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The title mol­ecular complex, C25H25BrF3N4+·C6H2N3O7, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501144X/sg6002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501144X/sg6002Isup2.hkl
Contains datablock I

CCDC reference: 272104

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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+·C6H2N3O7F(000) = 3040
Mr = 746.51Dx = 1.516 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.6304 (13) Åθ = 25–45°
b = 50.875 (7) ŵ = 2.38 mm1
c = 11.017 (3) ÅT = 293 K
β = 112.50 (1)°Prism, yellow
V = 6540 (2) Å30.4 × 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 tubeRint = 0.051
Graphite monochromatorθmax = 75.0°, θmin = 3.5°
ω–2θ scansh = 515
Absorption correction: ψ scan
(North et al., 1968)
k = 6310
Tmin = 0.472, Tmax = 0.514l = 1312
13650 measured reflections2 standard reflections every 100 reflections
13129 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.257H-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 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.62 e Å3
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
xyzUiso*/Ueq
O1A1.2715 (4)0.56980 (11)0.7850 (5)0.0903 (15)
N1A1.1404 (7)0.61842 (14)0.7335 (6)0.0850 (17)
O2A1.2447 (6)0.62146 (12)0.7788 (7)0.118 (2)
O3A1.0742 (6)0.63616 (12)0.6844 (7)0.123 (2)
N2A0.8120 (6)0.5659 (2)0.6980 (9)0.128 (3)
O4A0.7553 (6)0.58636 (16)0.6631 (10)0.167 (3)
O5A0.7702 (6)0.54568 (19)0.7152 (11)0.176 (4)
N3A1.1770 (6)0.52278 (14)0.8351 (8)0.0914 (19)
O6A1.1329 (6)0.50134 (12)0.7881 (8)0.134 (3)
O7A1.2716 (6)0.52422 (12)0.9211 (7)0.116 (2)
C1A1.1704 (5)0.56966 (14)0.7738 (6)0.0649 (16)
C2A1.0954 (6)0.59220 (13)0.7411 (6)0.0657 (16)
C3A0.9809 (6)0.59128 (15)0.7161 (7)0.0771 (19)
H3A0.93680.60650.69490.093*
C4A0.9322 (6)0.56744 (18)0.7229 (8)0.085 (2)
C5A0.9975 (6)0.54470 (14)0.7607 (8)0.079 (2)
H5A0.96370.52880.76730.095*
C6A1.1112 (5)0.54608 (14)0.7877 (6)0.0669 (17)
Br1A0.82695 (10)0.70759 (2)0.81561 (9)0.1219 (4)
F1A0.3194 (6)0.51042 (11)0.6582 (5)0.147 (2)
F2A0.3342 (6)0.50690 (11)0.4760 (7)0.154 (2)
F3A0.1919 (6)0.49033 (11)0.5056 (6)0.150 (2)
N4A0.3109 (5)0.64639 (11)0.5208 (5)0.0741 (15)
N5A0.2637 (5)0.55787 (13)0.5188 (5)0.0777 (16)
N6A0.2796 (5)0.60324 (11)0.5131 (5)0.0659 (13)
N7A0.4782 (4)0.57304 (9)0.7605 (4)0.0568 (12)
H7A0.40460.56910.74840.068*
C7A0.2320 (7)0.62785 (15)0.4777 (7)0.0742 (18)
C8A0.1130 (7)0.63016 (18)0.4052 (7)0.086 (2)
H8A0.08140.64680.38090.104*
C9A0.0460 (7)0.6096 (2)0.3713 (7)0.093 (2)
H9A0.03170.61180.32160.111*
C10A0.0916 (6)0.58355 (18)0.4101 (6)0.082 (2)
C11A0.0239 (7)0.56109 (19)0.3814 (7)0.089 (2)
C12A0.0786 (8)0.53752 (18)0.4220 (8)0.092 (2)
H12A0.03640.52200.40430.110*
C13A0.1949 (8)0.53667 (16)0.4882 (6)0.081 (2)
C14A0.2095 (6)0.58019 (15)0.4794 (6)0.0715 (18)
C15A0.3960 (6)0.60692 (13)0.5820 (6)0.0632 (16)
C16A0.4127 (6)0.63372 (13)0.5852 (6)0.0687 (17)
C17A0.1038 (8)0.56197 (19)0.3070 (10)0.128 (4)
H17A0.13420.54450.29710.192*
H17B0.12050.56950.22180.192*
H17C0.13820.57250.35440.192*
C18A0.2585 (10)0.5114 (2)0.5299 (9)0.107 (3)
C19A0.4791 (6)0.58484 (12)0.6349 (6)0.0649 (16)
H19A0.55560.59120.65090.078*
H19B0.46150.57110.56880.078*
C20A0.5242 (6)0.59177 (12)0.8719 (6)0.0700 (17)
H20A0.47700.60750.85260.084*
H20B0.60140.59690.88310.084*
C21A0.5258 (7)0.57940 (14)0.9978 (6)0.0788 (19)
H21A0.44780.57580.98890.095*
H21B0.55890.59171.06960.095*
C22A0.5950 (6)0.55377 (14)1.0303 (7)0.0764 (19)
H22A0.67460.55791.04400.092*
C23A0.5480 (6)0.53547 (13)0.9156 (7)0.0762 (19)
H23A0.47080.53030.90410.091*
H23B0.59480.51970.93300.091*
C24A0.5460 (6)0.54825 (12)0.7905 (7)0.0738 (18)
H24A0.62390.55200.79950.089*
H24B0.51310.53610.71790.089*
C25A0.5937 (8)0.54179 (18)1.1547 (8)0.108 (3)
H25A0.63810.52591.17390.163*
H25B0.51620.53791.14350.163*
H25C0.62610.55401.22590.163*
C26A0.5156 (6)0.64990 (13)0.6461 (6)0.0690 (17)
C27A0.5030 (8)0.67524 (16)0.6868 (8)0.093 (2)
H27A0.43070.68100.67910.112*
C28A0.5951 (9)0.69205 (17)0.7383 (9)0.104 (3)
H28A0.58460.70880.76530.124*
C29A0.7014 (8)0.68407 (17)0.7494 (7)0.090 (2)
C30A0.7171 (7)0.65930 (17)0.7125 (7)0.085 (2)
H30A0.79020.65380.72200.102*
C31A0.6254 (7)0.64211 (14)0.6610 (6)0.0756 (19)
H31A0.63740.62530.63620.091*
O1B0.9506 (4)0.33215 (11)0.8656 (6)0.0976 (16)
N1B1.0407 (8)0.2860 (2)0.7944 (10)0.127 (3)
O2B0.9497 (11)0.2866 (3)0.757 (2)0.496 (19)
O3B1.0771 (8)0.26701 (18)0.7777 (12)0.190 (4)
N2B1.4065 (5)0.32976 (13)0.9302 (5)0.0694 (14)
O4B1.4442 (4)0.30998 (10)0.8971 (5)0.0795 (13)
O5B1.4648 (4)0.34954 (12)0.9721 (6)0.0992 (16)
N3B1.1004 (6)0.37430 (16)1.0034 (7)0.100 (2)
O6B1.1442 (7)0.39547 (14)1.0021 (9)0.145 (3)
O7B1.0298 (6)0.37010 (14)1.0538 (7)0.129 (2)
C1B1.0531 (6)0.33102 (15)0.8856 (6)0.0727 (18)
C2B1.1069 (6)0.30899 (14)0.8469 (6)0.0689 (17)
C3B1.2193 (6)0.30836 (14)0.8624 (6)0.0671 (16)
H3B1.24930.29360.83740.081*
C4B1.2882 (5)0.32998 (13)0.9158 (6)0.0629 (16)
C5B1.2460 (6)0.35140 (13)0.9583 (6)0.0652 (16)
H5B1.29330.36570.99540.078*
C6B1.1354 (6)0.35162 (13)0.9461 (6)0.0690 (17)
Br1B0.93986 (11)0.469893 (19)0.90732 (10)0.1229 (4)
F1B0.5205 (5)0.25289 (9)0.7106 (6)0.1263 (18)
F2B0.5439 (5)0.26596 (10)0.5420 (6)0.1287 (19)
F3B0.4042 (5)0.24063 (11)0.5258 (7)0.163 (3)
N4B0.4554 (6)0.39479 (11)0.6911 (5)0.0798 (16)
N5B0.4483 (4)0.30666 (10)0.6281 (5)0.0623 (12)
N6B0.4442 (4)0.35129 (10)0.6658 (4)0.0611 (12)
N7B0.6682 (4)0.32054 (9)0.8594 (4)0.0548 (11)
H7B0.59710.31540.85250.066*
C7B0.3842 (7)0.37468 (16)0.6515 (6)0.079 (2)
C8B0.2649 (7)0.37478 (17)0.6049 (8)0.092 (2)
H8B0.22620.39050.60080.110*
C9B0.2062 (7)0.35276 (17)0.5667 (7)0.089 (2)
H9B0.12660.35320.53480.106*
C10B0.2641 (6)0.32797 (14)0.5737 (6)0.0695 (17)
C11B0.2076 (6)0.30424 (16)0.5304 (7)0.0786 (19)
C12B0.2724 (7)0.28207 (16)0.5350 (7)0.082 (2)
H12B0.23740.26590.50630.098*
C13B0.3897 (7)0.28445 (14)0.5830 (7)0.0745 (18)
C14B0.3847 (6)0.32764 (13)0.6210 (6)0.0635 (16)
C15B0.5601 (6)0.35774 (12)0.7176 (5)0.0600 (15)
C16B0.5639 (6)0.38490 (12)0.7315 (6)0.0683 (17)
C17B0.0783 (7)0.30244 (19)0.4755 (8)0.109 (3)
H17D0.05540.28460.45020.163*
H17E0.04710.31370.40020.163*
H17F0.05040.30780.54130.163*
C18B0.4640 (8)0.26107 (16)0.5876 (10)0.098 (2)
C19B0.6533 (5)0.33822 (11)0.7437 (6)0.0598 (15)
H19C0.72470.34750.76010.072*
H19D0.63710.32740.66600.072*
C20B0.7232 (6)0.33453 (12)0.9880 (6)0.0657 (16)
H20C0.67800.34980.98960.079*
H20D0.79910.34050.99800.079*
C21B0.7321 (6)0.31648 (14)1.0998 (6)0.0786 (19)
H21C0.76950.32581.18200.094*
H21D0.65550.31191.09310.094*
C22B0.7970 (6)0.29172 (14)1.1033 (8)0.087 (2)
H22B0.87610.29641.11750.105*
C23B0.7439 (7)0.27848 (14)0.9713 (8)0.091 (2)
H23C0.78960.26330.96980.109*
H23D0.66780.27230.95950.109*
C24B0.7349 (6)0.29631 (12)0.8589 (8)0.0763 (19)
H24C0.81120.30120.86560.092*
H24D0.69760.28700.77660.092*
C25B0.7995 (8)0.27346 (19)1.2155 (9)0.129 (4)
H25D0.83360.28251.29780.194*
H25E0.84370.25811.21620.194*
H25F0.72270.26841.20240.194*
C26B0.6596 (7)0.40423 (13)0.7770 (6)0.0710 (18)
C27B0.6337 (8)0.43025 (14)0.7409 (7)0.087 (2)
H27B0.55860.43470.68820.105*
C28B0.7154 (10)0.44992 (14)0.7803 (8)0.095 (3)
H28B0.69550.46730.75570.114*
C29B0.8261 (9)0.44328 (16)0.8562 (8)0.091 (2)
C30B0.8547 (7)0.41829 (15)0.8963 (8)0.086 (2)
H30B0.92960.41430.95150.103*
C31B0.7730 (7)0.39845 (14)0.8558 (7)0.082 (2)
H31B0.79410.38120.88140.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.055 (3)0.133 (4)0.090 (3)0.012 (3)0.036 (3)0.020 (3)
N1A0.106 (5)0.087 (5)0.073 (4)0.011 (4)0.046 (4)0.005 (3)
O2A0.110 (5)0.114 (5)0.132 (5)0.028 (4)0.049 (4)0.008 (4)
O3A0.153 (6)0.075 (4)0.137 (5)0.013 (4)0.051 (5)0.016 (4)
N2A0.062 (5)0.172 (9)0.168 (8)0.015 (6)0.064 (5)0.009 (7)
O4A0.078 (4)0.150 (6)0.280 (11)0.035 (4)0.075 (6)0.020 (6)
O5A0.092 (5)0.191 (8)0.290 (12)0.025 (5)0.123 (7)0.030 (8)
N3A0.070 (4)0.098 (5)0.117 (6)0.005 (4)0.048 (4)0.012 (4)
O6A0.113 (5)0.069 (4)0.224 (8)0.000 (3)0.068 (5)0.023 (4)
O7A0.095 (4)0.115 (5)0.134 (5)0.028 (4)0.039 (4)0.007 (4)
C1A0.049 (4)0.094 (5)0.053 (3)0.003 (3)0.021 (3)0.014 (3)
C2A0.080 (5)0.070 (4)0.055 (3)0.008 (3)0.035 (3)0.013 (3)
C3A0.074 (5)0.088 (5)0.077 (5)0.016 (4)0.037 (4)0.000 (4)
C4A0.059 (4)0.110 (6)0.093 (5)0.007 (4)0.037 (4)0.010 (4)
C5A0.069 (5)0.079 (5)0.107 (6)0.005 (4)0.052 (4)0.017 (4)
C6A0.055 (4)0.082 (5)0.068 (4)0.003 (3)0.029 (3)0.015 (3)
Br1A0.1511 (10)0.1309 (9)0.0762 (6)0.0523 (7)0.0352 (6)0.0022 (5)
F1A0.189 (6)0.117 (4)0.095 (4)0.002 (4)0.010 (4)0.028 (3)
F2A0.204 (7)0.109 (4)0.183 (6)0.047 (4)0.109 (6)0.033 (4)
F3A0.159 (5)0.095 (4)0.170 (6)0.027 (4)0.035 (4)0.007 (4)
N4A0.091 (4)0.071 (4)0.067 (3)0.020 (3)0.038 (3)0.020 (3)
N5A0.088 (4)0.097 (5)0.051 (3)0.003 (4)0.030 (3)0.005 (3)
N6A0.076 (4)0.074 (4)0.053 (3)0.006 (3)0.031 (3)0.007 (3)
N7A0.053 (3)0.070 (3)0.051 (3)0.003 (2)0.024 (2)0.005 (2)
C7A0.093 (5)0.075 (5)0.060 (4)0.019 (4)0.036 (4)0.013 (3)
C8A0.087 (6)0.102 (6)0.065 (4)0.028 (5)0.023 (4)0.008 (4)
C9A0.075 (5)0.137 (8)0.058 (4)0.016 (5)0.015 (4)0.005 (5)
C10A0.069 (5)0.126 (7)0.052 (4)0.005 (5)0.025 (3)0.013 (4)
C11A0.087 (6)0.104 (6)0.072 (5)0.007 (5)0.026 (4)0.022 (4)
C12A0.103 (7)0.101 (6)0.072 (5)0.019 (5)0.035 (5)0.019 (4)
C13A0.101 (6)0.092 (6)0.049 (4)0.005 (5)0.027 (4)0.005 (4)
C14A0.084 (5)0.089 (5)0.051 (4)0.009 (4)0.036 (3)0.008 (3)
C15A0.075 (4)0.070 (4)0.053 (3)0.008 (3)0.034 (3)0.013 (3)
C16A0.087 (5)0.071 (4)0.063 (4)0.015 (4)0.046 (4)0.020 (3)
C17A0.090 (7)0.120 (7)0.152 (9)0.009 (5)0.022 (6)0.046 (7)
C18A0.125 (8)0.099 (7)0.081 (6)0.022 (6)0.023 (6)0.005 (5)
C19A0.080 (4)0.062 (4)0.062 (4)0.003 (3)0.037 (3)0.011 (3)
C20A0.089 (5)0.055 (4)0.063 (4)0.001 (3)0.025 (3)0.003 (3)
C21A0.096 (5)0.083 (5)0.051 (4)0.001 (4)0.022 (3)0.001 (3)
C22A0.070 (4)0.084 (5)0.067 (4)0.008 (4)0.017 (3)0.017 (4)
C23A0.081 (5)0.073 (4)0.074 (4)0.019 (4)0.029 (4)0.022 (4)
C24A0.082 (5)0.065 (4)0.080 (4)0.021 (3)0.037 (4)0.016 (3)
C25A0.118 (7)0.127 (7)0.078 (5)0.024 (6)0.035 (5)0.035 (5)
C26A0.084 (5)0.073 (4)0.057 (4)0.009 (4)0.035 (3)0.017 (3)
C27A0.110 (7)0.082 (5)0.100 (6)0.012 (5)0.054 (5)0.001 (5)
C28A0.133 (8)0.083 (6)0.104 (7)0.002 (6)0.057 (6)0.009 (5)
C29A0.120 (7)0.086 (6)0.065 (4)0.015 (5)0.038 (5)0.009 (4)
C30A0.087 (5)0.101 (6)0.069 (4)0.000 (5)0.033 (4)0.019 (4)
C31A0.093 (5)0.068 (4)0.067 (4)0.004 (4)0.032 (4)0.015 (3)
O1B0.059 (3)0.117 (4)0.122 (4)0.007 (3)0.040 (3)0.017 (3)
N1B0.082 (6)0.138 (8)0.189 (9)0.042 (6)0.084 (6)0.064 (7)
O2B0.209 (11)0.340 (17)1.06 (5)0.202 (12)0.38 (2)0.49 (3)
O3B0.133 (7)0.120 (6)0.302 (13)0.018 (5)0.068 (8)0.046 (7)
N2B0.065 (4)0.090 (4)0.058 (3)0.004 (3)0.027 (3)0.012 (3)
O4B0.074 (3)0.094 (4)0.081 (3)0.007 (3)0.041 (3)0.007 (3)
O5B0.069 (3)0.110 (4)0.120 (4)0.020 (3)0.038 (3)0.004 (3)
N3B0.091 (5)0.099 (6)0.115 (6)0.021 (4)0.048 (4)0.002 (4)
O6B0.148 (6)0.080 (4)0.227 (9)0.001 (4)0.093 (6)0.021 (5)
O7B0.122 (5)0.151 (6)0.138 (6)0.026 (4)0.076 (5)0.016 (4)
C1B0.059 (4)0.096 (5)0.066 (4)0.010 (4)0.028 (3)0.024 (4)
C2B0.060 (4)0.079 (4)0.070 (4)0.011 (3)0.027 (3)0.001 (3)
C3B0.068 (4)0.080 (4)0.061 (4)0.001 (3)0.032 (3)0.008 (3)
C4B0.052 (4)0.085 (5)0.053 (3)0.003 (3)0.022 (3)0.012 (3)
C5B0.062 (4)0.068 (4)0.063 (4)0.002 (3)0.021 (3)0.006 (3)
C6B0.077 (5)0.066 (4)0.065 (4)0.008 (3)0.029 (3)0.013 (3)
Br1B0.1919 (11)0.0972 (7)0.1045 (7)0.0646 (7)0.0844 (7)0.0289 (5)
F1B0.133 (4)0.088 (3)0.136 (5)0.010 (3)0.027 (4)0.022 (3)
F2B0.158 (5)0.096 (3)0.168 (5)0.017 (3)0.102 (4)0.005 (3)
F3B0.139 (5)0.105 (4)0.201 (7)0.013 (4)0.017 (4)0.067 (4)
N4B0.102 (5)0.066 (4)0.067 (3)0.021 (3)0.028 (3)0.006 (3)
N5B0.068 (3)0.059 (3)0.059 (3)0.002 (3)0.024 (3)0.004 (2)
N6B0.062 (3)0.071 (3)0.049 (3)0.008 (3)0.020 (2)0.002 (2)
N7B0.048 (3)0.053 (3)0.065 (3)0.002 (2)0.024 (2)0.007 (2)
C7B0.085 (5)0.089 (5)0.056 (4)0.026 (4)0.021 (4)0.002 (4)
C8B0.082 (6)0.098 (6)0.084 (5)0.033 (5)0.020 (4)0.011 (4)
C9B0.075 (5)0.105 (6)0.082 (5)0.020 (5)0.025 (4)0.012 (4)
C10B0.069 (4)0.084 (5)0.052 (3)0.001 (4)0.018 (3)0.002 (3)
C11B0.073 (5)0.100 (6)0.064 (4)0.011 (4)0.028 (4)0.004 (4)
C12B0.081 (5)0.089 (5)0.069 (4)0.019 (4)0.022 (4)0.005 (4)
C13B0.086 (5)0.073 (5)0.066 (4)0.004 (4)0.030 (4)0.003 (3)
C14B0.066 (4)0.078 (4)0.047 (3)0.000 (3)0.021 (3)0.001 (3)
C15B0.074 (4)0.062 (4)0.049 (3)0.001 (3)0.030 (3)0.002 (3)
C16B0.099 (5)0.059 (4)0.051 (3)0.010 (4)0.033 (3)0.001 (3)
C17B0.078 (6)0.146 (8)0.097 (6)0.023 (5)0.028 (5)0.009 (6)
C18B0.101 (7)0.071 (5)0.109 (7)0.010 (5)0.026 (6)0.004 (5)
C19B0.066 (4)0.058 (3)0.064 (4)0.006 (3)0.035 (3)0.002 (3)
C20B0.066 (4)0.062 (4)0.068 (4)0.001 (3)0.023 (3)0.006 (3)
C21B0.072 (4)0.090 (5)0.062 (4)0.010 (4)0.013 (3)0.016 (4)
C22B0.060 (4)0.078 (5)0.104 (6)0.002 (4)0.010 (4)0.029 (4)
C23B0.081 (5)0.068 (4)0.119 (7)0.011 (4)0.033 (5)0.018 (4)
C24B0.066 (4)0.061 (4)0.107 (6)0.002 (3)0.040 (4)0.002 (4)
C25B0.116 (7)0.125 (8)0.116 (7)0.004 (6)0.010 (6)0.050 (6)
C26B0.105 (6)0.060 (4)0.056 (4)0.001 (4)0.040 (4)0.002 (3)
C27B0.129 (7)0.069 (5)0.074 (5)0.008 (5)0.051 (5)0.002 (4)
C28B0.162 (9)0.051 (4)0.089 (6)0.003 (5)0.067 (6)0.001 (4)
C29B0.142 (8)0.072 (5)0.080 (5)0.018 (5)0.066 (6)0.007 (4)
C30B0.101 (6)0.075 (5)0.086 (5)0.017 (4)0.041 (4)0.008 (4)
C31B0.099 (6)0.065 (4)0.081 (5)0.006 (4)0.032 (4)0.003 (4)
Geometric parameters (Å, º) top
O1A—C1A1.235 (7)O1B—C1B1.230 (7)
N1A—O3A1.208 (8)N1B—O2B1.063 (14)
N1A—O2A1.227 (8)N1B—O3B1.114 (10)
N1A—C2A1.465 (9)N1B—C2B1.426 (10)
N2A—O5A1.204 (11)N2B—O4B1.227 (7)
N2A—O4A1.239 (10)N2B—O5B1.228 (7)
N2A—C4A1.437 (10)N2B—C4B1.440 (8)
N3A—O7A1.211 (8)N3B—O6B1.213 (9)
N3A—O6A1.244 (8)N3B—O7B1.236 (9)
N3A—C6A1.427 (9)N3B—C6B1.462 (9)
C1A—C2A1.443 (9)C1B—C6B1.447 (10)
C1A—C6A1.453 (9)C1B—C2B1.456 (9)
C2A—C3A1.366 (9)C2B—C3B1.364 (9)
C3A—C4A1.375 (10)C3B—C4B1.387 (9)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.389 (10)C4B—C5B1.372 (9)
C5A—C6A1.352 (9)C5B—C6B1.351 (9)
C5A—H5A0.9300C5B—H5B0.9300
Br1A—C29A1.896 (9)Br1B—C29B1.896 (8)
F1A—C18A1.327 (10)F1B—C18B1.333 (10)
F2A—C18A1.325 (11)F2B—C18B1.311 (10)
F3A—C18A1.324 (10)F3B—C18B1.312 (9)
N4A—C7A1.321 (9)N4B—C7B1.321 (9)
N4A—C16A1.369 (8)N4B—C16B1.365 (9)
N5A—C14A1.311 (8)N5B—C14B1.320 (8)
N5A—C13A1.345 (9)N5B—C13B1.338 (8)
N6A—C7A1.379 (8)N6B—C7B1.386 (8)
N6A—C15A1.385 (8)N6B—C15B1.392 (8)
N6A—C14A1.430 (9)N6B—C14B1.404 (8)
N7A—C20A1.485 (7)N7B—C24B1.495 (7)
N7A—C24A1.488 (7)N7B—C20B1.498 (7)
N7A—C19A1.513 (7)N7B—C19B1.512 (7)
N7A—H7A0.9100N7B—H7B0.9100
C7A—C8A1.412 (10)C7B—C8B1.395 (11)
C8A—C9A1.305 (11)C8B—C9B1.320 (11)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.445 (11)C9B—C10B1.445 (10)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.389 (11)C10B—C11B1.391 (9)
C10A—C14A1.400 (10)C10B—C14B1.409 (9)
C11A—C12A1.370 (11)C11B—C12B1.383 (10)
C11A—C17A1.505 (11)C11B—C17B1.511 (10)
C12A—C13A1.368 (11)C12B—C13B1.375 (10)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C18A1.493 (12)C13B—C18B1.505 (11)
C15A—C16A1.378 (9)C15B—C16B1.389 (8)
C15A—C19A1.495 (8)C15B—C19B1.483 (8)
C16A—C26A1.466 (10)C16B—C26B1.489 (10)
C17A—H17A0.9600C17B—H17D0.9600
C17A—H17B0.9600C17B—H17E0.9600
C17A—H17C0.9600C17B—H17F0.9600
C19A—H19A0.9700C19B—H19C0.9700
C19A—H19B0.9700C19B—H19D0.9700
C20A—C21A1.516 (9)C20B—C21B1.506 (8)
C20A—H20A0.9700C20B—H20C0.9700
C20A—H20B0.9700C20B—H20D0.9700
C21A—C22A1.534 (9)C21B—C22B1.495 (10)
C21A—H21A0.9700C21B—H21C0.9700
C21A—H21B0.9700C21B—H21D0.9700
C22A—C23A1.498 (10)C22B—C23B1.508 (11)
C22A—C25A1.505 (10)C22B—C25B1.537 (11)
C22A—H22A0.9800C22B—H22B0.9800
C23A—C24A1.515 (9)C23B—C24B1.504 (10)
C23A—H23A0.9700C23B—H23C0.9700
C23A—H23B0.9700C23B—H23D0.9700
C24A—H24A0.9700C24B—H24C0.9700
C24A—H24B0.9700C24B—H24D0.9700
C25A—H25A0.9600C25B—H25D0.9600
C25A—H25B0.9600C25B—H25E0.9600
C25A—H25C0.9600C25B—H25F0.9600
C26A—C31A1.390 (9)C26B—C27B1.385 (9)
C26A—C27A1.394 (10)C26B—C31B1.392 (10)
C27A—C28A1.378 (12)C27B—C28B1.382 (11)
C27A—H27A0.9300C27B—H27B0.9300
C28A—C29A1.363 (12)C28B—C29B1.369 (12)
C28A—H28A0.9300C28B—H28B0.9300
C29A—C30A1.362 (11)C29B—C30B1.349 (11)
C30A—C31A1.388 (10)C30B—C31B1.390 (10)
C30A—H30A0.9300C30B—H30B0.9300
C31A—H31A0.9300C31B—H31B0.9300
O3A—N1A—O2A122.6 (8)O2B—N1B—O3B114.4 (11)
O3A—N1A—C2A119.2 (7)O2B—N1B—C2B120.9 (11)
O2A—N1A—C2A118.1 (7)O3B—N1B—C2B124.3 (9)
O5A—N2A—O4A122.0 (8)O4B—N2B—O5B122.6 (6)
O5A—N2A—C4A120.7 (10)O4B—N2B—C4B118.5 (6)
O4A—N2A—C4A117.2 (10)O5B—N2B—C4B118.8 (6)
O7A—N3A—O6A122.0 (8)O6B—N3B—O7B124.7 (8)
O7A—N3A—C6A119.9 (7)O6B—N3B—C6B118.8 (8)
O6A—N3A—C6A118.1 (7)O7B—N3B—C6B116.5 (8)
O1A—C1A—C2A125.1 (7)O1B—C1B—C6B124.8 (7)
O1A—C1A—C6A123.3 (6)O1B—C1B—C2B124.1 (7)
C2A—C1A—C6A111.5 (5)C6B—C1B—C2B111.0 (6)
C3A—C2A—C1A124.5 (6)C3B—C2B—N1B116.9 (7)
C3A—C2A—N1A115.1 (7)C3B—C2B—C1B124.1 (6)
C1A—C2A—N1A120.4 (6)N1B—C2B—C1B119.0 (6)
C2A—C3A—C4A118.8 (7)C2B—C3B—C4B119.3 (6)
C2A—C3A—H3A120.6C2B—C3B—H3B120.4
C4A—C3A—H3A120.6C4B—C3B—H3B120.4
C3A—C4A—C5A121.6 (7)C5B—C4B—C3B120.8 (6)
C3A—C4A—N2A120.0 (8)C5B—C4B—N2B119.4 (6)
C5A—C4A—N2A118.4 (8)C3B—C4B—N2B119.8 (6)
C6A—C5A—C4A118.8 (7)C6B—C5B—C4B119.6 (6)
C6A—C5A—H5A120.6C6B—C5B—H5B120.2
C4A—C5A—H5A120.6C4B—C5B—H5B120.2
C5A—C6A—N3A117.3 (7)C5B—C6B—C1B125.0 (6)
C5A—C6A—C1A124.5 (7)C5B—C6B—N3B115.8 (7)
N3A—C6A—C1A118.2 (6)C1B—C6B—N3B119.2 (7)
C7A—N4A—C16A106.2 (6)C7B—N4B—C16B107.1 (6)
C14A—N5A—C13A113.9 (7)C14B—N5B—C13B115.0 (6)
C7A—N6A—C15A106.8 (6)C7B—N6B—C15B106.7 (6)
C7A—N6A—C14A120.8 (6)C7B—N6B—C14B120.0 (6)
C15A—N6A—C14A132.4 (6)C15B—N6B—C14B133.1 (5)
C20A—N7A—C24A110.5 (5)C24B—N7B—C20B109.7 (5)
C20A—N7A—C19A111.3 (5)C24B—N7B—C19B112.0 (5)
C24A—N7A—C19A109.6 (4)C20B—N7B—C19B112.2 (4)
C20A—N7A—H7A108.5C24B—N7B—H7B107.5
C24A—N7A—H7A108.4C20B—N7B—H7B107.5
C19A—N7A—H7A108.4C19B—N7B—H7B107.5
N4A—C7A—N6A111.1 (6)N4B—C7B—N6B110.8 (6)
N4A—C7A—C8A129.6 (7)N4B—C7B—C8B128.4 (7)
N6A—C7A—C8A119.4 (8)N6B—C7B—C8B120.8 (8)
C9A—C8A—C7A121.9 (8)C9B—C8B—C7B120.6 (7)
C9A—C8A—H8A119.1C9B—C8B—H8B119.7
C7A—C8A—H8A119.1C7B—C8B—H8B119.7
C8A—C9A—C10A120.6 (8)C8B—C9B—C10B120.9 (7)
C8A—C9A—H9A119.7C8B—C9B—H9B119.6
C10A—C9A—H9A119.7C10B—C9B—H9B119.6
C11A—C10A—C14A117.2 (8)C11B—C10B—C14B117.2 (7)
C11A—C10A—C9A123.2 (8)C11B—C10B—C9B123.8 (7)
C14A—C10A—C9A119.6 (8)C14B—C10B—C9B118.9 (7)
C12A—C11A—C10A117.2 (8)C12B—C11B—C10B118.4 (7)
C12A—C11A—C17A120.3 (8)C12B—C11B—C17B119.9 (7)
C10A—C11A—C17A122.5 (8)C10B—C11B—C17B121.6 (8)
C13A—C12A—C11A120.4 (8)C13B—C12B—C11B118.5 (7)
C13A—C12A—H12A119.8C13B—C12B—H12B120.7
C11A—C12A—H12A119.8C11B—C12B—H12B120.7
N5A—C13A—C12A124.6 (8)N5B—C13B—C12B125.4 (7)
N5A—C13A—C18A113.2 (8)N5B—C13B—C18B113.9 (7)
C12A—C13A—C18A122.2 (8)C12B—C13B—C18B120.7 (7)
N5A—C14A—C10A126.7 (8)N5B—C14B—N6B116.1 (6)
N5A—C14A—N6A115.6 (7)N5B—C14B—C10B125.4 (6)
C10A—C14A—N6A117.7 (7)N6B—C14B—C10B118.5 (6)
C16A—C15A—N6A105.5 (6)C16B—C15B—N6B105.5 (6)
C16A—C15A—C19A131.0 (6)C16B—C15B—C19B130.8 (6)
N6A—C15A—C19A123.5 (6)N6B—C15B—C19B123.7 (5)
N4A—C16A—C15A110.4 (7)N4B—C16B—C15B110.0 (6)
N4A—C16A—C26A117.7 (6)N4B—C16B—C26B116.8 (6)
C15A—C16A—C26A131.8 (6)C15B—C16B—C26B133.1 (7)
C11A—C17A—H17A109.5C11B—C17B—H17D109.5
C11A—C17A—H17B109.5C11B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
C11A—C17A—H17C109.5C11B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
F3A—C18A—F2A106.3 (9)F2B—C18B—F3B109.0 (9)
F3A—C18A—F1A104.5 (8)F2B—C18B—F1B105.0 (8)
F2A—C18A—F1A104.3 (9)F3B—C18B—F1B105.0 (7)
F3A—C18A—C13A114.2 (9)F2B—C18B—C13B113.5 (7)
F2A—C18A—C13A114.0 (8)F3B—C18B—C13B112.4 (8)
F1A—C18A—C13A112.6 (8)F1B—C18B—C13B111.4 (8)
C15A—C19A—N7A113.9 (5)C15B—C19B—N7B113.3 (4)
C15A—C19A—H19A108.8C15B—C19B—H19C108.9
N7A—C19A—H19A108.8N7B—C19B—H19C108.9
C15A—C19A—H19B108.8C15B—C19B—H19D108.9
N7A—C19A—H19B108.8N7B—C19B—H19D108.9
H19A—C19A—H19B107.7H19C—C19B—H19D107.7
N7A—C20A—C21A110.7 (5)N7B—C20B—C21B110.3 (5)
N7A—C20A—H20A109.5N7B—C20B—H20C109.6
C21A—C20A—H20A109.5C21B—C20B—H20C109.6
N7A—C20A—H20B109.5N7B—C20B—H20D109.6
C21A—C20A—H20B109.5C21B—C20B—H20D109.6
H20A—C20A—H20B108.1H20C—C20B—H20D108.1
C20A—C21A—C22A112.0 (6)C22B—C21B—C20B113.8 (6)
C20A—C21A—H21A109.2C22B—C21B—H21C108.8
C22A—C21A—H21A109.2C20B—C21B—H21C108.8
C20A—C21A—H21B109.2C22B—C21B—H21D108.8
C22A—C21A—H21B109.2C20B—C21B—H21D108.8
H21A—C21A—H21B107.9H21C—C21B—H21D107.7
C23A—C22A—C25A112.2 (6)C21B—C22B—C23B108.3 (6)
C23A—C22A—C21A109.0 (5)C21B—C22B—C25B111.9 (8)
C25A—C22A—C21A110.7 (6)C23B—C22B—C25B111.7 (7)
C23A—C22A—H22A108.3C21B—C22B—H22B108.3
C25A—C22A—H22A108.3C23B—C22B—H22B108.3
C21A—C22A—H22A108.3C25B—C22B—H22B108.3
C22A—C23A—C24A111.3 (6)C24B—C23B—C22B113.0 (6)
C22A—C23A—H23A109.4C24B—C23B—H23C109.0
C24A—C23A—H23A109.4C22B—C23B—H23C109.0
C22A—C23A—H23B109.4C24B—C23B—H23D109.0
C24A—C23A—H23B109.4C22B—C23B—H23D109.0
H23A—C23A—H23B108.0H23C—C23B—H23D107.8
N7A—C24A—C23A111.9 (5)N7B—C24B—C23B111.0 (6)
N7A—C24A—H24A109.2N7B—C24B—H24C109.4
C23A—C24A—H24A109.2C23B—C24B—H24C109.4
N7A—C24A—H24B109.2N7B—C24B—H24D109.4
C23A—C24A—H24B109.2C23B—C24B—H24D109.4
H24A—C24A—H24B107.9H24C—C24B—H24D108.0
C22A—C25A—H25A109.5C22B—C25B—H25D109.5
C22A—C25A—H25B109.5C22B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
C22A—C25A—H25C109.5C22B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
C31A—C26A—C27A117.2 (7)C27B—C26B—C31B117.0 (7)
C31A—C26A—C16A124.3 (6)C27B—C26B—C16B117.6 (7)
C27A—C26A—C16A118.5 (7)C31B—C26B—C16B125.4 (6)
C28A—C27A—C26A121.6 (8)C28B—C27B—C26B122.4 (8)
C28A—C27A—H27A119.2C28B—C27B—H27B118.8
C26A—C27A—H27A119.2C26B—C27B—H27B118.8
C29A—C28A—C27A120.0 (8)C29B—C28B—C27B118.6 (7)
C29A—C28A—H28A120.0C29B—C28B—H28B120.7
C27A—C28A—H28A120.0C27B—C28B—H28B120.7
C30A—C29A—C28A120.0 (8)C30B—C29B—C28B121.0 (8)
C30A—C29A—Br1A120.2 (7)C30B—C29B—Br1B119.9 (8)
C28A—C29A—Br1A119.8 (7)C28B—C29B—Br1B119.1 (7)
C29A—C30A—C31A120.7 (8)C29B—C30B—C31B120.4 (8)
C29A—C30A—H30A119.7C29B—C30B—H30B119.8
C31A—C30A—H30A119.7C31B—C30B—H30B119.8
C30A—C31A—C26A120.5 (7)C30B—C31B—C26B120.5 (7)
C30A—C31A—H31A119.7C30B—C31B—H31B119.8
C26A—C31A—H31A119.7C26B—C31B—H31B119.8
O1A—C1A—C2A—C3A173.1 (6)O2B—N1B—C2B—C3B164.0 (18)
C6A—C1A—C2A—C3A4.8 (8)O3B—N1B—C2B—C3B8.2 (17)
O1A—C1A—C2A—N1A7.3 (9)O2B—N1B—C2B—C1B19 (2)
C6A—C1A—C2A—N1A174.8 (5)O3B—N1B—C2B—C1B169.3 (12)
O3A—N1A—C2A—C3A13.2 (9)O1B—C1B—C2B—C3B176.1 (7)
O2A—N1A—C2A—C3A166.3 (6)C6B—C1B—C2B—C3B1.8 (9)
O3A—N1A—C2A—C1A167.2 (6)O1B—C1B—C2B—N1B6.6 (11)
O2A—N1A—C2A—C1A13.4 (9)C6B—C1B—C2B—N1B175.4 (7)
C1A—C2A—C3A—C4A0.5 (10)N1B—C2B—C3B—C4B178.6 (7)
N1A—C2A—C3A—C4A179.2 (6)C1B—C2B—C3B—C4B1.3 (10)
C2A—C3A—C4A—C5A3.2 (11)C2B—C3B—C4B—C5B2.9 (9)
C2A—C3A—C4A—N2A179.6 (7)C2B—C3B—C4B—N2B178.7 (5)
O5A—N2A—C4A—C3A173.1 (10)O4B—N2B—C4B—C5B176.8 (5)
O4A—N2A—C4A—C3A4.2 (13)O5B—N2B—C4B—C5B4.8 (8)
O5A—N2A—C4A—C5A3.3 (14)O4B—N2B—C4B—C3B1.7 (8)
O4A—N2A—C4A—C5A179.3 (9)O5B—N2B—C4B—C3B176.7 (6)
C3A—C4A—C5A—C6A1.9 (11)C3B—C4B—C5B—C6B1.0 (9)
N2A—C4A—C5A—C6A178.3 (7)N2B—C4B—C5B—C6B179.5 (5)
C4A—C5A—C6A—N3A175.7 (7)C4B—C5B—C6B—C1B2.5 (10)
C4A—C5A—C6A—C1A3.3 (11)C4B—C5B—C6B—N3B175.3 (6)
O7A—N3A—C6A—C5A140.5 (7)O1B—C1B—C6B—C5B174.2 (7)
O6A—N3A—C6A—C5A37.6 (10)C2B—C1B—C6B—C5B3.8 (9)
O7A—N3A—C6A—C1A38.5 (10)O1B—C1B—C6B—N3B8.0 (10)
O6A—N3A—C6A—C1A143.4 (7)C2B—C1B—C6B—N3B174.0 (6)
O1A—C1A—C6A—C5A171.7 (7)O6B—N3B—C6B—C5B33.3 (10)
C2A—C1A—C6A—C5A6.3 (9)O7B—N3B—C6B—C5B144.4 (7)
O1A—C1A—C6A—N3A9.3 (9)O6B—N3B—C6B—C1B148.7 (8)
C2A—C1A—C6A—N3A172.7 (6)O7B—N3B—C6B—C1B33.5 (10)
C16A—N4A—C7A—N6A0.3 (7)C16B—N4B—C7B—N6B0.5 (7)
C16A—N4A—C7A—C8A179.9 (7)C16B—N4B—C7B—C8B178.2 (7)
C15A—N6A—C7A—N4A0.4 (7)C15B—N6B—C7B—N4B0.2 (7)
C14A—N6A—C7A—N4A178.6 (5)C14B—N6B—C7B—N4B175.7 (5)
C15A—N6A—C7A—C8A179.8 (6)C15B—N6B—C7B—C8B178.1 (6)
C14A—N6A—C7A—C8A1.3 (9)C14B—N6B—C7B—C8B6.4 (9)
N4A—C7A—C8A—C9A179.2 (7)N4B—C7B—C8B—C9B178.7 (8)
N6A—C7A—C8A—C9A0.6 (11)N6B—C7B—C8B—C9B3.8 (12)
C7A—C8A—C9A—C10A1.6 (11)C7B—C8B—C9B—C10B0.9 (12)
C8A—C9A—C10A—C11A177.3 (7)C8B—C9B—C10B—C11B177.4 (7)
C8A—C9A—C10A—C14A3.1 (10)C8B—C9B—C10B—C14B0.6 (11)
C14A—C10A—C11A—C12A0.8 (10)C14B—C10B—C11B—C12B0.7 (9)
C9A—C10A—C11A—C12A178.8 (7)C9B—C10B—C11B—C12B176.2 (7)
C14A—C10A—C11A—C17A179.7 (7)C14B—C10B—C11B—C17B178.9 (6)
C9A—C10A—C11A—C17A0.1 (12)C9B—C10B—C11B—C17B2.0 (11)
C10A—C11A—C12A—C13A0.3 (11)C10B—C11B—C12B—C13B0.5 (10)
C17A—C11A—C12A—C13A179.2 (8)C17B—C11B—C12B—C13B178.7 (7)
C14A—N5A—C13A—C12A0.1 (10)C14B—N5B—C13B—C12B1.8 (9)
C14A—N5A—C13A—C18A178.1 (6)C14B—N5B—C13B—C18B177.9 (6)
C11A—C12A—C13A—N5A0.1 (11)C11B—C12B—C13B—N5B0.8 (11)
C11A—C12A—C13A—C18A177.7 (8)C11B—C12B—C13B—C18B178.8 (7)
C13A—N5A—C14A—C10A0.7 (9)C13B—N5B—C14B—N6B179.0 (5)
C13A—N5A—C14A—N6A178.5 (5)C13B—N5B—C14B—C10B1.4 (9)
C11A—C10A—C14A—N5A1.1 (10)C7B—N6B—C14B—N5B174.4 (5)
C9A—C10A—C14A—N5A178.5 (6)C15B—N6B—C14B—N5B0.3 (9)
C11A—C10A—C14A—N6A178.1 (6)C7B—N6B—C14B—C10B6.1 (8)
C9A—C10A—C14A—N6A2.3 (9)C15B—N6B—C14B—C10B179.9 (6)
C7A—N6A—C14A—N5A179.5 (5)C11B—C10B—C14B—N5B0.3 (9)
C15A—N6A—C14A—N5A0.9 (9)C9B—C10B—C14B—N5B177.3 (6)
C7A—N6A—C14A—C10A0.2 (8)C11B—C10B—C14B—N6B179.8 (5)
C15A—N6A—C14A—C10A178.4 (6)C9B—C10B—C14B—N6B3.2 (9)
C7A—N6A—C15A—C16A0.2 (6)C7B—N6B—C15B—C16B0.2 (6)
C14A—N6A—C15A—C16A178.5 (6)C14B—N6B—C15B—C16B174.5 (6)
C7A—N6A—C15A—C19A178.5 (5)C7B—N6B—C15B—C19B177.9 (5)
C14A—N6A—C15A—C19A2.8 (9)C14B—N6B—C15B—C19B3.3 (9)
C7A—N4A—C16A—C15A0.2 (7)C7B—N4B—C16B—C15B0.6 (7)
C7A—N4A—C16A—C26A178.6 (5)C7B—N4B—C16B—C26B178.1 (5)
N6A—C15A—C16A—N4A0.0 (6)N6B—C15B—C16B—N4B0.5 (6)
C19A—C15A—C16A—N4A178.5 (6)C19B—C15B—C16B—N4B178.0 (6)
N6A—C15A—C16A—C26A178.1 (6)N6B—C15B—C16B—C26B177.9 (6)
C19A—C15A—C16A—C26A3.3 (11)C19B—C15B—C16B—C26B0.4 (11)
N5A—C13A—C18A—F3A177.4 (7)N5B—C13B—C18B—F2B46.5 (10)
C12A—C13A—C18A—F3A4.6 (12)C12B—C13B—C18B—F2B133.2 (8)
N5A—C13A—C18A—F2A60.2 (10)N5B—C13B—C18B—F3B170.7 (7)
C12A—C13A—C18A—F2A117.9 (9)C12B—C13B—C18B—F3B8.9 (12)
N5A—C13A—C18A—F1A58.4 (11)N5B—C13B—C18B—F1B71.8 (9)
C12A—C13A—C18A—F1A123.5 (9)C12B—C13B—C18B—F1B108.6 (8)
C16A—C15A—C19A—N7A103.2 (7)C16B—C15B—C19B—N7B111.3 (7)
N6A—C15A—C19A—N7A78.4 (7)N6B—C15B—C19B—N7B71.6 (7)
C20A—N7A—C19A—C15A68.4 (7)C24B—N7B—C19B—C15B162.3 (5)
C24A—N7A—C19A—C15A169.0 (6)C20B—N7B—C19B—C15B73.8 (6)
C24A—N7A—C20A—C21A56.5 (7)C24B—N7B—C20B—C21B56.9 (6)
C19A—N7A—C20A—C21A178.5 (5)C19B—N7B—C20B—C21B177.9 (5)
N7A—C20A—C21A—C22A56.7 (8)N7B—C20B—C21B—C22B57.2 (7)
C20A—C21A—C22A—C23A55.4 (8)C20B—C21B—C22B—C23B54.0 (8)
C20A—C21A—C22A—C25A179.3 (7)C20B—C21B—C22B—C25B177.6 (6)
C25A—C22A—C23A—C24A177.9 (6)C21B—C22B—C23B—C24B53.5 (8)
C21A—C22A—C23A—C24A55.0 (8)C25B—C22B—C23B—C24B177.2 (7)
C20A—N7A—C24A—C23A57.1 (7)C20B—N7B—C24B—C23B57.3 (7)
C19A—N7A—C24A—C23A179.9 (6)C19B—N7B—C24B—C23B177.4 (6)
C22A—C23A—C24A—N7A57.3 (8)C22B—C23B—C24B—N7B56.9 (8)
N4A—C16A—C26A—C31A149.4 (6)N4B—C16B—C26B—C27B18.2 (8)
C15A—C16A—C26A—C31A32.5 (10)C15B—C16B—C26B—C27B160.2 (7)
N4A—C16A—C26A—C27A27.5 (8)N4B—C16B—C26B—C31B160.2 (6)
C15A—C16A—C26A—C27A150.6 (7)C15B—C16B—C26B—C31B21.5 (11)
C31A—C26A—C27A—C28A0.7 (11)C31B—C26B—C27B—C28B0.1 (10)
C16A—C26A—C27A—C28A176.4 (7)C16B—C26B—C27B—C28B178.4 (6)
C26A—C27A—C28A—C29A0.5 (13)C26B—C27B—C28B—C29B1.0 (11)
C27A—C28A—C29A—C30A1.5 (12)C27B—C28B—C29B—C30B2.5 (11)
C27A—C28A—C29A—Br1A178.2 (6)C27B—C28B—C29B—Br1B178.4 (5)
C28A—C29A—C30A—C31A1.3 (11)C28B—C29B—C30B—C31B3.2 (12)
Br1A—C29A—C30A—C31A178.5 (5)Br1B—C29B—C30B—C31B177.7 (6)
C29A—C30A—C31A—C26A0.0 (10)C29B—C30B—C31B—C26B2.3 (11)
C27A—C26A—C31A—C30A0.9 (9)C27B—C26B—C31B—C30B0.7 (10)
C16A—C26A—C31A—C30A176.0 (6)C16B—C26B—C31B—C30B177.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7A—H7A···O1Ai0.911.872.730 (6)156
N7A—H7A···N5A0.912.543.083 (8)119
N7B—H7B···O4Bi0.912.183.060 (6)161
N7B—H7B···N5B0.912.513.047 (7)118
C21A—H21A···O1Ai0.972.503.207 (9)129
C19A—H19A···O4A0.972.493.382 (9)154
C31A—H31A···O4A0.932.433.272 (11)151
C24A—H24A···O5A0.972.393.245 (9)147
C17A—H17A···O6Aii0.962.513.363 (11)147
C24B—H24C···O1B0.972.363.255 (8)153
C24B—H24C···O2B0.972.583.348 (14)136
C30B—H30B···O7B0.932.623.313 (11)132
C24A—H24B···F1A0.972.633.290 (10)126
C24B—H24D···F1B0.972.703.391 (9)128
C25A—H25A···F1Aiii0.962.523.283 (9)136
C28A—H28A···F1Biv0.932.673.558 (11)160
C28B—H28B···F2Aii0.932.773.441 (10)130
C3B—H3B···F3Bv0.932.843.419 (8)122
Symmetry codes: (i) x1, 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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