In the title compound, C
12H
20NO
+·Br
−·1.5H
2O, two crystallographically independent quaternary ammonium cations are associated by three very short C—H
π interactions with distances between the H atoms and the centroids of the benzene rings of 2.787 (8), 2.878 (7) and 2.932 (8) Å. A one-dimensional hydrogen-bonded spiral is formed along the
b axis by O—H
Br hydrogen bonds. Neighboring spirals are interrelated by translation and held together mainly by hydrogen bonds and O—H
O interactions. C—H
O and C—H
Br hydrogen bonds and C—H
π interactions play an important role in stabilizing the structure.
Supporting information
CCDC reference: 262450
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.008 Å
- R factor = 0.040
- wR factor = 0.102
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D H4B .. H5B .. 1.32 Ang.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit -P2yb
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C13 -C18 1.37 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12C .. BR2 .. 2.94 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.24
From the CIF: _reflns_number_total 4850
Count of symmetry unique reflns 2949
Completeness (_total/calc) 164.46%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1901
Fraction of Friedel pairs measured 0.645
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 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
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[(
R)-(+)-(1-hydroxy-3-phenylpropan-2-yl)trimethylammonium bromide]
sesquihydrate
top
Crystal data top
C12H20NO+·Br−·1.5H2O | F(000) = 628 |
Mr = 301.23 | Dx = 1.340 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yb | Cell parameters from 1820 reflections |
a = 13.2146 (17) Å | θ = 5.2–51.7° |
b = 6.9739 (9) Å | µ = 2.75 mm−1 |
c = 16.210 (2) Å | T = 273 K |
β = 91.490 (2)° | Rod, colorless |
V = 1493.3 (3) Å3 | 0.29 × 0.26 × 0.22 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 4850 independent reflections |
Radiation source: fine-focus sealed tube | 3769 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 25.2°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −15→15 |
Tmin = 0.471, Tmax = 0.547 | k = −8→8 |
7855 measured reflections | l = −19→17 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0496P)2 + 0.07P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
4850 reflections | Δρmax = 0.62 e Å−3 |
305 parameters | Δρmin = −0.38 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.018 (12) |
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 | Occ. (<1) |
Br1 | 0.82366 (4) | 0.80747 (9) | 0.92851 (3) | 0.06062 (17) | |
Br2 | 0.56224 (4) | 0.91538 (8) | 0.34885 (3) | 0.06341 (18) | |
O1 | 0.8258 (3) | 0.7724 (7) | 0.7301 (2) | 0.0771 (13) | |
H1 | 0.8554 | 0.7290 | 0.7711 | 0.116* | |
O2 | 0.6504 (4) | 1.1669 (7) | 0.1995 (3) | 0.0929 (15) | |
H2 | 0.6404 | 1.1122 | 0.2434 | 0.139* | |
O3 | 0.5137 (4) | 0.5799 (6) | 0.0793 (3) | 0.0878 (14) | |
O4 | 0.4190 (3) | 0.2163 (6) | 0.0709 (2) | 0.0705 (11) | |
O5 | 0.4346 (3) | 0.8808 (7) | 0.1687 (2) | 0.0770 (12) | |
N1 | 0.6288 (3) | 0.9154 (7) | 0.6494 (2) | 0.0476 (9) | |
N2 | 0.7995 (3) | 1.3042 (7) | 0.0732 (2) | 0.0447 (9) | |
C1 | 0.7916 (4) | 0.5635 (7) | 0.5272 (3) | 0.0444 (12) | |
C2 | 0.8813 (4) | 0.4766 (8) | 0.5509 (3) | 0.0541 (14) | |
H2A | 0.9227 | 0.5353 | 0.5906 | 0.065* | |
C3 | 0.9107 (4) | 0.3086 (12) | 0.5180 (3) | 0.0690 (16) | |
H3 | 0.9725 | 0.2558 | 0.5347 | 0.083* | |
C4 | 0.8521 (5) | 0.2150 (10) | 0.4610 (4) | 0.0710 (17) | |
H4 | 0.8729 | 0.0990 | 0.4388 | 0.085* | |
C5 | 0.7607 (5) | 0.2964 (11) | 0.4368 (3) | 0.0694 (16) | |
H5 | 0.7189 | 0.2340 | 0.3983 | 0.083* | |
C6 | 0.7312 (4) | 0.4691 (8) | 0.4692 (3) | 0.0566 (15) | |
H6 | 0.6699 | 0.5231 | 0.4519 | 0.068* | |
C7 | 0.7594 (4) | 0.7533 (7) | 0.5604 (3) | 0.0482 (13) | |
H7A | 0.7256 | 0.8261 | 0.5168 | 0.058* | |
H7B | 0.8188 | 0.8248 | 0.5788 | 0.058* | |
C8 | 0.6879 (4) | 0.7294 (7) | 0.6326 (3) | 0.0450 (12) | |
H8 | 0.6379 | 0.6320 | 0.6160 | 0.054* | |
C9 | 0.7449 (4) | 0.6521 (8) | 0.7078 (3) | 0.0526 (13) | |
H9A | 0.6992 | 0.6420 | 0.7535 | 0.063* | |
H9B | 0.7703 | 0.5248 | 0.6960 | 0.063* | |
C10 | 0.6931 (5) | 1.0915 (8) | 0.6521 (4) | 0.0678 (17) | |
H10A | 0.7427 | 1.0805 | 0.6962 | 0.102* | |
H10B | 0.6514 | 1.2017 | 0.6612 | 0.102* | |
H10C | 0.7267 | 1.1054 | 0.6007 | 0.102* | |
C11 | 0.5725 (5) | 0.9017 (11) | 0.7272 (3) | 0.0750 (17) | |
H11A | 0.6192 | 0.8771 | 0.7723 | 0.113* | |
H11B | 0.5243 | 0.7990 | 0.7229 | 0.113* | |
H11C | 0.5377 | 1.0202 | 0.7366 | 0.113* | |
C12 | 0.5498 (4) | 0.9357 (12) | 0.5813 (3) | 0.0793 (19) | |
H12A | 0.5090 | 1.0468 | 0.5913 | 0.119* | |
H12B | 0.5076 | 0.8237 | 0.5798 | 0.119* | |
H12C | 0.5824 | 0.9497 | 0.5294 | 0.119* | |
C13 | 0.9162 (4) | 0.9488 (8) | 0.2298 (3) | 0.0496 (13) | |
C14 | 0.8690 (4) | 0.8412 (9) | 0.2894 (3) | 0.0550 (15) | |
H14 | 0.8098 | 0.8862 | 0.3125 | 0.066* | |
C15 | 0.9095 (5) | 0.6661 (9) | 0.3149 (3) | 0.0616 (15) | |
H15 | 0.8773 | 0.5945 | 0.3549 | 0.074* | |
C16 | 0.9942 (5) | 0.6009 (9) | 0.2823 (4) | 0.0679 (17) | |
H16 | 1.0208 | 0.4834 | 0.2992 | 0.082* | |
C17 | 1.0423 (4) | 0.7069 (10) | 0.2236 (4) | 0.0728 (19) | |
H17 | 1.1020 | 0.6617 | 0.2015 | 0.087* | |
C18 | 1.0028 (4) | 0.8788 (9) | 0.1975 (3) | 0.0622 (16) | |
H18 | 1.0355 | 0.9484 | 0.1572 | 0.075* | |
C19 | 0.8748 (4) | 1.1425 (8) | 0.2021 (3) | 0.0561 (15) | |
H19A | 0.9304 | 1.2276 | 0.1896 | 0.067* | |
H19B | 0.8368 | 1.1997 | 0.2462 | 0.067* | |
C20 | 0.8045 (4) | 1.1173 (7) | 0.1238 (3) | 0.0447 (12) | |
H20 | 0.8353 | 1.0192 | 0.0892 | 0.054* | |
C21 | 0.7011 (4) | 1.0440 (9) | 0.1472 (3) | 0.0640 (16) | |
H21A | 0.6602 | 1.0254 | 0.0973 | 0.077* | |
H21B | 0.7091 | 0.9203 | 0.1739 | 0.077* | |
C22 | 0.8983 (4) | 1.3300 (11) | 0.0318 (4) | 0.0766 (18) | |
H22A | 0.8958 | 1.4440 | −0.0013 | 0.115* | |
H22B | 0.9109 | 1.2211 | −0.0027 | 0.115* | |
H22C | 0.9517 | 1.3414 | 0.0729 | 0.115* | |
C23 | 0.7195 (4) | 1.2888 (10) | 0.0058 (3) | 0.0614 (14) | |
H23A | 0.6538 | 1.2857 | 0.0298 | 0.092* | |
H23B | 0.7297 | 1.1733 | −0.0251 | 0.092* | |
H23C | 0.7238 | 1.3976 | −0.0302 | 0.092* | |
C24 | 0.7776 (4) | 1.4800 (8) | 0.1235 (3) | 0.0613 (15) | |
H24A | 0.7595 | 1.5841 | 0.0872 | 0.074* | |
H24B | 0.8367 | 1.5142 | 0.1559 | 0.074* | |
H24C | 0.7226 | 1.4540 | 0.1593 | 0.074* | |
H3A | 0.4882 | 0.4558 | 0.0784 | 0.074* | |
H3B | 0.4894 | 0.6804 | 0.1029 | 0.074* | |
H4'A | 0.4460 | 0.3619 | 0.0648 | 0.074* | 0.50 |
H4"A | 0.3319 | 0.2289 | 0.0837 | 0.074* | 0.50 |
H4B | 0.4575 | 0.1048 | 0.0801 | 0.074* | |
H5A | 0.4205 | 0.8563 | 0.2266 | 0.074* | |
H5B | 0.4389 | 1.0021 | 0.1461 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0678 (3) | 0.0611 (3) | 0.0530 (3) | −0.0050 (3) | 0.0015 (2) | −0.0033 (3) |
Br2 | 0.0762 (4) | 0.0640 (3) | 0.0498 (3) | −0.0071 (3) | −0.0027 (2) | 0.0062 (3) |
O1 | 0.073 (2) | 0.102 (4) | 0.055 (2) | −0.026 (3) | −0.0203 (19) | 0.014 (2) |
O2 | 0.093 (3) | 0.084 (3) | 0.105 (4) | 0.021 (3) | 0.047 (3) | 0.019 (3) |
O3 | 0.112 (4) | 0.055 (3) | 0.098 (3) | −0.002 (2) | 0.020 (3) | −0.002 (3) |
O4 | 0.073 (3) | 0.066 (2) | 0.073 (3) | 0.007 (2) | 0.001 (2) | −0.002 (2) |
O5 | 0.100 (3) | 0.071 (3) | 0.060 (2) | 0.002 (2) | −0.007 (2) | −0.003 (2) |
N1 | 0.053 (2) | 0.049 (2) | 0.041 (2) | 0.001 (2) | 0.0068 (17) | −0.004 (2) |
N2 | 0.044 (2) | 0.049 (2) | 0.041 (2) | 0.010 (2) | −0.0029 (16) | 0.003 (2) |
C1 | 0.046 (3) | 0.054 (3) | 0.033 (2) | −0.011 (2) | 0.006 (2) | −0.002 (2) |
C2 | 0.058 (3) | 0.064 (4) | 0.039 (3) | 0.003 (3) | −0.007 (2) | −0.010 (3) |
C3 | 0.065 (3) | 0.086 (4) | 0.056 (3) | 0.019 (4) | 0.002 (3) | 0.002 (4) |
C4 | 0.092 (5) | 0.068 (4) | 0.054 (4) | −0.009 (4) | 0.017 (3) | −0.012 (3) |
C5 | 0.074 (4) | 0.082 (4) | 0.052 (3) | −0.018 (4) | 0.001 (3) | −0.026 (4) |
C6 | 0.052 (3) | 0.071 (4) | 0.047 (3) | −0.004 (3) | −0.002 (2) | −0.007 (3) |
C7 | 0.057 (3) | 0.049 (3) | 0.038 (3) | −0.004 (2) | 0.004 (2) | 0.007 (2) |
C8 | 0.049 (3) | 0.043 (3) | 0.043 (3) | −0.005 (2) | 0.004 (2) | −0.002 (2) |
C9 | 0.059 (3) | 0.057 (3) | 0.041 (3) | −0.010 (3) | 0.001 (2) | 0.007 (2) |
C10 | 0.079 (4) | 0.054 (4) | 0.070 (4) | −0.012 (3) | 0.018 (3) | −0.007 (3) |
C11 | 0.090 (4) | 0.070 (4) | 0.067 (3) | −0.006 (4) | 0.038 (3) | −0.012 (4) |
C12 | 0.071 (4) | 0.093 (5) | 0.073 (4) | 0.032 (4) | −0.017 (3) | −0.012 (4) |
C13 | 0.053 (3) | 0.053 (4) | 0.043 (3) | 0.008 (3) | −0.013 (2) | −0.009 (3) |
C14 | 0.058 (3) | 0.072 (5) | 0.036 (3) | 0.008 (3) | −0.001 (2) | 0.001 (3) |
C15 | 0.071 (4) | 0.067 (4) | 0.046 (3) | 0.002 (3) | −0.007 (3) | 0.008 (3) |
C16 | 0.087 (5) | 0.059 (4) | 0.057 (4) | 0.009 (3) | −0.024 (3) | 0.006 (3) |
C17 | 0.058 (4) | 0.080 (5) | 0.080 (4) | 0.028 (4) | −0.011 (3) | −0.012 (4) |
C18 | 0.061 (4) | 0.079 (5) | 0.046 (3) | −0.006 (3) | 0.001 (3) | 0.006 (3) |
C19 | 0.065 (3) | 0.055 (4) | 0.047 (3) | −0.002 (3) | −0.015 (3) | −0.007 (3) |
C20 | 0.052 (3) | 0.038 (3) | 0.045 (3) | 0.003 (2) | −0.005 (2) | −0.001 (2) |
C21 | 0.066 (4) | 0.064 (4) | 0.062 (4) | −0.010 (3) | −0.008 (3) | 0.008 (3) |
C22 | 0.063 (3) | 0.088 (5) | 0.080 (4) | 0.014 (4) | 0.020 (3) | 0.026 (4) |
C23 | 0.073 (3) | 0.056 (3) | 0.055 (3) | 0.006 (3) | −0.020 (3) | 0.003 (3) |
C24 | 0.076 (4) | 0.050 (3) | 0.058 (3) | 0.001 (3) | −0.008 (3) | 0.000 (3) |
Geometric parameters (Å, º) top
O1—C9 | 1.399 (6) | C10—H10A | 0.9600 |
O1—H1 | 0.8200 | C10—H10B | 0.9600 |
O2—C21 | 1.391 (7) | C10—H10C | 0.9600 |
O2—H2 | 0.8200 | C11—H11A | 0.9600 |
O3—H3A | 0.9286 | C11—H11B | 0.9600 |
O3—H3B | 0.8644 | C11—H11C | 0.9600 |
O4—H4'A | 1.0818 | C12—H12A | 0.9600 |
O4—H4"A | 1.1779 | C12—H12B | 0.9600 |
O4—H4B | 0.9379 | C12—H12C | 0.9600 |
O5—H5A | 0.9765 | C13—C18 | 1.361 (7) |
O5—H5B | 0.9240 | C13—C14 | 1.384 (7) |
N1—C11 | 1.483 (6) | C13—C19 | 1.521 (7) |
N1—C10 | 1.494 (7) | C14—C15 | 1.392 (8) |
N1—C12 | 1.507 (6) | C14—H14 | 0.9300 |
N1—C8 | 1.542 (7) | C15—C16 | 1.330 (8) |
N2—C22 | 1.494 (6) | C15—H15 | 0.9300 |
N2—C24 | 1.505 (7) | C16—C17 | 1.373 (9) |
N2—C23 | 1.505 (6) | C16—H16 | 0.9300 |
N2—C20 | 1.541 (7) | C17—C18 | 1.370 (9) |
C1—C2 | 1.376 (7) | C17—H17 | 0.9300 |
C1—C6 | 1.385 (6) | C18—H18 | 0.9300 |
C1—C7 | 1.495 (7) | C19—C20 | 1.562 (7) |
C2—C3 | 1.348 (9) | C19—H19A | 0.9700 |
C2—H2A | 0.9300 | C19—H19B | 0.9700 |
C3—C4 | 1.358 (8) | C20—C21 | 1.516 (7) |
C3—H3 | 0.9300 | C20—H20 | 0.9800 |
C4—C5 | 1.382 (8) | C21—H21A | 0.9700 |
C4—H4 | 0.9300 | C21—H21B | 0.9700 |
C5—C6 | 1.374 (9) | C22—H22A | 0.9600 |
C5—H5 | 0.9300 | C22—H22B | 0.9600 |
C6—H6 | 0.9300 | C22—H22C | 0.9600 |
C7—C8 | 1.532 (7) | C23—H23A | 0.9600 |
C7—H7A | 0.9700 | C23—H23B | 0.9600 |
C7—H7B | 0.9700 | C23—H23C | 0.9600 |
C8—C9 | 1.516 (7) | C24—H24A | 0.9600 |
C8—H8 | 0.9800 | C24—H24B | 0.9600 |
C9—H9A | 0.9700 | C24—H24C | 0.9600 |
C9—H9B | 0.9700 | | |
| | | |
C9—O1—H1 | 109.5 | N1—C11—H11C | 109.5 |
C21—O2—H2 | 109.5 | H11A—C11—H11C | 109.5 |
H3A—O3—H3B | 128.7 | H11B—C11—H11C | 109.5 |
H4'A—O4—H4"A | 105.8 | N1—C12—H12A | 109.5 |
H4'A—O4—H4B | 127.9 | N1—C12—H12B | 109.5 |
H4"A—O4—H4B | 124.2 | H12A—C12—H12B | 109.5 |
H5A—O5—H5B | 123.9 | N1—C12—H12C | 109.5 |
C11—N1—C10 | 109.0 (4) | H12A—C12—H12C | 109.5 |
C11—N1—C12 | 106.0 (4) | H12B—C12—H12C | 109.5 |
C10—N1—C12 | 109.1 (5) | C18—C13—C14 | 118.2 (5) |
C11—N1—C8 | 111.3 (5) | C18—C13—C19 | 120.3 (5) |
C10—N1—C8 | 114.0 (3) | C14—C13—C19 | 121.5 (5) |
C12—N1—C8 | 107.1 (4) | C13—C14—C15 | 120.4 (5) |
C22—N2—C24 | 109.1 (5) | C13—C14—H14 | 119.8 |
C22—N2—C23 | 106.8 (4) | C15—C14—H14 | 119.8 |
C24—N2—C23 | 108.0 (4) | C16—C15—C14 | 120.2 (6) |
C22—N2—C20 | 108.4 (4) | C16—C15—H15 | 119.9 |
C24—N2—C20 | 114.0 (3) | C14—C15—H15 | 119.9 |
C23—N2—C20 | 110.2 (4) | C15—C16—C17 | 120.1 (6) |
C2—C1—C6 | 117.2 (5) | C15—C16—H16 | 120.0 |
C2—C1—C7 | 122.7 (4) | C17—C16—H16 | 120.0 |
C6—C1—C7 | 120.1 (5) | C18—C17—C16 | 120.3 (6) |
C3—C2—C1 | 121.8 (5) | C18—C17—H17 | 119.8 |
C3—C2—H2A | 119.1 | C16—C17—H17 | 119.8 |
C1—C2—H2A | 119.1 | C13—C18—C17 | 120.8 (6) |
C2—C3—C4 | 121.4 (6) | C13—C18—H18 | 119.6 |
C2—C3—H3 | 119.3 | C17—C18—H18 | 119.6 |
C4—C3—H3 | 119.3 | C13—C19—C20 | 110.0 (4) |
C3—C4—C5 | 118.3 (6) | C13—C19—H19A | 109.7 |
C3—C4—H4 | 120.8 | C20—C19—H19A | 109.7 |
C5—C4—H4 | 120.8 | C13—C19—H19B | 109.7 |
C6—C5—C4 | 120.4 (5) | C20—C19—H19B | 109.7 |
C6—C5—H5 | 119.8 | H19A—C19—H19B | 108.2 |
C4—C5—H5 | 119.8 | C21—C20—N2 | 113.1 (4) |
C5—C6—C1 | 120.8 (5) | C21—C20—C19 | 110.8 (4) |
C5—C6—H6 | 119.6 | N2—C20—C19 | 110.7 (4) |
C1—C6—H6 | 119.6 | C21—C20—H20 | 107.3 |
C1—C7—C8 | 111.5 (4) | N2—C20—H20 | 107.3 |
C1—C7—H7A | 109.3 | C19—C20—H20 | 107.3 |
C8—C7—H7A | 109.3 | O2—C21—C20 | 113.4 (5) |
C1—C7—H7B | 109.3 | O2—C21—H21A | 108.9 |
C8—C7—H7B | 109.3 | C20—C21—H21A | 108.9 |
H7A—C7—H7B | 108.0 | O2—C21—H21B | 108.9 |
C9—C8—C7 | 110.5 (4) | C20—C21—H21B | 108.9 |
C9—C8—N1 | 113.6 (4) | H21A—C21—H21B | 107.7 |
C7—C8—N1 | 111.7 (4) | N2—C22—H22A | 109.5 |
C9—C8—H8 | 106.9 | N2—C22—H22B | 109.5 |
C7—C8—H8 | 106.9 | H22A—C22—H22B | 109.5 |
N1—C8—H8 | 106.9 | N2—C22—H22C | 109.5 |
O1—C9—C8 | 110.8 (4) | H22A—C22—H22C | 109.5 |
O1—C9—H9A | 109.5 | H22B—C22—H22C | 109.5 |
C8—C9—H9A | 109.5 | N2—C23—H23A | 109.5 |
O1—C9—H9B | 109.5 | N2—C23—H23B | 109.5 |
C8—C9—H9B | 109.5 | H23A—C23—H23B | 109.5 |
H9A—C9—H9B | 108.1 | N2—C23—H23C | 109.5 |
N1—C10—H10A | 109.5 | H23A—C23—H23C | 109.5 |
N1—C10—H10B | 109.5 | H23B—C23—H23C | 109.5 |
H10A—C10—H10B | 109.5 | N2—C24—H24A | 109.5 |
N1—C10—H10C | 109.5 | N2—C24—H24B | 109.5 |
H10A—C10—H10C | 109.5 | H24A—C24—H24B | 109.5 |
H10B—C10—H10C | 109.5 | N2—C24—H24C | 109.5 |
N1—C11—H11A | 109.5 | H24A—C24—H24C | 109.5 |
N1—C11—H11B | 109.5 | H24B—C24—H24C | 109.5 |
H11A—C11—H11B | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Br1 | 0.82 | 2.65 | 3.226 (4) | 128 |
O2—H2···Br2 | 0.82 | 2.44 | 3.231 (5) | 162 |
O3—H3A···O4 | 0.93 | 1.91 | 2.829 (6) | 172 |
O3—H3B···O5 | 0.86 | 1.91 | 2.770 (7) | 172 |
O4—H4B···O5i | 0.94 | 2.15 | 2.830 (6) | 129 |
O4—H4"A···Br1ii | 1.18 | 2.13 | 3.270 (4) | 161 |
O5—H5A···Br2 | 0.98 | 2.72 | 3.343 (4) | 122 |
O5—H5B···O4iii | 0.92 | 1.94 | 2.830 (6) | 161 |
C7—H7B···O1 | 0.97 | 2.48 | 2.868 (6) | 104 |
C10—H10A···O1 | 0.96 | 2.47 | 3.083 (8) | 122 |
C12—H12C···Br2 | 0.96 | 2.94 | 3.779 (6) | 146 |
C12—H12A···Br2iv | 0.96 | 2.91 | 3.840 (7) | 163 |
C16—H16···O1v | 0.93 | 2.56 | 3.313 (8) | 138 |
C19—H19B···O2 | 0.97 | 2.57 | 2.970 (7) | 105 |
C22—H22A···Br1vi | 0.96 | 2.93 | 3.844 (7) | 160 |
C24—H24C···O2 | 0.96 | 2.32 | 3.037 (8) | 131 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1; (v) −x+2, y−1/2, −z+1; (vi) x, y+1, z−1. |