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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032829/rz6025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032829/rz6025Isup2.hkl
Contains datablock I

CCDC reference: 262475

Key indicators

  • Single-crystal X-ray study
  • T = 571 K
  • Mean [sigma](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

Computing details top

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·C2H6OZ = 4
Mr = 459.3F(000) = 936
Triclinic, P1Dx = 1.495 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.027 (4) ÅCell parameters from 27 reflections
b = 13.380 (5) Åθ = 3.4–18.0°
c = 13.416 (3) ŵ = 2.05 mm1
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 scansθmax = 25.7°, θmin = 1.9°
Absorption correction: ψ scan
(North et al., 1968)
h = 141
Tmin = 0.484, Tmax = 0.584k = 1616
8832 measured reflectionsl = 1616
7668 independent reflections3 standard reflections every 197 reflections
4687 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H-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) = 0.141Δρmax = 1.10 e Å3
S = 1.02Δρmin = 0.79 e Å3
7668 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
526 parametersExtinction 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
xyzUiso*/Ueq
Br1A0.40708 (5)0.57424 (5)0.14171 (5)0.0853 (3)
O1A0.5322 (3)0.3198 (3)0.5256 (3)0.0588 (9)
O2A0.3321 (3)0.0351 (3)0.5499 (3)0.0756 (12)
O3A0.5342 (3)0.1859 (3)0.2471 (3)0.0559 (9)
C1A0.4907 (4)0.2661 (4)0.4821 (4)0.0388 (10)
N2A0.4254 (3)0.1821 (3)0.5351 (3)0.0410 (9)
H2A0.40540.17570.59960.049*
C3A0.3887 (4)0.1076 (4)0.4968 (4)0.0464 (12)
N4A0.4237 (3)0.1166 (3)0.3946 (3)0.0464 (10)
H4A0.40030.07010.36950.056*
C5A0.4918 (4)0.1920 (4)0.3295 (4)0.0408 (11)
C6A0.4998 (3)0.2906 (3)0.3626 (3)0.0384 (10)
N7A0.5994 (3)0.3497 (3)0.3161 (3)0.0514 (11)
N8A0.5776 (3)0.4442 (3)0.2402 (3)0.0534 (11)
C9A0.4724 (4)0.4557 (4)0.2355 (4)0.0532 (13)
C10A0.4020 (4)0.3684 (3)0.3087 (3)0.0405 (11)
H10A0.3620.33550.26630.049*
C11A0.3186 (3)0.4019 (3)0.3817 (3)0.0386 (10)
C12A0.3416 (4)0.4799 (4)0.4243 (4)0.0488 (12)
H12A0.40960.51390.40670.059*
C13A0.2657 (5)0.5079 (4)0.4923 (4)0.0601 (14)
H13A0.28240.56040.52040.072*
C14A0.1653 (5)0.4585 (5)0.5187 (4)0.0636 (15)
H14A0.1140.47740.56490.076*
C15A0.1400 (4)0.3816 (5)0.4775 (4)0.0613 (15)
H15A0.07160.34840.49580.074*
C16A0.2159 (4)0.3528 (4)0.4086 (4)0.0486 (12)
H16A0.19820.30070.38040.058*
C17A0.7087 (4)0.3153 (4)0.3370 (4)0.0403 (11)
C18A0.7972 (4)0.3811 (4)0.2907 (4)0.0509 (13)
H18A0.78440.44850.24450.061*
C19A0.9057 (4)0.3448 (5)0.3142 (5)0.0631 (15)
H19A0.9650.38920.28390.076*
C20A0.9270 (4)0.2458 (5)0.3805 (4)0.0594 (14)
H20A10.22280.39450.071*
C21A0.8398 (4)0.1804 (4)0.4264 (4)0.0520 (13)
H21A0.8540.11290.47160.062*
C22A0.7311 (4)0.2141 (4)0.4062 (4)0.0459 (12)
H22A0.67260.16950.43860.055*
Br1B1.08077 (5)0.08684 (5)0.63063 (5)0.0677 (2)
O1B0.6316 (3)0.0522 (3)0.6749 (3)0.0495 (8)
O2B0.5260 (3)0.1296 (3)0.9702 (3)0.0775 (12)
O3B0.8586 (3)0.0363 (3)0.9653 (3)0.0529 (9)
C1B0.6562 (4)0.0555 (3)0.7601 (4)0.0378 (10)
N2B0.5828 (3)0.0932 (3)0.8215 (3)0.0486 (10)
H2B0.52040.11810.79520.058*
C3B0.5981 (4)0.0958 (4)0.9216 (4)0.0484 (12)
N4B0.6983 (3)0.0571 (3)0.9620 (3)0.0454 (10)
H4B0.71040.06321.02220.055*
C5B0.7814 (4)0.0100 (4)0.9173 (3)0.0393 (10)
C6B0.7728 (3)0.0244 (3)0.7998 (3)0.0355 (10)
N7B0.8144 (3)0.0706 (3)0.7751 (3)0.0436 (9)
N8B0.9211 (3)0.0574 (3)0.7276 (3)0.0493 (10)
C9B0.9460 (4)0.0390 (4)0.7041 (4)0.0467 (12)
C10B0.8564 (4)0.1117 (4)0.7296 (3)0.0411 (11)
H10B0.82060.1490.6640.049*
C11B0.8956 (4)0.1937 (3)0.7737 (4)0.0405 (11)
C12B0.8530 (5)0.2954 (4)0.7360 (4)0.0597 (14)
H12B0.79820.3110.68730.072*
C13B0.8915 (5)0.3735 (4)0.7704 (5)0.0732 (17)
H13B0.86350.4420.74350.088*
C14B0.9703 (5)0.3521 (4)0.8434 (5)0.0662 (16)
H14B0.99510.40530.86670.079*
C15B1.0129 (4)0.2503 (4)0.8825 (4)0.0541 (13)
H15B1.06640.23490.93240.065*
C16B0.9760 (4)0.1722 (4)0.8475 (4)0.0471 (12)
H16B1.00530.10410.87360.056*
C17B0.7867 (4)0.1741 (4)0.8397 (4)0.0438 (11)
C18B0.8610 (5)0.2574 (4)0.8481 (4)0.0607 (14)
H18B0.93060.24580.81210.073*
C19B0.8317 (6)0.3578 (4)0.9099 (5)0.0781 (19)
H19B0.88190.41350.9150.094*
C20B0.7296 (6)0.3773 (5)0.9644 (5)0.0810 (19)
H20B0.71070.44521.00650.097*
C21B0.6556 (5)0.2935 (5)0.9549 (5)0.0702 (16)
H21B0.58610.30520.99110.084*
C22B0.6834 (4)0.1935 (4)0.8931 (4)0.0549 (13)
H22B0.63230.13820.8870.066*
O01A0.3614 (3)0.1293 (2)0.7526 (2)0.0471 (8)
H01A0.33420.07050.77180.071*
C02A0.2901 (5)0.1996 (5)0.7893 (6)0.083 (2)
H02A0.28110.17310.86560.125*
H02B0.21720.20290.76150.125*
C03A0.3359 (8)0.3041 (5)0.7568 (6)0.119 (3)
H03A0.28330.35170.77570.178*
H03B0.35120.32780.68180.178*
H03C0.40380.30240.79120.178*
O01B0.7108 (3)0.0800 (3)0.1625 (3)0.0558 (9)
H01B0.65580.1040.18720.084*
C02B0.8044 (5)0.1478 (5)0.1523 (5)0.0742 (17)
H02C0.86960.1180.12490.111*
H02D0.81990.15040.22140.111*
C03B0.7839 (6)0.2561 (5)0.0817 (5)0.090 (2)
H03E0.84830.29810.0770.135*
H03D0.72060.28670.10940.135*
H03F0.76970.25410.01280.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0654 (4)0.0705 (4)0.0848 (5)0.0068 (3)0.0051 (3)0.0217 (3)
O1A0.060 (2)0.063 (2)0.066 (2)0.0099 (19)0.0121 (18)0.035 (2)
O2A0.085 (3)0.067 (3)0.073 (3)0.038 (2)0.028 (2)0.023 (2)
O3A0.054 (2)0.073 (2)0.0438 (19)0.0048 (18)0.0096 (16)0.0251 (18)
C1A0.032 (2)0.040 (3)0.045 (3)0.001 (2)0.004 (2)0.014 (2)
N2A0.044 (2)0.048 (2)0.033 (2)0.0062 (18)0.0035 (17)0.0157 (18)
C3A0.045 (3)0.045 (3)0.050 (3)0.009 (2)0.009 (2)0.017 (2)
N4A0.052 (2)0.045 (2)0.049 (2)0.0151 (19)0.0084 (19)0.0253 (19)
C5A0.034 (2)0.045 (3)0.045 (3)0.000 (2)0.002 (2)0.017 (2)
C6A0.030 (2)0.038 (3)0.045 (3)0.0055 (19)0.0040 (19)0.012 (2)
N7A0.031 (2)0.046 (2)0.066 (3)0.0067 (18)0.0048 (19)0.002 (2)
N8A0.042 (2)0.046 (2)0.061 (3)0.0015 (19)0.007 (2)0.002 (2)
C9A0.048 (3)0.047 (3)0.051 (3)0.001 (2)0.007 (2)0.002 (2)
C10A0.034 (2)0.041 (3)0.046 (3)0.002 (2)0.000 (2)0.013 (2)
C11A0.032 (2)0.036 (2)0.045 (3)0.0007 (19)0.002 (2)0.010 (2)
C12A0.042 (3)0.046 (3)0.060 (3)0.006 (2)0.000 (2)0.020 (2)
C13A0.063 (4)0.057 (3)0.068 (4)0.006 (3)0.005 (3)0.032 (3)
C14A0.053 (3)0.073 (4)0.067 (4)0.010 (3)0.010 (3)0.030 (3)
C15A0.035 (3)0.074 (4)0.073 (4)0.003 (3)0.014 (3)0.023 (3)
C16A0.037 (3)0.044 (3)0.064 (3)0.008 (2)0.002 (2)0.017 (2)
C17A0.031 (2)0.046 (3)0.048 (3)0.004 (2)0.005 (2)0.021 (2)
C18A0.042 (3)0.050 (3)0.060 (3)0.010 (2)0.008 (2)0.019 (3)
C19A0.037 (3)0.075 (4)0.079 (4)0.018 (3)0.015 (3)0.028 (3)
C20A0.037 (3)0.075 (4)0.071 (4)0.001 (3)0.000 (3)0.032 (3)
C21A0.049 (3)0.059 (3)0.054 (3)0.004 (3)0.006 (2)0.027 (3)
C22A0.037 (3)0.051 (3)0.053 (3)0.009 (2)0.000 (2)0.020 (2)
Br1B0.0465 (3)0.0830 (4)0.0679 (4)0.0114 (3)0.0205 (3)0.0197 (3)
O1B0.053 (2)0.056 (2)0.047 (2)0.0014 (16)0.0110 (16)0.0258 (17)
O2B0.062 (2)0.112 (3)0.065 (2)0.029 (2)0.006 (2)0.043 (2)
O3B0.046 (2)0.060 (2)0.047 (2)0.0061 (17)0.0134 (16)0.0073 (16)
C1B0.037 (2)0.037 (2)0.041 (3)0.001 (2)0.002 (2)0.014 (2)
N2B0.034 (2)0.069 (3)0.045 (2)0.010 (2)0.0052 (18)0.022 (2)
C3B0.045 (3)0.059 (3)0.044 (3)0.007 (2)0.003 (2)0.021 (2)
N4B0.043 (2)0.063 (3)0.034 (2)0.004 (2)0.0034 (18)0.0212 (19)
C5B0.034 (2)0.042 (3)0.040 (3)0.005 (2)0.001 (2)0.010 (2)
C6B0.033 (2)0.039 (2)0.034 (2)0.0013 (19)0.0001 (19)0.0114 (19)
N7B0.041 (2)0.042 (2)0.048 (2)0.0003 (18)0.0114 (18)0.0170 (18)
N8B0.040 (2)0.055 (3)0.052 (2)0.002 (2)0.0116 (19)0.019 (2)
C9B0.037 (3)0.056 (3)0.044 (3)0.000 (2)0.007 (2)0.014 (2)
C10B0.036 (2)0.046 (3)0.037 (2)0.002 (2)0.002 (2)0.009 (2)
C11B0.034 (2)0.039 (3)0.046 (3)0.001 (2)0.003 (2)0.010 (2)
C12B0.060 (3)0.044 (3)0.069 (4)0.007 (3)0.015 (3)0.009 (3)
C13B0.075 (4)0.034 (3)0.102 (5)0.001 (3)0.007 (4)0.010 (3)
C14B0.066 (4)0.055 (4)0.085 (4)0.010 (3)0.005 (3)0.034 (3)
C15B0.047 (3)0.057 (3)0.064 (3)0.006 (3)0.004 (3)0.027 (3)
C16B0.039 (3)0.045 (3)0.055 (3)0.004 (2)0.004 (2)0.014 (2)
C17B0.043 (3)0.045 (3)0.044 (3)0.001 (2)0.003 (2)0.017 (2)
C18B0.058 (3)0.052 (3)0.070 (4)0.002 (3)0.011 (3)0.019 (3)
C19B0.092 (5)0.044 (3)0.090 (5)0.017 (3)0.000 (4)0.014 (3)
C20B0.114 (6)0.051 (4)0.071 (4)0.011 (4)0.003 (4)0.010 (3)
C21B0.080 (4)0.060 (4)0.065 (4)0.019 (3)0.014 (3)0.014 (3)
C22B0.049 (3)0.050 (3)0.062 (3)0.001 (2)0.007 (3)0.015 (3)
O01A0.0435 (18)0.052 (2)0.0453 (18)0.0014 (15)0.0032 (15)0.0152 (15)
C02A0.057 (4)0.082 (5)0.121 (6)0.002 (3)0.019 (4)0.052 (4)
C03A0.184 (9)0.065 (5)0.107 (6)0.008 (5)0.011 (6)0.032 (4)
O01B0.060 (2)0.060 (2)0.049 (2)0.0059 (18)0.0019 (17)0.0219 (17)
C02B0.065 (4)0.103 (5)0.066 (4)0.004 (4)0.007 (3)0.043 (4)
C03B0.106 (6)0.086 (5)0.078 (5)0.025 (4)0.015 (4)0.029 (4)
Geometric parameters (Å, º) top
Br1A—C9A1.864 (5)C3B—N4B1.369 (6)
O1A—C1A1.201 (5)N4B—C5B1.368 (6)
O2A—C3A1.206 (5)N4B—H4B0.86
O3A—C5A1.211 (5)C5B—C6B1.536 (6)
C1A—N2A1.366 (5)C6B—N7B1.474 (5)
C1A—C6A1.527 (6)C6B—C10B1.587 (6)
N2A—C3A1.357 (6)N7B—N8B1.385 (5)
N2A—H2A0.86N7B—C17B1.417 (6)
C3A—N4A1.376 (6)N8B—C9B1.269 (6)
N4A—C5A1.362 (6)C9B—C10B1.520 (6)
N4A—H4A0.86C10B—C11B1.507 (6)
C5A—C6A1.530 (6)C10B—H10B0.98
C6A—N7A1.451 (5)C11B—C12B1.382 (6)
C6A—C10A1.590 (6)C11B—C16B1.386 (6)
N7A—N8A1.374 (5)C12B—C13B1.377 (8)
N7A—C17A1.392 (6)C12B—H12B0.93
N8A—C9A1.273 (6)C13B—C14B1.365 (8)
C9A—C10A1.508 (6)C13B—H13B0.93
C10A—C11A1.511 (6)C14B—C15B1.385 (7)
C10A—H10A0.98C14B—H14B0.93
C11A—C12A1.385 (6)C15B—C16B1.374 (7)
C11A—C16A1.392 (6)C15B—H15B0.93
C12A—C13A1.374 (7)C16B—H16B0.93
C12A—H12A0.93C17B—C22B1.382 (6)
C13A—C14A1.369 (7)C17B—C18B1.384 (7)
C13A—H13A0.93C18B—C19B1.378 (8)
C14A—C15A1.366 (7)C18B—H18B0.93
C14A—H14A0.93C19B—C20B1.376 (9)
C15A—C16A1.388 (7)C19B—H19B0.93
C15A—H15A0.93C20B—C21B1.384 (8)
C16A—H16A0.93C20B—H20B0.93
C17A—C18A1.388 (6)C21B—C22B1.369 (7)
C17A—C22A1.403 (6)C21B—H21B0.93
C18A—C19A1.395 (7)C22B—H22B0.93
C18A—H18A0.93O01A—C02A1.429 (6)
C19A—C20A1.365 (8)O01A—H01A0.82
C19A—H19A0.93C02A—C03A1.444 (7)
C20A—C21A1.371 (7)C02A—H02A0.97
C20A—H20A0.93C02A—H02B0.97
C21A—C22A1.382 (6)C03A—H03A0.96
C21A—H21A0.93C03A—H03B0.96
C22A—H22A0.93C03A—H03C0.96
Br1B—C9B1.862 (5)O01B—C02B1.444 (7)
O1B—C1B1.214 (5)O01B—H01B0.82
O2B—C3B1.211 (5)C02B—C03B1.478 (7)
O3B—C5B1.201 (5)C02B—H02C0.97
C1B—N2B1.360 (5)C02B—H02D0.97
C1B—C6B1.528 (6)C03B—H03E0.96
N2B—C3B1.378 (6)C03B—H03D0.96
N2B—H2B0.86C03B—H03F0.96
O1A—C1A—N2A122.5 (4)O3B—C5B—C6B121.8 (4)
O1A—C1A—C6A122.8 (4)N4B—C5B—C6B115.7 (4)
N2A—C1A—C6A114.6 (4)N7B—C6B—C1B110.6 (3)
C3A—N2A—C1A126.9 (4)N7B—C6B—C5B110.8 (3)
C3A—N2A—H2A116.5C1B—C6B—C5B114.2 (3)
C1A—N2A—H2A116.5N7B—C6B—C10B102.1 (3)
O2A—C3A—N2A122.4 (4)C1B—C6B—C10B107.8 (3)
O2A—C3A—N4A121.3 (5)C5B—C6B—C10B110.7 (3)
N2A—C3A—N4A116.2 (4)N8B—N7B—C17B116.4 (4)
C5A—N4A—C3A126.2 (4)N8B—N7B—C6B111.9 (3)
C5A—N4A—H4A116.9C17B—N7B—C6B122.7 (3)
C3A—N4A—H4A116.9C9B—N8B—N7B108.5 (4)
O3A—C5A—N4A122.8 (4)N8B—C9B—C10B116.3 (4)
O3A—C5A—C6A122.4 (4)N8B—C9B—Br1B120.0 (4)
N4A—C5A—C6A114.4 (4)C10B—C9B—Br1B123.4 (4)
N7A—C6A—C1A111.2 (4)C11B—C10B—C9B116.0 (4)
N7A—C6A—C5A111.9 (4)C11B—C10B—C6B119.1 (4)
C1A—C6A—C5A112.6 (4)C9B—C10B—C6B98.5 (3)
N7A—C6A—C10A103.1 (3)C11B—C10B—H10B107.5
C1A—C6A—C10A111.1 (3)C9B—C10B—H10B107.5
C5A—C6A—C10A106.4 (4)C6B—C10B—H10B107.5
N8A—N7A—C17A120.6 (4)C12B—C11B—C16B118.7 (5)
N8A—N7A—C6A113.3 (4)C12B—C11B—C10B118.6 (4)
C17A—N7A—C6A125.9 (4)C16B—C11B—C10B122.6 (4)
C9A—N8A—N7A108.0 (4)C13B—C12B—C11B120.1 (5)
N8A—C9A—C10A117.0 (4)C13B—C12B—H12B120
N8A—C9A—Br1A121.9 (4)C11B—C12B—H12B120
C10A—C9A—Br1A121.1 (4)C14B—C13B—C12B121.1 (5)
C9A—C10A—C11A115.2 (4)C14B—C13B—H13B119.5
C9A—C10A—C6A98.4 (3)C12B—C13B—H13B119.5
C11A—C10A—C6A116.5 (4)C13B—C14B—C15B119.3 (5)
C9A—C10A—H10A108.7C13B—C14B—H14B120.3
C11A—C10A—H10A108.7C15B—C14B—H14B120.3
C6A—C10A—H10A108.7C16B—C15B—C14B120.0 (5)
C12A—C11A—C16A118.4 (4)C16B—C15B—H15B120
C12A—C11A—C10A121.9 (4)C14B—C15B—H15B120
C16A—C11A—C10A119.7 (4)C15B—C16B—C11B120.8 (5)
C13A—C12A—C11A121.1 (5)C15B—C16B—H16B119.6
C13A—C12A—H12A119.4C11B—C16B—H16B119.6
C11A—C12A—H12A119.4C22B—C17B—C18B119.1 (5)
C14A—C13A—C12A119.9 (5)C22B—C17B—N7B120.2 (4)
C14A—C13A—H13A120.1C18B—C17B—N7B120.7 (4)
C12A—C13A—H13A120.1C19B—C18B—C17B119.8 (5)
C15A—C14A—C13A120.4 (5)C19B—C18B—H18B120.1
C15A—C14A—H14A119.8C17B—C18B—H18B120.1
C13A—C14A—H14A119.8C20B—C19B—C18B121.4 (6)
C14A—C15A—C16A120.3 (5)C20B—C19B—H19B119.3
C14A—C15A—H15A119.9C18B—C19B—H19B119.3
C16A—C15A—H15A119.9C19B—C20B—C21B118.3 (6)
C15A—C16A—C11A119.9 (5)C19B—C20B—H20B120.8
C15A—C16A—H16A120C21B—C20B—H20B120.8
C11A—C16A—H16A120C22B—C21B—C20B120.9 (6)
C18A—C17A—N7A120.5 (4)C22B—C21B—H21B119.5
C18A—C17A—C22A118.9 (4)C20B—C21B—H21B119.5
N7A—C17A—C22A120.6 (4)C21B—C22B—C17B120.5 (5)
C17A—C18A—C19A119.1 (5)C21B—C22B—H22B119.7
C17A—C18A—H18A120.4C17B—C22B—H22B119.7
C19A—C18A—H18A120.4C02A—O01A—H01A109.5
C20A—C19A—C18A121.7 (5)O01A—C02A—C03A110.8 (5)
C20A—C19A—H19A119.2O01A—C02A—H02A109.5
C18A—C19A—H19A119.2C03A—C02A—H02A109.5
C19A—C20A—C21A119.4 (5)O01A—C02A—H02B109.5
C19A—C20A—H20A120.3C03A—C02A—H02B109.5
C21A—C20A—H20A120.3H02A—C02A—H02B108.1
C20A—C21A—C22A120.6 (5)C02A—C03A—H03A109.5
C20A—C21A—H21A119.7C02A—C03A—H03B109.5
C22A—C21A—H21A119.7H03A—C03A—H03B109.5
C21A—C22A—C17A120.3 (4)C02A—C03A—H03C109.5
C21A—C22A—H22A119.9H03A—C03A—H03C109.5
C17A—C22A—H22A119.9H03B—C03A—H03C109.5
O1B—C1B—N2B121.1 (4)C02B—O01B—H01B109.5
O1B—C1B—C6B121.7 (4)O01B—C02B—C03B112.4 (5)
N2B—C1B—C6B117.1 (4)O01B—C02B—H02C109.1
C1B—N2B—C3B126.7 (4)C03B—C02B—H02C109.1
C1B—N2B—H2B116.6O01B—C02B—H02D109.1
C3B—N2B—H2B116.6C03B—C02B—H02D109.1
O2B—C3B—N4B122.7 (5)H02C—C02B—H02D107.9
O2B—C3B—N2B121.2 (5)C02B—C03B—H03E109.5
N4B—C3B—N2B116.0 (4)C02B—C03B—H03D109.5
C5B—N4B—C3B127.3 (4)H03E—C03B—H03D109.5
C5B—N4B—H4B116.3C02B—C03B—H03F109.5
C3B—N4B—H4B116.3H03E—C03B—H03F109.5
O3B—C5B—N4B122.5 (4)H03D—C03B—H03F109.5
O1A—C1A—N2A—C3A169.4 (5)O1B—C1B—N2B—C3B176.2 (4)
C6A—C1A—N2A—C3A14.7 (6)C6B—C1B—N2B—C3B7.7 (7)
C1A—N2A—C3A—O2A179.1 (5)C1B—N2B—C3B—O2B178.6 (5)
C1A—N2A—C3A—N4A1.9 (7)C1B—N2B—C3B—N4B0.7 (7)
O2A—C3A—N4A—C5A176.7 (5)O2B—C3B—N4B—C5B174.5 (5)
N2A—C3A—N4A—C5A0.5 (7)N2B—C3B—N4B—C5B4.8 (7)
C3A—N4A—C5A—O3A167.5 (5)C3B—N4B—C5B—O3B167.9 (5)
C3A—N4A—C5A—C6A19.0 (7)C3B—N4B—C5B—C6B14.9 (7)
O1A—C1A—C6A—N7A26.4 (6)O1B—C1B—C6B—N7B41.5 (5)
N2A—C1A—C6A—N7A157.7 (4)N2B—C1B—C6B—N7B142.5 (4)
O1A—C1A—C6A—C5A153.0 (4)O1B—C1B—C6B—C5B167.3 (4)
N2A—C1A—C6A—C5A31.2 (5)N2B—C1B—C6B—C5B16.7 (5)
O1A—C1A—C6A—C10A87.8 (5)O1B—C1B—C6B—C10B69.3 (5)
N2A—C1A—C6A—C10A88.0 (4)N2B—C1B—C6B—C10B106.7 (4)
O3A—C5A—C6A—N7A27.1 (6)O3B—C5B—C6B—N7B37.3 (6)
N4A—C5A—C6A—N7A159.4 (4)N4B—C5B—C6B—N7B145.4 (4)
O3A—C5A—C6A—C1A153.3 (4)O3B—C5B—C6B—C1B163.0 (4)
N4A—C5A—C6A—C1A33.2 (5)N4B—C5B—C6B—C1B19.7 (5)
O3A—C5A—C6A—C10A84.8 (5)O3B—C5B—C6B—C10B75.2 (5)
N4A—C5A—C6A—C10A88.7 (4)N4B—C5B—C6B—C10B102.1 (4)
C1A—C6A—N7A—N8A123.3 (4)C1B—C6B—N7B—N8B130.7 (4)
C5A—C6A—N7A—N8A109.8 (4)C5B—C6B—N7B—N8B101.7 (4)
C10A—C6A—N7A—N8A4.2 (5)C10B—C6B—N7B—N8B16.2 (4)
C1A—C6A—N7A—C17A61.5 (6)C1B—C6B—N7B—C17B83.6 (5)
C5A—C6A—N7A—C17A65.5 (6)C5B—C6B—N7B—C17B44.1 (5)
C10A—C6A—N7A—C17A179.4 (4)C10B—C6B—N7B—C17B162.0 (4)
C17A—N7A—N8A—C9A178.7 (5)C17B—N7B—N8B—C9B158.0 (4)
C6A—N7A—N8A—C9A3.2 (6)C6B—N7B—N8B—C9B9.9 (5)
N7A—N8A—C9A—C10A0.7 (6)N7B—N8B—C9B—C10B1.8 (6)
N7A—N8A—C9A—Br1A179.9 (3)N7B—N8B—C9B—Br1B175.9 (3)
N8A—C9A—C10A—C11A122.8 (5)N8B—C9B—C10B—C11B139.5 (4)
Br1A—C9A—C10A—C11A57.9 (5)Br1B—C9B—C10B—C11B46.6 (5)
N8A—C9A—C10A—C6A1.8 (6)N8B—C9B—C10B—C6B11.2 (5)
Br1A—C9A—C10A—C6A177.5 (3)Br1B—C9B—C10B—C6B174.8 (3)
N7A—C6A—C10A—C9A3.3 (4)N7B—C6B—C10B—C11B141.1 (4)
C1A—C6A—C10A—C9A122.5 (4)C1B—C6B—C10B—C11B102.4 (4)
C5A—C6A—C10A—C9A114.6 (4)C5B—C6B—C10B—C11B23.1 (5)
N7A—C6A—C10A—C11A120.4 (4)N7B—C6B—C10B—C9B14.9 (4)
C1A—C6A—C10A—C11A1.1 (5)C1B—C6B—C10B—C9B131.5 (4)
C5A—C6A—C10A—C11A121.8 (4)C5B—C6B—C10B—C9B103.0 (4)
C9A—C10A—C11A—C12A35.4 (6)C9B—C10B—C11B—C12B136.6 (5)
C6A—C10A—C11A—C12A79.1 (5)C6B—C10B—C11B—C12B106.1 (5)
C9A—C10A—C11A—C16A145.4 (4)C9B—C10B—C11B—C16B40.8 (6)
C6A—C10A—C11A—C16A100.2 (5)C6B—C10B—C11B—C16B76.5 (5)
C16A—C11A—C12A—C13A0.6 (7)C16B—C11B—C12B—C13B1.0 (8)
C10A—C11A—C12A—C13A178.7 (5)C10B—C11B—C12B—C13B176.5 (5)
C11A—C12A—C13A—C14A0.1 (8)C11B—C12B—C13B—C14B1.3 (9)
C12A—C13A—C14A—C15A0.2 (9)C12B—C13B—C14B—C15B0.7 (9)
C13A—C14A—C15A—C16A0.0 (9)C13B—C14B—C15B—C16B0.2 (8)
C14A—C15A—C16A—C11A0.4 (8)C14B—C15B—C16B—C11B0.5 (7)
C12A—C11A—C16A—C15A0.7 (7)C12B—C11B—C16B—C15B0.1 (7)
C10A—C11A—C16A—C15A178.6 (4)C10B—C11B—C16B—C15B177.2 (4)
N8A—N7A—C17A—C18A7.8 (7)N8B—N7B—C17B—C22B177.7 (4)
C6A—N7A—C17A—C18A177.3 (4)C6B—N7B—C17B—C22B33.3 (7)
N8A—N7A—C17A—C22A173.1 (4)N8B—N7B—C17B—C18B4.1 (7)
C6A—N7A—C17A—C22A1.9 (7)C6B—N7B—C17B—C18B148.4 (5)
N7A—C17A—C18A—C19A179.2 (5)C22B—C17B—C18B—C19B0.6 (8)
C22A—C17A—C18A—C19A0.0 (7)N7B—C17B—C18B—C19B178.9 (5)
C17A—C18A—C19A—C20A0.9 (8)C17B—C18B—C19B—C20B0.3 (10)
C18A—C19A—C20A—C21A0.8 (8)C18B—C19B—C20B—C21B0.6 (10)
C19A—C20A—C21A—C22A0.1 (8)C19B—C20B—C21B—C22B0.1 (10)
C20A—C21A—C22A—C17A0.9 (7)C20B—C21B—C22B—C17B0.7 (9)
C18A—C17A—C22A—C21A0.9 (7)C18B—C17B—C22B—C21B1.1 (8)
N7A—C17A—C22A—C21A179.9 (4)N7B—C17B—C22B—C21B179.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O01A0.861.992.833 (5)168
N2B—H2B···O01A0.862.022.850 (5)162
N4B—H4B···O01Bi0.861.972.818 (5)170
N4A—H4A···O1Bii0.861.972.821 (5)170
O01A—H01A···O01Bii0.822.002.812 (5)170
O01B—H01B···O3A0.822.072.879 (5)170
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.
 

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