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The asymmetric unit of the title compound {systematic name: 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-hydroxy-1-[2-(2-methyl-4-oxo-3,4,6,7,8,9-hexahydro-2H-pyrido[1,2-a]pyrimidin-3-yl)ethyl]piperidine}, C23H27FN4O2, contains two independent risperidone molecules. The piperidine and the tetrahydropyridine rings adopt chair and sofa conformations, respectively.
Supporting information
CCDC reference: 618227
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.064
- wR factor = 0.151
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 37 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C3 .. 8.77 su
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 .. 6.11 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C40 - C41 .. 6.72 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C42
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N12
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.01
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C18 - C19 ... 1.38 Ang.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C19 - C20 ... 1.42 Ang.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C41 - C42 ... 1.43 Ang.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C42 - C43 ... 1.43 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
11 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
12 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
4-(6-fluoro-1,2-
benzisoxazol-3-yl)-1-hydroxy-1-[2-(2-methyl-4-oxo-3,4,6,7,8,9-hexahydro-2
H- pyrido[1,2-
a]pyrimidin-3-yl)ethyl]piperidine
top
Crystal data top
C23H27FN4O2 | Z = 4 |
Mr = 410.49 | F(000) = 872.00 |
Triclinic, P1 | Dx = 1.300 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 9.938 (4) Å | Cell parameters from 11861 reflections |
b = 11.016 (6) Å | θ = 3.0–27.5° |
c = 20.274 (9) Å | µ = 0.09 mm−1 |
α = 75.240 (17)° | T = 298 K |
β = 79.514 (13)° | Needle, colorless |
γ = 81.397 (17)° | 0.29 × 0.16 × 0.12 mm |
V = 2097.8 (17) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | Rint = 0.051 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5° |
ω scans | h = −12→11 |
20587 measured reflections | k = −14→14 |
9462 independent reflections | l = −26→26 |
3536 reflections with F2 > 2σ(F2) | |
Refinement top
Refinement on F2 | w = 1/[0.0003Fo2 + 1σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.064 | (Δ/σ)max < 0.001 |
wR(F2) = 0.151 | Δρmax = 0.60 e Å−3 |
S = 1.05 | Δρmin = −0.68 e Å−3 |
9462 reflections | Extinction correction: Larson (1970) |
596 parameters | Extinction coefficient: 155 (21) |
All H-atom parameters refined | |
Special details top
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F11 | −0.43529 (16) | 0.6723 (2) | 0.31536 (9) | 0.0944 (6) | |
F21 | 0.19762 (16) | 0.29901 (19) | 0.15606 (10) | 0.0956 (6) | |
O11 | 0.03428 (19) | 0.7445 (2) | 0.28246 (11) | 0.0780 (7) | |
O12 | 0.8642 (2) | 0.2433 (2) | 0.50955 (12) | 0.0985 (8) | |
O21 | 0.63702 (19) | 0.2636 (2) | 0.22463 (10) | 0.0691 (6) | |
O22 | 1.4669 (2) | 0.7711 (2) | −0.00742 (10) | 0.0829 (7) | |
N11 | 0.1514 (2) | 0.6612 (2) | 0.30565 (13) | 0.0810 (9) | |
N12 | 0.4383 (2) | 0.3322 (2) | 0.44176 (11) | 0.0628 (7) | |
N13 | 0.8983 (2) | 0.0682 (2) | 0.59419 (11) | 0.0615 (7) | |
N14 | 0.7159 (2) | −0.0373 (2) | 0.66190 (12) | 0.0697 (8) | |
N21 | 0.7415 (2) | 0.3495 (2) | 0.20516 (12) | 0.0678 (8) | |
N22 | 1.0271 (2) | 0.6695 (2) | 0.05724 (11) | 0.0602 (7) | |
N23 | 1.5015 (2) | 0.9463 (2) | −0.09250 (11) | 0.0564 (7) | |
N24 | 1.3358 (2) | 1.0453 (2) | −0.16215 (12) | 0.0725 (8) | |
C1 | −0.0785 (2) | 0.6807 (2) | 0.30832 (13) | 0.0593 (9) | |
C2 | −0.2100 (2) | 0.7236 (2) | 0.29494 (13) | 0.0633 (9) | |
C3 | −0.3023 (2) | 0.6385 (2) | 0.32612 (13) | 0.0679 (10) | |
C4 | −0.2729 (3) | 0.5213 (3) | 0.36887 (14) | 0.0788 (11) | |
C5 | −0.1387 (2) | 0.4821 (2) | 0.37953 (13) | 0.0678 (9) | |
C6 | −0.0410 (2) | 0.5630 (2) | 0.34881 (12) | 0.0558 (8) | |
C7 | 0.1060 (2) | 0.5581 (3) | 0.34299 (13) | 0.0606 (9) | |
C8 | 0.2026 (2) | 0.4476 (2) | 0.37271 (13) | 0.0625 (9) | |
C9 | 0.3473 (2) | 0.4484 (3) | 0.33703 (14) | 0.0820 (11) | |
C10 | 0.4381 (2) | 0.3350 (3) | 0.36954 (14) | 0.0804 (11) | |
C11 | 0.3006 (2) | 0.3224 (3) | 0.47846 (14) | 0.0831 (11) | |
C12 | 0.2011 (2) | 0.4343 (3) | 0.44947 (13) | 0.0780 (10) | |
C13 | 0.5353 (2) | 0.2298 (3) | 0.47353 (14) | 0.0725 (10) | |
C14 | 0.5714 (2) | 0.2546 (3) | 0.53857 (16) | 0.0769 (11) | |
C15 | 0.6675 (2) | 0.1509 (2) | 0.57559 (13) | 0.0607 (9) | |
C16 | 0.8125 (2) | 0.1618 (3) | 0.55620 (14) | 0.0660 (9) | |
C17 | 1.0484 (2) | 0.0799 (3) | 0.57326 (17) | 0.0872 (12) | |
C18 | 1.1349 (3) | −0.0112 (4) | 0.6192 (2) | 0.111 (2) | |
C19 | 1.0864 (3) | −0.1243 (5) | 0.6548 (2) | 0.1172 (18) | |
C20 | 0.9447 (2) | −0.1236 (3) | 0.68401 (18) | 0.0904 (12) | |
C21 | 0.8480 (2) | −0.0262 (2) | 0.64460 (14) | 0.0636 (9) | |
C22 | 0.6262 (2) | 0.0524 (2) | 0.62672 (14) | 0.0616 (9) | |
C23 | 0.4794 (2) | 0.0305 (3) | 0.64950 (18) | 0.0879 (12) | |
C24 | 0.5314 (2) | 0.3199 (2) | 0.18976 (13) | 0.0574 (8) | |
C25 | 0.4101 (2) | 0.2692 (2) | 0.19489 (13) | 0.0639 (9) | |
C26 | 0.3195 (2) | 0.3432 (3) | 0.15407 (16) | 0.0686 (10) | |
C27 | 0.3435 (2) | 0.4596 (3) | 0.11143 (16) | 0.0751 (10) | |
C28 | 0.4633 (2) | 0.5079 (2) | 0.10857 (14) | 0.0698 (10) | |
C29 | 0.5598 (2) | 0.4355 (2) | 0.14898 (13) | 0.0568 (8) | |
C30 | 0.6959 (2) | 0.4485 (2) | 0.16125 (13) | 0.0577 (8) | |
C31 | 0.7784 (2) | 0.5574 (2) | 0.13248 (13) | 0.0590 (8) | |
C32 | 0.9109 (2) | 0.5410 (3) | 0.16283 (13) | 0.0687 (10) | |
C33 | 0.9924 (2) | 0.6534 (3) | 0.13153 (13) | 0.0696 (10) | |
C34 | 0.9026 (2) | 0.6922 (3) | 0.02545 (14) | 0.0676 (9) | |
C35 | 0.8139 (2) | 0.5836 (3) | 0.05403 (13) | 0.0693 (10) | |
C36 | 1.1166 (2) | 0.7701 (3) | 0.02606 (14) | 0.0667 (10) | |
C37 | 1.2048 (2) | 0.7494 (2) | −0.04044 (13) | 0.0638 (9) | |
C38 | 1.2905 (2) | 0.8555 (2) | −0.07606 (12) | 0.0551 (8) | |
C39 | 1.4231 (2) | 0.8508 (2) | −0.05536 (13) | 0.0576 (8) | |
C40 | 1.6400 (2) | 0.9392 (3) | −0.07317 (16) | 0.0787 (11) | |
C41 | 1.7334 (3) | 1.0210 (4) | −0.1259 (2) | 0.0933 (15) | |
C42 | 1.6693 (3) | 1.1427 (5) | −0.1558 (2) | 0.1096 (19) | |
C43 | 1.5467 (3) | 1.1398 (3) | −0.18280 (19) | 0.0948 (13) | |
C44 | 1.4552 (2) | 1.0397 (3) | −0.14375 (14) | 0.0657 (9) | |
C45 | 1.2545 (2) | 0.9510 (2) | −0.12871 (14) | 0.0625 (9) | |
C46 | 1.1188 (2) | 0.9636 (3) | −0.15511 (18) | 0.0908 (12) | |
H2 | −0.2339 | 0.8026 | 0.2674 | 0.076* | |
H4 | −0.3423 | 0.4699 | 0.3900 | 0.095* | |
H5 | −0.1149 | 0.4028 | 0.4069 | 0.081* | |
H8 | 0.1689 | 0.3715 | 0.3680 | 0.075* | |
H25 | 0.3914 | 0.1913 | 0.2237 | 0.077* | |
H27 | 0.2779 | 0.5051 | 0.0846 | 0.090* | |
H28 | 0.4805 | 0.5867 | 0.0805 | 0.084* | |
H31 | 0.7223 | 0.6323 | 0.1440 | 0.071* | |
H91 | 0.3825 | 0.5243 | 0.3395 | 0.098* | |
H92 | 0.3489 | 0.4480 | 0.2891 | 0.098* | |
H101 | 0.5313 | 0.3390 | 0.3450 | 0.096* | |
H102 | 0.4040 | 0.2588 | 0.3666 | 0.096* | |
H111 | 0.3012 | 0.3195 | 0.5266 | 0.100* | |
H112 | 0.2696 | 0.2454 | 0.4747 | 0.100* | |
H121 | 0.2278 | 0.5109 | 0.4563 | 0.094* | |
H122 | 0.1088 | 0.4217 | 0.4737 | 0.094* | |
H131 | 0.4939 | 0.1512 | 0.4855 | 0.087* | |
H132 | 0.6188 | 0.2230 | 0.4408 | 0.087* | |
H141 | 0.4868 | 0.2647 | 0.5701 | 0.092* | |
H142 | 0.6148 | 0.3323 | 0.5257 | 0.092* | |
H171 | 1.0646 | 0.1645 | 0.5733 | 0.105* | |
H172 | 1.0751 | 0.0663 | 0.5270 | 0.105* | |
H181 | 1.1513 | 0.0308 | 0.6532 | 0.133* | |
H182 | 1.2215 | −0.0310 | 0.5911 | 0.133* | |
H191 | 1.1395 | −0.1593 | 0.6923 | 0.141* | |
H192 | 1.1037 | −0.1796 | 0.6231 | 0.141* | |
H201 | 0.9354 | −0.1090 | 0.7299 | 0.108* | |
H202 | 0.9172 | −0.2061 | 0.6873 | 0.108* | |
H231 | 0.4515 | 0.0417 | 0.6957 | 0.105* | |
H232 | 0.4680 | −0.0539 | 0.6485 | 0.105* | |
H233 | 0.4237 | 0.0897 | 0.6191 | 0.105* | |
H321 | 0.8883 | 0.5326 | 0.2123 | 0.082* | |
H322 | 0.9665 | 0.4652 | 0.1536 | 0.082* | |
H331 | 0.9377 | 0.7290 | 0.1415 | 0.084* | |
H332 | 1.0765 | 0.6396 | 0.1516 | 0.084* | |
H341 | 0.8499 | 0.7693 | 0.0345 | 0.081* | |
H342 | 0.9284 | 0.7015 | −0.0239 | 0.081* | |
H351 | 0.7292 | 0.6051 | 0.0342 | 0.083* | |
H352 | 0.8636 | 0.5082 | 0.0413 | 0.083* | |
H361 | 1.0598 | 0.8502 | 0.0162 | 0.080* | |
H362 | 1.1764 | 0.7722 | 0.0585 | 0.080* | |
H371 | 1.1449 | 0.7412 | −0.0715 | 0.077* | |
H372 | 1.2659 | 0.6720 | −0.0298 | 0.077* | |
H401 | 1.6294 | 0.9652 | −0.0301 | 0.094* | |
H402 | 1.6818 | 0.8524 | −0.0669 | 0.094* | |
H411 | 1.8083 | 1.0328 | −0.1042 | 0.112* | |
H412 | 1.7700 | 0.9779 | −0.1626 | 0.112* | |
H421 | 1.6459 | 1.1909 | −0.1206 | 0.132* | |
H422 | 1.7348 | 1.1845 | −0.1931 | 0.132* | |
H431 | 1.4926 | 1.2212 | −0.1844 | 0.114* | |
H432 | 1.5742 | 1.1276 | −0.2293 | 0.114* | |
H461 | 1.0487 | 0.9349 | −0.1173 | 0.109* | |
H462 | 1.1278 | 0.9135 | −0.1884 | 0.109* | |
H463 | 1.0938 | 1.0506 | −0.1764 | 0.109* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F11 | 0.0584 (10) | 0.1142 (17) | 0.0946 (13) | −0.0071 (10) | −0.0220 (9) | 0.0104 (12) |
F21 | 0.0590 (10) | 0.1004 (16) | 0.1189 (15) | −0.0285 (10) | −0.0127 (10) | 0.0007 (12) |
O11 | 0.0622 (12) | 0.0695 (15) | 0.0863 (14) | −0.0168 (11) | −0.0128 (11) | 0.0171 (12) |
O12 | 0.0874 (15) | 0.098 (2) | 0.0859 (15) | −0.0231 (13) | −0.0100 (12) | 0.0283 (15) |
O21 | 0.0604 (11) | 0.0683 (15) | 0.0654 (12) | −0.0161 (10) | −0.0077 (10) | 0.0123 (11) |
O22 | 0.0847 (14) | 0.0804 (16) | 0.0697 (13) | −0.0100 (12) | −0.0262 (11) | 0.0183 (12) |
N11 | 0.0574 (14) | 0.080 (2) | 0.0890 (19) | −0.0117 (14) | −0.0176 (14) | 0.0178 (16) |
N12 | 0.0478 (12) | 0.0776 (19) | 0.0521 (13) | 0.0019 (11) | −0.0099 (11) | 0.0013 (13) |
N13 | 0.0431 (11) | 0.0735 (18) | 0.0584 (14) | −0.0150 (11) | −0.0072 (11) | 0.0061 (13) |
N14 | 0.0485 (13) | 0.0722 (19) | 0.0733 (16) | −0.0114 (12) | −0.0110 (12) | 0.0142 (14) |
N21 | 0.0631 (14) | 0.0729 (19) | 0.0586 (14) | −0.0193 (13) | −0.0063 (12) | 0.0053 (14) |
N22 | 0.0555 (13) | 0.0718 (18) | 0.0517 (14) | −0.0263 (12) | 0.0007 (11) | −0.0066 (12) |
N23 | 0.0417 (11) | 0.0668 (17) | 0.0543 (13) | −0.0132 (11) | −0.0070 (10) | 0.0012 (12) |
N24 | 0.0520 (13) | 0.0765 (19) | 0.0762 (16) | −0.0227 (13) | −0.0156 (12) | 0.0181 (15) |
C1 | 0.0620 (17) | 0.059 (2) | 0.0512 (16) | −0.0089 (15) | −0.0084 (14) | −0.0011 (15) |
C2 | 0.0546 (16) | 0.064 (2) | 0.0594 (18) | −0.0060 (15) | −0.0076 (14) | 0.0067 (16) |
C3 | 0.0528 (17) | 0.088 (2) | 0.0575 (17) | −0.0000 (17) | −0.0191 (15) | −0.0038 (18) |
C4 | 0.0680 (19) | 0.090 (2) | 0.0665 (19) | −0.0224 (18) | −0.0142 (16) | 0.0142 (19) |
C5 | 0.0634 (18) | 0.064 (2) | 0.0626 (18) | −0.0117 (16) | −0.0118 (15) | 0.0126 (16) |
C6 | 0.0541 (16) | 0.061 (2) | 0.0464 (15) | −0.0040 (14) | −0.0119 (13) | 0.0001 (14) |
C7 | 0.0607 (17) | 0.063 (2) | 0.0564 (17) | −0.0103 (15) | −0.0154 (14) | −0.0036 (16) |
C8 | 0.0533 (16) | 0.062 (2) | 0.0687 (19) | −0.0063 (14) | −0.0194 (15) | −0.0011 (16) |
C9 | 0.0678 (19) | 0.113 (3) | 0.0566 (18) | 0.0053 (19) | −0.0145 (16) | −0.0098 (19) |
C10 | 0.0699 (19) | 0.100 (2) | 0.066 (2) | 0.0120 (19) | −0.0200 (17) | −0.0137 (19) |
C11 | 0.0546 (17) | 0.108 (3) | 0.065 (2) | 0.0010 (18) | −0.0075 (15) | 0.0125 (19) |
C12 | 0.0597 (18) | 0.100 (2) | 0.0580 (18) | 0.0080 (17) | −0.0062 (15) | 0.0004 (18) |
C13 | 0.0607 (17) | 0.076 (2) | 0.072 (2) | 0.0049 (16) | −0.0179 (16) | −0.0035 (18) |
C14 | 0.074 (2) | 0.075 (2) | 0.077 (2) | 0.0033 (17) | −0.0317 (18) | −0.0009 (18) |
C15 | 0.0560 (16) | 0.064 (2) | 0.0579 (17) | −0.0017 (15) | −0.0161 (14) | −0.0043 (16) |
C16 | 0.0614 (17) | 0.073 (2) | 0.0529 (17) | −0.0169 (16) | −0.0079 (15) | 0.0091 (17) |
C17 | 0.0504 (17) | 0.111 (3) | 0.094 (2) | −0.0248 (18) | −0.0103 (17) | −0.003 (2) |
C18 | 0.060 (2) | 0.125 (4) | 0.131 (5) | −0.019 (2) | −0.047 (3) | 0.027 (4) |
C19 | 0.070 (2) | 0.119 (5) | 0.125 (3) | 0.015 (2) | −0.026 (2) | 0.033 (3) |
C20 | 0.0631 (19) | 0.097 (3) | 0.092 (2) | 0.0021 (18) | −0.0236 (19) | 0.014 (2) |
C21 | 0.0514 (16) | 0.071 (2) | 0.0599 (17) | −0.0090 (15) | −0.0130 (14) | 0.0043 (16) |
C22 | 0.0459 (14) | 0.063 (2) | 0.0699 (19) | −0.0078 (14) | −0.0097 (14) | −0.0034 (17) |
C23 | 0.0520 (17) | 0.096 (2) | 0.107 (2) | −0.0113 (17) | −0.0110 (17) | −0.007 (2) |
C24 | 0.0517 (16) | 0.058 (2) | 0.0518 (16) | −0.0119 (14) | 0.0048 (13) | 0.0008 (15) |
C25 | 0.0655 (17) | 0.058 (2) | 0.0585 (18) | −0.0143 (16) | 0.0031 (15) | −0.0004 (16) |
C26 | 0.0566 (17) | 0.074 (2) | 0.0691 (19) | −0.0141 (17) | 0.0001 (16) | −0.0080 (18) |
C27 | 0.0593 (18) | 0.076 (2) | 0.076 (2) | −0.0095 (17) | −0.0112 (16) | 0.0085 (19) |
C28 | 0.0643 (18) | 0.063 (2) | 0.0671 (19) | −0.0095 (16) | −0.0045 (16) | 0.0091 (17) |
C29 | 0.0521 (15) | 0.0545 (19) | 0.0547 (16) | −0.0103 (14) | 0.0009 (13) | −0.0001 (15) |
C30 | 0.0566 (16) | 0.060 (2) | 0.0485 (16) | −0.0102 (15) | 0.0046 (13) | −0.0056 (15) |
C31 | 0.0530 (15) | 0.057 (2) | 0.0592 (17) | −0.0141 (14) | 0.0016 (13) | −0.0019 (15) |
C32 | 0.0728 (18) | 0.081 (2) | 0.0491 (16) | −0.0217 (17) | −0.0053 (15) | −0.0048 (16) |
C33 | 0.0649 (18) | 0.092 (2) | 0.0510 (17) | −0.0320 (18) | 0.0038 (14) | −0.0099 (17) |
C34 | 0.0642 (17) | 0.072 (2) | 0.0601 (18) | −0.0260 (16) | −0.0048 (15) | 0.0026 (17) |
C35 | 0.0683 (18) | 0.079 (2) | 0.0573 (17) | −0.0296 (17) | −0.0114 (15) | 0.0031 (16) |
C36 | 0.0671 (18) | 0.068 (2) | 0.0649 (19) | −0.0260 (16) | 0.0017 (15) | −0.0135 (17) |
C37 | 0.0596 (16) | 0.065 (2) | 0.0603 (17) | −0.0217 (15) | 0.0022 (14) | −0.0014 (16) |
C38 | 0.0508 (15) | 0.057 (2) | 0.0523 (16) | −0.0136 (14) | −0.0012 (13) | −0.0044 (15) |
C39 | 0.0547 (16) | 0.061 (2) | 0.0506 (16) | −0.0074 (14) | −0.0023 (14) | −0.0040 (15) |
C40 | 0.0492 (16) | 0.103 (2) | 0.086 (2) | −0.0014 (17) | −0.0248 (16) | −0.019 (2) |
C41 | 0.0457 (18) | 0.107 (3) | 0.120 (3) | −0.023 (2) | −0.006 (2) | −0.010 (2) |
C42 | 0.078 (2) | 0.126 (5) | 0.110 (3) | −0.065 (2) | −0.024 (2) | 0.039 (3) |
C43 | 0.085 (2) | 0.099 (3) | 0.093 (2) | −0.045 (2) | −0.028 (2) | 0.022 (2) |
C44 | 0.0514 (16) | 0.078 (2) | 0.0607 (18) | −0.0198 (15) | −0.0098 (14) | 0.0038 (17) |
C45 | 0.0476 (15) | 0.068 (2) | 0.0690 (19) | −0.0117 (15) | −0.0123 (14) | −0.0055 (17) |
C46 | 0.0572 (17) | 0.096 (2) | 0.113 (2) | −0.0205 (18) | −0.0262 (19) | 0.004 (2) |
Geometric parameters (Å, º) top
F11—C3 | 1.359 (3) | C38—C39 | 1.444 (3) |
F21—C26 | 1.361 (3) | C38—C45 | 1.352 (3) |
O11—N11 | 1.441 (3) | C40—C41 | 1.488 (4) |
O11—C1 | 1.364 (3) | C41—C42 | 1.429 (6) |
O12—C16 | 1.222 (3) | C42—C43 | 1.431 (5) |
O21—N21 | 1.443 (3) | C43—C44 | 1.504 (4) |
O21—C24 | 1.355 (3) | C45—C46 | 1.515 (4) |
O22—C39 | 1.229 (3) | C2—H2 | 0.930 |
N11—C7 | 1.287 (3) | C4—H4 | 0.930 |
N12—C10 | 1.457 (3) | C5—H5 | 0.930 |
N12—C11 | 1.439 (3) | C8—H8 | 0.980 |
N12—C13 | 1.466 (3) | C9—H91 | 0.970 |
N13—C16 | 1.398 (3) | C9—H92 | 0.970 |
N13—C17 | 1.490 (3) | C10—H101 | 0.970 |
N13—C21 | 1.343 (3) | C10—H102 | 0.970 |
N14—C21 | 1.311 (3) | C11—H111 | 0.970 |
N14—C22 | 1.375 (3) | C11—H112 | 0.970 |
N21—C30 | 1.300 (3) | C12—H121 | 0.970 |
N22—C33 | 1.453 (3) | C12—H122 | 0.970 |
N22—C34 | 1.457 (3) | C13—H131 | 0.970 |
N22—C36 | 1.467 (3) | C13—H132 | 0.970 |
N23—C39 | 1.381 (3) | C14—H141 | 0.970 |
N23—C40 | 1.485 (3) | C14—H142 | 0.970 |
N23—C44 | 1.355 (3) | C17—H171 | 0.970 |
N24—C44 | 1.295 (3) | C17—H172 | 0.970 |
N24—C45 | 1.373 (3) | C18—H181 | 0.970 |
C1—C2 | 1.373 (3) | C18—H182 | 0.970 |
C1—C6 | 1.384 (3) | C19—H191 | 0.970 |
C2—C3 | 1.365 (3) | C19—H192 | 0.970 |
C3—C4 | 1.383 (4) | C20—H201 | 0.970 |
C4—C5 | 1.377 (4) | C20—H202 | 0.970 |
C5—C6 | 1.372 (4) | C23—H231 | 0.960 |
C6—C7 | 1.438 (3) | C23—H232 | 0.960 |
C7—C8 | 1.501 (3) | C23—H233 | 0.960 |
C8—C9 | 1.488 (3) | C25—H25 | 0.930 |
C8—C12 | 1.523 (4) | C27—H27 | 0.930 |
C9—C10 | 1.506 (4) | C28—H28 | 0.930 |
C11—C12 | 1.523 (4) | C31—H31 | 0.980 |
C13—C14 | 1.526 (5) | C32—H321 | 0.970 |
C14—C15 | 1.510 (3) | C32—H322 | 0.970 |
C15—C16 | 1.437 (3) | C33—H331 | 0.970 |
C15—C22 | 1.351 (3) | C33—H332 | 0.970 |
C17—C18 | 1.473 (5) | C34—H341 | 0.970 |
C18—C19 | 1.378 (6) | C34—H342 | 0.970 |
C19—C20 | 1.425 (4) | C35—H351 | 0.970 |
C20—C21 | 1.499 (4) | C35—H352 | 0.970 |
C22—C23 | 1.484 (3) | C36—H361 | 0.970 |
C24—C25 | 1.380 (4) | C36—H362 | 0.970 |
C24—C29 | 1.369 (3) | C37—H371 | 0.970 |
C25—C26 | 1.367 (4) | C37—H372 | 0.970 |
C26—C27 | 1.378 (4) | C40—H401 | 0.970 |
C27—C28 | 1.361 (4) | C40—H402 | 0.970 |
C28—C29 | 1.396 (3) | C41—H411 | 0.970 |
C29—C30 | 1.453 (4) | C41—H412 | 0.970 |
C30—C31 | 1.488 (4) | C42—H421 | 0.970 |
C31—C32 | 1.520 (4) | C42—H422 | 0.970 |
C31—C35 | 1.526 (3) | C43—H431 | 0.970 |
C32—C33 | 1.518 (4) | C43—H432 | 0.970 |
C34—C35 | 1.524 (4) | C46—H461 | 0.960 |
C36—C37 | 1.518 (3) | C46—H462 | 0.960 |
C37—C38 | 1.502 (4) | C46—H463 | 0.960 |
| | | |
F11···C9i | 3.412 (4) | H92···C28 | 3.550 |
F11···C14ii | 3.268 (3) | H92···C29 | 3.229 |
F11···C23ii | 3.473 (4) | H92···H25 | 3.359 |
F11···C43iii | 3.209 (3) | H101···O21 | 2.754 |
F21···C20iv | 3.493 (3) | H101···N21 | 3.188 |
F21···C40v | 3.508 (4) | H101···C4vi | 3.171 |
O11···C33i | 3.563 (4) | H101···C24 | 3.207 |
O12···C5vi | 3.215 (3) | H101···H4vi | 2.473 |
O21···C10 | 3.428 (3) | H101···H232iv | 3.108 |
O21···C38v | 3.501 (3) | H102···O21 | 3.343 |
O21···C45v | 3.369 (4) | H102···N14iv | 3.089 |
O21···C46v | 3.589 (3) | H102···C22iv | 3.452 |
O22···C28vi | 3.235 (3) | H102···C23iv | 3.300 |
N11···C42vii | 3.593 (4) | H102···C24 | 3.504 |
N14···C25iv | 3.518 (3) | H102···C25 | 3.443 |
N23···C25v | 3.456 (4) | H102···H25 | 3.196 |
N24···C2iii | 3.474 (3) | H102···H232iv | 2.480 |
C2···N24iii | 3.474 (3) | H111···C2ii | 3.492 |
C5···O12i | 3.215 (3) | H111···C3ii | 3.138 |
C9···F11vi | 3.412 (4) | H111···C4ii | 3.029 |
C10···O21 | 3.428 (3) | H111···C5ii | 3.309 |
C14···F11ii | 3.268 (3) | H111···H4ii | 3.307 |
C20···F21iv | 3.493 (3) | H111···H171i | 2.984 |
C23···F11ii | 3.473 (4) | H112···C17i | 3.146 |
C24···C38v | 3.455 (4) | H112···H171i | 2.664 |
C25···N14iv | 3.518 (3) | H112···H172i | 2.842 |
C25···N23v | 3.456 (4) | H112···H182i | 3.381 |
C25···C39v | 3.470 (4) | H121···O12ix | 2.938 |
C28···O22i | 3.235 (3) | H121···C4ii | 3.576 |
C30···C37v | 3.595 (4) | H121···C5ii | 3.303 |
C33···O11vi | 3.563 (4) | H121···C14ix | 3.524 |
C37···C30v | 3.595 (4) | H121···C16ix | 3.517 |
C38···O21v | 3.501 (3) | H121···H4ii | 3.571 |
C38···C24v | 3.455 (4) | H121···H5ii | 3.123 |
C39···C25v | 3.470 (4) | H121···H122ii | 3.438 |
C40···F21v | 3.508 (4) | H121···H142ix | 2.627 |
C42···N11vii | 3.593 (4) | H122···O12i | 3.218 |
C43···F11iii | 3.209 (3) | H122···C5ii | 3.478 |
C45···O21v | 3.369 (4) | H122···C6ii | 3.582 |
C46···O21v | 3.589 (3) | H122···C12ii | 3.532 |
F11···H91i | 2.516 | H122···H5ii | 3.476 |
F11···H141ii | 2.534 | H122···H121ii | 3.438 |
F11···H142ii | 3.379 | H122···H122ii | 2.788 |
F11···H231ii | 3.083 | H122···H171i | 3.071 |
F11···H233ii | 3.252 | H131···H131iv | 3.219 |
F11···H431iii | 2.742 | H131···H182x | 3.239 |
F11···H432iii | 2.795 | H131···H232iv | 3.108 |
F21···H201iv | 2.954 | H132···C4vi | 3.482 |
F21···H202iv | 3.132 | H132···C18x | 3.401 |
F21···H322i | 2.714 | H132···C19x | 3.402 |
F21···H342viii | 3.158 | H132···H4vi | 2.711 |
F21···H402v | 2.763 | H132···H5vi | 3.407 |
F21···H412v | 2.991 | H132···H182x | 2.594 |
O11···H171ix | 3.267 | H132···H191x | 3.412 |
O11···H181ix | 3.261 | H132···H192x | 2.852 |
O11···H331i | 3.227 | H132···H232iv | 3.202 |
O11···H332i | 3.093 | H141···F11ii | 2.534 |
O11···H422vii | 2.731 | H141···C2ii | 3.521 |
O11···H463iii | 3.001 | H141···C3ii | 2.842 |
O12···H5vi | 2.356 | H141···C4ii | 3.262 |
O12···H121ix | 2.938 | H141···H4ii | 3.285 |
O12···H122vi | 3.218 | H142···F11ii | 3.379 |
O12···H192x | 2.900 | H142···C4vi | 3.424 |
O21···H92 | 3.504 | H142···C12ix | 3.552 |
O21···H101 | 2.754 | H142···H4vi | 2.774 |
O21···H102 | 3.343 | H142···H5vi | 3.307 |
O21···H191x | 2.950 | H142···H91ix | 3.493 |
O21···H231iv | 3.506 | H142···H121ix | 2.627 |
O21···H232iv | 3.124 | H171···O11ix | 3.267 |
O21···H371v | 3.456 | H171···C1ix | 3.311 |
O21···H462v | 2.924 | H171···C11vi | 3.178 |
O22···H28vi | 2.341 | H171···H111vi | 2.984 |
O22···H351vi | 3.073 | H171···H112vi | 2.664 |
O22···H401xi | 3.156 | H171···H122vi | 3.071 |
O22···H421xi | 2.743 | H172···N13x | 3.131 |
N11···H332i | 3.412 | H172···C16x | 3.323 |
N11···H422vii | 2.652 | H172···C17x | 3.376 |
N12···H4vi | 2.739 | H172···C21x | 3.549 |
N13···H172x | 3.131 | H172···H112vi | 2.842 |
N14···H25iv | 2.652 | H172···H172x | 2.762 |
N14···H102iv | 3.089 | H181···O11ix | 3.261 |
N14···H432xii | 3.209 | H181···C1ix | 3.407 |
N21···H101 | 3.188 | H181···C2ix | 3.304 |
N21···H191x | 2.836 | H181···C23vi | 3.247 |
N21···H371v | 3.090 | H181···H2ix | 3.011 |
N21···H462v | 3.068 | H181···H231vi | 3.279 |
N22···H27vi | 2.905 | H181···H232vi | 3.137 |
N22···H352v | 3.093 | H181···H233vi | 2.800 |
N23···H25v | 3.324 | H181···H462xiv | 3.121 |
N23···H401xi | 2.915 | H181···H463xiv | 3.456 |
N24···H2iii | 2.616 | H182···C13x | 3.328 |
N24···H231xiii | 2.911 | H182···C23vi | 3.235 |
N24···H331vii | 3.441 | H182···H112vi | 3.381 |
C1···H171ix | 3.311 | H182···H131x | 3.239 |
C1···H181ix | 3.407 | H182···H132x | 2.594 |
C1···H321i | 2.928 | H182···H232vi | 2.849 |
C1···H331i | 3.265 | H182···H233vi | 2.780 |
C1···H332i | 3.379 | H191···O21x | 2.950 |
C1···H463iii | 3.453 | H191···N21x | 2.836 |
C2···H111ii | 3.492 | H191···H132x | 3.412 |
C2···H141ii | 3.521 | H191···H232vi | 3.513 |
C2···H181ix | 3.304 | H191···H462xiv | 2.714 |
C2···H231ii | 3.272 | H192···O12x | 2.900 |
C2···H233ii | 3.309 | H192···C5iv | 3.312 |
C2···H321i | 2.962 | H192···C16x | 3.540 |
C2···H331i | 3.179 | H192···H5iv | 2.661 |
C2···H463iii | 3.179 | H192···H132x | 2.852 |
C3···H91i | 3.487 | H201···F21iv | 2.954 |
C3···H111ii | 3.138 | H201···C46xiv | 3.511 |
C3···H141ii | 2.842 | H201···H25iv | 3.405 |
C3···H231ii | 3.562 | H201···H412xii | 2.767 |
C3···H233ii | 3.432 | H201···H462xiv | 2.822 |
C3···H321i | 3.065 | H201···H463xiv | 3.577 |
C4···H91i | 3.575 | H202···F21iv | 3.132 |
C4···H101i | 3.171 | H202···H5iv | 3.416 |
C4···H111ii | 3.029 | H202···H8iv | 2.677 |
C4···H121ii | 3.576 | H202···H25iv | 3.267 |
C4···H132i | 3.482 | H231···F11ii | 3.083 |
C4···H141ii | 3.262 | H231···O21iv | 3.506 |
C4···H142i | 3.424 | H231···N24xii | 2.911 |
C4···H321i | 3.266 | H231···C2ii | 3.272 |
C5···H111ii | 3.309 | H231···C3ii | 3.562 |
C5···H121ii | 3.303 | H231···C43xii | 3.263 |
C5···H122ii | 3.478 | H231···C44xii | 3.257 |
C5···H192iv | 3.312 | H231···H2ii | 2.671 |
C5···H321i | 3.261 | H231···H25iv | 3.048 |
C6···H122ii | 3.582 | H231···H181i | 3.279 |
C6···H321i | 3.085 | H231···H432xii | 2.540 |
C9···H4vi | 3.504 | H232···O21iv | 3.124 |
C10···H4vi | 2.959 | H232···C10iv | 3.190 |
C10···H232iv | 3.190 | H232···C13iv | 3.515 |
C11···H171i | 3.178 | H232···C18i | 3.411 |
C12···H122ii | 3.532 | H232···H25iv | 3.106 |
C12···H142ix | 3.552 | H232···H101iv | 3.108 |
C13···H4vi | 3.046 | H232···H102iv | 2.480 |
C13···H182x | 3.328 | H232···H131iv | 3.108 |
C13···H232iv | 3.515 | H232···H132iv | 3.202 |
C14···H4vi | 3.385 | H232···H181i | 3.137 |
C14···H121ix | 3.524 | H232···H182i | 2.849 |
C16···H5vi | 3.524 | H232···H191i | 3.513 |
C16···H121ix | 3.517 | H233···F11ii | 3.252 |
C16···H172x | 3.323 | H233···C2ii | 3.309 |
C16···H192x | 3.540 | H233···C3ii | 3.432 |
C17···H112vi | 3.146 | H233···C18i | 3.228 |
C17···H172x | 3.376 | H233···H2ii | 3.066 |
C18···H132x | 3.401 | H233···H181i | 2.800 |
C18···H232vi | 3.411 | H233···H182i | 2.780 |
C18···H233vi | 3.228 | H321···C1vi | 2.928 |
C19···H5iv | 3.553 | H321···C2vi | 2.962 |
C19···H132x | 3.402 | H321···C3vi | 3.065 |
C19···H462xiv | 3.413 | H321···C4vi | 3.266 |
C20···H8iv | 3.558 | H321···C5vi | 3.261 |
C20···H462xiv | 3.556 | H321···C6vi | 3.085 |
C21···H25iv | 3.550 | H321···H2vi | 3.419 |
C21···H172x | 3.549 | H322···F21vi | 2.714 |
C22···H25iv | 3.498 | H322···C26vi | 3.564 |
C22···H102iv | 3.452 | H322···H27vi | 3.200 |
C22···H432xii | 3.167 | H322···H342v | 3.503 |
C23···H2ii | 3.302 | H322···H371v | 3.539 |
C23···H25iv | 3.360 | H331···O11vi | 3.227 |
C23···H102iv | 3.300 | H331···N24vii | 3.441 |
C23···H181i | 3.247 | H331···C1vi | 3.265 |
C23···H182i | 3.235 | H331···C2vi | 3.179 |
C23···H432xii | 3.249 | H331···C46vii | 3.421 |
C24···H92 | 2.948 | H331···H2vi | 3.023 |
C24···H101 | 3.207 | H331···H463vii | 2.657 |
C24···H102 | 3.504 | H332···O11vi | 3.093 |
C24···H372v | 3.480 | H332···N11vi | 3.412 |
C25···H92 | 3.005 | H332···C1vi | 3.379 |
C25···H102 | 3.443 | H332···C27vi | 3.178 |
C25···H402v | 3.516 | H332···H27vi | 2.682 |
C26···H92 | 3.304 | H332···H421xi | 3.435 |
C26···H322i | 3.564 | H332···H422xi | 3.236 |
C26···H402v | 3.118 | H341···C40i | 3.320 |
C27···H92 | 3.581 | H341···H401i | 3.059 |
C27···H332i | 3.178 | H341···H402i | 2.772 |
C27···H351viii | 3.427 | H341···H411i | 3.522 |
C27···H362i | 3.581 | H342···F21viii | 3.158 |
C27···H372i | 3.335 | H342···H322v | 3.503 |
C28···H92 | 3.550 | H342···H352v | 2.908 |
C28···H372v | 3.488 | H342···H402i | 2.890 |
C28···H421vii | 3.390 | H351···O22i | 3.073 |
C29···H92 | 3.229 | H351···C27viii | 3.427 |
C29···H372v | 3.092 | H351···H27viii | 2.976 |
C30···H371v | 3.176 | H351···H372v | 3.068 |
C30···H372v | 3.208 | H351···H402i | 2.995 |
C31···H431vii | 3.553 | H352···N22v | 3.093 |
C33···H27vi | 3.169 | H352···C34v | 3.308 |
C33···H463vii | 3.548 | H352···C35v | 3.578 |
C34···H352v | 3.308 | H352···C37v | 3.020 |
C34···H402i | 3.177 | H352···H27viii | 3.174 |
C35···H27viii | 3.505 | H352···H342v | 2.908 |
C35···H352v | 3.578 | H352···H352v | 2.922 |
C35···H371v | 3.474 | H352···H371v | 2.669 |
C35···H372v | 3.211 | H352···H372v | 2.600 |
C35···H402i | 3.580 | H361···H361vii | 3.277 |
C36···H27vi | 3.166 | H361···H411xi | 3.016 |
C36···H411xi | 3.233 | H361···H461vii | 3.446 |
C36···H421xi | 3.434 | H362···C27vi | 3.581 |
C37···H27vi | 3.287 | H362···C41xi | 3.241 |
C37···H352v | 3.020 | H362···C42xi | 3.097 |
C38···H401xi | 3.525 | H362···H27vi | 2.909 |
C39···H28vi | 3.517 | H362···H28vi | 3.417 |
C39···H401xi | 2.919 | H362···H401xi | 3.584 |
C39···H421xi | 3.432 | H362···H411xi | 2.581 |
C40···H341vi | 3.320 | H362···H421xi | 2.480 |
C40···H401xi | 3.301 | H362···H422xi | 3.181 |
C41···H362xi | 3.241 | H371···O21v | 3.456 |
C41···H461vi | 3.158 | H371···N21v | 3.090 |
C41···H463vi | 3.582 | H371···C30v | 3.176 |
C42···H362xi | 3.097 | H371···C35v | 3.474 |
C43···H31vii | 3.507 | H371···H322v | 3.539 |
C43···H231xiii | 3.263 | H371···H352v | 2.669 |
C44···H2iii | 3.575 | H372···C24v | 3.480 |
C44···H25v | 3.386 | H372···C27vi | 3.335 |
C44···H231xiii | 3.257 | H372···C28v | 3.488 |
C44···H401xi | 3.459 | H372···C29v | 3.092 |
C45···H2iii | 3.387 | H372···C30v | 3.208 |
C46···H2iii | 3.173 | H372···C35v | 3.211 |
C46···H201xv | 3.511 | H372···H27vi | 2.576 |
C46···H331vii | 3.421 | H372···H28vi | 3.240 |
C46···H411i | 3.115 | H372···H351v | 3.068 |
C46···H412i | 3.476 | H372···H352v | 2.600 |
H2···N24iii | 2.616 | H401···O22xi | 3.156 |
H2···C23ii | 3.302 | H401···N23xi | 2.915 |
H2···C44iii | 3.575 | H401···C38xi | 3.525 |
H2···C45iii | 3.387 | H401···C39xi | 2.919 |
H2···C46iii | 3.173 | H401···C40xi | 3.301 |
H2···H181ix | 3.011 | H401···C44xi | 3.459 |
H2···H231ii | 2.671 | H401···H341vi | 3.059 |
H2···H233ii | 3.066 | H401···H362xi | 3.584 |
H2···H321i | 3.419 | H401···H401xi | 2.726 |
H2···H331i | 3.023 | H402···F21v | 2.763 |
H2···H431iii | 3.393 | H402···C25v | 3.516 |
H2···H432iii | 3.535 | H402···C26v | 3.118 |
H2···H462iii | 3.358 | H402···C34vi | 3.177 |
H2···H463iii | 2.485 | H402···C35vi | 3.580 |
H4···N12i | 2.739 | H402···H25v | 3.549 |
H4···C9i | 3.504 | H402···H341vi | 2.772 |
H4···C10i | 2.959 | H402···H342vi | 2.890 |
H4···C13i | 3.046 | H402···H351vi | 2.995 |
H4···C14i | 3.385 | H411···C36xi | 3.233 |
H4···H91i | 3.016 | H411···C46vi | 3.115 |
H4···H101i | 2.473 | H411···H341vi | 3.522 |
H4···H111ii | 3.307 | H411···H361xi | 3.016 |
H4···H121ii | 3.571 | H411···H362xi | 2.581 |
H4···H132i | 2.711 | H411···H461vi | 2.466 |
H4···H141ii | 3.285 | H411···H462vi | 3.556 |
H4···H142i | 2.774 | H411···H463vi | 2.956 |
H5···O12i | 2.356 | H412···F21v | 2.991 |
H5···C16i | 3.524 | H412···C46vi | 3.476 |
H5···C19iv | 3.553 | H412···H25v | 3.221 |
H5···H121ii | 3.123 | H412···H201xiii | 2.767 |
H5···H122ii | 3.476 | H412···H461vi | 3.009 |
H5···H132i | 3.407 | H412···H462vi | 3.490 |
H5···H142i | 3.307 | H412···H463vi | 3.377 |
H5···H192iv | 2.661 | H421···O22xi | 2.743 |
H5···H202iv | 3.416 | H421···C28vii | 3.390 |
H8···C20iv | 3.558 | H421···C36xi | 3.434 |
H8···H202iv | 2.677 | H421···C39xi | 3.432 |
H25···N14iv | 2.652 | H421···H28vii | 2.821 |
H25···N23v | 3.324 | H421···H332xi | 3.435 |
H25···C21iv | 3.550 | H421···H362xi | 2.480 |
H25···C22iv | 3.498 | H422···O11vii | 2.731 |
H25···C23iv | 3.360 | H422···N11vii | 2.652 |
H25···C44v | 3.386 | H422···H332xi | 3.236 |
H25···H92 | 3.359 | H422···H362xi | 3.181 |
H25···H102 | 3.196 | H431···F11iii | 2.742 |
H25···H201iv | 3.405 | H431···C31vii | 3.553 |
H25···H202iv | 3.267 | H431···H2iii | 3.393 |
H25···H231iv | 3.048 | H431···H28vii | 3.410 |
H25···H232iv | 3.106 | H431···H31vii | 2.615 |
H25···H402v | 3.549 | H432···F11iii | 2.795 |
H25···H412v | 3.221 | H432···N14xiii | 3.209 |
H25···H432v | 3.453 | H432···C22xiii | 3.167 |
H27···N22i | 2.905 | H432···C23xiii | 3.249 |
H27···C33i | 3.169 | H432···H2iii | 3.535 |
H27···C35viii | 3.505 | H432···H25v | 3.453 |
H27···C36i | 3.166 | H432···H231xiii | 2.540 |
H27···C37i | 3.287 | H461···C41i | 3.158 |
H27···H322i | 3.200 | H461···H361vii | 3.446 |
H27···H332i | 2.682 | H461···H411i | 2.466 |
H27···H351viii | 2.976 | H461···H412i | 3.009 |
H27···H352viii | 3.174 | H462···O21v | 2.924 |
H27···H362i | 2.909 | H462···N21v | 3.068 |
H27···H372i | 2.576 | H462···C19xv | 3.413 |
H28···O22i | 2.341 | H462···C20xv | 3.556 |
H28···C39i | 3.517 | H462···H2iii | 3.358 |
H28···H362i | 3.417 | H462···H181xv | 3.121 |
H28···H372i | 3.240 | H462···H191xv | 2.714 |
H28···H421vii | 2.821 | H462···H201xv | 2.822 |
H28···H431vii | 3.410 | H462···H411i | 3.556 |
H31···C43vii | 3.507 | H462···H412i | 3.490 |
H31···H431vii | 2.615 | H463···O11iii | 3.001 |
H91···F11vi | 2.516 | H463···C1iii | 3.453 |
H91···C3vi | 3.487 | H463···C2iii | 3.179 |
H91···C4vi | 3.575 | H463···C33vii | 3.548 |
H91···H4vi | 3.016 | H463···C41i | 3.582 |
H91···H142ix | 3.493 | H463···H2iii | 2.485 |
H92···O21 | 3.504 | H463···H181xv | 3.456 |
H92···C24 | 2.948 | H463···H201xv | 3.577 |
H92···C25 | 3.005 | H463···H331vii | 2.657 |
H92···C26 | 3.304 | H463···H411i | 2.956 |
H92···C27 | 3.581 | H463···H412i | 3.377 |
| | | |
N11—O11—C1 | 106.9 (2) | C9—C10—H101 | 109.2 |
N21—O21—C24 | 106.86 (19) | C9—C10—H102 | 109.2 |
O11—N11—C7 | 107.1 (2) | H101—C10—H102 | 109.5 |
C10—N12—C11 | 109.1 (2) | N12—C11—H111 | 108.9 |
C10—N12—C13 | 112.1 (2) | N12—C11—H112 | 108.9 |
C11—N12—C13 | 111.3 (2) | C12—C11—H111 | 108.9 |
C16—N13—C17 | 115.0 (2) | C12—C11—H112 | 108.9 |
C16—N13—C21 | 121.9 (2) | H111—C11—H112 | 109.5 |
C17—N13—C21 | 123.1 (2) | C8—C12—H121 | 109.1 |
C21—N14—C22 | 118.0 (2) | C8—C12—H122 | 109.1 |
O21—N21—C30 | 107.3 (2) | C11—C12—H121 | 109.1 |
C33—N22—C34 | 110.5 (2) | C11—C12—H122 | 109.1 |
C33—N22—C36 | 112.0 (2) | H121—C12—H122 | 109.5 |
C34—N22—C36 | 111.2 (2) | N12—C13—H131 | 109.1 |
C39—N23—C40 | 115.7 (2) | N12—C13—H132 | 109.1 |
C39—N23—C44 | 122.1 (2) | C14—C13—H131 | 109.1 |
C40—N23—C44 | 122.2 (2) | C14—C13—H132 | 109.1 |
C44—N24—C45 | 118.0 (2) | H131—C13—H132 | 109.5 |
O11—C1—C2 | 125.6 (2) | C13—C14—H141 | 108.3 |
O11—C1—C6 | 110.2 (2) | C13—C14—H142 | 108.3 |
C2—C1—C6 | 124.2 (2) | C15—C14—H141 | 108.3 |
C1—C2—C3 | 113.2 (2) | C15—C14—H142 | 108.3 |
F11—C3—C2 | 117.4 (2) | H141—C14—H142 | 109.5 |
F11—C3—C4 | 116.9 (2) | N13—C17—H171 | 108.4 |
C2—C3—C4 | 125.6 (2) | N13—C17—H172 | 108.4 |
C3—C4—C5 | 118.7 (2) | C18—C17—H171 | 108.4 |
C4—C5—C6 | 118.3 (2) | C18—C17—H172 | 108.4 |
C1—C6—C5 | 120.0 (2) | H171—C17—H172 | 109.5 |
C1—C6—C7 | 103.6 (2) | C17—C18—H181 | 107.2 |
C5—C6—C7 | 136.3 (2) | C17—C18—H182 | 107.2 |
N11—C7—C6 | 112.1 (2) | C19—C18—H181 | 107.2 |
N11—C7—C8 | 121.1 (2) | C19—C18—H182 | 107.2 |
C6—C7—C8 | 126.8 (2) | H181—C18—H182 | 109.5 |
C7—C8—C9 | 114.6 (2) | C18—C19—H191 | 107.2 |
C7—C8—C12 | 111.8 (2) | C18—C19—H192 | 107.2 |
C9—C8—C12 | 109.1 (2) | C20—C19—H191 | 107.2 |
C8—C9—C10 | 111.7 (2) | C20—C19—H192 | 107.2 |
N12—C10—C9 | 110.5 (2) | H191—C19—H192 | 109.5 |
N12—C11—C12 | 111.7 (2) | C19—C20—H201 | 107.9 |
C8—C12—C11 | 110.9 (2) | C19—C20—H202 | 107.9 |
N12—C13—C14 | 111.1 (2) | C21—C20—H201 | 107.9 |
C13—C14—C15 | 114.2 (2) | C21—C20—H202 | 107.9 |
C14—C15—C16 | 116.9 (2) | H201—C20—H202 | 109.5 |
C14—C15—C22 | 124.5 (2) | C22—C23—H231 | 109.5 |
C16—C15—C22 | 118.6 (2) | C22—C23—H232 | 109.5 |
O12—C16—N13 | 119.1 (2) | C22—C23—H233 | 109.5 |
O12—C16—C15 | 125.4 (2) | H231—C23—H232 | 109.5 |
N13—C16—C15 | 115.4 (2) | H231—C23—H233 | 109.5 |
N13—C17—C18 | 113.5 (2) | H232—C23—H233 | 109.5 |
C17—C18—C19 | 118.6 (3) | C24—C25—H25 | 122.8 |
C18—C19—C20 | 118.4 (3) | C26—C25—H25 | 122.8 |
C19—C20—C21 | 115.6 (2) | C26—C27—H27 | 120.0 |
N13—C21—N14 | 122.8 (2) | C28—C27—H27 | 120.0 |
N13—C21—C20 | 119.7 (2) | C27—C28—H28 | 121.0 |
N14—C21—C20 | 117.5 (2) | C29—C28—H28 | 121.0 |
N14—C22—C15 | 123.2 (2) | C30—C31—H31 | 107.6 |
N14—C22—C23 | 113.8 (2) | C32—C31—H31 | 107.6 |
C15—C22—C23 | 122.9 (2) | C35—C31—H31 | 107.6 |
O21—C24—C25 | 125.1 (2) | C31—C32—H321 | 109.0 |
O21—C24—C29 | 111.1 (2) | C31—C32—H322 | 109.0 |
C25—C24—C29 | 123.9 (2) | C33—C32—H321 | 109.0 |
C24—C25—C26 | 114.3 (2) | C33—C32—H322 | 109.0 |
F21—C26—C25 | 117.7 (2) | H321—C32—H322 | 109.5 |
F21—C26—C27 | 118.2 (2) | N22—C33—H331 | 109.2 |
C25—C26—C27 | 124.1 (3) | N22—C33—H332 | 109.2 |
C26—C27—C28 | 120.0 (2) | C32—C33—H331 | 109.2 |
C27—C28—C29 | 118.1 (2) | C32—C33—H332 | 109.2 |
C24—C29—C28 | 119.5 (2) | H331—C33—H332 | 109.5 |
C24—C29—C30 | 104.0 (2) | N22—C34—H341 | 109.0 |
C28—C29—C30 | 136.5 (2) | N22—C34—H342 | 109.0 |
N21—C30—C29 | 110.8 (2) | C35—C34—H341 | 109.0 |
N21—C30—C31 | 120.8 (2) | C35—C34—H342 | 109.0 |
C29—C30—C31 | 128.4 (2) | H341—C34—H342 | 109.5 |
C30—C31—C32 | 113.0 (2) | C31—C35—H351 | 108.9 |
C30—C31—C35 | 112.2 (2) | C31—C35—H352 | 108.9 |
C32—C31—C35 | 108.7 (2) | C34—C35—H351 | 108.9 |
C31—C32—C33 | 111.3 (2) | C34—C35—H352 | 108.9 |
N22—C33—C32 | 110.5 (2) | H351—C35—H352 | 109.5 |
N22—C34—C35 | 111.5 (2) | N22—C36—H361 | 108.9 |
C31—C35—C34 | 111.7 (2) | N22—C36—H362 | 108.9 |
N22—C36—C37 | 111.9 (2) | C37—C36—H361 | 108.9 |
C36—C37—C38 | 113.1 (2) | C37—C36—H362 | 108.9 |
C37—C38—C39 | 117.7 (2) | H361—C36—H362 | 109.5 |
C37—C38—C45 | 124.1 (2) | C36—C37—H371 | 108.6 |
C39—C38—C45 | 118.1 (2) | C36—C37—H372 | 108.6 |
O22—C39—N23 | 119.8 (2) | C38—C37—H371 | 108.6 |
O22—C39—C38 | 124.7 (2) | C38—C37—H372 | 108.6 |
N23—C39—C38 | 115.5 (2) | H371—C37—H372 | 109.5 |
N23—C40—C41 | 113.3 (2) | N23—C40—H401 | 108.5 |
C40—C41—C42 | 114.5 (2) | N23—C40—H402 | 108.5 |
C41—C42—C43 | 114.2 (4) | C41—C40—H401 | 108.5 |
C42—C43—C44 | 117.0 (3) | C41—C40—H402 | 108.5 |
N23—C44—N24 | 122.8 (2) | H401—C40—H402 | 109.5 |
N23—C44—C43 | 119.3 (2) | C40—C41—H411 | 108.2 |
N24—C44—C43 | 117.9 (2) | C40—C41—H412 | 108.2 |
N24—C45—C38 | 123.4 (2) | C42—C41—H411 | 108.2 |
N24—C45—C46 | 114.2 (2) | C42—C41—H412 | 108.2 |
C38—C45—C46 | 122.4 (2) | H411—C41—H412 | 109.5 |
C1—C2—H2 | 123.4 | C41—C42—H421 | 108.3 |
C3—C2—H2 | 123.4 | C41—C42—H422 | 108.3 |
C3—C4—H4 | 120.7 | C43—C42—H421 | 108.3 |
C5—C4—H4 | 120.7 | C43—C42—H422 | 108.3 |
C4—C5—H5 | 120.9 | H421—C42—H422 | 109.5 |
C6—C5—H5 | 120.9 | C42—C43—H431 | 107.6 |
C7—C8—H8 | 107.0 | C42—C43—H432 | 107.6 |
C9—C8—H8 | 107.0 | C44—C43—H431 | 107.6 |
C12—C8—H8 | 107.0 | C44—C43—H432 | 107.6 |
C8—C9—H91 | 108.9 | H431—C43—H432 | 109.5 |
C8—C9—H92 | 108.9 | C45—C46—H461 | 109.5 |
C10—C9—H91 | 108.9 | C45—C46—H462 | 109.5 |
C10—C9—H92 | 108.9 | C45—C46—H463 | 109.5 |
H91—C9—H92 | 109.5 | H461—C46—H462 | 109.5 |
N12—C10—H101 | 109.2 | H461—C46—H463 | 109.5 |
N12—C10—H102 | 109.2 | H462—C46—H463 | 109.5 |
| | | |
N11—O11—C1—C2 | −175.9 (3) | N11—C7—C8—C12 | 104.1 (3) |
N11—O11—C1—C6 | 2.2 (3) | C6—C7—C8—C9 | 156.5 (3) |
C1—O11—N11—C7 | −0.9 (3) | C6—C7—C8—C12 | −78.7 (4) |
N21—O21—C24—C25 | −178.9 (2) | C7—C8—C9—C10 | −180.0 (2) |
N21—O21—C24—C29 | 0.2 (3) | C7—C8—C12—C11 | −179.5 (2) |
C24—O21—N21—C30 | −0.3 (3) | C9—C8—C12—C11 | −51.7 (3) |
O11—N11—C7—C6 | −0.7 (3) | C12—C8—C9—C10 | 53.8 (4) |
O11—N11—C7—C8 | 176.9 (2) | C8—C9—C10—N12 | −59.7 (3) |
C10—N12—C11—C12 | −60.4 (3) | N12—C11—C12—C8 | 56.4 (3) |
C11—N12—C10—C9 | 61.5 (3) | N12—C13—C14—C15 | 178.1 (2) |
C10—N12—C13—C14 | 160.2 (2) | C13—C14—C15—C16 | 90.8 (3) |
C13—N12—C10—C9 | −174.8 (2) | C13—C14—C15—C22 | −91.7 (3) |
C11—N12—C13—C14 | −77.3 (3) | C14—C15—C16—O12 | −4.9 (5) |
C13—N12—C11—C12 | 175.3 (2) | C14—C15—C16—N13 | 176.4 (2) |
C16—N13—C17—C18 | 173.4 (3) | C14—C15—C22—N14 | −176.6 (3) |
C17—N13—C16—O12 | 0.7 (4) | C14—C15—C22—C23 | 4.1 (5) |
C17—N13—C16—C15 | 179.5 (3) | C16—C15—C22—N14 | 0.9 (5) |
C16—N13—C21—N14 | −0.2 (4) | C16—C15—C22—C23 | −178.4 (3) |
C16—N13—C21—C20 | −179.6 (3) | C22—C15—C16—O12 | 177.5 (3) |
C21—N13—C16—O12 | −177.8 (3) | C22—C15—C16—N13 | −1.3 (4) |
C21—N13—C16—C15 | 1.0 (4) | N13—C17—C18—C19 | 27.1 (6) |
C17—N13—C21—N14 | −178.7 (3) | C17—C18—C19—C20 | −40.8 (7) |
C17—N13—C21—C20 | 2.0 (5) | C18—C19—C20—C21 | 32.7 (6) |
C21—N13—C17—C18 | −8.1 (5) | C19—C20—C21—N13 | −13.3 (5) |
C21—N14—C22—C15 | −0.1 (3) | C19—C20—C21—N14 | 167.3 (3) |
C21—N14—C22—C23 | 179.2 (3) | O21—C24—C25—C26 | −179.4 (2) |
C22—N14—C21—N13 | −0.2 (5) | O21—C24—C29—C28 | 179.6 (2) |
C22—N14—C21—C20 | 179.2 (3) | O21—C24—C29—C30 | −0.0 (2) |
O21—N21—C30—C29 | 0.3 (3) | C25—C24—C29—C28 | −1.3 (4) |
O21—N21—C30—C31 | 178.2 (2) | C25—C24—C29—C30 | 179.1 (2) |
C33—N22—C34—C35 | −59.0 (3) | C29—C24—C25—C26 | 1.6 (4) |
C34—N22—C33—C32 | 60.7 (3) | C24—C25—C26—F21 | 179.6 (2) |
C33—N22—C36—C37 | 153.4 (2) | C24—C25—C26—C27 | −0.7 (4) |
C36—N22—C33—C32 | −174.8 (2) | F21—C26—C27—C28 | 179.2 (3) |
C34—N22—C36—C37 | −82.4 (2) | C25—C26—C27—C28 | −0.5 (5) |
C36—N22—C34—C35 | 176.0 (2) | C26—C27—C28—C29 | 0.9 (4) |
C39—N23—C40—C41 | 164.1 (3) | C27—C28—C29—C24 | −0.0 (3) |
C40—N23—C39—O22 | 3.7 (4) | C27—C28—C29—C30 | 179.4 (3) |
C40—N23—C39—C38 | −177.8 (2) | C24—C29—C30—N21 | −0.1 (3) |
C39—N23—C44—N24 | −0.9 (4) | C24—C29—C30—C31 | −177.9 (2) |
C39—N23—C44—C43 | −179.2 (3) | C28—C29—C30—N21 | −179.7 (3) |
C44—N23—C39—O22 | −176.9 (2) | C28—C29—C30—C31 | 2.6 (5) |
C44—N23—C39—C38 | 1.6 (4) | N21—C30—C31—C32 | −3.2 (4) |
C40—N23—C44—N24 | 178.4 (3) | N21—C30—C31—C35 | 120.1 (3) |
C40—N23—C44—C43 | 0.2 (4) | C29—C30—C31—C32 | 174.4 (2) |
C44—N23—C40—C41 | −15.3 (4) | C29—C30—C31—C35 | −62.3 (3) |
C44—N24—C45—C38 | 2.6 (4) | C30—C31—C32—C33 | 179.4 (2) |
C44—N24—C45—C46 | −178.3 (2) | C30—C31—C35—C34 | −177.9 (2) |
C45—N24—C44—N23 | −1.1 (4) | C32—C31—C35—C34 | −52.3 (3) |
C45—N24—C44—C43 | 177.1 (3) | C35—C31—C32—C33 | 54.2 (3) |
O11—C1—C2—C3 | 178.2 (3) | C31—C32—C33—N22 | −59.2 (3) |
O11—C1—C6—C5 | −179.3 (2) | N22—C34—C35—C31 | 55.5 (3) |
O11—C1—C6—C7 | −2.5 (3) | N22—C36—C37—C38 | 176.1 (2) |
C2—C1—C6—C5 | −1.3 (5) | C36—C37—C38—C39 | 86.3 (3) |
C2—C1—C6—C7 | 175.6 (3) | C36—C37—C38—C45 | −97.5 (3) |
C6—C1—C2—C3 | 0.4 (4) | C37—C38—C39—O22 | −5.4 (4) |
C1—C2—C3—F11 | −179.5 (2) | C37—C38—C39—N23 | 176.2 (2) |
C1—C2—C3—C4 | 1.8 (4) | C37—C38—C45—N24 | −178.0 (2) |
F11—C3—C4—C5 | 178.2 (2) | C37—C38—C45—C46 | 3.0 (4) |
C2—C3—C4—C5 | −3.0 (5) | C39—C38—C45—N24 | −1.8 (4) |
C3—C4—C5—C6 | 1.9 (4) | C39—C38—C45—C46 | 179.1 (2) |
C4—C5—C6—C1 | 0.0 (4) | C45—C38—C39—O22 | 178.2 (3) |
C4—C5—C6—C7 | −175.6 (3) | C45—C38—C39—N23 | −0.2 (4) |
C1—C6—C7—N11 | 2.0 (3) | N23—C40—C41—C42 | 41.2 (5) |
C1—C6—C7—C8 | −175.5 (3) | C40—C41—C42—C43 | −52.4 (5) |
C5—C6—C7—N11 | 178.0 (3) | C41—C42—C43—C44 | 36.3 (5) |
C5—C6—C7—C8 | 0.6 (6) | C42—C43—C44—N23 | −10.3 (5) |
N11—C7—C8—C9 | −20.7 (4) | C42—C43—C44—N24 | 171.4 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+1, −y, −z+1; (v) −x+2, −y+1, −z; (vi) x+1, y, z; (vii) −x+2, −y+2, −z; (viii) −x+1, −y+1, −z; (ix) −x+1, −y+1, −z+1; (x) −x+2, −y, −z+1; (xi) −x+3, −y+2, −z; (xii) x−1, y−1, z+1; (xiii) x+1, y+1, z−1; (xiv) x, y−1, z+1; (xv) x, y+1, z−1. |
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