# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_prGCl
_database_code_depnum_ccdc_archive 'CCDC 1417638'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT015_I                   
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF .... Please Do !
RESPONSE: The appended hkl part has been removed, and
deposited as a fcf file to CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        6-Chloro-9-propyl-purin-2-amine
_chemical_name_common            pr_GCl
_chemical_melting_point          none
_chemical_formula_moiety         'C8 H10 Cl N5'
_chemical_formula_sum            'C8 H10 Cl N5'
_chemical_formula_weight         211.66

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.916(7)
_cell_length_b                   14.964(7)
_cell_length_c                   15.309(7)
_cell_angle_alpha                64.365(8)
_cell_angle_beta                 89.997(8)
_cell_angle_gamma                62.904(9)
_cell_volume                     2659(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1000
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      22.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            21213
_diffrn_reflns_av_unetI/netI     0.2291
_diffrn_reflns_av_R_equivalents  0.1238
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             10218
_reflns_number_gt                3743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'Bruker XCIF'

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1592P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10218
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1766
_refine_ls_R_factor_gt           0.0989
_refine_ls_wR_factor_ref         0.3053
_refine_ls_wR_factor_gt          0.2552
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_restrained_S_all      0.865
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2840(4) 0.6308(5) 0.4368(3) 0.0719(15) Uani 1 1 d . . . . .
C2 C 0.2203(4) 0.6315(5) 0.3005(3) 0.0754(16) Uani 1 1 d . . . . .
C3 C 0.3637(3) 0.6410(4) 0.3066(3) 0.0673(14) Uani 1 1 d . . . . .
C4 C 0.3635(3) 0.6386(5) 0.3977(3) 0.0717(15) Uani 1 1 d . . . . .
C5 C 0.4963(4) 0.6469(5) 0.3565(4) 0.0757(16) Uani 1 1 d . . . . .
H5A H 0.5587 0.6496 0.3572 0.091 Uiso 1 1 calc R U . . .
C6 C 0.4808(4) 0.6568(6) 0.1870(4) 0.0746(16) Uani 1 1 d . . . . .
H6A H 0.4685 0.6068 0.1688 0.089 Uiso 1 1 calc R U . . .
H6B H 0.5562 0.6290 0.1985 0.089 Uiso 1 1 calc R U . . .
C7 C 0.4245(5) 0.7753(6) 0.1030(5) 0.099(2) Uani 1 1 d . . . . .
H7A H 0.3490 0.8053 0.0959 0.119 Uiso 1 1 calc R U . . .
H7B H 0.4404 0.7737 0.0407 0.119 Uiso 1 1 calc R U . . .
C8 C 0.4509(5) 0.8575(6) 0.1145(6) 0.134(3) Uani 1 1 d . . . . .
H8A H 0.4102 0.9343 0.0564 0.201 Uiso 1 1 calc R U . . .
H8B H 0.5251 0.8302 0.1192 0.201 Uiso 1 1 calc R U . . .
H8C H 0.4343 0.8609 0.1754 0.201 Uiso 1 1 calc R U . . .
C9 C 0.7792(3) 0.6376(5) 0.3703(3) 0.0679(14) Uani 1 1 d . . . . .
C10 C 0.7117(3) 0.6467(5) 0.5027(3) 0.0698(15) Uani 1 1 d . . . . .
C11 C 0.8599(3) 0.6464(4) 0.4924(3) 0.0657(14) Uani 1 1 d . . . . .
C12 C 0.8621(3) 0.6404(5) 0.4042(3) 0.0688(14) Uani 1 1 d . . . . .
C13 C 0.9972(4) 0.6426(5) 0.4417(4) 0.0796(16) Uani 1 1 d . . . . .
H13A H 1.0602 0.6440 0.4392 0.095 Uiso 1 1 calc R U . . .
C14 C 0.9810(4) 0.6540(5) 0.6008(3) 0.0725(15) Uani 1 1 d . . . . .
H14A H 1.0566 0.6251 0.6122 0.087 Uiso 1 1 calc R U . . .
H14B H 0.9689 0.6028 0.6608 0.087 Uiso 1 1 calc R U . . .
C15 C 0.9264(4) 0.7721(6) 0.5884(4) 0.100(2) Uani 1 1 d . . . . .
H15A H 0.9437 0.7681 0.6529 0.120 Uiso 1 1 calc R U . . .
H15B H 0.8504 0.8047 0.5696 0.120 Uiso 1 1 calc R U . . .
C16 C 0.9561(5) 0.8505(6) 0.5096(5) 0.126(2) Uani 1 1 d . . . . .
H16A H 0.9181 0.9272 0.5032 0.189 Uiso 1 1 calc R U . . .
H16B H 0.9385 0.8553 0.4454 0.189 Uiso 1 1 calc R U . . .
H16C H 1.0310 0.8198 0.5289 0.189 Uiso 1 1 calc R U . . .
C17 C 0.6559(4) 0.6483(5) -0.0704(3) 0.0732(15) Uani 1 1 d . . . . .
C18 C 0.7218(3) 0.6441(5) -0.2044(3) 0.0685(14) Uani 1 1 d . . . . .
C19 C 0.5752(3) 0.6409(4) -0.1944(3) 0.0667(14) Uani 1 1 d . . . . .
C20 C 0.5741(3) 0.6424(5) -0.1043(3) 0.0712(15) Uani 1 1 d . . . . .
C21 C 0.4405(4) 0.6371(5) -0.1399(4) 0.0836(17) Uani 1 1 d . . . . .
H21A H 0.3786 0.6333 -0.1365 0.100 Uiso 1 1 calc R U . . .
C22 C 0.4494(4) 0.6448(5) -0.3089(4) 0.0679(14) Uani 1 1 d . . . . .
H22A H 0.3997 0.6166 -0.2971 0.081 Uiso 1 1 calc R U . . .
H22B H 0.5084 0.5938 -0.3257 0.081 Uiso 1 1 calc R U . . .
C23 C 0.3975(4) 0.7630(6) -0.3945(4) 0.0914(19) Uani 1 1 d . . . . .
H23A H 0.3848 0.7597 -0.4563 0.110 Uiso 1 1 calc R U . . .
H23B H 0.4453 0.7934 -0.4016 0.110 Uiso 1 1 calc R U . . .
C24 C 0.2955(5) 0.8459(6) -0.3861(5) 0.132(3) Uani 1 1 d . . . . .
H24A H 0.2667 0.9219 -0.4452 0.197 Uiso 1 1 calc R U . . .
H24B H 0.3072 0.8513 -0.3260 0.197 Uiso 1 1 calc R U . . .
H24C H 0.2465 0.8182 -0.3816 0.197 Uiso 1 1 calc R U . . .
C25 C 0.1587(4) 0.6390(5) 0.8684(3) 0.0764(16) Uani 1 1 d . . . . .
C26 C 0.2239(3) 0.6393(5) 1.0040(3) 0.0677(14) Uani 1 1 d . . . . .
C27 C 0.0772(3) 0.6370(4) 0.9963(3) 0.0641(14) Uani 1 1 d . . . . .
C28 C 0.0772(3) 0.6365(5) 0.9061(3) 0.0700(14) Uani 1 1 d . . . . .
C29 C -0.0579(4) 0.6351(5) 0.9453(4) 0.0786(16) Uani 1 1 d . . . . .
H29A H -0.1211 0.6342 0.9441 0.094 Uiso 1 1 calc R U . . .
C30 C -0.0476(4) 0.6406(5) 1.1078(4) 0.0753(16) Uani 1 1 d . . . . .
H30A H 0.0118 0.5874 1.1674 0.090 Uiso 1 1 calc R U . . .
H30B H -0.0979 0.6133 1.1191 0.090 Uiso 1 1 calc R U . . .
C31 C -0.0975(4) 0.7555(6) 1.0989(4) 0.0941(19) Uani 1 1 d . . . . .
H31A H -0.0489 0.7850 1.0832 0.113 Uiso 1 1 calc R U . . .
H31B H -0.1106 0.7487 1.1642 0.113 Uiso 1 1 calc R U . . .
C32 C -0.2007(5) 0.8432(6) 1.0184(5) 0.127(2) Uani 1 1 d . . . . .
H32A H -0.2289 0.9175 1.0165 0.190 Uiso 1 1 calc R U . . .
H32B H -0.2503 0.8161 1.0344 0.190 Uiso 1 1 calc R U . . .
H32C H -0.1884 0.8518 0.9531 0.190 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26937(10) 0.62698(15) 0.54960(9) 0.0916(6) Uani 1 1 d . . . . .
Cl2 Cl 0.76666(10) 0.63034(15) 0.26226(10) 0.0917(6) Uani 1 1 d . . . . .
Cl3 Cl 0.66864(11) 0.65123(16) 0.03935(10) 0.1011(6) Uani 1 1 d . . . . .
Cl4 Cl 0.17326(11) 0.64052(17) 0.75654(10) 0.1064(6) Uani 1 1 d . . . . .
N1 N 0.2111(3) 0.6282(4) 0.3903(3) 0.0788(14) Uani 1 1 d . . . . .
N2 N 0.2951(3) 0.6379(4) 0.2531(3) 0.0704(12) Uani 1 1 d . . . . .
N3 N 0.1458(3) 0.6272(4) 0.2555(3) 0.0913(16) Uani 1 1 d . . . . .
H3A H 0.1473 0.6285 0.1975 0.110 Uiso 1 1 calc R U . . .
H3B H 0.0957 0.6230 0.2842 0.110 Uiso 1 1 calc R U . . .
N4 N 0.4489(3) 0.6427(4) 0.4285(3) 0.0753(12) Uani 1 1 d . . . . .
N5 N 0.4492(3) 0.6470(4) 0.2800(3) 0.0716(12) Uani 1 1 d . . . . .
N6 N 0.7035(3) 0.6426(4) 0.4167(3) 0.0735(12) Uani 1 1 d . . . . .
N7 N 0.7872(3) 0.6516(4) 0.5435(3) 0.0702(12) Uani 1 1 d . . . . .
N8 N 0.6343(3) 0.6507(4) 0.5478(3) 0.0864(14) Uani 1 1 d . . . . .
H8D H 0.6342 0.6563 0.6026 0.104 Uiso 1 1 calc R U . . .
H8E H 0.5834 0.6476 0.5226 0.104 Uiso 1 1 calc R U . . .
N9 N 0.9511(3) 0.6347(4) 0.3744(3) 0.0757(13) Uani 1 1 d . . . . .
N10 N 0.9473(3) 0.6488(4) 0.5156(3) 0.0723(12) Uani 1 1 d . . . . .
N11 N 0.7302(3) 0.6471(4) -0.1178(3) 0.0764(13) Uani 1 1 d . . . . .
N12 N 0.6451(3) 0.6423(4) -0.2484(3) 0.0687(12) Uani 1 1 d . . . . .
N13 N 0.7982(3) 0.6424(4) -0.2503(3) 0.0911(15) Uani 1 1 d . . . . .
H13B H 0.7968 0.6402 -0.3068 0.109 Uiso 1 1 calc R U . . .
H13C H 0.8500 0.6435 -0.2241 0.109 Uiso 1 1 calc R U . . .
N14 N 0.4881(3) 0.6411(4) -0.0713(3) 0.0818(14) Uani 1 1 d . . . . .
N15 N 0.4877(3) 0.6387(4) -0.2175(3) 0.0711(12) Uani 1 1 d . . . . .
N16 N 0.2327(3) 0.6403(4) 0.9162(3) 0.0801(13) Uani 1 1 d . . . . .
N17 N 0.1472(3) 0.6388(4) 1.0485(2) 0.0642(11) Uani 1 1 d . . . . .
N18 N 0.2998(3) 0.6411(4) 1.0493(3) 0.0855(14) Uani 1 1 d . . . . .
H18A H 0.2977 0.6418 1.1064 0.103 Uiso 1 1 calc R U . . .
H18B H 0.3515 0.6415 1.0218 0.103 Uiso 1 1 calc R U . . .
N19 N -0.0097(3) 0.6366(4) 0.8742(3) 0.0805(13) Uani 1 1 d . . . . .
N20 N -0.0104(3) 0.6351(4) 1.0218(3) 0.0704(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 N1 1.324(5) . ?
C1 C4 1.358(6) . ?
C1 Cl1 1.720(4) . ?
C2 N2 1.348(5) . ?
C2 N3 1.348(5) . ?
C2 N1 1.364(5) . ?
C3 N2 1.340(5) . ?
C3 N5 1.370(5) . ?
C3 C4 1.379(5) . ?
C4 N4 1.394(5) . ?
C5 N4 1.304(5) . ?
C5 N5 1.364(5) . ?
C6 N5 1.467(5) . ?
C6 C7 1.474(7) . ?
C7 C8 1.526(8) . ?
C9 N6 1.325(5) . ?
C9 C12 1.365(5) . ?
C9 Cl2 1.720(4) . ?
C10 N7 1.333(5) . ?
C10 N8 1.337(5) . ?
C10 N6 1.353(5) . ?
C11 N7 1.331(5) . ?
C11 N10 1.371(5) . ?
C11 C12 1.391(5) . ?
C12 N9 1.381(5) . ?
C13 N9 1.315(6) . ?
C13 N10 1.367(5) . ?
C14 N10 1.445(5) . ?
C14 C15 1.490(7) . ?
C15 C16 1.509(8) . ?
C17 N11 1.322(5) . ?
C17 C20 1.379(5) . ?
C17 Cl3 1.713(4) . ?
C18 N13 1.335(5) . ?
C18 N12 1.345(5) . ?
C18 N11 1.353(5) . ?
C19 N12 1.331(5) . ?
C19 N15 1.371(5) . ?
C19 C20 1.390(5) . ?
C20 N14 1.383(5) . ?
C21 N14 1.305(6) . ?
C21 N15 1.379(5) . ?
C22 N15 1.461(5) . ?
C22 C23 1.480(7) . ?
C23 C24 1.514(7) . ?
C25 N16 1.337(5) . ?
C25 C28 1.354(6) . ?
C25 Cl4 1.718(4) . ?
C26 N17 1.333(5) . ?
C26 N18 1.342(5) . ?
C26 N16 1.346(5) . ?
C27 N17 1.332(5) . ?
C27 N20 1.373(5) . ?
C27 C28 1.384(5) . ?
C28 N19 1.384(5) . ?
C29 N19 1.301(5) . ?
C29 N20 1.369(5) . ?
C30 N20 1.449(5) . ?
C30 C31 1.469(7) . ?
C31 C32 1.539(8) . ?

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
N1 C1 C4 122.7(4) . . ?
N1 C1 Cl1 115.2(3) . . ?
C4 C1 Cl1 122.1(3) . . ?
N2 C2 N3 117.4(4) . . ?
N2 C2 N1 127.3(4) . . ?
N3 C2 N1 115.3(4) . . ?
N2 C3 N5 125.6(4) . . ?
N2 C3 C4 128.0(4) . . ?
N5 C3 C4 106.4(3) . . ?
C1 C4 C3 114.7(3) . . ?
C1 C4 N4 135.2(4) . . ?
C3 C4 N4 110.1(4) . . ?
N4 C5 N5 114.7(4) . . ?
N5 C6 C7 113.0(5) . . ?
C6 C7 C8 114.2(5) . . ?
N6 C9 C12 122.6(4) . . ?
N6 C9 Cl2 116.2(3) . . ?
C12 C9 Cl2 121.1(3) . . ?
N7 C10 N8 117.9(3) . . ?
N7 C10 N6 126.0(3) . . ?
N8 C10 N6 116.0(4) . . ?
N7 C11 N10 126.3(4) . . ?
N7 C11 C12 127.6(4) . . ?
N10 C11 C12 106.1(3) . . ?
C9 C12 N9 135.8(4) . . ?
C9 C12 C11 113.5(3) . . ?
N9 C12 C11 110.7(3) . . ?
N9 C13 N10 114.7(4) . . ?
N10 C14 C15 113.2(4) . . ?
C14 C15 C16 112.1(5) . . ?
N11 C17 C20 122.4(4) . . ?
N11 C17 Cl3 116.6(3) . . ?
C20 C17 Cl3 120.9(3) . . ?
N13 C18 N12 117.0(4) . . ?
N13 C18 N11 116.2(4) . . ?
N12 C18 N11 126.8(4) . . ?
N12 C19 N15 126.6(4) . . ?
N12 C19 C20 128.1(4) . . ?
N15 C19 C20 105.3(3) . . ?
C17 C20 N14 135.1(4) . . ?
C17 C20 C19 113.5(3) . . ?
N14 C20 C19 111.3(3) . . ?
N14 C21 N15 114.2(4) . . ?
N15 C22 C23 112.4(4) . . ?
C22 C23 C24 114.7(5) . . ?
N16 C25 C28 121.9(4) . . ?
N16 C25 Cl4 116.0(3) . . ?
C28 C25 Cl4 122.1(3) . . ?
N17 C26 N18 117.8(4) . . ?
N17 C26 N16 126.4(4) . . ?
N18 C26 N16 115.8(4) . . ?
N17 C27 N20 126.5(3) . . ?
N17 C27 C28 127.6(4) . . ?
N20 C27 C28 105.9(3) . . ?
C25 C28 N19 134.9(4) . . ?
C25 C28 C27 114.4(3) . . ?
N19 C28 C27 110.7(4) . . ?
N19 C29 N20 114.8(4) . . ?
N20 C30 C31 114.6(4) . . ?
C30 C31 C32 114.2(5) . . ?
C1 N1 C2 116.6(3) . . ?
C3 N2 C2 110.7(3) . . ?
C5 N4 C4 103.5(3) . . ?
C5 N5 C3 105.3(3) . . ?
C5 N5 C6 127.4(4) . . ?
C3 N5 C6 127.3(3) . . ?
C9 N6 C10 117.7(3) . . ?
C11 N7 C10 112.3(3) . . ?
C13 N9 C12 103.3(4) . . ?
C13 N10 C11 105.2(3) . . ?
C13 N10 C14 127.2(4) . . ?
C11 N10 C14 127.6(3) . . ?
C17 N11 C18 117.5(3) . . ?
C19 N12 C18 111.5(3) . . ?
C21 N14 C20 103.5(4) . . ?
C19 N15 C21 105.7(3) . . ?
C19 N15 C22 126.7(3) . . ?
C21 N15 C22 127.5(4) . . ?
C25 N16 C26 117.8(3) . . ?
C27 N17 C26 112.0(3) . . ?
C29 N19 C28 103.4(4) . . ?
C29 N20 C27 105.1(3) . . ?
C29 N20 C30 127.9(4) . . ?
C27 N20 C30 126.8(3) . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.110

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.014 0.000 -0.001 917 137 ' '
_platon_squeeze_details          
;
;
_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_compound_source        6-Chloro-purin-2-amine
_chemical_properties_physical    
'Guests escape when exposed to air or dried, and crystals transform to other unknown phase'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ptGCl
_database_code_depnum_ccdc_archive 'CCDC 1417639'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT015_I                   
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF .... Please Do !
RESPONSE: The hkl part has been removed, and separately deposited as
a fcf file to CCDC.
;
_vrf_PLAT213_I                   
;
PROBLEM: Atom C10B has ADP max/min Ratio ..... 5.1 prolat
RESPONSE: Due to a large number of parameters (eight indepedent molecules
in an asymmetric unit) and large thermal motion of alkyl chains,
the thermal parameters of the alkyl C atoms were not able to be refined accurately.
;
_vrf_PLAT234_I                   
;
PROBLEM: Large Hirshfeld Difference C8B -- C9B .. 0.36 Ang.
RESPONSE: Due to a large number of parameters (eight indepedent molecules
in an asymmetric unit) and large thermal motion of alkyl chains,
the thermal parameters of the alkyl C atoms were not able to be refined accurately.
;

#============================================================================== 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        6-Chloro-9-penyl-purin-2-amine
_chemical_name_common            pt_GCl
_chemical_melting_point          none
_chemical_formula_moiety         'C10 H14 Cl N5'
_chemical_formula_sum            'C20 H28 Cl2 N10'
_chemical_formula_weight         479.42

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   15.078(3)
_cell_length_b                   15.132(3)
_cell_length_c                   21.864(4)
_cell_angle_alpha                81.61(3)
_cell_angle_beta                 80.08(3)
_cell_angle_gamma                89.95(3)
_cell_volume                     4860.0(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    325
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      22.3

_exptl_crystal_description       'square plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            39215
_diffrn_reflns_av_unetI/netI     0.2437
_diffrn_reflns_av_R_equivalents  0.1619
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.988
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             18927
_reflns_number_gt                6636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1528P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         18927
_refine_ls_number_parameters     1153
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.2303
_refine_ls_R_factor_gt           0.1411
_refine_ls_wR_factor_ref         0.3679
_refine_ls_wR_factor_gt          0.3251
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 1.16885(14) 0.36710(16) 0.42560(13) 0.0824(8) Uani 1 1 d . . . . .
N1A N 1.0056(4) 0.4222(4) 0.4320(3) 0.0561(18) Uani 1 1 d . . . . .
N2A N 0.8713(4) 0.3369(4) 0.4260(3) 0.0516(16) Uani 1 1 d . . . . .
N3A N 1.0562(4) 0.1869(4) 0.4145(3) 0.0597(18) Uani 1 1 d . . . . .
N4A N 0.9054(4) 0.1818(4) 0.4147(3) 0.0581(18) Uani 1 1 d . . . . .
N5A N 0.8643(5) 0.4855(5) 0.4402(4) 0.080(2) Uani 1 1 d . . . . .
H5A1 H 0.8074 0.4835 0.4397 0.096 Uiso 1 1 calc R U . . .
H5A2 H 0.8896 0.5344 0.4450 0.096 Uiso 1 1 calc R U . . .
C1A C 1.0562(5) 0.3522(5) 0.4268(4) 0.053(2) Uani 1 1 d . . . . .
C2A C 0.9142(5) 0.4115(5) 0.4334(4) 0.056(2) Uani 1 1 d . . . . .
C3A C 0.9273(4) 0.2689(5) 0.4213(4) 0.0456(18) Uani 1 1 d . . . . .
C4A C 1.0203(5) 0.2707(5) 0.4201(4) 0.0491(19) Uani 1 1 d . . . . .
C5A C 0.9845(6) 0.1381(6) 0.4117(4) 0.070(3) Uani 1 1 d . . . . .
H5A H 0.9881 0.0778 0.4079 0.084 Uiso 1 1 calc R U . . .
C6A C 0.8185(5) 0.1497(6) 0.4092(5) 0.071(3) Uani 1 1 d D . . . .
H6A1 H 0.7735 0.1719 0.4403 0.085 Uiso 1 1 calc R U . . .
H6A2 H 0.8165 0.0850 0.4184 0.085 Uiso 1 1 calc R U . . .
C7A C 0.7957(6) 0.1767(8) 0.3471(5) 0.094(4) Uani 1 1 d D . . . .
H7A1 H 0.7345 0.1565 0.3477 0.113 Uiso 1 1 calc R U . . .
H7A2 H 0.7973 0.2414 0.3384 0.113 Uiso 1 1 calc R U . . .
C8A C 0.8548(9) 0.1425(16) 0.2963(7) 0.200(11) Uani 1 1 d D . . . .
H8A1 H 0.9061 0.1839 0.2851 0.240 Uiso 1 1 calc R U . . .
H8A2 H 0.8772 0.0870 0.3156 0.240 Uiso 1 1 calc R U . . .
C9A C 0.8360(12) 0.1251(19) 0.2417(7) 0.277(18) Uani 1 1 d D . . . .
H9A1 H 0.8842 0.0894 0.2234 0.333 Uiso 1 1 calc R U . . .
H9A2 H 0.8379 0.1814 0.2139 0.333 Uiso 1 1 calc R U . . .
C10A C 0.7516(14) 0.0798(15) 0.2416(7) 0.235(14) Uani 1 1 d D . . . .
H10A H 0.7620 0.0335 0.2158 0.353 Uiso 1 1 calc R U . . .
H10B H 0.7107 0.1219 0.2253 0.353 Uiso 1 1 calc R U . . .
H10C H 0.7260 0.0540 0.2838 0.353 Uiso 1 1 calc R U . . .
Cl1B Cl -0.13052(14) 0.86692(17) 0.42597(13) 0.0823(8) Uani 1 1 d . . . . .
N1B N 0.0294(4) 0.9224(4) 0.4307(3) 0.0567(17) Uani 1 1 d . . . . .
N2B N 0.1665(4) 0.8364(4) 0.4259(3) 0.0513(16) Uani 1 1 d . . . . .
N3B N -0.0114(4) 0.6867(5) 0.4140(3) 0.0597(18) Uani 1 1 d . . . . .
N4B N 0.1383(4) 0.6834(4) 0.4134(3) 0.0608(18) Uani 1 1 d . . . . .
N5B N 0.1644(4) 0.9859(5) 0.4389(4) 0.072(2) Uani 1 1 d . . . . .
H5B1 H 0.1371 1.0354 0.4422 0.086 Uiso 1 1 calc R U . . .
H5B2 H 0.2210 0.9831 0.4401 0.086 Uiso 1 1 calc R U . . .
C1B C -0.0169(5) 0.8517(6) 0.4252(4) 0.057(2) Uani 1 1 d . . . . .
C2B C 0.1183(5) 0.9129(5) 0.4320(4) 0.055(2) Uani 1 1 d . . . . .
C3B C 0.1132(5) 0.7693(5) 0.4192(4) 0.0500(19) Uani 1 1 d . . . . .
C4B C 0.0215(5) 0.7702(5) 0.4200(4) 0.052(2) Uani 1 1 d . . . . .
C5B C 0.0607(6) 0.6383(6) 0.4101(4) 0.068(3) Uani 1 1 d . . . . .
H5B H 0.0595 0.5782 0.4054 0.081 Uiso 1 1 calc R U . . .
C6B C 0.2301(6) 0.6485(6) 0.4086(5) 0.078(3) Uani 1 1 d D . . . .
H6B1 H 0.2269 0.5837 0.4167 0.094 Uiso 1 1 calc R U . . .
H6B2 H 0.2596 0.6693 0.4401 0.094 Uiso 1 1 calc R U . . .
C7B C 0.2840(7) 0.6784(8) 0.3451(5) 0.100(4) Uani 1 1 d D . . . .
H7B1 H 0.3444 0.6560 0.3439 0.120 Uiso 1 1 calc R U . . .
H7B2 H 0.2884 0.7431 0.3380 0.120 Uiso 1 1 calc R U . . .
C8B C 0.2447(10) 0.6474(16) 0.2928(8) 0.204(11) Uani 1 1 d D . . . .
H8B1 H 0.1946 0.6069 0.3123 0.245 Uiso 1 1 calc R U . . .
H8B2 H 0.2195 0.6993 0.2710 0.245 Uiso 1 1 calc R U . . .
C9B C 0.2978(17) 0.605(2) 0.2466(9) 0.34(2) Uani 1 1 d D . . . .
H9B1 H 0.2995 0.6445 0.2074 0.408 Uiso 1 1 calc R U . . .
H9B2 H 0.2630 0.5522 0.2434 0.408 Uiso 1 1 calc R U . . .
C10B C 0.390(2) 0.575(2) 0.2466(13) 0.41(3) Uani 1 1 d D . . . .
H10D H 0.4234 0.6169 0.2635 0.622 Uiso 1 1 calc R U . . .
H10E H 0.4191 0.5707 0.2044 0.622 Uiso 1 1 calc R U . . .
H10F H 0.3895 0.5173 0.2719 0.622 Uiso 1 1 calc R U . . .
Cl1C Cl -0.10244(15) 0.58328(13) 0.08225(12) 0.0713(7) Uani 1 1 d . . . . .
N1C N -0.1595(4) 0.7449(4) 0.0769(3) 0.0528(17) Uani 1 1 d . . . . .
N2C N -0.0754(4) 0.8810(4) 0.0738(3) 0.0418(14) Uani 1 1 d . . . . .
N3C N 0.0818(4) 0.7010(4) 0.0815(3) 0.0562(17) Uani 1 1 d . . . . .
N4C N 0.0834(4) 0.8513(4) 0.0781(3) 0.0503(16) Uani 1 1 d . . . . .
N5C N -0.2242(4) 0.8834(4) 0.0731(3) 0.0641(19) Uani 1 1 d . . . . .
H5C1 H -0.2216 0.9405 0.0713 0.077 Uiso 1 1 calc R U . . .
H5C2 H -0.2748 0.8568 0.0737 0.077 Uiso 1 1 calc R U . . .
C1C C -0.0870(5) 0.6973(5) 0.0795(4) 0.0484(19) Uani 1 1 d . . . . .
C2C C -0.1499(5) 0.8360(5) 0.0749(4) 0.0494(19) Uani 1 1 d . . . . .
C3C C -0.0013(4) 0.8278(4) 0.0774(3) 0.0423(17) Uani 1 1 d . . . . .
C4C C -0.0030(4) 0.7345(5) 0.0785(4) 0.0445(18) Uani 1 1 d . . . . .
C5C C 0.1295(5) 0.7736(5) 0.0817(4) 0.053(2) Uani 1 1 d . . . . .
H5C H 0.1905 0.7721 0.0840 0.064 Uiso 1 1 calc R U . . .
C6C C 0.1175(5) 0.9408(5) 0.0812(4) 0.055(2) Uani 1 1 d D . . . .
H6C1 H 0.0929 0.9839 0.0516 0.066 Uiso 1 1 calc R U . . .
H6C2 H 0.1825 0.9429 0.0688 0.066 Uiso 1 1 calc R U . . .
C7C C 0.0935(6) 0.9673(6) 0.1463(4) 0.063(2) Uani 1 1 d D . . . .
H7C1 H 0.0288 0.9615 0.1599 0.076 Uiso 1 1 calc R U . . .
H7C2 H 0.1108 1.0295 0.1444 0.076 Uiso 1 1 calc R U . . .
C8C C 0.1402(7) 0.9095(7) 0.1954(4) 0.087(3) Uani 1 1 d D . . . .
H8C1 H 0.1222 0.8474 0.1979 0.105 Uiso 1 1 calc R U . . .
H8C2 H 0.2049 0.9145 0.1815 0.105 Uiso 1 1 calc R U . . .
C9C C 0.1170(10) 0.9374(9) 0.2610(5) 0.121(5) Uani 1 1 d D . . . .
H9C1 H 0.0524 0.9319 0.2752 0.145 Uiso 1 1 calc R U . . .
H9C2 H 0.1457 0.8976 0.2903 0.145 Uiso 1 1 calc R U . . .
C10C C 0.1484(13) 1.0337(11) 0.2602(7) 0.189(10) Uani 1 1 d D . . . .
H10G H 0.1620 1.0632 0.2176 0.284 Uiso 1 1 calc R U . . .
H10H H 0.2014 1.0336 0.2790 0.284 Uiso 1 1 calc R U . . .
H10I H 0.1016 1.0646 0.2835 0.284 Uiso 1 1 calc R U . . .
Cl1D Cl 0.39731(14) 0.88168(13) 0.08274(12) 0.0709(7) Uani 1 1 d . . . . .
N1D N 0.3403(4) 0.7229(4) 0.0773(3) 0.0498(16) Uani 1 1 d . . . . .
N2D N 0.4250(4) 0.5870(4) 0.0745(3) 0.0453(15) Uani 1 1 d . . . . .
N3D N 0.5830(4) 0.7644(4) 0.0814(3) 0.0551(17) Uani 1 1 d . . . . .
N4D N 0.5852(4) 0.6161(4) 0.0776(3) 0.0519(16) Uani 1 1 d . . . . .
N5D N 0.2737(4) 0.5867(4) 0.0729(3) 0.065(2) Uani 1 1 d . . . . .
H5D1 H 0.2752 0.5300 0.0723 0.078 Uiso 1 1 calc R U . . .
H5D2 H 0.2237 0.6140 0.0726 0.078 Uiso 1 1 calc R U . . .
C1D C 0.4122(5) 0.7687(5) 0.0781(4) 0.052(2) Uani 1 1 d . . . . .
C2D C 0.3500(5) 0.6329(5) 0.0741(4) 0.052(2) Uani 1 1 d . . . . .
C3D C 0.4974(5) 0.6406(5) 0.0758(4) 0.0471(18) Uani 1 1 d . . . . .
C4D C 0.4964(5) 0.7334(5) 0.0789(3) 0.0466(18) Uani 1 1 d . . . . .
C5D C 0.6298(5) 0.6927(5) 0.0806(4) 0.056(2) Uani 1 1 d . . . . .
H5D H 0.6911 0.6937 0.0821 0.067 Uiso 1 1 calc R U . . .
C6D C 0.6190(5) 0.5256(5) 0.0798(4) 0.0512(19) Uani 1 1 d D . . . .
H6D1 H 0.6840 0.5284 0.0671 0.061 Uiso 1 1 calc R U . . .
H6D2 H 0.5938 0.4954 0.0503 0.061 Uiso 1 1 calc R U . . .
C7D C 0.5954(5) 0.4726(5) 0.1445(3) 0.059(2) Uani 1 1 d D . . . .
H7D1 H 0.5305 0.4720 0.1574 0.071 Uiso 1 1 calc R U . . .
H7D2 H 0.6132 0.4114 0.1424 0.071 Uiso 1 1 calc R U . . .
C8D C 0.6380(8) 0.5070(8) 0.1933(5) 0.092(3) Uani 1 1 d D . . . .
H8D1 H 0.6181 0.5672 0.1971 0.110 Uiso 1 1 calc R U . . .
H8D2 H 0.7028 0.5098 0.1800 0.110 Uiso 1 1 calc R U . . .
C9D C 0.6157(11) 0.4499(10) 0.2568(5) 0.124(5) Uani 1 1 d D . . . .
H9D1 H 0.6398 0.4791 0.2872 0.149 Uiso 1 1 calc R U . . .
H9D2 H 0.5508 0.4454 0.2694 0.149 Uiso 1 1 calc R U . . .
C10D C 0.6523(16) 0.3572(13) 0.2580(7) 0.226(12) Uani 1 1 d D . . . .
H10J H 0.6483 0.3362 0.2192 0.339 Uiso 1 1 calc R U . . .
H10K H 0.6177 0.3179 0.2922 0.339 Uiso 1 1 calc R U . . .
H10L H 0.7141 0.3584 0.2634 0.339 Uiso 1 1 calc R U . . .
Cl1E Cl 0.67269(13) -0.04827(14) 0.41703(12) 0.0679(6) Uani 1 1 d . . . . .
N1E N 0.5068(4) -0.1062(4) 0.4265(3) 0.0493(15) Uani 1 1 d . . . . .
N2E N 0.3746(4) -0.0180(4) 0.4272(3) 0.0484(15) Uani 1 1 d . . . . .
N3E N 0.5584(4) 0.1363(4) 0.4147(3) 0.0594(18) Uani 1 1 d . . . . .
N4E N 0.4073(4) 0.1392(4) 0.4194(3) 0.0564(17) Uani 1 1 d . . . . .
N5E N 0.3679(4) -0.1710(4) 0.4347(3) 0.0602(18) Uani 1 1 d . . . . .
H5E1 H 0.3932 -0.2220 0.4360 0.072 Uiso 1 1 calc R U . . .
H5E2 H 0.3105 -0.1680 0.4368 0.072 Uiso 1 1 calc R U . . .
C1E C 0.5570(5) -0.0330(5) 0.4210(4) 0.0478(18) Uani 1 1 d . . . . .
C2E C 0.4181(5) -0.0958(5) 0.4295(4) 0.0470(18) Uani 1 1 d . . . . .
C3E C 0.4299(5) 0.0514(5) 0.4225(4) 0.0489(19) Uani 1 1 d . . . . .
C4E C 0.5228(5) 0.0505(5) 0.4194(4) 0.0486(19) Uani 1 1 d . . . . .
C5E C 0.4845(6) 0.1865(6) 0.4149(4) 0.068(3) Uani 1 1 d . . . . .
H5E H 0.4866 0.2484 0.4121 0.082 Uiso 1 1 calc R U . . .
C6E C 0.3200(5) 0.1756(6) 0.4171(5) 0.069(3) Uani 1 1 d D . . . .
H6E1 H 0.3195 0.2356 0.4278 0.083 Uiso 1 1 calc R U . . .
H6E2 H 0.2757 0.1395 0.4482 0.083 Uiso 1 1 calc R U . . .
C7E C 0.2942(7) 0.1785(7) 0.3537(5) 0.088(3) Uani 1 1 d D . . . .
H7E1 H 0.2947 0.1183 0.3433 0.106 Uiso 1 1 calc R U . . .
H7E2 H 0.2332 0.1996 0.3556 0.106 Uiso 1 1 calc R U . . .
C8E C 0.3548(10) 0.2372(11) 0.3026(6) 0.151(7) Uani 1 1 d D . . . .
H8E1 H 0.3647 0.2926 0.3181 0.181 Uiso 1 1 calc R U . . .
H8E2 H 0.4126 0.2085 0.2960 0.181 Uiso 1 1 calc R U . . .
C9E C 0.3290(12) 0.2597(15) 0.2433(7) 0.174(8) Uani 1 1 d D . . . .
H9E1 H 0.3237 0.2052 0.2256 0.209 Uiso 1 1 calc R U . . .
H9E2 H 0.3768 0.2964 0.2158 0.209 Uiso 1 1 calc R U . . .
C10E C 0.2453(15) 0.3070(17) 0.2432(7) 0.230(12) Uani 1 1 d D . . . .
H10M H 0.2045 0.2870 0.2815 0.346 Uiso 1 1 calc R U . . .
H10N H 0.2189 0.2952 0.2081 0.346 Uiso 1 1 calc R U . . .
H10O H 0.2571 0.3700 0.2398 0.346 Uiso 1 1 calc R U . . .
Cl1F Cl 0.37012(13) 0.45190(14) 0.41794(12) 0.0694(7) Uani 1 1 d . . . . .
N1F N 0.5314(4) 0.3936(4) 0.4274(3) 0.0509(16) Uani 1 1 d . . . . .
N2F N 0.6642(4) 0.4816(4) 0.4261(3) 0.0494(16) Uani 1 1 d . . . . .
N3F N 0.4862(4) 0.6365(4) 0.4145(3) 0.0595(18) Uani 1 1 d . . . . .
N4F N 0.6333(4) 0.6414(4) 0.4177(3) 0.0585(18) Uani 1 1 d . . . . .
N5F N 0.6658(4) 0.3302(4) 0.4349(3) 0.0573(17) Uani 1 1 d . . . . .
H5F1 H 0.7220 0.3327 0.4375 0.069 Uiso 1 1 calc R U . . .
H5F2 H 0.6393 0.2794 0.4365 0.069 Uiso 1 1 calc R U . . .
C1F C 0.4829(5) 0.4656(6) 0.4220(4) 0.052(2) Uani 1 1 d . . . . .
C2F C 0.6192(5) 0.4061(5) 0.4282(4) 0.0473(18) Uani 1 1 d . . . . .
C3F C 0.6105(5) 0.5522(5) 0.4207(4) 0.0473(18) Uani 1 1 d . . . . .
C4F C 0.5194(5) 0.5505(5) 0.4193(4) 0.0464(18) Uani 1 1 d . . . . .
C5F C 0.5573(6) 0.6880(6) 0.4138(4) 0.068(2) Uani 1 1 d . . . . .
H5F H 0.5552 0.7498 0.4110 0.081 Uiso 1 1 calc R U . . .
C6F C 0.7254(6) 0.6756(6) 0.4152(5) 0.075(3) Uani 1 1 d D . . . .
H6F1 H 0.7534 0.6385 0.4462 0.090 Uiso 1 1 calc R U . . .
H6F2 H 0.7229 0.7359 0.4256 0.090 Uiso 1 1 calc R U . . .
C7F C 0.7810(6) 0.6763(7) 0.3521(5) 0.089(3) Uani 1 1 d D . . . .
H7F1 H 0.7852 0.6156 0.3428 0.107 Uiso 1 1 calc R U . . .
H7F2 H 0.8414 0.6976 0.3529 0.107 Uiso 1 1 calc R U . . .
C8F C 0.7446(10) 0.7336(14) 0.3007(7) 0.186(9) Uani 1 1 d D . . . .
H8F1 H 0.6957 0.7000 0.2906 0.223 Uiso 1 1 calc R U . . .
H8F2 H 0.7183 0.7851 0.3179 0.223 Uiso 1 1 calc R U . . .
C9F C 0.8019(13) 0.7656(18) 0.2437(8) 0.235(12) Uani 1 1 d D . . . .
H9F1 H 0.7688 0.8085 0.2194 0.282 Uiso 1 1 calc R U . . .
H9F2 H 0.8147 0.7159 0.2204 0.282 Uiso 1 1 calc R U . . .
C10F C 0.8906(17) 0.8094(18) 0.2471(8) 0.31(2) Uani 1 1 d D . . . .
H10P H 0.8833 0.8727 0.2454 0.461 Uiso 1 1 calc R U . . .
H10Q H 0.9350 0.7979 0.2122 0.461 Uiso 1 1 calc R U . . .
H10R H 0.9097 0.7854 0.2856 0.461 Uiso 1 1 calc R U . . .
Cl1G Cl 0.18838(14) 0.61804(13) 0.92250(12) 0.0718(7) Uani 1 1 d . . . . .
N1G N 0.1300(4) 0.7796(4) 0.9243(3) 0.0487(16) Uani 1 1 d . . . . .
N2G N 0.2169(4) 0.9134(4) 0.9264(3) 0.0425(14) Uani 1 1 d . . . . .
N3G N 0.3741(4) 0.7339(4) 0.9220(3) 0.0525(16) Uani 1 1 d . . . . .
N4G N 0.3765(4) 0.8826(4) 0.9239(3) 0.0512(16) Uani 1 1 d . . . . .
N5G N 0.0653(4) 0.9171(4) 0.9257(3) 0.0574(18) Uani 1 1 d . . . . .
H5G1 H 0.0682 0.9740 0.9252 0.069 Uiso 1 1 calc R U . . .
H5G2 H 0.0145 0.8913 0.9257 0.069 Uiso 1 1 calc R U . . .
C1G C 0.2051(5) 0.7302(5) 0.9256(4) 0.051(2) Uani 1 1 d . . . . .
C2G C 0.1416(5) 0.8677(5) 0.9265(3) 0.0460(18) Uani 1 1 d . . . . .
C3G C 0.2884(5) 0.8597(5) 0.9258(4) 0.0477(19) Uani 1 1 d . . . . .
C4G C 0.2860(4) 0.7669(5) 0.9246(4) 0.0462(18) Uani 1 1 d . . . . .
C5G C 0.4251(5) 0.8047(6) 0.9222(4) 0.062(2) Uani 1 1 d . . . . .
H5G H 0.4869 0.8026 0.9213 0.074 Uiso 1 1 calc R U . . .
C6G C 0.4153(5) 0.9733(5) 0.9201(4) 0.052(2) Uani 1 1 d D . . . .
H6G1 H 0.4750 0.9690 0.9309 0.062 Uiso 1 1 calc R U . . .
H6G2 H 0.3781 1.0052 0.9501 0.062 Uiso 1 1 calc R U . . .
C7G C 0.4209(6) 1.0245(5) 0.8547(4) 0.064(2) Uani 1 1 d D . . . .
H7G1 H 0.3617 1.0240 0.8430 0.077 Uiso 1 1 calc R U . . .
H7G2 H 0.4377 1.0862 0.8553 0.077 Uiso 1 1 calc R U . . .
C8G C 0.4874(8) 0.9880(8) 0.8051(5) 0.105(4) Uani 1 1 d D . . . .
H8G1 H 0.5457 0.9842 0.8182 0.125 Uiso 1 1 calc R U . . .
H8G2 H 0.4681 0.9278 0.8021 0.125 Uiso 1 1 calc R U . . .
C9G C 0.4977(11) 1.0432(9) 0.7413(5) 0.151(8) Uani 1 1 d D . . . .
H9G1 H 0.4388 1.0525 0.7297 0.181 Uiso 1 1 calc R U . . .
H9G2 H 0.5332 1.0111 0.7107 0.181 Uiso 1 1 calc R U . . .
C10G C 0.5426(15) 1.1322(12) 0.7401(7) 0.212(12) Uani 1 1 d D . . . .
H10S H 0.5360 1.1463 0.7820 0.318 Uiso 1 1 calc R U . . .
H10T H 0.5151 1.1775 0.7145 0.318 Uiso 1 1 calc R U . . .
H10U H 0.6054 1.1298 0.7229 0.318 Uiso 1 1 calc R U . . .
Cl1H Cl 0.31109(14) 0.08515(13) 0.07819(12) 0.0711(7) Uani 1 1 d . . . . .
N1H N 0.3693(4) 0.2470(4) 0.0760(3) 0.0476(15) Uani 1 1 d . . . . .
N2H N 0.2824(4) 0.3823(4) 0.0738(3) 0.0450(15) Uani 1 1 d . . . . .
N3H N 0.1259(4) 0.1995(4) 0.0788(3) 0.0579(18) Uani 1 1 d . . . . .
N4H N 0.1242(4) 0.3508(4) 0.0774(3) 0.0492(16) Uani 1 1 d . . . . .
N5H N 0.4330(4) 0.3852(4) 0.0754(3) 0.0597(18) Uani 1 1 d . . . . .
H5H1 H 0.4304 0.4422 0.0742 0.072 Uiso 1 1 calc R U . . .
H5H2 H 0.4835 0.3591 0.0766 0.072 Uiso 1 1 calc R U . . .
C1H C 0.2960(5) 0.1983(5) 0.0764(4) 0.053(2) Uani 1 1 d . . . . .
C2H C 0.3592(5) 0.3377(5) 0.0756(4) 0.0488(19) Uani 1 1 d . . . . .
C3H C 0.2111(4) 0.3268(5) 0.0752(4) 0.0461(18) Uani 1 1 d . . . . .
C4H C 0.2117(5) 0.2340(5) 0.0755(4) 0.0487(19) Uani 1 1 d . . . . .
C5H C 0.0762(5) 0.2712(5) 0.0778(4) 0.060(2) Uani 1 1 d . . . . .
H5H H 0.0146 0.2692 0.0775 0.072 Uiso 1 1 calc R U . . .
C6H C 0.0858(5) 0.4384(5) 0.0826(4) 0.056(2) Uani 1 1 d D . . . .
H6H1 H 0.0260 0.4388 0.0718 0.068 Uiso 1 1 calc R U . . .
H6H2 H 0.1226 0.4831 0.0526 0.068 Uiso 1 1 calc R U . . .
C7H C 0.0795(6) 0.4634(6) 0.1473(4) 0.063(2) Uani 1 1 d D . . . .
H7H1 H 0.0628 0.5255 0.1461 0.076 Uiso 1 1 calc R U . . .
H7H2 H 0.1383 0.4577 0.1596 0.076 Uiso 1 1 calc R U . . .
C8H C 0.0115(8) 0.4058(8) 0.1960(4) 0.095(3) Uani 1 1 d D . . . .
H8H1 H -0.0461 0.4085 0.1818 0.114 Uiso 1 1 calc R U . . .
H8H2 H 0.0304 0.3443 0.1984 0.114 Uiso 1 1 calc R U . . .
C9H C -0.0016(10) 0.4313(10) 0.2607(5) 0.121(5) Uani 1 1 d D . . . .
H9H1 H 0.0550 0.4244 0.2762 0.145 Uiso 1 1 calc R U . . .
H9H2 H -0.0454 0.3902 0.2883 0.145 Uiso 1 1 calc R U . . .
C10H C -0.0327(14) 0.5256(12) 0.2644(7) 0.190(9) Uani 1 1 d D . . . .
H10V H 0.0102 0.5670 0.2374 0.286 Uiso 1 1 calc R U . . .
H10W H -0.0381 0.5373 0.3069 0.286 Uiso 1 1 calc R U . . .
H10$ H -0.0902 0.5324 0.2513 0.286 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cl1A C1A 1.709(7) . ?
N1A C1A 1.312(10) . ?
N1A C2A 1.382(9) . ?
N2A C3A 1.334(9) . ?
N2A C2A 1.346(8) . ?
N3A C5A 1.325(9) . ?
N3A C4A 1.391(9) . ?
N4A C5A 1.360(11) . ?
N4A C3A 1.393(8) . ?
N4A C6A 1.428(9) . ?
N5A C2A 1.362(10) . ?
C1A C4A 1.385(9) . ?
C3A C4A 1.398(9) . ?
C6A C7A 1.459(11) . ?
C7A C8A 1.457(12) . ?
C8A C9A 1.336(12) . ?
C9A C10A 1.447(13) . ?
Cl1B C1B 1.727(8) . ?
N1B C1B 1.309(8) . ?
N1B C2B 1.354(10) . ?
N2B C3B 1.335(8) . ?
N2B C2B 1.378(10) . ?
N3B C5B 1.308(11) . ?
N3B C4B 1.390(8) . ?
N4B C3B 1.371(9) . ?
N4B C5B 1.373(9) . ?
N4B C6B 1.473(11) . ?
N5B C2B 1.346(8) . ?
C1B C4B 1.372(11) . ?
C3B C4B 1.380(10) . ?
C6B C7B 1.491(11) . ?
C7B C8B 1.506(12) . ?
C8B C9B 1.409(15) . ?
C9B C10B 1.469(17) . ?
Cl1C C1C 1.732(7) . ?
N1C C1C 1.313(10) . ?
N1C C2C 1.380(9) . ?
N2C C2C 1.309(8) . ?
N2C C3C 1.382(9) . ?
N3C C5C 1.313(8) . ?
N3C C4C 1.385(9) . ?
N4C C3C 1.329(8) . ?
N4C C5C 1.365(10) . ?
N4C C6C 1.464(8) . ?
N5C C2C 1.333(10) . ?
C1C C4C 1.382(9) . ?
C3C C4C 1.410(9) . ?
C6C C7C 1.519(9) . ?
C7C C8C 1.547(11) . ?
C8C C9C 1.537(11) . ?
C9C C10C 1.530(13) . ?
Cl1D C1D 1.740(8) . ?
N1D C1D 1.292(8) . ?
N1D C2D 1.380(9) . ?
N2D C2D 1.328(10) . ?
N2D C3D 1.368(8) . ?
N3D C5D 1.294(10) . ?
N3D C4D 1.400(8) . ?
N4D C5D 1.357(8) . ?
N4D C3D 1.381(9) . ?
N4D C6D 1.457(9) . ?
N5D C2D 1.352(8) . ?
C1D C4D 1.378(11) . ?
C3D C4D 1.416(9) . ?
C6D C7D 1.505(9) . ?
C7D C8D 1.492(9) . ?
C8D C9D 1.508(11) . ?
C9D C10D 1.505(13) . ?
Cl1E C1E 1.748(8) . ?
N1E C1E 1.320(8) . ?
N1E C2E 1.338(9) . ?
N2E C3E 1.321(8) . ?
N2E C2E 1.346(9) . ?
N3E C5E 1.348(11) . ?
N3E C4E 1.390(8) . ?
N4E C5E 1.349(9) . ?
N4E C3E 1.367(10) . ?
N4E C6E 1.432(10) . ?
N5E C2E 1.348(8) . ?
C1E C4E 1.363(10) . ?
C3E C4E 1.391(10) . ?
C6E C7E 1.498(11) . ?
C7E C8E 1.494(11) . ?
C8E C9E 1.412(13) . ?
C9E C10E 1.451(14) . ?
Cl1F C1F 1.732(8) . ?
N1F C1F 1.315(10) . ?
N1F C2F 1.340(9) . ?
N2F C2F 1.321(8) . ?
N2F C3F 1.345(9) . ?
N3F C5F 1.322(9) . ?
N3F C4F 1.390(9) . ?
N4F C5F 1.354(11) . ?
N4F C3F 1.383(8) . ?
N4F C6F 1.472(9) . ?
N5F C2F 1.348(10) . ?
C1F C4F 1.387(9) . ?
C3F C4F 1.379(9) . ?
C6F C7F 1.484(11) . ?
C7F C8F 1.498(13) . ?
C8F C9F 1.411(13) . ?
C9F C10F 1.511(14) . ?
Cl1G C1G 1.728(7) . ?
N1G C2G 1.353(8) . ?
N1G C1G 1.359(10) . ?
N2G C2G 1.329(8) . ?
N2G C3G 1.349(9) . ?
N3G C5G 1.320(9) . ?
N3G C4G 1.413(9) . ?
N4G C3G 1.365(8) . ?
N4G C5G 1.389(10) . ?
N4G C6G 1.479(8) . ?
N5G C2G 1.373(10) . ?
C1G C4G 1.336(9) . ?
C3G C4G 1.408(9) . ?
C6G C7G 1.513(10) . ?
C7G C8G 1.512(11) . ?
C8G C9G 1.500(12) . ?
C9G C10G 1.503(12) . ?
Cl1H C1H 1.722(8) . ?
N1H C1H 1.327(8) . ?
N1H C2H 1.380(9) . ?
N2H C2H 1.343(10) . ?
N2H C3H 1.358(7) . ?
N3H C5H 1.317(10) . ?
N3H C4H 1.382(8) . ?
N4H C3H 1.354(9) . ?
N4H C5H 1.403(8) . ?
N4H C6H 1.458(9) . ?
N5H C2H 1.324(8) . ?
C1H C4H 1.383(11) . ?
C3H C4H 1.404(10) . ?
C6H C7H 1.503(9) . ?
C7H C8H 1.517(10) . ?
C8H C9H 1.502(11) . ?
C9H C10H 1.511(13) . ?

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
C1A N1A C2A 118.0(6) . . ?
C3A N2A C2A 111.5(6) . . ?
C5A N3A C4A 102.5(7) . . ?
C5A N4A C3A 104.9(6) . . ?
C5A N4A C6A 129.2(7) . . ?
C3A N4A C6A 125.9(7) . . ?
N1A C1A C4A 121.4(7) . . ?
N1A C1A Cl1A 117.1(5) . . ?
C4A C1A Cl1A 121.5(7) . . ?
N2A C2A N5A 117.5(7) . . ?
N2A C2A N1A 126.5(7) . . ?
N5A C2A N1A 115.9(6) . . ?
N2A C3A N4A 126.9(6) . . ?
N2A C3A C4A 127.4(6) . . ?
N4A C3A C4A 105.6(6) . . ?
C1A C4A N3A 133.8(7) . . ?
C1A C4A C3A 115.0(7) . . ?
N3A C4A C3A 111.2(6) . . ?
N3A C5A N4A 115.8(8) . . ?
N4A C6A C7A 113.1(7) . . ?
C8A C7A C6A 114.6(12) . . ?
C9A C8A C7A 128.6(15) . . ?
C8A C9A C10A 118.6(14) . . ?
C1B N1B C2B 117.5(7) . . ?
C3B N2B C2B 110.9(6) . . ?
C5B N3B C4B 103.0(6) . . ?
C3B N4B C5B 105.4(7) . . ?
C3B N4B C6B 127.0(6) . . ?
C5B N4B C6B 127.5(7) . . ?
N1B C1B C4B 122.7(7) . . ?
N1B C1B Cl1B 115.5(7) . . ?
C4B C1B Cl1B 121.8(5) . . ?
N5B C2B N1B 116.7(7) . . ?
N5B C2B N2B 116.9(7) . . ?
N1B C2B N2B 126.4(6) . . ?
N2B C3B N4B 126.5(7) . . ?
N2B C3B C4B 127.6(7) . . ?
N4B C3B C4B 105.8(6) . . ?
C1B C4B C3B 114.8(6) . . ?
C1B C4B N3B 134.0(7) . . ?
C3B C4B N3B 111.2(7) . . ?
N3B C5B N4B 114.5(7) . . ?
N4B C6B C7B 110.9(8) . . ?
C6B C7B C8B 113.5(11) . . ?
C9B C8B C7B 121.4(13) . . ?
C8B C9B C10B 126.6(16) . . ?
C1C N1C C2C 117.2(6) . . ?
C2C N2C C3C 113.6(6) . . ?
C5C N3C C4C 102.2(7) . . ?
C3C N4C C5C 105.7(5) . . ?
C3C N4C C6C 126.8(7) . . ?
C5C N4C C6C 127.3(6) . . ?
N1C C1C C4C 123.1(7) . . ?
N1C C1C Cl1C 115.6(5) . . ?
C4C C1C Cl1C 121.3(6) . . ?
N2C C2C N5C 116.6(7) . . ?
N2C C2C N1C 126.9(7) . . ?
N5C C2C N1C 116.5(6) . . ?
N4C C3C N2C 129.3(6) . . ?
N4C C3C C4C 106.5(6) . . ?
N2C C3C C4C 124.1(6) . . ?
C1C C4C N3C 135.0(7) . . ?
C1C C4C C3C 114.8(7) . . ?
N3C C4C C3C 110.1(5) . . ?
N3C C5C N4C 115.4(7) . . ?
N4C C6C C7C 112.7(6) . . ?
C6C C7C C8C 112.8(8) . . ?
C9C C8C C7C 112.7(10) . . ?
C10C C9C C8C 111.1(10) . . ?
C1D N1D C2D 117.1(7) . . ?
C2D N2D C3D 111.9(6) . . ?
C5D N3D C4D 102.9(6) . . ?
C5D N4D C3D 105.0(6) . . ?
C5D N4D C6D 128.7(7) . . ?
C3D N4D C6D 126.2(5) . . ?
N1D C1D C4D 124.8(7) . . ?
N1D C1D Cl1D 115.8(6) . . ?
C4D C1D Cl1D 119.3(5) . . ?
N2D C2D N5D 117.2(7) . . ?
N2D C2D N1D 126.9(6) . . ?
N5D C2D N1D 115.8(7) . . ?
N2D C3D N4D 128.0(6) . . ?
N2D C3D C4D 126.5(7) . . ?
N4D C3D C4D 105.4(5) . . ?
C1D C4D N3D 137.4(7) . . ?
C1D C4D C3D 112.7(6) . . ?
N3D C4D C3D 109.9(7) . . ?
N3D C5D N4D 116.8(7) . . ?
N4D C6D C7D 111.9(6) . . ?
C8D C7D C6D 114.6(7) . . ?
C7D C8D C9D 113.0(9) . . ?
C10D C9D C8D 113.6(12) . . ?
C1E N1E C2E 117.0(7) . . ?
C3E N2E C2E 112.2(6) . . ?
C5E N3E C4E 102.2(6) . . ?
C5E N4E C3E 106.7(7) . . ?
C5E N4E C6E 126.0(7) . . ?
C3E N4E C6E 127.2(6) . . ?
N1E C1E C4E 123.4(7) . . ?
N1E C1E Cl1E 116.2(6) . . ?
C4E C1E Cl1E 120.4(5) . . ?
N1E C2E N2E 126.5(6) . . ?
N1E C2E N5E 116.3(7) . . ?
N2E C2E N5E 117.1(6) . . ?
N2E C3E N4E 126.9(7) . . ?
N2E C3E C4E 127.4(7) . . ?
N4E C3E C4E 105.7(6) . . ?
C1E C4E N3E 135.4(7) . . ?
C1E C4E C3E 113.3(6) . . ?
N3E C4E C3E 111.3(7) . . ?
N3E C5E N4E 114.2(8) . . ?
N4E C6E C7E 112.2(8) . . ?
C8E C7E C6E 113.8(9) . . ?
C9E C8E C7E 119.6(14) . . ?
C8E C9E C10E 115.6(15) . . ?
C1F N1F C2F 116.7(6) . . ?
C2F N2F C3F 111.2(6) . . ?
C5F N3F C4F 104.1(7) . . ?
C5F N4F C3F 106.9(6) . . ?
C5F N4F C6F 128.6(7) . . ?
C3F N4F C6F 124.3(7) . . ?
N1F C1F C4F 122.1(7) . . ?
N1F C1F Cl1F 117.8(5) . . ?
C4F C1F Cl1F 120.1(7) . . ?
N2F C2F N1F 128.8(8) . . ?
N2F C2F N5F 116.6(7) . . ?
N1F C2F N5F 114.5(6) . . ?
N2F C3F C4F 127.0(6) . . ?
N2F C3F N4F 127.8(6) . . ?
C4F C3F N4F 105.2(6) . . ?
C3F C4F C1F 114.2(7) . . ?
C3F C4F N3F 110.7(5) . . ?
C1F C4F N3F 135.1(7) . . ?
N3F C5F N4F 113.1(7) . . ?
N4F C6F C7F 111.6(7) . . ?
C6F C7F C8F 113.6(12) . . ?
C9F C8F C7F 120.2(15) . . ?
C8F C9F C10F 117.8(15) . . ?
C2G N1G C1G 115.3(6) . . ?
C2G N2G C3G 111.5(6) . . ?
C5G N3G C4G 104.7(6) . . ?
C3G N4G C5G 107.1(6) . . ?
C3G N4G C6G 127.3(7) . . ?
C5G N4G C6G 125.5(6) . . ?
C4G C1G N1G 122.3(7) . . ?
C4G C1G Cl1G 123.2(7) . . ?
N1G C1G Cl1G 114.3(5) . . ?
N2G C2G N1G 129.1(7) . . ?
N2G C2G N5G 115.8(6) . . ?
N1G C2G N5G 115.0(6) . . ?
N2G C3G N4G 128.4(6) . . ?
N2G C3G C4G 125.4(6) . . ?
N4G C3G C4G 106.1(6) . . ?
C1G C4G C3G 116.1(7) . . ?
C1G C4G N3G 134.5(7) . . ?
C3G C4G N3G 109.4(5) . . ?
N3G C5G N4G 112.8(7) . . ?
N4G C6G C7G 110.7(6) . . ?
C8G C7G C6G 114.2(9) . . ?
C9G C8G C7G 113.8(11) . . ?
C8G C9G C10G 111.5(10) . . ?
C1H N1H C2H 117.4(7) . . ?
C2H N2H C3H 112.2(6) . . ?
C5H N3H C4H 103.1(6) . . ?
C3H N4H C5H 105.2(6) . . ?
C3H N4H C6H 128.4(5) . . ?
C5H N4H C6H 126.3(6) . . ?
N1H C1H C4H 123.4(7) . . ?
N1H C1H Cl1H 115.9(6) . . ?
C4H C1H Cl1H 120.6(5) . . ?
N5H C2H N2H 117.3(7) . . ?
N5H C2H N1H 116.5(7) . . ?
N2H C2H N1H 126.2(6) . . ?
N4H C3H N2H 126.2(7) . . ?
N4H C3H C4H 106.2(5) . . ?
N2H C3H C4H 127.5(7) . . ?
N3H C4H C1H 135.3(7) . . ?
N3H C4H C3H 111.3(7) . . ?
C1H C4H C3H 113.3(6) . . ?
N3H C5H N4H 114.2(7) . . ?
N4H C6H C7H 113.0(7) . . ?
C6H C7H C8H 112.8(7) . . ?
C9H C8H C7H 115.1(9) . . ?
C8H C9H C10H 114.5(12) . . ?

_refine_diff_density_max         0.572
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.104

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method Sublimation
_chemical_compound_source        6-Chloro-purin-2-amine
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xylene_prGCl
_database_code_depnum_ccdc_archive 'CCDC 1417640'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_RFACG01_I                   
;
PROBLEM: The value of the R factor is > 0.20
RESPONSE: As the crystals are very thin, the collected intensities
are weak. In addition, one of the host molecule, and the guest toluene
molecules are disordered. Thus, the structure was refined poorly.
However, all non-H atoms were identified and refined anisotropically.
This structure is important for understanding the host-guest
interactions although the data quality is poor.  
;
_vrf_RFACR01_I                   
;
PROBLEM: The value of the weighted R factor is > 0.45
RESPONSE: A same reason explained above for RFACG01_I.
;
_vrf_RINTA01_I                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: A same reason explained above for RFACG01_I.
;
_vrf_PLAT020_I                   
;
PROBLEM: The value of Rint is greater than 0.12 ......... 0.534 Report
RESPONSE: A same reason explained above for RFACG01_I.
;
_vrf_PLAT082_I                   
;
PROBLEM: High R1 Value .................................. 0.26 Report
RESPONSE: A same reason explained above for RFACG01_I.
;
_vrf_PLAT084_I                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.63 Report
RESPONSE: A same reason explained above for RFACG01_I.
;
_vrf_PLAT015_I                   
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF .... Please Do !
RESPONSE: The hkl part was removed, and a fcf file was reported to CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'p-xylene with 6-Chloro-9-propyl-purin-2-amine'
_chemical_name_common            xylene_pr_GCl
_chemical_melting_point          none
_chemical_formula_moiety         '2(C8 H10 Cl N5), C2 H1.50, 1.5(C4 H5), H'
_chemical_formula_sum            'C24 H30 Cl2 N10'
_chemical_formula_weight         529.48

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           68
_space_group_name_H-M_alt        'C c c a'
_space_group_name_Hall           '-C 2b 2bc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1, -y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x, y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
'-x, y+1/2, z-1/2'

_cell_length_a                   15.022(3)
_cell_length_b                   44.140(9)
_cell_length_c                   15.211(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10086(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    851
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      20.2

_exptl_crystal_description       'rectangular thin plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             4448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
Denzo and Scalepack
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.710
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'PLSII 2D bending magnet'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            96254
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.534
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       62
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.709
_diffrn_reflns_theta_max         30.473
_diffrn_reflns_theta_full        25.214
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7649
_reflns_number_gt                3498
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'PAL ADSC Quantum-210 ADX Program'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL XP'
_computing_publication_material  'SHELXTL XCIF'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7649
_refine_ls_number_parameters     432
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.3296
_refine_ls_R_factor_gt           0.2602
_refine_ls_wR_factor_ref         0.6304
_refine_ls_wR_factor_gt          0.5974
_refine_ls_goodness_of_fit_ref   2.240
_refine_ls_restrained_S_all      15.899
_refine_ls_shift/su_max          0.072
_refine_ls_shift/su_mean         0.012

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.54342(10) 0.58573(4) 0.35317(7) 0.0564(7) Uani 1 1 d G . . A 1
N1 N 0.48446(8) 0.58825(4) 0.51221(8) 0.0502(16) Uani 1 1 d G . . A 1
N2 N 0.57099(11) 0.58973(5) 0.64711(7) 0.0484(15) Uani 1 1 d G . . A 1
N3 N 0.41762(11) 0.59072(6) 0.64741(10) 0.0558(18) Uani 1 1 d G . . A 1
H3A H 0.4191 0.5917 0.7052 0.067 Uiso 1 1 calc R U . A 1
H3B H 0.3662 0.5906 0.6198 0.067 Uiso 1 1 calc R U . A 1
N4 N 0.72785(8) 0.58641(5) 0.47046(10) 0.0598(18) Uani 1 1 d G . . A 1
N5 N 0.72865(10) 0.58857(5) 0.61803(10) 0.0498(15) Uani 1 1 d DG . . A 1
C1 C 0.55857(8) 0.58739(3) 0.46513(7) 0.0505(18) Uani 1 1 d G . . A 1
C2 C 0.49418(10) 0.58946(4) 0.60128(8) 0.0489(18) Uani 1 1 d G . . A 1
C3 C 0.64112(10) 0.58856(4) 0.59280(8) 0.0519(18) Uani 1 1 d G . . A 1
C4 C 0.64083(8) 0.58715(4) 0.50222(8) 0.050(2) Uani 1 1 d G . . A 1
C5 C 0.77615(9) 0.58748(5) 0.54164(12) 0.058(2) Uani 1 1 d G . . A 1
H5 H 0.8394 0.5875 0.5404 0.070 Uiso 1 1 calc R U . A 1
C6 C 0.76366(13) 0.58841(6) 0.70803(11) 0.0545(19) Uani 1 1 d DG . . A 1
H6A H 0.7269 0.6020 0.7449 0.065 Uiso 1 1 calc R U . A 1
H6B H 0.8251 0.5965 0.7075 0.065 Uiso 1 1 calc R U . A 1
C7 C 0.76444(15) 0.55798(7) 0.74789(11) 0.057(2) Uani 1 1 d G . . A 1
H7A H 0.7040 0.5492 0.7433 0.069 Uiso 1 1 calc R U . A 1
H7B H 0.7787 0.5600 0.8112 0.069 Uiso 1 1 calc R U . A 1
C8 C 0.83066(15) 0.53609(7) 0.70601(14) 0.081(3) Uani 1 1 d G . . A 1
H8A H 0.8202 0.5352 0.6425 0.121 Uiso 1 1 calc R U . A 1
H8B H 0.8229 0.5159 0.7315 0.121 Uiso 1 1 calc R U . A 1
H8C H 0.8915 0.5432 0.7171 0.121 Uiso 1 1 calc R U . A 1
Cl1A Cl 0.29402(15) 0.66514(6) 0.35318(15) 0.0537(12) Uani 0.5 1 d G . P A -2
N1A N 0.23314(14) 0.66184(7) 0.51139(16) 0.059(4) Uani 0.5 1 d G U P A -2
N2A N 0.31801(17) 0.66020(7) 0.64730(14) 0.044(4) Uani 0.5 1 d G . P A -2
N3A N 0.16465(16) 0.65914(9) 0.64575(18) 0.052(3) Uani 0.5 1 d G . P A -2
H3A1 H 0.1654 0.6583 0.7035 0.063 Uiso 0.5 1 calc R U P A -2
H3A2 H 0.1135 0.6592 0.6175 0.063 Uiso 0.5 1 calc R U P A -2
N5A N 0.47596(16) 0.66206(5) 0.62021(13) 0.045(3) Uani 0.5 1 d DG . P A -2
C1A C 0.30778(14) 0.66345(5) 0.46531(15) 0.055(4) Uani 0.5 1 d G . P A -2
C2A C 0.24177(15) 0.66037(7) 0.60053(16) 0.054(4) Uani 0.5 1 d G . P A -2
C3A C 0.38878(15) 0.66169(5) 0.59388(13) 0.042(3) Uani 0.5 1 d G . P A -2
C4A C 0.38961(14) 0.66315(5) 0.50330(13) 0.067(9) Uani 0.5 1 d G . P A -2
C5A C 0.52436(15) 0.66402(4) 0.54452(13) 0.048(4) Uani 0.5 1 d G . P A -2
H5A H 0.5875 0.6649 0.5444 0.058 Uiso 0.5 1 calc R U P A -2
C6A C 0.51003(18) 0.65953(6) 0.71027(13) 0.067(5) Uani 0.5 1 d DG . P A -2
H6A1 H 0.5723 0.6522 0.7113 0.081 Uiso 0.5 1 calc R U P A -2
H6A2 H 0.4726 0.6460 0.7466 0.081 Uiso 0.5 1 calc R U P A -2
C7A C 0.5030(18) 0.6930(2) 0.741(2) 0.057(5) Uani 0.5 1 d D . P A -2
H7A1 H 0.4452 0.7011 0.7199 0.069 Uiso 0.5 1 calc R U P A -2
H7A2 H 0.5014 0.6931 0.8058 0.069 Uiso 0.5 1 calc R U P A -2
C8A C 0.5765(10) 0.7149(4) 0.7109(11) 0.078(5) Uani 0.5 1 d D . P A -2
H8A1 H 0.6346 0.7070 0.7292 0.117 Uiso 0.5 1 calc R U P A -2
H8A2 H 0.5667 0.7348 0.7376 0.117 Uiso 0.5 1 calc R U P A -2
H8A3 H 0.5751 0.7168 0.6467 0.117 Uiso 0.5 1 calc R U P A -2
Cl1B Cl 0.2938(3) 0.66289(13) 0.64613(18) 0.0567(14) Uani 0.5 1 d G . P B -3
N1B N 0.2366(2) 0.66158(13) 0.4864(2) 0.055(4) Uani 0.5 1 d G U P B -3
N2B N 0.3246(3) 0.66048(16) 0.35235(17) 0.058(4) Uani 0.5 1 d G . P B -3
N3B N 0.1712(3) 0.6602(2) 0.3503(3) 0.056(3) Uani 0.5 1 d G . P B -3
H3B1 H 0.1733 0.6596 0.2925 0.068 Uiso 0.5 1 calc R U P B -3
H3B2 H 0.1194 0.6604 0.3774 0.068 Uiso 0.5 1 calc R U P B -3
N5B N 0.4795(2) 0.66202(13) 0.5308(2) 0.052(3) Uani 0.5 1 d DG U P B -3
N4B N 0.4819(2) 0.66072(13) 0.3832(2) 0.054(3) Uani 0.5 1 d G U P B -3
C1B C 0.3102(2) 0.66182(10) 0.53427(18) 0.054(4) Uani 0.5 1 d G . P B -3
C2B C 0.2472(2) 0.66085(16) 0.3973(2) 0.051(4) Uani 0.5 1 d G . P B -3
C3B C 0.3941(2) 0.66100(11) 0.40747(18) 0.050(4) Uani 0.5 1 d G . P B -3
C4B C 0.3928(2) 0.66188(9) 0.49810(18) 0.038(7) Uani 0.5 1 d G . P B -3
C5B C 0.5286(2) 0.66113(14) 0.4601(3) 0.046(3) Uani 0.5 1 d G U P B -3
H5B H 0.5918 0.6608 0.4621 0.055 Uiso 0.5 1 calc R U P B -3
N4A N 0.4768(2) 0.66456(12) 0.4713(2) 0.053(3) Uani 0.5 1 d G . P A -2
C6B C 0.5179(3) 0.66123(18) 0.2936(3) 0.055(4) Uani 0.5 1 d DG . P B -3
H6B1 H 0.4843 0.6466 0.2573 0.066 Uiso 0.5 1 calc R U P B -3
H6B2 H 0.5807 0.6544 0.2955 0.066 Uiso 0.5 1 calc R U P B -3
C7B C 0.5142(13) 0.6924(2) 0.2489(14) 0.052(5) Uani 0.5 1 d D . P B -3
H7B1 H 0.4525 0.7003 0.2496 0.062 Uiso 0.5 1 calc R U P B -3
H7B2 H 0.5338 0.6907 0.1869 0.062 Uiso 0.5 1 calc R U P B -3
C8B C 0.5763(8) 0.7141(3) 0.2998(10) 0.066(4) Uani 0.5 1 d D . P B -3
H8B1 H 0.5602 0.7140 0.3622 0.099 Uiso 0.5 1 calc R U P B -3
H8B2 H 0.5700 0.7347 0.2764 0.099 Uiso 0.5 1 calc R U P B -3
H8B3 H 0.6381 0.7074 0.2931 0.099 Uiso 0.5 1 calc R U P B -3
C1X C 0.5770(10) 0.5052(4) 0.4498(8) 0.059(6) Uani 0.5 1 d D . P C 4
H1X H 0.6294 0.5090 0.4166 0.071 Uiso 0.5 1 calc R U P C 4
C2X C 0.5736(9) 0.5130(5) 0.5390(8) 0.042(4) Uani 0.5 1 d D . P C 4
H2X H 0.6244 0.5219 0.5657 0.050 Uiso 0.5 1 calc R U P C 4
C3X C 0.4973(9) 0.5081(4) 0.5900(7) 0.045(4) Uani 0.5 1 d D . P C 4
C4X C 0.4915(14) 0.5156(4) 0.6846(7) 0.087(6) Uani 0.5 1 d D . P C 4
H3X H 0.4941 0.5377 0.6921 0.130 Uiso 0.5 1 calc R U P C 4
H4X H 0.5413 0.5062 0.7159 0.130 Uiso 0.5 1 calc R U P C 4
H5X H 0.4352 0.5080 0.7084 0.130 Uiso 0.5 1 calc R U P C 4
C1X' C 0.5360(10) 0.4881(5) 0.4222(10) 0.056(6) Uani 0.5 1 d D . P D 5
H6X H 0.5596 0.4798 0.3695 0.067 Uiso 0.5 1 calc R U P D 5
C2X' C 0.4436(11) 0.4867(5) 0.4405(11) 0.051(5) Uani 0.5 1 d D . P D 5
H7X H 0.4034 0.4778 0.3998 0.061 Uiso 0.5 1 calc R U P D 5
C3X' C 0.4125(11) 0.4990(4) 0.5205(10) 0.048(4) Uani 0.5 1 d D . P D 5
C4X' C 0.3245(10) 0.5006(5) 0.5583(12) 0.149(10) Uani 0.5 1 d D . P D 5
H8X H 0.2892 0.5158 0.5266 0.223 Uiso 0.5 1 calc R U P D 5
H9X H 0.3291 0.5065 0.6203 0.223 Uiso 0.5 1 calc R U P D 5
H10X H 0.2956 0.4808 0.5537 0.223 Uiso 0.5 1 calc R U P D 5
C5X C 0.6797(5) 0.7629(3) 0.4528(6) 0.057(5) Uani 0.5 1 d D . P E 6
H11X H 0.6319 0.7717 0.4208 0.068 Uiso 0.5 1 calc R U P E 6
C6X C 0.6679(4) 0.7549(3) 0.5409(7) 0.069(7) Uani 0.5 1 d D . P E 6
H12X H 0.6121 0.7581 0.5687 0.083 Uiso 0.5 1 calc R U P E 6
C7X C 0.7382(7) 0.7419(3) 0.5882(3) 0.106(9) Uani 0.5 1 d D U P E 6
C8X C 0.7257(15) 0.7334(6) 0.6815(5) 0.29(2) Uani 0.5 1 d D U P E 6
H13X H 0.6852 0.7160 0.6853 0.437 Uiso 0.5 1 calc R U P E 6
H14X H 0.7003 0.7506 0.7138 0.437 Uiso 0.5 1 calc R U P E 6
H15X H 0.7833 0.7280 0.7073 0.437 Uiso 0.5 1 calc R U P E 6
C5X' C 0.6603(2) 0.7505(2) 0.4754(7) 0.108(9) Uani 0.5 1 d D U P F 7
H16X H 0.5993 0.7508 0.4586 0.130 Uiso 0.5 1 calc R U P F 8
C6X' C 0.6865(5) 0.7629(3) 0.5559(6) 0.063(6) Uani 0.5 1 d D . P F 7
H17X H 0.6434 0.7717 0.5938 0.076 Uiso 0.5 1 calc R U P F 8
C7X' C 0.7762(6) 0.7624(2) 0.5806(4) 0.172(18) Uani 0.5 1 d D U P F 7
C8X' C 0.8039(13) 0.7756(5) 0.6658(8) 0.23(3) Uani 0.25 1 d D U P F 7
H18X H 0.7762 0.7955 0.6732 0.350 Uiso 0.25 1 calc R U P F 7
H19X H 0.8688 0.7777 0.6670 0.350 Uiso 0.25 1 calc R U P F 7
H20X H 0.7850 0.7622 0.7137 0.350 Uiso 0.25 1 calc R U P F 7
C9X' C 0.5653(4) 0.7510(5) 0.4493(14) 0.089(11) Uani 0.25 1 d D U P F 7
H21X H 0.5309 0.7623 0.4930 0.133 Uiso 0.25 1 calc R U P F 7
H22X H 0.5428 0.7302 0.4458 0.133 Uiso 0.25 1 calc R U P F 7
H23X H 0.5594 0.7608 0.3917 0.133 Uiso 0.25 1 calc R U P F 7


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cl1 C1 1.7198 . ?
N1 C1 1.3242 . ?
N1 C2 1.3638 . ?
N2 C3 1.3397 . ?
N2 C2 1.3482 . ?
N3 C2 1.3485 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C5 1.3042 . ?
N4 C4 1.3939 . ?
N5 C5 1.3644 . ?
N5 C3 1.3696 . ?
N5 C6 1.4666 . ?
C1 C4 1.3584 . ?
C3 C4 1.3793 . ?
C5 H5 0.9500 . ?
C6 C7 1.4737 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5260 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
Cl1A C1A 1.7197 . ?
N1A C1A 1.3242 . ?
N1A C2A 1.3637 . ?
N2A C3A 1.3397 . ?
N2A C2A 1.3482 . ?
N3A C2A 1.3484 . ?
N3A H3A1 0.8800 . ?
N3A H3A2 0.8800 . ?
N5A C5A 1.3643 . ?
N5A C3A 1.3696 . ?
N5A C6A 1.4666 . ?
C1A C4A 1.3584 . ?
C3A C4A 1.3793 . ?
C4A N4A 1.398(4) . ?
C5A N4A 1.323(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.551(9) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A C8A 1.537(10) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
Cl1B C1B 1.7198 . ?
N1B C1B 1.3243 . ?
N1B C2B 1.3637 . ?
N2B C3B 1.3397 . ?
N2B C2B 1.3482 . ?
N3B C2B 1.3484 . ?
N3B H3B1 0.8800 . ?
N3B H3B2 0.8800 . ?
N5B C5B 1.3042 . ?
N5B C4B 1.3939 . ?
N4B C5B 1.3643 . ?
N4B C3B 1.3696 . ?
N4B C6B 1.4666 . ?
C1B C4B 1.3583 . ?
C3B C4B 1.3793 . ?
C5B H5B 0.9500 . ?
C6B C7B 1.536(9) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B C8B 1.545(10) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C1X C3X 1.400(2) 9_666 ?
C1X C2X 1.401(3) . ?
C1X H1X 0.9500 . ?
C2X C3X 1.400(3) . ?
C2X H2X 0.9500 . ?
C3X C1X 1.400(2) 9_666 ?
C3X C4X 1.479(3) . ?
C4X H3X 0.9800 . ?
C4X H4X 0.9800 . ?
C4X H5X 0.9800 . ?
C1X' C3X' 1.30(2) 9_666 ?
C1X' C2X' 1.418(15) . ?
C1X' H6X 0.9500 . ?
C2X' C3X' 1.412(14) . ?
C2X' H7X 0.9500 . ?
C3X' C1X' 1.30(2) 9_666 ?
C3X' C4X' 1.443(15) . ?
C4X' H8X 0.9800 . ?
C4X' H9X 0.9800 . ?
C4X' H10X 0.9800 . ?
C5X C6X 1.398(3) . ?
C5X C7X 1.399(3) 13_666 ?
C5X H11X 0.9500 . ?
C6X C7X 1.399(3) . ?
C6X H12X 0.9500 . ?
C7X C5X 1.399(3) 13_666 ?
C7X C8X 1.481(3) . ?
C8X H13X 0.9800 . ?
C8X H14X 0.9800 . ?
C8X H15X 0.9800 . ?
C5X' C6X' 1.398(3) . ?
C5X' C7X' 1.399(3) 13_666 ?
C5X' C9X' 1.481(3) . ?
C6X' C7X' 1.399(3) . ?
C7X' C5X' 1.399(3) 13_666 ?
C7X' C8X' 1.480(3) . ?
C8X' H18X 0.9800 . ?
C8X' H19X 0.9800 . ?
C8X' H20X 0.9800 . ?
C9X' C9X' 1.964(14) 6_565 ?
C9X' H21X 0.9800 . ?
C9X' H22X 0.9800 . ?
C9X' H23X 0.9800 . ?

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
C1 N1 C2 116.6 . . ?
C3 N2 C2 110.7 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C5 N4 C4 103.5 . . ?
C5 N5 C3 105.3 . . ?
C5 N5 C6 127.4 . . ?
C3 N5 C6 127.3 . . ?
N1 C1 C4 122.7 . . ?
N1 C1 Cl1 115.2 . . ?
C4 C1 Cl1 122.1 . . ?
N2 C2 N3 117.4 . . ?
N2 C2 N1 127.3 . . ?
N3 C2 N1 115.3 . . ?
N2 C3 N5 125.6 . . ?
N2 C3 C4 128.0 . . ?
N5 C3 C4 106.4 . . ?
C1 C4 C3 114.7 . . ?
C1 C4 N4 135.2 . . ?
C3 C4 N4 110.1 . . ?
N4 C5 N5 114.7 . . ?
N4 C5 H5 122.7 . . ?
N5 C5 H5 122.7 . . ?
N5 C6 C7 113.0 . . ?
N5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C8 114.2 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1A N1A C2A 116.6 . . ?
C3A N2A C2A 110.7 . . ?
C2A N3A H3A1 120.0 . . ?
C2A N3A H3A2 120.0 . . ?
H3A1 N3A H3A2 120.0 . . ?
C5A N5A C3A 105.3 . . ?
C5A N5A C6A 127.4 . . ?
C3A N5A C6A 127.3 . . ?
N1A C1A C4A 122.7 . . ?
N1A C1A Cl1A 115.2 . . ?
C4A C1A Cl1A 122.1 . . ?
N2A C2A N3A 117.4 . . ?
N2A C2A N1A 127.3 . . ?
N3A C2A N1A 115.3 . . ?
N2A C3A N5A 125.6 . . ?
N2A C3A C4A 128.0 . . ?
N5A C3A C4A 106.4 . . ?
C1A C4A C3A 114.7 . . ?
C1A C4A N4A 134.36(17) . . ?
C3A C4A N4A 110.96(17) . . ?
N4A C5A N5A 115.04(18) . . ?
N4A C5A H5A 122.5 . . ?
N5A C5A H5A 122.5 . . ?
N5A C6A C7A 100.5(14) . . ?
N5A C6A H6A1 111.7 . . ?
C7A C6A H6A1 111.7 . . ?
N5A C6A H6A2 111.7 . . ?
C7A C6A H6A2 111.7 . . ?
H6A1 C6A H6A2 109.4 . . ?
C8A C7A C6A 117.5(14) . . ?
C8A C7A H7A1 108.0 . . ?
C6A C7A H7A1 108.0 . . ?
C8A C7A H7A2 107.9 . . ?
C6A C7A H7A2 107.9 . . ?
H7A1 C7A H7A2 107.2 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C1B N1B C2B 116.6 . . ?
C3B N2B C2B 110.7 . . ?
C2B N3B H3B1 120.0 . . ?
C2B N3B H3B2 120.0 . . ?
H3B1 N3B H3B2 120.0 . . ?
C5B N5B C4B 103.5 . . ?
C5B N4B C3B 105.3 . . ?
C5B N4B C6B 127.4 . . ?
C3B N4B C6B 127.3 . . ?
N1B C1B C4B 122.7 . . ?
N1B C1B Cl1B 115.2 . . ?
C4B C1B Cl1B 122.1 . . ?
N2B C2B N3B 117.4 . . ?
N2B C2B N1B 127.3 . . ?
N3B C2B N1B 115.3 . . ?
N2B C3B N4B 125.6 . . ?
N2B C3B C4B 128.0 . . ?
N4B C3B C4B 106.4 . . ?
C1B C4B C3B 114.7 . . ?
C1B C4B N5B 135.2 . . ?
C3B C4B N5B 110.1 . . ?
N5B C5B N4B 114.7 . . ?
N5B C5B H5B 122.7 . . ?
N4B C5B H5B 122.7 . . ?
C5A N4A C4A 102.3(3) . . ?
N4B C6B C7B 114.3(9) . . ?
N4B C6B H6B1 108.7 . . ?
C7B C6B H6B1 108.7 . . ?
N4B C6B H6B2 108.7 . . ?
C7B C6B H6B2 108.7 . . ?
H6B1 C6B H6B2 107.6 . . ?
C6B C7B C8B 108.1(12) . . ?
C6B C7B H7B1 110.1 . . ?
C8B C7B H7B1 110.1 . . ?
C6B C7B H7B2 110.1 . . ?
C8B C7B H7B2 110.1 . . ?
H7B1 C7B H7B2 108.4 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C3X C1X C2X 119.5(13) 9_666 . ?
C3X C1X H1X 120.2 9_666 . ?
C2X C1X H1X 120.2 . . ?
C3X C2X C1X 121.9(13) . . ?
C3X C2X H2X 119.0 . . ?
C1X C2X H2X 119.0 . . ?
C1X C3X C2X 118.6(10) 9_666 . ?
C1X C3X C4X 117.9(14) 9_666 . ?
C2X C3X C4X 123.5(13) . . ?
C3X C4X H3X 109.5 . . ?
C3X C4X H4X 109.5 . . ?
H3X C4X H4X 109.5 . . ?
C3X C4X H5X 109.5 . . ?
H3X C4X H5X 109.5 . . ?
H4X C4X H5X 109.5 . . ?
C3X' C1X' C2X' 118.1(17) 9_666 . ?
C3X' C1X' H6X 121.0 9_666 . ?
C2X' C1X' H6X 121.0 . . ?
C1X' C2X' C3X' 118.5(17) . . ?
C1X' C2X' H7X 120.8 . . ?
C3X' C2X' H7X 120.8 . . ?
C1X' C3X' C2X' 123.4(16) 9_666 . ?
C1X' C3X' C4X' 104.8(17) 9_666 . ?
C2X' C3X' C4X' 131.7(18) . . ?
C3X' C4X' H8X 109.5 . . ?
C3X' C4X' H9X 109.5 . . ?
H8X C4X' H9X 109.5 . . ?
C3X' C4X' H10X 109.5 . . ?
H8X C4X' H10X 109.5 . . ?
H9X C4X' H10X 109.5 . . ?
C6X C5X C7X 120.0(2) . 13_666 ?
C6X C5X H11X 120.0 . . ?
C7X C5X H11X 120.0 13_666 . ?
C5X C6X C7X 120.0(2) . . ?
C5X C6X H12X 120.0 . . ?
C7X C6X H12X 120.0 . . ?
C5X C7X C6X 119.9(2) 13_666 . ?
C5X C7X C8X 120.0(2) 13_666 . ?
C6X C7X C8X 120.0(2) . . ?
C7X C8X H13X 109.5 . . ?
C7X C8X H14X 109.5 . . ?
H13X C8X H14X 109.5 . . ?
C7X C8X H15X 109.5 . . ?
H13X C8X H15X 109.5 . . ?
H14X C8X H15X 109.5 . . ?
C6X' C5X' C7X' 119.96(19) . 13_666 ?
C6X' C5X' C9X' 120.0(2) . . ?
C7X' C5X' C9X' 120.0(2) 13_666 . ?
C5X' C6X' C7X' 120.1(2) . . ?
C6X' C7X' C5X' 119.97(19) . 13_666 ?
C6X' C7X' C8X' 120.0(2) . . ?
C5X' C7X' C8X' 120.0(2) 13_666 . ?
C7X' C8X' H18X 109.5 . . ?
C7X' C8X' H19X 109.5 . . ?
H18X C8X' H19X 109.5 . . ?
C7X' C8X' H20X 109.5 . . ?
H18X C8X' H20X 109.5 . . ?
H19X C8X' H20X 109.5 . . ?
C5X' C9X' C9X' 164.1(6) . 6_565 ?
C5X' C9X' H21X 109.5 . . ?
C9X' C9X' H21X 59.7 6_565 . ?
C5X' C9X' H22X 109.5 . . ?
C9X' C9X' H22X 67.3 6_565 . ?
H21X C9X' H22X 109.5 . . ?
C5X' C9X' H23X 109.5 . . ?
C9X' C9X' H23X 85.9 6_565 . ?
H21X C9X' H23X 109.5 . . ?
H22X C9X' H23X 109.5 . . ?

_refine_diff_density_max         2.190
_refine_diff_density_min         -1.519
_refine_diff_density_rms         0.258

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: p-xylene'
_chemical_compound_source        6-Chloro-purin-2-amine
_chemical_properties_physical    'Very thin and fragile plate crystals'
