0.0184(13) 0.0213(15) -0.0042(11) -0.0008(11) 0.0013(10)
N4 0.0325(15) 0.0173(13) 0.0285(16) 0.0005(13) -0.0059(14) -0.0010(11)
N5 0.0196(12) 0.0173(13) 0.0209(14) 0.0032(12) -0.0003(11) 0.0031(10)
O6 0.0317(12) 0.0193(10) 0.0162(11) -0.0006(10) -0.0046(10) 0.0037(9)
C1 0.0207(14) 0.0201(15) 0.0200(16) 0.0014(13) -0.0005(13) 0.0009(12)
C4 0.0157(12) 0.0195(15) 0.0234(17) 0.0003(14) 0.0000(13) -0.0007(12)
C7 0.0304(16) 0.0224(16) 0.0242(18) -0.0016(15) -0.0103(15) 0.0011(13)
C8 0.0276(16) 0.0192(15) 0.0188(17) -0.0018(13) -0.0035(14) 0.0032(13)
C9 0.0259(16) 0.0166(14) 0.0195(16) 0.0004(13) -0.0037(14) -0.0007(12)
C10 0.0197(14) 0.0156(14) 0.0180(16) 0.0021(12) 0.0020(12) 0.0008(11)
C11 0.0175(13) 0.0174(14) 0.0187(16) -0.0013(14) -0.0005(12) 0.0011(12)
C12 0.0167(13) 0.0199(15) 0.0168(15) 0.0004(14) 0.0015(12) -0.0010(12)
C13 0.0168(13) 0.0192(14) 0.0162(15) 0.0012(13) -0.0002(12) -0.0006(12)
C14 0.0280(16) 0.0258(16) 0.0170(17) -0.0042(13) -0.0038(13) 0.0031(13)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C13 N2 C1 108.2(3) . . ?
C13 N2 C14 125.2(3) . . ?
C1 N2 C14 125.6(3) . . ?
C4 N3 C13 112.3(3) . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C12 N5 C4 117.6(3) . . ?
C12 O6 C7 118.1(3) . . ?
C10 C1 N2 110.4(3) . . ?
C10 C1 H1A 124.8 . . ?
N2 C1 H1A 124.8 . . ?
N3 C4 N5 127.3(3) . . ?
N3 C4 N4 117.7(3) . . ?
N5 C4 N4 115.0(3) . . ?
O6 C7 C8 115.5(3) . . ?
O6 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
O6 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 112.0(3) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 111.3(3) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C1 C10 C11 106.0(3) . . ?
C1 C10 C9 128.5(3) . . ?
C11 C10 C9 125.4(3) . . ?
C12 C11 C13 114.4(3) . . ?
C12 C11 C10 138.4(3) . . ?
C13 C11 C10 106.8(3) . . ?
N5 C12 O6 112.8(3) . . ?
N5 C12 C11 121.7(3) . . ?
O6 C12 C11 125.4(3) . . ?
N3 C13 N2 124.9(3) . . ?
N3 C13 C11 126.6(3) . . ?
N2 C13 C11 108.6(3) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
N2 C13 1.352(4) . ?
N2 C1 1.397(4) . ?
N2 C14 1.454(4) . ?
N3 C4 1.340(5) . ?
N3 C13 1.346(4) . ?
N4 C4 1.365(4) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 C12 1.333(4) . ?
N5 C4 1.358(5) . ?
O6 C12 1.349(4) . ?
O6 C7 1.453(4) . ?
C1 C10 1.351(4) . ?
C1 H1A 0.9500 . ?
C7 C8 1.522(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.528(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.497(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.448(4) . ?
C11 C12 1.391(5) . ?
C11 C13 1.406(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A N5 0.88 2.55 3.342(4) 149.8 2_575
N4 H4B N3 0.88 2.59 3.456(4) 169.5 2_574
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9746761
