The asymmetric unit of the title compound, C
21H
20N
2S, comprises two independent molecules, which differ in the conformations of the cyclohexene and dihydropyrimidine rings, and in the orientations of the benzylidene moieties. The crystal structure is stabilized by weak N—H
S hydrogen bonds.
Supporting information
CCDC reference: 263657
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.048
- wR factor = 0.129
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6'
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8'
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3 ... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
(8E)-8-benzylidene-3,4,5,6,7,8-hexahydro-4-phenylquinazoline-2(1
H)-thione
top
Crystal data top
C21H20N2S | Z = 4 |
Mr = 332.45 | F(000) = 704 |
Triclinic, P1 | Dx = 1.243 Mg m−3 |
Hall symbol: -P 1 | Melting point = 469–470 K |
a = 10.472 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.526 (4) Å | Cell parameters from 771 reflections |
c = 14.963 (5) Å | θ = 3.2–25.1° |
α = 113.440 (5)° | µ = 0.19 mm−1 |
β = 100.681 (6)° | T = 293 K |
γ = 104.926 (6)° | Plate, colourless |
V = 1777.2 (10) Å3 | 0.32 × 0.30 × 0.24 mm |
Data collection top
Bruker SMART1000 CCD area-detector diffractometer | 7205 independent reflections |
Radiation source: fine-focus sealed tube | 3846 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −11→13 |
Tmin = 0.928, Tmax = 0.956 | k = −16→15 |
10378 measured reflections | l = −14→18 |
Refinement top
Refinement on F2 | 65 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0508P)2 + 0.1289P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.129 | (Δ/σ)max = 0.001 |
S = 1.00 | Δρmax = 0.21 e Å−3 |
7205 reflections | Δρmin = −0.16 e Å−3 |
477 parameters | |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | −0.04098 (7) | 0.32197 (6) | 0.43267 (6) | 0.0535 (2) | |
N1 | 0.1856 (2) | 0.48362 (19) | 0.45416 (18) | 0.0482 (6) | |
H1 | 0.152 (3) | 0.528 (2) | 0.4929 (19) | 0.054 (9)* | |
N2 | 0.1283 (2) | 0.3042 (2) | 0.32088 (18) | 0.0485 (6) | |
H2 | 0.074 (3) | 0.234 (2) | 0.286 (2) | 0.055 (9)* | |
C1 | 0.0983 (3) | 0.3720 (2) | 0.3989 (2) | 0.0430 (6) | |
C2 | 0.2255 (3) | 0.3461 (2) | 0.2734 (2) | 0.0471 (7) | |
H2A | 0.2752 | 0.2928 | 0.2534 | 0.057* | |
C3 | 0.3325 (3) | 0.4641 (2) | 0.3508 (2) | 0.0468 (7) | |
C4 | 0.3084 (2) | 0.5284 (2) | 0.4356 (2) | 0.0441 (6) | |
C5 | 0.4112 (3) | 0.6440 (2) | 0.5147 (2) | 0.0491 (7) | |
C6 | 0.5394 (8) | 0.6854 (7) | 0.4855 (5) | 0.063 (3) | 0.594 (12) |
H6A | 0.5680 | 0.7686 | 0.5114 | 0.075* | 0.594 (12) |
H6B | 0.6151 | 0.6711 | 0.5201 | 0.075* | 0.594 (12) |
C7 | 0.5192 (9) | 0.6295 (5) | 0.3714 (6) | 0.067 (2) | 0.594 (12) |
H7A | 0.4560 | 0.6548 | 0.3376 | 0.080* | 0.594 (12) |
H7B | 0.6083 | 0.6545 | 0.3610 | 0.080* | 0.594 (12) |
C8 | 0.4607 (12) | 0.4990 (8) | 0.3235 (11) | 0.074 (5) | 0.594 (12) |
H8A | 0.4379 | 0.4651 | 0.2493 | 0.088* | 0.594 (12) |
H8B | 0.5292 | 0.4720 | 0.3493 | 0.088* | 0.594 (12) |
C6' | 0.4971 (13) | 0.7039 (8) | 0.4684 (10) | 0.077 (5) | 0.406 (12) |
H6'A | 0.5662 | 0.7781 | 0.5215 | 0.092* | 0.406 (12) |
H6'B | 0.4383 | 0.7164 | 0.4190 | 0.092* | 0.406 (12) |
C7' | 0.5674 (9) | 0.6231 (8) | 0.4159 (11) | 0.073 (3) | 0.406 (12) |
H7'A | 0.6177 | 0.6053 | 0.4651 | 0.087* | 0.406 (12) |
H7'B | 0.6345 | 0.6615 | 0.3922 | 0.087* | 0.406 (12) |
C8' | 0.4613 (13) | 0.5112 (12) | 0.3249 (11) | 0.042 (5) | 0.406 (12) |
H8'A | 0.5043 | 0.4538 | 0.3048 | 0.050* | 0.406 (12) |
H8'B | 0.4332 | 0.5252 | 0.2669 | 0.050* | 0.406 (12) |
C9 | 0.1480 (3) | 0.3453 (2) | 0.1762 (2) | 0.0474 (7) | |
C10 | 0.1313 (3) | 0.2605 (3) | 0.0802 (2) | 0.0689 (9) | |
H10 | 0.1674 | 0.2030 | 0.0745 | 0.083* | |
C11 | 0.0613 (4) | 0.2605 (3) | −0.0078 (3) | 0.0881 (11) | |
H11 | 0.0505 | 0.2031 | −0.0723 | 0.106* | |
C12 | 0.0081 (3) | 0.3441 (4) | −0.0001 (3) | 0.0846 (11) | |
H12 | −0.0368 | 0.3449 | −0.0594 | 0.101* | |
C13 | 0.0204 (3) | 0.4269 (3) | 0.0943 (3) | 0.0795 (10) | |
H13 | −0.0189 | 0.4824 | 0.0993 | 0.095* | |
C14 | 0.0911 (3) | 0.4279 (3) | 0.1821 (2) | 0.0656 (8) | |
H14 | 0.1005 | 0.4851 | 0.2462 | 0.079* | |
C15 | 0.4014 (3) | 0.6943 (2) | 0.6081 (2) | 0.0486 (7) | |
H15 | 0.3229 | 0.6526 | 0.6165 | 0.058* | |
C16 | 0.4910 (3) | 0.8038 (2) | 0.7010 (2) | 0.0474 (7) | |
C17 | 0.4303 (3) | 0.8478 (3) | 0.7760 (2) | 0.0595 (8) | |
H17 | 0.3367 | 0.8087 | 0.7640 | 0.071* | |
C18 | 0.5053 (4) | 0.9475 (3) | 0.8672 (2) | 0.0791 (10) | |
H18 | 0.4617 | 0.9764 | 0.9150 | 0.095* | |
C19 | 0.6456 (4) | 1.0046 (3) | 0.8876 (3) | 0.0824 (11) | |
H19 | 0.6978 | 1.0706 | 0.9500 | 0.099* | |
C20 | 0.7062 (3) | 0.9629 (3) | 0.8153 (3) | 0.0758 (10) | |
H20 | 0.8002 | 1.0018 | 0.8283 | 0.091* | |
C21 | 0.6310 (3) | 0.8643 (2) | 0.7232 (2) | 0.0623 (8) | |
H21 | 0.6751 | 0.8377 | 0.6750 | 0.075* | |
S2 | 0.91078 (8) | 1.03371 (6) | 0.14923 (6) | 0.0650 (3) | |
N3 | 0.6895 (2) | 0.8746 (2) | 0.1350 (2) | 0.0578 (7) | |
H3 | 0.697 (3) | 0.839 (2) | 0.078 (2) | 0.060 (10)* | |
N4 | 0.7905 (2) | 1.0357 (2) | 0.29031 (18) | 0.0481 (6) | |
H4 | 0.845 (3) | 1.101 (2) | 0.3257 (19) | 0.050 (8)* | |
C22 | 0.7919 (3) | 0.9798 (2) | 0.1956 (2) | 0.0463 (6) | |
C23 | 0.6871 (3) | 1.0001 (2) | 0.33676 (19) | 0.0447 (6) | |
H23 | 0.6441 | 1.0585 | 0.3566 | 0.054* | |
C24 | 0.5733 (2) | 0.8864 (2) | 0.2579 (2) | 0.0445 (6) | |
C25 | 0.5779 (3) | 0.8286 (2) | 0.1634 (2) | 0.0452 (6) | |
C26 | 0.4669 (3) | 0.7179 (2) | 0.0838 (2) | 0.0474 (7) | |
C27 | 0.3706 (3) | 0.6606 (2) | 0.1268 (2) | 0.0606 (8) | |
H27A | 0.4170 | 0.6250 | 0.1601 | 0.073* | |
H27B | 0.2876 | 0.6002 | 0.0711 | 0.073* | |
C28 | 0.3292 (3) | 0.7483 (2) | 0.2035 (2) | 0.0637 (8) | |
H28A | 0.2680 | 0.7096 | 0.2306 | 0.076* | |
H28B | 0.2770 | 0.7795 | 0.1683 | 0.076* | |
C29 | 0.4533 (3) | 0.8476 (2) | 0.2924 (2) | 0.0591 (8) | |
H29A | 0.4251 | 0.9123 | 0.3255 | 0.071* | |
H29B | 0.4832 | 0.8231 | 0.3429 | 0.071* | |
C30 | 0.7567 (2) | 0.9974 (2) | 0.43388 (19) | 0.0413 (6) | |
C31 | 0.7989 (3) | 0.9073 (2) | 0.4284 (2) | 0.0515 (7) | |
H31 | 0.7848 | 0.8477 | 0.3642 | 0.062* | |
C32 | 0.8610 (3) | 0.9036 (3) | 0.5154 (3) | 0.0632 (8) | |
H32 | 0.8895 | 0.8423 | 0.5099 | 0.076* | |
C33 | 0.8810 (3) | 0.9897 (4) | 0.6098 (3) | 0.0743 (10) | |
H33 | 0.9222 | 0.9868 | 0.6689 | 0.089* | |
C34 | 0.8407 (3) | 1.0798 (3) | 0.6179 (2) | 0.0775 (10) | |
H34 | 0.8550 | 1.1386 | 0.6826 | 0.093* | |
C35 | 0.7778 (3) | 1.0849 (3) | 0.5294 (2) | 0.0627 (8) | |
H35 | 0.7506 | 1.1468 | 0.5352 | 0.075* | |
C36 | 0.4517 (3) | 0.6779 (2) | −0.0162 (2) | 0.0562 (7) | |
H36 | 0.5160 | 0.7238 | −0.0325 | 0.067* | |
C37 | 0.3467 (3) | 0.5706 (2) | −0.1042 (2) | 0.0513 (7) | |
C38 | 0.3088 (3) | 0.4638 (2) | −0.1051 (2) | 0.0638 (8) | |
H38 | 0.3511 | 0.4576 | −0.0482 | 0.077* | |
C39 | 0.2090 (3) | 0.3671 (3) | −0.1898 (3) | 0.0721 (9) | |
H39 | 0.1843 | 0.2963 | −0.1891 | 0.086* | |
C40 | 0.1456 (3) | 0.3733 (3) | −0.2746 (2) | 0.0714 (9) | |
H40 | 0.0779 | 0.3075 | −0.3312 | 0.086* | |
C41 | 0.1829 (3) | 0.4776 (3) | −0.2756 (2) | 0.0732 (9) | |
H41 | 0.1403 | 0.4829 | −0.3329 | 0.088* | |
C42 | 0.2831 (3) | 0.5743 (3) | −0.1917 (2) | 0.0655 (8) | |
H42 | 0.3089 | 0.6442 | −0.1939 | 0.079* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0499 (4) | 0.0379 (4) | 0.0611 (5) | 0.0049 (3) | 0.0258 (4) | 0.0160 (4) |
N1 | 0.0426 (13) | 0.0335 (13) | 0.0604 (16) | 0.0087 (11) | 0.0220 (12) | 0.0153 (12) |
N2 | 0.0568 (15) | 0.0319 (13) | 0.0528 (15) | 0.0098 (12) | 0.0265 (12) | 0.0164 (12) |
C1 | 0.0422 (15) | 0.0351 (15) | 0.0501 (17) | 0.0118 (12) | 0.0145 (13) | 0.0203 (13) |
C2 | 0.0545 (16) | 0.0457 (16) | 0.0559 (17) | 0.0246 (14) | 0.0294 (14) | 0.0287 (14) |
C3 | 0.0431 (15) | 0.0511 (17) | 0.0558 (18) | 0.0160 (13) | 0.0185 (13) | 0.0339 (15) |
C4 | 0.0397 (15) | 0.0426 (16) | 0.0542 (17) | 0.0113 (13) | 0.0148 (13) | 0.0294 (14) |
C5 | 0.0422 (15) | 0.0497 (17) | 0.0557 (18) | 0.0073 (13) | 0.0116 (13) | 0.0328 (15) |
C6 | 0.054 (4) | 0.063 (4) | 0.056 (4) | −0.006 (3) | 0.011 (3) | 0.034 (3) |
C7 | 0.059 (4) | 0.072 (4) | 0.083 (5) | 0.016 (3) | 0.037 (4) | 0.047 (4) |
C8 | 0.074 (8) | 0.079 (7) | 0.083 (8) | 0.027 (5) | 0.028 (6) | 0.052 (6) |
C6' | 0.088 (8) | 0.067 (6) | 0.065 (7) | −0.003 (5) | 0.018 (5) | 0.043 (5) |
C7' | 0.051 (5) | 0.077 (6) | 0.093 (8) | 0.009 (4) | 0.026 (5) | 0.050 (6) |
C8' | 0.030 (7) | 0.050 (7) | 0.058 (8) | 0.011 (5) | 0.032 (6) | 0.031 (6) |
C9 | 0.0488 (16) | 0.0424 (16) | 0.0524 (17) | 0.0144 (13) | 0.0242 (13) | 0.0216 (14) |
C10 | 0.087 (2) | 0.056 (2) | 0.063 (2) | 0.0269 (18) | 0.0310 (18) | 0.0244 (18) |
C11 | 0.108 (3) | 0.081 (3) | 0.053 (2) | 0.018 (2) | 0.020 (2) | 0.023 (2) |
C12 | 0.070 (2) | 0.097 (3) | 0.071 (3) | 0.009 (2) | 0.0014 (19) | 0.047 (2) |
C13 | 0.075 (2) | 0.087 (3) | 0.083 (3) | 0.035 (2) | 0.015 (2) | 0.047 (2) |
C14 | 0.076 (2) | 0.065 (2) | 0.061 (2) | 0.0336 (18) | 0.0241 (17) | 0.0283 (17) |
C15 | 0.0393 (15) | 0.0420 (16) | 0.0641 (19) | 0.0087 (13) | 0.0139 (14) | 0.0295 (15) |
C16 | 0.0464 (16) | 0.0409 (16) | 0.0554 (18) | 0.0140 (13) | 0.0074 (14) | 0.0284 (14) |
C17 | 0.0581 (18) | 0.063 (2) | 0.0534 (19) | 0.0163 (16) | 0.0091 (15) | 0.0318 (17) |
C18 | 0.090 (3) | 0.084 (3) | 0.054 (2) | 0.034 (2) | 0.0116 (19) | 0.029 (2) |
C19 | 0.086 (3) | 0.068 (2) | 0.059 (2) | 0.015 (2) | −0.007 (2) | 0.0188 (19) |
C20 | 0.056 (2) | 0.061 (2) | 0.084 (3) | 0.0056 (17) | 0.0035 (19) | 0.028 (2) |
C21 | 0.0510 (18) | 0.0530 (18) | 0.070 (2) | 0.0134 (15) | 0.0105 (15) | 0.0244 (17) |
S2 | 0.0634 (5) | 0.0544 (5) | 0.0539 (5) | −0.0036 (4) | 0.0242 (4) | 0.0169 (4) |
N3 | 0.0540 (15) | 0.0439 (15) | 0.0474 (16) | −0.0030 (12) | 0.0188 (13) | 0.0071 (13) |
N4 | 0.0507 (14) | 0.0344 (13) | 0.0436 (15) | −0.0009 (12) | 0.0116 (12) | 0.0157 (12) |
C22 | 0.0458 (16) | 0.0402 (15) | 0.0451 (16) | 0.0074 (13) | 0.0128 (13) | 0.0187 (14) |
C23 | 0.0443 (15) | 0.0389 (15) | 0.0481 (16) | 0.0118 (12) | 0.0163 (13) | 0.0196 (13) |
C24 | 0.0404 (15) | 0.0447 (16) | 0.0462 (16) | 0.0114 (12) | 0.0098 (12) | 0.0238 (14) |
C25 | 0.0429 (15) | 0.0392 (15) | 0.0479 (17) | 0.0070 (12) | 0.0110 (13) | 0.0219 (14) |
C26 | 0.0424 (15) | 0.0414 (15) | 0.0509 (17) | 0.0065 (13) | 0.0080 (13) | 0.0231 (14) |
C27 | 0.0549 (18) | 0.0504 (17) | 0.0571 (19) | −0.0026 (14) | 0.0090 (15) | 0.0245 (15) |
C28 | 0.0491 (17) | 0.066 (2) | 0.0587 (19) | −0.0012 (15) | 0.0150 (15) | 0.0275 (17) |
C29 | 0.0497 (17) | 0.0634 (19) | 0.0544 (18) | 0.0069 (15) | 0.0144 (14) | 0.0282 (16) |
C30 | 0.0380 (14) | 0.0390 (15) | 0.0404 (15) | 0.0062 (12) | 0.0130 (12) | 0.0174 (13) |
C31 | 0.0460 (16) | 0.0492 (17) | 0.0511 (18) | 0.0110 (14) | 0.0107 (13) | 0.0222 (14) |
C32 | 0.0476 (17) | 0.071 (2) | 0.074 (2) | 0.0144 (16) | 0.0133 (16) | 0.044 (2) |
C33 | 0.0490 (19) | 0.115 (3) | 0.061 (2) | 0.016 (2) | 0.0133 (16) | 0.053 (2) |
C34 | 0.065 (2) | 0.103 (3) | 0.0382 (19) | 0.017 (2) | 0.0160 (16) | 0.0176 (19) |
C35 | 0.0644 (19) | 0.063 (2) | 0.0517 (19) | 0.0252 (16) | 0.0223 (16) | 0.0161 (16) |
C36 | 0.0518 (17) | 0.0448 (16) | 0.0525 (18) | −0.0020 (14) | 0.0096 (14) | 0.0202 (15) |
C37 | 0.0470 (16) | 0.0499 (17) | 0.0481 (17) | 0.0112 (14) | 0.0155 (13) | 0.0186 (14) |
C38 | 0.069 (2) | 0.0504 (19) | 0.061 (2) | 0.0178 (16) | 0.0106 (16) | 0.0231 (16) |
C39 | 0.080 (2) | 0.0429 (18) | 0.074 (2) | 0.0133 (17) | 0.0226 (19) | 0.0157 (17) |
C40 | 0.063 (2) | 0.059 (2) | 0.054 (2) | 0.0041 (17) | 0.0135 (16) | 0.0040 (17) |
C41 | 0.078 (2) | 0.080 (2) | 0.0395 (18) | 0.015 (2) | 0.0110 (16) | 0.0191 (18) |
C42 | 0.076 (2) | 0.0575 (19) | 0.0484 (18) | 0.0062 (17) | 0.0174 (16) | 0.0241 (16) |
Geometric parameters (Å, º) top
S1—C1 | 1.696 (3) | C19—C20 | 1.357 (4) |
N1—C1 | 1.347 (3) | C19—H19 | 0.93 |
N1—C4 | 1.401 (3) | C20—C21 | 1.376 (4) |
N1—H1 | 0.85 (2) | C20—H20 | 0.93 |
N2—C1 | 1.318 (3) | C21—H21 | 0.93 |
N2—C2 | 1.467 (3) | S2—C22 | 1.679 (3) |
N2—H2 | 0.85 (3) | N3—C22 | 1.350 (3) |
C2—C3 | 1.507 (3) | N3—C25 | 1.398 (3) |
C2—C9 | 1.522 (4) | N3—H3 | 0.82 (3) |
C2—H2A | 0.98 | N4—C22 | 1.319 (3) |
C3—C4 | 1.335 (3) | N4—C23 | 1.471 (3) |
C3—C8 | 1.492 (7) | N4—H4 | 0.81 (2) |
C3—C8' | 1.524 (7) | C23—C24 | 1.506 (3) |
C4—C5 | 1.481 (3) | C23—C30 | 1.519 (3) |
C5—C15 | 1.327 (3) | C23—H23 | 0.98 |
C5—C6' | 1.499 (8) | C24—C25 | 1.334 (3) |
C5—C6 | 1.526 (6) | C24—C29 | 1.496 (3) |
C6—C7 | 1.513 (7) | C25—C26 | 1.477 (3) |
C6—H6A | 0.97 | C26—C36 | 1.334 (3) |
C6—H6B | 0.97 | C26—C27 | 1.505 (3) |
C7—C8 | 1.510 (9) | C27—C28 | 1.510 (4) |
C7—H7A | 0.97 | C27—H27A | 0.97 |
C7—H7B | 0.97 | C27—H27B | 0.97 |
C8—H8A | 0.97 | C28—C29 | 1.517 (3) |
C8—H8B | 0.97 | C28—H28A | 0.97 |
C6'—C7' | 1.515 (10) | C28—H28B | 0.97 |
C6'—H6'A | 0.97 | C29—H29A | 0.97 |
C6'—H6'B | 0.97 | C29—H29B | 0.97 |
C7'—C8' | 1.521 (10) | C30—C35 | 1.376 (3) |
C7'—H7'A | 0.97 | C30—C31 | 1.377 (3) |
C7'—H7'B | 0.97 | C31—C32 | 1.369 (4) |
C8'—H8'A | 0.97 | C31—H31 | 0.93 |
C8'—H8'B | 0.97 | C32—C33 | 1.361 (4) |
C9—C14 | 1.376 (4) | C32—H32 | 0.93 |
C9—C10 | 1.380 (4) | C33—C34 | 1.359 (4) |
C10—C11 | 1.382 (4) | C33—H33 | 0.93 |
C10—H10 | 0.93 | C34—C35 | 1.400 (4) |
C11—C12 | 1.359 (5) | C34—H34 | 0.93 |
C11—H11 | 0.93 | C35—H35 | 0.93 |
C12—C13 | 1.366 (5) | C36—C37 | 1.473 (3) |
C12—H12 | 0.93 | C36—H36 | 0.93 |
C13—C14 | 1.376 (4) | C37—C42 | 1.381 (4) |
C13—H13 | 0.93 | C37—C38 | 1.390 (4) |
C14—H14 | 0.93 | C38—C39 | 1.377 (4) |
C15—C16 | 1.473 (3) | C38—H38 | 0.93 |
C15—H15 | 0.93 | C39—C40 | 1.364 (4) |
C16—C21 | 1.384 (4) | C39—H39 | 0.93 |
C16—C17 | 1.395 (4) | C40—C41 | 1.370 (4) |
C17—C18 | 1.375 (4) | C40—H40 | 0.93 |
C17—H17 | 0.93 | C41—C42 | 1.373 (4) |
C18—C19 | 1.382 (5) | C41—H41 | 0.93 |
C18—H18 | 0.93 | C42—H42 | 0.93 |
| | | |
C1—N1—C4 | 123.3 (2) | C17—C18—H18 | 120.1 |
C1—N1—H1 | 114.0 (18) | C19—C18—H18 | 120.1 |
C4—N1—H1 | 121.6 (18) | C20—C19—C18 | 119.1 (3) |
C1—N2—C2 | 124.3 (2) | C20—C19—H19 | 120.4 |
C1—N2—H2 | 117.8 (18) | C18—C19—H19 | 120.4 |
C2—N2—H2 | 115.9 (18) | C19—C20—C21 | 121.2 (3) |
N2—C1—N1 | 117.4 (2) | C19—C20—H20 | 119.4 |
N2—C1—S1 | 122.23 (19) | C21—C20—H20 | 119.4 |
N1—C1—S1 | 120.4 (2) | C20—C21—C16 | 121.1 (3) |
N2—C2—C3 | 110.0 (2) | C20—C21—H21 | 119.4 |
N2—C2—C9 | 111.4 (2) | C16—C21—H21 | 119.4 |
C3—C2—C9 | 112.3 (2) | C22—N3—C25 | 124.0 (2) |
N2—C2—H2A | 107.6 | C22—N3—H3 | 114 (2) |
C3—C2—H2A | 107.6 | C25—N3—H3 | 122 (2) |
C9—C2—H2A | 107.6 | C22—N4—C23 | 128.0 (2) |
C4—C3—C8 | 125.2 (5) | C22—N4—H4 | 117.8 (19) |
C4—C3—C2 | 120.2 (2) | C23—N4—H4 | 113.6 (18) |
C8—C3—C2 | 114.6 (4) | N4—C22—N3 | 116.3 (2) |
C4—C3—C8' | 121.4 (5) | N4—C22—S2 | 123.5 (2) |
C2—C3—C8' | 118.1 (5) | N3—C22—S2 | 120.2 (2) |
C3—C4—N1 | 119.6 (2) | N4—C23—C24 | 109.8 (2) |
C3—C4—C5 | 122.2 (2) | N4—C23—C30 | 111.1 (2) |
N1—C4—C5 | 118.1 (2) | C24—C23—C30 | 113.1 (2) |
C15—C5—C4 | 121.1 (2) | N4—C23—H23 | 107.5 |
C15—C5—C6' | 125.5 (5) | C24—C23—H23 | 107.5 |
C4—C5—C6' | 111.7 (5) | C30—C23—H23 | 107.5 |
C15—C5—C6 | 124.1 (3) | C25—C24—C29 | 123.3 (2) |
C4—C5—C6 | 113.7 (3) | C25—C24—C23 | 121.8 (2) |
C7—C6—C5 | 115.3 (5) | C29—C24—C23 | 114.8 (2) |
C7—C6—H6A | 108.4 | C24—C25—N3 | 119.8 (2) |
C5—C6—H6A | 108.4 | C24—C25—C26 | 123.1 (2) |
C7—C6—H6B | 108.4 | N3—C25—C26 | 117.0 (2) |
C5—C6—H6B | 108.4 | C36—C26—C25 | 122.2 (2) |
H6A—C6—H6B | 107.5 | C36—C26—C27 | 124.5 (2) |
C8—C7—C6 | 111.5 (9) | C25—C26—C27 | 113.3 (2) |
C8—C7—H7A | 109.3 | C26—C27—C28 | 110.4 (2) |
C6—C7—H7A | 109.3 | C26—C27—H27A | 109.6 |
C8—C7—H7B | 109.3 | C28—C27—H27A | 109.6 |
C6—C7—H7B | 109.3 | C26—C27—H27B | 109.6 |
H7A—C7—H7B | 108.0 | C28—C27—H27B | 109.6 |
C3—C8—C7 | 108.1 (6) | H27A—C27—H27B | 108.1 |
C3—C8—H8A | 110.1 | C27—C28—C29 | 113.1 (2) |
C7—C8—H8A | 110.1 | C27—C28—H28A | 109.0 |
C3—C8—H8B | 110.1 | C29—C28—H28A | 109.0 |
C7—C8—H8B | 110.1 | C27—C28—H28B | 109.0 |
H8A—C8—H8B | 108.4 | C29—C28—H28B | 109.0 |
C5—C6'—C7' | 105.3 (8) | H28A—C28—H28B | 107.8 |
C5—C6'—H6'A | 110.7 | C24—C29—C28 | 112.1 (2) |
C7'—C6'—H6'A | 110.7 | C24—C29—H29A | 109.2 |
C5—C6'—H6'B | 110.7 | C28—C29—H29A | 109.2 |
C7'—C6'—H6'B | 110.7 | C24—C29—H29B | 109.2 |
H6'A—C6'—H6'B | 108.8 | C28—C29—H29B | 109.2 |
C6'—C7'—C8' | 111.4 (11) | H29A—C29—H29B | 107.9 |
C6'—C7'—H7'A | 109.4 | C35—C30—C31 | 118.6 (3) |
C8'—C7'—H7'A | 109.4 | C35—C30—C23 | 120.4 (2) |
C6'—C7'—H7'B | 109.4 | C31—C30—C23 | 120.9 (2) |
C8'—C7'—H7'B | 109.4 | C32—C31—C30 | 121.5 (3) |
H7'A—C7'—H7'B | 108.0 | C32—C31—H31 | 119.3 |
C7'—C8'—C3 | 111.6 (7) | C30—C31—H31 | 119.3 |
C7'—C8'—H8'A | 109.3 | C33—C32—C31 | 119.9 (3) |
C3—C8'—H8'A | 109.3 | C33—C32—H32 | 120.1 |
C7'—C8'—H8'B | 109.3 | C31—C32—H32 | 120.1 |
C3—C8'—H8'B | 109.3 | C34—C33—C32 | 120.1 (3) |
H8'A—C8'—H8'B | 108.0 | C34—C33—H33 | 120.0 |
C14—C9—C10 | 118.5 (3) | C32—C33—H33 | 120.0 |
C14—C9—C2 | 120.9 (2) | C33—C34—C35 | 120.5 (3) |
C10—C9—C2 | 120.7 (3) | C33—C34—H34 | 119.7 |
C9—C10—C11 | 120.4 (3) | C35—C34—H34 | 119.7 |
C9—C10—H10 | 119.8 | C30—C35—C34 | 119.4 (3) |
C11—C10—H10 | 119.8 | C30—C35—H35 | 120.3 |
C12—C11—C10 | 120.1 (3) | C34—C35—H35 | 120.3 |
C12—C11—H11 | 120.0 | C26—C36—C37 | 128.7 (3) |
C10—C11—H11 | 120.0 | C26—C36—H36 | 115.7 |
C11—C12—C13 | 120.4 (3) | C37—C36—H36 | 115.7 |
C11—C12—H12 | 119.8 | C42—C37—C38 | 117.4 (3) |
C13—C12—H12 | 119.8 | C42—C37—C36 | 119.2 (3) |
C12—C13—C14 | 119.7 (3) | C38—C37—C36 | 123.4 (3) |
C12—C13—H13 | 120.1 | C39—C38—C37 | 120.4 (3) |
C14—C13—H13 | 120.1 | C39—C38—H38 | 119.8 |
C13—C14—C9 | 121.0 (3) | C37—C38—H38 | 119.8 |
C13—C14—H14 | 119.5 | C40—C39—C38 | 121.1 (3) |
C9—C14—H14 | 119.5 | C40—C39—H39 | 119.4 |
C5—C15—C16 | 132.2 (3) | C38—C39—H39 | 119.4 |
C5—C15—H15 | 113.9 | C39—C40—C41 | 119.3 (3) |
C16—C15—H15 | 113.9 | C39—C40—H40 | 120.4 |
C21—C16—C17 | 116.9 (3) | C41—C40—H40 | 120.4 |
C21—C16—C15 | 126.4 (3) | C40—C41—C42 | 120.0 (3) |
C17—C16—C15 | 116.7 (2) | C40—C41—H41 | 120.0 |
C18—C17—C16 | 121.7 (3) | C42—C41—H41 | 120.0 |
C18—C17—H17 | 119.2 | C41—C42—C37 | 121.8 (3) |
C16—C17—H17 | 119.2 | C41—C42—H42 | 119.1 |
C17—C18—C19 | 119.9 (3) | C37—C42—H42 | 119.1 |
| | | |
C2—N2—C1—N1 | −16.9 (4) | C21—C16—C17—C18 | 0.9 (4) |
C2—N2—C1—S1 | 165.2 (2) | C15—C16—C17—C18 | 178.0 (2) |
C4—N1—C1—N2 | −3.3 (4) | C16—C17—C18—C19 | −2.1 (5) |
C4—N1—C1—S1 | 174.75 (19) | C17—C18—C19—C20 | 2.1 (5) |
C1—N2—C2—C3 | 26.9 (3) | C18—C19—C20—C21 | −1.0 (5) |
C1—N2—C2—C9 | −98.4 (3) | C19—C20—C21—C16 | −0.1 (5) |
N2—C2—C3—C4 | −18.7 (3) | C17—C16—C21—C20 | 0.2 (4) |
C9—C2—C3—C4 | 106.0 (3) | C15—C16—C21—C20 | −176.6 (3) |
N2—C2—C3—C8 | 161.5 (8) | C23—N4—C22—N3 | −3.2 (4) |
C9—C2—C3—C8 | −73.8 (8) | C23—N4—C22—S2 | 176.0 (2) |
N2—C2—C3—C8' | 166.6 (10) | C25—N3—C22—N4 | 6.5 (4) |
C9—C2—C3—C8' | −68.7 (10) | C25—N3—C22—S2 | −172.8 (2) |
C8—C3—C4—N1 | −177.6 (9) | C22—N4—C23—C24 | −1.5 (4) |
C2—C3—C4—N1 | 2.6 (4) | C22—N4—C23—C30 | 124.3 (3) |
C8'—C3—C4—N1 | 177.1 (10) | N4—C23—C24—C25 | 3.7 (3) |
C8—C3—C4—C5 | −1.2 (9) | C30—C23—C24—C25 | −121.0 (3) |
C2—C3—C4—C5 | 179.0 (2) | N4—C23—C24—C29 | −173.4 (2) |
C8'—C3—C4—C5 | −6.4 (11) | C30—C23—C24—C29 | 61.9 (3) |
C1—N1—C4—C3 | 10.1 (4) | C29—C24—C25—N3 | 175.8 (2) |
C1—N1—C4—C5 | −166.5 (2) | C23—C24—C25—N3 | −1.1 (4) |
C3—C4—C5—C15 | −163.9 (3) | C29—C24—C25—C26 | −2.1 (4) |
N1—C4—C5—C15 | 12.6 (4) | C23—C24—C25—C26 | −179.0 (2) |
C3—C4—C5—C6' | 30.5 (6) | C22—N3—C25—C24 | −4.5 (4) |
N1—C4—C5—C6' | −153.0 (6) | C22—N3—C25—C26 | 173.6 (2) |
C3—C4—C5—C6 | 4.8 (5) | C24—C25—C26—C36 | 160.7 (3) |
N1—C4—C5—C6 | −178.7 (5) | N3—C25—C26—C36 | −17.2 (4) |
C15—C5—C6—C7 | −169.4 (7) | C24—C25—C26—C27 | −16.0 (4) |
C4—C5—C6—C7 | 22.3 (11) | N3—C25—C26—C27 | 166.0 (2) |
C6'—C5—C6—C7 | −67.8 (13) | C36—C26—C27—C28 | −131.9 (3) |
C5—C6—C7—C8 | −52.5 (14) | C25—C26—C27—C28 | 44.8 (3) |
C4—C3—C8—C7 | −28.2 (15) | C26—C27—C28—C29 | −58.1 (3) |
C2—C3—C8—C7 | 151.6 (8) | C25—C24—C29—C28 | −9.9 (4) |
C8'—C3—C8—C7 | 22 (11) | C23—C24—C29—C28 | 167.2 (2) |
C6—C7—C8—C3 | 52.7 (15) | C27—C28—C29—C24 | 39.9 (3) |
C15—C5—C6'—C7' | 136.9 (8) | N4—C23—C30—C35 | 103.4 (3) |
C4—C5—C6'—C7' | −58.2 (12) | C24—C23—C30—C35 | −132.6 (2) |
C6—C5—C6'—C7' | 41.7 (11) | N4—C23—C30—C31 | −77.2 (3) |
C5—C6'—C7'—C8' | 66.6 (17) | C24—C23—C30—C31 | 46.8 (3) |
C6'—C7'—C8'—C3 | −44 (2) | C35—C30—C31—C32 | −0.2 (4) |
C4—C3—C8'—C7' | 12.8 (19) | C23—C30—C31—C32 | −179.6 (2) |
C8—C3—C8'—C7' | −119 (13) | C30—C31—C32—C33 | 0.6 (4) |
C2—C3—C8'—C7' | −172.6 (10) | C31—C32—C33—C34 | −0.7 (5) |
N2—C2—C9—C14 | 75.0 (3) | C32—C33—C34—C35 | 0.3 (5) |
C3—C2—C9—C14 | −49.0 (3) | C31—C30—C35—C34 | −0.2 (4) |
N2—C2—C9—C10 | −104.0 (3) | C23—C30—C35—C34 | 179.2 (2) |
C3—C2—C9—C10 | 132.1 (3) | C33—C34—C35—C30 | 0.1 (5) |
C14—C9—C10—C11 | 1.2 (4) | C25—C26—C36—C37 | −179.5 (3) |
C2—C9—C10—C11 | −179.8 (3) | C27—C26—C36—C37 | −3.1 (5) |
C9—C10—C11—C12 | −0.1 (5) | C26—C36—C37—C42 | 136.4 (3) |
C10—C11—C12—C13 | −1.6 (5) | C26—C36—C37—C38 | −44.6 (4) |
C11—C12—C13—C14 | 2.2 (5) | C42—C37—C38—C39 | −1.5 (4) |
C12—C13—C14—C9 | −1.0 (5) | C36—C37—C38—C39 | 179.5 (3) |
C10—C9—C14—C13 | −0.7 (4) | C37—C38—C39—C40 | 0.3 (5) |
C2—C9—C14—C13 | −179.7 (3) | C38—C39—C40—C41 | 0.4 (5) |
C4—C5—C15—C16 | 176.6 (2) | C39—C40—C41—C42 | 0.1 (5) |
C6'—C5—C15—C16 | −19.9 (8) | C40—C41—C42—C37 | −1.4 (5) |
C6—C5—C15—C16 | 9.1 (7) | C38—C37—C42—C41 | 2.0 (4) |
C5—C15—C16—C21 | −22.0 (5) | C36—C37—C42—C41 | −178.9 (3) |
C5—C15—C16—C17 | 161.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.85 (3) | 2.57 (3) | 3.396 (3) | 163 (2) |
N2—H2···S2ii | 0.85 (3) | 2.52 (3) | 3.352 (3) | 167 (2) |
N4—H4···S1iii | 0.80 (3) | 2.56 (3) | 3.342 (3) | 165 (3) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y−1, z; (iii) x+1, y+1, z. |