The title compound, C
21H
21N
2O
+·Br
−·0.5H
2O, crystallizes in a monoclinic unit cell with two cations, two anions and one water molecule in the asymmetric unit. The conformations of the two independent cations are different. The crystal packing is stabilized by O—H
Br and C—H
Br interactions and weak intermolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 270282
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.056
- wR factor = 0.140
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. BR2 .. 2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B .. O1B .. 2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A .. O1# .. 2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21A .. O1# .. 2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B .. BR1 .. 2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21B .. O1# .. 2.85 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C21B .. O1# .. 3.77 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
8 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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 and PARST (Nardelli, 1995).
1-[2-(Biphenyl-4-yl)-2-oxoethyl]-4-(
N,
N-dimethylamino)pyridinium
bromide hemihydrate
top
Crystal data top
C21H21N2O+·Br−·0.5H2O | F(000) = 3344 |
Mr = 406.32 | Dx = 1.384 Mg m−3 |
Monoclinic, C2/c | Melting point: 534 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 21.077 (6) Å | Cell parameters from 911 reflections |
b = 9.971 (3) Å | θ = 2.2–27.8° |
c = 37.485 (12) Å | µ = 2.12 mm−1 |
β = 98.121 (9)° | T = 298 K |
V = 7799 (4) Å3 | Block, colourless |
Z = 16 | 0.7 × 0.4 × 0.4 mm |
Data collection top
Bruker SMART CCD 1K diffractometer | 7982 independent reflections |
Radiation source: fine-focus sealed tube | 4222 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
ω scans | θmax = 26.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | h = −26→26 |
Tmin = 0.281, Tmax = 0.428 | k = 0→12 |
31162 measured reflections | l = 0→46 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0565P)2 + 4.0141P] where P = (Fo2 + 2Fc2)/3 |
7982 reflections | (Δ/σ)max = 0.001 |
471 parameters | Δρmax = 0.52 e Å−3 |
2 restraints | Δρmin = −0.34 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 | 0.13559 (18) | 0.9657 (4) | 0.25693 (9) | 0.0755 (10) | |
N1A | 0.18824 (16) | 0.7557 (3) | 0.29593 (9) | 0.0452 (9) | |
N2A | 0.13303 (16) | 0.7028 (3) | 0.39680 (9) | 0.0472 (9) | |
C1A | 0.2048 (2) | 0.7788 (4) | 0.26010 (10) | 0.0489 (11) | |
H1A | 0.1949 | 0.6989 | 0.2456 | 0.059* | |
H1B | 0.2506 | 0.7942 | 0.2620 | 0.059* | |
C2A | 0.1575 (2) | 0.6433 (4) | 0.30396 (11) | 0.0495 (11) | |
H2A | 0.1483 | 0.5781 | 0.2862 | 0.059* | |
C3A | 0.1396 (2) | 0.6217 (4) | 0.33656 (11) | 0.0493 (11) | |
H3A | 0.1186 | 0.5425 | 0.3408 | 0.059* | |
C4A | 0.15230 (19) | 0.7190 (4) | 0.36463 (11) | 0.0405 (10) | |
C5A | 0.1870 (2) | 0.8312 (4) | 0.35571 (11) | 0.0466 (11) | |
H5A | 0.1988 | 0.8964 | 0.3731 | 0.056* | |
C6A | 0.2038 (2) | 0.8468 (4) | 0.32267 (11) | 0.0490 (11) | |
H6A | 0.2269 | 0.9227 | 0.3179 | 0.059* | |
C7A | 0.0993 (2) | 0.5829 (5) | 0.40611 (13) | 0.0613 (13) | |
H7A | 0.0649 | 0.5633 | 0.3872 | 0.092* | |
H7B | 0.0822 | 0.5979 | 0.4282 | 0.092* | |
H7C | 0.1285 | 0.5086 | 0.4091 | 0.092* | |
C8A | 0.1473 (2) | 0.8030 (5) | 0.42517 (12) | 0.0691 (15) | |
H8A | 0.1916 | 0.8285 | 0.4270 | 0.104* | |
H8B | 0.1390 | 0.7659 | 0.4477 | 0.104* | |
H8C | 0.1207 | 0.8804 | 0.4194 | 0.104* | |
C9A | 0.1700 (2) | 0.8965 (5) | 0.24121 (12) | 0.0487 (11) | |
C10A | 0.18073 (19) | 0.9263 (4) | 0.20380 (10) | 0.0422 (10) | |
C11A | 0.2017 (2) | 0.8304 (4) | 0.18136 (11) | 0.0490 (11) | |
H11A | 0.2103 | 0.7439 | 0.1900 | 0.059* | |
C12A | 0.2099 (2) | 0.8613 (4) | 0.14657 (11) | 0.0475 (11) | |
H12A | 0.2237 | 0.7949 | 0.1320 | 0.057* | |
C13A | 0.19800 (18) | 0.9894 (4) | 0.13255 (11) | 0.0390 (10) | |
C14A | 0.1774 (2) | 1.0861 (4) | 0.15552 (11) | 0.0507 (12) | |
H14A | 0.1700 | 1.1734 | 0.1472 | 0.061* | |
C15A | 0.1679 (2) | 1.0545 (4) | 0.18996 (12) | 0.0507 (12) | |
H15A | 0.1527 | 1.1198 | 0.2043 | 0.061* | |
C16A | 0.20660 (19) | 1.0218 (4) | 0.09463 (11) | 0.0417 (10) | |
C17A | 0.2404 (2) | 0.9369 (5) | 0.07455 (11) | 0.0519 (12) | |
H17A | 0.2592 | 0.8598 | 0.0853 | 0.062* | |
C18A | 0.2469 (2) | 0.9641 (5) | 0.03914 (13) | 0.0596 (13) | |
H18A | 0.2697 | 0.9055 | 0.0264 | 0.072* | |
C19A | 0.2201 (3) | 1.0767 (5) | 0.02285 (13) | 0.0671 (14) | |
H19A | 0.2242 | 1.0949 | −0.0010 | 0.080* | |
C20A | 0.1868 (3) | 1.1632 (5) | 0.04200 (14) | 0.0736 (15) | |
H20A | 0.1689 | 1.2409 | 0.0311 | 0.088* | |
C21A | 0.1798 (2) | 1.1350 (5) | 0.07749 (12) | 0.0614 (13) | |
H21A | 0.1565 | 1.1935 | 0.0900 | 0.074* | |
O1B | −0.01892 (18) | 0.2592 (5) | 0.52468 (9) | 0.1119 (17) | |
N1B | 0.06795 (15) | 0.1783 (4) | 0.57855 (8) | 0.0442 (9) | |
N2B | 0.01245 (17) | 0.1691 (4) | 0.67933 (9) | 0.0564 (10) | |
C1B | 0.0864 (2) | 0.1828 (5) | 0.54266 (10) | 0.0507 (12) | |
H1C | 0.1002 | 0.0943 | 0.5362 | 0.061* | |
H1D | 0.1222 | 0.2438 | 0.5426 | 0.061* | |
C2B | 0.0396 (2) | 0.0691 (5) | 0.59020 (12) | 0.0544 (12) | |
H2B | 0.0328 | −0.0049 | 0.5750 | 0.065* | |
C3B | 0.0207 (2) | 0.0630 (5) | 0.62297 (12) | 0.0561 (12) | |
H3B | 0.0017 | −0.0148 | 0.6301 | 0.067* | |
C4B | 0.02954 (19) | 0.1729 (4) | 0.64659 (11) | 0.0438 (11) | |
C5B | 0.0579 (2) | 0.2860 (4) | 0.63336 (11) | 0.0473 (11) | |
H5B | 0.0643 | 0.3625 | 0.6476 | 0.057* | |
C6B | 0.0761 (2) | 0.2858 (4) | 0.60028 (11) | 0.0490 (11) | |
H6B | 0.0948 | 0.3626 | 0.5923 | 0.059* | |
C7B | −0.0153 (3) | 0.0508 (5) | 0.69323 (13) | 0.0812 (18) | |
H7D | −0.0484 | 0.0162 | 0.6754 | 0.122* | |
H7E | −0.0333 | 0.0738 | 0.7146 | 0.122* | |
H7F | 0.0173 | −0.0160 | 0.6990 | 0.122* | |
C8B | 0.0231 (3) | 0.2818 (6) | 0.70407 (13) | 0.0793 (17) | |
H8D | 0.0593 | 0.3327 | 0.6988 | 0.119* | |
H8E | 0.0312 | 0.2491 | 0.7284 | 0.119* | |
H8F | −0.0142 | 0.3381 | 0.7013 | 0.119* | |
C9B | 0.0312 (2) | 0.2286 (5) | 0.51502 (11) | 0.0562 (13) | |
C10B | 0.0418 (2) | 0.2351 (5) | 0.47694 (11) | 0.0491 (11) | |
C11B | 0.0976 (2) | 0.1906 (5) | 0.46524 (11) | 0.0537 (12) | |
H11B | 0.1302 | 0.1548 | 0.4818 | 0.064* | |
C12B | 0.1053 (2) | 0.1985 (4) | 0.42961 (11) | 0.0518 (12) | |
H12B | 0.1433 | 0.1679 | 0.4225 | 0.062* | |
C13B | 0.0581 (2) | 0.2511 (4) | 0.40381 (11) | 0.0404 (10) | |
C14B | 0.0027 (2) | 0.2965 (5) | 0.41609 (11) | 0.0513 (12) | |
H14B | −0.0299 | 0.3331 | 0.3997 | 0.062* | |
C15B | −0.0054 (2) | 0.2887 (5) | 0.45176 (12) | 0.0563 (13) | |
H15B | −0.0431 | 0.3200 | 0.4590 | 0.068* | |
C16B | 0.0662 (2) | 0.2610 (4) | 0.36521 (10) | 0.0410 (10) | |
C17B | 0.1226 (2) | 0.2189 (5) | 0.35321 (12) | 0.0585 (13) | |
H17B | 0.1557 | 0.1843 | 0.3697 | 0.070* | |
C18B | 0.1299 (3) | 0.2277 (5) | 0.31726 (13) | 0.0683 (15) | |
H18B | 0.1677 | 0.1982 | 0.3097 | 0.082* | |
C19B | 0.0820 (3) | 0.2795 (5) | 0.29278 (14) | 0.0712 (15) | |
H19B | 0.0872 | 0.2866 | 0.2686 | 0.085* | |
C20B | 0.0261 (3) | 0.3209 (5) | 0.30408 (13) | 0.0733 (15) | |
H20B | −0.0067 | 0.3559 | 0.2875 | 0.088* | |
C21B | 0.0181 (2) | 0.3112 (5) | 0.33941 (12) | 0.0595 (13) | |
H21B | −0.0204 | 0.3388 | 0.3465 | 0.071* | |
Br1 | 0.22209 (2) | 0.56541 (5) | 0.070795 (15) | 0.06631 (19) | |
Br2 | 0.15039 (2) | 0.46281 (5) | 0.213027 (13) | 0.06256 (18) | |
OW | 0.13357 (18) | 0.4124 (4) | 0.12488 (11) | 0.0674 (9) | |
H22 | 0.160 | 0.454 | 0.1134 | 0.08* | |
H23 | 0.139 | 0.438 | 0.1473 | 0.12* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.089 (3) | 0.087 (3) | 0.056 (2) | 0.029 (2) | 0.0285 (19) | 0.0054 (19) |
N1A | 0.048 (2) | 0.048 (2) | 0.040 (2) | −0.0078 (18) | 0.0068 (17) | 0.0006 (18) |
N2A | 0.048 (2) | 0.053 (2) | 0.043 (2) | −0.0067 (18) | 0.0118 (18) | −0.0027 (18) |
C1A | 0.049 (3) | 0.059 (3) | 0.040 (3) | −0.001 (2) | 0.011 (2) | 0.000 (2) |
C2A | 0.056 (3) | 0.048 (3) | 0.044 (3) | −0.005 (2) | 0.003 (2) | −0.008 (2) |
C3A | 0.054 (3) | 0.046 (3) | 0.048 (3) | −0.014 (2) | 0.007 (2) | −0.003 (2) |
C4A | 0.038 (3) | 0.038 (2) | 0.044 (3) | 0.000 (2) | 0.000 (2) | 0.002 (2) |
C5A | 0.052 (3) | 0.048 (3) | 0.040 (3) | −0.013 (2) | 0.006 (2) | −0.005 (2) |
C6A | 0.050 (3) | 0.049 (3) | 0.047 (3) | −0.014 (2) | 0.003 (2) | −0.001 (2) |
C7A | 0.063 (3) | 0.064 (3) | 0.059 (3) | −0.012 (3) | 0.018 (3) | 0.005 (2) |
C8A | 0.079 (4) | 0.076 (4) | 0.054 (3) | −0.018 (3) | 0.016 (3) | −0.014 (3) |
C9A | 0.048 (3) | 0.052 (3) | 0.046 (3) | −0.003 (2) | 0.005 (2) | −0.001 (2) |
C10A | 0.039 (3) | 0.050 (3) | 0.036 (2) | −0.004 (2) | 0.003 (2) | −0.003 (2) |
C11A | 0.055 (3) | 0.046 (3) | 0.047 (3) | 0.008 (2) | 0.011 (2) | 0.010 (2) |
C12A | 0.053 (3) | 0.043 (3) | 0.048 (3) | 0.009 (2) | 0.016 (2) | 0.000 (2) |
C13A | 0.035 (2) | 0.042 (3) | 0.040 (2) | −0.005 (2) | 0.0052 (19) | −0.001 (2) |
C14A | 0.064 (3) | 0.043 (3) | 0.046 (3) | −0.001 (2) | 0.008 (2) | 0.000 (2) |
C15A | 0.059 (3) | 0.049 (3) | 0.045 (3) | 0.002 (2) | 0.008 (2) | −0.010 (2) |
C16A | 0.038 (2) | 0.040 (3) | 0.047 (3) | −0.008 (2) | 0.004 (2) | −0.002 (2) |
C17A | 0.055 (3) | 0.055 (3) | 0.046 (3) | 0.004 (2) | 0.010 (2) | 0.003 (2) |
C18A | 0.061 (3) | 0.065 (3) | 0.056 (3) | 0.002 (3) | 0.019 (3) | −0.003 (3) |
C19A | 0.086 (4) | 0.069 (4) | 0.050 (3) | −0.004 (3) | 0.025 (3) | 0.006 (3) |
C20A | 0.097 (4) | 0.063 (3) | 0.062 (3) | 0.018 (3) | 0.016 (3) | 0.015 (3) |
C21A | 0.080 (4) | 0.050 (3) | 0.057 (3) | 0.016 (3) | 0.019 (3) | 0.010 (2) |
O1B | 0.058 (2) | 0.225 (5) | 0.058 (2) | 0.042 (3) | 0.023 (2) | 0.027 (3) |
N1B | 0.039 (2) | 0.060 (2) | 0.033 (2) | −0.0089 (18) | 0.0041 (16) | 0.0022 (18) |
N2B | 0.055 (2) | 0.075 (3) | 0.042 (2) | −0.024 (2) | 0.0157 (19) | −0.006 (2) |
C1B | 0.042 (3) | 0.070 (3) | 0.040 (3) | 0.000 (2) | 0.008 (2) | 0.005 (2) |
C2B | 0.068 (3) | 0.052 (3) | 0.042 (3) | −0.014 (3) | 0.003 (2) | −0.008 (2) |
C3B | 0.063 (3) | 0.059 (3) | 0.047 (3) | −0.021 (3) | 0.010 (2) | 0.002 (2) |
C4B | 0.033 (2) | 0.060 (3) | 0.038 (3) | −0.011 (2) | 0.004 (2) | 0.001 (2) |
C5B | 0.053 (3) | 0.050 (3) | 0.041 (3) | −0.010 (2) | 0.012 (2) | −0.004 (2) |
C6B | 0.052 (3) | 0.052 (3) | 0.044 (3) | −0.012 (2) | 0.010 (2) | 0.006 (2) |
C7B | 0.090 (4) | 0.105 (5) | 0.052 (3) | −0.044 (4) | 0.021 (3) | 0.003 (3) |
C8B | 0.084 (4) | 0.104 (4) | 0.055 (3) | −0.023 (3) | 0.030 (3) | −0.022 (3) |
C9B | 0.045 (3) | 0.085 (4) | 0.039 (3) | −0.001 (3) | 0.008 (2) | 0.004 (2) |
C10B | 0.043 (3) | 0.066 (3) | 0.038 (3) | −0.006 (2) | 0.007 (2) | 0.004 (2) |
C11B | 0.043 (3) | 0.079 (3) | 0.039 (3) | 0.009 (2) | 0.007 (2) | 0.012 (2) |
C12B | 0.049 (3) | 0.066 (3) | 0.043 (3) | 0.008 (2) | 0.015 (2) | 0.010 (2) |
C13B | 0.041 (3) | 0.041 (2) | 0.040 (2) | −0.010 (2) | 0.008 (2) | 0.000 (2) |
C14B | 0.037 (3) | 0.070 (3) | 0.046 (3) | 0.004 (2) | 0.001 (2) | 0.012 (2) |
C15B | 0.037 (3) | 0.084 (4) | 0.047 (3) | 0.011 (2) | 0.006 (2) | 0.012 (3) |
C16B | 0.049 (3) | 0.038 (2) | 0.036 (2) | −0.010 (2) | 0.008 (2) | −0.0006 (19) |
C17B | 0.054 (3) | 0.077 (4) | 0.045 (3) | −0.012 (3) | 0.009 (2) | −0.004 (2) |
C18B | 0.059 (3) | 0.096 (4) | 0.052 (3) | −0.017 (3) | 0.016 (3) | −0.009 (3) |
C19B | 0.086 (4) | 0.085 (4) | 0.044 (3) | −0.020 (3) | 0.017 (3) | 0.005 (3) |
C20B | 0.094 (4) | 0.081 (4) | 0.042 (3) | 0.006 (3) | 0.001 (3) | 0.009 (3) |
C21B | 0.063 (3) | 0.070 (3) | 0.046 (3) | 0.006 (3) | 0.006 (3) | 0.008 (2) |
Br1 | 0.0635 (3) | 0.0564 (3) | 0.0828 (4) | 0.0129 (3) | 0.0236 (3) | 0.0051 (3) |
Br2 | 0.0712 (4) | 0.0599 (3) | 0.0589 (3) | 0.0108 (3) | 0.0173 (3) | −0.0009 (2) |
OW | 0.065 (2) | 0.066 (2) | 0.071 (3) | −0.004 (2) | 0.006 (2) | 0.002 (2) |
Geometric parameters (Å, º) top
O1A—C9A | 1.212 (5) | N1B—C6B | 1.343 (5) |
N1A—C2A | 1.350 (5) | N1B—C2B | 1.345 (5) |
N1A—C6A | 1.358 (5) | N1B—C1B | 1.453 (5) |
N1A—C1A | 1.453 (5) | N2B—C4B | 1.327 (5) |
N2A—C4A | 1.336 (5) | N2B—C7B | 1.445 (6) |
N2A—C7A | 1.458 (5) | N2B—C8B | 1.455 (6) |
N2A—C8A | 1.459 (5) | C1B—C9B | 1.514 (6) |
C1A—C9A | 1.507 (6) | C1B—H1C | 0.9700 |
C1A—H1A | 0.9700 | C1B—H1D | 0.9700 |
C1A—H1B | 0.9700 | C2B—C3B | 1.345 (6) |
C2A—C3A | 1.347 (5) | C2B—H2B | 0.9300 |
C2A—H2A | 0.9300 | C3B—C4B | 1.405 (6) |
C3A—C4A | 1.428 (6) | C3B—H3B | 0.9300 |
C3A—H3A | 0.9300 | C4B—C5B | 1.399 (6) |
C4A—C5A | 1.403 (5) | C5B—C6B | 1.349 (5) |
C5A—C6A | 1.345 (5) | C5B—H5B | 0.9300 |
C5A—H5A | 0.9300 | C6B—H6B | 0.9300 |
C6A—H6A | 0.9300 | C7B—H7D | 0.9600 |
C7A—H7A | 0.9600 | C7B—H7E | 0.9600 |
C7A—H7B | 0.9600 | C7B—H7F | 0.9600 |
C7A—H7C | 0.9600 | C8B—H8D | 0.9600 |
C8A—H8A | 0.9600 | C8B—H8E | 0.9600 |
C8A—H8B | 0.9600 | C8B—H8F | 0.9600 |
C8A—H8C | 0.9600 | C9B—C10B | 1.477 (6) |
C9A—C10A | 1.481 (6) | C10B—C15B | 1.378 (6) |
C10A—C11A | 1.386 (5) | C10B—C11B | 1.384 (6) |
C10A—C15A | 1.392 (6) | C11B—C12B | 1.371 (5) |
C11A—C12A | 1.375 (5) | C11B—H11B | 0.9300 |
C11A—H11A | 0.9300 | C12B—C13B | 1.389 (6) |
C12A—C13A | 1.390 (5) | C12B—H12B | 0.9300 |
C12A—H12A | 0.9300 | C13B—C14B | 1.391 (5) |
C13A—C14A | 1.403 (6) | C13B—C16B | 1.484 (5) |
C13A—C16A | 1.493 (6) | C14B—C15B | 1.374 (6) |
C14A—C15A | 1.370 (6) | C14B—H14B | 0.9300 |
C14A—H14A | 0.9300 | C15B—H15B | 0.9300 |
C15A—H15A | 0.9300 | C16B—C21B | 1.391 (6) |
C16A—C21A | 1.380 (6) | C16B—C17B | 1.393 (6) |
C16A—C17A | 1.394 (6) | C17B—C18B | 1.381 (6) |
C17A—C18A | 1.380 (6) | C17B—H17B | 0.9300 |
C17A—H17A | 0.9300 | C18B—C19B | 1.367 (7) |
C18A—C19A | 1.362 (6) | C18B—H18B | 0.9300 |
C18A—H18A | 0.9300 | C19B—C20B | 1.371 (7) |
C19A—C20A | 1.376 (6) | C19B—H19B | 0.9300 |
C19A—H19A | 0.9300 | C20B—C21B | 1.362 (6) |
C20A—C21A | 1.388 (6) | C20B—H20B | 0.9300 |
C20A—H20A | 0.9300 | C21B—H21B | 0.9300 |
C21A—H21A | 0.9300 | OW—H22 | 0.86 |
O1B—C9B | 1.204 (5) | OW—H23 | 0.87 |
| | | |
C2A—N1A—C6A | 117.7 (4) | C6B—N1B—C1B | 120.6 (4) |
C2A—N1A—C1A | 121.6 (4) | C2B—N1B—C1B | 121.0 (4) |
C6A—N1A—C1A | 120.7 (4) | C4B—N2B—C7B | 122.2 (4) |
C4A—N2A—C7A | 122.4 (4) | C4B—N2B—C8B | 122.0 (4) |
C4A—N2A—C8A | 121.2 (4) | C7B—N2B—C8B | 115.7 (4) |
C7A—N2A—C8A | 116.4 (3) | N1B—C1B—C9B | 111.3 (3) |
N1A—C1A—C9A | 113.1 (3) | N1B—C1B—H1C | 109.4 |
N1A—C1A—H1A | 109.0 | C9B—C1B—H1C | 109.4 |
C9A—C1A—H1A | 109.0 | N1B—C1B—H1D | 109.4 |
N1A—C1A—H1B | 109.0 | C9B—C1B—H1D | 109.4 |
C9A—C1A—H1B | 109.0 | H1C—C1B—H1D | 108.0 |
H1A—C1A—H1B | 107.8 | C3B—C2B—N1B | 122.4 (4) |
C3A—C2A—N1A | 122.7 (4) | C3B—C2B—H2B | 118.8 |
C3A—C2A—H2A | 118.6 | N1B—C2B—H2B | 118.8 |
N1A—C2A—H2A | 118.6 | C2B—C3B—C4B | 120.7 (4) |
C2A—C3A—C4A | 120.8 (4) | C2B—C3B—H3B | 119.6 |
C2A—C3A—H3A | 119.6 | C4B—C3B—H3B | 119.6 |
C4A—C3A—H3A | 119.6 | N2B—C4B—C5B | 122.4 (4) |
N2A—C4A—C5A | 123.2 (4) | N2B—C4B—C3B | 122.1 (4) |
N2A—C4A—C3A | 122.3 (4) | C5B—C4B—C3B | 115.5 (4) |
C5A—C4A—C3A | 114.6 (4) | C6B—C5B—C4B | 121.0 (4) |
C6A—C5A—C4A | 121.7 (4) | C6B—C5B—H5B | 119.5 |
C6A—C5A—H5A | 119.1 | C4B—C5B—H5B | 119.5 |
C4A—C5A—H5A | 119.1 | N1B—C6B—C5B | 122.0 (4) |
C5A—C6A—N1A | 122.3 (4) | N1B—C6B—H6B | 119.0 |
C5A—C6A—H6A | 118.8 | C5B—C6B—H6B | 119.0 |
N1A—C6A—H6A | 118.8 | N2B—C7B—H7D | 109.5 |
N2A—C7A—H7A | 109.5 | N2B—C7B—H7E | 109.5 |
N2A—C7A—H7B | 109.5 | H7D—C7B—H7E | 109.5 |
H7A—C7A—H7B | 109.5 | N2B—C7B—H7F | 109.5 |
N2A—C7A—H7C | 109.5 | H7D—C7B—H7F | 109.5 |
H7A—C7A—H7C | 109.5 | H7E—C7B—H7F | 109.5 |
H7B—C7A—H7C | 109.5 | N2B—C8B—H8D | 109.5 |
N2A—C8A—H8A | 109.5 | N2B—C8B—H8E | 109.5 |
N2A—C8A—H8B | 109.5 | H8D—C8B—H8E | 109.5 |
H8A—C8A—H8B | 109.5 | N2B—C8B—H8F | 109.5 |
N2A—C8A—H8C | 109.5 | H8D—C8B—H8F | 109.5 |
H8A—C8A—H8C | 109.5 | H8E—C8B—H8F | 109.5 |
H8B—C8A—H8C | 109.5 | O1B—C9B—C10B | 122.6 (4) |
O1A—C9A—C10A | 121.9 (4) | O1B—C9B—C1B | 119.5 (4) |
O1A—C9A—C1A | 120.0 (4) | C10B—C9B—C1B | 117.9 (4) |
C10A—C9A—C1A | 118.1 (4) | C15B—C10B—C11B | 118.0 (4) |
C11A—C10A—C15A | 118.0 (4) | C15B—C10B—C9B | 119.1 (4) |
C11A—C10A—C9A | 122.7 (4) | C11B—C10B—C9B | 122.9 (4) |
C15A—C10A—C9A | 119.3 (4) | C12B—C11B—C10B | 120.9 (4) |
C12A—C11A—C10A | 121.0 (4) | C12B—C11B—H11B | 119.5 |
C12A—C11A—H11A | 119.5 | C10B—C11B—H11B | 119.5 |
C10A—C11A—H11A | 119.5 | C11B—C12B—C13B | 121.8 (4) |
C11A—C12A—C13A | 121.6 (4) | C11B—C12B—H12B | 119.1 |
C11A—C12A—H12A | 119.2 | C13B—C12B—H12B | 119.1 |
C13A—C12A—H12A | 119.2 | C12B—C13B—C14B | 116.4 (4) |
C12A—C13A—C14A | 117.1 (4) | C12B—C13B—C16B | 122.3 (4) |
C12A—C13A—C16A | 121.2 (4) | C14B—C13B—C16B | 121.2 (4) |
C14A—C13A—C16A | 121.7 (4) | C15B—C14B—C13B | 121.9 (4) |
C15A—C14A—C13A | 121.3 (4) | C15B—C14B—H14B | 119.0 |
C15A—C14A—H14A | 119.4 | C13B—C14B—H14B | 119.0 |
C13A—C14A—H14A | 119.4 | C14B—C15B—C10B | 120.8 (4) |
C14A—C15A—C10A | 121.1 (4) | C14B—C15B—H15B | 119.6 |
C14A—C15A—H15A | 119.5 | C10B—C15B—H15B | 119.6 |
C10A—C15A—H15A | 119.5 | C21B—C16B—C17B | 117.0 (4) |
C21A—C16A—C17A | 116.9 (4) | C21B—C16B—C13B | 121.9 (4) |
C21A—C16A—C13A | 121.5 (4) | C17B—C16B—C13B | 121.0 (4) |
C17A—C16A—C13A | 121.5 (4) | C18B—C17B—C16B | 120.9 (5) |
C18A—C17A—C16A | 121.9 (4) | C18B—C17B—H17B | 119.5 |
C18A—C17A—H17A | 119.1 | C16B—C17B—H17B | 119.5 |
C16A—C17A—H17A | 119.1 | C19B—C18B—C17B | 120.3 (5) |
C19A—C18A—C17A | 120.1 (4) | C19B—C18B—H18B | 119.8 |
C19A—C18A—H18A | 119.9 | C17B—C18B—H18B | 119.8 |
C17A—C18A—H18A | 119.9 | C18B—C19B—C20B | 119.5 (5) |
C18A—C19A—C20A | 119.5 (5) | C18B—C19B—H19B | 120.2 |
C18A—C19A—H19A | 120.2 | C20B—C19B—H19B | 120.2 |
C20A—C19A—H19A | 120.2 | C21B—C20B—C19B | 120.6 (5) |
C19A—C20A—C21A | 120.3 (5) | C21B—C20B—H20B | 119.7 |
C19A—C20A—H20A | 119.9 | C19B—C20B—H20B | 119.7 |
C21A—C20A—H20A | 119.9 | C20B—C21B—C16B | 121.6 (5) |
C16A—C21A—C20A | 121.3 (4) | C20B—C21B—H21B | 119.2 |
C16A—C21A—H21A | 119.3 | C16B—C21B—H21B | 119.2 |
C20A—C21A—H21A | 119.3 | H22—OW—H23 | 110 |
C6B—N1B—C2B | 118.3 (3) | | |
| | | |
C2A—N1A—C1A—C9A | 114.8 (4) | C6B—N1B—C1B—C9B | −90.6 (5) |
C6A—N1A—C1A—C9A | −65.8 (5) | C2B—N1B—C1B—C9B | 86.2 (5) |
C6A—N1A—C2A—C3A | 3.0 (6) | C6B—N1B—C2B—C3B | −1.7 (7) |
C1A—N1A—C2A—C3A | −177.5 (4) | C1B—N1B—C2B—C3B | −178.5 (4) |
N1A—C2A—C3A—C4A | 0.2 (7) | N1B—C2B—C3B—C4B | 0.6 (7) |
C7A—N2A—C4A—C5A | −177.4 (4) | C7B—N2B—C4B—C5B | −178.4 (4) |
C8A—N2A—C4A—C5A | 0.0 (6) | C8B—N2B—C4B—C5B | −1.1 (7) |
C7A—N2A—C4A—C3A | 1.9 (6) | C7B—N2B—C4B—C3B | 1.2 (7) |
C8A—N2A—C4A—C3A | 179.3 (4) | C8B—N2B—C4B—C3B | 178.4 (4) |
C2A—C3A—C4A—N2A | 177.5 (4) | C2B—C3B—C4B—N2B | −178.8 (4) |
C2A—C3A—C4A—C5A | −3.2 (6) | C2B—C3B—C4B—C5B | 0.8 (7) |
N2A—C4A—C5A—C6A | −177.6 (4) | N2B—C4B—C5B—C6B | 178.5 (4) |
C3A—C4A—C5A—C6A | 3.0 (6) | C3B—C4B—C5B—C6B | −1.1 (6) |
C4A—C5A—C6A—N1A | 0.1 (7) | C2B—N1B—C6B—C5B | 1.3 (6) |
C2A—N1A—C6A—C5A | −3.2 (6) | C1B—N1B—C6B—C5B | 178.2 (4) |
C1A—N1A—C6A—C5A | 177.4 (4) | C4B—C5B—C6B—N1B | 0.1 (7) |
N1A—C1A—C9A—O1A | 4.5 (6) | N1B—C1B—C9B—O1B | 2.2 (7) |
N1A—C1A—C9A—C10A | −177.3 (3) | N1B—C1B—C9B—C10B | −178.5 (4) |
O1A—C9A—C10A—C11A | −158.7 (4) | O1B—C9B—C10B—C15B | 5.6 (8) |
C1A—C9A—C10A—C11A | 23.1 (6) | C1B—C9B—C10B—C15B | −173.8 (4) |
O1A—C9A—C10A—C15A | 19.7 (7) | O1B—C9B—C10B—C11B | −175.0 (5) |
C1A—C9A—C10A—C15A | −158.5 (4) | C1B—C9B—C10B—C11B | 5.7 (7) |
C15A—C10A—C11A—C12A | 0.4 (6) | C15B—C10B—C11B—C12B | −0.6 (7) |
C9A—C10A—C11A—C12A | 178.7 (4) | C9B—C10B—C11B—C12B | 180.0 (4) |
C10A—C11A—C12A—C13A | 0.4 (7) | C10B—C11B—C12B—C13B | 0.0 (7) |
C11A—C12A—C13A—C14A | 0.2 (6) | C11B—C12B—C13B—C14B | 0.6 (6) |
C11A—C12A—C13A—C16A | −179.6 (4) | C11B—C12B—C13B—C16B | 179.6 (4) |
C12A—C13A—C14A—C15A | −1.6 (6) | C12B—C13B—C14B—C15B | −0.6 (7) |
C16A—C13A—C14A—C15A | 178.2 (4) | C16B—C13B—C14B—C15B | −179.6 (4) |
C13A—C14A—C15A—C10A | 2.4 (7) | C13B—C14B—C15B—C10B | 0.0 (7) |
C11A—C10A—C15A—C14A | −1.8 (6) | C11B—C10B—C15B—C14B | 0.5 (7) |
C9A—C10A—C15A—C14A | 179.8 (4) | C9B—C10B—C15B—C14B | −180.0 (4) |
C12A—C13A—C16A—C21A | 162.8 (4) | C12B—C13B—C16B—C21B | 178.6 (4) |
C14A—C13A—C16A—C21A | −16.9 (6) | C14B—C13B—C16B—C21B | −2.4 (6) |
C12A—C13A—C16A—C17A | −15.1 (6) | C12B—C13B—C16B—C17B | −0.8 (6) |
C14A—C13A—C16A—C17A | 165.1 (4) | C14B—C13B—C16B—C17B | 178.2 (4) |
C21A—C16A—C17A—C18A | −0.1 (6) | C21B—C16B—C17B—C18B | 0.3 (7) |
C13A—C16A—C17A—C18A | 178.0 (4) | C13B—C16B—C17B—C18B | 179.7 (4) |
C16A—C17A—C18A—C19A | 0.2 (7) | C16B—C17B—C18B—C19B | 0.7 (8) |
C17A—C18A—C19A—C20A | 0.3 (8) | C17B—C18B—C19B—C20B | −0.9 (8) |
C18A—C19A—C20A—C21A | −1.0 (8) | C18B—C19B—C20B—C21B | 0.2 (8) |
C17A—C16A—C21A—C20A | −0.6 (7) | C19B—C20B—C21B—C16B | 0.8 (8) |
C13A—C16A—C21A—C20A | −178.7 (4) | C17B—C16B—C21B—C20B | −1.0 (7) |
C19A—C20A—C21A—C16A | 1.1 (8) | C13B—C16B—C21B—C20B | 179.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1A—H1A···Br2 | 0.97 | 2.76 | 3.713 (5) | 170 |
C2A—H2A···Br2 | 0.93 | 2.98 | 3.839 (4) | 154 |
OW—H22···Br1 | 0.86 | 2.47 | 3.314 (4) | 170 |
OW—H23···Br2 | 0.87 | 2.45 | 3.311 (4) | 169 |
C1A—H1B···Br2i | 0.97 | 2.74 | 3.581 (5) | 146 |
C7A—H7B···O1Bii | 0.96 | 2.76 | 3.650 (6) | 155 |
C14A—H14A···OWiii | 0.93 | 2.61 | 3.530 (6) | 173 |
C21A—H21A···OWiii | 0.93 | 2.62 | 3.500 (6) | 157 |
C1B—H1D···Br1iv | 0.97 | 2.92 | 3.840 (5) | 158 |
C8B—H8D···Br2iv | 0.96 | 2.80 | 3.680 (5) | 153 |
C12B—H12B···Br1v | 0.93 | 2.99 | 3.874 (5) | 159 |
C14B—H14B···OWvi | 0.93 | 2.38 | 3.270 (6) | 160 |
C21B—H21B···OWvi | 0.93 | 2.85 | 3.774 (6) | 174 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) x, −y+1, z+1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) −x, y, −z+1/2. |