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The title molecular complex, C
25H
25BrF
3N
4+·C
6H
2N
3O
7−, crystallizes with two pairs of cations and anions in the asymmetric unit. While the orientations of the two cations are nearly parallel to one another, this is not so for the anions. The imidazonaphthyridine moiety is planar and the methylpiperidine group is approximately perpendicular to it and adopts an ideal chair conformation. The planes of the bromophenyl rings deviate from the planes of the imidazonaphthyridine moieties by 30.2 (2) and 22.6 (3)° in the two cations, making a marked difference in the overall conformation of the cations. The N—H
N hydrogen bond forms an intramolecular ring pattern
S(7) in both cations. The anions and cations are connected through N—H
O, C—H
O and C—H
F hydrogen bonds.
Supporting information
CCDC reference: 272104
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.012 Å
- R factor = 0.081
- wR factor = 0.257
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent O Ueq(max)/Ueq(min) ... 6.22 Ratio
| Author Response: O2B possesses high displacement parameters. However no
suitable disorder model was found.
|
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for N1B
| Author Response: N1B is part of the nitrogroup containing O2B which possesses
high displacment parameters.
|
Alert level B
PLAT213_ALERT_2_B Atom O2B has ADP max/min Ratio ............. 4.60 prolat
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.257
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT084_ALERT_2_C High R2 Value .................................. 0.26
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18A
| Author Response: N1B is part of the nitrogroup containing O2B which possesses
high displacment parameters.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18B
| Author Response: N1B is part of the nitrogroup containing O2B which possesses
high displacment parameters.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1A
| Author Response: N1B is part of the nitrogroup containing O2B which possesses
high displacment parameters.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2B
| Author Response: N1B is part of the nitrogroup containing O2B which possesses
high displacment parameters.
|
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.51
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C17A
PLAT432_ALERT_2_C Short Inter X...Y Contact O4B .. C14B .. 2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H30B .. O7B .. 2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24B .. F1A .. 2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24D .. F1B .. 2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28A .. F1B .. 2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28B .. F2A .. 2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B .. F3B .. 2.84 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 34.00 A 3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4
C6 H2 N3 O7
2 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
23 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
11 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
8 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
1-[4-methylpiperdinemethyl]-2-[4-bromophenyl]-
6-methyl-8-trifluromethylimidazo[1,2-
a][1,8]naphthyridinium picrate
top
Crystal data top
C25H25BrF3N4+·C6H2N3O7− | F(000) = 3040 |
Mr = 746.51 | Dx = 1.516 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 12.6304 (13) Å | θ = 25–45° |
b = 50.875 (7) Å | µ = 2.38 mm−1 |
c = 11.017 (3) Å | T = 293 K |
β = 112.50 (1)° | Prism, yellow |
V = 6540 (2) Å3 | 0.4 × 0.3 × 0.28 mm |
Z = 8 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 6405 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 75.0°, θmin = 3.5° |
ω–2θ scans | h = −5→15 |
Absorption correction: ψ scan (North et al., 1968) | k = −63→10 |
Tmin = 0.472, Tmax = 0.514 | l = −13→12 |
13650 measured reflections | 2 standard reflections every 100 reflections |
13129 independent reflections | intensity decay: 1% |
Refinement top
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)] = 0.081 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.257 | H-atom parameters not refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0824P)2 + 13.6596P] where P = (Fo2 + 2Fc2)/3 |
13129 reflections | (Δ/σ)max = 0.001 |
883 parameters | Δρmax = 0.77 e Å−3 |
0 restraints | Δρmin = −0.62 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 1.2715 (4) | 0.56980 (11) | 0.7850 (5) | 0.0903 (15) | |
N1A | 1.1404 (7) | 0.61842 (14) | 0.7335 (6) | 0.0850 (17) | |
O2A | 1.2447 (6) | 0.62146 (12) | 0.7788 (7) | 0.118 (2) | |
O3A | 1.0742 (6) | 0.63616 (12) | 0.6844 (7) | 0.123 (2) | |
N2A | 0.8120 (6) | 0.5659 (2) | 0.6980 (9) | 0.128 (3) | |
O4A | 0.7553 (6) | 0.58636 (16) | 0.6631 (10) | 0.167 (3) | |
O5A | 0.7702 (6) | 0.54568 (19) | 0.7152 (11) | 0.176 (4) | |
N3A | 1.1770 (6) | 0.52278 (14) | 0.8351 (8) | 0.0914 (19) | |
O6A | 1.1329 (6) | 0.50134 (12) | 0.7881 (8) | 0.134 (3) | |
O7A | 1.2716 (6) | 0.52422 (12) | 0.9211 (7) | 0.116 (2) | |
C1A | 1.1704 (5) | 0.56966 (14) | 0.7738 (6) | 0.0649 (16) | |
C2A | 1.0954 (6) | 0.59220 (13) | 0.7411 (6) | 0.0657 (16) | |
C3A | 0.9809 (6) | 0.59128 (15) | 0.7161 (7) | 0.0771 (19) | |
H3A | 0.9368 | 0.6065 | 0.6949 | 0.093* | |
C4A | 0.9322 (6) | 0.56744 (18) | 0.7229 (8) | 0.085 (2) | |
C5A | 0.9975 (6) | 0.54470 (14) | 0.7607 (8) | 0.079 (2) | |
H5A | 0.9637 | 0.5288 | 0.7673 | 0.095* | |
C6A | 1.1112 (5) | 0.54608 (14) | 0.7877 (6) | 0.0669 (17) | |
Br1A | 0.82695 (10) | 0.70759 (2) | 0.81561 (9) | 0.1219 (4) | |
F1A | 0.3194 (6) | 0.51042 (11) | 0.6582 (5) | 0.147 (2) | |
F2A | 0.3342 (6) | 0.50690 (11) | 0.4760 (7) | 0.154 (2) | |
F3A | 0.1919 (6) | 0.49033 (11) | 0.5056 (6) | 0.150 (2) | |
N4A | 0.3109 (5) | 0.64639 (11) | 0.5208 (5) | 0.0741 (15) | |
N5A | 0.2637 (5) | 0.55787 (13) | 0.5188 (5) | 0.0777 (16) | |
N6A | 0.2796 (5) | 0.60324 (11) | 0.5131 (5) | 0.0659 (13) | |
N7A | 0.4782 (4) | 0.57304 (9) | 0.7605 (4) | 0.0568 (12) | |
H7A | 0.4046 | 0.5691 | 0.7484 | 0.068* | |
C7A | 0.2320 (7) | 0.62785 (15) | 0.4777 (7) | 0.0742 (18) | |
C8A | 0.1130 (7) | 0.63016 (18) | 0.4052 (7) | 0.086 (2) | |
H8A | 0.0814 | 0.6468 | 0.3809 | 0.104* | |
C9A | 0.0460 (7) | 0.6096 (2) | 0.3713 (7) | 0.093 (2) | |
H9A | −0.0317 | 0.6118 | 0.3216 | 0.111* | |
C10A | 0.0916 (6) | 0.58355 (18) | 0.4101 (6) | 0.082 (2) | |
C11A | 0.0239 (7) | 0.56109 (19) | 0.3814 (7) | 0.089 (2) | |
C12A | 0.0786 (8) | 0.53752 (18) | 0.4220 (8) | 0.092 (2) | |
H12A | 0.0364 | 0.5220 | 0.4043 | 0.110* | |
C13A | 0.1949 (8) | 0.53667 (16) | 0.4882 (6) | 0.081 (2) | |
C14A | 0.2095 (6) | 0.58019 (15) | 0.4794 (6) | 0.0715 (18) | |
C15A | 0.3960 (6) | 0.60692 (13) | 0.5820 (6) | 0.0632 (16) | |
C16A | 0.4127 (6) | 0.63372 (13) | 0.5852 (6) | 0.0687 (17) | |
C17A | −0.1038 (8) | 0.56197 (19) | 0.3070 (10) | 0.128 (4) | |
H17A | −0.1342 | 0.5445 | 0.2971 | 0.192* | |
H17B | −0.1205 | 0.5695 | 0.2218 | 0.192* | |
H17C | −0.1382 | 0.5725 | 0.3544 | 0.192* | |
C18A | 0.2585 (10) | 0.5114 (2) | 0.5299 (9) | 0.107 (3) | |
C19A | 0.4791 (6) | 0.58484 (12) | 0.6349 (6) | 0.0649 (16) | |
H19A | 0.5556 | 0.5912 | 0.6509 | 0.078* | |
H19B | 0.4615 | 0.5711 | 0.5688 | 0.078* | |
C20A | 0.5242 (6) | 0.59177 (12) | 0.8719 (6) | 0.0700 (17) | |
H20A | 0.4770 | 0.6075 | 0.8526 | 0.084* | |
H20B | 0.6014 | 0.5969 | 0.8831 | 0.084* | |
C21A | 0.5258 (7) | 0.57940 (14) | 0.9978 (6) | 0.0788 (19) | |
H21A | 0.4478 | 0.5758 | 0.9889 | 0.095* | |
H21B | 0.5589 | 0.5917 | 1.0696 | 0.095* | |
C22A | 0.5950 (6) | 0.55377 (14) | 1.0303 (7) | 0.0764 (19) | |
H22A | 0.6746 | 0.5579 | 1.0440 | 0.092* | |
C23A | 0.5480 (6) | 0.53547 (13) | 0.9156 (7) | 0.0762 (19) | |
H23A | 0.4708 | 0.5303 | 0.9041 | 0.091* | |
H23B | 0.5948 | 0.5197 | 0.9330 | 0.091* | |
C24A | 0.5460 (6) | 0.54825 (12) | 0.7905 (7) | 0.0738 (18) | |
H24A | 0.6239 | 0.5520 | 0.7995 | 0.089* | |
H24B | 0.5131 | 0.5361 | 0.7179 | 0.089* | |
C25A | 0.5937 (8) | 0.54179 (18) | 1.1547 (8) | 0.108 (3) | |
H25A | 0.6381 | 0.5259 | 1.1739 | 0.163* | |
H25B | 0.5162 | 0.5379 | 1.1435 | 0.163* | |
H25C | 0.6261 | 0.5540 | 1.2259 | 0.163* | |
C26A | 0.5156 (6) | 0.64990 (13) | 0.6461 (6) | 0.0690 (17) | |
C27A | 0.5030 (8) | 0.67524 (16) | 0.6868 (8) | 0.093 (2) | |
H27A | 0.4307 | 0.6810 | 0.6791 | 0.112* | |
C28A | 0.5951 (9) | 0.69205 (17) | 0.7383 (9) | 0.104 (3) | |
H28A | 0.5846 | 0.7088 | 0.7653 | 0.124* | |
C29A | 0.7014 (8) | 0.68407 (17) | 0.7494 (7) | 0.090 (2) | |
C30A | 0.7171 (7) | 0.65930 (17) | 0.7125 (7) | 0.085 (2) | |
H30A | 0.7902 | 0.6538 | 0.7220 | 0.102* | |
C31A | 0.6254 (7) | 0.64211 (14) | 0.6610 (6) | 0.0756 (19) | |
H31A | 0.6374 | 0.6253 | 0.6362 | 0.091* | |
O1B | 0.9506 (4) | 0.33215 (11) | 0.8656 (6) | 0.0976 (16) | |
N1B | 1.0407 (8) | 0.2860 (2) | 0.7944 (10) | 0.127 (3) | |
O2B | 0.9497 (11) | 0.2866 (3) | 0.757 (2) | 0.496 (19) | |
O3B | 1.0771 (8) | 0.26701 (18) | 0.7777 (12) | 0.190 (4) | |
N2B | 1.4065 (5) | 0.32976 (13) | 0.9302 (5) | 0.0694 (14) | |
O4B | 1.4442 (4) | 0.30998 (10) | 0.8971 (5) | 0.0795 (13) | |
O5B | 1.4648 (4) | 0.34954 (12) | 0.9721 (6) | 0.0992 (16) | |
N3B | 1.1004 (6) | 0.37430 (16) | 1.0034 (7) | 0.100 (2) | |
O6B | 1.1442 (7) | 0.39547 (14) | 1.0021 (9) | 0.145 (3) | |
O7B | 1.0298 (6) | 0.37010 (14) | 1.0538 (7) | 0.129 (2) | |
C1B | 1.0531 (6) | 0.33102 (15) | 0.8856 (6) | 0.0727 (18) | |
C2B | 1.1069 (6) | 0.30899 (14) | 0.8469 (6) | 0.0689 (17) | |
C3B | 1.2193 (6) | 0.30836 (14) | 0.8624 (6) | 0.0671 (16) | |
H3B | 1.2493 | 0.2936 | 0.8374 | 0.081* | |
C4B | 1.2882 (5) | 0.32998 (13) | 0.9158 (6) | 0.0629 (16) | |
C5B | 1.2460 (6) | 0.35140 (13) | 0.9583 (6) | 0.0652 (16) | |
H5B | 1.2933 | 0.3657 | 0.9954 | 0.078* | |
C6B | 1.1354 (6) | 0.35162 (13) | 0.9461 (6) | 0.0690 (17) | |
Br1B | 0.93986 (11) | 0.469893 (19) | 0.90732 (10) | 0.1229 (4) | |
F1B | 0.5205 (5) | 0.25289 (9) | 0.7106 (6) | 0.1263 (18) | |
F2B | 0.5439 (5) | 0.26596 (10) | 0.5420 (6) | 0.1287 (19) | |
F3B | 0.4042 (5) | 0.24063 (11) | 0.5258 (7) | 0.163 (3) | |
N4B | 0.4554 (6) | 0.39479 (11) | 0.6911 (5) | 0.0798 (16) | |
N5B | 0.4483 (4) | 0.30666 (10) | 0.6281 (5) | 0.0623 (12) | |
N6B | 0.4442 (4) | 0.35129 (10) | 0.6658 (4) | 0.0611 (12) | |
N7B | 0.6682 (4) | 0.32054 (9) | 0.8594 (4) | 0.0548 (11) | |
H7B | 0.5971 | 0.3154 | 0.8525 | 0.066* | |
C7B | 0.3842 (7) | 0.37468 (16) | 0.6515 (6) | 0.079 (2) | |
C8B | 0.2649 (7) | 0.37478 (17) | 0.6049 (8) | 0.092 (2) | |
H8B | 0.2262 | 0.3905 | 0.6008 | 0.110* | |
C9B | 0.2062 (7) | 0.35276 (17) | 0.5667 (7) | 0.089 (2) | |
H9B | 0.1266 | 0.3532 | 0.5348 | 0.106* | |
C10B | 0.2641 (6) | 0.32797 (14) | 0.5737 (6) | 0.0695 (17) | |
C11B | 0.2076 (6) | 0.30424 (16) | 0.5304 (7) | 0.0786 (19) | |
C12B | 0.2724 (7) | 0.28207 (16) | 0.5350 (7) | 0.082 (2) | |
H12B | 0.2374 | 0.2659 | 0.5063 | 0.098* | |
C13B | 0.3897 (7) | 0.28445 (14) | 0.5830 (7) | 0.0745 (18) | |
C14B | 0.3847 (6) | 0.32764 (13) | 0.6210 (6) | 0.0635 (16) | |
C15B | 0.5601 (6) | 0.35774 (12) | 0.7176 (5) | 0.0600 (15) | |
C16B | 0.5639 (6) | 0.38490 (12) | 0.7315 (6) | 0.0683 (17) | |
C17B | 0.0783 (7) | 0.30244 (19) | 0.4755 (8) | 0.109 (3) | |
H17D | 0.0554 | 0.2846 | 0.4502 | 0.163* | |
H17E | 0.0471 | 0.3137 | 0.4002 | 0.163* | |
H17F | 0.0504 | 0.3078 | 0.5413 | 0.163* | |
C18B | 0.4640 (8) | 0.26107 (16) | 0.5876 (10) | 0.098 (2) | |
C19B | 0.6533 (5) | 0.33822 (11) | 0.7437 (6) | 0.0598 (15) | |
H19C | 0.7247 | 0.3475 | 0.7601 | 0.072* | |
H19D | 0.6371 | 0.3274 | 0.6660 | 0.072* | |
C20B | 0.7232 (6) | 0.33453 (12) | 0.9880 (6) | 0.0657 (16) | |
H20C | 0.6780 | 0.3498 | 0.9896 | 0.079* | |
H20D | 0.7991 | 0.3405 | 0.9980 | 0.079* | |
C21B | 0.7321 (6) | 0.31648 (14) | 1.0998 (6) | 0.0786 (19) | |
H21C | 0.7695 | 0.3258 | 1.1820 | 0.094* | |
H21D | 0.6555 | 0.3119 | 1.0931 | 0.094* | |
C22B | 0.7970 (6) | 0.29172 (14) | 1.1033 (8) | 0.087 (2) | |
H22B | 0.8761 | 0.2964 | 1.1175 | 0.105* | |
C23B | 0.7439 (7) | 0.27848 (14) | 0.9713 (8) | 0.091 (2) | |
H23C | 0.7896 | 0.2633 | 0.9698 | 0.109* | |
H23D | 0.6678 | 0.2723 | 0.9595 | 0.109* | |
C24B | 0.7349 (6) | 0.29631 (12) | 0.8589 (8) | 0.0763 (19) | |
H24C | 0.8112 | 0.3012 | 0.8656 | 0.092* | |
H24D | 0.6976 | 0.2870 | 0.7766 | 0.092* | |
C25B | 0.7995 (8) | 0.27346 (19) | 1.2155 (9) | 0.129 (4) | |
H25D | 0.8336 | 0.2825 | 1.2978 | 0.194* | |
H25E | 0.8437 | 0.2581 | 1.2162 | 0.194* | |
H25F | 0.7227 | 0.2684 | 1.2024 | 0.194* | |
C26B | 0.6596 (7) | 0.40423 (13) | 0.7770 (6) | 0.0710 (18) | |
C27B | 0.6337 (8) | 0.43025 (14) | 0.7409 (7) | 0.087 (2) | |
H27B | 0.5586 | 0.4347 | 0.6882 | 0.105* | |
C28B | 0.7154 (10) | 0.44992 (14) | 0.7803 (8) | 0.095 (3) | |
H28B | 0.6955 | 0.4673 | 0.7557 | 0.114* | |
C29B | 0.8261 (9) | 0.44328 (16) | 0.8562 (8) | 0.091 (2) | |
C30B | 0.8547 (7) | 0.41829 (15) | 0.8963 (8) | 0.086 (2) | |
H30B | 0.9296 | 0.4143 | 0.9515 | 0.103* | |
C31B | 0.7730 (7) | 0.39845 (14) | 0.8558 (7) | 0.082 (2) | |
H31B | 0.7941 | 0.3812 | 0.8814 | 0.099* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.055 (3) | 0.133 (4) | 0.090 (3) | −0.012 (3) | 0.036 (3) | −0.020 (3) |
N1A | 0.106 (5) | 0.087 (5) | 0.073 (4) | −0.011 (4) | 0.046 (4) | −0.005 (3) |
O2A | 0.110 (5) | 0.114 (5) | 0.132 (5) | −0.028 (4) | 0.049 (4) | −0.008 (4) |
O3A | 0.153 (6) | 0.075 (4) | 0.137 (5) | 0.013 (4) | 0.051 (5) | 0.016 (4) |
N2A | 0.062 (5) | 0.172 (9) | 0.168 (8) | 0.015 (6) | 0.064 (5) | −0.009 (7) |
O4A | 0.078 (4) | 0.150 (6) | 0.280 (11) | 0.035 (4) | 0.075 (6) | 0.020 (6) |
O5A | 0.092 (5) | 0.191 (8) | 0.290 (12) | −0.025 (5) | 0.123 (7) | −0.030 (8) |
N3A | 0.070 (4) | 0.098 (5) | 0.117 (6) | 0.005 (4) | 0.048 (4) | −0.012 (4) |
O6A | 0.113 (5) | 0.069 (4) | 0.224 (8) | 0.000 (3) | 0.068 (5) | −0.023 (4) |
O7A | 0.095 (4) | 0.115 (5) | 0.134 (5) | 0.028 (4) | 0.039 (4) | 0.007 (4) |
C1A | 0.049 (4) | 0.094 (5) | 0.053 (3) | −0.003 (3) | 0.021 (3) | −0.014 (3) |
C2A | 0.080 (5) | 0.070 (4) | 0.055 (3) | −0.008 (3) | 0.035 (3) | −0.013 (3) |
C3A | 0.074 (5) | 0.088 (5) | 0.077 (5) | 0.016 (4) | 0.037 (4) | 0.000 (4) |
C4A | 0.059 (4) | 0.110 (6) | 0.093 (5) | 0.007 (4) | 0.037 (4) | −0.010 (4) |
C5A | 0.069 (5) | 0.079 (5) | 0.107 (6) | −0.005 (4) | 0.052 (4) | −0.017 (4) |
C6A | 0.055 (4) | 0.082 (5) | 0.068 (4) | 0.003 (3) | 0.029 (3) | −0.015 (3) |
Br1A | 0.1511 (10) | 0.1309 (9) | 0.0762 (6) | −0.0523 (7) | 0.0352 (6) | −0.0022 (5) |
F1A | 0.189 (6) | 0.117 (4) | 0.095 (4) | 0.002 (4) | 0.010 (4) | 0.028 (3) |
F2A | 0.204 (7) | 0.109 (4) | 0.183 (6) | 0.047 (4) | 0.109 (6) | 0.033 (4) |
F3A | 0.159 (5) | 0.095 (4) | 0.170 (6) | −0.027 (4) | 0.035 (4) | −0.007 (4) |
N4A | 0.091 (4) | 0.071 (4) | 0.067 (3) | 0.020 (3) | 0.038 (3) | 0.020 (3) |
N5A | 0.088 (4) | 0.097 (5) | 0.051 (3) | 0.003 (4) | 0.030 (3) | 0.005 (3) |
N6A | 0.076 (4) | 0.074 (4) | 0.053 (3) | 0.006 (3) | 0.031 (3) | 0.007 (3) |
N7A | 0.053 (3) | 0.070 (3) | 0.051 (3) | 0.003 (2) | 0.024 (2) | 0.005 (2) |
C7A | 0.093 (5) | 0.075 (5) | 0.060 (4) | 0.019 (4) | 0.036 (4) | 0.013 (3) |
C8A | 0.087 (6) | 0.102 (6) | 0.065 (4) | 0.028 (5) | 0.023 (4) | 0.008 (4) |
C9A | 0.075 (5) | 0.137 (8) | 0.058 (4) | 0.016 (5) | 0.015 (4) | −0.005 (5) |
C10A | 0.069 (5) | 0.126 (7) | 0.052 (4) | 0.005 (5) | 0.025 (3) | −0.013 (4) |
C11A | 0.087 (6) | 0.104 (6) | 0.072 (5) | −0.007 (5) | 0.026 (4) | −0.022 (4) |
C12A | 0.103 (7) | 0.101 (6) | 0.072 (5) | −0.019 (5) | 0.035 (5) | −0.019 (4) |
C13A | 0.101 (6) | 0.092 (6) | 0.049 (4) | −0.005 (5) | 0.027 (4) | −0.005 (4) |
C14A | 0.084 (5) | 0.089 (5) | 0.051 (4) | 0.009 (4) | 0.036 (3) | 0.008 (3) |
C15A | 0.075 (4) | 0.070 (4) | 0.053 (3) | 0.008 (3) | 0.034 (3) | 0.013 (3) |
C16A | 0.087 (5) | 0.071 (4) | 0.063 (4) | 0.015 (4) | 0.046 (4) | 0.020 (3) |
C17A | 0.090 (7) | 0.120 (7) | 0.152 (9) | −0.009 (5) | 0.022 (6) | −0.046 (7) |
C18A | 0.125 (8) | 0.099 (7) | 0.081 (6) | −0.022 (6) | 0.023 (6) | −0.005 (5) |
C19A | 0.080 (4) | 0.062 (4) | 0.062 (4) | 0.003 (3) | 0.037 (3) | 0.011 (3) |
C20A | 0.089 (5) | 0.055 (4) | 0.063 (4) | −0.001 (3) | 0.025 (3) | 0.003 (3) |
C21A | 0.096 (5) | 0.083 (5) | 0.051 (4) | 0.001 (4) | 0.022 (3) | −0.001 (3) |
C22A | 0.070 (4) | 0.084 (5) | 0.067 (4) | 0.008 (4) | 0.017 (3) | 0.017 (4) |
C23A | 0.081 (5) | 0.073 (4) | 0.074 (4) | 0.019 (4) | 0.029 (4) | 0.022 (4) |
C24A | 0.082 (5) | 0.065 (4) | 0.080 (4) | 0.021 (3) | 0.037 (4) | 0.016 (3) |
C25A | 0.118 (7) | 0.127 (7) | 0.078 (5) | 0.024 (6) | 0.035 (5) | 0.035 (5) |
C26A | 0.084 (5) | 0.073 (4) | 0.057 (4) | 0.009 (4) | 0.035 (3) | 0.017 (3) |
C27A | 0.110 (7) | 0.082 (5) | 0.100 (6) | 0.012 (5) | 0.054 (5) | −0.001 (5) |
C28A | 0.133 (8) | 0.083 (6) | 0.104 (7) | −0.002 (6) | 0.057 (6) | −0.009 (5) |
C29A | 0.120 (7) | 0.086 (6) | 0.065 (4) | −0.015 (5) | 0.038 (5) | 0.009 (4) |
C30A | 0.087 (5) | 0.101 (6) | 0.069 (4) | 0.000 (5) | 0.033 (4) | 0.019 (4) |
C31A | 0.093 (5) | 0.068 (4) | 0.067 (4) | 0.004 (4) | 0.032 (4) | 0.015 (3) |
O1B | 0.059 (3) | 0.117 (4) | 0.122 (4) | 0.007 (3) | 0.040 (3) | 0.017 (3) |
N1B | 0.082 (6) | 0.138 (8) | 0.189 (9) | −0.042 (6) | 0.084 (6) | −0.064 (7) |
O2B | 0.209 (11) | 0.340 (17) | 1.06 (5) | −0.202 (12) | 0.38 (2) | −0.49 (3) |
O3B | 0.133 (7) | 0.120 (6) | 0.302 (13) | −0.018 (5) | 0.068 (8) | −0.046 (7) |
N2B | 0.065 (4) | 0.090 (4) | 0.058 (3) | −0.004 (3) | 0.027 (3) | 0.012 (3) |
O4B | 0.074 (3) | 0.094 (4) | 0.081 (3) | 0.007 (3) | 0.041 (3) | 0.007 (3) |
O5B | 0.069 (3) | 0.110 (4) | 0.120 (4) | −0.020 (3) | 0.038 (3) | −0.004 (3) |
N3B | 0.091 (5) | 0.099 (6) | 0.115 (6) | 0.021 (4) | 0.048 (4) | −0.002 (4) |
O6B | 0.148 (6) | 0.080 (4) | 0.227 (9) | −0.001 (4) | 0.093 (6) | −0.021 (5) |
O7B | 0.122 (5) | 0.151 (6) | 0.138 (6) | 0.026 (4) | 0.076 (5) | −0.016 (4) |
C1B | 0.059 (4) | 0.096 (5) | 0.066 (4) | 0.010 (4) | 0.028 (3) | 0.024 (4) |
C2B | 0.060 (4) | 0.079 (4) | 0.070 (4) | −0.011 (3) | 0.027 (3) | 0.001 (3) |
C3B | 0.068 (4) | 0.080 (4) | 0.061 (4) | 0.001 (3) | 0.032 (3) | 0.008 (3) |
C4B | 0.052 (4) | 0.085 (5) | 0.053 (3) | −0.003 (3) | 0.022 (3) | 0.012 (3) |
C5B | 0.062 (4) | 0.068 (4) | 0.063 (4) | −0.002 (3) | 0.021 (3) | 0.006 (3) |
C6B | 0.077 (5) | 0.066 (4) | 0.065 (4) | 0.008 (3) | 0.029 (3) | 0.013 (3) |
Br1B | 0.1919 (11) | 0.0972 (7) | 0.1045 (7) | −0.0646 (7) | 0.0844 (7) | −0.0289 (5) |
F1B | 0.133 (4) | 0.088 (3) | 0.136 (5) | 0.010 (3) | 0.027 (4) | 0.022 (3) |
F2B | 0.158 (5) | 0.096 (3) | 0.168 (5) | 0.017 (3) | 0.102 (4) | −0.005 (3) |
F3B | 0.139 (5) | 0.105 (4) | 0.201 (7) | −0.013 (4) | 0.017 (4) | −0.067 (4) |
N4B | 0.102 (5) | 0.066 (4) | 0.067 (3) | 0.021 (3) | 0.028 (3) | −0.006 (3) |
N5B | 0.068 (3) | 0.059 (3) | 0.059 (3) | 0.002 (3) | 0.024 (3) | 0.004 (2) |
N6B | 0.062 (3) | 0.071 (3) | 0.049 (3) | 0.008 (3) | 0.020 (2) | −0.002 (2) |
N7B | 0.048 (3) | 0.053 (3) | 0.065 (3) | 0.002 (2) | 0.024 (2) | 0.007 (2) |
C7B | 0.085 (5) | 0.089 (5) | 0.056 (4) | 0.026 (4) | 0.021 (4) | −0.002 (4) |
C8B | 0.082 (6) | 0.098 (6) | 0.084 (5) | 0.033 (5) | 0.020 (4) | −0.011 (4) |
C9B | 0.075 (5) | 0.105 (6) | 0.082 (5) | 0.020 (5) | 0.025 (4) | −0.012 (4) |
C10B | 0.069 (4) | 0.084 (5) | 0.052 (3) | 0.001 (4) | 0.018 (3) | −0.002 (3) |
C11B | 0.073 (5) | 0.100 (6) | 0.064 (4) | −0.011 (4) | 0.028 (4) | −0.004 (4) |
C12B | 0.081 (5) | 0.089 (5) | 0.069 (4) | −0.019 (4) | 0.022 (4) | −0.005 (4) |
C13B | 0.086 (5) | 0.073 (5) | 0.066 (4) | −0.004 (4) | 0.030 (4) | 0.003 (3) |
C14B | 0.066 (4) | 0.078 (4) | 0.047 (3) | 0.000 (3) | 0.021 (3) | −0.001 (3) |
C15B | 0.074 (4) | 0.062 (4) | 0.049 (3) | 0.001 (3) | 0.030 (3) | 0.002 (3) |
C16B | 0.099 (5) | 0.059 (4) | 0.051 (3) | 0.010 (4) | 0.033 (3) | 0.001 (3) |
C17B | 0.078 (6) | 0.146 (8) | 0.097 (6) | −0.023 (5) | 0.028 (5) | −0.009 (6) |
C18B | 0.101 (7) | 0.071 (5) | 0.109 (7) | −0.010 (5) | 0.026 (6) | −0.004 (5) |
C19B | 0.066 (4) | 0.058 (3) | 0.064 (4) | −0.006 (3) | 0.035 (3) | −0.002 (3) |
C20B | 0.066 (4) | 0.062 (4) | 0.068 (4) | −0.001 (3) | 0.023 (3) | 0.006 (3) |
C21B | 0.072 (4) | 0.090 (5) | 0.062 (4) | −0.010 (4) | 0.013 (3) | 0.016 (4) |
C22B | 0.060 (4) | 0.078 (5) | 0.104 (6) | −0.002 (4) | 0.010 (4) | 0.029 (4) |
C23B | 0.081 (5) | 0.068 (4) | 0.119 (7) | 0.011 (4) | 0.033 (5) | 0.018 (4) |
C24B | 0.066 (4) | 0.061 (4) | 0.107 (6) | 0.002 (3) | 0.040 (4) | 0.002 (4) |
C25B | 0.116 (7) | 0.125 (8) | 0.116 (7) | −0.004 (6) | 0.010 (6) | 0.050 (6) |
C26B | 0.105 (6) | 0.060 (4) | 0.056 (4) | −0.001 (4) | 0.040 (4) | −0.002 (3) |
C27B | 0.129 (7) | 0.069 (5) | 0.074 (5) | 0.008 (5) | 0.051 (5) | 0.002 (4) |
C28B | 0.162 (9) | 0.051 (4) | 0.089 (6) | 0.003 (5) | 0.067 (6) | −0.001 (4) |
C29B | 0.142 (8) | 0.072 (5) | 0.080 (5) | −0.018 (5) | 0.066 (6) | −0.007 (4) |
C30B | 0.101 (6) | 0.075 (5) | 0.086 (5) | −0.017 (4) | 0.041 (4) | −0.008 (4) |
C31B | 0.099 (6) | 0.065 (4) | 0.081 (5) | −0.006 (4) | 0.032 (4) | 0.003 (4) |
Geometric parameters (Å, º) top
O1A—C1A | 1.235 (7) | O1B—C1B | 1.230 (7) |
N1A—O3A | 1.208 (8) | N1B—O2B | 1.063 (14) |
N1A—O2A | 1.227 (8) | N1B—O3B | 1.114 (10) |
N1A—C2A | 1.465 (9) | N1B—C2B | 1.426 (10) |
N2A—O5A | 1.204 (11) | N2B—O4B | 1.227 (7) |
N2A—O4A | 1.239 (10) | N2B—O5B | 1.228 (7) |
N2A—C4A | 1.437 (10) | N2B—C4B | 1.440 (8) |
N3A—O7A | 1.211 (8) | N3B—O6B | 1.213 (9) |
N3A—O6A | 1.244 (8) | N3B—O7B | 1.236 (9) |
N3A—C6A | 1.427 (9) | N3B—C6B | 1.462 (9) |
C1A—C2A | 1.443 (9) | C1B—C6B | 1.447 (10) |
C1A—C6A | 1.453 (9) | C1B—C2B | 1.456 (9) |
C2A—C3A | 1.366 (9) | C2B—C3B | 1.364 (9) |
C3A—C4A | 1.375 (10) | C3B—C4B | 1.387 (9) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.389 (10) | C4B—C5B | 1.372 (9) |
C5A—C6A | 1.352 (9) | C5B—C6B | 1.351 (9) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
Br1A—C29A | 1.896 (9) | Br1B—C29B | 1.896 (8) |
F1A—C18A | 1.327 (10) | F1B—C18B | 1.333 (10) |
F2A—C18A | 1.325 (11) | F2B—C18B | 1.311 (10) |
F3A—C18A | 1.324 (10) | F3B—C18B | 1.312 (9) |
N4A—C7A | 1.321 (9) | N4B—C7B | 1.321 (9) |
N4A—C16A | 1.369 (8) | N4B—C16B | 1.365 (9) |
N5A—C14A | 1.311 (8) | N5B—C14B | 1.320 (8) |
N5A—C13A | 1.345 (9) | N5B—C13B | 1.338 (8) |
N6A—C7A | 1.379 (8) | N6B—C7B | 1.386 (8) |
N6A—C15A | 1.385 (8) | N6B—C15B | 1.392 (8) |
N6A—C14A | 1.430 (9) | N6B—C14B | 1.404 (8) |
N7A—C20A | 1.485 (7) | N7B—C24B | 1.495 (7) |
N7A—C24A | 1.488 (7) | N7B—C20B | 1.498 (7) |
N7A—C19A | 1.513 (7) | N7B—C19B | 1.512 (7) |
N7A—H7A | 0.9100 | N7B—H7B | 0.9100 |
C7A—C8A | 1.412 (10) | C7B—C8B | 1.395 (11) |
C8A—C9A | 1.305 (11) | C8B—C9B | 1.320 (11) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—C10A | 1.445 (11) | C9B—C10B | 1.445 (10) |
C9A—H9A | 0.9300 | C9B—H9B | 0.9300 |
C10A—C11A | 1.389 (11) | C10B—C11B | 1.391 (9) |
C10A—C14A | 1.400 (10) | C10B—C14B | 1.409 (9) |
C11A—C12A | 1.370 (11) | C11B—C12B | 1.383 (10) |
C11A—C17A | 1.505 (11) | C11B—C17B | 1.511 (10) |
C12A—C13A | 1.368 (11) | C12B—C13B | 1.375 (10) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—C18A | 1.493 (12) | C13B—C18B | 1.505 (11) |
C15A—C16A | 1.378 (9) | C15B—C16B | 1.389 (8) |
C15A—C19A | 1.495 (8) | C15B—C19B | 1.483 (8) |
C16A—C26A | 1.466 (10) | C16B—C26B | 1.489 (10) |
C17A—H17A | 0.9600 | C17B—H17D | 0.9600 |
C17A—H17B | 0.9600 | C17B—H17E | 0.9600 |
C17A—H17C | 0.9600 | C17B—H17F | 0.9600 |
C19A—H19A | 0.9700 | C19B—H19C | 0.9700 |
C19A—H19B | 0.9700 | C19B—H19D | 0.9700 |
C20A—C21A | 1.516 (9) | C20B—C21B | 1.506 (8) |
C20A—H20A | 0.9700 | C20B—H20C | 0.9700 |
C20A—H20B | 0.9700 | C20B—H20D | 0.9700 |
C21A—C22A | 1.534 (9) | C21B—C22B | 1.495 (10) |
C21A—H21A | 0.9700 | C21B—H21C | 0.9700 |
C21A—H21B | 0.9700 | C21B—H21D | 0.9700 |
C22A—C23A | 1.498 (10) | C22B—C23B | 1.508 (11) |
C22A—C25A | 1.505 (10) | C22B—C25B | 1.537 (11) |
C22A—H22A | 0.9800 | C22B—H22B | 0.9800 |
C23A—C24A | 1.515 (9) | C23B—C24B | 1.504 (10) |
C23A—H23A | 0.9700 | C23B—H23C | 0.9700 |
C23A—H23B | 0.9700 | C23B—H23D | 0.9700 |
C24A—H24A | 0.9700 | C24B—H24C | 0.9700 |
C24A—H24B | 0.9700 | C24B—H24D | 0.9700 |
C25A—H25A | 0.9600 | C25B—H25D | 0.9600 |
C25A—H25B | 0.9600 | C25B—H25E | 0.9600 |
C25A—H25C | 0.9600 | C25B—H25F | 0.9600 |
C26A—C31A | 1.390 (9) | C26B—C27B | 1.385 (9) |
C26A—C27A | 1.394 (10) | C26B—C31B | 1.392 (10) |
C27A—C28A | 1.378 (12) | C27B—C28B | 1.382 (11) |
C27A—H27A | 0.9300 | C27B—H27B | 0.9300 |
C28A—C29A | 1.363 (12) | C28B—C29B | 1.369 (12) |
C28A—H28A | 0.9300 | C28B—H28B | 0.9300 |
C29A—C30A | 1.362 (11) | C29B—C30B | 1.349 (11) |
C30A—C31A | 1.388 (10) | C30B—C31B | 1.390 (10) |
C30A—H30A | 0.9300 | C30B—H30B | 0.9300 |
C31A—H31A | 0.9300 | C31B—H31B | 0.9300 |
| | | |
O3A—N1A—O2A | 122.6 (8) | O2B—N1B—O3B | 114.4 (11) |
O3A—N1A—C2A | 119.2 (7) | O2B—N1B—C2B | 120.9 (11) |
O2A—N1A—C2A | 118.1 (7) | O3B—N1B—C2B | 124.3 (9) |
O5A—N2A—O4A | 122.0 (8) | O4B—N2B—O5B | 122.6 (6) |
O5A—N2A—C4A | 120.7 (10) | O4B—N2B—C4B | 118.5 (6) |
O4A—N2A—C4A | 117.2 (10) | O5B—N2B—C4B | 118.8 (6) |
O7A—N3A—O6A | 122.0 (8) | O6B—N3B—O7B | 124.7 (8) |
O7A—N3A—C6A | 119.9 (7) | O6B—N3B—C6B | 118.8 (8) |
O6A—N3A—C6A | 118.1 (7) | O7B—N3B—C6B | 116.5 (8) |
O1A—C1A—C2A | 125.1 (7) | O1B—C1B—C6B | 124.8 (7) |
O1A—C1A—C6A | 123.3 (6) | O1B—C1B—C2B | 124.1 (7) |
C2A—C1A—C6A | 111.5 (5) | C6B—C1B—C2B | 111.0 (6) |
C3A—C2A—C1A | 124.5 (6) | C3B—C2B—N1B | 116.9 (7) |
C3A—C2A—N1A | 115.1 (7) | C3B—C2B—C1B | 124.1 (6) |
C1A—C2A—N1A | 120.4 (6) | N1B—C2B—C1B | 119.0 (6) |
C2A—C3A—C4A | 118.8 (7) | C2B—C3B—C4B | 119.3 (6) |
C2A—C3A—H3A | 120.6 | C2B—C3B—H3B | 120.4 |
C4A—C3A—H3A | 120.6 | C4B—C3B—H3B | 120.4 |
C3A—C4A—C5A | 121.6 (7) | C5B—C4B—C3B | 120.8 (6) |
C3A—C4A—N2A | 120.0 (8) | C5B—C4B—N2B | 119.4 (6) |
C5A—C4A—N2A | 118.4 (8) | C3B—C4B—N2B | 119.8 (6) |
C6A—C5A—C4A | 118.8 (7) | C6B—C5B—C4B | 119.6 (6) |
C6A—C5A—H5A | 120.6 | C6B—C5B—H5B | 120.2 |
C4A—C5A—H5A | 120.6 | C4B—C5B—H5B | 120.2 |
C5A—C6A—N3A | 117.3 (7) | C5B—C6B—C1B | 125.0 (6) |
C5A—C6A—C1A | 124.5 (7) | C5B—C6B—N3B | 115.8 (7) |
N3A—C6A—C1A | 118.2 (6) | C1B—C6B—N3B | 119.2 (7) |
C7A—N4A—C16A | 106.2 (6) | C7B—N4B—C16B | 107.1 (6) |
C14A—N5A—C13A | 113.9 (7) | C14B—N5B—C13B | 115.0 (6) |
C7A—N6A—C15A | 106.8 (6) | C7B—N6B—C15B | 106.7 (6) |
C7A—N6A—C14A | 120.8 (6) | C7B—N6B—C14B | 120.0 (6) |
C15A—N6A—C14A | 132.4 (6) | C15B—N6B—C14B | 133.1 (5) |
C20A—N7A—C24A | 110.5 (5) | C24B—N7B—C20B | 109.7 (5) |
C20A—N7A—C19A | 111.3 (5) | C24B—N7B—C19B | 112.0 (5) |
C24A—N7A—C19A | 109.6 (4) | C20B—N7B—C19B | 112.2 (4) |
C20A—N7A—H7A | 108.5 | C24B—N7B—H7B | 107.5 |
C24A—N7A—H7A | 108.4 | C20B—N7B—H7B | 107.5 |
C19A—N7A—H7A | 108.4 | C19B—N7B—H7B | 107.5 |
N4A—C7A—N6A | 111.1 (6) | N4B—C7B—N6B | 110.8 (6) |
N4A—C7A—C8A | 129.6 (7) | N4B—C7B—C8B | 128.4 (7) |
N6A—C7A—C8A | 119.4 (8) | N6B—C7B—C8B | 120.8 (8) |
C9A—C8A—C7A | 121.9 (8) | C9B—C8B—C7B | 120.6 (7) |
C9A—C8A—H8A | 119.1 | C9B—C8B—H8B | 119.7 |
C7A—C8A—H8A | 119.1 | C7B—C8B—H8B | 119.7 |
C8A—C9A—C10A | 120.6 (8) | C8B—C9B—C10B | 120.9 (7) |
C8A—C9A—H9A | 119.7 | C8B—C9B—H9B | 119.6 |
C10A—C9A—H9A | 119.7 | C10B—C9B—H9B | 119.6 |
C11A—C10A—C14A | 117.2 (8) | C11B—C10B—C14B | 117.2 (7) |
C11A—C10A—C9A | 123.2 (8) | C11B—C10B—C9B | 123.8 (7) |
C14A—C10A—C9A | 119.6 (8) | C14B—C10B—C9B | 118.9 (7) |
C12A—C11A—C10A | 117.2 (8) | C12B—C11B—C10B | 118.4 (7) |
C12A—C11A—C17A | 120.3 (8) | C12B—C11B—C17B | 119.9 (7) |
C10A—C11A—C17A | 122.5 (8) | C10B—C11B—C17B | 121.6 (8) |
C13A—C12A—C11A | 120.4 (8) | C13B—C12B—C11B | 118.5 (7) |
C13A—C12A—H12A | 119.8 | C13B—C12B—H12B | 120.7 |
C11A—C12A—H12A | 119.8 | C11B—C12B—H12B | 120.7 |
N5A—C13A—C12A | 124.6 (8) | N5B—C13B—C12B | 125.4 (7) |
N5A—C13A—C18A | 113.2 (8) | N5B—C13B—C18B | 113.9 (7) |
C12A—C13A—C18A | 122.2 (8) | C12B—C13B—C18B | 120.7 (7) |
N5A—C14A—C10A | 126.7 (8) | N5B—C14B—N6B | 116.1 (6) |
N5A—C14A—N6A | 115.6 (7) | N5B—C14B—C10B | 125.4 (6) |
C10A—C14A—N6A | 117.7 (7) | N6B—C14B—C10B | 118.5 (6) |
C16A—C15A—N6A | 105.5 (6) | C16B—C15B—N6B | 105.5 (6) |
C16A—C15A—C19A | 131.0 (6) | C16B—C15B—C19B | 130.8 (6) |
N6A—C15A—C19A | 123.5 (6) | N6B—C15B—C19B | 123.7 (5) |
N4A—C16A—C15A | 110.4 (7) | N4B—C16B—C15B | 110.0 (6) |
N4A—C16A—C26A | 117.7 (6) | N4B—C16B—C26B | 116.8 (6) |
C15A—C16A—C26A | 131.8 (6) | C15B—C16B—C26B | 133.1 (7) |
C11A—C17A—H17A | 109.5 | C11B—C17B—H17D | 109.5 |
C11A—C17A—H17B | 109.5 | C11B—C17B—H17E | 109.5 |
H17A—C17A—H17B | 109.5 | H17D—C17B—H17E | 109.5 |
C11A—C17A—H17C | 109.5 | C11B—C17B—H17F | 109.5 |
H17A—C17A—H17C | 109.5 | H17D—C17B—H17F | 109.5 |
H17B—C17A—H17C | 109.5 | H17E—C17B—H17F | 109.5 |
F3A—C18A—F2A | 106.3 (9) | F2B—C18B—F3B | 109.0 (9) |
F3A—C18A—F1A | 104.5 (8) | F2B—C18B—F1B | 105.0 (8) |
F2A—C18A—F1A | 104.3 (9) | F3B—C18B—F1B | 105.0 (7) |
F3A—C18A—C13A | 114.2 (9) | F2B—C18B—C13B | 113.5 (7) |
F2A—C18A—C13A | 114.0 (8) | F3B—C18B—C13B | 112.4 (8) |
F1A—C18A—C13A | 112.6 (8) | F1B—C18B—C13B | 111.4 (8) |
C15A—C19A—N7A | 113.9 (5) | C15B—C19B—N7B | 113.3 (4) |
C15A—C19A—H19A | 108.8 | C15B—C19B—H19C | 108.9 |
N7A—C19A—H19A | 108.8 | N7B—C19B—H19C | 108.9 |
C15A—C19A—H19B | 108.8 | C15B—C19B—H19D | 108.9 |
N7A—C19A—H19B | 108.8 | N7B—C19B—H19D | 108.9 |
H19A—C19A—H19B | 107.7 | H19C—C19B—H19D | 107.7 |
N7A—C20A—C21A | 110.7 (5) | N7B—C20B—C21B | 110.3 (5) |
N7A—C20A—H20A | 109.5 | N7B—C20B—H20C | 109.6 |
C21A—C20A—H20A | 109.5 | C21B—C20B—H20C | 109.6 |
N7A—C20A—H20B | 109.5 | N7B—C20B—H20D | 109.6 |
C21A—C20A—H20B | 109.5 | C21B—C20B—H20D | 109.6 |
H20A—C20A—H20B | 108.1 | H20C—C20B—H20D | 108.1 |
C20A—C21A—C22A | 112.0 (6) | C22B—C21B—C20B | 113.8 (6) |
C20A—C21A—H21A | 109.2 | C22B—C21B—H21C | 108.8 |
C22A—C21A—H21A | 109.2 | C20B—C21B—H21C | 108.8 |
C20A—C21A—H21B | 109.2 | C22B—C21B—H21D | 108.8 |
C22A—C21A—H21B | 109.2 | C20B—C21B—H21D | 108.8 |
H21A—C21A—H21B | 107.9 | H21C—C21B—H21D | 107.7 |
C23A—C22A—C25A | 112.2 (6) | C21B—C22B—C23B | 108.3 (6) |
C23A—C22A—C21A | 109.0 (5) | C21B—C22B—C25B | 111.9 (8) |
C25A—C22A—C21A | 110.7 (6) | C23B—C22B—C25B | 111.7 (7) |
C23A—C22A—H22A | 108.3 | C21B—C22B—H22B | 108.3 |
C25A—C22A—H22A | 108.3 | C23B—C22B—H22B | 108.3 |
C21A—C22A—H22A | 108.3 | C25B—C22B—H22B | 108.3 |
C22A—C23A—C24A | 111.3 (6) | C24B—C23B—C22B | 113.0 (6) |
C22A—C23A—H23A | 109.4 | C24B—C23B—H23C | 109.0 |
C24A—C23A—H23A | 109.4 | C22B—C23B—H23C | 109.0 |
C22A—C23A—H23B | 109.4 | C24B—C23B—H23D | 109.0 |
C24A—C23A—H23B | 109.4 | C22B—C23B—H23D | 109.0 |
H23A—C23A—H23B | 108.0 | H23C—C23B—H23D | 107.8 |
N7A—C24A—C23A | 111.9 (5) | N7B—C24B—C23B | 111.0 (6) |
N7A—C24A—H24A | 109.2 | N7B—C24B—H24C | 109.4 |
C23A—C24A—H24A | 109.2 | C23B—C24B—H24C | 109.4 |
N7A—C24A—H24B | 109.2 | N7B—C24B—H24D | 109.4 |
C23A—C24A—H24B | 109.2 | C23B—C24B—H24D | 109.4 |
H24A—C24A—H24B | 107.9 | H24C—C24B—H24D | 108.0 |
C22A—C25A—H25A | 109.5 | C22B—C25B—H25D | 109.5 |
C22A—C25A—H25B | 109.5 | C22B—C25B—H25E | 109.5 |
H25A—C25A—H25B | 109.5 | H25D—C25B—H25E | 109.5 |
C22A—C25A—H25C | 109.5 | C22B—C25B—H25F | 109.5 |
H25A—C25A—H25C | 109.5 | H25D—C25B—H25F | 109.5 |
H25B—C25A—H25C | 109.5 | H25E—C25B—H25F | 109.5 |
C31A—C26A—C27A | 117.2 (7) | C27B—C26B—C31B | 117.0 (7) |
C31A—C26A—C16A | 124.3 (6) | C27B—C26B—C16B | 117.6 (7) |
C27A—C26A—C16A | 118.5 (7) | C31B—C26B—C16B | 125.4 (6) |
C28A—C27A—C26A | 121.6 (8) | C28B—C27B—C26B | 122.4 (8) |
C28A—C27A—H27A | 119.2 | C28B—C27B—H27B | 118.8 |
C26A—C27A—H27A | 119.2 | C26B—C27B—H27B | 118.8 |
C29A—C28A—C27A | 120.0 (8) | C29B—C28B—C27B | 118.6 (7) |
C29A—C28A—H28A | 120.0 | C29B—C28B—H28B | 120.7 |
C27A—C28A—H28A | 120.0 | C27B—C28B—H28B | 120.7 |
C30A—C29A—C28A | 120.0 (8) | C30B—C29B—C28B | 121.0 (8) |
C30A—C29A—Br1A | 120.2 (7) | C30B—C29B—Br1B | 119.9 (8) |
C28A—C29A—Br1A | 119.8 (7) | C28B—C29B—Br1B | 119.1 (7) |
C29A—C30A—C31A | 120.7 (8) | C29B—C30B—C31B | 120.4 (8) |
C29A—C30A—H30A | 119.7 | C29B—C30B—H30B | 119.8 |
C31A—C30A—H30A | 119.7 | C31B—C30B—H30B | 119.8 |
C30A—C31A—C26A | 120.5 (7) | C30B—C31B—C26B | 120.5 (7) |
C30A—C31A—H31A | 119.7 | C30B—C31B—H31B | 119.8 |
C26A—C31A—H31A | 119.7 | C26B—C31B—H31B | 119.8 |
| | | |
O1A—C1A—C2A—C3A | 173.1 (6) | O2B—N1B—C2B—C3B | −164.0 (18) |
C6A—C1A—C2A—C3A | −4.8 (8) | O3B—N1B—C2B—C3B | 8.2 (17) |
O1A—C1A—C2A—N1A | −7.3 (9) | O2B—N1B—C2B—C1B | 19 (2) |
C6A—C1A—C2A—N1A | 174.8 (5) | O3B—N1B—C2B—C1B | −169.3 (12) |
O3A—N1A—C2A—C3A | −13.2 (9) | O1B—C1B—C2B—C3B | 176.1 (7) |
O2A—N1A—C2A—C3A | 166.3 (6) | C6B—C1B—C2B—C3B | −1.8 (9) |
O3A—N1A—C2A—C1A | 167.2 (6) | O1B—C1B—C2B—N1B | −6.6 (11) |
O2A—N1A—C2A—C1A | −13.4 (9) | C6B—C1B—C2B—N1B | 175.4 (7) |
C1A—C2A—C3A—C4A | 0.5 (10) | N1B—C2B—C3B—C4B | −178.6 (7) |
N1A—C2A—C3A—C4A | −179.2 (6) | C1B—C2B—C3B—C4B | −1.3 (10) |
C2A—C3A—C4A—C5A | 3.2 (11) | C2B—C3B—C4B—C5B | 2.9 (9) |
C2A—C3A—C4A—N2A | 179.6 (7) | C2B—C3B—C4B—N2B | −178.7 (5) |
O5A—N2A—C4A—C3A | −173.1 (10) | O4B—N2B—C4B—C5B | 176.8 (5) |
O4A—N2A—C4A—C3A | 4.2 (13) | O5B—N2B—C4B—C5B | −4.8 (8) |
O5A—N2A—C4A—C5A | 3.3 (14) | O4B—N2B—C4B—C3B | −1.7 (8) |
O4A—N2A—C4A—C5A | −179.3 (9) | O5B—N2B—C4B—C3B | 176.7 (6) |
C3A—C4A—C5A—C6A | −1.9 (11) | C3B—C4B—C5B—C6B | −1.0 (9) |
N2A—C4A—C5A—C6A | −178.3 (7) | N2B—C4B—C5B—C6B | −179.5 (5) |
C4A—C5A—C6A—N3A | 175.7 (7) | C4B—C5B—C6B—C1B | −2.5 (10) |
C4A—C5A—C6A—C1A | −3.3 (11) | C4B—C5B—C6B—N3B | 175.3 (6) |
O7A—N3A—C6A—C5A | −140.5 (7) | O1B—C1B—C6B—C5B | −174.2 (7) |
O6A—N3A—C6A—C5A | 37.6 (10) | C2B—C1B—C6B—C5B | 3.8 (9) |
O7A—N3A—C6A—C1A | 38.5 (10) | O1B—C1B—C6B—N3B | 8.0 (10) |
O6A—N3A—C6A—C1A | −143.4 (7) | C2B—C1B—C6B—N3B | −174.0 (6) |
O1A—C1A—C6A—C5A | −171.7 (7) | O6B—N3B—C6B—C5B | 33.3 (10) |
C2A—C1A—C6A—C5A | 6.3 (9) | O7B—N3B—C6B—C5B | −144.4 (7) |
O1A—C1A—C6A—N3A | 9.3 (9) | O6B—N3B—C6B—C1B | −148.7 (8) |
C2A—C1A—C6A—N3A | −172.7 (6) | O7B—N3B—C6B—C1B | 33.5 (10) |
C16A—N4A—C7A—N6A | 0.3 (7) | C16B—N4B—C7B—N6B | 0.5 (7) |
C16A—N4A—C7A—C8A | −179.9 (7) | C16B—N4B—C7B—C8B | 178.2 (7) |
C15A—N6A—C7A—N4A | −0.4 (7) | C15B—N6B—C7B—N4B | −0.2 (7) |
C14A—N6A—C7A—N4A | 178.6 (5) | C14B—N6B—C7B—N4B | −175.7 (5) |
C15A—N6A—C7A—C8A | 179.8 (6) | C15B—N6B—C7B—C8B | −178.1 (6) |
C14A—N6A—C7A—C8A | −1.3 (9) | C14B—N6B—C7B—C8B | 6.4 (9) |
N4A—C7A—C8A—C9A | −179.2 (7) | N4B—C7B—C8B—C9B | 178.7 (8) |
N6A—C7A—C8A—C9A | 0.6 (11) | N6B—C7B—C8B—C9B | −3.8 (12) |
C7A—C8A—C9A—C10A | 1.6 (11) | C7B—C8B—C9B—C10B | 0.9 (12) |
C8A—C9A—C10A—C11A | 177.3 (7) | C8B—C9B—C10B—C11B | −177.4 (7) |
C8A—C9A—C10A—C14A | −3.1 (10) | C8B—C9B—C10B—C14B | −0.6 (11) |
C14A—C10A—C11A—C12A | −0.8 (10) | C14B—C10B—C11B—C12B | −0.7 (9) |
C9A—C10A—C11A—C12A | 178.8 (7) | C9B—C10B—C11B—C12B | 176.2 (7) |
C14A—C10A—C11A—C17A | −179.7 (7) | C14B—C10B—C11B—C17B | −178.9 (6) |
C9A—C10A—C11A—C17A | −0.1 (12) | C9B—C10B—C11B—C17B | −2.0 (11) |
C10A—C11A—C12A—C13A | 0.3 (11) | C10B—C11B—C12B—C13B | 0.5 (10) |
C17A—C11A—C12A—C13A | 179.2 (8) | C17B—C11B—C12B—C13B | 178.7 (7) |
C14A—N5A—C13A—C12A | 0.1 (10) | C14B—N5B—C13B—C12B | −1.8 (9) |
C14A—N5A—C13A—C18A | 178.1 (6) | C14B—N5B—C13B—C18B | 177.9 (6) |
C11A—C12A—C13A—N5A | 0.1 (11) | C11B—C12B—C13B—N5B | 0.8 (11) |
C11A—C12A—C13A—C18A | −177.7 (8) | C11B—C12B—C13B—C18B | −178.8 (7) |
C13A—N5A—C14A—C10A | −0.7 (9) | C13B—N5B—C14B—N6B | −179.0 (5) |
C13A—N5A—C14A—N6A | 178.5 (5) | C13B—N5B—C14B—C10B | 1.4 (9) |
C11A—C10A—C14A—N5A | 1.1 (10) | C7B—N6B—C14B—N5B | 174.4 (5) |
C9A—C10A—C14A—N5A | −178.5 (6) | C15B—N6B—C14B—N5B | 0.3 (9) |
C11A—C10A—C14A—N6A | −178.1 (6) | C7B—N6B—C14B—C10B | −6.1 (8) |
C9A—C10A—C14A—N6A | 2.3 (9) | C15B—N6B—C14B—C10B | 179.9 (6) |
C7A—N6A—C14A—N5A | −179.5 (5) | C11B—C10B—C14B—N5B | −0.3 (9) |
C15A—N6A—C14A—N5A | −0.9 (9) | C9B—C10B—C14B—N5B | −177.3 (6) |
C7A—N6A—C14A—C10A | −0.2 (8) | C11B—C10B—C14B—N6B | −179.8 (5) |
C15A—N6A—C14A—C10A | 178.4 (6) | C9B—C10B—C14B—N6B | 3.2 (9) |
C7A—N6A—C15A—C16A | 0.2 (6) | C7B—N6B—C15B—C16B | −0.2 (6) |
C14A—N6A—C15A—C16A | −178.5 (6) | C14B—N6B—C15B—C16B | 174.5 (6) |
C7A—N6A—C15A—C19A | −178.5 (5) | C7B—N6B—C15B—C19B | −177.9 (5) |
C14A—N6A—C15A—C19A | 2.8 (9) | C14B—N6B—C15B—C19B | −3.3 (9) |
C7A—N4A—C16A—C15A | −0.2 (7) | C7B—N4B—C16B—C15B | −0.6 (7) |
C7A—N4A—C16A—C26A | −178.6 (5) | C7B—N4B—C16B—C26B | 178.1 (5) |
N6A—C15A—C16A—N4A | 0.0 (6) | N6B—C15B—C16B—N4B | 0.5 (6) |
C19A—C15A—C16A—N4A | 178.5 (6) | C19B—C15B—C16B—N4B | 178.0 (6) |
N6A—C15A—C16A—C26A | 178.1 (6) | N6B—C15B—C16B—C26B | −177.9 (6) |
C19A—C15A—C16A—C26A | −3.3 (11) | C19B—C15B—C16B—C26B | −0.4 (11) |
N5A—C13A—C18A—F3A | 177.4 (7) | N5B—C13B—C18B—F2B | −46.5 (10) |
C12A—C13A—C18A—F3A | −4.6 (12) | C12B—C13B—C18B—F2B | 133.2 (8) |
N5A—C13A—C18A—F2A | −60.2 (10) | N5B—C13B—C18B—F3B | −170.7 (7) |
C12A—C13A—C18A—F2A | 117.9 (9) | C12B—C13B—C18B—F3B | 8.9 (12) |
N5A—C13A—C18A—F1A | 58.4 (11) | N5B—C13B—C18B—F1B | 71.8 (9) |
C12A—C13A—C18A—F1A | −123.5 (9) | C12B—C13B—C18B—F1B | −108.6 (8) |
C16A—C15A—C19A—N7A | 103.2 (7) | C16B—C15B—C19B—N7B | 111.3 (7) |
N6A—C15A—C19A—N7A | −78.4 (7) | N6B—C15B—C19B—N7B | −71.6 (7) |
C20A—N7A—C19A—C15A | −68.4 (7) | C24B—N7B—C19B—C15B | 162.3 (5) |
C24A—N7A—C19A—C15A | 169.0 (6) | C20B—N7B—C19B—C15B | −73.8 (6) |
C24A—N7A—C20A—C21A | −56.5 (7) | C24B—N7B—C20B—C21B | −56.9 (6) |
C19A—N7A—C20A—C21A | −178.5 (5) | C19B—N7B—C20B—C21B | 177.9 (5) |
N7A—C20A—C21A—C22A | 56.7 (8) | N7B—C20B—C21B—C22B | 57.2 (7) |
C20A—C21A—C22A—C23A | −55.4 (8) | C20B—C21B—C22B—C23B | −54.0 (8) |
C20A—C21A—C22A—C25A | −179.3 (7) | C20B—C21B—C22B—C25B | −177.6 (6) |
C25A—C22A—C23A—C24A | 177.9 (6) | C21B—C22B—C23B—C24B | 53.5 (8) |
C21A—C22A—C23A—C24A | 55.0 (8) | C25B—C22B—C23B—C24B | 177.2 (7) |
C20A—N7A—C24A—C23A | 57.1 (7) | C20B—N7B—C24B—C23B | 57.3 (7) |
C19A—N7A—C24A—C23A | −179.9 (6) | C19B—N7B—C24B—C23B | −177.4 (6) |
C22A—C23A—C24A—N7A | −57.3 (8) | C22B—C23B—C24B—N7B | −56.9 (8) |
N4A—C16A—C26A—C31A | −149.4 (6) | N4B—C16B—C26B—C27B | −18.2 (8) |
C15A—C16A—C26A—C31A | 32.5 (10) | C15B—C16B—C26B—C27B | 160.2 (7) |
N4A—C16A—C26A—C27A | 27.5 (8) | N4B—C16B—C26B—C31B | 160.2 (6) |
C15A—C16A—C26A—C27A | −150.6 (7) | C15B—C16B—C26B—C31B | −21.5 (11) |
C31A—C26A—C27A—C28A | 0.7 (11) | C31B—C26B—C27B—C28B | −0.1 (10) |
C16A—C26A—C27A—C28A | −176.4 (7) | C16B—C26B—C27B—C28B | 178.4 (6) |
C26A—C27A—C28A—C29A | 0.5 (13) | C26B—C27B—C28B—C29B | 1.0 (11) |
C27A—C28A—C29A—C30A | −1.5 (12) | C27B—C28B—C29B—C30B | −2.5 (11) |
C27A—C28A—C29A—Br1A | 178.2 (6) | C27B—C28B—C29B—Br1B | 178.4 (5) |
C28A—C29A—C30A—C31A | 1.3 (11) | C28B—C29B—C30B—C31B | 3.2 (12) |
Br1A—C29A—C30A—C31A | −178.5 (5) | Br1B—C29B—C30B—C31B | −177.7 (6) |
C29A—C30A—C31A—C26A | 0.0 (10) | C29B—C30B—C31B—C26B | −2.3 (11) |
C27A—C26A—C31A—C30A | −0.9 (9) | C27B—C26B—C31B—C30B | 0.7 (10) |
C16A—C26A—C31A—C30A | 176.0 (6) | C16B—C26B—C31B—C30B | −177.7 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7A—H7A···O1Ai | 0.91 | 1.87 | 2.730 (6) | 156 |
N7A—H7A···N5A | 0.91 | 2.54 | 3.083 (8) | 119 |
N7B—H7B···O4Bi | 0.91 | 2.18 | 3.060 (6) | 161 |
N7B—H7B···N5B | 0.91 | 2.51 | 3.047 (7) | 118 |
C21A—H21A···O1Ai | 0.97 | 2.50 | 3.207 (9) | 129 |
C19A—H19A···O4A | 0.97 | 2.49 | 3.382 (9) | 154 |
C31A—H31A···O4A | 0.93 | 2.43 | 3.272 (11) | 151 |
C24A—H24A···O5A | 0.97 | 2.39 | 3.245 (9) | 147 |
C17A—H17A···O6Aii | 0.96 | 2.51 | 3.363 (11) | 147 |
C24B—H24C···O1B | 0.97 | 2.36 | 3.255 (8) | 153 |
C24B—H24C···O2B | 0.97 | 2.58 | 3.348 (14) | 136 |
C30B—H30B···O7B | 0.93 | 2.62 | 3.313 (11) | 132 |
C24A—H24B···F1A | 0.97 | 2.63 | 3.290 (10) | 126 |
C24B—H24D···F1B | 0.97 | 2.70 | 3.391 (9) | 128 |
C25A—H25A···F1Aiii | 0.96 | 2.52 | 3.283 (9) | 136 |
C28A—H28A···F1Biv | 0.93 | 2.67 | 3.558 (11) | 160 |
C28B—H28B···F2Aii | 0.93 | 2.77 | 3.441 (10) | 130 |
C3B—H3B···F3Bv | 0.93 | 2.84 | 3.419 (8) | 122 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+1, y+1/2, −z+3/2; (v) x+1, −y+1/2, z+1/2. |
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