#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/23/2212383.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_2212383
loop_
_publ_author_name
'Trávníček, Zdeněk'
'Popa, Igor'
_publ_section_title
;
 2-Chloro-6-[(2,6-dimethoxybenzyl)amino]-9-isopropylpurine
 0.125-hydrate
;
_journal_coeditor_code           TK2117
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o629
_journal_page_last               o631
_journal_paper_doi               10.1107/S1600536807000268
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H20 Cl N5 O2, 0.125H2 O'
_chemical_formula_moiety         'C17 H20 Cl N5 O2, 0.125(H2 O)'
_chemical_formula_sum            'C17 H20.25 Cl N5 O2.125'
_chemical_formula_weight         364.08
_chemical_melting_point          398.8(5)
_chemical_name_systematic
;
2-Chloro-6-[(2,6-dimethoxybenzyl)amino]-9-isopropylpurine 0.125-hydrate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 112.32(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.159(5)
_cell_length_b                   11.931(2)
_cell_length_c                   11.785(2)
_cell_measurement_reflns_used    6240
_cell_measurement_temperature    109(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      1.6
_cell_volume                     3532.6(13)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL97 and DIAMOND'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      109(2)
_diffrn_detector_area_resol_mean 16.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Enhance (Oxford Diffraction)'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13528
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1530
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.10
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.035P)²+5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.083
_refine_ls_wR_factor_ref         0.087
_reflns_number_gt                2808
_reflns_number_total             3099
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2117.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '398.3--399.3' was changed to
'398.8(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '398.3--399.3' was changed to
'398.8(5)' - 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_cell_volume        3532.6(12)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212383
_cod_database_fobs_code          2212383
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_type_symbol
_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
Cl Cl1 0.705748(16) 0.19804(4) 0.62131(4) 0.02781(14) Uani d . 1
O O1 0.44644(5) 0.28631(10) 0.27419(11) 0.0271(3) Uani d D 1
O O2 0.44794(5) 0.06237(10) 0.59774(10) 0.0235(3) Uani d . 1
N N1 0.61133(5) 0.22264(11) 0.62130(12) 0.0183(3) Uani d . 1
N N3 0.68545(5) 0.28863(12) 0.79865(12) 0.0190(3) Uani d . 1
N N6 0.52347(5) 0.24338(12) 0.59943(12) 0.0187(3) Uani d D 1
H H6A 0.4998 0.2758 0.6231 0.022 Uiso calc R 1
N N7 0.56714(5) 0.34981(12) 0.85358(12) 0.0191(3) Uani d . 1
N N9 0.65555(5) 0.37486(11) 0.95019(12) 0.0172(3) Uani d . 1
C C2 0.66201(6) 0.24180(14) 0.69022(15) 0.0192(4) Uani d . 1
C C4 0.64794(6) 0.32274(13) 0.84088(14) 0.0167(3) Uani d . 1
C C5 0.59353(6) 0.30978(14) 0.78232(14) 0.0165(3) Uani d . 1
C C6 0.57475(6) 0.25819(13) 0.66608(14) 0.0170(3) Uani d . 1
C C8 0.60566(6) 0.38707(14) 0.95192(15) 0.0189(4) Uani d . 1
H H8A 0.5995 0.4198 1.0189 0.023 Uiso calc R 1
C C9 0.50478(6) 0.17529(14) 0.48825(15) 0.0188(4) Uani d . 1
H H9A 0.5190 0.0983 0.5082 0.023 Uiso calc R 1
H H9B 0.5183 0.2071 0.4281 0.023 Uiso calc R 1
C C10 0.44508(6) 0.17101(13) 0.43225(14) 0.0166(3) Uani d . 1
C C11 0.41632(7) 0.22614(14) 0.32273(15) 0.0199(4) Uani d . 1
C C12 0.36119(7) 0.21817(15) 0.26952(16) 0.0247(4) Uani d . 1
H H12A 0.3420 0.2547 0.1940 0.030 Uiso calc R 1
C C13 0.33470(7) 0.15659(15) 0.32767(17) 0.0273(4) Uani d . 1
H H13A 0.2970 0.1515 0.2917 0.033 Uiso calc R 1
C C14 0.36183(7) 0.10211(15) 0.43714(17) 0.0247(4) Uani d . 1
H H14A 0.3432 0.0599 0.4764 0.030 Uiso calc R 1
C C15 0.41684(7) 0.11026(14) 0.48859(15) 0.0195(4) Uani d . 1
C C16 0.70704(7) 0.40960(15) 1.04549(14) 0.0212(4) Uani d . 1
H H16A 0.7292 0.3413 1.0785 0.025 Uiso calc R 1
C C17 0.73660(7) 0.48659(17) 0.99012(16) 0.0295(4) Uani d . 1
H H17A 0.7424 0.4477 0.9230 0.044 Uiso calc R 1
H H17B 0.7710 0.5073 1.0533 0.044 Uiso calc R 1
H H17C 0.7154 0.5544 0.9584 0.044 Uiso calc R 1
C C18 0.69786(8) 0.46835(16) 1.14968(16) 0.0278(4) Uani d . 1
H H18A 0.6800 0.4171 1.1867 0.042 Uiso calc R 1
H H18B 0.6755 0.5346 1.1180 0.042 Uiso calc R 1
H H18C 0.7321 0.4914 1.2118 0.042 Uiso calc R 1
C C19 0.41943(8) 0.35514(18) 0.17025(17) 0.0349(5) Uani d . 1
H H19A 0.4455 0.3985 0.1495 0.052 Uiso calc R 1
H H19B 0.3955 0.4065 0.1893 0.052 Uiso calc R 1
H H19C 0.3987 0.3078 0.1004 0.052 Uiso calc R 1
C C20 0.42197(8) -0.00429(17) 0.65928(18) 0.0326(5) Uani d . 1
H H20A 0.4486 -0.0351 0.7348 0.049 Uiso calc R 1
H H20B 0.4028 -0.0658 0.6056 0.049 Uiso calc R 1
H H20C 0.3968 0.0423 0.6796 0.049 Uiso calc R 1
O O3 0.5192(8) 0.4922(12) 1.0747(19) 0.124(9) Uani d PD 0.125
H H3V 0.5070 0.5589 1.0985 0.185 Uiso d PD 0.125
H H3W 0.5293 0.4226 1.1182 0.185 Uiso d PD 0.125
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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C11 O1 C19 . . 117.91(14)
C11 O1 O3 . 2_656 106.6(3)
C19 O1 O3 . 2_656 88.9(4)
C15 O2 C20 . . 117.53(14)
C15 O2 N6 . . 83.16(9)
C20 O2 N6 . . 150.75(11)
C2 N1 C6 . . 116.79(14)
C2 N3 C4 . . 109.28(14)
C6 N6 C9 . . 122.36(14)
C6 N6 O2 . . 131.89(11)
C9 N6 O2 . . 65.53(8)
C6 N6 H6A . . 118.8
C9 N6 H6A . . 118.8
O2 N6 H6A . . 74.8
C8 N7 C5 . . 103.36(13)
C8 N9 C4 . . 105.34(13)
C8 N9 C16 . . 127.80(14)
C4 N9 C16 . . 126.86(13)
N3 C2 N1 . . 132.45(15)
N3 C2 Cl1 . . 114.39(12)
N1 C2 Cl1 . . 113.15(12)
N3 C4 N9 . . 127.89(14)
N3 C4 C5 . . 126.41(15)
N9 C4 C5 . . 105.69(14)
N7 C5 C4 . . 111.19(14)
N7 C5 C6 . . 131.54(15)
C4 C5 C6 . . 117.26(15)
N6 C6 N1 . . 119.16(14)
N6 C6 C5 . . 123.04(15)
N1 C6 C5 . . 117.80(14)
N7 C8 N9 . . 114.39(14)
N7 C8 H8A . . 122.8
N9 C8 H8A . . 122.8
N6 C9 C10 . . 111.28(13)
N6 C9 H9A . . 109.4
C10 C9 H9A . . 109.4
N6 C9 H9B . . 109.4
C10 C9 H9B . . 109.4
H9A C9 H9B . . 108.0
C15 C10 C11 . . 118.07(15)
C15 C10 C9 . . 120.42(14)
C11 C10 C9 . . 121.51(15)
O1 C11 C12 . . 124.11(15)
O1 C11 C10 . . 114.94(14)
C12 C11 C10 . . 120.95(16)
C13 C12 C11 . . 119.23(16)
C13 C12 H12A . . 120.4
C11 C12 H12A . . 120.4
C12 C13 C14 . . 121.39(16)
C12 C13 H13A . . 119.3
C14 C13 H13A . . 119.3
C13 C14 C15 . . 118.66(16)
C13 C14 H14A . . 120.7
C15 C14 H14A . . 120.7
O2 C15 C14 . . 124.08(15)
O2 C15 C10 . . 114.24(14)
C14 C15 C10 . . 121.67(16)
N9 C16 C18 . . 110.20(14)
N9 C16 C17 . . 110.11(13)
C18 C16 C17 . . 110.16(15)
N9 C16 H16A . . 108.8
C18 C16 H16A . . 108.8
C17 C16 H16A . . 108.8
C16 C17 H17A . . 109.5
C16 C17 H17B . . 109.5
H17A C17 H17B . . 109.5
C16 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
H17B C17 H17C . . 109.5
C16 C18 H18A . . 109.5
C16 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
C16 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
O1 C19 H19A . . 109.5
O1 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
O1 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
O2 C20 H20A . . 109.5
O2 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
O2 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
O3 O3 H3V 5_667 . 93.9(15)
O3 O3 H3W 5_667 . 126(2)
H3V O3 H3W . . 129(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C2 . 1.7538(17)
O1 C11 . 1.366(2)
O1 C19 . 1.425(2)
O1 O3 2_656 2.968(16)
O2 C15 . 1.367(2)
O2 C20 . 1.430(2)
O2 N6 . 2.9735(18)
N1 C2 . 1.326(2)
N1 C6 . 1.358(2)
N3 C2 . 1.316(2)
N3 C4 . 1.355(2)
N6 C6 . 1.325(2)
N6 C9 . 1.459(2)
N6 H6A . 0.8800
N7 C8 . 1.309(2)
N7 C5 . 1.380(2)
N9 C8 . 1.371(2)
N9 C4 . 1.374(2)
N9 C16 . 1.482(2)
C4 C5 . 1.382(2)
C5 C6 . 1.409(2)
C8 H8A . 0.9500
C9 C10 . 1.502(2)
C9 H9A . 0.9900
C9 H9B . 0.9900
C10 C15 . 1.393(2)
C10 C11 . 1.394(2)
C11 C12 . 1.390(2)
C12 C13 . 1.379(3)
C12 H12A . 0.9500
C13 C14 . 1.381(3)
C13 H13A . 0.9500
C14 C15 . 1.386(2)
C14 H14A . 0.9500
C16 C18 . 1.514(2)
C16 C17 . 1.520(2)
C16 H16A . 1.0000
C17 H17A . 0.9800
C17 H17B . 0.9800
C17 H17C . 0.9800
C18 H18A . 0.9800
C18 H18B . 0.9800
C18 H18C . 0.9800
C19 H19A . 0.9800
C19 H19B . 0.9800
C19 H19C . 0.9800
C20 H20A . 0.9800
C20 H20B . 0.9800
C20 H20C . 0.9800
O3 O3 5_667 1.68(4)
O3 H3V . 0.945(14)
O3 H3W . 0.958(15)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N6 H6A N7 2_656 0.88 2.13 3.0016(19) 170
O3 H3W O1 2_656 0.958(15) 2.0136(13) 2.968(16) 173.9(12)
O3 H3V N6 6_566 0.945(14) 2.4006(15) 3.167(14) 138.0(12)
O3 H3V N7 5_667 0.945(14) 2.5335(14) 3.358(16) 145.8(13)
C8 H8A O3 . 0.95 2.65 3.429(17) 140
C9 H9A O2 5_656 0.99 2.63 3.421(2) 138
C19 H19C N1 2_655 0.98 2.72 3.581(3) 147
C16 H16A N3 7_657 1.00 2.71 3.663(2) 160
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_site_symmetry_1
_geom_torsion
C15 O2 N6 C6 . -165.63(16)
C20 O2 N6 C6 . 56.7(3)
C15 O2 N6 C9 . -53.19(12)
C20 O2 N6 C9 . 169.2(2)
C4 N3 C2 N1 . -1.0(3)
C4 N3 C2 Cl1 . 177.73(11)
C6 N1 C2 N3 . 1.3(3)
C6 N1 C2 Cl1 . -177.46(12)
C2 N3 C4 N9 . 179.69(16)
C2 N3 C4 C5 . 1.0(2)
C8 N9 C4 N3 . -177.27(16)
C16 N9 C4 N3 . 2.5(3)
C8 N9 C4 C5 . 1.60(17)
C16 N9 C4 C5 . -178.65(14)
C8 N7 C5 C4 . 0.79(18)
C8 N7 C5 C6 . 179.35(17)
N3 C4 C5 N7 . 177.36(15)
N9 C4 C5 N7 . -1.54(18)
N3 C4 C5 C6 . -1.4(2)
N9 C4 C5 C6 . 179.68(14)
C9 N6 C6 N1 . 9.6(2)
O2 N6 C6 N1 . 94.40(17)
C9 N6 C6 C5 . -170.57(15)
O2 N6 C6 C5 . -85.75(19)
C2 N1 C6 N6 . 178.45(15)
C2 N1 C6 C5 . -1.4(2)
N7 C5 C6 N6 . 3.2(3)
C4 C5 C6 N6 . -178.33(15)
N7 C5 C6 N1 . -176.96(16)
C4 C5 C6 N1 . 1.5(2)
C5 N7 C8 N9 . 0.29(18)
C4 N9 C8 N7 . -1.23(19)
C16 N9 C8 N7 . 179.02(14)
C6 N6 C9 C10 . 178.97(14)
O2 N6 C9 C10 . 53.50(11)
N6 C9 C10 C15 . -71.48(19)
N6 C9 C10 C11 . 109.15(17)
C19 O1 C11 C12 . 7.3(2)
O3 O1 C11 C12 2_656 105.1(5)
C19 O1 C11 C10 . -172.87(15)
O3 O1 C11 C10 2_656 -75.1(5)
C15 C10 C11 O1 . 178.44(14)
C9 C10 C11 O1 . -2.2(2)
C15 C10 C11 C12 . -1.8(2)
C9 C10 C11 C12 . 177.63(15)
O1 C11 C12 C13 . -178.87(15)
C10 C11 C12 C13 . 1.3(2)
C11 C12 C13 C14 . -0.4(3)
C12 C13 C14 C15 . 0.0(3)
C20 O2 C15 C14 . 2.9(2)
N6 O2 C15 C14 . -155.27(16)
C20 O2 C15 C10 . -178.10(14)
N6 O2 C15 C10 . 23.70(13)
C13 C14 C15 O2 . 178.42(15)
C13 C14 C15 C10 . -0.5(3)
C11 C10 C15 O2 . -177.67(14)
C9 C10 C15 O2 . 2.9(2)
C11 C10 C15 C14 . 1.3(2)
C9 C10 C15 C14 . -178.07(15)
C8 N9 C16 C18 . -2.5(2)
C4 N9 C16 C18 . 177.79(15)
C8 N9 C16 C17 . -124.24(17)
C4 N9 C16 C17 . 56.1(2)
