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The crystal structure of the title compound, C15H14N2O·CF3CH2OH, which is the 2,2,2-trifluoro­ethanol (TFE) solvate of 5H-dibenzo[b,f]azepine-5-carboxamide (carbamazepine, CBZ), is reported. The asymmetric unit consists of two independent mol­ecules of each component, CBZ and TFE.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010299/wk6047sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010299/wk6047Isup2.hkl
Contains datablock I

CCDC reference: 272124

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.140
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C16A PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C16B PLAT420_ALERT_2_C D-H Without Acceptor N2A - H2AD ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H2AD .. F2A .. 2.65 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 18 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 C2 H3 F3 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS in SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL in SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002).

5H-dibenzo[b,f]azepine-5-carboxamide–2,2,2-trifluoroethanol (1/1) top
Crystal data top
C15H12N2O·C2H3F3OZ = 4
Mr = 336.31F(000) = 696
Triclinic, P1Dx = 1.405 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 10.236 (2) ÅCell parameters from 2681 reflections
b = 12.937 (2) Åθ = 1.7–25.1°
c = 13.614 (2) ŵ = 0.12 mm1
α = 62.419 (2)°T = 173 K
β = 88.218 (2)°Needles, colorless
γ = 84.286 (2)°0.5 × 0.5 × 0.25 mm
V = 1589.8 (5) Å3
Data collection top
Siemens SMART Platform CCD
diffractometer
5632 independent reflections
Radiation source: normal-focus sealed tube4132 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker 2000)
h = 1212
Tmin = 0.940, Tmax = 0.973k = 1515
15796 measured reflectionsl = 1616
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)] = 0.046Hydrogen site location: geom and difmap
wR(F2) = 0.140H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0726P)2 + 0.4499P]
where P = (Fo2 + 2Fc2)/3
5632 reflections(Δ/σ)max < 0.001
433 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.27 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
C15A0.62516 (19)0.62741 (17)0.40291 (15)0.0330 (4)
C14A0.49428 (18)0.81621 (17)0.34867 (15)0.0326 (4)
C13A0.3944 (2)0.8004 (2)0.42477 (17)0.0403 (5)
H13A0.35690.72780.45960.048*
C12A0.3497 (2)0.8896 (2)0.44988 (19)0.0474 (6)
H12A0.28200.87850.50220.057*
C11A0.4041 (2)0.9951 (2)0.39818 (19)0.0503 (6)
H11A0.37391.05680.41520.060*
C10A0.5017 (2)1.01148 (19)0.32223 (18)0.0457 (5)
H10A0.53831.08450.28770.055*
C9A0.54853 (19)0.92335 (17)0.29444 (16)0.0343 (5)
C8A0.6499 (2)0.94552 (18)0.21037 (17)0.0390 (5)
H8AA0.71170.99770.20570.047*
C7A0.6646 (2)0.90058 (17)0.14006 (16)0.0376 (5)
H7AA0.73590.92440.09070.045*
C6A0.58403 (18)0.81870 (17)0.12966 (16)0.0330 (4)
C5A0.5660 (2)0.82508 (19)0.02533 (17)0.0422 (5)
H5AA0.60560.88290.03750.051*
C4A0.4920 (2)0.7493 (2)0.01209 (18)0.0473 (6)
H4AA0.48040.75560.05950.057*
C3A0.4344 (2)0.6641 (2)0.10249 (19)0.0491 (6)
H3AA0.38430.61100.09340.059*
C2A0.4499 (2)0.65625 (19)0.20671 (18)0.0420 (5)
H2AA0.40910.59870.26900.050*
C1A0.52462 (19)0.73229 (17)0.21967 (15)0.0323 (4)
N1A0.54444 (16)0.72083 (13)0.32864 (12)0.0323 (4)
N2A0.64442 (17)0.62216 (15)0.50256 (13)0.0414 (4)
H2AC0.69610.56430.55240.050*
H2AD0.60530.67660.51790.050*
O1A0.67789 (15)0.55317 (12)0.37778 (11)0.0429 (4)
C15B0.89693 (18)0.37364 (16)0.61609 (15)0.0294 (4)
C14B1.00371 (19)0.17696 (17)0.67247 (16)0.0328 (4)
C13B1.1030 (2)0.1769 (2)0.60097 (19)0.0463 (6)
H13B1.15420.24150.56720.056*
C12B1.1275 (2)0.0831 (3)0.5788 (2)0.0600 (7)
H12B1.19500.08340.52920.072*
C11B1.0542 (3)0.0110 (2)0.6284 (2)0.0617 (8)
H11B1.07170.07600.61370.074*
C10B0.9555 (3)0.01112 (19)0.6991 (2)0.0527 (6)
H10B0.90480.07620.73200.063*
C9B0.9280 (2)0.08242 (17)0.72380 (16)0.0378 (5)
C8B0.8224 (2)0.07978 (18)0.79914 (18)0.0444 (5)
H8BA0.75040.03830.80000.053*
C7B0.8144 (2)0.12841 (19)0.86706 (17)0.0444 (5)
H7BA0.73650.11940.90890.053*
C6B0.9118 (2)0.19383 (17)0.88422 (16)0.0372 (5)
C5B0.9286 (3)0.1873 (2)0.98888 (18)0.0502 (6)
H5BA0.87250.14371.04730.060*
C4B1.0247 (3)0.2426 (2)1.00850 (18)0.0527 (6)
H4BA1.03450.23661.08010.063*
C3B1.1070 (2)0.3066 (2)0.92507 (19)0.0473 (6)
H3BA1.17430.34360.93950.057*
C2B1.0917 (2)0.31688 (18)0.82006 (17)0.0379 (5)
H2BA1.14830.36100.76220.045*
C1B0.99361 (18)0.26262 (16)0.79995 (15)0.0306 (4)
N1B0.97371 (15)0.27746 (13)0.68995 (12)0.0296 (4)
N2B0.86852 (17)0.37830 (15)0.51905 (13)0.0390 (4)
H2BC0.81980.43910.46940.047*
H2BD0.89850.32060.50470.047*
O1B0.85597 (14)0.45396 (11)0.63885 (11)0.0365 (3)
C16A0.7567 (2)0.6417 (2)0.7909 (2)0.0504 (6)
C17A0.8727 (2)0.5565 (2)0.81410 (19)0.0474 (6)
H17A0.92780.55660.87260.057*
H17B0.84440.47700.84160.057*
F1A0.68775 (17)0.61783 (17)0.88273 (14)0.0824 (5)
F2A0.67352 (16)0.64098 (17)0.71814 (14)0.0828 (5)
F3A0.7875 (2)0.74988 (13)0.75315 (17)0.0942 (6)
O2A0.94704 (15)0.58468 (14)0.71770 (13)0.0506 (4)
H2AB0.92480.54670.68600.076*
C16B1.2780 (2)0.6423 (2)0.8262 (2)0.0523 (6)
C17B1.2738 (3)0.6305 (2)0.7239 (2)0.0562 (6)
H17C1.35570.65520.68250.067*
H17D1.26810.54730.74310.067*
F1B1.38374 (16)0.58091 (15)0.88957 (14)0.0811 (5)
F2B1.17429 (16)0.60327 (17)0.88993 (13)0.0785 (5)
F3B1.28132 (19)0.75182 (15)0.80840 (16)0.0881 (6)
O2B1.16503 (17)0.69961 (15)0.65666 (13)0.0561 (4)
H2BB1.09840.66220.67710.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C13A0.0361 (11)0.0496 (13)0.0319 (11)0.0033 (9)0.0022 (9)0.0159 (10)
C12A0.0396 (12)0.0645 (16)0.0393 (12)0.0044 (11)0.0004 (10)0.0268 (12)
C11A0.0568 (15)0.0528 (14)0.0462 (13)0.0099 (12)0.0058 (11)0.0295 (12)
C10A0.0545 (14)0.0378 (12)0.0431 (13)0.0002 (10)0.0073 (11)0.0177 (10)
C9A0.0357 (11)0.0325 (10)0.0292 (10)0.0010 (8)0.0060 (8)0.0097 (9)
C14A0.0308 (10)0.0384 (11)0.0257 (10)0.0001 (8)0.0058 (8)0.0126 (9)
C8A0.0394 (11)0.0338 (11)0.0360 (11)0.0093 (9)0.0011 (9)0.0084 (9)
C7A0.0356 (11)0.0372 (11)0.0284 (10)0.0050 (9)0.0025 (8)0.0051 (9)
C6A0.0307 (10)0.0334 (10)0.0272 (10)0.0038 (8)0.0026 (8)0.0087 (8)
C5A0.0436 (12)0.0470 (13)0.0266 (10)0.0017 (10)0.0015 (9)0.0101 (9)
C4A0.0492 (13)0.0608 (15)0.0318 (12)0.0031 (11)0.0075 (10)0.0225 (11)
C3A0.0526 (14)0.0548 (14)0.0474 (14)0.0063 (11)0.0066 (11)0.0294 (12)
C2A0.0473 (13)0.0407 (12)0.0364 (12)0.0094 (10)0.0017 (10)0.0155 (10)
C1A0.0331 (10)0.0350 (10)0.0251 (10)0.0018 (8)0.0032 (8)0.0116 (9)
C15A0.0353 (11)0.0313 (10)0.0260 (10)0.0057 (8)0.0004 (8)0.0074 (8)
N1A0.0382 (9)0.0305 (8)0.0228 (8)0.0016 (7)0.0021 (7)0.0080 (7)
N2A0.0482 (11)0.0433 (10)0.0272 (9)0.0071 (8)0.0075 (8)0.0135 (8)
O1A0.0542 (9)0.0381 (8)0.0316 (8)0.0075 (7)0.0076 (7)0.0139 (7)
C13B0.0359 (12)0.0659 (15)0.0490 (13)0.0002 (10)0.0012 (10)0.0374 (12)
C12B0.0487 (14)0.087 (2)0.0666 (17)0.0161 (14)0.0097 (13)0.0578 (16)
C11B0.0742 (18)0.0548 (16)0.0673 (17)0.0263 (14)0.0302 (15)0.0421 (14)
C10B0.0725 (17)0.0323 (12)0.0489 (14)0.0067 (11)0.0257 (13)0.0155 (11)
C9B0.0423 (12)0.0296 (10)0.0343 (11)0.0051 (9)0.0157 (9)0.0093 (9)
C14B0.0328 (10)0.0353 (11)0.0307 (10)0.0054 (8)0.0087 (8)0.0167 (9)
C8B0.0446 (12)0.0358 (12)0.0399 (12)0.0116 (10)0.0038 (10)0.0050 (10)
C7B0.0421 (12)0.0420 (12)0.0328 (11)0.0051 (10)0.0045 (9)0.0036 (10)
C6B0.0399 (11)0.0357 (11)0.0264 (10)0.0069 (9)0.0018 (9)0.0080 (9)
C5B0.0630 (15)0.0501 (14)0.0268 (11)0.0035 (12)0.0021 (10)0.0104 (10)
C4B0.0724 (17)0.0538 (14)0.0290 (12)0.0131 (13)0.0131 (11)0.0195 (11)
C3B0.0508 (13)0.0493 (13)0.0476 (13)0.0110 (11)0.0173 (11)0.0293 (11)
C2B0.0365 (11)0.0401 (11)0.0391 (12)0.0034 (9)0.0050 (9)0.0211 (10)
C1B0.0324 (10)0.0300 (10)0.0272 (10)0.0075 (8)0.0033 (8)0.0132 (8)
C15B0.0303 (10)0.0279 (10)0.0277 (10)0.0060 (8)0.0005 (8)0.0102 (8)
N1B0.0333 (9)0.0295 (8)0.0239 (8)0.0001 (7)0.0012 (7)0.0111 (7)
N2B0.0507 (11)0.0345 (9)0.0293 (9)0.0033 (8)0.0093 (8)0.0134 (8)
O1B0.0448 (8)0.0308 (7)0.0324 (7)0.0020 (6)0.0080 (6)0.0140 (6)
C16A0.0561 (15)0.0478 (14)0.0535 (15)0.0025 (11)0.0043 (12)0.0288 (12)
C17A0.0505 (13)0.0458 (13)0.0459 (13)0.0059 (10)0.0003 (11)0.0209 (11)
F1A0.0749 (11)0.1083 (14)0.0754 (11)0.0079 (10)0.0116 (9)0.0557 (10)
F2A0.0634 (10)0.1176 (14)0.0835 (12)0.0156 (9)0.0265 (9)0.0631 (11)
F3A0.1127 (15)0.0419 (9)0.1268 (16)0.0008 (9)0.0037 (12)0.0391 (10)
O2A0.0555 (10)0.0557 (10)0.0535 (10)0.0168 (8)0.0060 (8)0.0343 (8)
C16B0.0547 (15)0.0518 (14)0.0543 (15)0.0088 (12)0.0025 (12)0.0270 (12)
C17B0.0659 (17)0.0586 (15)0.0512 (15)0.0110 (13)0.0067 (13)0.0306 (13)
F1B0.0752 (11)0.0923 (12)0.0717 (11)0.0072 (9)0.0198 (9)0.0361 (9)
F2B0.0739 (11)0.1143 (14)0.0520 (9)0.0157 (10)0.0120 (8)0.0418 (9)
F3B0.1151 (14)0.0635 (10)0.1034 (13)0.0082 (9)0.0332 (11)0.0515 (10)
O2B0.0627 (11)0.0634 (11)0.0473 (9)0.0212 (9)0.0030 (8)0.0273 (8)
Geometric parameters (Å, º) top
C13A—C12A1.382 (3)C10B—H10B0.9500
C13A—C14A1.393 (3)C9B—C14B1.396 (3)
C13A—H13A0.9500C9B—C8B1.459 (3)
C12A—C11A1.381 (3)C14B—N1B1.430 (2)
C12A—H12A0.9500C8B—C7B1.335 (3)
C11A—C10A1.374 (3)C8B—H8BA0.9500
C11A—H11A0.9500C7B—C6B1.460 (3)
C10A—C9A1.397 (3)C7B—H7BA0.9500
C10A—H10A0.9500C6B—C1B1.398 (3)
C9A—C14A1.398 (3)C6B—C5B1.403 (3)
C9A—C8A1.466 (3)C5B—C4B1.373 (4)
C14A—N1A1.427 (2)C5B—H5BA0.9500
C8A—C7A1.329 (3)C4B—C3B1.376 (3)
C8A—H8AA0.9500C4B—H4BA0.9500
C7A—C6A1.464 (3)C3B—C2B1.385 (3)
C7A—H7AA0.9500C3B—H3BA0.9500
C6A—C1A1.393 (3)C2B—C1B1.383 (3)
C6A—C5A1.401 (3)C2B—H2BA0.9500
C5A—C4A1.373 (3)C1B—N1B1.437 (2)
C5A—H5AA0.9500C15B—O1B1.247 (2)
C4A—C3A1.380 (3)C15B—N2B1.334 (2)
C4A—H4AA0.9500C15B—N1B1.369 (2)
C3A—C2A1.388 (3)N2B—H2BC0.8800
C3A—H3AA0.9500N2B—H2BD0.8800
C2A—C1A1.380 (3)C16A—F3A1.317 (3)
C2A—H2AA0.9500C16A—F2A1.329 (3)
C1A—N1A1.440 (2)C16A—F1A1.337 (3)
C15A—O1A1.233 (2)C16A—C17A1.472 (3)
C15A—N2A1.346 (2)C17A—O2A1.409 (3)
C15A—N1A1.374 (2)C17A—H17A0.9900
N2A—H2AC0.8800C17A—H17B0.9900
N2A—H2AD0.8800O2A—H2AB0.8400
C13B—C12B1.379 (3)C16B—F3B1.326 (3)
C13B—C14B1.385 (3)C16B—F2B1.334 (3)
C13B—H13B0.9500C16B—F1B1.341 (3)
C12B—C11B1.375 (4)C16B—C17B1.471 (3)
C12B—H12B0.9500C17B—O2B1.409 (3)
C11B—C10B1.373 (4)C17B—H17C0.9900
C11B—H11B0.9500C17B—H17D0.9900
C10B—C9B1.400 (3)O2B—H2BB0.8400
C12A—C13A—C14A120.4 (2)C14B—C9B—C8B122.38 (18)
C12A—C13A—H13A119.8C10B—C9B—C8B120.2 (2)
C14A—C13A—H13A119.8C13B—C14B—C9B120.92 (19)
C11A—C12A—C13A119.4 (2)C13B—C14B—N1B119.74 (18)
C11A—C12A—H12A120.3C9B—C14B—N1B119.26 (17)
C13A—C12A—H12A120.3C7B—C8B—C9B128.0 (2)
C10A—C11A—C12A120.3 (2)C7B—C8B—H8BA116.0
C10A—C11A—H11A119.8C9B—C8B—H8BA116.0
C12A—C11A—H11A119.8C8B—C7B—C6B127.3 (2)
C11A—C10A—C9A121.7 (2)C8B—C7B—H7BA116.3
C11A—C10A—H10A119.2C6B—C7B—H7BA116.3
C9A—C10A—H10A119.2C1B—C6B—C5B117.1 (2)
C10A—C9A—C14A117.51 (19)C1B—C6B—C7B122.52 (18)
C10A—C9A—C8A119.99 (19)C5B—C6B—C7B120.3 (2)
C14A—C9A—C8A122.50 (18)C4B—C5B—C6B121.3 (2)
C13A—C14A—C9A120.64 (19)C4B—C5B—H5BA119.4
C13A—C14A—N1A119.56 (18)C6B—C5B—H5BA119.4
C9A—C14A—N1A119.77 (17)C5B—C4B—C3B120.5 (2)
C7A—C8A—C9A127.06 (19)C5B—C4B—H4BA119.8
C7A—C8A—H8AA116.5C3B—C4B—H4BA119.8
C9A—C8A—H8AA116.5C4B—C3B—C2B119.9 (2)
C8A—C7A—C6A127.73 (19)C4B—C3B—H3BA120.1
C8A—C7A—H7AA116.1C2B—C3B—H3BA120.1
C6A—C7A—H7AA116.1C1B—C2B—C3B119.6 (2)
C1A—C6A—C5A117.55 (18)C1B—C2B—H2BA120.2
C1A—C6A—C7A123.03 (18)C3B—C2B—H2BA120.2
C5A—C6A—C7A119.42 (18)C2B—C1B—C6B121.54 (18)
C4A—C5A—C6A121.3 (2)C2B—C1B—N1B119.74 (17)
C4A—C5A—H5AA119.4C6B—C1B—N1B118.72 (17)
C6A—C5A—H5AA119.4O1B—C15B—N2B121.52 (17)
C5A—C4A—C3A120.2 (2)O1B—C15B—N1B120.97 (16)
C5A—C4A—H4AA119.9N2B—C15B—N1B117.51 (16)
C3A—C4A—H4AA119.9C15B—N1B—C14B121.27 (15)
C4A—C3A—C2A119.8 (2)C15B—N1B—C1B119.05 (15)
C4A—C3A—H3AA120.1C14B—N1B—C1B117.35 (14)
C2A—C3A—H3AA120.1C15B—N2B—H2BC120.0
C1A—C2A—C3A119.8 (2)C15B—N2B—H2BD120.0
C1A—C2A—H2AA120.1H2BC—N2B—H2BD120.0
C3A—C2A—H2AA120.1F3A—C16A—F2A107.5 (2)
C2A—C1A—C6A121.37 (18)F3A—C16A—F1A106.4 (2)
C2A—C1A—N1A119.56 (17)F2A—C16A—F1A105.8 (2)
C6A—C1A—N1A119.06 (17)F3A—C16A—C17A112.7 (2)
O1A—C15A—N2A122.29 (18)F2A—C16A—C17A112.9 (2)
O1A—C15A—N1A120.78 (17)F1A—C16A—C17A111.0 (2)
N2A—C15A—N1A116.93 (17)O2A—C17A—C16A110.59 (19)
C15A—N1A—C14A122.74 (16)O2A—C17A—H17A109.5
C15A—N1A—C1A118.88 (16)C16A—C17A—H17A109.5
C14A—N1A—C1A117.75 (15)O2A—C17A—H17B109.5
C15A—N2A—H2AC120.0C16A—C17A—H17B109.5
C15A—N2A—H2AD120.0H17A—C17A—H17B108.1
H2AC—N2A—H2AD120.0C17A—O2A—H2AB109.5
C12B—C13B—C14B120.1 (2)F3B—C16B—F2B105.7 (2)
C12B—C13B—H13B120.0F3B—C16B—F1B106.32 (19)
C14B—C13B—H13B120.0F2B—C16B—F1B105.9 (2)
C11B—C12B—C13B120.0 (2)F3B—C16B—C17B113.7 (2)
C11B—C12B—H12B120.0F2B—C16B—C17B112.7 (2)
C13B—C12B—H12B120.0F1B—C16B—C17B111.9 (2)
C10B—C11B—C12B120.0 (2)O2B—C17B—C16B110.8 (2)
C10B—C11B—H11B120.0O2B—C17B—H17C109.5
C12B—C11B—H11B120.0C16B—C17B—H17C109.5
C11B—C10B—C9B121.5 (2)O2B—C17B—H17D109.5
C11B—C10B—H10B119.2C16B—C17B—H17D109.5
C9B—C10B—H10B119.2H17C—C17B—H17D108.1
C14B—C9B—C10B117.4 (2)C17B—O2B—H2BB109.5
C14A—C13A—C12A—C11A0.5 (3)C11B—C10B—C9B—C14B0.9 (3)
C13A—C12A—C11A—C10A0.2 (3)C11B—C10B—C9B—C8B179.9 (2)
C12A—C11A—C10A—C9A0.3 (3)C12B—C13B—C14B—C9B0.6 (3)
C11A—C10A—C9A—C14A1.3 (3)C12B—C13B—C14B—N1B176.29 (19)
C11A—C10A—C9A—C8A178.1 (2)C10B—C9B—C14B—C13B0.7 (3)
C12A—C13A—C14A—C9A1.6 (3)C8B—C9B—C14B—C13B179.72 (19)
C12A—C13A—C14A—N1A176.37 (18)C10B—C9B—C14B—N1B176.17 (17)
C10A—C9A—C14A—C13A2.0 (3)C8B—C9B—C14B—N1B2.8 (3)
C8A—C9A—C14A—C13A177.39 (18)C14B—C9B—C8B—C7B31.5 (3)
C10A—C9A—C14A—N1A175.99 (17)C10B—C9B—C8B—C7B149.5 (2)
C8A—C9A—C14A—N1A4.6 (3)C9B—C8B—C7B—C6B1.7 (4)
C10A—C9A—C8A—C7A147.7 (2)C8B—C7B—C6B—C1B32.2 (3)
C14A—C9A—C8A—C7A31.7 (3)C8B—C7B—C6B—C5B146.2 (2)
C9A—C8A—C7A—C6A0.1 (4)C1B—C6B—C5B—C4B2.4 (3)
C8A—C7A—C6A—C1A33.4 (3)C7B—C6B—C5B—C4B176.2 (2)
C8A—C7A—C6A—C5A147.4 (2)C6B—C5B—C4B—C3B0.2 (3)
C1A—C6A—C5A—C4A0.3 (3)C5B—C4B—C3B—C2B1.0 (3)
C7A—C6A—C5A—C4A179.47 (19)C4B—C3B—C2B—C1B0.0 (3)
C6A—C5A—C4A—C3A0.5 (3)C3B—C2B—C1B—C6B2.3 (3)
C5A—C4A—C3A—C2A0.9 (3)C3B—C2B—C1B—N1B177.24 (17)
C4A—C3A—C2A—C1A1.1 (3)C5B—C6B—C1B—C2B3.4 (3)
C3A—C2A—C1A—C6A0.9 (3)C7B—C6B—C1B—C2B175.14 (18)
C3A—C2A—C1A—N1A177.65 (19)C5B—C6B—C1B—N1B176.12 (17)
C5A—C6A—C1A—C2A0.5 (3)C7B—C6B—C1B—N1B5.4 (3)
C7A—C6A—C1A—C2A179.65 (19)O1B—C15B—N1B—C14B169.91 (17)
C5A—C6A—C1A—N1A178.10 (17)N2B—C15B—N1B—C14B10.5 (3)
C7A—C6A—C1A—N1A1.1 (3)O1B—C15B—N1B—C1B7.7 (3)
O1A—C15A—N1A—C14A172.09 (17)N2B—C15B—N1B—C1B172.74 (16)
N2A—C15A—N1A—C14A7.2 (3)C13B—C14B—N1B—C15B80.8 (2)
O1A—C15A—N1A—C1A1.4 (3)C9B—C14B—N1B—C15B96.1 (2)
N2A—C15A—N1A—C1A177.86 (17)C13B—C14B—N1B—C1B116.7 (2)
C13A—C14A—N1A—C15A74.0 (2)C9B—C14B—N1B—C1B66.4 (2)
C9A—C14A—N1A—C15A104.0 (2)C2B—C1B—N1B—C15B84.9 (2)
C13A—C14A—N1A—C1A115.23 (19)C6B—C1B—N1B—C15B94.6 (2)
C9A—C14A—N1A—C1A66.8 (2)C2B—C1B—N1B—C14B112.1 (2)
C2A—C1A—N1A—C15A71.8 (2)C6B—C1B—N1B—C14B68.4 (2)
C6A—C1A—N1A—C15A106.8 (2)F3A—C16A—C17A—O2A58.8 (3)
C2A—C1A—N1A—C14A117.0 (2)F2A—C16A—C17A—O2A63.4 (3)
C6A—C1A—N1A—C14A64.3 (2)F1A—C16A—C17A—O2A178.04 (18)
C14B—C13B—C12B—C11B0.6 (3)F3B—C16B—C17B—O2B57.0 (3)
C13B—C12B—C11B—C10B0.7 (4)F2B—C16B—C17B—O2B63.2 (3)
C12B—C11B—C10B—C9B0.9 (3)F1B—C16B—C17B—O2B177.51 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AC···O1B0.882.052.905 (2)164
N2B—H2BC···O1A0.881.962.820 (2)167
N2B—H2BD···O2Bi0.882.443.035 (2)125
O2A—H2AB···O1B0.841.802.6342 (19)169
O2B—H2BB···O2A0.841.862.698 (2)178
N2A—H2AD···F2A0.882.653.081 (2)111
Symmetry code: (i) x+2, y+1, z+1.
 

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