#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/85/4118522.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_4118522
loop_
_publ_author_name
'Powner, Matthew W.'
'Zheng, Shao-Liang'
'Szostak, Jack W.'
_publ_section_title
;
 Multicomponent Assembly of Proposed DNA Precursors in Water
;
_journal_coden_ASTM              JACSAT
_journal_issue                   33
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13889
_journal_page_last               13895
_journal_paper_doi               10.1021/ja306176n
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C8 H10 N6 O S'
_chemical_formula_weight         238.28
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.434(5)
_cell_length_b                   11.857(3)
_cell_length_c                   4.9575(14)
_cell_measurement_reflns_used    5269
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      2.48
_cell_volume                     966.0(5)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8833
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.8656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0304
_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)+(0.0368P)²+0.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                2236
_reflns_number_total             2498
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja306176n_si_003.cif
_cod_data_source_block           MP2-092-3
_cod_database_code               4118522
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
S1 S -0.37272(2) -0.23949(3) -0.58107(15) 0.01446(10) Uani 1 1 d .
O1 O -0.05534(7) -0.17514(10) -0.9868(3) 0.0180(3) Uani 1 1 d .
N1 N -0.43488(9) -0.44649(14) -0.6411(4) 0.0201(4) Uani 1 1 d .
H1A H -0.4667(16) -0.411(2) -0.744(6) 0.033(7) Uiso 1 1 d .
H1B H -0.4376(14) -0.522(2) -0.619(6) 0.036(7) Uiso 1 1 d .
N2 N -0.32718(9) -0.42728(12) -0.3344(3) 0.0158(3) Uani 1 1 d .
N3 N -0.18802(8) -0.16725(12) -0.5845(4) 0.0169(3) Uani 1 1 d .
H3 H -0.1627(14) -0.120(2) -0.670(5) 0.025(7) Uiso 1 1 d .
N4 N -0.09896(9) -0.44380(13) -0.6636(3) 0.0163(3) Uani 1 1 d .
N5 N -0.19378(8) -0.35481(12) -0.4207(3) 0.0148(3) Uani 1 1 d .
N6 N -0.00574(9) -0.34773(14) -1.0956(4) 0.0177(3) Uani 1 1 d .
H6A H 0.0173(15) -0.321(2) -1.224(6) 0.027(7) Uiso 1 1 d .
H6B H -0.0059(13) -0.4157(19) -1.071(6) 0.024(6) Uiso 1 1 d .
C1 C -0.37857(10) -0.38707(14) -0.5082(4) 0.0148(4) Uani 1 1 d .
C2 C -0.26828(10) -0.34200(14) -0.2548(4) 0.0147(4) Uani 1 1 d .
H2 H -0.2542 -0.3520 -0.0599 0.018 Uiso 1 1 calc R
C3 C -0.30268(10) -0.22211(15) -0.3001(4) 0.0137(3) Uani 1 1 d .
H3A H -0.3343 -0.1992 -0.1367 0.016 Uiso 1 1 calc R
C4 C -0.23744(10) -0.13363(14) -0.3545(4) 0.0155(4) Uani 1 1 d .
H4B H -0.2635 -0.0600 -0.3918 0.019 Uiso 1 1 calc R
H4A H -0.2024 -0.1251 -0.1932 0.019 Uiso 1 1 calc R
C5 C -0.15981(9) -0.27440(13) -0.5859(5) 0.0141(3) Uani 1 1 d .
C6 C -0.10099(11) -0.33006(14) -0.7354(4) 0.0148(4) Uani 1 1 d .
C7 C -0.15419(11) -0.45459(15) -0.4763(4) 0.0166(4) Uani 1 1 d .
H7 H -0.1658 -0.5238 -0.3877 0.020 Uiso 1 1 calc R
C8 C -0.05270(10) -0.27962(15) -0.9467(4) 0.0147(4) 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'
S S 0.1246 0.1234 '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
C1 S1 C3 89.44(8)
C1 N1 H1A 118.0(17)
C1 N1 H1B 119.9(17)
H1A N1 H1B 122(2)
C1 N2 C2 110.99(15)
C5 N3 C4 116.92(17)
C5 N3 H3 117.8(17)
C4 N3 H3 120.3(17)
C7 N4 C6 105.04(15)
C5 N5 C7 106.53(15)
C5 N5 C2 126.48(14)
C7 N5 C2 126.06(15)
C8 N6 H6A 118.2(17)
C8 N6 H6B 120.9(18)
H6A N6 H6B 120(3)
N2 C1 N1 125.76(17)
N2 C1 S1 117.29(13)
N1 C1 S1 116.95(14)
N2 C2 N5 109.13(15)
N2 C2 C3 110.88(14)
N5 C2 C3 108.38(14)
N2 C2 H2 109.5
N5 C2 H2 109.5
C3 C2 H2 109.5
C4 C3 C2 113.66(14)
C4 C3 S1 112.82(13)
C2 C3 S1 103.80(12)
C4 C3 H3A 108.8
C2 C3 H3A 108.8
S1 C3 H3A 108.8
N3 C4 C3 110.03(15)
N3 C4 H4B 109.7
C3 C4 H4B 109.7
N3 C4 H4A 109.7
C3 C4 H4A 109.7
H4B C4 H4A 108.2
N3 C5 N5 120.60(17)
N3 C5 C6 133.60(18)
N5 C5 C6 105.75(15)
C5 C6 N4 109.93(16)
C5 C6 C8 125.05(16)
N4 C6 C8 124.90(16)
N4 C7 N5 112.74(17)
N4 C7 H7 123.6
N5 C7 H7 123.6
O1 C8 N6 121.87(18)
O1 C8 C6 120.30(16)
N6 C8 C6 117.84(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7893(18)
S1 C3 1.8188(19)
O1 C8 1.255(2)
N1 C1 1.337(2)
N1 H1A 0.84(3)
N1 H1B 0.90(3)
N2 C1 1.297(2)
N2 C2 1.454(2)
N3 C5 1.352(2)
N3 C4 1.456(3)
N3 H3 0.81(2)
N4 C7 1.305(2)
N4 C6 1.395(2)
N5 C5 1.375(2)
N5 C7 1.378(2)
N5 C2 1.483(2)
N6 C8 1.339(2)
N6 H6A 0.80(3)
N6 H6B 0.82(2)
C2 C3 1.546(2)
C2 H2 1.0000
C3 C4 1.524(2)
C3 H3A 1.0000
C4 H4B 0.9900
C4 H4A 0.9900
C5 C6 1.385(3)
C6 C8 1.444(3)
C7 H7 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O1 0.90(3) 1.93(3) 2.821(2) 167(3) 3_445
N1 H1A O1 0.84(3) 2.15(3) 2.989(2) 176(3) 4_445
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
C2 N2 C1 N1 172.81(17)
C2 N2 C1 S1 -6.13(19)
C3 S1 C1 N2 -10.20(15)
C3 S1 C1 N1 170.76(15)
C1 N2 C2 N5 -95.81(17)
C1 N2 C2 C3 23.5(2)
C5 N5 C2 N2 121.39(19)
C7 N5 C2 N2 -46.1(2)
C5 N5 C2 C3 0.5(2)
C7 N5 C2 C3 -166.93(16)
N2 C2 C3 C4 -152.02(15)
N5 C2 C3 C4 -32.3(2)
N2 C2 C3 S1 -29.09(18)
N5 C2 C3 S1 90.67(14)
C1 S1 C3 C4 144.51(13)
C1 S1 C3 C2 21.02(12)
C5 N3 C4 C3 -48.1(2)
C2 C3 C4 N3 56.1(2)
S1 C3 C4 N3 -61.69(17)
C4 N3 C5 N5 17.1(3)
C4 N3 C5 C6 -166.0(2)
C7 N5 C5 N3 177.83(18)
C2 N5 C5 N3 8.4(3)
C7 N5 C5 C6 0.2(2)
C2 N5 C5 C6 -169.25(16)
N3 C5 C6 N4 -177.0(2)
N5 C5 C6 N4 0.2(2)
N3 C5 C6 C8 -0.8(4)
N5 C5 C6 C8 176.41(16)
C7 N4 C6 C5 -0.6(2)
C7 N4 C6 C8 -176.77(18)
C6 N4 C7 N5 0.7(2)
C5 N5 C7 N4 -0.6(2)
C2 N5 C7 N4 168.90(16)
C5 C6 C8 O1 8.4(3)
N4 C6 C8 O1 -176.01(16)
C5 C6 C8 N6 -171.68(18)
N4 C6 C8 N6 3.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139121384
