#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238867.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238867
loop_
_publ_author_name
'Al-Abdullah, Ebtehal S.'
'Al-Tuwaijri, Hanaa M.'
'El-Emam, Ali A.'
'Chidan Kumar, C. S.'
'Fun, Hoong-Kun'
_publ_section_title
;
3-(Adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-ethyl-1H-1,2,4-triazole-5(4H)-thione
;
_journal_coeditor_code HB7161
_journal_issue 12
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o1813
_journal_page_last o1814
_journal_paper_doi 10.1107/S1600536813031127
_journal_volume 69
_journal_year 2013
_chemical_formula_iupac 'C26 H37 N5 S'
_chemical_formula_moiety 'C26 H37 N5 S'
_chemical_formula_sum 'C26 H37 N5 S'
_chemical_formula_weight 451.67
_chemical_name_systematic
3-(Adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-ethyl-1H-1,2,4-triazole-5(4H)-thione
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_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
_cell_angle_alpha 89.9740(10)
_cell_angle_beta 77.6190(10)
_cell_angle_gamma 70.8420(10)
_cell_formula_units_Z 2
_cell_length_a 10.5618(2)
_cell_length_b 11.2123(2)
_cell_length_c 11.3084(2)
_cell_measurement_reflns_used 6190
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 69.33
_cell_measurement_theta_min 4.01
_cell_volume 1232.03(4)
_computing_cell_refinement 'SAINT (Bruker, 2009)'
_computing_data_collection 'APEX2 (Bruker, 2009)'
_computing_data_reduction 'SAINT (Bruker, 2009)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type 'Bruker APEXII CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0245
_diffrn_reflns_av_sigmaI/netI 0.0304
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 13169
_diffrn_reflns_theta_full 67.50
_diffrn_reflns_theta_max 67.50
_diffrn_reflns_theta_min 4.01
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 1.331
_exptl_absorpt_correction_T_max 0.6263
_exptl_absorpt_correction_T_min 0.4595
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2009)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.218
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 488
_exptl_crystal_size_max 0.69
_exptl_crystal_size_mid 0.51
_exptl_crystal_size_min 0.39
_refine_diff_density_max 0.218
_refine_diff_density_min -0.193
_refine_ls_extinction_coef 0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref 1.076
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 291
_refine_ls_number_reflns 4319
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.076
_refine_ls_R_factor_all 0.0429
_refine_ls_R_factor_gt 0.0403
_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/[\s^2^(Fo^2^)+(0.0605P)^2^+0.2192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1147
_refine_ls_wR_factor_ref 0.1167
_reflns_number_gt 3986
_reflns_number_total 4319
_reflns_threshold_expression I>2\s(I)
_iucr_refine_instructions_details
;
TITL HT7 in P-1
CELL 1.54178 10.5618 11.2123 11.3084 89.974 77.619 70.842
ZERR 2.00 0.0002 0.0002 0.0002 0.001 0.001 0.001
LATT 1
SFAC C H N S
UNIT 52 74 10 2
TEMP 23.000
SIZE 0.388 0.512 0.692
omit -4 135
L.S. 20
BOND $H
FMAP 2
PLAN 20
CONF
ACTA
SIZE 0.388 0.512 0.692
WGHT 0.060000 0.241900
WGHT 0.0605 0.2192
EXTI 0.003323
FVAR 0.88875
S1 4 0.226764 0.185269 0.138499 11.00000 0.05977 0.04216 =
0.09335 -0.00411 -0.00459 -0.01145
N1 3 -0.341699 0.236350 0.028123 11.00000 0.04356 0.04996 =
0.05043 0.00365 -0.00689 -0.01416
N2 3 -0.165397 0.166851 0.194353 11.00000 0.05654 0.03669 =
0.05292 0.00676 -0.01399 -0.01877
N3 3 -0.039071 0.292708 0.263579 11.00000 0.05681 0.03476 =
0.05687 0.00295 -0.01134 -0.01978
N4 3 -0.133375 0.407594 0.314098 11.00000 0.05382 0.03874 =
0.05524 0.00238 -0.00968 -0.01998
N5 3 0.065282 0.427390 0.225921 11.00000 0.04755 0.03686 =
0.06071 0.00291 -0.01120 -0.01781
C1 1 -0.318814 0.166686 -0.271785 11.00000 0.08120 0.05590 =
0.06605 -0.00180 -0.01427 -0.01994
AFIX 43
H1A 2 -0.291277 0.080710 -0.259820 11.00000 -1.20000
AFIX 0
C2 1 -0.284780 0.205617 -0.385711 11.00000 0.10220 0.07374 =
0.05679 -0.01156 -0.00348 -0.02821
AFIX 43
H2A 2 -0.233121 0.145656 -0.449789 11.00000 -1.20000
AFIX 0
C3 1 -0.326008 0.332208 -0.406555 11.00000 0.08409 0.07754 =
0.05639 0.00627 -0.01489 -0.03682
AFIX 43
H3A 2 -0.302840 0.357918 -0.484041 11.00000 -1.20000
AFIX 0
C4 1 -0.401894 0.419868 -0.311052 11.00000 0.07003 0.05919 =
0.07102 0.00707 -0.02132 -0.02350
AFIX 43
H4A 2 -0.431026 0.505580 -0.324022 11.00000 -1.20000
AFIX 0
C5 1 -0.435053 0.381583 -0.196305 11.00000 0.05562 0.05967 =
0.06090 -0.00487 -0.01030 -0.01642
AFIX 43
H5A 2 -0.485910 0.441912 -0.132322 11.00000 -1.20000
AFIX 0
C6 1 -0.393578 0.253963 -0.174704 11.00000 0.04631 0.06080 =
0.05733 0.00178 -0.01519 -0.02004
C7 1 -0.428029 0.212798 -0.049120 11.00000 0.05197 0.06911 =
0.06142 0.00680 -0.01318 -0.02575
AFIX 23
H7A 2 -0.524021 0.258128 -0.012218 11.00000 -1.20000
H7B 2 -0.415388 0.123115 -0.054167 11.00000 -1.20000
AFIX 0
C8 1 -0.393678 0.218423 0.154578 11.00000 0.05025 0.06433 =
0.05522 0.00598 -0.00517 -0.02304
AFIX 23
H8A 2 -0.389972 0.131250 0.162362 11.00000 -1.20000
H8B 2 -0.488892 0.272659 0.181310 11.00000 -1.20000
AFIX 0
C9 1 -0.308211 0.249997 0.233225 11.00000 0.05504 0.06110 =
0.05004 0.00064 -0.00243 -0.02303
AFIX 23
H9A 2 -0.313113 0.337583 0.226608 11.00000 -1.20000
H9B 2 -0.344082 0.239255 0.317479 11.00000 -1.20000
AFIX 0
C10 1 -0.110602 0.177451 0.066778 11.00000 0.04445 0.05012 =
0.05560 0.00051 -0.00699 -0.00918
AFIX 23
H10A 2 -0.017852 0.117514 0.041545 11.00000 -1.20000
H10B 2 -0.106409 0.261973 0.055669 11.00000 -1.20000
AFIX 0
C11 1 -0.199994 0.151355 -0.010956 11.00000 0.04891 0.06024 =
0.05504 -0.00575 -0.00726 -0.00877
AFIX 23
H11A 2 -0.164109 0.162441 -0.095111 11.00000 -1.20000
H11B 2 -0.197576 0.064334 -0.005389 11.00000 -1.20000
AFIX 0
C12 1 -0.077200 0.177194 0.270781 11.00000 0.06679 0.03722 =
0.05936 0.01232 -0.01994 -0.02471
AFIX 23
H12A 2 0.006610 0.104421 0.250594 11.00000 -1.20000
H12B 2 -0.122168 0.172885 0.354211 11.00000 -1.20000
AFIX 0
C13 1 0.083955 0.300565 0.208955 11.00000 0.05523 0.03847 =
0.05716 0.00475 -0.01509 -0.01842
C14 1 0.176694 0.476758 0.177873 11.00000 0.04787 0.04504 =
0.08746 0.00193 -0.00886 -0.02116
AFIX 23
H14A 2 0.261816 0.419733 0.193721 11.00000 -1.20000
H14B 2 0.157110 0.558336 0.220058 11.00000 -1.20000
AFIX 0
C15 1 0.195515 0.491653 0.043708 11.00000 0.07169 0.06144 =
0.08622 0.01120 0.00446 -0.02505
AFIX 137
H15A 2 0.260934 0.534437 0.018538 11.00000 -1.50000
H15B 2 0.108961 0.540373 0.026364 11.00000 -1.50000
H15C 2 0.228667 0.409659 0.000574 11.00000 -1.50000
AFIX 0
C16 1 -0.068219 0.488476 0.289828 11.00000 0.04893 0.03744 =
0.05198 0.00410 -0.01382 -0.01763
C17 1 -0.134673 0.627621 0.331068 11.00000 0.04829 0.03514 =
0.05805 0.00266 -0.01447 -0.01520
C18 1 -0.071996 0.663315 0.430947 11.00000 0.06588 0.04556 =
0.06318 0.00192 -0.02505 -0.01490
AFIX 23
H18A 2 -0.083281 0.612244 0.499089 11.00000 -1.20000
H18B 2 0.025708 0.646411 0.399732 11.00000 -1.20000
AFIX 0
C19 1 -0.143252 0.804083 0.473364 11.00000 0.08160 0.05018 =
0.07468 -0.00943 -0.02918 -0.01872
AFIX 13
H19A 2 -0.101466 0.826378 0.535713 11.00000 -1.20000
AFIX 0
C20 1 -0.126303 0.883830 0.366217 11.00000 0.07869 0.03777 =
0.09976 -0.00299 -0.01508 -0.02299
AFIX 23
H20A 2 -0.169168 0.972944 0.393274 11.00000 -1.20000
H20B 2 -0.029235 0.867837 0.332351 11.00000 -1.20000
AFIX 0
C21 1 -0.192108 0.851629 0.270039 11.00000 0.08308 0.04086 =
0.07414 0.01376 -0.01960 -0.01369
AFIX 13
H21A 2 -0.181597 0.904231 0.201864 11.00000 -1.20000
AFIX 0
C22 1 -0.343795 0.876741 0.322565 11.00000 0.07416 0.05025 =
0.10612 0.00367 -0.03376 -0.00295
AFIX 23
H22A 2 -0.386057 0.856217 0.260822 11.00000 -1.20000
H22B 2 -0.389341 0.965658 0.349524 11.00000 -1.20000
AFIX 0
C23 1 -0.360110 0.796236 0.428928 11.00000 0.05247 0.05182 =
0.10445 -0.00684 -0.00340 -0.01000
AFIX 13
H23A 2 -0.458248 0.812395 0.462785 11.00000 -1.20000
AFIX 0
C24 1 -0.289464 0.655448 0.384661 11.00000 0.05262 0.05003 =
0.09101 -0.00136 -0.00886 -0.01944
AFIX 23
H24A 2 -0.331729 0.634203 0.323265 11.00000 -1.20000
H24B 2 -0.301402 0.603565 0.452009 11.00000 -1.20000
AFIX 0
C25 1 -0.295747 0.829297 0.526288 11.00000 0.08959 0.05226 =
0.07627 -0.00859 -0.00058 -0.01305
AFIX 23
H25A 2 -0.307065 0.778393 0.594559 11.00000 -1.20000
H25B 2 -0.340940 0.917797 0.555009 11.00000 -1.20000
AFIX 0
C26 1 -0.121172 0.712243 0.225116 11.00000 0.06988 0.04460 =
0.05875 0.00708 -0.01804 -0.01639
AFIX 23
H26A 2 -0.024620 0.696915 0.189426 11.00000 -1.20000
H26B 2 -0.162721 0.691383 0.162971 11.00000 -1.20000
HKLF 4 1 1 0 0 0 -1 0 0 0 -1
REM HA7 in P-1
REM R1 = 0.0403 for 3986 Fo > 4sig(Fo) and 0.0428 for all 4319 data
REM 291 parameters refined using 0 restraints
END
WGHT 0.0605 0.2192
REM Highest difference peak 0.218, deepest hole -0.193, 1-sigma level 0.033
Q1 1 -0.0977 0.5574 0.3074 11.00000 0.05 0.22
Q2 1 -0.2077 0.6437 0.3534 11.00000 0.05 0.19
Q3 1 0.1776 0.2452 0.2165 11.00000 0.05 0.18
Q4 1 0.0844 0.3601 0.2230 11.00000 0.05 0.16
Q5 1 -0.1072 0.6425 0.3800 11.00000 0.05 0.16
Q6 1 -0.0014 0.4625 0.2313 11.00000 0.05 0.16
Q7 1 0.1579 0.1692 0.1631 11.00000 0.05 0.15
Q8 1 -0.1274 0.6609 0.2772 11.00000 0.05 0.14
Q9 1 -0.1717 0.0994 0.1921 11.00000 0.05 0.14
Q10 1 0.0578 0.1138 0.2133 11.00000 0.05 0.14
Q11 1 -0.2191 0.4261 0.3274 11.00000 0.05 0.14
Q12 1 -0.4505 0.3174 -0.1956 11.00000 0.05 0.13
Q13 1 -0.3223 0.3750 -0.3440 11.00000 0.05 0.13
Q14 1 -0.3460 0.2164 -0.2112 11.00000 0.05 0.12
Q15 1 -0.1581 0.7819 0.2446 11.00000 0.05 0.12
Q16 1 -0.2602 0.8559 0.2983 11.00000 0.05 0.12
Q17 1 -0.3777 0.3164 -0.1761 11.00000 0.05 0.11
Q18 1 -0.2336 0.1876 0.2143 11.00000 0.05 0.11
Q19 1 -0.0995 0.4416 0.3367 11.00000 0.05 0.11
Q20 1 -0.1689 0.8629 0.3234 11.00000 0.05 0.11
;
_cod_data_source_file hb7161.cif
_cod_data_source_block I
_cod_database_code 2238867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.22677(5) 0.18527(4) 0.13850(5) 0.06851(17) Uani d . 1 1
N N1 -0.34170(12) 0.23635(12) 0.02812(11) 0.0489(3) Uani d . 1 1
N N2 -0.16540(13) 0.16685(11) 0.19435(11) 0.0477(3) Uani d . 1 1
N N3 -0.03907(13) 0.29271(11) 0.26359(12) 0.0486(3) Uani d . 1 1
N N4 -0.13337(13) 0.40759(11) 0.31410(11) 0.0485(3) Uani d . 1 1
N N5 0.06528(12) 0.42739(11) 0.22592(12) 0.0476(3) Uani d . 1 1
C C1 -0.3188(2) 0.16668(18) -0.27179(17) 0.0688(5) Uani d . 1 1
H H1A -0.2913 0.0807 -0.2598 0.083 Uiso calc R 1 1
C C2 -0.2848(2) 0.2056(2) -0.38571(18) 0.0802(6) Uani d . 1 1
H H2A -0.2331 0.1456 -0.4498 0.096 Uiso calc R 1 1
C C3 -0.3260(2) 0.3322(2) -0.40656(17) 0.0704(5) Uani d . 1 1
H H3A -0.3028 0.3579 -0.4841 0.084 Uiso calc R 1 1
C C4 -0.4019(2) 0.41987(18) -0.31105(17) 0.0654(4) Uani d . 1 1
H H4A -0.4310 0.5056 -0.3240 0.078 Uiso calc R 1 1
C C5 -0.43506(17) 0.38159(17) -0.19630(16) 0.0599(4) Uani d . 1 1
H H5A -0.4859 0.4419 -0.1323 0.072 Uiso calc R 1 1
C C6 -0.39358(15) 0.25397(16) -0.17470(15) 0.0537(4) Uani d . 1 1
C C7 -0.42804(17) 0.21280(18) -0.04912(16) 0.0594(4) Uani d . 1 1
H H7A -0.5240 0.2581 -0.0122 0.071 Uiso calc R 1 1
H H7B -0.4154 0.1231 -0.0542 0.071 Uiso calc R 1 1
C C8 -0.39368(16) 0.21841(17) 0.15458(15) 0.0567(4) Uani d . 1 1
H H8A -0.3900 0.1312 0.1624 0.068 Uiso calc R 1 1
H H8B -0.4889 0.2726 0.1813 0.068 Uiso calc R 1 1
C C9 -0.30821(16) 0.25001(16) 0.23323(15) 0.0560(4) Uani d . 1 1
H H9A -0.3131 0.3376 0.2266 0.067 Uiso calc R 1 1
H H9B -0.3441 0.2393 0.3175 0.067 Uiso calc R 1 1
C C10 -0.11059(15) 0.17746(15) 0.06677(14) 0.0524(4) Uani d . 1 1
H H10A -0.0178 0.1175 0.0415 0.063 Uiso calc R 1 1
H H10B -0.1064 0.2620 0.0557 0.063 Uiso calc R 1 1
C C11 -0.20000(16) 0.15135(17) -0.01097(16) 0.0578(4) Uani d . 1 1
H H11A -0.1641 0.1624 -0.0951 0.069 Uiso calc R 1 1
H H11B -0.1976 0.0643 -0.0054 0.069 Uiso calc R 1 1
C C12 -0.07720(17) 0.17719(14) 0.27078(15) 0.0517(4) Uani d . 1 1
H H12A 0.0066 0.1044 0.2506 0.062 Uiso calc R 1 1
H H12B -0.1222 0.1729 0.3542 0.062 Uiso calc R 1 1
C C13 0.08395(16) 0.30056(14) 0.20895(14) 0.0492(3) Uani d . 1 1
C C14 0.17668(16) 0.47676(15) 0.17788(17) 0.0597(4) Uani d . 1 1
H H14A 0.2618 0.4197 0.1937 0.072 Uiso calc R 1 1
H H14B 0.1571 0.5583 0.2201 0.072 Uiso calc R 1 1
C C15 0.1955(2) 0.49166(19) 0.04371(19) 0.0760(5) Uani d . 1 1
H H15A 0.2609 0.5345 0.0186 0.114 Uiso calc R 1 1
H H15B 0.1090 0.5404 0.0264 0.114 Uiso calc R 1 1
H H15C 0.2287 0.4097 0.0006 0.114 Uiso calc R 1 1
C C16 -0.06822(15) 0.48847(13) 0.28983(13) 0.0449(3) Uani d . 1 1
C C17 -0.13467(15) 0.62762(13) 0.33107(14) 0.0464(3) Uani d . 1 1
C C18 -0.07200(18) 0.66332(15) 0.43095(16) 0.0575(4) Uani d . 1 1
H H18A -0.0833 0.6123 0.4991 0.069 Uiso calc R 1 1
H H18B 0.0257 0.6464 0.3997 0.069 Uiso calc R 1 1
C C19 -0.1432(2) 0.80408(16) 0.47337(18) 0.0678(5) Uani d . 1 1
H H19A -0.1015 0.8264 0.5357 0.081 Uiso calc R 1 1
C C20 -0.1263(2) 0.88384(16) 0.3662(2) 0.0720(5) Uani d . 1 1
H H20A -0.1692 0.9730 0.3933 0.086 Uiso calc R 1 1
H H20B -0.0292 0.8678 0.3323 0.086 Uiso calc R 1 1
C C21 -0.1921(2) 0.85163(16) 0.27002(18) 0.0675(5) Uani d . 1 1
H H21A -0.1816 0.9042 0.2018 0.081 Uiso calc R 1 1
C C22 -0.3438(2) 0.87674(18) 0.3226(2) 0.0792(6) Uani d . 1 1
H H22A -0.3861 0.8562 0.2608 0.095 Uiso calc R 1 1
H H22B -0.3893 0.9657 0.3495 0.095 Uiso calc R 1 1
C C23 -0.36012(19) 0.79624(18) 0.4289(2) 0.0737(5) Uani d . 1 1
H H23A -0.4583 0.8124 0.4628 0.088 Uiso calc R 1 1
C C24 -0.28947(17) 0.65544(16) 0.38466(19) 0.0651(5) Uani d . 1 1
H H24A -0.3317 0.6342 0.3233 0.078 Uiso calc R 1 1
H H24B -0.3014 0.6036 0.4520 0.078 Uiso calc R 1 1
C C25 -0.2958(2) 0.82930(19) 0.5263(2) 0.0783(6) Uani d . 1 1
H H25A -0.3071 0.7784 0.5946 0.094 Uiso calc R 1 1
H H25B -0.3409 0.9178 0.5550 0.094 Uiso calc R 1 1
C C26 -0.12118(19) 0.71224(15) 0.22511(15) 0.0579(4) Uani d . 1 1
H H26A -0.0246 0.6969 0.1894 0.069 Uiso calc R 1 1
H H26B -0.1627 0.6914 0.1630 0.069 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0597(3) 0.0421(2) 0.0933(4) -0.01144(18) -0.0046(2) -0.0041(2)
N1 0.0435(6) 0.0499(7) 0.0504(7) -0.0141(5) -0.0069(5) 0.0036(5)
N2 0.0565(7) 0.0367(6) 0.0529(7) -0.0188(5) -0.0140(5) 0.0067(5)
N3 0.0568(7) 0.0347(6) 0.0569(7) -0.0198(5) -0.0113(5) 0.0030(5)
N4 0.0538(7) 0.0387(6) 0.0552(7) -0.0200(5) -0.0097(5) 0.0024(5)
N5 0.0475(6) 0.0368(6) 0.0607(8) -0.0178(5) -0.0112(5) 0.0029(5)
C1 0.0811(12) 0.0559(10) 0.0660(11) -0.0199(9) -0.0143(9) -0.0018(8)
C2 0.1022(15) 0.0737(13) 0.0568(11) -0.0282(11) -0.0035(10) -0.0116(9)
C3 0.0840(12) 0.0775(13) 0.0564(10) -0.0368(10) -0.0149(9) 0.0063(8)
C4 0.0700(11) 0.0592(10) 0.0710(12) -0.0235(9) -0.0213(9) 0.0071(8)
C5 0.0556(9) 0.0596(10) 0.0609(10) -0.0164(8) -0.0103(7) -0.0049(7)
C6 0.0463(8) 0.0607(9) 0.0573(9) -0.0200(7) -0.0152(6) 0.0018(7)
C7 0.0519(8) 0.0691(11) 0.0614(10) -0.0258(8) -0.0132(7) 0.0068(8)
C8 0.0502(8) 0.0644(10) 0.0552(9) -0.0231(7) -0.0052(7) 0.0060(7)
C9 0.0550(9) 0.0611(10) 0.0500(9) -0.0230(7) -0.0024(7) 0.0006(7)
C10 0.0444(7) 0.0501(8) 0.0556(9) -0.0092(6) -0.0070(6) 0.0005(6)
C11 0.0489(8) 0.0602(10) 0.0550(9) -0.0087(7) -0.0072(7) -0.0058(7)
C12 0.0667(9) 0.0372(7) 0.0594(9) -0.0247(7) -0.0200(7) 0.0123(6)
C13 0.0552(8) 0.0384(7) 0.0572(9) -0.0184(6) -0.0151(7) 0.0047(6)
C14 0.0478(8) 0.0450(8) 0.0874(12) -0.0212(7) -0.0089(8) 0.0019(7)
C15 0.0716(11) 0.0614(11) 0.0862(14) -0.0250(9) 0.0045(10) 0.0112(9)
C16 0.0489(7) 0.0374(7) 0.0520(8) -0.0176(6) -0.0138(6) 0.0041(6)
C17 0.0483(8) 0.0351(7) 0.0580(9) -0.0152(6) -0.0145(6) 0.0027(6)
C18 0.0659(10) 0.0455(8) 0.0632(10) -0.0149(7) -0.0251(8) 0.0019(7)
C19 0.0816(12) 0.0502(9) 0.0746(12) -0.0187(9) -0.0292(9) -0.0094(8)
C20 0.0787(12) 0.0377(8) 0.0997(15) -0.0230(8) -0.0151(10) -0.0030(8)
C21 0.0830(12) 0.0408(9) 0.0741(12) -0.0137(8) -0.0196(9) 0.0138(8)
C22 0.0741(12) 0.0502(10) 0.1061(16) -0.0029(9) -0.0337(11) 0.0037(10)
C23 0.0524(9) 0.0517(10) 0.1044(15) -0.0100(8) -0.0034(9) -0.0068(9)
C24 0.0525(9) 0.0500(9) 0.0910(13) -0.0194(7) -0.0088(8) -0.0014(8)
C25 0.0895(14) 0.0522(10) 0.0762(13) -0.0130(10) -0.0006(10) -0.0086(8)
C26 0.0698(10) 0.0446(8) 0.0587(10) -0.0164(7) -0.0180(8) 0.0071(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C8 N1 C11 108.65(12)
C8 N1 C7 110.90(12)
C11 N1 C7 110.90(13)
C12 N2 C10 113.10(12)
C12 N2 C9 114.96(12)
C10 N2 C9 110.90(12)
C13 N3 N4 112.98(11)
C13 N3 C12 126.34(13)
N4 N3 C12 120.67(12)
C16 N4 N3 104.98(12)
C13 N5 C16 108.38(12)
C13 N5 C14 120.92(13)
C16 N5 C14 130.70(12)
C2 C1 C6 120.65(18)
C2 C1 H1A 119.7
C6 C1 H1A 119.7
C1 C2 C3 120.97(18)
C1 C2 H2A 119.5
C3 C2 H2A 119.5
C4 C3 C2 118.94(18)
C4 C3 H3A 120.5
C2 C3 H3A 120.5
C3 C4 C5 120.39(18)
C3 C4 H4A 119.8
C5 C4 H4A 119.8
C4 C5 C6 120.91(16)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C1 C6 C5 118.12(16)
C1 C6 C7 121.14(16)
C5 C6 C7 120.73(15)
N1 C7 C6 112.00(13)
N1 C7 H7A 109.2
C6 C7 H7A 109.2
N1 C7 H7B 109.2
C6 C7 H7B 109.2
H7A C7 H7B 107.9
N1 C8 C9 110.02(13)
N1 C8 H8A 109.7
C9 C8 H8A 109.7
N1 C8 H8B 109.7
C9 C8 H8B 109.7
H8A C8 H8B 108.2
N2 C9 C8 109.63(13)
N2 C9 H9A 109.7
C8 C9 H9A 109.7
N2 C9 H9B 109.7
C8 C9 H9B 109.7
H9A C9 H9B 108.2
N2 C10 C11 110.69(13)
N2 C10 H10A 109.5
C11 C10 H10A 109.5
N2 C10 H10B 109.5
C11 C10 H10B 109.5
H10A C10 H10B 108.1
N1 C11 C10 110.90(13)
N1 C11 H11A 109.5
C10 C11 H11A 109.5
N1 C11 H11B 109.5
C10 C11 H11B 109.5
H11A C11 H11B 108.0
N2 C12 N3 116.03(12)
N2 C12 H12A 108.3
N3 C12 H12A 108.3
N2 C12 H12B 108.3
N3 C12 H12B 108.3
H12A C12 H12B 107.4
N3 C13 N5 103.43(13)
N3 C13 S1 128.88(11)
N5 C13 S1 127.69(12)
N5 C14 C15 112.60(15)
N5 C14 H14A 109.1
C15 C14 H14A 109.1
N5 C14 H14B 109.1
C15 C14 H14B 109.1
H14A C14 H14B 107.8
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N4 C16 N5 110.22(12)
N4 C16 C17 122.45(13)
N5 C16 C17 127.32(12)
C16 C17 C18 110.91(12)
C16 C17 C26 111.94(13)
C18 C17 C26 109.46(13)
C16 C17 C24 108.86(12)
C18 C17 C24 107.90(14)
C26 C17 C24 107.63(13)
C19 C18 C17 109.97(13)
C19 C18 H18A 109.7
C17 C18 H18A 109.7
C19 C18 H18B 109.7
C17 C18 H18B 109.7
H18A C18 H18B 108.2
C20 C19 C25 109.56(16)
C20 C19 C18 109.55(15)
C25 C19 C18 109.49(16)
C20 C19 H19A 109.4
C25 C19 H19A 109.4
C18 C19 H19A 109.4
C21 C20 C19 109.95(15)
C21 C20 H20A 109.7
C19 C20 H20A 109.7
C21 C20 H20B 109.7
C19 C20 H20B 109.7
H20A C20 H20B 108.2
C20 C21 C22 109.80(17)
C20 C21 C26 109.38(14)
C22 C21 C26 109.75(16)
C20 C21 H21A 109.3
C22 C21 H21A 109.3
C26 C21 H21A 109.3
C21 C22 C23 109.30(15)
C21 C22 H22A 109.8
C23 C22 H22A 109.8
C21 C22 H22B 109.8
C23 C22 H22B 109.8
H22A C22 H22B 108.3
C25 C23 C22 109.94(17)
C25 C23 C24 109.75(16)
C22 C23 C24 109.33(17)
C25 C23 H23A 109.3
C22 C23 H23A 109.3
C24 C23 H23A 109.3
C23 C24 C17 110.23(14)
C23 C24 H24A 109.6
C17 C24 H24A 109.6
C23 C24 H24B 109.6
C17 C24 H24B 109.6
H24A C24 H24B 108.1
C23 C25 C19 109.13(16)
C23 C25 H25A 109.9
C19 C25 H25A 109.9
C23 C25 H25B 109.9
C19 C25 H25B 109.9
H25A C25 H25B 108.3
C21 C26 C17 110.28(14)
C21 C26 H26A 109.6
C17 C26 H26A 109.6
C21 C26 H26B 109.6
C17 C26 H26B 109.6
H26A C26 H26B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C13 1.6694(16)
N1 C8 1.457(2)
N1 C11 1.4574(19)
N1 C7 1.471(2)
N2 C12 1.4299(19)
N2 C10 1.455(2)
N2 C9 1.460(2)
N3 C13 1.345(2)
N3 N4 1.3756(17)
N3 C12 1.4746(18)
N4 C16 1.3037(18)
N5 C13 1.3777(18)
N5 C16 1.3817(19)
N5 C14 1.463(2)
C1 C2 1.372(3)
C1 C6 1.382(2)
C1 H1A 0.9300
C2 C3 1.378(3)
C2 H2A 0.9300
C3 C4 1.374(3)
C3 H3A 0.9300
C4 C5 1.376(3)
C4 H4A 0.9300
C5 C6 1.390(2)
C5 H5A 0.9300
C6 C7 1.500(2)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.512(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.513(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9700
C12 H12B 0.9700
C14 C15 1.504(3)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C17 1.5119(19)
C17 C18 1.539(2)
C17 C26 1.540(2)
C17 C24 1.542(2)
C18 C19 1.534(2)
C18 H18A 0.9700
C18 H18B 0.9700
C19 C20 1.520(3)
C19 C25 1.523(3)
C19 H19A 0.9800
C20 C21 1.512(3)
C20 H20A 0.9700
C20 H20B 0.9700
C21 C22 1.515(3)
C21 C26 1.527(2)
C21 H21A 0.9800
C22 C23 1.518(3)
C22 H22A 0.9700
C22 H22B 0.9700
C23 C25 1.516(3)
C23 C24 1.539(2)
C23 H23A 0.9800
C24 H24A 0.9700
C24 H24B 0.9700
C25 H25A 0.9700
C25 H25B 0.9700
C26 H26A 0.9700
C26 H26B 0.9700
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
C13 N3 N4 C16 0.40(16)
C12 N3 N4 C16 -178.80(13)
C6 C1 C2 C3 -1.0(3)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 0.5(3)
C3 C4 C5 C6 -0.5(3)
C2 C1 C6 C5 1.1(3)
C2 C1 C6 C7 -178.28(18)
C4 C5 C6 C1 -0.3(3)
C4 C5 C6 C7 179.02(15)
C8 N1 C7 C6 169.20(14)
C11 N1 C7 C6 -69.99(18)
C1 C6 C7 N1 104.19(18)
C5 C6 C7 N1 -75.16(19)
C11 N1 C8 C9 60.95(17)
C7 N1 C8 C9 -176.91(14)
C12 N2 C9 C8 -172.94(12)
C10 N2 C9 C8 57.20(16)
N1 C8 C9 N2 -60.32(17)
C12 N2 C10 C11 173.70(12)
C9 N2 C10 C11 -55.46(16)
C8 N1 C11 C10 -59.08(18)
C7 N1 C11 C10 178.79(13)
N2 C10 C11 N1 56.68(18)
C10 N2 C12 N3 55.67(17)
C9 N2 C12 N3 -73.11(17)
C13 N3 C12 N2 -105.86(17)
N4 N3 C12 N2 73.21(18)
N4 N3 C13 N5 -0.21(16)
C12 N3 C13 N5 178.92(13)
N4 N3 C13 S1 179.12(11)
C12 N3 C13 S1 -1.7(2)
C16 N5 C13 N3 -0.04(16)
C14 N5 C13 N3 -179.29(14)
C16 N5 C13 S1 -179.39(12)
C14 N5 C13 S1 1.4(2)
C13 N5 C14 C15 77.74(18)
C16 N5 C14 C15 -101.32(19)
N3 N4 C16 N5 -0.41(15)
N3 N4 C16 C17 -179.14(13)
C13 N5 C16 N4 0.30(17)
C14 N5 C16 N4 179.45(15)
C13 N5 C16 C17 178.95(14)
C14 N5 C16 C17 -1.9(3)
N4 C16 C17 C18 109.96(16)
N5 C16 C17 C18 -68.55(19)
N4 C16 C17 C26 -127.47(15)
N5 C16 C17 C26 54.03(19)
N4 C16 C17 C24 -8.6(2)
N5 C16 C17 C24 172.88(15)
C16 C17 C18 C19 -178.70(14)
C26 C17 C18 C19 57.30(18)
C24 C17 C18 C19 -59.55(18)
C17 C18 C19 C20 -58.9(2)
C17 C18 C19 C25 61.3(2)
C25 C19 C20 C21 -59.28(19)
C18 C19 C20 C21 60.8(2)
C19 C20 C21 C22 59.44(19)
C19 C20 C21 C26 -61.1(2)
C20 C21 C22 C23 -59.6(2)
C26 C21 C22 C23 60.7(2)
C21 C22 C23 C25 60.2(2)
C21 C22 C23 C24 -60.4(2)
C25 C23 C24 C17 -60.1(2)
C22 C23 C24 C17 60.5(2)
C16 C17 C24 C23 179.36(15)
C18 C17 C24 C23 58.92(19)
C26 C17 C24 C23 -59.11(19)
C22 C23 C25 C19 -60.1(2)
C24 C23 C25 C19 60.2(2)
C20 C19 C25 C23 59.33(19)
C18 C19 C25 C23 -60.8(2)
C20 C21 C26 C17 59.6(2)
C22 C21 C26 C17 -60.88(19)
C16 C17 C26 C21 178.81(13)
C18 C17 C26 C21 -57.80(18)
C24 C17 C26 C21 59.22(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086213