#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:51:47 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179543 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/12/4501283.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_4501283
loop_
_publ_author_name
'McHugh, Charlene'
'Erxleben, Andrea'
_publ_section_title
;
 Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine
 and Pharmaceutically RelevantN6-Substituted Adenine
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5096
_journal_paper_doi               10.1021/cg201007m
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C16 H15 N5 O4'
_chemical_formula_weight         341.33
_chemical_name_systematic
; 
 ? 
;
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.613(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0215(11)
_cell_length_b                   5.1904(5)
_cell_length_c                   33.712(3)
_cell_measurement_reflns_used    5369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      3.61
_cell_volume                     1571.0(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1048
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0899
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5369
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0742
_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)+(0.0372P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                1718
_reflns_number_total             2772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201007m_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4501283
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_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
N3 N 0.0934(4) 0.9433(6) 0.05484(9) 0.0391(8) Uani 1 1 d .
N7 N -0.1584(3) 0.4386(6) 0.05814(9) 0.0375(8) Uani 1 1 d .
N1 N 0.1511(3) 0.7667(5) 0.11926(9) 0.0403(8) Uani 1 1 d .
N9 N -0.1097(4) 0.7395(5) 0.01332(9) 0.0406(8) Uani 1 1 d .
N6 N 0.0268(4) 0.4101(6) 0.14078(9) 0.0417(8) Uani 1 1 d .
H14 H -0.083(5) 0.747(8) 0.3071(14) 0.084(16) Uiso 1 1 d .
H13 H -0.163(5) 0.924(8) 0.2437(12) 0.074(15) Uiso 1 1 d .
H15 H 0.075(5) 0.378(9) 0.3117(15) 0.106(18) Uiso 1 1 d .
H12 H -0.067(4) 0.783(6) 0.1879(11) 0.045(11) Uiso 1 1 d .
H2 H 0.247(4) 1.066(7) 0.0966(11) 0.060(12) Uiso 1 1 d .
H8 H -0.268(4) 0.467(6) 0.0022(10) 0.051(11) Uiso 1 1 d .
H7 H -0.208(4) 0.290(7) 0.0680(11) 0.060(12) Uiso 1 1 d .
H3 H 0.120(5) 1.077(8) 0.0328(13) 0.097(15) Uiso 1 1 d .
H6 H -0.057(4) 0.285(6) 0.1369(10) 0.054(11) Uiso 1 1 d .
C2 C 0.1709(5) 0.9348(7) 0.09096(12) 0.0427(10) Uani 1 1 d .
C4 C -0.0162(4) 0.7654(6) 0.04775(11) 0.0348(9) Uani 1 1 d .
C5 C -0.0427(4) 0.5854(6) 0.07582(10) 0.0320(8) Uani 1 1 d .
C6 C 0.0453(4) 0.5820(6) 0.11284(10) 0.0323(8) Uani 1 1 d .
C8 C -0.1935(5) 0.5391(7) 0.02142(12) 0.0423(10) Uani 1 1 d .
C10 C 0.1250(4) 0.3855(7) 0.17772(11) 0.0475(10) Uani 1 1 d .
H10A H 0.2167 0.4781 0.1748 0.057 Uiso 1 1 calc R
H10B H 0.1502 0.2052 0.1818 0.057 Uiso 1 1 calc R
C11 C 0.0591(4) 0.4855(7) 0.21420(11) 0.0416(10) Uani 1 1 d .
C12 C -0.0359(5) 0.6933(8) 0.21278(14) 0.0546(12) Uani 1 1 d .
C13 C -0.0909(6) 0.7835(10) 0.24703(17) 0.0711(15) Uani 1 1 d .
C14 C -0.0480(6) 0.6684(11) 0.28335(16) 0.0737(15) Uani 1 1 d .
C15 C 0.0472(6) 0.4678(11) 0.28486(15) 0.0733(15) Uani 1 1 d .
C16 C 0.1008(5) 0.3727(8) 0.25084(12) 0.0585(12) Uani 1 1 d .
H16 H 0.1651 0.2322 0.2525 0.070 Uiso 1 1 calc R
C17 C 0.4383(4) 0.5666(7) 0.07247(11) 0.0399(9) Uani 1 1 d .
C18 C 0.5229(5) 0.5700(8) 0.11301(12) 0.0464(10) Uani 1 1 d .
C19 C 0.6285(5) 0.7218(7) 0.12900(12) 0.0443(10) Uani 1 1 d .
C20 C 0.7052(4) 0.9467(7) 0.11247(12) 0.0406(9) Uani 1 1 d .
O1 O 0.3428(3) 0.4053(5) 0.06529(8) 0.0601(8) Uani 1 1 d .
O2 O 0.4671(3) 0.7389(5) 0.04646(8) 0.0581(8) Uani 1 1 d .
O3 O 0.8042(3) 1.0510(5) 0.13492(9) 0.0645(9) Uani 1 1 d .
H19 H 0.665(5) 0.689(7) 0.1572(12) 0.071(13) Uiso 1 1 d .
H18 H 0.484(4) 0.423(6) 0.1291(9) 0.040(10) Uiso 1 1 d .
O4 O 0.6688(3) 1.0225(5) 0.07713(8) 0.0524(8) Uani 1 1 d .
H2A H 0.568(6) 0.888(10) 0.0576(16) 0.126(19) Uiso 1 1 d .
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N3 C4 116.3(3)
C2 N3 H3 121(2)
C4 N3 H3 122(2)
C8 N7 C5 106.4(3)
C8 N7 H7 123(2)
C5 N7 H7 130(2)
C2 N1 C6 119.7(3)
C8 N9 C4 102.6(3)
C6 N6 C10 124.0(3)
C6 N6 H6 120(2)
C10 N6 H6 116(2)
N1 C2 N3 125.6(4)
N1 C2 H2 118(2)
N3 C2 H2 117(2)
N3 C4 C5 121.1(3)
N3 C4 N9 126.3(3)
C5 C4 N9 112.6(3)
C4 C5 N7 104.8(3)
C4 C5 C6 119.9(3)
N7 C5 C6 135.3(3)
N6 C6 N1 120.0(3)
N6 C6 C5 122.7(3)
N1 C6 C5 117.3(3)
N9 C8 N7 113.7(4)
N9 C8 H8 123(2)
N7 C8 H8 124(2)
N6 C10 C11 114.2(3)
N6 C10 H10A 108.7
C11 C10 H10A 108.7
N6 C10 H10B 108.7
C11 C10 H10B 108.7
H10A C10 H10B 107.6
C12 C11 C16 118.4(4)
C12 C11 C10 122.4(4)
C16 C11 C10 119.1(4)
C11 C12 C13 120.6(4)
C11 C12 H12 122(2)
C13 C12 H12 117(2)
C12 C13 C14 120.1(5)
C12 C13 H13 117(3)
C14 C13 H13 123(3)
C15 C14 C13 119.3(5)
C15 C14 H14 123(3)
C13 C14 H14 117(3)
C14 C15 C16 121.3(5)
C14 C15 H15 119(3)
C16 C15 H15 120(3)
C15 C16 C11 120.2(4)
C15 C16 H16 119.9
C11 C16 H16 119.9
O1 C17 O2 121.9(4)
O1 C17 C18 118.7(3)
O2 C17 C18 119.4(3)
C19 C18 C17 131.8(4)
C19 C18 H18 120.6(19)
C17 C18 H18 107.6(19)
C18 C19 C20 131.4(4)
C18 C19 H19 117(2)
C20 C19 H19 112(2)
O3 C20 O4 123.0(4)
O3 C20 C19 116.6(4)
O4 C20 C19 120.5(3)
C17 O2 H2A 115(2)
C20 O4 H2A 115(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C2 1.344(5)
N3 C4 1.357(4)
N3 H3 1.06(4)
N7 C8 1.352(5)
N7 C5 1.380(4)
N7 H7 0.97(4)
N1 C2 1.318(4)
N1 C6 1.355(4)
N9 C8 1.330(4)
N9 C4 1.373(4)
N6 C6 1.320(4)
N6 C10 1.461(4)
N6 H6 1.00(4)
C2 H2 0.97(4)
C4 C5 1.367(5)
C5 C6 1.412(4)
C8 H8 0.96(4)
C10 C11 1.510(5)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.376(5)
C11 C16 1.385(5)
C12 C13 1.382(6)
C12 H12 0.97(3)
C13 C14 1.383(7)
C13 H13 0.97(4)
C14 C15 1.348(7)
C14 H14 0.98(4)
C15 C16 1.379(6)
C15 H15 1.03(5)
C16 H16 0.9300
C17 O1 1.208(4)
C17 O2 1.297(4)
C17 C18 1.499(5)
C18 C19 1.311(5)
C18 H18 1.02(3)
C19 C20 1.492(5)
C19 H19 0.99(4)
C20 O3 1.237(4)
C20 O4 1.267(4)
O2 H2A 1.22(6)
O4 H2A 1.28(6)
