#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/05/4120522.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_4120522
loop_
_publ_author_name
'Kim, Hyun Jin'
'Ajitha, Manjaly J.'
'Lee, Yongjae'
'Ryu, Jaeyune'
'Kim, Jin'
'Lee, Yunho'
'Jung, Yousung'
'Chang, Sukbok'
_publ_section_title
;
 Hydrogen-Bond-Assisted Controlled C-H Functionalization via Adaptive
 Recognition of a Purine Directing Group.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1132
_journal_page_last               1140
_journal_paper_doi               10.1021/ja4118472
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C20 H18 N6 O2'
_chemical_formula_sum            'C20 H18 N6 O2'
_chemical_formula_weight         374.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.288(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.439(2)
_cell_length_b                   10.0614(17)
_cell_length_c                   14.778(2)
_cell_measurement_reflns_used    2426
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.47
_cell_volume                     1792.3(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0869
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11023
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.863
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0769P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1583
_reflns_number_gt                1691
_reflns_number_total             3537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4118472_si_003.cif
_cod_data_source_block           V1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1792.2(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4120522
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.2251(2) 0.2994(3) 0.29094(18) 0.0350(7) Uani 1 1 d .
N1 N 0.1441(2) 0.3267(2) 0.21396(16) 0.0418(6) Uani 1 1 d .
C2 C 0.1408(3) 0.4454(3) 0.1718(2) 0.0490(8) Uani 1 1 d .
H2 H 0.0813 0.4577 0.1182 0.059 Uiso 1 1 calc R
N2 N 0.2089(2) 0.5474(2) 0.19471(17) 0.0456(7) Uani 1 1 d .
C3 C 0.2890(2) 0.5192(3) 0.27163(19) 0.0375(7) Uani 1 1 d .
C4 C 0.3015(2) 0.4023(3) 0.32388(18) 0.0344(7) Uani 1 1 d .
N3 N 0.3925(2) 0.4157(2) 0.39991(16) 0.0421(6) Uani 1 1 d .
C5 C 0.4307(3) 0.5355(3) 0.3900(2) 0.0453(8) Uani 1 1 d .
H5 H 0.4940 0.5715 0.4325 0.054 Uiso 1 1 calc R
N4 N 0.37269(19) 0.6035(2) 0.31451(16) 0.0389(6) Uani 1 1 d .
C6 C 0.3985(3) 0.7316(3) 0.2763(2) 0.0506(8) Uani 1 1 d .
H6 H 0.3276 0.7818 0.2535 0.061 Uiso 1 1 calc R
C7 C 0.4479(3) 0.7071(3) 0.1946(2) 0.0756(12) Uani 1 1 d .
H7A H 0.5183 0.6593 0.2158 0.113 Uiso 1 1 calc R
H7B H 0.4612 0.7923 0.1671 0.113 Uiso 1 1 calc R
H7C H 0.3965 0.6537 0.1476 0.113 Uiso 1 1 calc R
C8 C 0.4749(3) 0.8137(3) 0.3515(3) 0.0748(11) Uani 1 1 d .
H8A H 0.4427 0.8218 0.4054 0.112 Uiso 1 1 calc R
H8B H 0.4840 0.9024 0.3269 0.112 Uiso 1 1 calc R
H8C H 0.5474 0.7701 0.3707 0.112 Uiso 1 1 calc R
C9 C 0.2257(2) 0.1670(3) 0.33502(18) 0.0367(7) Uani 1 1 d .
C10 C 0.3021(3) 0.1439(3) 0.42080(19) 0.0472(8) Uani 1 1 d .
H10 H 0.3547 0.2110 0.4461 0.057 Uiso 1 1 calc R
C11 C 0.3032(3) 0.0269(3) 0.4696(2) 0.0570(9) Uani 1 1 d .
H11 H 0.3560 0.0142 0.5275 0.068 Uiso 1 1 calc R
C12 C 0.2273(3) -0.0720(3) 0.4341(2) 0.0552(9) Uani 1 1 d .
H12 H 0.2267 -0.1519 0.4683 0.066 Uiso 1 1 calc R
C13 C 0.1529(3) -0.0543(3) 0.3495(2) 0.0482(8) Uani 1 1 d .
H13 H 0.1018 -0.1234 0.3254 0.058 Uiso 1 1 calc R
C14 C 0.1501(2) 0.0628(3) 0.2975(2) 0.0403(7) Uani 1 1 d .
N5 N 0.0707(2) 0.0813(2) 0.21453(16) 0.0454(7) Uani 1 1 d .
H5A H 0.1049 0.1345 0.1794 0.054 Uiso 1 1 d R
C15 C 0.0148(2) -0.0144(3) 0.15183(19) 0.0382(7) Uani 1 1 d .
C16 C -0.0832(2) 0.0266(3) 0.08975(18) 0.0387(7) Uani 1 1 d .
H16 H -0.1117 0.1132 0.0944 0.046 Uiso 1 1 calc R
C17 C -0.1383(2) -0.0598(3) 0.0215(2) 0.0404(7) Uani 1 1 d .
C18 C -0.1022(3) -0.1874(3) 0.0127(2) 0.0483(8) Uani 1 1 d .
H18 H -0.1424 -0.2458 -0.0340 0.058 Uiso 1 1 calc R
C19 C -0.0052(3) -0.2272(3) 0.0745(2) 0.0491(8) Uani 1 1 d .
H19 H 0.0221 -0.3144 0.0698 0.059 Uiso 1 1 calc R
C20 C 0.0527(3) -0.1429(3) 0.1426(2) 0.0447(8) Uani 1 1 d .
H20 H 0.1195 -0.1727 0.1839 0.054 Uiso 1 1 calc R
N6 N -0.2400(2) -0.0128(3) -0.04414(19) 0.0521(7) Uani 1 1 d .
O1 O -0.2886(2) -0.0890(3) -0.10526(16) 0.0762(8) Uani 1 1 d .
O2 O -0.2718(2) 0.1008(2) -0.03504(16) 0.0715(7) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C4 116.2(2)
N1 C1 C9 118.4(2)
C4 C1 C9 125.4(3)
C2 N1 C1 120.2(2)
N2 C2 N1 128.9(3)
N2 C2 H2 115.5
N1 C2 H2 115.5
C2 N2 C3 110.3(2)
N2 C3 N4 125.5(2)
N2 C3 C4 127.2(3)
N4 C3 C4 107.3(2)
N3 C4 C3 108.9(2)
N3 C4 C1 134.1(3)
C3 C4 C1 117.1(3)
C5 N3 C4 104.0(2)
N3 C5 N4 114.9(3)
N3 C5 H5 122.6
N4 C5 H5 122.6
C5 N4 C3 104.9(2)
C5 N4 C6 129.4(2)
C3 N4 C6 125.2(2)
N4 C6 C7 109.6(2)
N4 C6 C8 110.6(3)
C7 C6 C8 111.8(3)
N4 C6 H6 108.3
C7 C6 H6 108.3
C8 C6 H6 108.3
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C14 117.7(2)
C10 C9 C1 118.3(2)
C14 C9 C1 123.9(2)
C11 C10 C9 122.1(3)
C11 C10 H10 119.0
C9 C10 H10 119.0
C10 C11 C12 119.9(3)
C10 C11 H11 120.1
C12 C11 H11 120.1
C13 C12 C11 119.8(3)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C14 121.9(3)
C12 C13 H13 119.1
C14 C13 H13 119.1
N5 C14 C13 120.9(3)
N5 C14 C9 120.3(2)
C13 C14 C9 118.7(3)
C14 N5 C15 128.7(2)
C14 N5 H5A 104.5
C15 N5 H5A 104.5
C20 C15 C16 118.1(3)
C20 C15 N5 125.4(3)
C16 C15 N5 116.3(2)
C17 C16 C15 119.4(3)
C17 C16 H16 120.3
C15 C16 H16 120.3
C18 C17 C16 122.8(3)
C18 C17 N6 119.0(3)
C16 C17 N6 118.1(3)
C17 C18 C19 117.4(3)
C17 C18 H18 121.3
C19 C18 H18 121.3
C20 C19 C18 121.3(3)
C20 C19 H19 119.3
C18 C19 H19 119.3
C19 C20 C15 120.9(3)
C19 C20 H20 119.5
C15 C20 H20 119.5
O1 N6 O2 123.4(3)
O1 N6 C17 118.2(3)
O2 N6 C17 118.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.349(3)
C1 C4 1.409(4)
C1 C9 1.483(4)
N1 C2 1.342(3)
C2 N2 1.320(3)
C2 H2 0.9500
N2 C3 1.344(3)
C3 N4 1.371(3)
C3 C4 1.394(4)
C4 N3 1.391(3)
N3 C5 1.316(3)
C5 N4 1.355(3)
C5 H5 0.9500
N4 C6 1.474(3)
C6 C7 1.504(5)
C6 C8 1.516(4)
C6 H6 1.0000
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.403(4)
C9 C14 1.426(4)
C10 C11 1.379(4)
C10 H10 0.9500
C11 C12 1.382(4)
C11 H11 0.9500
C12 C13 1.371(4)
C12 H12 0.9500
C13 C14 1.403(4)
C13 H13 0.9500
C14 N5 1.384(3)
N5 C15 1.397(3)
N5 H5A 0.9200
C15 C20 1.394(4)
C15 C16 1.395(4)
C16 C17 1.379(4)
C16 H16 0.9500
C17 C18 1.377(4)
C17 N6 1.470(4)
C18 C19 1.380(4)
C18 H18 0.9500
C19 C20 1.376(4)
C19 H19 0.9500
C20 H20 0.9500
N6 O1 1.224(3)
N6 O2 1.227(3)
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
C4 C1 N1 C2 1.5(4)
C9 C1 N1 C2 -179.8(3)
C1 N1 C2 N2 0.3(5)
N1 C2 N2 C3 -0.4(5)
C2 N2 C3 N4 -179.5(3)
C2 N2 C3 C4 -1.3(4)
N2 C3 C4 N3 -177.7(3)
N4 C3 C4 N3 0.8(3)
N2 C3 C4 C1 3.0(4)
N4 C3 C4 C1 -178.6(2)
N1 C1 C4 N3 178.0(3)
C9 C1 C4 N3 -0.5(5)
N1 C1 C4 C3 -2.8(4)
C9 C1 C4 C3 178.6(2)
C3 C4 N3 C5 -0.7(3)
C1 C4 N3 C5 178.4(3)
C4 N3 C5 N4 0.5(3)
N3 C5 N4 C3 0.0(3)
N3 C5 N4 C6 -172.3(3)
N2 C3 N4 C5 178.0(3)
C4 C3 N4 C5 -0.5(3)
N2 C3 N4 C6 -9.3(4)
C4 C3 N4 C6 172.2(2)
C5 N4 C6 C7 99.9(3)
C3 N4 C6 C7 -70.9(4)
C5 N4 C6 C8 -23.8(4)
C3 N4 C6 C8 165.4(3)
N1 C1 C9 C10 -172.9(3)
C4 C1 C9 C10 5.7(4)
N1 C1 C9 C14 4.4(4)
C4 C1 C9 C14 -177.0(3)
C14 C9 C10 C11 -1.9(4)
C1 C9 C10 C11 175.5(3)
C9 C10 C11 C12 -0.1(5)
C10 C11 C12 C13 1.5(5)
C11 C12 C13 C14 -0.9(5)
C12 C13 C14 N5 -176.7(3)
C12 C13 C14 C9 -1.1(5)
C10 C9 C14 N5 178.0(3)
C1 C9 C14 N5 0.8(4)
C10 C9 C14 C13 2.5(4)
C1 C9 C14 C13 -174.8(3)
C13 C14 N5 C15 -27.2(5)
C9 C14 N5 C15 157.3(3)
C14 N5 C15 C20 -23.5(5)
C14 N5 C15 C16 161.0(3)
C20 C15 C16 C17 -0.6(4)
N5 C15 C16 C17 175.3(2)
C15 C16 C17 C18 1.5(4)
C15 C16 C17 N6 -178.7(2)
C16 C17 C18 C19 -1.4(4)
N6 C17 C18 C19 178.8(3)
C17 C18 C19 C20 0.4(4)
C18 C19 C20 C15 0.4(4)
C16 C15 C20 C19 -0.3(4)
N5 C15 C20 C19 -175.8(3)
C18 C17 N6 O1 -0.7(4)
C16 C17 N6 O1 179.4(3)
C18 C17 N6 O2 179.5(3)
C16 C17 N6 O2 -0.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122458
