#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:51:55 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180452 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/21/7212175.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_7212175
loop_
_publ_author_name
'Standara, Stanislav'
'Malináková, Katerina'
'Marek, Radek'
'Marek, Jaromír'
'Hocek, Michal'
'Vaara, Juha'
'Straka, Michal'
_publ_section_title
;
 Understanding the NMR chemical shifts for 6-halopurines: role of
 structure, solvent and relativistic effects.
;
_journal_issue                   19
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              5126
_journal_page_last               5139
_journal_paper_doi               10.1039/b921383j
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C12 H9 Cl N4'
_chemical_formula_sum            'C12 H9 Cl N4'
_chemical_formula_weight         244.68
_chemical_name_common            9-benzyl-6-chloropurine
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.236(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9073(4)
_cell_length_b                   24.240(2)
_cell_length_c                   9.3569(8)
_cell_measurement_reflns_used    5007
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.7555
_cell_measurement_theta_min      3.3125
_cell_volume                     1111.26(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.3611
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'KUMA KM4 + CCD'
_diffrn_measurement_method       'rotation method, ω--scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4868
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1927
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0350P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                1830
_reflns_number_total             1927
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b921383j.txt
_cod_data_source_block           rm3
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               7212175
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
Cl1 Cl 0.7483(2) 0.64767(4) 0.26898(10) 0.0332(3) Uani 1 1 d .
N1 N 0.3794(6) 0.58998(13) 0.3947(3) 0.0271(7) Uani 1 1 d .
C2 C 0.2421(7) 0.54293(16) 0.4184(3) 0.0258(8) Uani 1 1 d .
H2 H 0.1045 0.5455 0.4856 0.031 Uiso 1 1 calc R
N3 N 0.2736(6) 0.49335(13) 0.3603(3) 0.0229(7) Uani 1 1 d .
C4 C 0.4677(7) 0.49390(14) 0.2647(3) 0.0188(7) Uani 1 1 d .
C5 C 0.6204(7) 0.53970(14) 0.2267(3) 0.0191(7) Uani 1 1 d .
C6 C 0.5682(7) 0.58794(15) 0.2994(4) 0.0236(8) Uani 1 1 d .
N7 N 0.7987(6) 0.52570(12) 0.1231(3) 0.0210(6) Uani 1 1 d .
C8 C 0.7529(7) 0.47321(14) 0.1030(3) 0.0202(7) Uani 1 1 d .
H8 H 0.8477 0.4520 0.0363 0.024 Uiso 1 1 calc R
N9 N 0.5573(5) 0.45073(12) 0.1853(3) 0.0197(6) Uani 1 1 d .
C10 C 0.4526(7) 0.39410(15) 0.1777(4) 0.0264(8) Uani 1 1 d .
H10A H 0.3416 0.3893 0.0869 0.032 Uiso 1 1 calc R
H10B H 0.3319 0.3880 0.2575 0.032 Uiso 1 1 calc R
C11 C 0.6770(7) 0.35147(14) 0.1857(4) 0.0209(7) Uani 1 1 d .
C12 C 0.7937(8) 0.33422(15) 0.3182(4) 0.0265(8) Uani 1 1 d .
H12 H 0.7301 0.3493 0.4040 0.032 Uiso 1 1 calc R
C13 C 1.0007(8) 0.29542(15) 0.3253(4) 0.0288(8) Uani 1 1 d .
H13 H 1.0787 0.2840 0.4158 0.035 Uiso 1 1 calc R
C14 C 1.0950(8) 0.27308(15) 0.2007(4) 0.0303(8) Uani 1 1 d .
H14 H 1.2379 0.2466 0.2057 0.036 Uiso 1 1 calc R
C15 C 0.9795(8) 0.28965(15) 0.0690(4) 0.0289(8) Uani 1 1 d .
H15 H 1.0421 0.2742 -0.0165 0.035 Uiso 1 1 calc R
C16 C 0.7733(7) 0.32867(15) 0.0616(4) 0.0251(8) Uani 1 1 d .
H16 H 0.6965 0.3400 -0.0292 0.030 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 N1 C2 117.0(3)
N3 C2 N1 128.7(3)
N3 C2 H2 115.6
N1 C2 H2 115.6
C2 N3 C4 111.5(3)
N3 C4 N9 128.0(3)
N3 C4 C5 126.0(3)
N9 C4 C5 106.0(3)
C6 C5 N7 133.9(3)
C6 C5 C4 115.5(3)
N7 C5 C4 110.6(3)
N1 C6 C5 121.3(3)
N1 C6 Cl1 117.6(3)
C5 C6 Cl1 121.1(3)
C8 N7 C5 103.3(3)
N7 C8 N9 115.2(3)
N7 C8 H8 122.4
N9 C8 H8 122.4
C4 N9 C8 104.9(3)
C4 N9 C10 128.2(3)
C8 N9 C10 126.7(3)
N9 C10 C11 112.7(3)
N9 C10 H10A 109.1
C11 C10 H10A 109.1
N9 C10 H10B 109.1
C11 C10 H10B 109.1
H10A C10 H10B 107.8
C16 C11 C12 118.6(3)
C16 C11 C10 120.8(3)
C12 C11 C10 120.6(3)
C13 C12 C11 120.5(3)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 120.2(3)
C12 C13 H13 119.9
C14 C13 H13 119.9
C15 C14 C13 119.7(4)
C15 C14 H14 120.2
C13 C14 H14 120.2
C16 C15 C14 120.2(3)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C11 120.7(3)
C15 C16 H16 119.6
C11 C16 H16 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C6 1.728(4)
N1 C6 1.323(5)
N1 C2 1.349(5)
C2 N3 1.332(5)
C2 H2 0.9500
N3 C4 1.343(4)
C4 N9 1.370(4)
C4 C5 1.396(5)
C5 C6 1.384(5)
C5 N7 1.385(4)
N7 C8 1.304(4)
C8 N9 1.377(4)
C8 H8 0.9500
N9 C10 1.466(5)
C10 C11 1.509(5)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C16 1.392(5)
C11 C12 1.401(5)
C12 C13 1.383(5)
C12 H12 0.9500
C13 C14 1.388(6)
C13 H13 0.9500
C14 C15 1.387(5)
C14 H14 0.9500
C15 C16 1.384(5)
C15 H15 0.9500
C16 H16 0.9500
