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Conformational analyses and structural comparison of the title compound, C18H13BrN4O3·C2H6O, and the related compound 4-(4-methoxyphenyl)-3-phenyl-2,4,8,10-tetraazaspiro[5.4]dec-1-ene-6,8,10-trione acetone solvate monohydrate [Bruno, Rotondo, Nicoló, Foti, Grassi & Risitano (2005). Acta Cryst. E61, o139-o141], co-crystallized with solvent molecules, are presented. Both compounds were synthesized by the cycloaddition of C-H and C-Br nitrilimines, generated in situ, starting from the same substrate [Foti, Grassi & Risitano (2005). Synlett. Submitted]. However, different experimental conditions led to products with reverse regioselectivity.
Supporting information
CCDC reference: 262475
Key indicators
- Single-crystal X-ray study
- T = 571 K
- Mean (C-C) = 0.008 Å
- R factor = 0.056
- wR factor = 0.141
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level B
PLAT057_ALERT_3_B Correction for Absorption Required RT(exp) ... 1.28
Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1B .. O2A .. 3.27 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 18
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1989); cell refinement: XSCANS; data reduction: XPREPW (Bruker, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (Bruker, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995) and WinGX-PC (Version 1.6.4.05; Farrugia,
1999).
3-Bromo-1,4-diphenyl-1,2,7,9-tetraazaspiro[5.4]dec-2-ene-6,8,10-trione acetone
solvate
top
Crystal data top
C18H13BrN4O3·C2H6O | Z = 4 |
Mr = 459.3 | F(000) = 936 |
Triclinic, P1 | Dx = 1.495 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.027 (4) Å | Cell parameters from 27 reflections |
b = 13.380 (5) Å | θ = 3.4–18.0° |
c = 13.416 (3) Å | µ = 2.05 mm−1 |
α = 71.32 (3)° | T = 571 K |
β = 86.159 (13)° | Prism, colourless |
γ = 87.84 (3)° | 0.4 × 0.38 × 0.26 mm |
V = 2040.3 (12) Å3 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.019 |
ω scans | θmax = 25.7°, θmin = 1.9° |
Absorption correction: ψ scan (North et al., 1968) | h = −14→1 |
Tmin = 0.484, Tmax = 0.584 | k = −16→16 |
8832 measured reflections | l = −16→16 |
7668 independent reflections | 3 standard reflections every 197 reflections |
4687 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0501P)2 + 3.1246P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.056 | (Δ/σ)max = 0.002 |
wR(F2) = 0.141 | Δρmax = 1.10 e Å−3 |
S = 1.02 | Δρmin = −0.79 e Å−3 |
7668 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
526 parameters | Extinction coefficient: 0.0028 (5) |
1 restraint | |
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 | |
Br1A | 0.40708 (5) | 0.57424 (5) | 0.14171 (5) | 0.0853 (3) | |
O1A | 0.5322 (3) | 0.3198 (3) | 0.5256 (3) | 0.0588 (9) | |
O2A | 0.3321 (3) | 0.0351 (3) | 0.5499 (3) | 0.0756 (12) | |
O3A | 0.5342 (3) | 0.1859 (3) | 0.2471 (3) | 0.0559 (9) | |
C1A | 0.4907 (4) | 0.2661 (4) | 0.4821 (4) | 0.0388 (10) | |
N2A | 0.4254 (3) | 0.1821 (3) | 0.5351 (3) | 0.0410 (9) | |
H2A | 0.4054 | 0.1757 | 0.5996 | 0.049* | |
C3A | 0.3887 (4) | 0.1076 (4) | 0.4968 (4) | 0.0464 (12) | |
N4A | 0.4237 (3) | 0.1166 (3) | 0.3946 (3) | 0.0464 (10) | |
H4A | 0.4003 | 0.0701 | 0.3695 | 0.056* | |
C5A | 0.4918 (4) | 0.1920 (4) | 0.3295 (4) | 0.0408 (11) | |
C6A | 0.4998 (3) | 0.2906 (3) | 0.3626 (3) | 0.0384 (10) | |
N7A | 0.5994 (3) | 0.3497 (3) | 0.3161 (3) | 0.0514 (11) | |
N8A | 0.5776 (3) | 0.4442 (3) | 0.2402 (3) | 0.0534 (11) | |
C9A | 0.4724 (4) | 0.4557 (4) | 0.2355 (4) | 0.0532 (13) | |
C10A | 0.4020 (4) | 0.3684 (3) | 0.3087 (3) | 0.0405 (11) | |
H10A | 0.362 | 0.3355 | 0.2663 | 0.049* | |
C11A | 0.3186 (3) | 0.4019 (3) | 0.3817 (3) | 0.0386 (10) | |
C12A | 0.3416 (4) | 0.4799 (4) | 0.4243 (4) | 0.0488 (12) | |
H12A | 0.4096 | 0.5139 | 0.4067 | 0.059* | |
C13A | 0.2657 (5) | 0.5079 (4) | 0.4923 (4) | 0.0601 (14) | |
H13A | 0.2824 | 0.5604 | 0.5204 | 0.072* | |
C14A | 0.1653 (5) | 0.4585 (5) | 0.5187 (4) | 0.0636 (15) | |
H14A | 0.114 | 0.4774 | 0.5649 | 0.076* | |
C15A | 0.1400 (4) | 0.3816 (5) | 0.4775 (4) | 0.0613 (15) | |
H15A | 0.0716 | 0.3484 | 0.4958 | 0.074* | |
C16A | 0.2159 (4) | 0.3528 (4) | 0.4086 (4) | 0.0486 (12) | |
H16A | 0.1982 | 0.3007 | 0.3804 | 0.058* | |
C17A | 0.7087 (4) | 0.3153 (4) | 0.3370 (4) | 0.0403 (11) | |
C18A | 0.7972 (4) | 0.3811 (4) | 0.2907 (4) | 0.0509 (13) | |
H18A | 0.7844 | 0.4485 | 0.2445 | 0.061* | |
C19A | 0.9057 (4) | 0.3448 (5) | 0.3142 (5) | 0.0631 (15) | |
H19A | 0.965 | 0.3892 | 0.2839 | 0.076* | |
C20A | 0.9270 (4) | 0.2458 (5) | 0.3805 (4) | 0.0594 (14) | |
H20A | 1 | 0.2228 | 0.3945 | 0.071* | |
C21A | 0.8398 (4) | 0.1804 (4) | 0.4264 (4) | 0.0520 (13) | |
H21A | 0.854 | 0.1129 | 0.4716 | 0.062* | |
C22A | 0.7311 (4) | 0.2141 (4) | 0.4062 (4) | 0.0459 (12) | |
H22A | 0.6726 | 0.1695 | 0.4386 | 0.055* | |
Br1B | 1.08077 (5) | 0.08684 (5) | 0.63063 (5) | 0.0677 (2) | |
O1B | 0.6316 (3) | 0.0522 (3) | 0.6749 (3) | 0.0495 (8) | |
O2B | 0.5260 (3) | 0.1296 (3) | 0.9702 (3) | 0.0775 (12) | |
O3B | 0.8586 (3) | −0.0363 (3) | 0.9653 (3) | 0.0529 (9) | |
C1B | 0.6562 (4) | 0.0555 (3) | 0.7601 (4) | 0.0378 (10) | |
N2B | 0.5828 (3) | 0.0932 (3) | 0.8215 (3) | 0.0486 (10) | |
H2B | 0.5204 | 0.1181 | 0.7952 | 0.058* | |
C3B | 0.5981 (4) | 0.0958 (4) | 0.9216 (4) | 0.0484 (12) | |
N4B | 0.6983 (3) | 0.0571 (3) | 0.9620 (3) | 0.0454 (10) | |
H4B | 0.7104 | 0.0632 | 1.0222 | 0.055* | |
C5B | 0.7814 (4) | 0.0100 (4) | 0.9173 (3) | 0.0393 (10) | |
C6B | 0.7728 (3) | 0.0244 (3) | 0.7998 (3) | 0.0355 (10) | |
N7B | 0.8144 (3) | −0.0706 (3) | 0.7751 (3) | 0.0436 (9) | |
N8B | 0.9211 (3) | −0.0574 (3) | 0.7276 (3) | 0.0493 (10) | |
C9B | 0.9460 (4) | 0.0390 (4) | 0.7041 (4) | 0.0467 (12) | |
C10B | 0.8564 (4) | 0.1117 (4) | 0.7296 (3) | 0.0411 (11) | |
H10B | 0.8206 | 0.149 | 0.664 | 0.049* | |
C11B | 0.8956 (4) | 0.1937 (3) | 0.7737 (4) | 0.0405 (11) | |
C12B | 0.8530 (5) | 0.2954 (4) | 0.7360 (4) | 0.0597 (14) | |
H12B | 0.7982 | 0.311 | 0.6873 | 0.072* | |
C13B | 0.8915 (5) | 0.3735 (4) | 0.7704 (5) | 0.0732 (17) | |
H13B | 0.8635 | 0.442 | 0.7435 | 0.088* | |
C14B | 0.9703 (5) | 0.3521 (4) | 0.8434 (5) | 0.0662 (16) | |
H14B | 0.9951 | 0.4053 | 0.8667 | 0.079* | |
C15B | 1.0129 (4) | 0.2503 (4) | 0.8825 (4) | 0.0541 (13) | |
H15B | 1.0664 | 0.2349 | 0.9324 | 0.065* | |
C16B | 0.9760 (4) | 0.1722 (4) | 0.8475 (4) | 0.0471 (12) | |
H16B | 1.0053 | 0.1041 | 0.8736 | 0.056* | |
C17B | 0.7867 (4) | −0.1741 (4) | 0.8397 (4) | 0.0438 (11) | |
C18B | 0.8610 (5) | −0.2574 (4) | 0.8481 (4) | 0.0607 (14) | |
H18B | 0.9306 | −0.2458 | 0.8121 | 0.073* | |
C19B | 0.8317 (6) | −0.3578 (4) | 0.9099 (5) | 0.0781 (19) | |
H19B | 0.8819 | −0.4135 | 0.915 | 0.094* | |
C20B | 0.7296 (6) | −0.3773 (5) | 0.9644 (5) | 0.0810 (19) | |
H20B | 0.7107 | −0.4452 | 1.0065 | 0.097* | |
C21B | 0.6556 (5) | −0.2935 (5) | 0.9549 (5) | 0.0702 (16) | |
H21B | 0.5861 | −0.3052 | 0.9911 | 0.084* | |
C22B | 0.6834 (4) | −0.1935 (4) | 0.8931 (4) | 0.0549 (13) | |
H22B | 0.6323 | −0.1382 | 0.887 | 0.066* | |
O01A | 0.3614 (3) | 0.1293 (2) | 0.7526 (2) | 0.0471 (8) | |
H01A | 0.3342 | 0.0705 | 0.7718 | 0.071* | |
C02A | 0.2901 (5) | 0.1996 (5) | 0.7893 (6) | 0.083 (2) | |
H02A | 0.2811 | 0.1731 | 0.8656 | 0.125* | |
H02B | 0.2172 | 0.2029 | 0.7615 | 0.125* | |
C03A | 0.3359 (8) | 0.3041 (5) | 0.7568 (6) | 0.119 (3) | |
H03A | 0.2833 | 0.3517 | 0.7757 | 0.178* | |
H03B | 0.3512 | 0.3278 | 0.6818 | 0.178* | |
H03C | 0.4038 | 0.3024 | 0.7912 | 0.178* | |
O01B | 0.7108 (3) | 0.0800 (3) | 0.1625 (3) | 0.0558 (9) | |
H01B | 0.6558 | 0.104 | 0.1872 | 0.084* | |
C02B | 0.8044 (5) | 0.1478 (5) | 0.1523 (5) | 0.0742 (17) | |
H02C | 0.8696 | 0.118 | 0.1249 | 0.111* | |
H02D | 0.8199 | 0.1504 | 0.2214 | 0.111* | |
C03B | 0.7839 (6) | 0.2561 (5) | 0.0817 (5) | 0.090 (2) | |
H03E | 0.8483 | 0.2981 | 0.077 | 0.135* | |
H03D | 0.7206 | 0.2867 | 0.1094 | 0.135* | |
H03F | 0.7697 | 0.2541 | 0.0128 | 0.135* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1A | 0.0654 (4) | 0.0705 (4) | 0.0848 (5) | 0.0068 (3) | 0.0051 (3) | 0.0217 (3) |
O1A | 0.060 (2) | 0.063 (2) | 0.066 (2) | −0.0099 (19) | −0.0121 (18) | −0.035 (2) |
O2A | 0.085 (3) | 0.067 (3) | 0.073 (3) | −0.038 (2) | 0.028 (2) | −0.023 (2) |
O3A | 0.054 (2) | 0.073 (2) | 0.0438 (19) | 0.0048 (18) | 0.0096 (16) | −0.0251 (18) |
C1A | 0.032 (2) | 0.040 (3) | 0.045 (3) | 0.001 (2) | −0.004 (2) | −0.014 (2) |
N2A | 0.044 (2) | 0.048 (2) | 0.033 (2) | −0.0062 (18) | 0.0035 (17) | −0.0157 (18) |
C3A | 0.045 (3) | 0.045 (3) | 0.050 (3) | −0.009 (2) | 0.009 (2) | −0.017 (2) |
N4A | 0.052 (2) | 0.045 (2) | 0.049 (2) | −0.0151 (19) | 0.0084 (19) | −0.0253 (19) |
C5A | 0.034 (2) | 0.045 (3) | 0.045 (3) | 0.000 (2) | 0.002 (2) | −0.017 (2) |
C6A | 0.030 (2) | 0.038 (3) | 0.045 (3) | −0.0055 (19) | 0.0040 (19) | −0.012 (2) |
N7A | 0.031 (2) | 0.046 (2) | 0.066 (3) | −0.0067 (18) | 0.0048 (19) | −0.002 (2) |
N8A | 0.042 (2) | 0.046 (2) | 0.061 (3) | −0.0015 (19) | 0.007 (2) | −0.002 (2) |
C9A | 0.048 (3) | 0.047 (3) | 0.051 (3) | 0.001 (2) | 0.007 (2) | 0.002 (2) |
C10A | 0.034 (2) | 0.041 (3) | 0.046 (3) | −0.002 (2) | 0.000 (2) | −0.013 (2) |
C11A | 0.032 (2) | 0.036 (2) | 0.045 (3) | 0.0007 (19) | −0.002 (2) | −0.010 (2) |
C12A | 0.042 (3) | 0.046 (3) | 0.060 (3) | −0.006 (2) | 0.000 (2) | −0.020 (2) |
C13A | 0.063 (4) | 0.057 (3) | 0.068 (4) | 0.006 (3) | −0.005 (3) | −0.032 (3) |
C14A | 0.053 (3) | 0.073 (4) | 0.067 (4) | 0.010 (3) | 0.010 (3) | −0.030 (3) |
C15A | 0.035 (3) | 0.074 (4) | 0.073 (4) | −0.003 (3) | 0.014 (3) | −0.023 (3) |
C16A | 0.037 (3) | 0.044 (3) | 0.064 (3) | −0.008 (2) | −0.002 (2) | −0.017 (2) |
C17A | 0.031 (2) | 0.046 (3) | 0.048 (3) | −0.004 (2) | 0.005 (2) | −0.021 (2) |
C18A | 0.042 (3) | 0.050 (3) | 0.060 (3) | −0.010 (2) | 0.008 (2) | −0.019 (3) |
C19A | 0.037 (3) | 0.075 (4) | 0.079 (4) | −0.018 (3) | 0.015 (3) | −0.028 (3) |
C20A | 0.037 (3) | 0.075 (4) | 0.071 (4) | 0.001 (3) | 0.000 (3) | −0.032 (3) |
C21A | 0.049 (3) | 0.059 (3) | 0.054 (3) | 0.004 (3) | −0.006 (2) | −0.027 (3) |
C22A | 0.037 (3) | 0.051 (3) | 0.053 (3) | −0.009 (2) | 0.000 (2) | −0.020 (2) |
Br1B | 0.0465 (3) | 0.0830 (4) | 0.0679 (4) | −0.0114 (3) | 0.0205 (3) | −0.0197 (3) |
O1B | 0.053 (2) | 0.056 (2) | 0.047 (2) | −0.0014 (16) | −0.0110 (16) | −0.0258 (17) |
O2B | 0.062 (2) | 0.112 (3) | 0.065 (2) | 0.029 (2) | 0.006 (2) | −0.043 (2) |
O3B | 0.046 (2) | 0.060 (2) | 0.047 (2) | 0.0061 (17) | −0.0134 (16) | −0.0073 (16) |
C1B | 0.037 (2) | 0.037 (2) | 0.041 (3) | −0.001 (2) | −0.002 (2) | −0.014 (2) |
N2B | 0.034 (2) | 0.069 (3) | 0.045 (2) | 0.010 (2) | −0.0052 (18) | −0.022 (2) |
C3B | 0.045 (3) | 0.059 (3) | 0.044 (3) | 0.007 (2) | 0.003 (2) | −0.021 (2) |
N4B | 0.043 (2) | 0.063 (3) | 0.034 (2) | 0.004 (2) | −0.0034 (18) | −0.0212 (19) |
C5B | 0.034 (2) | 0.042 (3) | 0.040 (3) | −0.005 (2) | −0.001 (2) | −0.010 (2) |
C6B | 0.033 (2) | 0.039 (2) | 0.034 (2) | 0.0013 (19) | −0.0001 (19) | −0.0114 (19) |
N7B | 0.041 (2) | 0.042 (2) | 0.048 (2) | −0.0003 (18) | 0.0114 (18) | −0.0170 (18) |
N8B | 0.040 (2) | 0.055 (3) | 0.052 (2) | 0.002 (2) | 0.0116 (19) | −0.019 (2) |
C9B | 0.037 (3) | 0.056 (3) | 0.044 (3) | 0.000 (2) | 0.007 (2) | −0.014 (2) |
C10B | 0.036 (2) | 0.046 (3) | 0.037 (2) | −0.002 (2) | 0.002 (2) | −0.009 (2) |
C11B | 0.034 (2) | 0.039 (3) | 0.046 (3) | −0.001 (2) | 0.003 (2) | −0.010 (2) |
C12B | 0.060 (3) | 0.044 (3) | 0.069 (4) | 0.007 (3) | −0.015 (3) | −0.009 (3) |
C13B | 0.075 (4) | 0.034 (3) | 0.102 (5) | −0.001 (3) | −0.007 (4) | −0.010 (3) |
C14B | 0.066 (4) | 0.055 (4) | 0.085 (4) | −0.010 (3) | 0.005 (3) | −0.034 (3) |
C15B | 0.047 (3) | 0.057 (3) | 0.064 (3) | −0.006 (3) | −0.004 (3) | −0.027 (3) |
C16B | 0.039 (3) | 0.045 (3) | 0.055 (3) | 0.004 (2) | −0.004 (2) | −0.014 (2) |
C17B | 0.043 (3) | 0.045 (3) | 0.044 (3) | −0.001 (2) | 0.003 (2) | −0.017 (2) |
C18B | 0.058 (3) | 0.052 (3) | 0.070 (4) | 0.002 (3) | 0.011 (3) | −0.019 (3) |
C19B | 0.092 (5) | 0.044 (3) | 0.090 (5) | 0.017 (3) | 0.000 (4) | −0.014 (3) |
C20B | 0.114 (6) | 0.051 (4) | 0.071 (4) | −0.011 (4) | 0.003 (4) | −0.010 (3) |
C21B | 0.080 (4) | 0.060 (4) | 0.065 (4) | −0.019 (3) | 0.014 (3) | −0.014 (3) |
C22B | 0.049 (3) | 0.050 (3) | 0.062 (3) | −0.001 (2) | 0.007 (3) | −0.015 (3) |
O01A | 0.0435 (18) | 0.052 (2) | 0.0453 (18) | −0.0014 (15) | 0.0032 (15) | −0.0152 (15) |
C02A | 0.057 (4) | 0.082 (5) | 0.121 (6) | 0.002 (3) | 0.019 (4) | −0.052 (4) |
C03A | 0.184 (9) | 0.065 (5) | 0.107 (6) | 0.008 (5) | 0.011 (6) | −0.032 (4) |
O01B | 0.060 (2) | 0.060 (2) | 0.049 (2) | 0.0059 (18) | 0.0019 (17) | −0.0219 (17) |
C02B | 0.065 (4) | 0.103 (5) | 0.066 (4) | −0.004 (4) | −0.007 (3) | −0.043 (4) |
C03B | 0.106 (6) | 0.086 (5) | 0.078 (5) | −0.025 (4) | 0.015 (4) | −0.029 (4) |
Geometric parameters (Å, º) top
Br1A—C9A | 1.864 (5) | C3B—N4B | 1.369 (6) |
O1A—C1A | 1.201 (5) | N4B—C5B | 1.368 (6) |
O2A—C3A | 1.206 (5) | N4B—H4B | 0.86 |
O3A—C5A | 1.211 (5) | C5B—C6B | 1.536 (6) |
C1A—N2A | 1.366 (5) | C6B—N7B | 1.474 (5) |
C1A—C6A | 1.527 (6) | C6B—C10B | 1.587 (6) |
N2A—C3A | 1.357 (6) | N7B—N8B | 1.385 (5) |
N2A—H2A | 0.86 | N7B—C17B | 1.417 (6) |
C3A—N4A | 1.376 (6) | N8B—C9B | 1.269 (6) |
N4A—C5A | 1.362 (6) | C9B—C10B | 1.520 (6) |
N4A—H4A | 0.86 | C10B—C11B | 1.507 (6) |
C5A—C6A | 1.530 (6) | C10B—H10B | 0.98 |
C6A—N7A | 1.451 (5) | C11B—C12B | 1.382 (6) |
C6A—C10A | 1.590 (6) | C11B—C16B | 1.386 (6) |
N7A—N8A | 1.374 (5) | C12B—C13B | 1.377 (8) |
N7A—C17A | 1.392 (6) | C12B—H12B | 0.93 |
N8A—C9A | 1.273 (6) | C13B—C14B | 1.365 (8) |
C9A—C10A | 1.508 (6) | C13B—H13B | 0.93 |
C10A—C11A | 1.511 (6) | C14B—C15B | 1.385 (7) |
C10A—H10A | 0.98 | C14B—H14B | 0.93 |
C11A—C12A | 1.385 (6) | C15B—C16B | 1.374 (7) |
C11A—C16A | 1.392 (6) | C15B—H15B | 0.93 |
C12A—C13A | 1.374 (7) | C16B—H16B | 0.93 |
C12A—H12A | 0.93 | C17B—C22B | 1.382 (6) |
C13A—C14A | 1.369 (7) | C17B—C18B | 1.384 (7) |
C13A—H13A | 0.93 | C18B—C19B | 1.378 (8) |
C14A—C15A | 1.366 (7) | C18B—H18B | 0.93 |
C14A—H14A | 0.93 | C19B—C20B | 1.376 (9) |
C15A—C16A | 1.388 (7) | C19B—H19B | 0.93 |
C15A—H15A | 0.93 | C20B—C21B | 1.384 (8) |
C16A—H16A | 0.93 | C20B—H20B | 0.93 |
C17A—C18A | 1.388 (6) | C21B—C22B | 1.369 (7) |
C17A—C22A | 1.403 (6) | C21B—H21B | 0.93 |
C18A—C19A | 1.395 (7) | C22B—H22B | 0.93 |
C18A—H18A | 0.93 | O01A—C02A | 1.429 (6) |
C19A—C20A | 1.365 (8) | O01A—H01A | 0.82 |
C19A—H19A | 0.93 | C02A—C03A | 1.444 (7) |
C20A—C21A | 1.371 (7) | C02A—H02A | 0.97 |
C20A—H20A | 0.93 | C02A—H02B | 0.97 |
C21A—C22A | 1.382 (6) | C03A—H03A | 0.96 |
C21A—H21A | 0.93 | C03A—H03B | 0.96 |
C22A—H22A | 0.93 | C03A—H03C | 0.96 |
Br1B—C9B | 1.862 (5) | O01B—C02B | 1.444 (7) |
O1B—C1B | 1.214 (5) | O01B—H01B | 0.82 |
O2B—C3B | 1.211 (5) | C02B—C03B | 1.478 (7) |
O3B—C5B | 1.201 (5) | C02B—H02C | 0.97 |
C1B—N2B | 1.360 (5) | C02B—H02D | 0.97 |
C1B—C6B | 1.528 (6) | C03B—H03E | 0.96 |
N2B—C3B | 1.378 (6) | C03B—H03D | 0.96 |
N2B—H2B | 0.86 | C03B—H03F | 0.96 |
| | | |
O1A—C1A—N2A | 122.5 (4) | O3B—C5B—C6B | 121.8 (4) |
O1A—C1A—C6A | 122.8 (4) | N4B—C5B—C6B | 115.7 (4) |
N2A—C1A—C6A | 114.6 (4) | N7B—C6B—C1B | 110.6 (3) |
C3A—N2A—C1A | 126.9 (4) | N7B—C6B—C5B | 110.8 (3) |
C3A—N2A—H2A | 116.5 | C1B—C6B—C5B | 114.2 (3) |
C1A—N2A—H2A | 116.5 | N7B—C6B—C10B | 102.1 (3) |
O2A—C3A—N2A | 122.4 (4) | C1B—C6B—C10B | 107.8 (3) |
O2A—C3A—N4A | 121.3 (5) | C5B—C6B—C10B | 110.7 (3) |
N2A—C3A—N4A | 116.2 (4) | N8B—N7B—C17B | 116.4 (4) |
C5A—N4A—C3A | 126.2 (4) | N8B—N7B—C6B | 111.9 (3) |
C5A—N4A—H4A | 116.9 | C17B—N7B—C6B | 122.7 (3) |
C3A—N4A—H4A | 116.9 | C9B—N8B—N7B | 108.5 (4) |
O3A—C5A—N4A | 122.8 (4) | N8B—C9B—C10B | 116.3 (4) |
O3A—C5A—C6A | 122.4 (4) | N8B—C9B—Br1B | 120.0 (4) |
N4A—C5A—C6A | 114.4 (4) | C10B—C9B—Br1B | 123.4 (4) |
N7A—C6A—C1A | 111.2 (4) | C11B—C10B—C9B | 116.0 (4) |
N7A—C6A—C5A | 111.9 (4) | C11B—C10B—C6B | 119.1 (4) |
C1A—C6A—C5A | 112.6 (4) | C9B—C10B—C6B | 98.5 (3) |
N7A—C6A—C10A | 103.1 (3) | C11B—C10B—H10B | 107.5 |
C1A—C6A—C10A | 111.1 (3) | C9B—C10B—H10B | 107.5 |
C5A—C6A—C10A | 106.4 (4) | C6B—C10B—H10B | 107.5 |
N8A—N7A—C17A | 120.6 (4) | C12B—C11B—C16B | 118.7 (5) |
N8A—N7A—C6A | 113.3 (4) | C12B—C11B—C10B | 118.6 (4) |
C17A—N7A—C6A | 125.9 (4) | C16B—C11B—C10B | 122.6 (4) |
C9A—N8A—N7A | 108.0 (4) | C13B—C12B—C11B | 120.1 (5) |
N8A—C9A—C10A | 117.0 (4) | C13B—C12B—H12B | 120 |
N8A—C9A—Br1A | 121.9 (4) | C11B—C12B—H12B | 120 |
C10A—C9A—Br1A | 121.1 (4) | C14B—C13B—C12B | 121.1 (5) |
C9A—C10A—C11A | 115.2 (4) | C14B—C13B—H13B | 119.5 |
C9A—C10A—C6A | 98.4 (3) | C12B—C13B—H13B | 119.5 |
C11A—C10A—C6A | 116.5 (4) | C13B—C14B—C15B | 119.3 (5) |
C9A—C10A—H10A | 108.7 | C13B—C14B—H14B | 120.3 |
C11A—C10A—H10A | 108.7 | C15B—C14B—H14B | 120.3 |
C6A—C10A—H10A | 108.7 | C16B—C15B—C14B | 120.0 (5) |
C12A—C11A—C16A | 118.4 (4) | C16B—C15B—H15B | 120 |
C12A—C11A—C10A | 121.9 (4) | C14B—C15B—H15B | 120 |
C16A—C11A—C10A | 119.7 (4) | C15B—C16B—C11B | 120.8 (5) |
C13A—C12A—C11A | 121.1 (5) | C15B—C16B—H16B | 119.6 |
C13A—C12A—H12A | 119.4 | C11B—C16B—H16B | 119.6 |
C11A—C12A—H12A | 119.4 | C22B—C17B—C18B | 119.1 (5) |
C14A—C13A—C12A | 119.9 (5) | C22B—C17B—N7B | 120.2 (4) |
C14A—C13A—H13A | 120.1 | C18B—C17B—N7B | 120.7 (4) |
C12A—C13A—H13A | 120.1 | C19B—C18B—C17B | 119.8 (5) |
C15A—C14A—C13A | 120.4 (5) | C19B—C18B—H18B | 120.1 |
C15A—C14A—H14A | 119.8 | C17B—C18B—H18B | 120.1 |
C13A—C14A—H14A | 119.8 | C20B—C19B—C18B | 121.4 (6) |
C14A—C15A—C16A | 120.3 (5) | C20B—C19B—H19B | 119.3 |
C14A—C15A—H15A | 119.9 | C18B—C19B—H19B | 119.3 |
C16A—C15A—H15A | 119.9 | C19B—C20B—C21B | 118.3 (6) |
C15A—C16A—C11A | 119.9 (5) | C19B—C20B—H20B | 120.8 |
C15A—C16A—H16A | 120 | C21B—C20B—H20B | 120.8 |
C11A—C16A—H16A | 120 | C22B—C21B—C20B | 120.9 (6) |
C18A—C17A—N7A | 120.5 (4) | C22B—C21B—H21B | 119.5 |
C18A—C17A—C22A | 118.9 (4) | C20B—C21B—H21B | 119.5 |
N7A—C17A—C22A | 120.6 (4) | C21B—C22B—C17B | 120.5 (5) |
C17A—C18A—C19A | 119.1 (5) | C21B—C22B—H22B | 119.7 |
C17A—C18A—H18A | 120.4 | C17B—C22B—H22B | 119.7 |
C19A—C18A—H18A | 120.4 | C02A—O01A—H01A | 109.5 |
C20A—C19A—C18A | 121.7 (5) | O01A—C02A—C03A | 110.8 (5) |
C20A—C19A—H19A | 119.2 | O01A—C02A—H02A | 109.5 |
C18A—C19A—H19A | 119.2 | C03A—C02A—H02A | 109.5 |
C19A—C20A—C21A | 119.4 (5) | O01A—C02A—H02B | 109.5 |
C19A—C20A—H20A | 120.3 | C03A—C02A—H02B | 109.5 |
C21A—C20A—H20A | 120.3 | H02A—C02A—H02B | 108.1 |
C20A—C21A—C22A | 120.6 (5) | C02A—C03A—H03A | 109.5 |
C20A—C21A—H21A | 119.7 | C02A—C03A—H03B | 109.5 |
C22A—C21A—H21A | 119.7 | H03A—C03A—H03B | 109.5 |
C21A—C22A—C17A | 120.3 (4) | C02A—C03A—H03C | 109.5 |
C21A—C22A—H22A | 119.9 | H03A—C03A—H03C | 109.5 |
C17A—C22A—H22A | 119.9 | H03B—C03A—H03C | 109.5 |
O1B—C1B—N2B | 121.1 (4) | C02B—O01B—H01B | 109.5 |
O1B—C1B—C6B | 121.7 (4) | O01B—C02B—C03B | 112.4 (5) |
N2B—C1B—C6B | 117.1 (4) | O01B—C02B—H02C | 109.1 |
C1B—N2B—C3B | 126.7 (4) | C03B—C02B—H02C | 109.1 |
C1B—N2B—H2B | 116.6 | O01B—C02B—H02D | 109.1 |
C3B—N2B—H2B | 116.6 | C03B—C02B—H02D | 109.1 |
O2B—C3B—N4B | 122.7 (5) | H02C—C02B—H02D | 107.9 |
O2B—C3B—N2B | 121.2 (5) | C02B—C03B—H03E | 109.5 |
N4B—C3B—N2B | 116.0 (4) | C02B—C03B—H03D | 109.5 |
C5B—N4B—C3B | 127.3 (4) | H03E—C03B—H03D | 109.5 |
C5B—N4B—H4B | 116.3 | C02B—C03B—H03F | 109.5 |
C3B—N4B—H4B | 116.3 | H03E—C03B—H03F | 109.5 |
O3B—C5B—N4B | 122.5 (4) | H03D—C03B—H03F | 109.5 |
| | | |
O1A—C1A—N2A—C3A | −169.4 (5) | O1B—C1B—N2B—C3B | 176.2 (4) |
C6A—C1A—N2A—C3A | 14.7 (6) | C6B—C1B—N2B—C3B | −7.7 (7) |
C1A—N2A—C3A—O2A | 179.1 (5) | C1B—N2B—C3B—O2B | −178.6 (5) |
C1A—N2A—C3A—N4A | 1.9 (7) | C1B—N2B—C3B—N4B | 0.7 (7) |
O2A—C3A—N4A—C5A | −176.7 (5) | O2B—C3B—N4B—C5B | 174.5 (5) |
N2A—C3A—N4A—C5A | 0.5 (7) | N2B—C3B—N4B—C5B | −4.8 (7) |
C3A—N4A—C5A—O3A | 167.5 (5) | C3B—N4B—C5B—O3B | −167.9 (5) |
C3A—N4A—C5A—C6A | −19.0 (7) | C3B—N4B—C5B—C6B | 14.9 (7) |
O1A—C1A—C6A—N7A | 26.4 (6) | O1B—C1B—C6B—N7B | −41.5 (5) |
N2A—C1A—C6A—N7A | −157.7 (4) | N2B—C1B—C6B—N7B | 142.5 (4) |
O1A—C1A—C6A—C5A | 153.0 (4) | O1B—C1B—C6B—C5B | −167.3 (4) |
N2A—C1A—C6A—C5A | −31.2 (5) | N2B—C1B—C6B—C5B | 16.7 (5) |
O1A—C1A—C6A—C10A | −87.8 (5) | O1B—C1B—C6B—C10B | 69.3 (5) |
N2A—C1A—C6A—C10A | 88.0 (4) | N2B—C1B—C6B—C10B | −106.7 (4) |
O3A—C5A—C6A—N7A | −27.1 (6) | O3B—C5B—C6B—N7B | 37.3 (6) |
N4A—C5A—C6A—N7A | 159.4 (4) | N4B—C5B—C6B—N7B | −145.4 (4) |
O3A—C5A—C6A—C1A | −153.3 (4) | O3B—C5B—C6B—C1B | 163.0 (4) |
N4A—C5A—C6A—C1A | 33.2 (5) | N4B—C5B—C6B—C1B | −19.7 (5) |
O3A—C5A—C6A—C10A | 84.8 (5) | O3B—C5B—C6B—C10B | −75.2 (5) |
N4A—C5A—C6A—C10A | −88.7 (4) | N4B—C5B—C6B—C10B | 102.1 (4) |
C1A—C6A—N7A—N8A | −123.3 (4) | C1B—C6B—N7B—N8B | 130.7 (4) |
C5A—C6A—N7A—N8A | 109.8 (4) | C5B—C6B—N7B—N8B | −101.7 (4) |
C10A—C6A—N7A—N8A | −4.2 (5) | C10B—C6B—N7B—N8B | 16.2 (4) |
C1A—C6A—N7A—C17A | 61.5 (6) | C1B—C6B—N7B—C17B | −83.6 (5) |
C5A—C6A—N7A—C17A | −65.5 (6) | C5B—C6B—N7B—C17B | 44.1 (5) |
C10A—C6A—N7A—C17A | −179.4 (4) | C10B—C6B—N7B—C17B | 162.0 (4) |
C17A—N7A—N8A—C9A | 178.7 (5) | C17B—N7B—N8B—C9B | −158.0 (4) |
C6A—N7A—N8A—C9A | 3.2 (6) | C6B—N7B—N8B—C9B | −9.9 (5) |
N7A—N8A—C9A—C10A | −0.7 (6) | N7B—N8B—C9B—C10B | −1.8 (6) |
N7A—N8A—C9A—Br1A | −179.9 (3) | N7B—N8B—C9B—Br1B | −175.9 (3) |
N8A—C9A—C10A—C11A | 122.8 (5) | N8B—C9B—C10B—C11B | 139.5 (4) |
Br1A—C9A—C10A—C11A | −57.9 (5) | Br1B—C9B—C10B—C11B | −46.6 (5) |
N8A—C9A—C10A—C6A | −1.8 (6) | N8B—C9B—C10B—C6B | 11.2 (5) |
Br1A—C9A—C10A—C6A | 177.5 (3) | Br1B—C9B—C10B—C6B | −174.8 (3) |
N7A—C6A—C10A—C9A | 3.3 (4) | N7B—C6B—C10B—C11B | −141.1 (4) |
C1A—C6A—C10A—C9A | 122.5 (4) | C1B—C6B—C10B—C11B | 102.4 (4) |
C5A—C6A—C10A—C9A | −114.6 (4) | C5B—C6B—C10B—C11B | −23.1 (5) |
N7A—C6A—C10A—C11A | −120.4 (4) | N7B—C6B—C10B—C9B | −14.9 (4) |
C1A—C6A—C10A—C11A | −1.1 (5) | C1B—C6B—C10B—C9B | −131.5 (4) |
C5A—C6A—C10A—C11A | 121.8 (4) | C5B—C6B—C10B—C9B | 103.0 (4) |
C9A—C10A—C11A—C12A | −35.4 (6) | C9B—C10B—C11B—C12B | 136.6 (5) |
C6A—C10A—C11A—C12A | 79.1 (5) | C6B—C10B—C11B—C12B | −106.1 (5) |
C9A—C10A—C11A—C16A | 145.4 (4) | C9B—C10B—C11B—C16B | −40.8 (6) |
C6A—C10A—C11A—C16A | −100.2 (5) | C6B—C10B—C11B—C16B | 76.5 (5) |
C16A—C11A—C12A—C13A | 0.6 (7) | C16B—C11B—C12B—C13B | 1.0 (8) |
C10A—C11A—C12A—C13A | −178.7 (5) | C10B—C11B—C12B—C13B | −176.5 (5) |
C11A—C12A—C13A—C14A | −0.1 (8) | C11B—C12B—C13B—C14B | −1.3 (9) |
C12A—C13A—C14A—C15A | −0.2 (9) | C12B—C13B—C14B—C15B | 0.7 (9) |
C13A—C14A—C15A—C16A | 0.0 (9) | C13B—C14B—C15B—C16B | 0.2 (8) |
C14A—C15A—C16A—C11A | 0.4 (8) | C14B—C15B—C16B—C11B | −0.5 (7) |
C12A—C11A—C16A—C15A | −0.7 (7) | C12B—C11B—C16B—C15B | −0.1 (7) |
C10A—C11A—C16A—C15A | 178.6 (4) | C10B—C11B—C16B—C15B | 177.2 (4) |
N8A—N7A—C17A—C18A | 7.8 (7) | N8B—N7B—C17B—C22B | 177.7 (4) |
C6A—N7A—C17A—C18A | −177.3 (4) | C6B—N7B—C17B—C22B | 33.3 (7) |
N8A—N7A—C17A—C22A | −173.1 (4) | N8B—N7B—C17B—C18B | −4.1 (7) |
C6A—N7A—C17A—C22A | 1.9 (7) | C6B—N7B—C17B—C18B | −148.4 (5) |
N7A—C17A—C18A—C19A | 179.2 (5) | C22B—C17B—C18B—C19B | −0.6 (8) |
C22A—C17A—C18A—C19A | 0.0 (7) | N7B—C17B—C18B—C19B | −178.9 (5) |
C17A—C18A—C19A—C20A | 0.9 (8) | C17B—C18B—C19B—C20B | −0.3 (10) |
C18A—C19A—C20A—C21A | −0.8 (8) | C18B—C19B—C20B—C21B | 0.6 (10) |
C19A—C20A—C21A—C22A | −0.1 (8) | C19B—C20B—C21B—C22B | −0.1 (10) |
C20A—C21A—C22A—C17A | 0.9 (7) | C20B—C21B—C22B—C17B | −0.7 (9) |
C18A—C17A—C22A—C21A | −0.9 (7) | C18B—C17B—C22B—C21B | 1.1 (8) |
N7A—C17A—C22A—C21A | 179.9 (4) | N7B—C17B—C22B—C21B | 179.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O01A | 0.86 | 1.99 | 2.833 (5) | 168 |
N2B—H2B···O01A | 0.86 | 2.02 | 2.850 (5) | 162 |
N4B—H4B···O01Bi | 0.86 | 1.97 | 2.818 (5) | 170 |
N4A—H4A···O1Bii | 0.86 | 1.97 | 2.821 (5) | 170 |
O01A—H01A···O01Bii | 0.82 | 2.00 | 2.812 (5) | 170 |
O01B—H01B···O3A | 0.82 | 2.07 | 2.879 (5) | 170 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z+1. |
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