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The asymmetric unit of the title compound, C
16H
19Cl
2N
3OS, contains two crystallographically independent molecules, which have almost identical conformations. The dihydropyrimidine ring adopts a boat conformation in both molecules. N—H
O and N—H
S hydrogen bonds stabilize the crystal packing. The crystal is an inversion twin.
Supporting information
CCDC reference: 642926
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.085
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.03 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.23 Ratio
Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 6232
Count of symmetry unique reflns 3221
Completeness (_total/calc) 193.48%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 3011
Fraction of Friedel pairs measured 0.935
Are heavy atom types Z>Si present yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT792_ALERT_1_G Check the Absolute Configuration of C4 = ... R
PLAT792_ALERT_1_G Check the Absolute Configuration of C4' = ... R
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
5 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
4-(2,4-Dichlorophenyl)-5-(
N,
N-diethylcarbamoyl)-6-methyl-3,4-dihydropyrimidine- 2(1
H)-thione
top
Crystal data top
C16H19Cl2N3OS | F(000) = 1552 |
Mr = 372.30 | Dx = 1.391 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 6069 reflections |
a = 11.7548 (11) Å | θ = 2.2–27.8° |
b = 14.4443 (14) Å | µ = 0.49 mm−1 |
c = 20.946 (2) Å | T = 293 K |
V = 3556.5 (6) Å3 | Block, colorless |
Z = 8 | 0.20 × 0.15 × 0.10 mm |
Data collection top
Bruker SMART APEX CCD Area Detector diffractometer | 5875 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω scans | h = −13→13 |
24169 measured reflections | k = −17→17 |
6232 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0505P)2 + 0.7727P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
6232 reflections | Δρmax = 0.29 e Å−3 |
432 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: Flack, 1983 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.62 (4) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.70019 (6) | 0.55216 (5) | 0.31802 (4) | 0.05636 (19) | |
Cl2 | 0.30260 (8) | 0.69149 (6) | 0.24106 (4) | 0.0740 (3) | |
S1 | 0.40869 (6) | 0.13861 (5) | 0.25445 (3) | 0.04689 (16) | |
O32 | 0.76362 (15) | 0.36475 (14) | 0.41985 (9) | 0.0488 (5) | |
N1 | 0.43228 (19) | 0.23839 (15) | 0.35869 (9) | 0.0372 (4) | |
H1N | 0.371 (2) | 0.2042 (17) | 0.3742 (11) | 0.029 (6)* | |
N5 | 0.55474 (19) | 0.27397 (15) | 0.27857 (11) | 0.0376 (5) | |
H5N | 0.586 (2) | 0.2611 (18) | 0.2452 (14) | 0.035 (7)* | |
N33 | 0.63231 (17) | 0.45165 (14) | 0.46899 (10) | 0.0377 (4) | |
C2 | 0.4966 (2) | 0.28904 (16) | 0.40241 (11) | 0.0340 (5) | |
C3 | 0.57658 (19) | 0.34748 (16) | 0.38161 (11) | 0.0317 (5) | |
C4 | 0.59031 (19) | 0.35935 (15) | 0.31004 (11) | 0.0325 (5) | |
H4 | 0.6707 | 0.3707 | 0.3004 | 0.039* | |
C6 | 0.4689 (2) | 0.22243 (16) | 0.29845 (11) | 0.0346 (5) | |
C7 | 0.5199 (2) | 0.44274 (16) | 0.28767 (10) | 0.0333 (5) | |
C8 | 0.4110 (2) | 0.43294 (18) | 0.26310 (12) | 0.0403 (5) | |
H8 | 0.3822 | 0.3738 | 0.2564 | 0.048* | |
C9 | 0.3445 (2) | 0.50803 (19) | 0.24840 (14) | 0.0483 (6) | |
H9 | 0.2718 | 0.4997 | 0.2319 | 0.058* | |
C10 | 0.3862 (2) | 0.59539 (19) | 0.25825 (13) | 0.0475 (6) | |
C11 | 0.4949 (2) | 0.60884 (18) | 0.28046 (12) | 0.0451 (6) | |
H11 | 0.5235 | 0.6683 | 0.2861 | 0.054* | |
C12 | 0.5610 (2) | 0.53238 (18) | 0.29420 (11) | 0.0387 (5) | |
C21 | 0.4710 (3) | 0.2660 (2) | 0.47070 (12) | 0.0466 (6) | |
H21A | 0.3994 | 0.2928 | 0.4826 | 0.070* | |
H21B | 0.5300 | 0.2905 | 0.4976 | 0.070* | |
H21C | 0.4674 | 0.2000 | 0.4757 | 0.070* | |
C31 | 0.66356 (19) | 0.38949 (16) | 0.42494 (11) | 0.0334 (5) | |
C34 | 0.7168 (3) | 0.4796 (2) | 0.51658 (14) | 0.0522 (7) | |
H34A | 0.6995 | 0.5417 | 0.5312 | 0.063* | |
H34B | 0.7914 | 0.4808 | 0.4968 | 0.063* | |
C35 | 0.7194 (3) | 0.4156 (3) | 0.57275 (17) | 0.0782 (11) | |
H35A | 0.7527 | 0.3576 | 0.5603 | 0.117* | |
H35B | 0.6433 | 0.4053 | 0.5877 | 0.117* | |
H35C | 0.7640 | 0.4428 | 0.6063 | 0.117* | |
C36 | 0.5180 (2) | 0.48996 (18) | 0.47501 (14) | 0.0442 (6) | |
H36A | 0.4855 | 0.4694 | 0.5152 | 0.053* | |
H36B | 0.4711 | 0.4653 | 0.4409 | 0.053* | |
C37 | 0.5133 (3) | 0.5947 (2) | 0.4726 (2) | 0.0705 (10) | |
H37A | 0.5377 | 0.6156 | 0.4313 | 0.106* | |
H37B | 0.5625 | 0.6199 | 0.5048 | 0.106* | |
H37C | 0.4367 | 0.6150 | 0.4802 | 0.106* | |
Cl1' | 0.48498 (6) | −0.05823 (5) | 0.07621 (5) | 0.0729 (3) | |
Cl2' | 0.08761 (6) | −0.21173 (5) | 0.14123 (4) | 0.05690 (19) | |
S1' | 0.16956 (6) | 0.33529 (4) | 0.14824 (3) | 0.04515 (15) | |
O32' | 0.54086 (14) | 0.13619 (14) | −0.02589 (9) | 0.0476 (5) | |
N1' | 0.20952 (19) | 0.25839 (14) | 0.03565 (10) | 0.0353 (4) | |
H1'N | 0.158 (2) | 0.2871 (19) | 0.0232 (12) | 0.031 (7)* | |
N5' | 0.32649 (18) | 0.21187 (14) | 0.11578 (10) | 0.0366 (4) | |
H5'N | 0.342 (2) | 0.2134 (17) | 0.1564 (14) | 0.035 (7)* | |
N33' | 0.41261 (17) | 0.05501 (15) | −0.08152 (11) | 0.0410 (5) | |
C2' | 0.2745 (2) | 0.21177 (16) | −0.00993 (11) | 0.0333 (5) | |
C3' | 0.35242 (19) | 0.15017 (15) | 0.00966 (11) | 0.0322 (5) | |
C4' | 0.36421 (19) | 0.13057 (15) | 0.08050 (11) | 0.0321 (5) | |
H4' | 0.4447 | 0.1197 | 0.0901 | 0.039* | |
C6' | 0.2394 (2) | 0.26421 (15) | 0.09761 (11) | 0.0335 (5) | |
C7' | 0.2964 (2) | 0.04444 (16) | 0.09938 (11) | 0.0335 (5) | |
C8' | 0.1841 (2) | 0.05045 (17) | 0.11883 (12) | 0.0393 (5) | |
H8' | 0.1509 | 0.1087 | 0.1225 | 0.047* | |
C9' | 0.1190 (2) | −0.02733 (17) | 0.13309 (12) | 0.0413 (6) | |
H9' | 0.0437 | −0.0215 | 0.1462 | 0.050* | |
C10' | 0.1688 (2) | −0.11290 (17) | 0.12728 (11) | 0.0423 (6) | |
C11' | 0.2809 (2) | −0.12253 (18) | 0.11020 (14) | 0.0464 (6) | |
H11' | 0.3143 | −0.1808 | 0.1077 | 0.056* | |
C12' | 0.3430 (2) | −0.04402 (18) | 0.09690 (13) | 0.0423 (6) | |
C21' | 0.2514 (2) | 0.24011 (18) | −0.07759 (12) | 0.0434 (6) | |
H21D | 0.3080 | 0.2136 | −0.1051 | 0.065* | |
H21E | 0.2539 | 0.3064 | −0.0808 | 0.065* | |
H21F | 0.1774 | 0.2185 | −0.0901 | 0.065* | |
C31' | 0.44124 (19) | 0.11205 (16) | −0.03390 (11) | 0.0339 (5) | |
C34' | 0.4986 (2) | 0.0335 (2) | −0.12992 (14) | 0.0527 (7) | |
H34C | 0.4832 | −0.0274 | −0.1475 | 0.063* | |
H34D | 0.5728 | 0.0313 | −0.1097 | 0.063* | |
C35' | 0.5019 (4) | 0.1011 (3) | −0.1823 (2) | 0.0875 (12) | |
H35D | 0.5153 | 0.1619 | −0.1652 | 0.131* | |
H35E | 0.4305 | 0.1005 | −0.2046 | 0.131* | |
H35F | 0.5620 | 0.0853 | −0.2113 | 0.131* | |
C36' | 0.2987 (2) | 0.0152 (2) | −0.09109 (15) | 0.0505 (7) | |
H36C | 0.2698 | 0.0348 | −0.1323 | 0.061* | |
H36D | 0.2479 | 0.0391 | −0.0586 | 0.061* | |
C37' | 0.2981 (3) | −0.0892 (2) | −0.0883 (2) | 0.0807 (12) | |
H37D | 0.3188 | −0.1090 | −0.0461 | 0.121* | |
H37E | 0.3518 | −0.1133 | −0.1185 | 0.121* | |
H37F | 0.2234 | −0.1116 | −0.0983 | 0.121* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0477 (4) | 0.0456 (4) | 0.0758 (5) | −0.0127 (3) | −0.0108 (3) | −0.0016 (3) |
Cl2 | 0.0804 (5) | 0.0616 (5) | 0.0799 (6) | 0.0311 (4) | −0.0017 (4) | 0.0147 (4) |
S1 | 0.0607 (4) | 0.0420 (3) | 0.0381 (3) | −0.0094 (3) | −0.0069 (3) | 0.0012 (3) |
O32 | 0.0326 (9) | 0.0626 (11) | 0.0511 (11) | 0.0115 (8) | −0.0022 (8) | −0.0093 (9) |
N1 | 0.0390 (11) | 0.0377 (11) | 0.0348 (11) | −0.0065 (9) | 0.0043 (9) | −0.0003 (9) |
N5 | 0.0455 (12) | 0.0359 (11) | 0.0315 (10) | −0.0051 (9) | 0.0073 (10) | −0.0039 (9) |
N33 | 0.0315 (10) | 0.0416 (11) | 0.0400 (11) | 0.0006 (9) | −0.0010 (9) | −0.0082 (9) |
C2 | 0.0339 (12) | 0.0335 (12) | 0.0345 (12) | 0.0016 (10) | 0.0009 (10) | −0.0011 (10) |
C3 | 0.0313 (12) | 0.0318 (11) | 0.0320 (11) | 0.0045 (9) | 0.0012 (9) | −0.0005 (9) |
C4 | 0.0314 (12) | 0.0307 (11) | 0.0354 (12) | −0.0024 (9) | 0.0042 (9) | −0.0024 (10) |
C6 | 0.0382 (13) | 0.0301 (12) | 0.0354 (12) | 0.0008 (10) | −0.0004 (10) | 0.0036 (9) |
C7 | 0.0371 (13) | 0.0371 (12) | 0.0256 (11) | −0.0020 (10) | 0.0038 (9) | −0.0005 (9) |
C8 | 0.0389 (13) | 0.0423 (13) | 0.0397 (13) | −0.0049 (10) | −0.0028 (10) | 0.0040 (11) |
C9 | 0.0394 (14) | 0.0560 (16) | 0.0495 (15) | 0.0007 (12) | −0.0062 (12) | 0.0067 (14) |
C10 | 0.0554 (16) | 0.0475 (15) | 0.0396 (13) | 0.0146 (12) | 0.0000 (12) | 0.0064 (12) |
C11 | 0.0601 (17) | 0.0340 (13) | 0.0413 (13) | −0.0011 (12) | 0.0010 (12) | 0.0019 (11) |
C12 | 0.0455 (14) | 0.0391 (13) | 0.0315 (12) | −0.0038 (11) | −0.0004 (10) | −0.0024 (9) |
C21 | 0.0555 (16) | 0.0491 (15) | 0.0353 (13) | −0.0048 (13) | 0.0019 (12) | 0.0045 (11) |
C31 | 0.0319 (12) | 0.0360 (12) | 0.0324 (11) | 0.0042 (10) | 0.0024 (10) | 0.0030 (9) |
C34 | 0.0439 (15) | 0.0580 (17) | 0.0548 (16) | −0.0015 (13) | −0.0089 (12) | −0.0160 (14) |
C35 | 0.060 (2) | 0.122 (3) | 0.0523 (18) | −0.013 (2) | −0.0114 (15) | 0.013 (2) |
C36 | 0.0333 (13) | 0.0455 (14) | 0.0538 (16) | 0.0040 (11) | 0.0059 (11) | −0.0131 (12) |
C37 | 0.058 (2) | 0.0505 (18) | 0.103 (3) | 0.0110 (15) | 0.0085 (18) | −0.0114 (19) |
Cl1' | 0.0442 (4) | 0.0452 (4) | 0.1292 (8) | 0.0138 (3) | 0.0207 (4) | 0.0025 (4) |
Cl2' | 0.0655 (4) | 0.0422 (3) | 0.0631 (4) | −0.0145 (3) | 0.0025 (4) | 0.0046 (3) |
S1' | 0.0573 (4) | 0.0379 (3) | 0.0403 (3) | 0.0113 (3) | 0.0051 (3) | −0.0036 (3) |
O32' | 0.0287 (9) | 0.0599 (12) | 0.0541 (11) | −0.0088 (8) | 0.0024 (8) | −0.0139 (9) |
N1' | 0.0354 (11) | 0.0329 (11) | 0.0375 (11) | 0.0088 (9) | −0.0017 (9) | 0.0011 (8) |
N5' | 0.0435 (12) | 0.0338 (11) | 0.0327 (11) | 0.0042 (9) | −0.0083 (9) | −0.0045 (8) |
N33' | 0.0307 (10) | 0.0437 (12) | 0.0487 (12) | 0.0017 (8) | −0.0004 (9) | −0.0136 (9) |
C2' | 0.0324 (12) | 0.0317 (11) | 0.0358 (12) | −0.0038 (10) | −0.0011 (10) | −0.0003 (9) |
C3' | 0.0282 (11) | 0.0309 (11) | 0.0376 (12) | −0.0034 (9) | −0.0004 (9) | −0.0022 (9) |
C4' | 0.0305 (11) | 0.0318 (11) | 0.0341 (11) | 0.0036 (9) | −0.0029 (9) | −0.0030 (9) |
C6' | 0.0382 (12) | 0.0278 (11) | 0.0345 (12) | −0.0041 (10) | 0.0006 (10) | 0.0004 (9) |
C7' | 0.0359 (12) | 0.0321 (12) | 0.0324 (12) | 0.0018 (9) | −0.0028 (9) | −0.0005 (9) |
C8' | 0.0379 (13) | 0.0326 (12) | 0.0474 (14) | 0.0065 (10) | 0.0010 (11) | 0.0030 (10) |
C9' | 0.0381 (12) | 0.0406 (13) | 0.0451 (14) | 0.0005 (11) | 0.0017 (11) | 0.0039 (11) |
C10' | 0.0504 (15) | 0.0377 (13) | 0.0389 (13) | −0.0076 (11) | −0.0024 (11) | 0.0019 (10) |
C11' | 0.0478 (15) | 0.0325 (13) | 0.0588 (16) | 0.0053 (11) | 0.0027 (13) | 0.0032 (11) |
C12' | 0.0362 (13) | 0.0383 (13) | 0.0525 (15) | 0.0076 (10) | 0.0049 (11) | 0.0028 (11) |
C21' | 0.0477 (14) | 0.0440 (14) | 0.0384 (13) | 0.0050 (12) | −0.0001 (11) | 0.0037 (11) |
C31' | 0.0299 (12) | 0.0342 (12) | 0.0375 (12) | −0.0012 (10) | 0.0016 (10) | −0.0020 (10) |
C34' | 0.0423 (15) | 0.0631 (18) | 0.0529 (16) | 0.0090 (13) | 0.0049 (12) | −0.0208 (15) |
C35' | 0.077 (2) | 0.108 (3) | 0.078 (3) | 0.022 (2) | 0.028 (2) | 0.009 (2) |
C36' | 0.0346 (13) | 0.0531 (16) | 0.0639 (18) | −0.0011 (12) | −0.0051 (12) | −0.0213 (14) |
C37' | 0.065 (2) | 0.0558 (19) | 0.122 (3) | −0.0072 (16) | −0.017 (2) | −0.020 (2) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.735 (3) | Cl1'—C12' | 1.737 (3) |
Cl2—C10 | 1.738 (3) | Cl2'—C10' | 1.742 (3) |
S1—C6 | 1.678 (2) | S1'—C6' | 1.689 (2) |
O32—C31 | 1.234 (3) | O32'—C31' | 1.233 (3) |
N1—C6 | 1.353 (3) | N1'—C6' | 1.347 (3) |
N1—C2 | 1.395 (3) | N1'—C2' | 1.396 (3) |
N1—H1N | 0.93 (3) | N1'—H1'N | 0.78 (3) |
N5—C6 | 1.322 (3) | N5'—C6' | 1.328 (3) |
N5—C4 | 1.460 (3) | N5'—C4' | 1.457 (3) |
N5—H5N | 0.81 (3) | N5'—H5'N | 0.87 (3) |
N33—C31 | 1.339 (3) | N33'—C31' | 1.337 (3) |
N33—C36 | 1.459 (3) | N33'—C34' | 1.465 (3) |
N33—C34 | 1.463 (3) | N33'—C36' | 1.471 (3) |
C2—C3 | 1.337 (3) | C2'—C3' | 1.341 (3) |
C2—C21 | 1.499 (3) | C2'—C21' | 1.500 (3) |
C3—C31 | 1.496 (3) | C3'—C31' | 1.492 (3) |
C3—C4 | 1.517 (3) | C3'—C4' | 1.517 (3) |
C4—C7 | 1.534 (3) | C4'—C7' | 1.530 (3) |
C4—H4 | 0.9800 | C4'—H4' | 0.9800 |
C7—C8 | 1.388 (3) | C7'—C8' | 1.384 (3) |
C7—C12 | 1.388 (3) | C7'—C12' | 1.391 (3) |
C8—C9 | 1.372 (4) | C8'—C9' | 1.392 (4) |
C8—H8 | 0.9300 | C8'—H8' | 0.9300 |
C9—C10 | 1.369 (4) | C9'—C10' | 1.373 (4) |
C9—H9 | 0.9300 | C9'—H9' | 0.9300 |
C10—C11 | 1.374 (4) | C10'—C11' | 1.373 (4) |
C11—C12 | 1.380 (4) | C11'—C12' | 1.377 (4) |
C11—H11 | 0.9300 | C11'—H11' | 0.9300 |
C21—H21A | 0.9600 | C21'—H21D | 0.9600 |
C21—H21B | 0.9600 | C21'—H21E | 0.9600 |
C21—H21C | 0.9600 | C21'—H21F | 0.9600 |
C34—C35 | 1.497 (5) | C34'—C35' | 1.470 (5) |
C34—H34A | 0.9700 | C34'—H34C | 0.9700 |
C34—H34B | 0.9700 | C34'—H34D | 0.9700 |
C35—H35A | 0.9600 | C35'—H35D | 0.9600 |
C35—H35B | 0.9600 | C35'—H35E | 0.9600 |
C35—H35C | 0.9600 | C35'—H35F | 0.9600 |
C36—C37 | 1.515 (4) | C36'—C37' | 1.508 (4) |
C36—H36A | 0.9700 | C36'—H36C | 0.9700 |
C36—H36B | 0.9700 | C36'—H36D | 0.9700 |
C37—H37A | 0.9600 | C37'—H37D | 0.9600 |
C37—H37B | 0.9600 | C37'—H37E | 0.9600 |
C37—H37C | 0.9600 | C37'—H37F | 0.9600 |
| | | |
C6—N1—C2 | 122.0 (2) | C6'—N1'—C2' | 123.1 (2) |
C6—N1—H1N | 118.8 (15) | C6'—N1'—H1'N | 119.5 (19) |
C2—N1—H1N | 117.8 (15) | C2'—N1'—H1'N | 116.9 (19) |
C6—N5—C4 | 123.5 (2) | C6'—N5'—C4' | 123.2 (2) |
C6—N5—H5N | 119.1 (19) | C6'—N5'—H5'N | 115.1 (17) |
C4—N5—H5N | 117.1 (19) | C4'—N5'—H5'N | 117.0 (17) |
C31—N33—C36 | 124.5 (2) | C31'—N33'—C34' | 118.2 (2) |
C31—N33—C34 | 117.9 (2) | C31'—N33'—C36' | 124.9 (2) |
C36—N33—C34 | 117.5 (2) | C34'—N33'—C36' | 116.8 (2) |
C3—C2—N1 | 119.9 (2) | C3'—C2'—N1' | 119.0 (2) |
C3—C2—C21 | 126.3 (2) | C3'—C2'—C21' | 126.4 (2) |
N1—C2—C21 | 113.7 (2) | N1'—C2'—C21' | 114.6 (2) |
C2—C3—C31 | 122.6 (2) | C2'—C3'—C31' | 122.4 (2) |
C2—C3—C4 | 117.9 (2) | C2'—C3'—C4' | 119.0 (2) |
C31—C3—C4 | 118.7 (2) | C31'—C3'—C4' | 117.74 (19) |
N5—C4—C3 | 108.67 (19) | N5'—C4'—C3' | 108.54 (18) |
N5—C4—C7 | 111.8 (2) | N5'—C4'—C7' | 111.46 (19) |
C3—C4—C7 | 109.45 (18) | C3'—C4'—C7' | 110.91 (18) |
N5—C4—H4 | 109.0 | N5'—C4'—H4' | 108.6 |
C3—C4—H4 | 109.0 | C3'—C4'—H4' | 108.6 |
C7—C4—H4 | 109.0 | C7'—C4'—H4' | 108.6 |
N5—C6—N1 | 116.1 (2) | N5'—C6'—N1' | 116.2 (2) |
N5—C6—S1 | 123.73 (19) | N5'—C6'—S1' | 122.73 (18) |
N1—C6—S1 | 120.09 (19) | N1'—C6'—S1' | 121.08 (19) |
C8—C7—C12 | 116.9 (2) | C8'—C7'—C12' | 116.4 (2) |
C8—C7—C4 | 122.1 (2) | C8'—C7'—C4' | 121.5 (2) |
C12—C7—C4 | 121.0 (2) | C12'—C7'—C4' | 122.2 (2) |
C9—C8—C7 | 121.9 (2) | C7'—C8'—C9' | 122.5 (2) |
C9—C8—H8 | 119.0 | C7'—C8'—H8' | 118.8 |
C7—C8—H8 | 119.0 | C9'—C8'—H8' | 118.8 |
C10—C9—C8 | 119.4 (2) | C10'—C9'—C8' | 118.2 (2) |
C10—C9—H9 | 120.3 | C10'—C9'—H9' | 120.9 |
C8—C9—H9 | 120.3 | C8'—C9'—H9' | 120.9 |
C9—C10—C11 | 121.0 (2) | C11'—C10'—C9' | 121.6 (2) |
C9—C10—Cl2 | 120.2 (2) | C11'—C10'—Cl2' | 119.1 (2) |
C11—C10—Cl2 | 118.9 (2) | C9'—C10'—Cl2' | 119.3 (2) |
C10—C11—C12 | 118.7 (2) | C10'—C11'—C12' | 118.5 (2) |
C10—C11—H11 | 120.6 | C10'—C11'—H11' | 120.7 |
C12—C11—H11 | 120.6 | C12'—C11'—H11' | 120.7 |
C11—C12—C7 | 122.0 (2) | C11'—C12'—C7' | 122.7 (2) |
C11—C12—Cl1 | 117.3 (2) | C11'—C12'—Cl1' | 117.53 (19) |
C7—C12—Cl1 | 120.6 (2) | C7'—C12'—Cl1' | 119.8 (2) |
C2—C21—H21A | 109.5 | C2'—C21'—H21D | 109.5 |
C2—C21—H21B | 109.5 | C2'—C21'—H21E | 109.5 |
H21A—C21—H21B | 109.5 | H21D—C21'—H21E | 109.5 |
C2—C21—H21C | 109.5 | C2'—C21'—H21F | 109.5 |
H21A—C21—H21C | 109.5 | H21D—C21'—H21F | 109.5 |
H21B—C21—H21C | 109.5 | H21E—C21'—H21F | 109.5 |
O32—C31—N33 | 121.0 (2) | O32'—C31'—N33' | 121.0 (2) |
O32—C31—C3 | 118.8 (2) | O32'—C31'—C3' | 118.5 (2) |
N33—C31—C3 | 120.18 (19) | N33'—C31'—C3' | 120.5 (2) |
N33—C34—C35 | 112.3 (3) | N33'—C34'—C35' | 113.2 (3) |
N33—C34—H34A | 109.1 | N33'—C34'—H34C | 108.9 |
C35—C34—H34A | 109.1 | C35'—C34'—H34C | 108.9 |
N33—C34—H34B | 109.1 | N33'—C34'—H34D | 108.9 |
C35—C34—H34B | 109.1 | C35'—C34'—H34D | 108.9 |
H34A—C34—H34B | 107.9 | H34C—C34'—H34D | 107.8 |
C34—C35—H35A | 109.5 | C34'—C35'—H35D | 109.5 |
C34—C35—H35B | 109.5 | C34'—C35'—H35E | 109.5 |
H35A—C35—H35B | 109.5 | H35D—C35'—H35E | 109.5 |
C34—C35—H35C | 109.5 | C34'—C35'—H35F | 109.5 |
H35A—C35—H35C | 109.5 | H35D—C35'—H35F | 109.5 |
H35B—C35—H35C | 109.5 | H35E—C35'—H35F | 109.5 |
N33—C36—C37 | 114.2 (2) | N33'—C36'—C37' | 113.0 (2) |
N33—C36—H36A | 108.7 | N33'—C36'—H36C | 109.0 |
C37—C36—H36A | 108.7 | C37'—C36'—H36C | 109.0 |
N33—C36—H36B | 108.7 | N33'—C36'—H36D | 109.0 |
C37—C36—H36B | 108.7 | C37'—C36'—H36D | 109.0 |
H36A—C36—H36B | 107.6 | H36C—C36'—H36D | 107.8 |
C36—C37—H37A | 109.5 | C36'—C37'—H37D | 109.5 |
C36—C37—H37B | 109.5 | C36'—C37'—H37E | 109.5 |
H37A—C37—H37B | 109.5 | H37D—C37'—H37E | 109.5 |
C36—C37—H37C | 109.5 | C36'—C37'—H37F | 109.5 |
H37A—C37—H37C | 109.5 | H37D—C37'—H37F | 109.5 |
H37B—C37—H37C | 109.5 | H37E—C37'—H37F | 109.5 |
| | | |
C6—N1—C2—C3 | 21.5 (4) | C6'—N1'—C2'—C3' | 18.2 (3) |
C6—N1—C2—C21 | −154.9 (2) | C6'—N1'—C2'—C21' | −159.5 (2) |
N1—C2—C3—C31 | −167.5 (2) | N1'—C2'—C3'—C31' | −167.0 (2) |
C21—C2—C3—C31 | 8.4 (4) | C21'—C2'—C3'—C31' | 10.3 (4) |
N1—C2—C3—C4 | 2.7 (3) | N1'—C2'—C3'—C4' | 2.3 (3) |
C21—C2—C3—C4 | 178.6 (2) | C21'—C2'—C3'—C4' | 179.6 (2) |
C6—N5—C4—C3 | 36.7 (3) | C6'—N5'—C4'—C3' | 37.3 (3) |
C6—N5—C4—C7 | −84.2 (3) | C6'—N5'—C4'—C7' | −85.2 (3) |
C2—C3—C4—N5 | −28.2 (3) | C2'—C3'—C4'—N5' | −26.5 (3) |
C31—C3—C4—N5 | 142.5 (2) | C31'—C3'—C4'—N5' | 143.3 (2) |
C2—C3—C4—C7 | 94.1 (2) | C2'—C3'—C4'—C7' | 96.3 (2) |
C31—C3—C4—C7 | −95.2 (2) | C31'—C3'—C4'—C7' | −93.9 (2) |
C4—N5—C6—N1 | −16.5 (4) | C4'—N5'—C6'—N1' | −20.8 (3) |
C4—N5—C6—S1 | 165.70 (19) | C4'—N5'—C6'—S1' | 159.78 (18) |
C2—N1—C6—N5 | −14.9 (3) | C2'—N1'—C6'—N5' | −9.3 (3) |
C2—N1—C6—S1 | 163.05 (19) | C2'—N1'—C6'—S1' | 170.10 (18) |
N5—C4—C7—C8 | 24.7 (3) | N5'—C4'—C7'—C8' | 30.9 (3) |
C3—C4—C7—C8 | −95.7 (3) | C3'—C4'—C7'—C8' | −90.2 (3) |
N5—C4—C7—C12 | −158.6 (2) | N5'—C4'—C7'—C12' | −150.3 (2) |
C3—C4—C7—C12 | 81.0 (3) | C3'—C4'—C7'—C12' | 88.6 (3) |
C12—C7—C8—C9 | −2.7 (4) | C12'—C7'—C8'—C9' | −2.2 (4) |
C4—C7—C8—C9 | 174.2 (2) | C4'—C7'—C8'—C9' | 176.6 (2) |
C7—C8—C9—C10 | −0.2 (4) | C7'—C8'—C9'—C10' | −0.2 (4) |
C8—C9—C10—C11 | 2.3 (4) | C8'—C9'—C10'—C11' | 2.4 (4) |
C8—C9—C10—Cl2 | −179.0 (2) | C8'—C9'—C10'—Cl2' | −177.1 (2) |
C9—C10—C11—C12 | −1.5 (4) | C9'—C10'—C11'—C12' | −1.9 (4) |
Cl2—C10—C11—C12 | 179.9 (2) | Cl2'—C10'—C11'—C12' | 177.5 (2) |
C10—C11—C12—C7 | −1.5 (4) | C10'—C11'—C12'—C7' | −0.7 (4) |
C10—C11—C12—Cl1 | 176.6 (2) | C10'—C11'—C12'—Cl1' | 179.4 (2) |
C8—C7—C12—C11 | 3.6 (4) | C8'—C7'—C12'—C11' | 2.7 (4) |
C4—C7—C12—C11 | −173.3 (2) | C4'—C7'—C12'—C11' | −176.1 (2) |
C8—C7—C12—Cl1 | −174.53 (18) | C8'—C7'—C12'—Cl1' | −177.36 (19) |
C4—C7—C12—Cl1 | 8.6 (3) | C4'—C7'—C12'—Cl1' | 3.8 (3) |
C36—N33—C31—O32 | 175.0 (2) | C34'—N33'—C31'—O32' | −9.5 (4) |
C34—N33—C31—O32 | −8.4 (4) | C36'—N33'—C31'—O32' | 173.6 (3) |
C36—N33—C31—C3 | −6.1 (4) | C34'—N33'—C31'—C3' | 168.7 (2) |
C34—N33—C31—C3 | 170.5 (2) | C36'—N33'—C31'—C3' | −8.2 (4) |
C2—C3—C31—O32 | 110.3 (3) | C2'—C3'—C31'—O32' | 109.5 (3) |
C4—C3—C31—O32 | −59.9 (3) | C4'—C3'—C31'—O32' | −60.0 (3) |
C2—C3—C31—N33 | −68.6 (3) | C2'—C3'—C31'—N33' | −68.8 (3) |
C4—C3—C31—N33 | 121.2 (2) | C4'—C3'—C31'—N33' | 121.8 (2) |
C31—N33—C34—C35 | −86.1 (3) | C31'—N33'—C34'—C35' | −86.8 (4) |
C36—N33—C34—C35 | 90.7 (3) | C36'—N33'—C34'—C35' | 90.3 (4) |
C31—N33—C36—C37 | −124.4 (3) | C31'—N33'—C36'—C37' | −118.9 (3) |
C34—N33—C36—C37 | 59.0 (4) | C34'—N33'—C36'—C37' | 64.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5′—H5′N···S1 | 0.87 (3) | 2.45 (3) | 3.239 (2) | 151 (2) |
N1′—H1′N···O32′i | 0.78 (3) | 2.05 (3) | 2.813 (3) | 169 (3) |
N5—H5N···S1′ii | 0.81 (3) | 2.65 (3) | 3.430 (2) | 162 (2) |
N1—H1N···O32i | 0.93 (3) | 1.87 (3) | 2.791 (3) | 169 (2) |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x+1/2, −y+1/2, z. |
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