#------------------------------------------------------------------------------
#$Date: 2023-06-29 16:47:12 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159437.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_7159437
loop_
_publ_author_name
'Fuchi, Yasufumi'
'Watanabe, Kouki'
'Shoji, Misa'
'Ito, Yuta'
'Hari, Yoshiyuki'
_publ_section_title
;
 Synthesis of purine derivatives of Me-TaNA and properties of
 Me-TaNA-modified oligonucleotides.
;
_journal_issue                   25
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5203
_journal_page_last               5213
_journal_paper_doi               10.1039/d3ob00745f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_sum            'C19 H19 N5 O6'
_chemical_formula_weight         413.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.573(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.660(2)
_cell_length_b                   6.1601(6)
_cell_length_c                   14.0178(13)
_cell_measurement_reflns_used    4466
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      25.3587
_cell_measurement_theta_min      2.8647
_cell_volume                     1886.5(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service v2017.5.0.0'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XSHELL V6.3.1'
_computing_publication_material  'Generate Report'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4765
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.57
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Tourbo X-ray Source'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.256
_refine_ls_abs_structure_details
;

Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3282
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0679P)²+1.1167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                3250
_reflns_number_total             3282
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00745f2.cif
_cod_data_source_block           YFC_069
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' 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 
;
_cod_database_code               7159437
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.62762(7) 0.2459(3) 0.56994(12) 0.0142(4) Uani d . . . 1 . .
O O4 0.64759(8) -0.0668(3) 0.67421(13) 0.0165(4) Uani d . . . 1 . .
O O2 0.71516(8) -0.2320(3) 0.56279(13) 0.0168(4) Uani d . . . 1 . .
H H2 0.7026 -0.3055 0.6012 0.025 Uiso calc U . R 1 . .
O O5 0.58495(7) -0.2118(3) 0.51258(13) 0.0172(4) Uani d . . . 1 . .
O O6 0.60847(8) 0.9777(3) 0.22174(13) 0.0171(4) Uani d . . . 1 . .
O O1 0.75442(8) 0.3351(3) 0.65546(14) 0.0182(4) Uani d . . . 1 . .
H H1 0.7899 0.2923 0.6652 0.027 Uiso calc U . R 1 . .
N N1 0.59955(9) 0.3124(4) 0.39267(15) 0.0125(4) Uani d . . . 1 . .
N N3 0.49859(9) 0.2900(4) 0.25527(15) 0.0137(4) Uani d . . . 1 . .
N N2 0.64450(9) 0.5463(3) 0.31972(15) 0.0136(4) Uani d . . . 1 . .
N N5 0.57015(9) 0.7200(4) 0.09745(16) 0.0141(4) Uani d . . . 1 . .
N N4 0.48992(9) 0.5166(4) 0.10992(15) 0.0154(4) Uani d . . . 1 . .
C C10 0.58387(10) 0.5143(4) 0.25472(18) 0.0112(5) Uani d . . . 1 . .
C C11 0.54786(11) 0.5871(4) 0.15550(17) 0.0129(5) Uani d . . . 1 . .
C C8 0.65144(11) 0.4243(4) 0.40013(18) 0.0138(5) Uani d . . . 1 . .
H H8 0.689 0.414 0.4584 0.017 Uiso calc U . R 1 . .
C C15 0.63493(11) 0.9214(4) -0.01717(19) 0.0154(5) Uani d . . . 1 . .
H H15 0.6155 0.7859 -0.0414 0.018 Uiso calc U . R 1 . .
C C9 0.55548(11) 0.3672(4) 0.29796(18) 0.0120(5) Uani d . . . 1 . .
C C2 0.67179(10) 0.0822(4) 0.62172(18) 0.0134(5) Uani d . . . 1 . .
C C19 0.66190(11) 1.2123(5) 0.10803(19) 0.0178(5) Uani d . . . 1 . .
H H19 0.6611 1.275 0.1694 0.021 Uiso calc U . R 1 . .
C C13 0.60339(11) 0.9057(4) 0.13802(18) 0.0129(5) Uani d . . . 1 . .
C C3 0.68066(10) -0.0397(4) 0.53329(18) 0.0134(5) Uani d . . . 1 . .
H H3 0.7005 0.0592 0.4988 0.016 Uiso calc U . R 1 . .
C C12 0.46904(11) 0.3736(5) 0.16105(19) 0.0160(5) Uani d . . . 1 . .
H H12 0.4281 0.3257 0.1258 0.019 Uiso calc U . R 1 . .
C C16 0.66514(11) 1.0287(5) -0.07148(18) 0.0176(5) Uani d . . . 1 . .
H H16 0.6662 0.9667 -0.1328 0.021 Uiso calc U . R 1 . .
C C14 0.63317(10) 1.0130(4) 0.07295(18) 0.0139(5) Uani d . . . 1 . .
C C4 0.61242(11) -0.0643(4) 0.46407(18) 0.0141(5) Uani d . . . 1 . .
H H4 0.606 -0.1099 0.3922 0.017 Uiso calc U . R 1 . .
C C1 0.72720(11) 0.1897(4) 0.70237(18) 0.0159(5) Uani d . . . 1 . .
H H1A 0.7146 0.2689 0.7524 0.019 Uiso calc U . R 1 . .
H H1B 0.7573 0.0774 0.7406 0.019 Uiso calc U . R 1 . .
C C6 0.58725(11) -0.1373(4) 0.61044(19) 0.0169(5) Uani d . . . 1 . .
H H6 0.5579 -0.014 0.5997 0.02 Uiso calc U . R 1 . .
C C5 0.59084(10) 0.1692(4) 0.46845(18) 0.0130(5) Uani d . . . 1 . .
H H5 0.5467 0.1687 0.459 0.016 Uiso calc U . R 1 . .
C C18 0.69144(11) 1.3183(5) 0.0533(2) 0.0214(6) Uani d . . . 1 . .
H H18 0.7103 1.4549 0.0767 0.026 Uiso calc U . R 1 . .
C C17 0.69361(11) 1.2263(5) -0.0358(2) 0.0190(6) Uani d . . . 1 . .
H H17 0.7146 1.2987 -0.0722 0.023 Uiso calc U . R 1 . .
C C7 0.56901(13) -0.3205(5) 0.6631(2) 0.0241(6) Uani d . . . 1 . .
H H7A 0.5974 -0.4421 0.6729 0.036 Uiso calc U . R 1 . .
H H7B 0.5274 -0.3675 0.6204 0.036 Uiso calc U . R 1 . .
H H7C 0.5704 -0.2714 0.7305 0.036 Uiso calc U . R 1 . .
H H20 0.5600(13) 0.687(6) 0.033(3) 0.018(8) Uiso d . . . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O3 C5 . . 108.52(18) ?
C2 O4 C6 . . 112.02(17) ?
C3 O2 H2 . . 109.5 ?
C6 O5 C4 . . 113.30(19) ?
C1 O1 H1 . . 109.5 ?
C8 N1 C9 . . 105.9(2) ?
C8 N1 C5 . . 128.3(2) ?
C9 N1 C5 . . 125.78(19) ?
C9 N3 C12 . . 111.2(2) ?
C8 N2 C10 . . 103.9(2) ?
C13 N5 C11 . . 122.0(2) ?
C13 N5 H20 . . 121.(2) ?
C11 N5 H20 . . 117.(2) ?
C11 N4 C12 . . 118.4(2) ?
N2 C10 C11 . . 133.6(2) ?
N2 C10 C9 . . 110.8(2) ?
C11 C10 C9 . . 115.4(2) ?
N4 C11 N5 . . 117.3(2) ?
N4 C11 C10 . . 119.4(2) ?
N5 C11 C10 . . 123.2(2) ?
N2 C8 N1 . . 114.1(2) ?
N2 C8 H8 . . 123.0 ?
N1 C8 H8 . . 123.0 ?
C16 C15 C14 . . 120.1(2) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
N3 C9 N1 . . 127.2(2) ?
N3 C9 C10 . . 127.4(2) ?
N1 C9 C10 . . 105.3(2) ?
O4 C2 O3 . . 110.78(18) ?
O4 C2 C1 . . 107.46(18) ?
O3 C2 C1 . . 108.9(2) ?
O4 C2 C3 . . 108.0(2) ?
O3 C2 C3 . . 103.59(17) ?
C1 C2 C3 . . 118.04(19) ?
C18 C19 C14 . . 120.0(2) ?
C18 C19 H19 . . 120.0 ?
C14 C19 H19 . . 120.0 ?
O6 C13 N5 . . 121.9(2) ?
O6 C13 C14 . . 122.0(2) ?
N5 C13 C14 . . 116.1(2) ?
O2 C3 C2 . . 114.78(19) ?
O2 C3 C4 . . 116.9(2) ?
C2 C3 C4 . . 97.00(18) ?
O2 C3 H3 . . 109.2 ?
C2 C3 H3 . . 109.2 ?
C4 C3 H3 . . 109.2 ?
N3 C12 N4 . . 128.3(2) ?
N3 C12 H12 . . 115.9 ?
N4 C12 H12 . . 115.9 ?
C17 C16 C15 . . 119.9(2) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C19 C14 C15 . . 119.5(2) ?
C19 C14 C13 . . 116.8(2) ?
C15 C14 C13 . . 123.7(2) ?
O5 C4 C5 . . 110.92(18) ?
O5 C4 C3 . . 108.70(19) ?
C5 C4 C3 . . 99.6(2) ?
O5 C4 H4 . . 112.3 ?
C5 C4 H4 . . 112.3 ?
C3 C4 H4 . . 112.3 ?
O1 C1 C2 . . 110.50(19) ?
O1 C1 H1A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.1 ?
O5 C6 O4 . . 111.02(19) ?
O5 C6 C7 . . 108.6(2) ?
O4 C6 C7 . . 109.1(2) ?
O5 C6 H6 . . 109.4 ?
O4 C6 H6 . . 109.4 ?
C7 C6 H6 . . 109.4 ?
O3 C5 N1 . . 108.82(19) ?
O3 C5 C4 . . 105.31(18) ?
N1 C5 C4 . . 113.35(19) ?
O3 C5 H5 . . 109.7 ?
N1 C5 H5 . . 109.7 ?
C4 C5 H5 . . 109.7 ?
C19 C18 C17 . . 120.4(3) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C16 C17 C18 . . 120.1(2) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
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 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 C2 . 1.433(3) ?
O3 C5 . 1.433(3) ?
O4 C2 . 1.426(3) ?
O4 C6 . 1.430(3) ?
O2 C3 . 1.408(3) ?
O2 H2 . 0.84 ?
O5 C6 . 1.428(3) ?
O5 C4 . 1.432(3) ?
O6 C13 . 1.217(3) ?
O1 C1 . 1.405(3) ?
O1 H1 . 0.84 ?
N1 C8 . 1.377(3) ?
N1 C9 . 1.379(3) ?
N1 C5 . 1.455(3) ?
N3 C9 . 1.333(3) ?
N3 C12 . 1.338(3) ?
N2 C8 . 1.312(3) ?
N2 C10 . 1.387(3) ?
N5 C13 . 1.381(3) ?
N5 C11 . 1.393(3) ?
N5 H20 . 0.86(3) ?
N4 C11 . 1.343(3) ?
N4 C12 . 1.344(3) ?
C10 C11 . 1.397(3) ?
C10 C9 . 1.397(3) ?
C8 H8 . 0.95 ?
C15 C16 . 1.395(4) ?
C15 C14 . 1.399(3) ?
C15 H15 . 0.95 ?
C2 C1 . 1.516(3) ?
C2 C3 . 1.531(3) ?
C19 C18 . 1.384(4) ?
C19 C14 . 1.398(4) ?
C19 H19 . 0.95 ?
C13 C14 . 1.503(3) ?
C3 C4 . 1.539(3) ?
C3 H3 . 1.0 ?
C12 H12 . 0.95 ?
C16 C17 . 1.388(4) ?
C16 H16 . 0.95 ?
C4 C5 . 1.535(4) ?
C4 H4 . 1.0 ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C6 C7 . 1.500(4) ?
C6 H6 . 1.0 ?
C5 H5 . 1.0 ?
C18 C17 . 1.389(4) ?
C18 H18 . 0.95 ?
C17 H17 . 0.95 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
