#------------------------------------------------------------------------------
#$Date: 2023-08-05 12:20:04 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285490 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/25/7062523.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_7062523
loop_
_publ_author_name
'Durga Priyadharshini, R.'
'Sathishkumar, P. N.'
'Bensingh, M.'
'Bhuvanesh, N.'
'Vennila, K. N.'
'Karvembu, R.'
'Elango, Kuppanagounder P.'
_publ_section_title
;
 N,N′,N′′-Trisubstituted guanidine derivatives as
 DNA-intercalators: synthesis, crystal structures and biophysical
 investigations
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14185
_journal_page_last               14194
_journal_paper_doi               10.1039/D3NJ01327H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C20 H19 N3 O S'
_chemical_formula_sum            'C20 H19 N3 O S'
_chemical_formula_weight         349.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-08 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2629(10)
_cell_length_b                   12.0772(9)
_cell_length_c                   22.1882(16)
_cell_measurement_reflns_used    6974
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      26.261
_cell_measurement_theta_min      2.393
_cell_volume                     3554.1(5)
_computing_cell_refinement
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_reduction
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27648
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.393
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.3809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1056 before and 0.0548 after correction. The Ratio of minimum to maximum transmission is 0.8848. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.492
_exptl_crystal_size_min          0.458
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0349P)²+1.9463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2675
_reflns_number_total             3127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01327h2.cif
_cod_data_source_block           benbg1a
_cod_depositor_comments
'Adding full bibliography for 7062523--7062525.cif.'
_cod_database_code               7062523
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.901
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.45083(3) 0.84436(3) 0.31685(2) 0.02427(13) Uani 1 1 d . . . . .
O1 O 0.37277(8) 0.90588(9) 0.48418(5) 0.0228(3) Uani 1 1 d . . . . .
N1 N 0.34973(9) 0.74881(10) 0.42329(6) 0.0189(3) Uani 1 1 d . . . . .
N2 N 0.24645(10) 0.60017(10) 0.44317(6) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.203102 0.566310 0.466874 0.026 Uiso 1 1 calc R . . . .
N3 N 0.25956(10) 0.73782(11) 0.51496(6) 0.0223(3) Uani 1 1 d . . . . .
H3 H 0.288167 0.800241 0.526193 0.027 Uiso 1 1 calc R . . . .
C1 C 0.28497(11) 0.69764(12) 0.46123(7) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.38664(11) 0.84925(12) 0.43708(7) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.45019(11) 0.89755(12) 0.38907(7) 0.0188(3) Uani 1 1 d . . . . .
C4 C 0.51188(11) 0.98828(13) 0.39368(7) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.521399 1.028994 0.429869 0.026 Uiso 1 1 calc R . . . .
C5 C 0.55980(13) 1.01447(14) 0.33849(8) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.605743 1.074157 0.333639 0.033 Uiso 1 1 calc R . . . .
C6 C 0.53282(12) 0.94490(14) 0.29333(8) 0.0286(4) Uani 1 1 d . . . . .
H6 H 0.556759 0.951244 0.253128 0.034 Uiso 1 1 calc R . . . .
C7 C 0.27312(12) 0.54815(13) 0.38628(7) 0.0220(4) Uani 1 1 d . . . . .
H7A H 0.303656 0.604571 0.359552 0.026 Uiso 1 1 calc R . . . .
H7B H 0.210809 0.521168 0.366595 0.026 Uiso 1 1 calc R . . . .
C8 C 0.34615(11) 0.45195(13) 0.39278(7) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.35147(12) 0.37244(14) 0.34754(7) 0.0252(4) Uani 1 1 d . . . . .
H9 H 0.306339 0.376542 0.314366 0.030 Uiso 1 1 calc R . . . .
C10 C 0.42137(13) 0.28743(14) 0.35000(8) 0.0293(4) Uani 1 1 d . . . . .
H10 H 0.424267 0.234265 0.318490 0.035 Uiso 1 1 calc R . . . .
C11 C 0.48708(13) 0.27977(14) 0.39834(8) 0.0281(4) Uani 1 1 d . . . . .
H11 H 0.536133 0.222516 0.399794 0.034 Uiso 1 1 calc R . . . .
C12 C 0.48047(14) 0.35622(14) 0.44433(8) 0.0313(4) Uani 1 1 d . . . . .
H12 H 0.524020 0.350230 0.478165 0.038 Uiso 1 1 calc R . . . .
C13 C 0.41070(13) 0.44197(14) 0.44165(8) 0.0274(4) Uani 1 1 d . . . . .
H13 H 0.407205 0.494210 0.473595 0.033 Uiso 1 1 calc R . . . .
C14 C 0.18831(14) 0.68726(14) 0.55688(8) 0.0311(4) Uani 1 1 d . . . . .
H14A H 0.211680 0.612167 0.568067 0.037 Uiso 1 1 calc R . . . .
H14B H 0.121284 0.680512 0.537595 0.037 Uiso 1 1 calc R . . . .
C15 C 0.18070(12) 0.75888(14) 0.61254(8) 0.0260(4) Uani 1 1 d . . . . .
C16 C 0.23493(13) 0.73403(14) 0.66444(8) 0.0293(4) Uani 1 1 d . . . . .
H16 H 0.275893 0.669537 0.665599 0.035 Uiso 1 1 calc R . . . .
C17 C 0.22980(13) 0.80252(15) 0.71453(8) 0.0301(4) Uani 1 1 d . . . . .
H17 H 0.267070 0.784692 0.749783 0.036 Uiso 1 1 calc R . . . .
C18 C 0.17030(13) 0.89710(15) 0.71325(8) 0.0299(4) Uani 1 1 d . . . . .
H18 H 0.166732 0.944017 0.747549 0.036 Uiso 1 1 calc R . . . .
C19 C 0.11620(13) 0.92267(14) 0.66175(8) 0.0304(4) Uani 1 1 d . . . . .
H19 H 0.075596 0.987440 0.660647 0.037 Uiso 1 1 calc R . . . .
C20 C 0.12115(13) 0.85400(14) 0.61181(8) 0.0291(4) Uani 1 1 d . . . . .
H20 H 0.083561 0.871927 0.576694 0.035 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C3 91.27(8) . . ?
C2 N1 C1 120.16(13) . . ?
C1 N2 H2 118.5 . . ?
C1 N2 C7 123.01(13) . . ?
C7 N2 H2 118.5 . . ?
C1 N3 H3 117.2 . . ?
C1 N3 C14 125.61(14) . . ?
C14 N3 H3 117.2 . . ?
N2 C1 N1 117.13(14) . . ?
N3 C1 N1 123.51(14) . . ?
N3 C1 N2 119.36(14) . . ?
O1 C2 N1 128.65(14) . . ?
O1 C2 C3 117.76(13) . . ?
N1 C2 C3 113.58(13) . . ?
C2 C3 S1 121.66(11) . . ?
C4 C3 S1 111.32(12) . . ?
C4 C3 C2 126.99(14) . . ?
C3 C4 H4 123.8 . . ?
C3 C4 C5 112.46(15) . . ?
C5 C4 H4 123.8 . . ?
C4 C5 H5 123.8 . . ?
C6 C5 C4 112.48(15) . . ?
C6 C5 H5 123.8 . . ?
S1 C6 H6 123.8 . . ?
C5 C6 S1 112.46(13) . . ?
C5 C6 H6 123.8 . . ?
N2 C7 H7A 108.8 . . ?
N2 C7 H7B 108.8 . . ?
N2 C7 C8 113.78(13) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C9 C8 C7 119.46(14) . . ?
C13 C8 C7 122.28(14) . . ?
C13 C8 C9 118.23(15) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.16(16) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.09(15) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.23(16) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.64(16) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 120.60(15) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N3 C14 H14A 109.9 . . ?
N3 C14 H14B 109.9 . . ?
N3 C14 C15 108.94(13) . . ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
C16 C15 C14 121.25(16) . . ?
C16 C15 C20 118.71(16) . . ?
C20 C15 C14 120.00(16) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.63(16) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.13(16) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.67(16) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.14(16) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.71(16) . . ?
C19 C20 H20 119.6 . . ?
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
S1 C3 1.7264(15) . ?
S1 C6 1.7115(17) . ?
O1 C2 1.2624(18) . ?
N1 C1 1.3521(19) . ?
N1 C2 1.343(2) . ?
N2 H2 0.8800 . ?
N2 C1 1.344(2) . ?
N2 C7 1.4536(19) . ?
N3 H3 0.8800 . ?
N3 C1 1.330(2) . ?
N3 C14 1.460(2) . ?
C2 C3 1.478(2) . ?
C3 C4 1.371(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.415(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.356(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.519(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.511(2) . ?
C15 C16 1.390(2) . ?
C15 C20 1.394(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(2) . ?
C20 H20 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
_geom_hbond_publ_flag
N2 H2 O1 0.88 2.22 2.9722(17) 143.7 8_655 yes
N3 H3 O1 0.88 1.94 2.6155(17) 132.6 . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C3 C4 C5 -0.08(17) . . . . ?
O1 C2 C3 S1 -164.60(11) . . . . ?
O1 C2 C3 C4 13.3(2) . . . . ?
N1 C2 C3 S1 14.45(18) . . . . ?
N1 C2 C3 C4 -167.70(14) . . . . ?
N2 C7 C8 C9 158.05(14) . . . . ?
N2 C7 C8 C13 -24.0(2) . . . . ?
N3 C14 C15 C16 -98.16(18) . . . . ?
N3 C14 C15 C20 79.62(19) . . . . ?
C1 N1 C2 O1 3.3(2) . . . . ?
C1 N1 C2 C3 -175.65(13) . . . . ?
C1 N2 C7 C8 103.51(16) . . . . ?
C1 N3 C14 C15 -179.95(15) . . . . ?
C2 N1 C1 N2 176.34(13) . . . . ?
C2 N1 C1 N3 -4.8(2) . . . . ?
C2 C3 C4 C5 -178.12(14) . . . . ?
C3 S1 C6 C5 1.02(14) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 S1 -1.25(19) . . . . ?
C6 S1 C3 C2 177.64(13) . . . . ?
C6 S1 C3 C4 -0.52(12) . . . . ?
C7 N2 C1 N1 1.4(2) . . . . ?
C7 N2 C1 N3 -177.54(14) . . . . ?
C7 C8 C9 C10 175.94(15) . . . . ?
C7 C8 C13 C12 -176.30(15) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C8 C13 C12 1.6(2) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C10 C11 C12 C13 -1.8(3) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C13 C8 C9 C10 -2.1(2) . . . . ?
C14 N3 C1 N1 178.43(15) . . . . ?
C14 N3 C1 N2 -2.7(2) . . . . ?
C14 C15 C16 C17 177.86(15) . . . . ?
C14 C15 C20 C19 -177.69(15) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C15 C20 C19 0.1(2) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C15 -0.3(3) . . . . ?
C20 C15 C16 C17 0.1(2) . . . . ?
