#------------------------------------------------------------------------------
#$Date: 2024-09-06 04:54:33 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294623 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159977.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_7159977
loop_
_publ_author_name
'Lakshman, Mahesh K.'
'Malinchak, Casina T.'
'Shank, Nathaniel'
'Neary, Michelle C.'
'Stahl, Lothar'
_publ_section_title
;
 Purinyl N-directed aroylation of 6-arylpurine ribo- and
 2'-deoxyribonucleosides, and mechanistic insights.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6718
_journal_page_last               6726
_journal_paper_doi               10.1039/d4ob00689e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C32.5 H23.5 N4 O'
_chemical_formula_weight         486.05
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-02-16 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                91.2850(10)
_cell_angle_beta                 98.9400(10)
_cell_angle_gamma                113.2640(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9632(2)
_cell_length_b                   11.4926(2)
_cell_length_c                   12.0157(2)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      3.45
_cell_volume                     1243.28(4)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26186
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9549
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       bar
_exptl_crystal_F_000             509
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         7201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0452
_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)+(0.0661P)²+0.2896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                6077
_reflns_number_total             7201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob00689e2.cif
_cod_data_source_block           ml1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159976--7159977.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C32.50 H23.50 N4 O'
_cod_database_code               7159977
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.91199(9) 0.31869(8) 0.35368(7) 0.03277(18) Uani 1 1 d . . .
N1 N 0.57939(10) 0.32244(8) 0.24444(8) 0.02567(18) Uani 1 1 d . . .
N2 N 0.38512(11) 0.39898(8) 0.21257(8) 0.02882(19) Uani 1 1 d . . .
N3 N 0.20837(10) 0.06127(8) 0.14955(9) 0.0298(2) Uani 1 1 d . . .
N4 N 0.14303(10) 0.22825(9) 0.15063(8) 0.02674(18) Uani 1 1 d . . .
C1 C 0.48521(11) 0.20029(9) 0.21569(8) 0.02188(18) Uani 1 1 d . . .
C2 C 0.52580(13) 0.41273(10) 0.24229(10) 0.0296(2) Uani 1 1 d . . .
H2 H 0.5969 0.4972 0.2648 0.036 Uiso 1 1 calc R . .
C3 C 0.29402(11) 0.27723(9) 0.18460(8) 0.02372(19) Uani 1 1 d . . .
C4 C 0.33378(11) 0.17270(9) 0.18405(8) 0.02292(19) Uani 1 1 d . . .
C5 C 0.09969(12) 0.09997(10) 0.13081(10) 0.0308(2) Uani 1 1 d . . .
H5 H -0.0009 0.0432 0.1055 0.037 Uiso 1 1 calc R . .
C6 C 0.55184(10) 0.10622(9) 0.21597(8) 0.02102(18) Uani 1 1 d . . .
C7 C 0.47833(11) -0.00665(9) 0.14757(8) 0.02291(19) Uani 1 1 d . . .
H7 H 0.3816 -0.0256 0.1064 0.027 Uiso 1 1 calc R . .
C8 C 0.54368(11) -0.09494(9) 0.13735(8) 0.02167(18) Uani 1 1 d . . .
C9 C 0.46793(12) -0.21163(10) 0.06844(9) 0.0263(2) Uani 1 1 d . . .
H9 H 0.3703 -0.2325 0.0280 0.032 Uiso 1 1 calc R . .
C10 C 0.53470(12) -0.29446(10) 0.05984(9) 0.0285(2) Uani 1 1 d . . .
H10 H 0.4830 -0.3725 0.0136 0.034 Uiso 1 1 calc R . .
C11 C 0.67947(12) -0.26481(10) 0.11910(9) 0.0286(2) Uani 1 1 d . . .
H11 H 0.7249 -0.3227 0.1121 0.034 Uiso 1 1 calc R . .
C12 C 0.75535(12) -0.15293(10) 0.18685(9) 0.0264(2) Uani 1 1 d . . .
H12 H 0.8527 -0.1341 0.2268 0.032 Uiso 1 1 calc R . .
C13 C 0.68931(11) -0.06523(9) 0.19752(8) 0.02160(18) Uani 1 1 d . . .
C14 C 0.76335(11) 0.05108(9) 0.26749(8) 0.02271(19) Uani 1 1 d . . .
H14 H 0.8610 0.0717 0.3077 0.027 Uiso 1 1 calc R . .
C15 C 0.69745(10) 0.13471(9) 0.27865(8) 0.02105(18) Uani 1 1 d . . .
C16 C 0.78466(11) 0.25098(9) 0.36140(8) 0.02335(19) Uani 1 1 d . . .
C17 C 0.71737(11) 0.27323(9) 0.45807(8) 0.02403(19) Uani 1 1 d . . .
C18 C 0.77395(13) 0.39459(11) 0.51453(10) 0.0320(2) Uani 1 1 d . . .
H18 H 0.8549 0.4614 0.4919 0.038 Uiso 1 1 calc R . .
C19 C 0.71197(15) 0.41777(12) 0.60385(11) 0.0391(3) Uani 1 1 d . . .
H19 H 0.7489 0.5011 0.6409 0.047 Uiso 1 1 calc R . .
C20 C 0.59686(16) 0.32030(14) 0.63912(10) 0.0409(3) Uani 1 1 d . . .
H20 H 0.5557 0.3365 0.7009 0.049 Uiso 1 1 calc R . .
C21 C 0.54161(16) 0.19927(13) 0.58460(11) 0.0422(3) Uani 1 1 d . . .
H21 H 0.4632 0.1320 0.6094 0.051 Uiso 1 1 calc R . .
C22 C 0.60088(14) 0.17592(11) 0.49333(10) 0.0327(2) Uani 1 1 d . . .
H22 H 0.5614 0.0930 0.4550 0.039 Uiso 1 1 calc R . .
C23 C 0.05033(13) 0.30087(11) 0.12795(10) 0.0307(2) Uani 1 1 d . . .
H23A H 0.0893 0.3767 0.1834 0.037 Uiso 1 1 calc R . .
H23B H -0.0523 0.2475 0.1377 0.037 Uiso 1 1 calc R . .
C24 C 0.04800(11) 0.34254(9) 0.00985(9) 0.02446(19) Uani 1 1 d . . .
C25 C -0.04930(12) 0.26036(11) -0.08143(11) 0.0333(2) Uani 1 1 d . . .
H25 H -0.1140 0.1769 -0.0696 0.040 Uiso 1 1 calc R . .
C26 C -0.05208(15) 0.29999(14) -0.18975(12) 0.0435(3) Uani 1 1 d . . .
H26 H -0.1195 0.2439 -0.2518 0.052 Uiso 1 1 calc R . .
C27 C 0.04325(16) 0.42097(14) -0.20756(11) 0.0423(3) Uani 1 1 d . . .
H27 H 0.0418 0.4479 -0.2818 0.051 Uiso 1 1 calc R . .
C28 C 0.14046(14) 0.50239(12) -0.11727(11) 0.0355(3) Uani 1 1 d . . .
H28 H 0.2061 0.5854 -0.1295 0.043 Uiso 1 1 calc R . .
C29 C 0.14295(11) 0.46381(10) -0.00892(10) 0.0283(2) Uani 1 1 d . . .
H29 H 0.2099 0.5206 0.0529 0.034 Uiso 1 1 calc R . .
C1T C 0.1951(3) 0.2284(2) 0.47760(16) 0.0937(16) Uani 0.50 1 d P . .
H1T1 H 0.1541 0.2631 0.4137 0.141 Uiso 0.50 1 calc PR . .
H1T2 H 0.2851 0.2206 0.4622 0.141 Uiso 0.50 1 calc PR . .
H1T3 H 0.2197 0.2855 0.5464 0.141 Uiso 0.50 1 calc PR . .
C2T C 0.0994(3) 0.1191(2) 0.49122(16) 0.0962(8) Uani 1 1 d R . .
C3T C -0.0158(3) 0.1022(2) 0.54727(16) 0.1012(10) Uani 1 1 d R . .
H3T H -0.0255 0.1739 0.5799 0.121 Uiso 1 1 calc R . .
C4T C -0.1140(4) -0.0144(4) 0.5560(2) 0.1091(11) Uani 1 1 d . . .
H4T H -0.1941 -0.0261 0.5946 0.131 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 119.35(9) . . ?
C3 N2 C2 111.28(9) . . ?
C5 N3 C4 103.72(9) . . ?
C5 N4 C3 105.66(8) . . ?
C5 N4 C23 127.34(9) . . ?
C3 N4 C23 126.66(9) . . ?
N1 C1 C4 118.13(9) . . ?
N1 C1 C6 116.63(9) . . ?
C4 C1 C6 125.20(9) . . ?
N2 C2 N1 128.22(10) . . ?
N2 C3 N4 127.21(9) . . ?
N2 C3 C4 126.81(9) . . ?
N4 C3 C4 105.98(9) . . ?
N3 C4 C1 133.81(9) . . ?
N3 C4 C3 109.99(9) . . ?
C1 C4 C3 116.20(9) . . ?
N3 C5 N4 114.65(10) . . ?
C7 C6 C15 119.31(8) . . ?
C7 C6 C1 119.58(9) . . ?
C15 C6 C1 120.89(8) . . ?
C6 C7 C8 121.63(9) . . ?
C7 C8 C9 121.84(9) . . ?
C7 C8 C13 118.98(9) . . ?
C9 C8 C13 119.18(9) . . ?
C10 C9 C8 120.36(10) . . ?
C9 C10 C11 120.51(10) . . ?
C12 C11 C10 120.51(9) . . ?
C11 C12 C13 120.34(9) . . ?
C12 C13 C14 122.18(9) . . ?
C12 C13 C8 119.11(9) . . ?
C14 C13 C8 118.71(8) . . ?
C15 C14 C13 121.75(9) . . ?
C14 C15 C6 119.59(9) . . ?
C14 C15 C16 116.31(8) . . ?
C6 C15 C16 124.07(8) . . ?
O1 C16 C17 121.12(9) . . ?
O1 C16 C15 119.81(9) . . ?
C17 C16 C15 118.79(8) . . ?
C22 C17 C18 119.40(10) . . ?
C22 C17 C16 121.60(9) . . ?
C18 C17 C16 118.99(9) . . ?
C19 C18 C17 119.96(11) . . ?
C20 C19 C18 120.34(11) . . ?
C19 C20 C21 120.02(11) . . ?
C20 C21 C22 119.98(12) . . ?
C17 C22 C21 120.27(10) . . ?
N4 C23 C24 111.56(8) . . ?
C29 C24 C25 119.23(10) . . ?
C29 C24 C23 120.24(10) . . ?
C25 C24 C23 120.53(10) . . ?
C26 C25 C24 120.19(11) . . ?
C27 C26 C25 120.11(12) . . ?
C28 C27 C26 119.80(12) . . ?
C27 C28 C29 120.37(11) . . ?
C28 C29 C24 120.29(11) . . ?
C1T C2T C3T 123.1 . . ?
C1T C2T C4T 116.9(2) . 2_556 ?
C3T C2T C4T 120.0(2) . 2_556 ?
C4T C3T C2T 120.09(16) . . ?
C3T C4T C2T 119.9(3) . 2_556 ?
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
O1 C16 1.2180(12) . ?
N1 C2 1.3404(13) . ?
N1 C1 1.3444(13) . ?
N2 C3 1.3325(13) . ?
N2 C2 1.3357(14) . ?
N3 C5 1.3154(14) . ?
N3 C4 1.3871(13) . ?
N4 C5 1.3660(14) . ?
N4 C3 1.3698(13) . ?
N4 C23 1.4713(13) . ?
C1 C4 1.3999(14) . ?
C1 C6 1.4751(13) . ?
C3 C4 1.4059(13) . ?
C6 C7 1.3818(13) . ?
C6 C15 1.4329(13) . ?
C7 C8 1.4176(13) . ?
C8 C9 1.4178(13) . ?
C8 C13 1.4198(13) . ?
C9 C10 1.3698(14) . ?
C10 C11 1.4090(16) . ?
C11 C12 1.3716(15) . ?
C12 C13 1.4176(13) . ?
C13 C14 1.4198(13) . ?
C14 C15 1.3759(13) . ?
C15 C16 1.5112(13) . ?
C16 C17 1.4927(14) . ?
C17 C22 1.3878(15) . ?
C17 C18 1.3932(14) . ?
C18 C19 1.3882(16) . ?
C19 C20 1.381(2) . ?
C20 C21 1.3816(19) . ?
C21 C22 1.3917(16) . ?
C23 C24 1.5074(15) . ?
C24 C29 1.3882(14) . ?
C24 C25 1.3909(15) . ?
C25 C26 1.3885(19) . ?
C26 C27 1.384(2) . ?
C27 C28 1.379(2) . ?
C28 C29 1.3845(17) . ?
C1T C2T 1.2746 . ?
C2T C3T 1.3705 . ?
C2T C4T 1.387(4) 2_556 ?
C3T C4T 1.330(4) . ?
C4T C2T 1.387(4) 2_556 ?
