Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014029/ci6572sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014029/ci6572Isup2.hkl |
CCDC reference: 274361
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.009 Å
- R factor = 0.079
- wR factor = 0.157
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT731_ALERT_1_B Bond Calc 0.88(6), Rep 0.881(10) ...... 6.00 su-Rat N4 -H4 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.88(6), Rep 0.880(10) ...... 6.00 su-Rat N4 -H4 1.555 1.555
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for Br3 - C54 .. 6.05 su PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT731_ALERT_1_C Bond Calc 0.89(3), Rep 0.883(10) ...... 3.00 su-Rat N1 -H1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.88(4), Rep 0.877(10) ...... 4.00 su-Rat N7 -H7 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(3), Rep 0.880(10) ...... 3.00 su-Rat N1 -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(4), Rep 0.880(10) ...... 4.00 su-Rat N7 -H7 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.93(4), Rep 1.940(10) ...... 4.00 su-Rat H1 -O1 1.555 3.766 PLAT736_ALERT_1_C H...A Calc 1.94(5), Rep 1.94(2) ...... 2.50 su-Rat H4 -O3 1.555 4.575 PLAT736_ALERT_1_C H...A Calc 1.96(4), Rep 1.960(10) ...... 4.00 su-Rat H7 -O2 1.555 4.576
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 9 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C19H16BrN3O | F(000) = 2328 |
Mr = 382.26 | Dx = 1.515 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2ybc | Cell parameters from 19389 reflections |
a = 13.905 (2) Å | θ = 3.0–25.3° |
b = 17.965 (3) Å | µ = 2.46 mm−1 |
c = 20.505 (4) Å | T = 193 K |
β = 101.026 (7)° | Block, colourless |
V = 5027.5 (15) Å3 | 0.60 × 0.40 × 0.39 mm |
Z = 12 |
Rigaku Mercury CCD area-detector diffractometer | 9180 independent reflections |
Radiation source: fine-focus sealed tube | 7942 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.0° |
ω scans | h = −16→16 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −20→21 |
Tmin = 0.274, Tmax = 0.383 | l = −24→24 |
48280 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0145P)2 + 35.9447P] where P = (Fo2 + 2Fc2)/3 |
9180 reflections | (Δ/σ)max = 0.001 |
665 parameters | Δρmax = 1.91 e Å−3 |
3 restraints | Δρmin = −0.98 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 1.06779 (6) | 0.63714 (4) | 0.01764 (3) | 0.0472 (2) | |
Br2 | 0.57949 (6) | 0.37851 (4) | 0.62983 (4) | 0.0537 (2) | |
Br3 | 0.77044 (7) | 0.85290 (4) | 0.17049 (4) | 0.0604 (2) | |
O1 | 1.0878 (3) | 0.4738 (2) | 0.4544 (2) | 0.0418 (11) | |
O2 | 0.5680 (3) | 0.5191 (2) | 0.1881 (2) | 0.0412 (11) | |
O3 | 0.7373 (3) | 1.0364 (2) | 0.5937 (2) | 0.0396 (10) | |
N1 | 0.9619 (4) | 0.5535 (3) | 0.4211 (2) | 0.0317 (11) | |
N2 | 0.7820 (4) | 0.6559 (3) | 0.3073 (2) | 0.0342 (12) | |
N3 | 0.8284 (3) | 0.6368 (3) | 0.3705 (2) | 0.0299 (11) | |
N4 | 0.6955 (4) | 0.4417 (3) | 0.2212 (2) | 0.0312 (11) | |
N5 | 0.8713 (4) | 0.3327 (3) | 0.3331 (2) | 0.0334 (11) | |
N6 | 0.8250 (3) | 0.3544 (3) | 0.2699 (2) | 0.0290 (10) | |
N7 | 0.6141 (4) | 0.9547 (3) | 0.5612 (2) | 0.0293 (11) | |
N8 | 0.4608 (3) | 0.8266 (3) | 0.4542 (2) | 0.0298 (11) | |
N9 | 0.4943 (3) | 0.8596 (3) | 0.5147 (2) | 0.0271 (10) | |
C1 | 0.9025 (4) | 0.5881 (3) | 0.3670 (3) | 0.0285 (12) | |
C2 | 0.9060 (4) | 0.5754 (3) | 0.3029 (3) | 0.0305 (13) | |
C3 | 0.9813 (5) | 0.5241 (3) | 0.2842 (3) | 0.0350 (14) | |
H3 | 0.9526 | 0.4729 | 0.2776 | 0.042* | |
C4 | 1.0680 (5) | 0.5223 (4) | 0.3436 (3) | 0.0388 (15) | |
H4A | 1.1122 | 0.4809 | 0.3369 | 0.047* | |
H4B | 1.1054 | 0.5692 | 0.3439 | 0.047* | |
C5 | 1.0402 (4) | 0.5129 (3) | 0.4099 (3) | 0.0351 (14) | |
C6 | 0.8288 (4) | 0.6195 (3) | 0.2664 (3) | 0.0337 (13) | |
C7 | 0.8014 (4) | 0.6729 (3) | 0.4249 (3) | 0.0311 (13) | |
C8 | 0.8707 (5) | 0.6979 (4) | 0.4773 (3) | 0.0405 (15) | |
H8 | 0.9383 | 0.6899 | 0.4776 | 0.049* | |
C9 | 0.8422 (6) | 0.7348 (4) | 0.5294 (3) | 0.0502 (18) | |
H9 | 0.8902 | 0.7517 | 0.5658 | 0.060* | |
C10 | 0.7448 (6) | 0.7471 (4) | 0.5289 (4) | 0.055 (2) | |
H10 | 0.7251 | 0.7733 | 0.5644 | 0.067* | |
C11 | 0.6761 (5) | 0.7215 (4) | 0.4768 (4) | 0.051 (2) | |
H11 | 0.6087 | 0.7299 | 0.4768 | 0.062* | |
C12 | 0.7021 (5) | 0.6843 (3) | 0.4252 (4) | 0.0406 (16) | |
H12 | 0.6534 | 0.6663 | 0.3897 | 0.049* | |
C13 | 1.0123 (5) | 0.5480 (3) | 0.2209 (3) | 0.0345 (14) | |
C14 | 1.0491 (5) | 0.6190 (3) | 0.2154 (3) | 0.0366 (14) | |
H14 | 1.0619 | 0.6503 | 0.2535 | 0.044* | |
C15 | 1.0675 (5) | 0.6453 (3) | 0.1554 (3) | 0.0372 (14) | |
H15 | 1.0926 | 0.6940 | 0.1521 | 0.045* | |
C16 | 1.0488 (5) | 0.6000 (3) | 0.1010 (3) | 0.0348 (14) | |
C17 | 1.0153 (6) | 0.5280 (4) | 0.1050 (3) | 0.0509 (19) | |
H17 | 1.0055 | 0.4963 | 0.0672 | 0.061* | |
C18 | 0.9965 (6) | 0.5033 (4) | 0.1649 (3) | 0.0491 (18) | |
H18 | 0.9721 | 0.4543 | 0.1678 | 0.059* | |
C19 | 0.7974 (5) | 0.6289 (4) | 0.1937 (3) | 0.0448 (16) | |
H19A | 0.7375 | 0.6589 | 0.1845 | 0.067* | |
H19B | 0.7847 | 0.5800 | 0.1727 | 0.067* | |
H19C | 0.8492 | 0.6541 | 0.1758 | 0.067* | |
C20 | 0.7534 (4) | 0.4040 (3) | 0.2745 (3) | 0.0262 (12) | |
C21 | 0.7499 (4) | 0.4156 (3) | 0.3397 (3) | 0.0308 (13) | |
C22 | 0.6783 (4) | 0.4698 (3) | 0.3588 (3) | 0.0331 (13) | |
H22 | 0.7107 | 0.5197 | 0.3646 | 0.040* | |
C23 | 0.5915 (4) | 0.4750 (4) | 0.3002 (3) | 0.0370 (15) | |
H23A | 0.5504 | 0.4300 | 0.3004 | 0.044* | |
H23B | 0.5511 | 0.5185 | 0.3074 | 0.044* | |
C24 | 0.6179 (4) | 0.4820 (3) | 0.2325 (3) | 0.0325 (13) | |
C25 | 0.8253 (4) | 0.3698 (3) | 0.3737 (3) | 0.0308 (13) | |
C26 | 0.8521 (4) | 0.3189 (3) | 0.2145 (3) | 0.0292 (13) | |
C27 | 0.9505 (5) | 0.3041 (3) | 0.2159 (3) | 0.0362 (14) | |
H27 | 0.9992 | 0.3200 | 0.2522 | 0.043* | |
C28 | 0.9759 (5) | 0.2655 (4) | 0.1631 (3) | 0.0421 (16) | |
H28 | 1.0429 | 0.2547 | 0.1634 | 0.050* | |
C29 | 0.9053 (5) | 0.2424 (4) | 0.1101 (3) | 0.0444 (17) | |
H29 | 0.9237 | 0.2152 | 0.0747 | 0.053* | |
C30 | 0.8086 (5) | 0.2589 (4) | 0.1086 (3) | 0.0447 (17) | |
H30 | 0.7601 | 0.2437 | 0.0719 | 0.054* | |
C31 | 0.7820 (5) | 0.2977 (4) | 0.1607 (3) | 0.0383 (15) | |
H31 | 0.7151 | 0.3098 | 0.1594 | 0.046* | |
C32 | 0.6474 (4) | 0.4495 (3) | 0.4238 (3) | 0.0308 (13) | |
C33 | 0.6677 (5) | 0.4960 (3) | 0.4782 (3) | 0.0411 (16) | |
H33 | 0.6971 | 0.5430 | 0.4737 | 0.049* | |
C34 | 0.6467 (5) | 0.4764 (4) | 0.5387 (3) | 0.0467 (17) | |
H34 | 0.6614 | 0.5095 | 0.5754 | 0.056* | |
C35 | 0.6044 (5) | 0.4087 (3) | 0.5457 (3) | 0.0376 (14) | |
C36 | 0.5820 (5) | 0.3608 (3) | 0.4925 (3) | 0.0416 (16) | |
H36 | 0.5523 | 0.3140 | 0.4972 | 0.050* | |
C37 | 0.6034 (5) | 0.3822 (3) | 0.4325 (3) | 0.0437 (16) | |
H37 | 0.5873 | 0.3495 | 0.3956 | 0.052* | |
C38 | 0.8567 (5) | 0.3578 (4) | 0.4465 (3) | 0.0468 (17) | |
H38A | 0.9138 | 0.3247 | 0.4547 | 0.070* | |
H38B | 0.8030 | 0.3351 | 0.4642 | 0.070* | |
H38C | 0.8740 | 0.4057 | 0.4684 | 0.070* | |
C39 | 0.5653 (4) | 0.9099 (3) | 0.5096 (3) | 0.0273 (12) | |
C40 | 0.5797 (4) | 0.9114 (3) | 0.4461 (3) | 0.0269 (12) | |
C41 | 0.6508 (4) | 0.9660 (3) | 0.4273 (3) | 0.0314 (13) | |
H41 | 0.6159 | 1.0145 | 0.4166 | 0.038* | |
C42 | 0.7324 (4) | 0.9779 (3) | 0.4882 (3) | 0.0346 (14) | |
H42A | 0.7744 | 0.9330 | 0.4947 | 0.042* | |
H42B | 0.7736 | 1.0202 | 0.4794 | 0.042* | |
C43 | 0.6951 (4) | 0.9932 (3) | 0.5516 (3) | 0.0317 (13) | |
C44 | 0.5136 (4) | 0.8575 (3) | 0.4138 (3) | 0.0297 (12) | |
C45 | 0.4559 (4) | 0.8357 (3) | 0.5713 (3) | 0.0306 (13) | |
C46 | 0.3566 (4) | 0.8283 (3) | 0.5663 (3) | 0.0353 (14) | |
H46 | 0.3134 | 0.8395 | 0.5257 | 0.042* | |
C47 | 0.3193 (5) | 0.8042 (4) | 0.6214 (4) | 0.0479 (18) | |
H47 | 0.2507 | 0.7979 | 0.6179 | 0.057* | |
C48 | 0.3811 (7) | 0.7899 (4) | 0.6799 (4) | 0.058 (2) | |
H48 | 0.3555 | 0.7749 | 0.7176 | 0.069* | |
C49 | 0.4811 (6) | 0.7970 (4) | 0.6845 (4) | 0.056 (2) | |
H49 | 0.5241 | 0.7858 | 0.7252 | 0.067* | |
C50 | 0.5192 (5) | 0.8203 (4) | 0.6300 (3) | 0.0469 (17) | |
H50 | 0.5879 | 0.8254 | 0.6332 | 0.056* | |
C51 | 0.6914 (4) | 0.9419 (3) | 0.3668 (3) | 0.0294 (13) | |
C52 | 0.6759 (5) | 0.9857 (3) | 0.3108 (3) | 0.0398 (15) | |
H52 | 0.6471 | 1.0335 | 0.3119 | 0.048* | |
C53 | 0.7023 (5) | 0.9603 (4) | 0.2523 (3) | 0.0439 (16) | |
H53 | 0.6921 | 0.9905 | 0.2136 | 0.053* | |
C54 | 0.7434 (5) | 0.8904 (3) | 0.2520 (3) | 0.0346 (14) | |
C55 | 0.7628 (5) | 0.8475 (3) | 0.3074 (3) | 0.0389 (15) | |
H55 | 0.7940 | 0.8005 | 0.3067 | 0.047* | |
C56 | 0.7360 (4) | 0.8737 (3) | 0.3654 (3) | 0.0341 (14) | |
H56 | 0.7487 | 0.8441 | 0.4045 | 0.041* | |
C57 | 0.5021 (5) | 0.8293 (4) | 0.3442 (3) | 0.0390 (15) | |
H57A | 0.5579 | 0.7974 | 0.3404 | 0.058* | |
H57B | 0.4995 | 0.8715 | 0.3136 | 0.058* | |
H57C | 0.4413 | 0.8005 | 0.3330 | 0.058* | |
H1 | 0.945 (4) | 0.549 (3) | 0.4604 (13) | 0.025 (15)* | |
H4 | 0.714 (6) | 0.448 (5) | 0.183 (2) | 0.07 (3)* | |
H7 | 0.597 (4) | 0.961 (3) | 0.5998 (14) | 0.029 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0667 (5) | 0.0405 (4) | 0.0384 (4) | 0.0011 (3) | 0.0204 (3) | −0.0002 (3) |
Br2 | 0.0833 (6) | 0.0431 (4) | 0.0402 (4) | −0.0016 (4) | 0.0255 (4) | −0.0011 (3) |
Br3 | 0.1005 (6) | 0.0459 (4) | 0.0433 (4) | −0.0090 (4) | 0.0349 (4) | −0.0081 (3) |
O1 | 0.047 (3) | 0.043 (3) | 0.037 (2) | 0.019 (2) | 0.012 (2) | 0.011 (2) |
O2 | 0.046 (3) | 0.040 (2) | 0.040 (3) | 0.021 (2) | 0.015 (2) | 0.012 (2) |
O3 | 0.049 (3) | 0.036 (2) | 0.036 (2) | −0.018 (2) | 0.013 (2) | −0.013 (2) |
N1 | 0.038 (3) | 0.031 (3) | 0.028 (3) | 0.009 (2) | 0.013 (2) | 0.009 (2) |
N2 | 0.034 (3) | 0.030 (3) | 0.037 (3) | 0.000 (2) | 0.001 (2) | 0.006 (2) |
N3 | 0.032 (3) | 0.027 (2) | 0.033 (3) | 0.002 (2) | 0.009 (2) | 0.003 (2) |
N4 | 0.038 (3) | 0.030 (3) | 0.028 (3) | 0.012 (2) | 0.012 (2) | 0.009 (2) |
N5 | 0.038 (3) | 0.023 (2) | 0.038 (3) | 0.006 (2) | 0.003 (2) | −0.001 (2) |
N6 | 0.034 (3) | 0.027 (2) | 0.027 (3) | 0.007 (2) | 0.007 (2) | 0.002 (2) |
N7 | 0.037 (3) | 0.028 (3) | 0.025 (3) | −0.007 (2) | 0.012 (2) | −0.006 (2) |
N8 | 0.030 (3) | 0.028 (3) | 0.032 (3) | −0.003 (2) | 0.008 (2) | −0.005 (2) |
N9 | 0.029 (2) | 0.026 (2) | 0.029 (3) | −0.005 (2) | 0.014 (2) | −0.004 (2) |
C1 | 0.027 (3) | 0.025 (3) | 0.035 (3) | 0.001 (2) | 0.011 (2) | 0.004 (2) |
C2 | 0.038 (3) | 0.022 (3) | 0.032 (3) | 0.001 (2) | 0.007 (3) | 0.004 (2) |
C3 | 0.046 (4) | 0.024 (3) | 0.039 (3) | −0.003 (3) | 0.016 (3) | −0.001 (3) |
C4 | 0.045 (4) | 0.041 (4) | 0.036 (3) | 0.013 (3) | 0.020 (3) | 0.007 (3) |
C5 | 0.037 (3) | 0.031 (3) | 0.039 (4) | 0.005 (3) | 0.012 (3) | 0.004 (3) |
C6 | 0.035 (3) | 0.028 (3) | 0.037 (3) | −0.005 (3) | 0.004 (3) | 0.001 (3) |
C7 | 0.035 (3) | 0.021 (3) | 0.041 (3) | 0.001 (2) | 0.015 (3) | 0.010 (2) |
C8 | 0.033 (3) | 0.044 (4) | 0.048 (4) | 0.003 (3) | 0.017 (3) | −0.001 (3) |
C9 | 0.058 (5) | 0.058 (5) | 0.038 (4) | 0.007 (4) | 0.019 (3) | −0.001 (3) |
C10 | 0.072 (5) | 0.053 (5) | 0.050 (5) | 0.026 (4) | 0.034 (4) | 0.019 (4) |
C11 | 0.049 (4) | 0.047 (4) | 0.069 (5) | 0.022 (3) | 0.037 (4) | 0.029 (4) |
C12 | 0.031 (3) | 0.033 (3) | 0.060 (4) | 0.006 (3) | 0.015 (3) | 0.015 (3) |
C13 | 0.041 (3) | 0.029 (3) | 0.035 (3) | 0.000 (3) | 0.012 (3) | 0.005 (3) |
C14 | 0.044 (4) | 0.030 (3) | 0.038 (3) | −0.006 (3) | 0.014 (3) | −0.006 (3) |
C15 | 0.047 (4) | 0.023 (3) | 0.043 (4) | −0.006 (3) | 0.015 (3) | 0.001 (3) |
C16 | 0.045 (4) | 0.025 (3) | 0.038 (3) | −0.002 (3) | 0.016 (3) | 0.000 (3) |
C17 | 0.090 (6) | 0.033 (4) | 0.033 (4) | −0.007 (4) | 0.020 (4) | −0.009 (3) |
C18 | 0.076 (5) | 0.028 (3) | 0.044 (4) | −0.011 (3) | 0.014 (4) | −0.008 (3) |
C19 | 0.047 (4) | 0.051 (4) | 0.033 (4) | 0.002 (3) | −0.002 (3) | 0.004 (3) |
C20 | 0.028 (3) | 0.019 (3) | 0.032 (3) | 0.003 (2) | 0.008 (2) | 0.000 (2) |
C21 | 0.030 (3) | 0.020 (3) | 0.043 (4) | 0.000 (2) | 0.009 (3) | −0.001 (3) |
C22 | 0.041 (3) | 0.025 (3) | 0.035 (3) | 0.002 (3) | 0.012 (3) | 0.002 (3) |
C23 | 0.039 (3) | 0.041 (4) | 0.035 (3) | 0.015 (3) | 0.018 (3) | 0.002 (3) |
C24 | 0.036 (3) | 0.029 (3) | 0.034 (3) | 0.005 (3) | 0.012 (3) | 0.005 (3) |
C25 | 0.033 (3) | 0.027 (3) | 0.031 (3) | 0.001 (2) | 0.002 (2) | −0.001 (2) |
C26 | 0.034 (3) | 0.024 (3) | 0.035 (3) | 0.007 (2) | 0.020 (3) | 0.007 (2) |
C27 | 0.038 (3) | 0.029 (3) | 0.044 (4) | 0.005 (3) | 0.013 (3) | 0.005 (3) |
C28 | 0.038 (4) | 0.041 (4) | 0.054 (4) | 0.015 (3) | 0.029 (3) | 0.001 (3) |
C29 | 0.059 (4) | 0.045 (4) | 0.033 (4) | 0.016 (3) | 0.018 (3) | 0.002 (3) |
C30 | 0.055 (4) | 0.052 (4) | 0.028 (3) | 0.014 (3) | 0.010 (3) | −0.003 (3) |
C31 | 0.039 (4) | 0.045 (4) | 0.031 (3) | 0.012 (3) | 0.007 (3) | −0.003 (3) |
C32 | 0.036 (3) | 0.023 (3) | 0.033 (3) | 0.002 (2) | 0.007 (3) | −0.003 (2) |
C33 | 0.062 (4) | 0.024 (3) | 0.038 (4) | −0.009 (3) | 0.012 (3) | −0.001 (3) |
C34 | 0.072 (5) | 0.028 (3) | 0.040 (4) | −0.010 (3) | 0.012 (3) | −0.008 (3) |
C35 | 0.050 (4) | 0.032 (3) | 0.033 (3) | 0.003 (3) | 0.013 (3) | 0.000 (3) |
C36 | 0.051 (4) | 0.025 (3) | 0.052 (4) | −0.009 (3) | 0.018 (3) | −0.012 (3) |
C37 | 0.064 (5) | 0.027 (3) | 0.043 (4) | −0.008 (3) | 0.018 (3) | −0.015 (3) |
C38 | 0.057 (4) | 0.045 (4) | 0.033 (4) | 0.011 (3) | −0.005 (3) | −0.003 (3) |
C39 | 0.033 (3) | 0.017 (3) | 0.032 (3) | −0.002 (2) | 0.006 (2) | 0.001 (2) |
C40 | 0.031 (3) | 0.024 (3) | 0.026 (3) | 0.004 (2) | 0.007 (2) | 0.000 (2) |
C41 | 0.038 (3) | 0.024 (3) | 0.035 (3) | 0.003 (2) | 0.012 (3) | −0.001 (2) |
C42 | 0.036 (3) | 0.038 (3) | 0.034 (3) | −0.011 (3) | 0.017 (3) | −0.007 (3) |
C43 | 0.036 (3) | 0.023 (3) | 0.040 (3) | −0.003 (2) | 0.014 (3) | −0.002 (3) |
C44 | 0.029 (3) | 0.027 (3) | 0.032 (3) | 0.003 (2) | 0.003 (2) | −0.001 (2) |
C45 | 0.035 (3) | 0.020 (3) | 0.037 (3) | −0.005 (2) | 0.009 (3) | −0.005 (2) |
C46 | 0.030 (3) | 0.030 (3) | 0.051 (4) | −0.001 (3) | 0.019 (3) | −0.003 (3) |
C47 | 0.048 (4) | 0.035 (4) | 0.068 (5) | −0.005 (3) | 0.030 (4) | −0.008 (3) |
C48 | 0.091 (6) | 0.040 (4) | 0.052 (5) | −0.015 (4) | 0.037 (4) | −0.010 (4) |
C49 | 0.071 (5) | 0.047 (4) | 0.047 (4) | −0.021 (4) | 0.004 (4) | 0.006 (3) |
C50 | 0.054 (4) | 0.038 (4) | 0.047 (4) | −0.017 (3) | 0.006 (3) | 0.001 (3) |
C51 | 0.034 (3) | 0.024 (3) | 0.031 (3) | −0.003 (2) | 0.009 (2) | 0.000 (2) |
C52 | 0.054 (4) | 0.025 (3) | 0.043 (4) | 0.003 (3) | 0.016 (3) | 0.006 (3) |
C53 | 0.068 (5) | 0.034 (3) | 0.033 (3) | 0.003 (3) | 0.019 (3) | 0.011 (3) |
C54 | 0.053 (4) | 0.036 (3) | 0.021 (3) | −0.005 (3) | 0.022 (3) | −0.010 (3) |
C55 | 0.051 (4) | 0.025 (3) | 0.043 (4) | 0.005 (3) | 0.016 (3) | 0.001 (3) |
C56 | 0.043 (4) | 0.030 (3) | 0.032 (3) | 0.002 (3) | 0.015 (3) | 0.011 (3) |
C57 | 0.041 (4) | 0.041 (4) | 0.034 (3) | −0.006 (3) | 0.005 (3) | −0.004 (3) |
Br1—C16 | 1.899 (6) | C22—C23 | 1.534 (8) |
Br2—C35 | 1.902 (6) | C22—H22 | 1.00 |
Br3—C54 | 1.904 (5) | C23—C24 | 1.509 (8) |
O1—C5 | 1.238 (7) | C23—H23A | 0.99 |
O2—C24 | 1.229 (7) | C23—H23B | 0.99 |
O3—C43 | 1.224 (7) | C25—C38 | 1.487 (8) |
N1—C5 | 1.365 (7) | C26—C31 | 1.378 (8) |
N1—C1 | 1.396 (7) | C26—C27 | 1.388 (8) |
N1—H1 | 0.883 (10) | C27—C28 | 1.387 (9) |
N2—C6 | 1.329 (8) | C27—H27 | 0.95 |
N2—N3 | 1.375 (7) | C28—C29 | 1.381 (10) |
N3—C1 | 1.365 (7) | C28—H28 | 0.95 |
N3—C7 | 1.403 (7) | C29—C30 | 1.371 (9) |
N4—C24 | 1.355 (7) | C29—H29 | 0.95 |
N4—C20 | 1.401 (7) | C30—C31 | 1.384 (8) |
N4—H4 | 0.881 (10) | C30—H30 | 0.95 |
N5—C25 | 1.324 (7) | C31—H31 | 0.95 |
N5—N6 | 1.388 (7) | C32—C33 | 1.379 (8) |
N6—C20 | 1.352 (7) | C32—C37 | 1.382 (8) |
N6—C26 | 1.417 (7) | C33—C34 | 1.374 (9) |
N7—C43 | 1.368 (7) | C33—H33 | 0.95 |
N7—C39 | 1.398 (7) | C34—C35 | 1.371 (9) |
N7—H7 | 0.877 (10) | C34—H34 | 0.95 |
N8—C44 | 1.330 (7) | C35—C36 | 1.377 (8) |
N8—N9 | 1.373 (6) | C36—C37 | 1.375 (9) |
N9—C39 | 1.357 (7) | C36—H36 | 0.95 |
N9—C45 | 1.433 (7) | C37—H37 | 0.95 |
C1—C2 | 1.343 (8) | C38—H38A | 0.98 |
C2—C6 | 1.426 (8) | C38—H38B | 0.98 |
C2—C3 | 1.500 (8) | C38—H38C | 0.98 |
C3—C13 | 1.506 (8) | C39—C40 | 1.357 (8) |
C3—C4 | 1.542 (9) | C40—C44 | 1.409 (8) |
C3—H3 | 1.00 | C40—C41 | 1.495 (8) |
C4—C5 | 1.492 (8) | C41—C51 | 1.520 (8) |
C4—H4A | 0.99 | C41—C42 | 1.533 (8) |
C4—H4B | 0.99 | C41—H41 | 1.00 |
C6—C19 | 1.480 (8) | C42—C43 | 1.513 (8) |
C7—C8 | 1.374 (9) | C42—H42A | 0.99 |
C7—C12 | 1.398 (8) | C42—H42B | 0.99 |
C8—C9 | 1.378 (9) | C44—C57 | 1.493 (8) |
C8—H8 | 0.95 | C45—C46 | 1.371 (8) |
C9—C10 | 1.370 (10) | C45—C50 | 1.376 (9) |
C9—H9 | 0.95 | C46—C47 | 1.398 (9) |
C10—C11 | 1.370 (11) | C46—H46 | 0.95 |
C10—H10 | 0.95 | C47—C48 | 1.360 (11) |
C11—C12 | 1.358 (10) | C47—H47 | 0.95 |
C11—H11 | 0.95 | C48—C49 | 1.381 (11) |
C12—H12 | 0.95 | C48—H48 | 0.95 |
C13—C18 | 1.384 (9) | C49—C50 | 1.391 (10) |
C13—C14 | 1.388 (8) | C49—H49 | 0.95 |
C14—C15 | 1.387 (8) | C50—H50 | 0.95 |
C14—H14 | 0.95 | C51—C52 | 1.374 (8) |
C15—C16 | 1.365 (8) | C51—C56 | 1.376 (8) |
C15—H15 | 0.95 | C52—C53 | 1.395 (9) |
C16—C17 | 1.382 (9) | C52—H52 | 0.95 |
C17—C18 | 1.378 (9) | C53—C54 | 1.381 (9) |
C17—H17 | 0.95 | C53—H53 | 0.95 |
C18—H18 | 0.95 | C54—C55 | 1.357 (8) |
C19—H19A | 0.98 | C55—C56 | 1.395 (8) |
C19—H19B | 0.98 | C55—H55 | 0.95 |
C19—H19C | 0.98 | C56—H56 | 0.95 |
C20—C21 | 1.365 (8) | C57—H57A | 0.98 |
C21—C25 | 1.408 (8) | C57—H57B | 0.98 |
C21—C22 | 1.498 (8) | C57—H57C | 0.98 |
C22—C32 | 1.520 (8) | ||
C5—N1—C1 | 118.3 (5) | C21—C25—C38 | 129.0 (6) |
C5—N1—H1 | 118 (4) | C31—C26—C27 | 120.5 (6) |
C1—N1—H1 | 123 (4) | C31—C26—N6 | 120.7 (5) |
C6—N2—N3 | 105.9 (5) | C27—C26—N6 | 118.8 (6) |
C1—N3—N2 | 109.5 (5) | C28—C27—C26 | 118.5 (6) |
C1—N3—C7 | 131.1 (5) | C28—C27—H27 | 120.8 |
N2—N3—C7 | 119.1 (5) | C26—C27—H27 | 120.8 |
C24—N4—C20 | 119.0 (5) | C29—C28—C27 | 121.0 (6) |
C24—N4—H4 | 118 (5) | C29—C28—H28 | 119.5 |
C20—N4—H4 | 122 (5) | C27—C28—H28 | 119.5 |
C25—N5—N6 | 104.6 (4) | C30—C29—C28 | 120.0 (6) |
C20—N6—N5 | 109.7 (4) | C30—C29—H29 | 120.0 |
C20—N6—C26 | 131.6 (5) | C28—C29—H29 | 120.0 |
N5—N6—C26 | 118.4 (4) | C29—C30—C31 | 119.9 (6) |
C43—N7—C39 | 118.4 (5) | C29—C30—H30 | 120.1 |
C43—N7—H7 | 117 (4) | C31—C30—H30 | 120.1 |
C39—N7—H7 | 125 (4) | C26—C31—C30 | 120.2 (6) |
C44—N8—N9 | 104.5 (4) | C26—C31—H31 | 119.9 |
C39—N9—N8 | 110.2 (4) | C30—C31—H31 | 119.9 |
C39—N9—C45 | 130.6 (5) | C33—C32—C37 | 116.9 (6) |
N8—N9—C45 | 119.2 (4) | C33—C32—C22 | 121.0 (5) |
C2—C1—N3 | 109.2 (5) | C37—C32—C22 | 121.9 (5) |
C2—C1—N1 | 125.1 (5) | C34—C33—C32 | 122.0 (6) |
N3—C1—N1 | 125.6 (5) | C34—C33—H33 | 119.0 |
C1—C2—C6 | 104.8 (5) | C32—C33—H33 | 119.0 |
C1—C2—C3 | 120.8 (5) | C35—C34—C33 | 119.5 (6) |
C6—C2—C3 | 134.4 (6) | C35—C34—H34 | 120.3 |
C2—C3—C13 | 112.0 (5) | C33—C34—H34 | 120.3 |
C2—C3—C4 | 106.8 (5) | C34—C35—C36 | 120.5 (6) |
C13—C3—C4 | 112.2 (5) | C34—C35—Br2 | 120.3 (5) |
C2—C3—H3 | 108.6 | C36—C35—Br2 | 119.2 (5) |
C13—C3—H3 | 108.6 | C37—C36—C35 | 118.7 (6) |
C4—C3—H3 | 108.6 | C37—C36—H36 | 120.7 |
C5—C4—C3 | 115.0 (5) | C35—C36—H36 | 120.7 |
C5—C4—H4A | 108.5 | C36—C37—C32 | 122.5 (6) |
C3—C4—H4A | 108.5 | C36—C37—H37 | 118.8 |
C5—C4—H4B | 108.5 | C32—C37—H37 | 118.8 |
C3—C4—H4B | 108.5 | C25—C38—H38A | 109.5 |
H4A—C4—H4B | 107.5 | C25—C38—H38B | 109.5 |
O1—C5—N1 | 120.6 (5) | H38A—C38—H38B | 109.5 |
O1—C5—C4 | 122.7 (5) | C25—C38—H38C | 109.5 |
N1—C5—C4 | 116.6 (5) | H38A—C38—H38C | 109.5 |
N2—C6—C2 | 110.6 (5) | H38B—C38—H38C | 109.5 |
N2—C6—C19 | 119.6 (6) | C40—C39—N9 | 109.3 (5) |
C2—C6—C19 | 129.8 (6) | C40—C39—N7 | 125.2 (5) |
C8—C7—C12 | 119.7 (6) | N9—C39—N7 | 125.5 (5) |
C8—C7—N3 | 121.3 (5) | C39—C40—C44 | 103.6 (5) |
C12—C7—N3 | 119.1 (6) | C39—C40—C41 | 119.1 (5) |
C7—C8—C9 | 120.0 (6) | C44—C40—C41 | 137.2 (5) |
C7—C8—H8 | 120.0 | C40—C41—C51 | 112.9 (5) |
C9—C8—H8 | 120.0 | C40—C41—C42 | 107.7 (5) |
C10—C9—C8 | 120.2 (7) | C51—C41—C42 | 111.8 (5) |
C10—C9—H9 | 119.9 | C40—C41—H41 | 108.1 |
C8—C9—H9 | 119.9 | C51—C41—H41 | 108.1 |
C11—C10—C9 | 119.5 (7) | C42—C41—H41 | 108.1 |
C11—C10—H10 | 120.3 | C43—C42—C41 | 113.8 (5) |
C9—C10—H10 | 120.3 | C43—C42—H42A | 108.8 |
C12—C11—C10 | 121.6 (7) | C41—C42—H42A | 108.8 |
C12—C11—H11 | 119.2 | C43—C42—H42B | 108.8 |
C10—C11—H11 | 119.2 | C41—C42—H42B | 108.8 |
C11—C12—C7 | 119.0 (7) | H42A—C42—H42B | 107.7 |
C11—C12—H12 | 120.5 | O3—C43—N7 | 121.0 (5) |
C7—C12—H12 | 120.5 | O3—C43—C42 | 121.6 (5) |
C18—C13—C14 | 117.9 (6) | N7—C43—C42 | 117.4 (5) |
C18—C13—C3 | 121.6 (6) | N8—C44—C40 | 112.5 (5) |
C14—C13—C3 | 120.2 (5) | N8—C44—C57 | 118.8 (5) |
C15—C14—C13 | 121.2 (6) | C40—C44—C57 | 128.5 (5) |
C15—C14—H14 | 119.4 | C46—C45—C50 | 120.8 (6) |
C13—C14—H14 | 119.4 | C46—C45—N9 | 119.6 (5) |
C16—C15—C14 | 119.0 (6) | C50—C45—N9 | 119.5 (5) |
C16—C15—H15 | 120.5 | C45—C46—C47 | 119.6 (6) |
C14—C15—H15 | 120.5 | C45—C46—H46 | 120.2 |
C15—C16—C17 | 121.5 (6) | C47—C46—H46 | 120.2 |
C15—C16—Br1 | 119.2 (4) | C48—C47—C46 | 120.1 (7) |
C17—C16—Br1 | 119.3 (5) | C48—C47—H47 | 120.0 |
C18—C17—C16 | 118.6 (6) | C46—C47—H47 | 120.0 |
C18—C17—H17 | 120.7 | C47—C48—C49 | 120.1 (7) |
C16—C17—H17 | 120.7 | C47—C48—H48 | 120.0 |
C17—C18—C13 | 121.7 (6) | C49—C48—H48 | 120.0 |
C17—C18—H18 | 119.1 | C48—C49—C50 | 120.4 (7) |
C13—C18—H18 | 119.1 | C48—C49—H49 | 119.8 |
C6—C19—H19A | 109.5 | C50—C49—H49 | 119.8 |
C6—C19—H19B | 109.5 | C45—C50—C49 | 119.0 (7) |
H19A—C19—H19B | 109.5 | C45—C50—H50 | 120.5 |
C6—C19—H19C | 109.5 | C49—C50—H50 | 120.5 |
H19A—C19—H19C | 109.5 | C52—C51—C56 | 119.4 (5) |
H19B—C19—H19C | 109.5 | C52—C51—C41 | 119.7 (5) |
N6—C20—C21 | 109.5 (5) | C56—C51—C41 | 120.7 (5) |
N6—C20—N4 | 125.9 (5) | C51—C52—C53 | 120.4 (6) |
C21—C20—N4 | 124.5 (5) | C51—C52—H52 | 119.8 |
C20—C21—C25 | 103.5 (5) | C53—C52—H52 | 119.8 |
C20—C21—C22 | 120.4 (5) | C54—C53—C52 | 118.6 (6) |
C25—C21—C22 | 136.0 (6) | C54—C53—H53 | 120.7 |
C21—C22—C32 | 112.8 (5) | C52—C53—H53 | 120.7 |
C21—C22—C23 | 107.3 (5) | C55—C54—C53 | 121.9 (5) |
C32—C22—C23 | 112.9 (5) | C55—C54—Br3 | 119.5 (5) |
C21—C22—H22 | 107.9 | C53—C54—Br3 | 118.6 (5) |
C32—C22—H22 | 107.9 | C54—C55—C56 | 118.6 (6) |
C23—C22—H22 | 107.9 | C54—C55—H55 | 120.7 |
C24—C23—C22 | 115.7 (5) | C56—C55—H55 | 120.7 |
C24—C23—H23A | 108.4 | C51—C56—C55 | 120.9 (5) |
C22—C23—H23A | 108.4 | C51—C56—H56 | 119.5 |
C24—C23—H23B | 108.4 | C55—C56—H56 | 119.5 |
C22—C23—H23B | 108.4 | C44—C57—H57A | 109.5 |
H23A—C23—H23B | 107.4 | C44—C57—H57B | 109.5 |
O2—C24—N4 | 121.2 (5) | H57A—C57—H57B | 109.5 |
O2—C24—C23 | 121.7 (5) | C44—C57—H57C | 109.5 |
N4—C24—C23 | 116.9 (5) | H57A—C57—H57C | 109.5 |
N5—C25—C21 | 112.7 (5) | H57B—C57—H57C | 109.5 |
N5—C25—C38 | 118.3 (5) | ||
C6—N2—N3—C1 | −0.7 (6) | C22—C21—C25—N5 | −177.7 (6) |
C6—N2—N3—C7 | 173.5 (5) | C20—C21—C25—C38 | −179.3 (6) |
C25—N5—N6—C20 | 0.4 (6) | C22—C21—C25—C38 | 3.3 (11) |
C25—N5—N6—C26 | −174.4 (5) | C20—N6—C26—C31 | −36.1 (9) |
C44—N8—N9—C39 | 0.7 (6) | N5—N6—C26—C31 | 137.4 (6) |
C44—N8—N9—C45 | −176.7 (5) | C20—N6—C26—C27 | 145.6 (6) |
N2—N3—C1—C2 | 0.5 (6) | N5—N6—C26—C27 | −40.9 (7) |
C7—N3—C1—C2 | −172.8 (5) | C31—C26—C27—C28 | −2.0 (9) |
N2—N3—C1—N1 | −176.2 (5) | N6—C26—C27—C28 | 176.3 (5) |
C7—N3—C1—N1 | 10.5 (9) | C26—C27—C28—C29 | 0.2 (9) |
C5—N1—C1—C2 | 11.4 (9) | C27—C28—C29—C30 | 1.3 (10) |
C5—N1—C1—N3 | −172.5 (5) | C28—C29—C30—C31 | −0.9 (10) |
N3—C1—C2—C6 | 0.0 (6) | C27—C26—C31—C30 | 2.4 (9) |
N1—C1—C2—C6 | 176.7 (5) | N6—C26—C31—C30 | −175.9 (6) |
N3—C1—C2—C3 | 179.5 (5) | C29—C30—C31—C26 | −0.9 (10) |
N1—C1—C2—C3 | −3.8 (9) | C21—C22—C32—C33 | 117.3 (6) |
C1—C2—C3—C13 | −147.5 (6) | C23—C22—C32—C33 | −120.9 (6) |
C6—C2—C3—C13 | 31.9 (9) | C21—C22—C32—C37 | −58.7 (8) |
C1—C2—C3—C4 | −24.4 (7) | C23—C22—C32—C37 | 63.1 (8) |
C6—C2—C3—C4 | 155.0 (6) | C37—C32—C33—C34 | 0.9 (10) |
C2—C3—C4—C5 | 46.1 (7) | C22—C32—C33—C34 | −175.3 (6) |
C13—C3—C4—C5 | 169.2 (5) | C32—C33—C34—C35 | 0.1 (11) |
C1—N1—C5—O1 | −171.0 (6) | C33—C34—C35—C36 | −0.7 (11) |
C1—N1—C5—C4 | 12.7 (8) | C33—C34—C35—Br2 | 177.4 (5) |
C3—C4—C5—O1 | 141.0 (6) | C34—C35—C36—C37 | 0.3 (10) |
C3—C4—C5—N1 | −42.8 (8) | Br2—C35—C36—C37 | −177.8 (5) |
N3—N2—C6—C2 | 0.7 (6) | C35—C36—C37—C32 | 0.7 (11) |
N3—N2—C6—C19 | −179.1 (5) | C33—C32—C37—C36 | −1.3 (10) |
C1—C2—C6—N2 | −0.5 (7) | C22—C32—C37—C36 | 174.9 (6) |
C3—C2—C6—N2 | −179.9 (6) | N8—N9—C39—C40 | 0.2 (6) |
C1—C2—C6—C19 | 179.4 (6) | C45—N9—C39—C40 | 177.2 (5) |
C3—C2—C6—C19 | −0.1 (11) | N8—N9—C39—N7 | 178.6 (5) |
C1—N3—C7—C8 | 37.1 (9) | C45—N9—C39—N7 | −4.4 (9) |
N2—N3—C7—C8 | −135.7 (6) | C43—N7—C39—C40 | −13.0 (8) |
C1—N3—C7—C12 | −143.9 (6) | C43—N7—C39—N9 | 168.8 (5) |
N2—N3—C7—C12 | 43.4 (7) | N9—C39—C40—C44 | −1.0 (6) |
C12—C7—C8—C9 | −0.6 (9) | N7—C39—C40—C44 | −179.4 (5) |
N3—C7—C8—C9 | 178.4 (6) | N9—C39—C40—C41 | 176.5 (5) |
C7—C8—C9—C10 | −0.6 (11) | N7—C39—C40—C41 | −1.9 (9) |
C8—C9—C10—C11 | 1.1 (11) | C39—C40—C41—C51 | 156.0 (5) |
C9—C10—C11—C12 | −0.4 (11) | C44—C40—C41—C51 | −27.6 (9) |
C10—C11—C12—C7 | −0.8 (10) | C39—C40—C41—C42 | 32.0 (7) |
C8—C7—C12—C11 | 1.3 (9) | C44—C40—C41—C42 | −151.6 (7) |
N3—C7—C12—C11 | −177.7 (5) | C40—C41—C42—C43 | −48.6 (6) |
C2—C3—C13—C18 | −117.5 (7) | C51—C41—C42—C43 | −173.3 (5) |
C4—C3—C13—C18 | 122.4 (7) | C39—N7—C43—O3 | 175.9 (5) |
C2—C3—C13—C14 | 56.1 (8) | C39—N7—C43—C42 | −6.4 (8) |
C4—C3—C13—C14 | −64.0 (7) | C41—C42—C43—O3 | −144.1 (6) |
C18—C13—C14—C15 | 1.4 (10) | C41—C42—C43—N7 | 38.2 (8) |
C3—C13—C14—C15 | −172.5 (6) | N9—N8—C44—C40 | −1.3 (6) |
C13—C14—C15—C16 | 0.0 (10) | N9—N8—C44—C57 | 174.8 (5) |
C14—C15—C16—C17 | −2.2 (10) | C39—C40—C44—N8 | 1.5 (6) |
C14—C15—C16—Br1 | 177.0 (5) | C41—C40—C44—N8 | −175.3 (6) |
C15—C16—C17—C18 | 2.9 (11) | C39—C40—C44—C57 | −174.1 (6) |
Br1—C16—C17—C18 | −176.3 (6) | C41—C40—C44—C57 | 9.1 (11) |
C16—C17—C18—C13 | −1.4 (12) | C39—N9—C45—C46 | 135.9 (6) |
C14—C13—C18—C17 | −0.7 (11) | N8—N9—C45—C46 | −47.4 (7) |
C3—C13—C18—C17 | 173.1 (7) | C39—N9—C45—C50 | −44.4 (9) |
N5—N6—C20—C21 | −0.6 (6) | N8—N9—C45—C50 | 132.3 (6) |
C26—N6—C20—C21 | 173.3 (5) | C50—C45—C46—C47 | −0.5 (9) |
N5—N6—C20—N4 | 175.6 (5) | N9—C45—C46—C47 | 179.3 (5) |
C26—N6—C20—N4 | −10.5 (10) | C45—C46—C47—C48 | 1.4 (10) |
C24—N4—C20—N6 | 171.2 (5) | C46—C47—C48—C49 | −1.9 (11) |
C24—N4—C20—C21 | −13.2 (9) | C47—C48—C49—C50 | 1.3 (11) |
N6—C20—C21—C25 | 0.5 (6) | C46—C45—C50—C49 | −0.1 (10) |
N4—C20—C21—C25 | −175.7 (5) | N9—C45—C50—C49 | −179.8 (6) |
N6—C20—C21—C22 | 178.5 (5) | C48—C49—C50—C45 | −0.4 (11) |
N4—C20—C21—C22 | 2.2 (9) | C40—C41—C51—C52 | 119.4 (6) |
C20—C21—C22—C32 | 151.1 (5) | C42—C41—C51—C52 | −118.9 (6) |
C25—C21—C22—C32 | −31.7 (9) | C40—C41—C51—C56 | −54.9 (8) |
C20—C21—C22—C23 | 26.2 (7) | C42—C41—C51—C56 | 66.7 (7) |
C25—C21—C22—C23 | −156.7 (7) | C56—C51—C52—C53 | 2.1 (10) |
C21—C22—C23—C24 | −45.2 (7) | C41—C51—C52—C53 | −172.3 (6) |
C32—C22—C23—C24 | −170.1 (5) | C51—C52—C53—C54 | 0.4 (10) |
C20—N4—C24—O2 | 176.2 (5) | C52—C53—C54—C55 | −3.1 (10) |
C20—N4—C24—C23 | −8.0 (8) | C52—C53—C54—Br3 | 175.5 (5) |
C22—C23—C24—O2 | −145.6 (6) | C53—C54—C55—C56 | 3.1 (10) |
C22—C23—C24—N4 | 38.6 (8) | Br3—C54—C55—C56 | −175.4 (5) |
N6—N5—C25—C21 | −0.1 (6) | C52—C51—C56—C55 | −2.1 (9) |
N6—N5—C25—C38 | 179.0 (5) | C41—C51—C56—C55 | 172.3 (6) |
C20—C21—C25—N5 | −0.2 (7) | C54—C55—C56—C51 | −0.4 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 (1) | 1.94 (1) | 2.812 (6) | 172 (5) |
N4—H4···O3ii | 0.88 (1) | 1.94 (2) | 2.814 (6) | 173 (8) |
N7—H7···O2iii | 0.88 (1) | 1.96 (1) | 2.834 (6) | 174 (6) |
C4—H4A···Br3iv | 0.99 | 2.84 | 3.826 (7) | 173 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+2, y−1/2, −z+1/2. |
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