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The title compound, C
14H
10NO
2F
3, adopts the enol-imine tautomeric form. There are two independent molecules in the asymmetric unit, with the two aromatic rings inclined at 38.97 (9) and 37.68 (9)°. Each of the independent molecules forms O—H
O hydrogen-bonded centrosymmetric
R22(10) dimers.
Supporting information
CCDC reference: 633658
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.060
- wR factor = 0.169
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
| Author Response:
The crystal was twinned and the reflection data were measured for the two
twin domains, scaled and combined together, but overlapping reflections
could not be satisfactorily measured and were discarded, leading to a data
completeness of only slightly over 91%.
|
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 27.90
From the CIF: _diffrn_reflns_theta_full 27.90
From the CIF: _reflns_number_total 5534
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 6062
Completeness (_total/calc) 91.29%
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.112
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 600 Deg.
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14A
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14B
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
1 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: SHELXS97 (Sheldrick, 1997); 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).
(
E)-3-[2-(Trifluoromethyl)phenyliminomethyl]benzene-1,2-diol
top
Crystal data top
C14H10F3NO2 | Z = 4 |
Mr = 281.23 | F(000) = 576 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
Hall symbol: -P 1 | Melting point = 648–649 K |
a = 7.5806 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5128 (7) Å | Cell parameters from 20837 reflections |
c = 16.2370 (11) Å | θ = 2.2–27.7° |
α = 83.162 (6)° | µ = 0.13 mm−1 |
β = 89.612 (6)° | T = 296 K |
γ = 81.938 (6)° | Prismatic needle, red |
V = 1272.01 (15) Å3 | 0.62 × 0.41 × 0.12 mm |
Data collection top
Stoe IPDS-2 diffractometer | 5534 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2951 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.112 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.9°, θmin = 2.7° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −13→13 |
Tmin = 0.930, Tmax = 0.985 | l = −21→21 |
24664 measured reflections | |
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)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.169 | w = 1/[σ2(Fo2) + (0.0768P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5534 reflections | Δρmax = 0.20 e Å−3 |
378 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.006 (2) |
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 | |
C1A | 0.2290 (3) | 1.1743 (3) | 0.66421 (16) | 0.0511 (6) | |
C1B | 0.8005 (3) | −0.1689 (3) | 0.83156 (16) | 0.0504 (6) | |
C2A | 0.2942 (3) | 1.1334 (3) | 0.58920 (16) | 0.0494 (6) | |
C2B | 0.8513 (3) | −0.1321 (2) | 0.90732 (16) | 0.0486 (6) | |
C3A | 0.2807 (3) | 1.2198 (3) | 0.51696 (17) | 0.0560 (6) | |
C3B | 0.8743 (3) | −0.2212 (3) | 0.97762 (16) | 0.0542 (6) | |
C4A | 0.2055 (4) | 1.3462 (3) | 0.5194 (2) | 0.0670 (8) | |
H4A | 0.1966 | 1.4039 | 0.4710 | 0.080* | |
C4B | 0.8517 (4) | −0.3479 (3) | 0.9727 (2) | 0.0663 (7) | |
H4B | 0.8682 | −0.4080 | 1.0199 | 0.080* | |
C5A | 0.1429 (4) | 1.3886 (3) | 0.5935 (2) | 0.0719 (8) | |
H5A | 0.0931 | 1.4744 | 0.5946 | 0.086* | |
C5B | 0.8043 (4) | −0.3865 (3) | 0.8979 (2) | 0.0720 (8) | |
H5B | 0.7901 | −0.4724 | 0.8952 | 0.086* | |
C6A | 0.1543 (4) | 1.3039 (3) | 0.6650 (2) | 0.0651 (8) | |
H6A | 0.1122 | 1.3328 | 0.7144 | 0.078* | |
C6B | 0.7787 (4) | −0.2994 (3) | 0.8287 (2) | 0.0639 (7) | |
H6B | 0.7465 | −0.3260 | 0.7791 | 0.077* | |
C7A | 0.2363 (3) | 1.0841 (3) | 0.73871 (16) | 0.0520 (6) | |
H7A | 0.1930 | 1.1131 | 0.7879 | 0.062* | |
C7B | 0.7676 (3) | −0.0757 (3) | 0.75861 (15) | 0.0511 (6) | |
H7B | 0.7330 | −0.1028 | 0.7095 | 0.061* | |
C8A | 0.3093 (3) | 0.8767 (3) | 0.81217 (15) | 0.0521 (6) | |
C8B | 0.7534 (3) | 0.1337 (3) | 0.68776 (15) | 0.0525 (6) | |
C9A | 0.3555 (4) | 0.9120 (3) | 0.88862 (17) | 0.0643 (7) | |
H9A | 0.3761 | 0.9961 | 0.8928 | 0.077* | |
C9B | 0.8054 (4) | 0.1006 (3) | 0.61010 (17) | 0.0642 (7) | |
H9B | 0.8619 | 0.0178 | 0.6045 | 0.077* | |
C10A | 0.3703 (4) | 0.8208 (4) | 0.95830 (18) | 0.0772 (9) | |
H10A | 0.4009 | 0.8445 | 1.0092 | 0.093* | |
C10B | 0.7724 (5) | 0.1922 (4) | 0.54060 (18) | 0.0752 (9) | |
H10B | 0.8077 | 0.1701 | 0.4886 | 0.090* | |
C11A | 0.3405 (4) | 0.6969 (4) | 0.9531 (2) | 0.0826 (10) | |
H11A | 0.3500 | 0.6370 | 1.0005 | 0.099* | |
C11B | 0.6885 (5) | 0.3146 (4) | 0.5479 (2) | 0.0793 (10) | |
H11B | 0.6638 | 0.3740 | 0.5009 | 0.095* | |
C12A | 0.2962 (4) | 0.6600 (3) | 0.87792 (19) | 0.0699 (8) | |
H12A | 0.2761 | 0.5755 | 0.8747 | 0.084* | |
C12B | 0.6409 (4) | 0.3496 (3) | 0.62479 (19) | 0.0677 (8) | |
H12B | 0.5862 | 0.4332 | 0.6297 | 0.081* | |
C13A | 0.2818 (3) | 0.7488 (3) | 0.80738 (16) | 0.0545 (6) | |
C13B | 0.6745 (3) | 0.2600 (3) | 0.69532 (16) | 0.0543 (6) | |
C14A | 0.2397 (4) | 0.7063 (3) | 0.72647 (18) | 0.0629 (7) | |
C14B | 0.6272 (4) | 0.3002 (3) | 0.77857 (18) | 0.0633 (7) | |
F1A | 0.1044 (2) | 0.78176 (19) | 0.68457 (11) | 0.0776 (5) | |
F1B | 0.5118 (3) | 0.2316 (2) | 0.81938 (12) | 0.0882 (6) | |
F2A | 0.3785 (3) | 0.7057 (2) | 0.67434 (11) | 0.0881 (6) | |
F2B | 0.7692 (2) | 0.2876 (2) | 0.82889 (11) | 0.0833 (6) | |
F3A | 0.1964 (3) | 0.5869 (2) | 0.73428 (13) | 0.0994 (7) | |
F3B | 0.5557 (3) | 0.4243 (2) | 0.77483 (14) | 0.1074 (8) | |
N1A | 0.3013 (3) | 0.9643 (2) | 0.73865 (13) | 0.0522 (5) | |
N1B | 0.7851 (3) | 0.0440 (2) | 0.76004 (12) | 0.0516 (5) | |
O1A | 0.3689 (3) | 1.0095 (2) | 0.58357 (12) | 0.0605 (5) | |
H1A | 0.360 (5) | 0.962 (4) | 0.635 (3) | 0.107 (13)* | |
O1B | 0.8754 (3) | −0.00821 (19) | 0.91480 (12) | 0.0593 (5) | |
H1B | 0.846 (4) | 0.042 (4) | 0.867 (2) | 0.088 (11)* | |
O2A | 0.3399 (3) | 1.1810 (3) | 0.44327 (13) | 0.0731 (6) | |
H2A | 0.406 (7) | 1.112 (5) | 0.451 (3) | 0.125 (18)* | |
O2B | 0.9179 (3) | −0.1857 (3) | 1.05239 (12) | 0.0709 (6) | |
H2B | 0.962 (5) | −0.117 (4) | 1.045 (3) | 0.104 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0465 (13) | 0.0504 (16) | 0.0591 (15) | −0.0104 (10) | −0.0030 (10) | −0.0131 (12) |
C1B | 0.0438 (12) | 0.0533 (17) | 0.0549 (14) | −0.0056 (10) | −0.0031 (10) | −0.0113 (12) |
C2A | 0.0467 (12) | 0.0467 (16) | 0.0561 (15) | −0.0090 (10) | −0.0018 (10) | −0.0081 (12) |
C2B | 0.0455 (12) | 0.0434 (15) | 0.0558 (14) | −0.0012 (10) | −0.0036 (10) | −0.0065 (12) |
C3A | 0.0522 (14) | 0.0571 (18) | 0.0581 (16) | −0.0100 (11) | −0.0053 (11) | −0.0019 (13) |
C3B | 0.0518 (13) | 0.0540 (17) | 0.0559 (15) | −0.0072 (11) | −0.0046 (11) | −0.0032 (13) |
C4A | 0.0625 (16) | 0.0563 (19) | 0.078 (2) | −0.0092 (13) | −0.0151 (14) | 0.0089 (15) |
C4B | 0.0633 (16) | 0.0570 (19) | 0.0749 (19) | −0.0103 (13) | −0.0050 (13) | 0.0092 (15) |
C5A | 0.0674 (17) | 0.0494 (18) | 0.096 (2) | 0.0014 (13) | −0.0125 (15) | −0.0070 (17) |
C5B | 0.083 (2) | 0.0467 (18) | 0.088 (2) | −0.0170 (14) | −0.0063 (16) | −0.0037 (16) |
C6A | 0.0581 (15) | 0.060 (2) | 0.079 (2) | −0.0042 (12) | −0.0016 (13) | −0.0213 (16) |
C6B | 0.0651 (16) | 0.0579 (19) | 0.0730 (19) | −0.0152 (13) | −0.0031 (13) | −0.0173 (15) |
C7A | 0.0515 (13) | 0.0584 (19) | 0.0483 (14) | −0.0097 (11) | 0.0044 (10) | −0.0140 (12) |
C7B | 0.0461 (13) | 0.0591 (18) | 0.0494 (14) | −0.0056 (11) | −0.0063 (10) | −0.0137 (12) |
C8A | 0.0476 (13) | 0.0623 (18) | 0.0455 (13) | −0.0046 (11) | 0.0065 (10) | −0.0070 (12) |
C8B | 0.0507 (13) | 0.0603 (18) | 0.0485 (14) | −0.0161 (11) | −0.0089 (10) | −0.0044 (12) |
C9A | 0.0662 (16) | 0.077 (2) | 0.0520 (16) | −0.0116 (14) | 0.0052 (12) | −0.0157 (15) |
C9B | 0.0687 (16) | 0.077 (2) | 0.0516 (16) | −0.0212 (14) | −0.0018 (12) | −0.0133 (15) |
C10A | 0.077 (2) | 0.108 (3) | 0.0439 (16) | −0.0049 (18) | 0.0050 (13) | −0.0066 (17) |
C10B | 0.089 (2) | 0.100 (3) | 0.0456 (16) | −0.0424 (19) | −0.0037 (13) | −0.0083 (17) |
C11A | 0.084 (2) | 0.101 (3) | 0.0540 (18) | −0.0032 (19) | 0.0109 (14) | 0.0131 (18) |
C11B | 0.088 (2) | 0.093 (3) | 0.0584 (19) | −0.0373 (19) | −0.0174 (15) | 0.0133 (17) |
C12A | 0.0732 (18) | 0.068 (2) | 0.0645 (18) | −0.0051 (14) | 0.0140 (14) | 0.0022 (16) |
C12B | 0.0685 (17) | 0.063 (2) | 0.0705 (19) | −0.0170 (13) | −0.0202 (14) | 0.0066 (15) |
C13A | 0.0539 (14) | 0.0557 (18) | 0.0520 (14) | −0.0033 (11) | 0.0088 (10) | −0.0038 (12) |
C13B | 0.0530 (13) | 0.0582 (18) | 0.0526 (14) | −0.0154 (11) | −0.0123 (10) | −0.0014 (12) |
C14A | 0.0721 (17) | 0.0557 (19) | 0.0610 (17) | −0.0099 (13) | 0.0090 (13) | −0.0071 (14) |
C14B | 0.0705 (17) | 0.0530 (18) | 0.0652 (17) | −0.0023 (13) | −0.0135 (13) | −0.0089 (14) |
F1A | 0.0818 (11) | 0.0822 (13) | 0.0683 (11) | −0.0038 (9) | −0.0120 (8) | −0.0162 (9) |
F1B | 0.0915 (13) | 0.1073 (17) | 0.0705 (12) | −0.0247 (11) | 0.0133 (9) | −0.0175 (11) |
F2A | 0.0907 (12) | 0.1068 (17) | 0.0681 (11) | −0.0041 (10) | 0.0228 (9) | −0.0287 (11) |
F2B | 0.0924 (12) | 0.0889 (15) | 0.0721 (11) | −0.0100 (10) | −0.0264 (9) | −0.0261 (10) |
F3A | 0.1449 (18) | 0.0628 (14) | 0.0967 (15) | −0.0310 (12) | −0.0013 (12) | −0.0154 (11) |
F3B | 0.1466 (19) | 0.0689 (15) | 0.0959 (15) | 0.0286 (13) | −0.0114 (13) | −0.0162 (11) |
N1A | 0.0545 (11) | 0.0558 (15) | 0.0480 (12) | −0.0116 (10) | 0.0044 (8) | −0.0089 (10) |
N1B | 0.0518 (11) | 0.0557 (15) | 0.0469 (12) | −0.0052 (9) | −0.0083 (8) | −0.0066 (10) |
O1A | 0.0774 (12) | 0.0518 (12) | 0.0510 (11) | −0.0045 (9) | 0.0092 (8) | −0.0061 (9) |
O1B | 0.0795 (12) | 0.0462 (12) | 0.0521 (11) | −0.0073 (8) | −0.0152 (9) | −0.0062 (9) |
O2A | 0.0882 (15) | 0.0748 (17) | 0.0522 (12) | −0.0072 (12) | 0.0012 (10) | 0.0040 (11) |
O2B | 0.0907 (15) | 0.0711 (16) | 0.0505 (11) | −0.0182 (12) | −0.0119 (9) | 0.0031 (10) |
Geometric parameters (Å, º) top
C1A—C6A | 1.402 (4) | C8B—C9B | 1.388 (4) |
C1A—C2A | 1.403 (4) | C8B—C13B | 1.397 (4) |
C1A—C7A | 1.442 (4) | C8B—N1B | 1.415 (4) |
C1B—C2B | 1.405 (3) | C9A—C10A | 1.387 (5) |
C1B—C6B | 1.410 (4) | C9A—H9A | 0.93 |
C1B—C7B | 1.444 (4) | C9B—C10B | 1.393 (5) |
C2A—O1A | 1.359 (3) | C9B—H9B | 0.93 |
C2A—C3A | 1.390 (4) | C10A—C11A | 1.366 (5) |
C2B—O1B | 1.360 (3) | C10A—H10A | 0.93 |
C2B—C3B | 1.383 (4) | C10B—C11B | 1.372 (5) |
C3A—O2A | 1.363 (3) | C10B—H10B | 0.93 |
C3A—C4A | 1.375 (4) | C11A—C12A | 1.382 (5) |
C3B—O2B | 1.368 (3) | C11A—H11A | 0.93 |
C3B—C4B | 1.378 (4) | C11B—C12B | 1.374 (5) |
C4A—C5A | 1.390 (5) | C11B—H11B | 0.93 |
C4A—H4A | 0.93 | C12A—C13A | 1.383 (4) |
C4B—C5B | 1.391 (4) | C12A—H12A | 0.93 |
C4B—H4B | 0.93 | C12B—C13B | 1.394 (4) |
C5A—C6A | 1.372 (5) | C12B—H12B | 0.93 |
C5A—H5A | 0.93 | C13A—C14A | 1.487 (4) |
C5B—C6B | 1.359 (5) | C13B—C14B | 1.490 (4) |
C5B—H5B | 0.93 | C14A—F3A | 1.333 (4) |
C6A—H6A | 0.93 | C14A—F1A | 1.341 (3) |
C6B—H6B | 0.93 | C14A—F2A | 1.345 (3) |
C7A—N1A | 1.286 (3) | C14B—F1B | 1.334 (4) |
C7A—H7A | 0.93 | C14B—F3B | 1.335 (3) |
C7B—N1B | 1.286 (3) | C14B—F2B | 1.338 (3) |
C7B—H7B | 0.93 | O1A—H1A | 0.93 (5) |
C8A—C9A | 1.397 (4) | O1B—H1B | 0.90 (4) |
C8A—C13A | 1.401 (4) | O2A—H2A | 0.81 (5) |
C8A—N1A | 1.414 (4) | O2B—H2B | 0.84 (5) |
| | | |
C6A—C1A—C2A | 118.8 (3) | C10A—C9A—C8A | 119.7 (3) |
C6A—C1A—C7A | 120.7 (3) | C10A—C9A—H9A | 120.2 |
C2A—C1A—C7A | 120.5 (2) | C8A—C9A—H9A | 120.2 |
C2B—C1B—C6B | 118.3 (3) | C8B—C9B—C10B | 119.7 (3) |
C2B—C1B—C7B | 121.2 (2) | C8B—C9B—H9B | 120.2 |
C6B—C1B—C7B | 120.5 (2) | C10B—C9B—H9B | 120.2 |
O1A—C2A—C3A | 117.6 (2) | C11A—C10A—C9A | 120.8 (3) |
O1A—C2A—C1A | 122.2 (2) | C11A—C10A—H10A | 119.6 |
C3A—C2A—C1A | 120.2 (3) | C9A—C10A—H10A | 119.6 |
O1B—C2B—C3B | 117.8 (2) | C11B—C10B—C9B | 120.8 (3) |
O1B—C2B—C1B | 121.7 (2) | C11B—C10B—H10B | 119.6 |
C3B—C2B—C1B | 120.5 (2) | C9B—C10B—H10B | 119.6 |
O2A—C3A—C4A | 119.2 (3) | C10A—C11A—C12A | 120.3 (3) |
O2A—C3A—C2A | 121.0 (3) | C10A—C11A—H11A | 119.8 |
C4A—C3A—C2A | 119.8 (3) | C12A—C11A—H11A | 119.8 |
O2B—C3B—C4B | 119.2 (3) | C10B—C11B—C12B | 120.1 (3) |
O2B—C3B—C2B | 121.1 (3) | C10B—C11B—H11B | 120.0 |
C4B—C3B—C2B | 119.7 (2) | C12B—C11B—H11B | 120.0 |
C3A—C4A—C5A | 120.6 (3) | C11A—C12A—C13A | 120.0 (3) |
C3A—C4A—H4A | 119.7 | C11A—C12A—H12A | 120.0 |
C5A—C4A—H4A | 119.7 | C13A—C12A—H12A | 120.0 |
C3B—C4B—C5B | 120.5 (3) | C11B—C12B—C13B | 120.1 (3) |
C3B—C4B—H4B | 119.7 | C11B—C12B—H12B | 119.9 |
C5B—C4B—H4B | 119.7 | C13B—C12B—H12B | 119.9 |
C6A—C5A—C4A | 120.1 (3) | C12A—C13A—C8A | 120.2 (3) |
C6A—C5A—H5A | 120.0 | C12A—C13A—C14A | 119.3 (3) |
C4A—C5A—H5A | 120.0 | C8A—C13A—C14A | 120.5 (2) |
C6B—C5B—C4B | 120.3 (3) | C12B—C13B—C8B | 120.0 (3) |
C6B—C5B—H5B | 119.9 | C12B—C13B—C14B | 119.6 (3) |
C4B—C5B—H5B | 119.9 | C8B—C13B—C14B | 120.4 (2) |
C5A—C6A—C1A | 120.5 (3) | F3A—C14A—F1A | 105.8 (2) |
C5A—C6A—H6A | 119.7 | F3A—C14A—F2A | 106.2 (2) |
C1A—C6A—H6A | 119.7 | F1A—C14A—F2A | 105.0 (2) |
C5B—C6B—C1B | 120.7 (3) | F3A—C14A—C13A | 112.8 (2) |
C5B—C6B—H6B | 119.7 | F1A—C14A—C13A | 114.2 (2) |
C1B—C6B—H6B | 119.7 | F2A—C14A—C13A | 112.1 (2) |
N1A—C7A—C1A | 121.5 (2) | F1B—C14B—F3B | 106.5 (3) |
N1A—C7A—H7A | 119.3 | F1B—C14B—F2B | 105.5 (3) |
C1A—C7A—H7A | 119.3 | F3B—C14B—F2B | 105.4 (2) |
N1B—C7B—C1B | 121.5 (2) | F1B—C14B—C13B | 113.6 (2) |
N1B—C7B—H7B | 119.2 | F3B—C14B—C13B | 112.7 (3) |
C1B—C7B—H7B | 119.2 | F2B—C14B—C13B | 112.4 (2) |
C9A—C8A—C13A | 119.0 (3) | C7A—N1A—C8A | 121.1 (2) |
C9A—C8A—N1A | 121.8 (3) | C7B—N1B—C8B | 120.7 (2) |
C13A—C8A—N1A | 119.1 (2) | C2A—O1A—H1A | 108 (3) |
C9B—C8B—C13B | 119.3 (3) | C2B—O1B—H1B | 109 (2) |
C9B—C8B—N1B | 121.5 (3) | C3A—O2A—H2A | 110 (3) |
C13B—C8B—N1B | 119.1 (2) | C3B—O2B—H2B | 110 (3) |
| | | |
C6A—C1A—C2A—O1A | 179.8 (2) | C8A—C9A—C10A—C11A | 0.0 (5) |
C7A—C1A—C2A—O1A | −1.2 (3) | C8B—C9B—C10B—C11B | −0.3 (4) |
C6A—C1A—C2A—C3A | −1.4 (3) | C9A—C10A—C11A—C12A | 0.5 (5) |
C7A—C1A—C2A—C3A | 177.6 (2) | C9B—C10B—C11B—C12B | 2.1 (4) |
C6B—C1B—C2B—O1B | 179.8 (2) | C10A—C11A—C12A—C13A | 0.0 (5) |
C7B—C1B—C2B—O1B | −1.4 (3) | C10B—C11B—C12B—C13B | −1.3 (4) |
C6B—C1B—C2B—C3B | −1.8 (3) | C11A—C12A—C13A—C8A | −0.9 (4) |
C7B—C1B—C2B—C3B | 177.0 (2) | C11A—C12A—C13A—C14A | 178.0 (3) |
O1A—C2A—C3A—O2A | 0.2 (4) | C9A—C8A—C13A—C12A | 1.5 (4) |
C1A—C2A—C3A—O2A | −178.6 (2) | N1A—C8A—C13A—C12A | 177.3 (2) |
O1A—C2A—C3A—C4A | 179.8 (2) | C9A—C8A—C13A—C14A | −177.5 (2) |
C1A—C2A—C3A—C4A | 0.9 (4) | N1A—C8A—C13A—C14A | −1.6 (3) |
O1B—C2B—C3B—O2B | 0.7 (4) | C11B—C12B—C13B—C8B | −1.3 (4) |
C1B—C2B—C3B—O2B | −177.8 (2) | C11B—C12B—C13B—C14B | 178.2 (3) |
O1B—C2B—C3B—C4B | −179.8 (2) | C9B—C8B—C13B—C12B | 3.1 (3) |
C1B—C2B—C3B—C4B | 1.7 (4) | N1B—C8B—C13B—C12B | −179.5 (2) |
O2A—C3A—C4A—C5A | 179.6 (3) | C9B—C8B—C13B—C14B | −176.4 (2) |
C2A—C3A—C4A—C5A | 0.0 (4) | N1B—C8B—C13B—C14B | 1.0 (3) |
O2B—C3B—C4B—C5B | 178.9 (3) | C12A—C13A—C14A—F3A | 8.6 (4) |
C2B—C3B—C4B—C5B | −0.6 (4) | C8A—C13A—C14A—F3A | −172.4 (2) |
C3A—C4A—C5A—C6A | −0.5 (4) | C12A—C13A—C14A—F1A | 129.5 (3) |
C3B—C4B—C5B—C6B | −0.4 (5) | C8A—C13A—C14A—F1A | −51.5 (3) |
C4A—C5A—C6A—C1A | 0.0 (4) | C12A—C13A—C14A—F2A | −111.2 (3) |
C2A—C1A—C6A—C5A | 1.0 (4) | C8A—C13A—C14A—F2A | 67.8 (3) |
C7A—C1A—C6A—C5A | −178.1 (2) | C12B—C13B—C14B—F1B | 120.8 (3) |
C4B—C5B—C6B—C1B | 0.3 (5) | C8B—C13B—C14B—F1B | −59.7 (3) |
C2B—C1B—C6B—C5B | 0.8 (4) | C12B—C13B—C14B—F3B | −0.5 (4) |
C7B—C1B—C6B—C5B | −178.0 (3) | C8B—C13B—C14B—F3B | 179.0 (2) |
C6A—C1A—C7A—N1A | 178.7 (2) | C12B—C13B—C14B—F2B | −119.4 (3) |
C2A—C1A—C7A—N1A | −0.3 (3) | C8B—C13B—C14B—F2B | 60.1 (3) |
C2B—C1B—C7B—N1B | 0.6 (4) | C1A—C7A—N1A—C8A | 179.4 (2) |
C6B—C1B—C7B—N1B | 179.4 (2) | C9A—C8A—N1A—C7A | −40.1 (3) |
C13A—C8A—C9A—C10A | −1.0 (4) | C13A—C8A—N1A—C7A | 144.2 (2) |
N1A—C8A—C9A—C10A | −176.8 (2) | C1B—C7B—N1B—C8B | 179.6 (2) |
C13B—C8B—C9B—C10B | −2.3 (4) | C9B—C8B—N1B—C7B | −38.9 (3) |
N1B—C8B—C9B—C10B | −179.7 (2) | C13B—C8B—N1B—C7B | 143.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2A···O1Ai | 0.81 (5) | 2.10 (5) | 2.834 (3) | 149 (5) |
O2B—H2B···O1Bii | 0.84 (5) | 2.08 (4) | 2.839 (3) | 150 (4) |
O1A—H1A···N1A | 0.93 (5) | 1.74 (4) | 2.568 (3) | 147 (4) |
O1B—H1B···N1B | 0.90 (4) | 1.79 (4) | 2.583 (3) | 146 (3) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y, −z+2. |
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