Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028297/hg2067sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028297/hg2067Isup2.hkl |
CCDC reference: 618221
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.093
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.99 Ratio PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.75 Ratio PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C25
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C23 - C24 .. 7.01 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C10
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm
3 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C27H34N42+·2Br−·H2O | Z = 2 |
Mr = 592.40 | F(000) = 608 |
Triclinic, P1 | Dx = 1.423 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7777 (4) Å | Cell parameters from 29997 reflections |
b = 12.0851 (7) Å | θ = 2.5–28.0° |
c = 14.4078 (7) Å | µ = 2.96 mm−1 |
α = 106.966 (4)° | T = 296 K |
β = 96.868 (4)° | Prism, colourless |
γ = 104.747 (4)° | 0.62 × 0.49 × 0.32 mm |
V = 1382.30 (13) Å3 |
Stoe IPDSII diffractometer | 5267 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long fine-focus | 4128 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.063 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.5° |
ω scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.261, Tmax = 0.451 | l = −17→17 |
25534 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3788P] where P = (Fo2 + 2Fc2)/3 |
5267 reflections | (Δ/σ)max = 0.001 |
317 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Experimental. Spectroscopic analysis: 1H NMR (DMSO-d6, δ, p.p.m.): 1.79 (d, CH3, 6H), 1.88 (d, CH3, 6H), 2.71 (m, bridge methylene, 2H), 4.82 (t, bridge methylene, 4H), 5.11 (d, NCH2, 4H), 5.50 (t, CH═, 2H), 7.71–8.32 (m, Ar—H, 8H), 10.01 (s, 2-CH, 2H); 13C NMR (DMSO-d6, δ, p.p.m.): 18.72, 22.48, 25.99, 28.90, 36.70, 44.44, 45.31, 114.30, 116.77, 127.02, 131.44, 131.77, 141.01, 142.48. Analysis calculated for C27H36N4Br2O: C 54.73, H 6.08, N 9.46%; found: C 54.84, H 6.09, N 9.60%. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
N1 | 0.5147 (3) | 0.5094 (2) | 0.19051 (17) | 0.0439 (7) | |
N2 | 0.2696 (3) | 0.4121 (2) | 0.10640 (17) | 0.0465 (7) | |
N3 | 0.8561 (3) | 0.7182 (2) | 0.48086 (17) | 0.0447 (7) | |
N4 | 0.7582 (3) | 0.8499 (3) | 0.57274 (18) | 0.0550 (9) | |
C1 | 0.5273 (3) | 0.4326 (3) | 0.1007 (2) | 0.0450 (8) | |
C2 | 0.6607 (4) | 0.4136 (3) | 0.0623 (2) | 0.0537 (10) | |
C3 | 0.6285 (4) | 0.3297 (3) | −0.0310 (3) | 0.0646 (11) | |
C4 | 0.4708 (5) | 0.2665 (3) | −0.0845 (2) | 0.0669 (11) | |
C5 | 0.3388 (4) | 0.2859 (3) | −0.0476 (2) | 0.0581 (10) | |
C6 | 0.3706 (3) | 0.3699 (3) | 0.0476 (2) | 0.0464 (9) | |
C7 | 0.3596 (3) | 0.4947 (3) | 0.1903 (2) | 0.0472 (8) | |
C8 | 0.0905 (4) | 0.3725 (3) | 0.0805 (2) | 0.0563 (10) | |
C9 | 0.0204 (4) | 0.2460 (3) | 0.0776 (3) | 0.0677 (11) | |
C10 | −0.0267 (5) | 0.2126 (4) | 0.1527 (3) | 0.0823 (16) | |
C11 | −0.0923 (8) | 0.0812 (6) | 0.1421 (5) | 0.128 (3) | |
C12 | −0.0117 (10) | 0.2998 (7) | 0.2519 (4) | 0.149 (3) | |
C13 | 0.6499 (3) | 0.5937 (3) | 0.2704 (2) | 0.0470 (8) | |
C14 | 0.7111 (4) | 0.5303 (3) | 0.3372 (2) | 0.0497 (9) | |
C15 | 0.8681 (4) | 0.6067 (3) | 0.4104 (2) | 0.0514 (9) | |
C16 | 0.9840 (3) | 0.8235 (3) | 0.5294 (2) | 0.0431 (8) | |
C17 | 1.1470 (3) | 0.8504 (3) | 0.5273 (3) | 0.0551 (10) | |
C18 | 1.2414 (4) | 0.9662 (3) | 0.5853 (3) | 0.0651 (11) | |
C19 | 1.1787 (4) | 1.0497 (3) | 0.6411 (3) | 0.0646 (11) | |
C20 | 1.0192 (4) | 1.0244 (3) | 0.6438 (2) | 0.0601 (11) | |
C21 | 0.9222 (3) | 0.9078 (3) | 0.5871 (2) | 0.0472 (9) | |
C22 | 0.7243 (3) | 0.7377 (3) | 0.5100 (2) | 0.0523 (9) | |
C23 | 0.6374 (5) | 0.9079 (5) | 0.6137 (3) | 0.0763 (14) | |
C24 | 0.6703 (6) | 0.9618 (4) | 0.7220 (4) | 0.0850 (16) | |
C25 | 0.6083 (5) | 0.9017 (4) | 0.7841 (3) | 0.0736 (12) | |
C26 | 0.6463 (9) | 0.9612 (7) | 0.8888 (4) | 0.139 (3) | |
C27 | 0.5209 (14) | 0.7702 (8) | 0.7420 (6) | 0.215 (5) | |
O1 | 0.4199 (3) | 0.7949 (3) | 0.3473 (3) | 0.0804 (10) | |
Br1 | 0.31028 (4) | 0.57545 (3) | 0.44246 (2) | 0.0606 (1) | |
Br2 | 1.05482 (4) | 0.68991 (3) | 0.19576 (2) | 0.0577 (1) | |
H2 | 0.76560 | 0.45540 | 0.09800 | 0.0640* | |
H3 | 0.71400 | 0.31440 | −0.05950 | 0.0770* | |
H4 | 0.45470 | 0.20950 | −0.14710 | 0.0800* | |
H5 | 0.23420 | 0.24510 | −0.08410 | 0.0700* | |
H7 | 0.31980 | 0.53670 | 0.24190 | 0.0570* | |
H8A | 0.05100 | 0.42640 | 0.12900 | 0.0670* | |
H8B | 0.05560 | 0.37850 | 0.01610 | 0.0670* | |
H9 | 0.00800 | 0.18440 | 0.01820 | 0.0810* | |
H11A | −0.12600 | 0.03310 | 0.07290 | 0.1910* | |
H11B | −0.18280 | 0.07020 | 0.17350 | 0.1910* | |
H11C | −0.01020 | 0.05620 | 0.17300 | 0.1910* | |
H12A | 0.06860 | 0.29190 | 0.29880 | 0.2240* | |
H12B | −0.11330 | 0.28350 | 0.27180 | 0.2240* | |
H12C | 0.01940 | 0.38100 | 0.24960 | 0.2240* | |
H13A | 0.61580 | 0.65940 | 0.30980 | 0.0560* | |
H13B | 0.73680 | 0.62850 | 0.24190 | 0.0560* | |
H14A | 0.62950 | 0.50770 | 0.37380 | 0.0600* | |
H14B | 0.72600 | 0.45620 | 0.29590 | 0.0600* | |
H15A | 0.90200 | 0.55850 | 0.44720 | 0.0620* | |
H15B | 0.95030 | 0.62850 | 0.37390 | 0.0620* | |
H17 | 1.18960 | 0.79410 | 0.48920 | 0.0660* | |
H18 | 1.35140 | 0.98840 | 0.58660 | 0.0780* | |
H19 | 1.24780 | 1.12660 | 0.67850 | 0.0770* | |
H20 | 0.97770 | 1.08190 | 0.68150 | 0.0720* | |
H22 | 0.62250 | 0.68060 | 0.48930 | 0.0630* | |
H23A | 0.63200 | 0.97070 | 0.58530 | 0.0920* | |
H23B | 0.53240 | 0.84700 | 0.59190 | 0.0920* | |
H24 | 0.73710 | 1.04150 | 0.75090 | 0.1020* | |
H26A | 0.75840 | 0.97520 | 0.91370 | 0.2080* | |
H26B | 0.58220 | 0.91100 | 0.91950 | 0.2080* | |
H26C | 0.62380 | 1.03750 | 0.90370 | 0.2080* | |
H27A | 0.40700 | 0.75820 | 0.73100 | 0.3220* | |
H27B | 0.54940 | 0.73080 | 0.78750 | 0.3220* | |
H27C | 0.54980 | 0.73620 | 0.68010 | 0.3220* | |
H1A | 0.396 (6) | 0.769 (5) | 0.390 (4) | 0.0870* | |
H1B | 0.333 (6) | 0.779 (4) | 0.310 (4) | 0.0870* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0405 (12) | 0.0429 (12) | 0.0404 (12) | 0.0054 (9) | 0.0087 (9) | 0.0089 (10) |
N2 | 0.0415 (12) | 0.0485 (13) | 0.0431 (12) | 0.0097 (10) | 0.0082 (10) | 0.0096 (10) |
N3 | 0.0377 (11) | 0.0508 (13) | 0.0408 (12) | 0.0093 (10) | 0.0075 (9) | 0.0125 (10) |
N4 | 0.0440 (13) | 0.0729 (18) | 0.0441 (13) | 0.0181 (12) | 0.0116 (11) | 0.0127 (12) |
C1 | 0.0473 (15) | 0.0443 (15) | 0.0404 (14) | 0.0107 (12) | 0.0102 (12) | 0.0123 (11) |
C2 | 0.0480 (16) | 0.0590 (18) | 0.0514 (17) | 0.0131 (14) | 0.0144 (13) | 0.0157 (14) |
C3 | 0.066 (2) | 0.071 (2) | 0.0579 (19) | 0.0267 (17) | 0.0260 (17) | 0.0131 (16) |
C4 | 0.075 (2) | 0.071 (2) | 0.0439 (17) | 0.0244 (18) | 0.0125 (16) | 0.0018 (15) |
C5 | 0.0603 (18) | 0.0594 (19) | 0.0396 (15) | 0.0121 (15) | 0.0018 (13) | 0.0034 (13) |
C6 | 0.0468 (15) | 0.0454 (15) | 0.0432 (15) | 0.0132 (12) | 0.0073 (12) | 0.0111 (12) |
C7 | 0.0473 (15) | 0.0474 (15) | 0.0417 (14) | 0.0104 (12) | 0.0114 (12) | 0.0102 (12) |
C8 | 0.0417 (15) | 0.067 (2) | 0.0548 (18) | 0.0132 (14) | 0.0066 (13) | 0.0168 (15) |
C9 | 0.0555 (18) | 0.065 (2) | 0.063 (2) | 0.0018 (16) | 0.0087 (16) | 0.0087 (17) |
C10 | 0.065 (2) | 0.087 (3) | 0.082 (3) | −0.002 (2) | 0.0012 (19) | 0.037 (2) |
C11 | 0.128 (5) | 0.113 (4) | 0.129 (5) | −0.007 (4) | 0.005 (4) | 0.067 (4) |
C12 | 0.196 (7) | 0.140 (6) | 0.083 (4) | −0.005 (5) | 0.050 (4) | 0.036 (4) |
C13 | 0.0466 (15) | 0.0415 (14) | 0.0412 (14) | 0.0023 (12) | 0.0062 (12) | 0.0076 (11) |
C14 | 0.0501 (15) | 0.0406 (15) | 0.0488 (16) | 0.0054 (12) | 0.0047 (13) | 0.0106 (12) |
C15 | 0.0458 (15) | 0.0514 (17) | 0.0506 (16) | 0.0140 (13) | 0.0055 (12) | 0.0101 (13) |
C16 | 0.0392 (13) | 0.0466 (15) | 0.0408 (14) | 0.0105 (11) | 0.0034 (11) | 0.0148 (12) |
C17 | 0.0383 (14) | 0.0587 (18) | 0.068 (2) | 0.0146 (13) | 0.0087 (14) | 0.0221 (15) |
C18 | 0.0434 (16) | 0.064 (2) | 0.082 (2) | 0.0070 (15) | 0.0020 (16) | 0.0286 (18) |
C19 | 0.0583 (19) | 0.0508 (18) | 0.070 (2) | 0.0030 (15) | −0.0087 (16) | 0.0193 (16) |
C20 | 0.069 (2) | 0.0555 (18) | 0.0493 (17) | 0.0202 (16) | 0.0018 (15) | 0.0112 (14) |
C21 | 0.0460 (15) | 0.0545 (17) | 0.0412 (14) | 0.0166 (13) | 0.0059 (12) | 0.0166 (12) |
C22 | 0.0393 (14) | 0.0673 (19) | 0.0426 (15) | 0.0087 (13) | 0.0104 (12) | 0.0129 (14) |
C23 | 0.064 (2) | 0.105 (3) | 0.063 (2) | 0.041 (2) | 0.0229 (18) | 0.016 (2) |
C24 | 0.089 (3) | 0.065 (2) | 0.090 (3) | 0.013 (2) | 0.031 (2) | 0.014 (2) |
C25 | 0.080 (2) | 0.061 (2) | 0.067 (2) | 0.0087 (18) | 0.0046 (19) | 0.0183 (18) |
C26 | 0.148 (6) | 0.158 (6) | 0.087 (4) | 0.032 (5) | 0.033 (4) | 0.017 (4) |
C27 | 0.308 (12) | 0.123 (6) | 0.123 (6) | −0.072 (7) | 0.035 (7) | 0.032 (5) |
O1 | 0.0546 (14) | 0.0775 (18) | 0.098 (2) | 0.0044 (13) | 0.0064 (14) | 0.0305 (16) |
Br1 | 0.0486 (2) | 0.0792 (2) | 0.0579 (2) | 0.0162 (2) | 0.0131 (1) | 0.0308 (2) |
Br2 | 0.0486 (2) | 0.0633 (2) | 0.0529 (2) | 0.0133 (1) | 0.0123 (1) | 0.0100 (1) |
O1—H1B | 0.82 (5) | C25—C26 | 1.424 (7) |
O1—H1A | 0.79 (6) | C2—H2 | 0.9300 |
N1—C7 | 1.327 (4) | C3—H3 | 0.9300 |
N1—C1 | 1.391 (4) | C4—H4 | 0.9300 |
N1—C13 | 1.464 (4) | C5—H5 | 0.9300 |
N2—C7 | 1.322 (4) | C7—H7 | 0.9300 |
N2—C6 | 1.386 (4) | C8—H8A | 0.9700 |
N2—C8 | 1.487 (4) | C8—H8B | 0.9700 |
N3—C22 | 1.330 (4) | C9—H9 | 0.9300 |
N3—C15 | 1.469 (4) | C11—H11A | 0.9600 |
N3—C16 | 1.391 (4) | C11—H11B | 0.9600 |
N4—C22 | 1.326 (5) | C11—H11C | 0.9600 |
N4—C23 | 1.500 (6) | C12—H12A | 0.9600 |
N4—C21 | 1.392 (4) | C12—H12C | 0.9600 |
C1—C2 | 1.396 (5) | C12—H12B | 0.9600 |
C1—C6 | 1.390 (4) | C13—H13B | 0.9700 |
C2—C3 | 1.372 (5) | C13—H13A | 0.9700 |
C3—C4 | 1.399 (6) | C14—H14A | 0.9700 |
C4—C5 | 1.376 (6) | C14—H14B | 0.9700 |
C5—C6 | 1.393 (4) | C15—H15A | 0.9700 |
C8—C9 | 1.482 (5) | C15—H15B | 0.9700 |
C9—C10 | 1.335 (6) | C17—H17 | 0.9300 |
C10—C12 | 1.475 (7) | C18—H18 | 0.9300 |
C10—C11 | 1.500 (9) | C19—H19 | 0.9300 |
C13—C14 | 1.523 (5) | C20—H20 | 0.9300 |
C14—C15 | 1.517 (5) | C22—H22 | 0.9300 |
C16—C21 | 1.385 (4) | C23—H23B | 0.9700 |
C16—C17 | 1.390 (4) | C23—H23A | 0.9700 |
C17—C18 | 1.380 (5) | C24—H24 | 0.9300 |
C18—C19 | 1.372 (5) | C26—H26B | 0.9600 |
C19—C20 | 1.363 (5) | C26—H26C | 0.9600 |
C20—C21 | 1.389 (5) | C26—H26A | 0.9600 |
C23—C24 | 1.465 (7) | C27—H27C | 0.9600 |
C24—C25 | 1.385 (7) | C27—H27A | 0.9600 |
C25—C27 | 1.479 (11) | C27—H27B | 0.9600 |
Br1···C22 | 3.523 (3) | H2···Br2 | 3.1000 |
Br1···O1 | 3.313 (4) | H2···C13 | 3.0100 |
Br1···C15i | 3.682 (3) | H2···H13B | 2.5700 |
Br1···C7 | 3.586 (3) | H3···Br2vi | 2.9900 |
Br2···O1ii | 3.360 (3) | H5···C8 | 3.0300 |
Br1···H22 | 2.6200 | H5···Br2v | 3.2300 |
Br1···H17iii | 3.0200 | H7···Br1 | 2.8000 |
Br1···H1A | 2.62 (6) | H7···O1 | 2.8900 |
Br1···H7 | 2.8000 | H7···H8A | 2.4900 |
Br1···H14Ai | 3.1300 | H7···H13A | 2.5500 |
Br1···H15Ai | 3.0500 | H8A···Br2iii | 3.0400 |
Br2···H15B | 3.0500 | H8A···C12 | 2.6800 |
Br2···H13B | 2.9100 | H8A···H7 | 2.4900 |
Br2···H1Bii | 2.55 (5) | H8A···H12C | 2.0000 |
Br2···H2 | 3.1000 | H8B···Br2v | 2.8900 |
Br2···H8Aii | 3.0400 | H9···H11A | 2.3100 |
Br2···H24iv | 3.1100 | H11A···C26ix | 2.8800 |
Br2···H5v | 3.2300 | H11A···H9 | 2.3100 |
Br2···H8Bv | 2.8900 | H11A···H26Aix | 2.2200 |
Br2···H3vi | 2.9900 | H11B···H12B | 2.4300 |
Br2···H20iv | 2.9100 | H11C···C20i | 3.0700 |
O1···Br2iii | 3.360 (3) | H12B···H11B | 2.4300 |
O1···C18iv | 3.380 (5) | H12B···H27Ax | 2.4900 |
O1···Br1 | 3.313 (4) | H12C···C8 | 2.5700 |
O1···H7 | 2.8900 | H12C···H8A | 2.0000 |
O1···H18iv | 2.6800 | H13A···H19iv | 2.5000 |
O1···H13A | 2.6600 | H13A···O1 | 2.6600 |
O1···H23Avii | 2.8900 | H13A···N3 | 2.8300 |
N1···N2 | 2.176 (4) | H13A···C22 | 2.7200 |
N2···N1 | 2.176 (4) | H13A···H7 | 2.5500 |
N3···N4 | 2.182 (4) | H13A···H22 | 2.5200 |
N4···N3 | 2.182 (4) | H13B···H2 | 2.5700 |
N1···H27Bi | 2.9300 | H13B···Br2 | 2.9100 |
N3···H13A | 2.8300 | H13B···C2 | 2.9400 |
N4···H27C | 2.8700 | H13B···H15B | 2.5100 |
C2···C6v | 3.480 (5) | H14A···Br1i | 3.1300 |
C3···C7v | 3.545 (5) | H14A···C22 | 2.7400 |
C5···C9 | 3.511 (5) | H14A···H22 | 2.2800 |
C6···C2v | 3.480 (5) | H14B···C1 | 3.0200 |
C7···Br1 | 3.586 (3) | H14B···C27i | 2.8800 |
C7···C3v | 3.545 (5) | H14B···H27Ai | 2.4500 |
C9···C5 | 3.511 (5) | H15A···Br1i | 3.0500 |
C13···C22 | 3.278 (4) | H15B···H17 | 2.5000 |
C14···C27i | 3.449 (11) | H15B···Br2 | 3.0500 |
C15···Br1i | 3.682 (3) | H15B···C17 | 2.8900 |
C16···C20iv | 3.506 (5) | H15B···H13B | 2.5100 |
C16···C19iv | 3.591 (5) | H17···H1Aii | 2.4600 |
C17···C20iv | 3.597 (5) | H17···Br1ii | 3.0200 |
C18···O1iv | 3.380 (5) | H17···C15 | 2.9800 |
C19···C21iv | 3.518 (5) | H17···H15B | 2.5000 |
C19···C16iv | 3.591 (5) | H18···O1iv | 2.6800 |
C20···C16iv | 3.506 (5) | H18···C23ii | 2.9400 |
C20···C17iv | 3.597 (5) | H18···H23Aii | 2.5300 |
C20···C24 | 3.371 (6) | H19···H13Aiv | 2.5000 |
C21···C19iv | 3.518 (5) | H20···C24 | 2.9300 |
C22···C13 | 3.278 (4) | H20···C23 | 3.0300 |
C22···Br1 | 3.523 (3) | H20···H24 | 2.4400 |
C24···C20 | 3.371 (6) | H20···Br2iv | 2.9100 |
C27···C14i | 3.449 (11) | H22···Br1 | 2.6200 |
C1···H14B | 3.0200 | H22···C13 | 3.0800 |
C1···H27Bi | 2.9000 | H22···C14 | 2.7400 |
C2···H13B | 2.9400 | H22···H13A | 2.5200 |
C6···H27Bi | 3.0600 | H22···H14A | 2.2800 |
C8···H5 | 3.0300 | H22···H23B | 2.4900 |
C8···H12C | 2.5700 | H23A···H18iii | 2.5300 |
C12···H8A | 2.6800 | H23A···O1vii | 2.8900 |
C13···H2 | 3.0100 | H23A···C18iv | 3.0300 |
C13···H22 | 3.0800 | H23B···C27 | 2.5900 |
C14···H22 | 2.7400 | H23B···H22 | 2.4900 |
C15···H17 | 2.9800 | H23B···H27C | 2.1200 |
C17···H15B | 2.8900 | H24···C20 | 3.0900 |
C18···H23Aiv | 3.0300 | H24···H20 | 2.4400 |
C20···H11Ci | 3.0700 | H24···H26C | 2.5300 |
C20···H24 | 3.0900 | H24···Br2iv | 3.1100 |
C22···H14A | 2.7400 | H26A···H11Aviii | 2.2200 |
C22···H27C | 3.0400 | H26B···H27B | 2.3600 |
C22···H13A | 2.7200 | H26C···H24 | 2.5300 |
C23···H27C | 2.5200 | H27A···H12Bx | 2.4900 |
C23···H18iii | 2.9400 | H27A···H14Bi | 2.4500 |
C23···H20 | 3.0300 | H27B···H26B | 2.3600 |
C24···H20 | 2.9300 | H27B···N1i | 2.9300 |
C26···H11Aviii | 2.8800 | H27B···C1i | 2.9000 |
C27···H14Bi | 2.8800 | H27B···C6i | 3.0600 |
C27···H23B | 2.5900 | H27C···N4 | 2.8700 |
H1A···Br1 | 2.62 (6) | H27C···C22 | 3.0400 |
H1A···H17iii | 2.4600 | H27C···C23 | 2.5200 |
H1B···Br2iii | 2.55 (5) | H27C···H23B | 2.1200 |
H1A—O1—H1B | 104 (5) | H8A—C8—H8B | 108.00 |
C1—N1—C7 | 108.2 (2) | N2—C8—H8A | 109.00 |
C7—N1—C13 | 126.1 (2) | C8—C9—H9 | 117.00 |
C1—N1—C13 | 125.7 (3) | C10—C9—H9 | 117.00 |
C6—N2—C7 | 108.4 (3) | C10—C11—H11B | 109.00 |
C7—N2—C8 | 125.3 (2) | C10—C11—H11C | 110.00 |
C6—N2—C8 | 126.4 (2) | C10—C11—H11A | 109.00 |
C15—N3—C16 | 125.2 (3) | H11A—C11—H11C | 110.00 |
C15—N3—C22 | 127.2 (3) | H11B—C11—H11C | 109.00 |
C16—N3—C22 | 107.7 (2) | H11A—C11—H11B | 109.00 |
C21—N4—C22 | 108.5 (3) | C10—C12—H12A | 110.00 |
C21—N4—C23 | 125.8 (3) | C10—C12—H12C | 109.00 |
C22—N4—C23 | 125.5 (3) | H12A—C12—H12B | 110.00 |
N1—C1—C6 | 106.3 (2) | C10—C12—H12B | 109.00 |
C2—C1—C6 | 121.9 (3) | H12B—C12—H12C | 109.00 |
N1—C1—C2 | 131.8 (3) | H12A—C12—H12C | 109.00 |
C1—C2—C3 | 116.3 (3) | N1—C13—H13B | 109.00 |
C2—C3—C4 | 121.9 (3) | C14—C13—H13A | 109.00 |
C3—C4—C5 | 122.2 (3) | N1—C13—H13A | 109.00 |
C4—C5—C6 | 116.2 (3) | H13A—C13—H13B | 108.00 |
N2—C6—C5 | 131.8 (3) | C14—C13—H13B | 109.00 |
C1—C6—C5 | 121.5 (3) | C13—C14—H14A | 109.00 |
N2—C6—C1 | 106.7 (2) | C15—C14—H14A | 109.00 |
N1—C7—N2 | 110.5 (3) | C15—C14—H14B | 109.00 |
N2—C8—C9 | 111.9 (3) | H14A—C14—H14B | 108.00 |
C8—C9—C10 | 125.8 (4) | C13—C14—H14B | 109.00 |
C9—C10—C11 | 121.2 (4) | N3—C15—H15B | 109.00 |
C11—C10—C12 | 115.4 (5) | C14—C15—H15A | 109.00 |
C9—C10—C12 | 123.3 (5) | N3—C15—H15A | 109.00 |
N1—C13—C14 | 111.5 (3) | H15A—C15—H15B | 108.00 |
C13—C14—C15 | 114.0 (3) | C14—C15—H15B | 109.00 |
N3—C15—C14 | 113.3 (3) | C18—C17—H17 | 122.00 |
N3—C16—C17 | 131.1 (3) | C16—C17—H17 | 122.00 |
C17—C16—C21 | 121.7 (3) | C17—C18—H18 | 119.00 |
N3—C16—C21 | 107.2 (3) | C19—C18—H18 | 119.00 |
C16—C17—C18 | 115.6 (3) | C20—C19—H19 | 119.00 |
C17—C18—C19 | 122.3 (3) | C18—C19—H19 | 119.00 |
C18—C19—C20 | 122.6 (4) | C19—C20—H20 | 122.00 |
C19—C20—C21 | 116.1 (3) | C21—C20—H20 | 122.00 |
N4—C21—C16 | 106.1 (3) | N4—C22—H22 | 125.00 |
C16—C21—C20 | 121.7 (3) | N3—C22—H22 | 125.00 |
N4—C21—C20 | 132.2 (3) | N4—C23—H23A | 108.00 |
N3—C22—N4 | 110.5 (3) | C24—C23—H23A | 108.00 |
N4—C23—C24 | 115.4 (4) | C24—C23—H23B | 109.00 |
C23—C24—C25 | 124.2 (5) | N4—C23—H23B | 108.00 |
C24—C25—C27 | 119.1 (5) | H23A—C23—H23B | 107.00 |
C26—C25—C27 | 119.9 (6) | C25—C24—H24 | 118.00 |
C24—C25—C26 | 120.5 (5) | C23—C24—H24 | 118.00 |
C3—C2—H2 | 122.00 | C25—C26—H26A | 109.00 |
C1—C2—H2 | 122.00 | C25—C26—H26B | 109.00 |
C2—C3—H3 | 119.00 | H26A—C26—H26B | 109.00 |
C4—C3—H3 | 119.00 | H26A—C26—H26C | 109.00 |
C5—C4—H4 | 119.00 | C25—C26—H26C | 109.00 |
C3—C4—H4 | 119.00 | H26B—C26—H26C | 109.00 |
C4—C5—H5 | 122.00 | C25—C27—H27B | 109.00 |
C6—C5—H5 | 122.00 | C25—C27—H27C | 109.00 |
N1—C7—H7 | 125.00 | C25—C27—H27A | 110.00 |
N2—C7—H7 | 125.00 | H27A—C27—H27C | 109.00 |
N2—C8—H8B | 109.00 | H27B—C27—H27C | 109.00 |
C9—C8—H8A | 109.00 | H27A—C27—H27B | 110.00 |
C9—C8—H8B | 109.00 | ||
C7—N1—C1—C2 | 178.9 (4) | C22—N4—C21—C16 | −0.1 (4) |
C13—N1—C1—C2 | 0.1 (6) | N1—C1—C6—C5 | 178.9 (3) |
C7—N1—C1—C6 | −0.9 (4) | C2—C1—C6—N2 | −179.0 (3) |
C13—N1—C1—C6 | −179.7 (3) | N1—C1—C2—C3 | −179.6 (4) |
C1—N1—C7—N2 | 0.7 (4) | C6—C1—C2—C3 | 0.2 (5) |
C13—N1—C7—N2 | 179.5 (3) | C2—C1—C6—C5 | −1.0 (5) |
C1—N1—C13—C14 | −84.0 (4) | N1—C1—C6—N2 | 0.8 (4) |
C7—N1—C13—C14 | 97.4 (4) | C1—C2—C3—C4 | −0.2 (5) |
C6—N2—C8—C9 | 69.2 (4) | C2—C3—C4—C5 | 1.0 (6) |
C7—N2—C8—C9 | −111.1 (4) | C3—C4—C5—C6 | −1.7 (5) |
C7—N2—C6—C5 | −178.2 (4) | C4—C5—C6—N2 | 179.2 (3) |
C8—N2—C6—C5 | 1.6 (6) | C4—C5—C6—C1 | 1.7 (5) |
C7—N2—C6—C1 | −0.4 (4) | N2—C8—C9—C10 | 93.3 (4) |
C6—N2—C7—N1 | −0.2 (4) | C8—C9—C10—C12 | −1.3 (8) |
C8—N2—C7—N1 | −180.0 (3) | C8—C9—C10—C11 | −178.4 (5) |
C8—N2—C6—C1 | 179.4 (3) | N1—C13—C14—C15 | 170.1 (2) |
C22—N3—C16—C17 | 178.3 (4) | C13—C14—C15—N3 | 62.0 (3) |
C16—N3—C22—N4 | 1.3 (3) | N3—C16—C21—N4 | 0.9 (3) |
C16—N3—C15—C14 | −154.7 (3) | N3—C16—C17—C18 | 179.7 (3) |
C22—N3—C15—C14 | 25.3 (4) | C21—C16—C17—C18 | −0.7 (5) |
C15—N3—C16—C21 | 178.7 (3) | C17—C16—C21—C20 | 1.7 (5) |
C22—N3—C16—C21 | −1.4 (3) | N3—C16—C21—C20 | −178.6 (3) |
C15—N3—C22—N4 | −178.7 (3) | C17—C16—C21—N4 | −178.8 (3) |
C15—N3—C16—C17 | −1.7 (5) | C16—C17—C18—C19 | −0.3 (6) |
C23—N4—C21—C20 | 4.5 (6) | C17—C18—C19—C20 | 0.3 (6) |
C21—N4—C23—C24 | −58.5 (6) | C18—C19—C20—C21 | 0.6 (5) |
C22—N4—C23—C24 | 127.6 (4) | C19—C20—C21—N4 | 179.1 (3) |
C23—N4—C22—N3 | 174.1 (3) | C19—C20—C21—C16 | −1.5 (5) |
C23—N4—C21—C16 | −174.9 (3) | N4—C23—C24—C25 | −93.3 (6) |
C22—N4—C21—C20 | 179.4 (3) | C23—C24—C25—C26 | −179.9 (6) |
C21—N4—C22—N3 | −0.8 (4) | C23—C24—C25—C27 | 8.5 (9) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+2, −y+2, −z+1; (v) −x+1, −y+1, −z; (vi) −x+2, −y+1, −z; (vii) −x+1, −y+2, −z+1; (viii) x+1, y+1, z+1; (ix) x−1, y−1, z−1; (x) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Br1 | 0.79 (6) | 2.62 (6) | 3.313 (4) | 146 (5) |
O1—H1B···Br2iii | 0.82 (5) | 2.55 (5) | 3.360 (3) | 169 (5) |
C7—H7···Br1 | 0.93 | 2.80 | 3.586 (3) | 142 |
C8—H8B···Br2v | 0.97 | 2.89 | 3.819 (3) | 160 |
C13—H13B···Br2 | 0.97 | 2.91 | 3.832 (3) | 159 |
C20—H20···Br2iv | 0.93 | 2.91 | 3.812 (3) | 163 |
C22—H22···Br1 | 0.93 | 2.62 | 3.523 (3) | 164 |
Symmetry codes: (iii) x−1, y, z; (iv) −x+2, −y+2, −z+1; (v) −x+1, −y+1, −z. |
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