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The title compound, C13H19NO3, crystallizes with two mol­ecules, A and B, in the asymmetric unit. Inter­molecular O—H...O hydrogen bonds link symmetry-related mol­ecules into infinite chains parallel to the [101] direction, with short O...O distances of 2.534 (2) and 2.618 (2) Å in the chains of A and B mol­ecules, respectively. Inter­molecular N—H...O hydrogen bonds cross-link these two chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045417/cv2133sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045417/cv2133Isup2.hkl
Contains datablock I

CCDC reference: 629636

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.123
  • Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11B PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.35 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H19 N O3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Acetamidoadamantane-1-carboxylic acid top
Crystal data top
C13H19NO3F(000) = 1024
Mr = 237.29Dx = 1.314 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 13.3487 (6) ÅCell parameters from 25 reflections
b = 10.5295 (5) Åθ = 9–17.3°
c = 17.2793 (7) ŵ = 0.76 mm1
β = 99.073 (3)°T = 293 K
V = 2398.31 (18) Å3Prism, colourless
Z = 80.3 × 0.15 × 0.15 mm
Data collection top
Enraf–Nonius TurboCAD4
diffractometer
Rint = 0.014
non–profiled ω/2θ scansθmax = 76.5°, θmin = 3.9°
Absorption correction: ψ scan
(8 reflections; North et al., 1968)
h = 160
Tmin = 0.845, Tmax = 0.892k = 130
5262 measured reflectionsl = 2121
5043 independent reflections3 standard reflections every 120 min
3856 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2All H-atom parameters refined
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0561P)2 + 0.8403P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.043(Δ/σ)max < 0.001
wR(F2) = 0.123Δρmax = 0.28 e Å3
S = 1.03Δρmin = 0.30 e Å3
5043 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
460 parametersExtinction coefficient: 0.00042 (10)
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.73236 (10)0.76432 (15)0.33889 (8)0.0287 (3)
C2A0.74078 (11)0.72847 (17)0.42334 (8)0.0319 (3)
C3A0.63553 (10)0.72823 (15)0.47430 (8)0.0288 (3)
C4A0.58878 (12)0.86097 (16)0.47326 (9)0.0359 (4)
C5A0.58021 (13)0.89759 (17)0.38859 (10)0.0409 (4)
C6A0.51263 (12)0.8023 (2)0.35493 (11)0.0467 (5)
C7A0.55802 (12)0.67003 (18)0.35652 (10)0.0396 (4)
C8A0.66310 (12)0.66742 (17)0.30629 (9)0.0353 (3)
C9A0.68504 (13)0.89718 (16)0.33762 (10)0.0368 (4)
C10A0.56738 (12)0.63276 (17)0.44058 (9)0.0359 (4)
C11A0.83567 (11)0.75888 (18)0.28739 (9)0.0376 (4)
C12A0.57947 (11)0.67198 (16)0.61536 (9)0.0345 (3)
C13A0.61433 (15)0.6220 (2)0.68769 (10)0.0436 (4)
N1A0.65137 (10)0.69065 (15)0.55341 (7)0.0363 (3)
O1A0.83654 (10)0.81748 (16)0.22049 (7)0.0590 (4)
O2A0.90778 (9)0.70351 (18)0.30471 (8)0.0676 (5)
O3A0.48873 (8)0.69180 (14)0.61250 (7)0.0485 (3)
H1A0.900 (2)0.810 (3)0.1876 (17)0.092 (9)*
H1C0.7123 (15)0.6789 (19)0.5608 (11)0.044 (5)*
H2A0.7709 (14)0.641 (2)0.4259 (11)0.046 (5)*
H2B0.7850 (14)0.7870 (18)0.4469 (11)0.041 (5)*
H4A0.6324 (13)0.9179 (19)0.4965 (11)0.041 (5)*
H4B0.5214 (14)0.8607 (17)0.5057 (11)0.039 (5)*
H5A0.5506 (14)0.980 (2)0.3864 (11)0.048 (5)*
H6A0.4417 (16)0.807 (2)0.3880 (13)0.061 (6)*
H6B0.5069 (15)0.8244 (19)0.2985 (13)0.052 (6)*
H7A0.5151 (14)0.6095 (19)0.3358 (11)0.046 (5)*
H8A0.6576 (14)0.6883 (18)0.2505 (12)0.046 (5)*
H8B0.6965 (15)0.580 (2)0.3079 (12)0.053 (6)*
H9A0.6780 (13)0.9217 (18)0.2830 (11)0.044 (5)*
H9B0.7306 (13)0.9577 (18)0.3570 (10)0.040 (5)*
H10A0.4999 (14)0.6333 (18)0.4722 (11)0.043 (5)*
H10B0.5973 (14)0.545 (2)0.4427 (11)0.050 (5)*
H13A0.5703 (17)0.648 (2)0.7326 (14)0.069 (7)*
H13B0.6856 (17)0.647 (2)0.6910 (13)0.059 (6)*
H13C0.615 (2)0.529 (3)0.6859 (16)0.098 (9)*
C1B0.53434 (10)0.74181 (15)0.06525 (8)0.0315 (3)
C2B0.52337 (11)0.78781 (17)0.01738 (9)0.0328 (3)
C3B0.62774 (10)0.79710 (15)0.06911 (8)0.0298 (3)
C4B0.69484 (13)0.88976 (17)0.03180 (9)0.0366 (4)
C5B0.70661 (12)0.84276 (17)0.05016 (10)0.0386 (4)
C6B0.75590 (12)0.71182 (19)0.04411 (11)0.0439 (4)
C7B0.68894 (12)0.61968 (17)0.00734 (10)0.0387 (4)
C8B0.58580 (12)0.61117 (16)0.06029 (10)0.0365 (4)
C9B0.60224 (13)0.83667 (17)0.10146 (9)0.0367 (4)
C10B0.67611 (13)0.66462 (16)0.07496 (10)0.0374 (4)
C11B0.43115 (12)0.73489 (18)0.11673 (9)0.0398 (4)
C12B0.68156 (12)0.86865 (17)0.20803 (9)0.0378 (4)
C13B0.64610 (18)0.9352 (2)0.27554 (12)0.0534 (5)
N1B0.61043 (10)0.84525 (14)0.14589 (7)0.0362 (3)
O1B0.43275 (10)0.67524 (18)0.18276 (8)0.0673 (5)
O2B0.35546 (10)0.7804 (2)0.10010 (9)0.0860 (7)
O3B0.77193 (9)0.84158 (13)0.20933 (7)0.0476 (3)
H1B0.370 (2)0.672 (3)0.2128 (17)0.091 (9)*
H1D0.5492 (16)0.8551 (19)0.1528 (11)0.047 (6)*
H2C0.4788 (14)0.7280 (18)0.0423 (11)0.045 (5)*
H2D0.4903 (15)0.873 (2)0.0147 (11)0.050 (5)*
H4C0.7643 (14)0.8973 (18)0.0650 (11)0.042 (5)*
H4D0.6623 (14)0.973 (2)0.0298 (11)0.047 (5)*
H5B0.7494 (14)0.9006 (18)0.0744 (11)0.043 (5)*
H6C0.8233 (17)0.716 (2)0.0104 (13)0.061 (6)*
H6D0.7668 (14)0.6777 (19)0.0994 (12)0.049 (5)*
H7B0.7219 (15)0.537 (2)0.0037 (11)0.054 (6)*
H8C0.5959 (13)0.5814 (17)0.1149 (11)0.040 (5)*
H8D0.5419 (15)0.550 (2)0.0391 (12)0.054 (6)*
H9C0.5686 (15)0.925 (2)0.1054 (12)0.056 (6)*
H9D0.6095 (13)0.8077 (18)0.1555 (11)0.042 (5)*
H10C0.6296 (14)0.6066 (19)0.0992 (11)0.045 (5)*
H10D0.7432 (14)0.6676 (17)0.1076 (11)0.042 (5)*
H13D0.5744 (18)0.922 (2)0.2769 (13)0.070 (7)*
H13E0.658 (2)1.026 (3)0.2695 (16)0.093 (9)*
H13F0.6861 (19)0.908 (3)0.3255 (16)0.083 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0230 (7)0.0369 (8)0.0242 (7)0.0000 (6)0.0028 (5)0.0009 (6)
C2A0.0221 (7)0.0463 (9)0.0257 (7)0.0009 (6)0.0015 (5)0.0012 (6)
C3A0.0231 (6)0.0389 (8)0.0223 (6)0.0017 (6)0.0027 (5)0.0004 (6)
C4A0.0331 (8)0.0379 (9)0.0326 (8)0.0006 (7)0.0075 (6)0.0065 (7)
C5A0.0404 (9)0.0395 (9)0.0384 (9)0.0144 (7)0.0076 (7)0.0041 (7)
C6A0.0255 (8)0.0748 (13)0.0385 (9)0.0064 (8)0.0012 (7)0.0071 (9)
C7A0.0327 (8)0.0526 (10)0.0336 (8)0.0146 (7)0.0054 (6)0.0017 (7)
C8A0.0390 (8)0.0397 (9)0.0260 (7)0.0015 (7)0.0012 (6)0.0052 (6)
C9A0.0378 (8)0.0347 (9)0.0341 (8)0.0007 (7)0.0062 (7)0.0020 (7)
C10A0.0323 (8)0.0406 (9)0.0327 (8)0.0097 (7)0.0010 (6)0.0010 (7)
C11A0.0276 (7)0.0550 (10)0.0276 (7)0.0022 (7)0.0036 (6)0.0014 (7)
C12A0.0319 (8)0.0428 (9)0.0265 (7)0.0026 (6)0.0028 (6)0.0024 (6)
C13A0.0452 (10)0.0546 (12)0.0297 (8)0.0030 (8)0.0014 (7)0.0023 (8)
N1A0.0250 (6)0.0563 (9)0.0260 (6)0.0010 (6)0.0009 (5)0.0017 (6)
O1A0.0376 (7)0.0977 (12)0.0352 (6)0.0150 (7)0.0147 (5)0.0190 (7)
O2A0.0310 (6)0.1223 (14)0.0451 (7)0.0220 (7)0.0076 (5)0.0205 (8)
O3A0.0290 (6)0.0829 (10)0.0298 (6)0.0014 (6)0.0069 (4)0.0035 (6)
C1B0.0245 (7)0.0419 (9)0.0268 (7)0.0024 (6)0.0003 (5)0.0016 (6)
C2B0.0239 (7)0.0467 (9)0.0266 (7)0.0037 (6)0.0005 (5)0.0021 (6)
C3B0.0250 (7)0.0381 (8)0.0250 (7)0.0001 (6)0.0001 (5)0.0007 (6)
C4B0.0362 (8)0.0388 (9)0.0341 (8)0.0062 (7)0.0031 (6)0.0014 (7)
C5B0.0348 (8)0.0472 (10)0.0348 (8)0.0121 (7)0.0090 (6)0.0004 (7)
C6B0.0241 (7)0.0621 (12)0.0456 (10)0.0033 (7)0.0054 (7)0.0098 (8)
C7B0.0342 (8)0.0382 (9)0.0416 (9)0.0110 (7)0.0008 (7)0.0015 (7)
C8B0.0351 (8)0.0364 (9)0.0368 (8)0.0032 (7)0.0022 (6)0.0023 (7)
C9B0.0408 (9)0.0420 (9)0.0269 (7)0.0008 (7)0.0045 (6)0.0026 (7)
C10B0.0356 (8)0.0394 (9)0.0344 (8)0.0044 (7)0.0029 (7)0.0053 (7)
C11B0.0279 (8)0.0611 (11)0.0290 (7)0.0029 (7)0.0003 (6)0.0039 (7)
C12B0.0375 (8)0.0446 (9)0.0289 (7)0.0064 (7)0.0017 (6)0.0025 (7)
C13B0.0600 (13)0.0616 (14)0.0370 (10)0.0063 (10)0.0024 (9)0.0123 (9)
N1B0.0295 (7)0.0506 (9)0.0275 (6)0.0011 (6)0.0014 (5)0.0038 (6)
O1B0.0373 (7)0.1177 (14)0.0416 (7)0.0126 (8)0.0100 (6)0.0319 (8)
O2B0.0309 (7)0.1649 (19)0.0570 (9)0.0271 (9)0.0086 (6)0.0440 (11)
O3B0.0337 (6)0.0701 (9)0.0347 (6)0.0039 (6)0.0077 (5)0.0022 (6)
Geometric parameters (Å, º) top
C1A—C2A1.529 (2)C1B—C8B1.534 (2)
C1A—C8A1.542 (2)C1B—C11B1.519 (2)
C1A—C9A1.536 (2)C2B—C3B1.5352 (19)
C1A—C11A1.5198 (19)C2B—C1B1.536 (2)
C2A—H2A1.01 (2)C2B—H2C1.008 (19)
C2A—H2B0.984 (19)C2B—H2D1.00 (2)
C3A—C2A1.5359 (18)C3B—C4B1.534 (2)
C3A—C4A1.532 (2)C3B—C10B1.534 (2)
C3A—C10A1.531 (2)C4B—H4C1.013 (18)
C3A—N1A1.4699 (19)C4B—H4D0.97 (2)
C4A—C5A1.535 (2)C5B—C6B1.524 (3)
C4A—H4B0.982 (18)C5B—C4B1.531 (2)
C4A—H4A0.966 (19)C5B—H5B0.974 (19)
C5A—C6A1.525 (3)C6B—C7B1.524 (3)
C5A—H5A0.95 (2)C6B—H6C0.99 (2)
C6A—H6B1.02 (2)C6B—H6D1.05 (2)
C6A—H6A1.03 (2)C7B—H7B0.97 (2)
C7A—C6A1.521 (3)C8B—C7B1.531 (2)
C7A—C10A1.529 (2)C8B—H8C1.024 (18)
C7A—H7A0.96 (2)C8B—H8D0.98 (2)
C8A—C7A1.529 (2)C9B—C5B1.530 (2)
C8A—H8B1.03 (2)C9B—C1B1.546 (2)
C8A—H8A1.00 (2)C9B—H9D1.001 (19)
C9A—C5A1.531 (2)C9B—H9C1.03 (2)
C9A—H9A0.996 (19)C10B—C7B1.534 (2)
C9A—H9B0.976 (19)C10B—H10D0.981 (19)
C10A—H10A0.976 (19)C10B—H10C1.008 (19)
C10A—H10B1.01 (2)C11B—O2B1.194 (2)
C12A—C13A1.496 (2)C13B—C12B1.500 (3)
C13A—H13B1.00 (2)C13B—H13D0.97 (2)
C13A—H13A0.94 (2)C13B—H13F0.98 (3)
C13A—H13C0.98 (3)C13B—H13E0.98 (3)
N1A—C12A1.3348 (19)N1B—C12B1.3393 (19)
N1A—H1C0.85 (2)N1B—C3B1.4720 (19)
O1A—C11A1.309 (2)N1B—H1D0.85 (2)
O1A—H1A0.95 (3)O1B—C11B1.305 (2)
O2A—C11A1.203 (2)O1B—H1B0.92 (3)
O3A—C12A1.2378 (19)O3B—C12B1.236 (2)
C1A—C9A—H9A110.5 (11)C3B—C4B—H4D107.4 (11)
C1A—C8A—H8B107.3 (11)C4B—C3B—C10B109.79 (13)
C1A—C2A—C3A110.45 (12)C4B—C3B—C2B109.40 (13)
C1A—C9A—H9B108.0 (11)C4B—C5B—H5B110.4 (11)
C1A—C2A—H2B112.2 (11)C5B—C4B—C3B109.58 (13)
C1A—C2A—H2A110.9 (11)C5B—C4B—H4C109.3 (10)
C1A—C8A—H8A110.2 (11)C5B—C6B—C7B109.22 (13)
C2A—C1A—C9A109.31 (13)C5B—C6B—H6C109.7 (13)
C2A—C1A—C8A108.90 (13)C5B—C9B—C1B109.32 (13)
C3A—C2A—H2B108.5 (11)C5B—C9B—H9D109.9 (10)
C3A—C2A—H2A107.9 (11)C5B—C9B—H9C110.3 (11)
C3A—N1A—H1C117.4 (13)C5B—C6B—H6D111.6 (11)
C3A—C4A—C5A109.41 (13)C6B—C5B—C9B110.22 (14)
C3A—C10A—H10A109.5 (11)C6B—C5B—C4B109.58 (15)
C3A—C10A—H10B108.9 (11)C6B—C5B—H5B108.6 (11)
C3A—C4A—H4B109.2 (11)C6B—C7B—C8B108.62 (14)
C3A—C4A—H4A106.8 (11)C6B—C7B—C10B110.41 (15)
C4A—C3A—C2A109.22 (12)C6B—C7B—H7B107.9 (12)
C4A—C5A—H5A111.1 (12)C6B—C7B—C8B108.62 (14)
C5A—C4A—H4A112.4 (11)C6B—C7B—C10B110.41 (15)
C5A—C9A—C1A109.56 (13)C6B—C7B—H7B107.9 (12)
C5A—C9A—H9A109.3 (10)C7B—C10B—C3B109.08 (13)
C5A—C9A—H9B111.3 (10)C7B—C10B—H10D108.5 (11)
C5A—C4A—H4B110.2 (10)C7B—C10B—H10C111.3 (11)
C6A—C7A—C10A110.17 (15)C7B—C8B—C1B109.48 (13)
C6A—C7A—C8A109.79 (14)C7B—C8B—H8C109.4 (10)
C6A—C7A—H7A109.7 (11)C7B—C8B—H8D110.4 (12)
C6A—C5A—C9A108.71 (14)C7B—C6B—H6C108.9 (13)
C6A—C5A—C4A109.63 (15)C7B—C6B—H6D109.6 (11)
C6A—C5A—H5A107.9 (12)C8B—C7B—C10B110.54 (14)
C7A—C8A—C1A109.27 (12)C8B—C7B—H7B109.9 (12)
C7A—C8A—H8B111.4 (11)C8B—C1B—C2B109.77 (13)
C7A—C8A—H8A110.0 (11)C8B—C1B—C9B108.43 (13)
C7A—C10A—C3A109.61 (13)C8B—C7B—C10B110.54 (14)
C7A—C10A—H10A108.9 (11)C8B—C7B—H7B109.9 (12)
C7A—C10A—H10B111.2 (11)C9B—C5B—C4B109.42 (14)
C8A—C7A—H7A108.9 (11)C9B—C5B—H5B108.6 (11)
C9A—C5A—C4A110.42 (14)C10B—C3B—C2B108.32 (13)
C9A—C5A—H5A109.1 (12)C10B—C7B—H7B109.4 (12)
C9A—C1A—C8A109.01 (13)C10B—C7B—H7B109.4 (12)
C10A—C7A—C8A109.25 (14)C11B—C1B—C8B110.27 (13)
C10A—C7A—H7A109.0 (12)C11B—C1B—C2B110.41 (12)
C10A—C3A—C4A109.08 (13)C11B—C1B—C9B109.23 (13)
C10A—C3A—C2A109.12 (12)C12B—C13B—H13D112.7 (14)
C11A—O1A—H1A111.8 (17)C12B—C13B—H13F110.8 (15)
C11A—C1A—C2A110.68 (12)C12B—C13B—H13E107.2 (16)
C11A—C1A—C9A111.29 (13)C12B—N1B—C3B126.43 (14)
C11A—C1A—C8A107.58 (12)C12B—N1B—H1D116.1 (13)
C12A—C13A—H13C109.2 (16)C11B—O1B—H1B111.7 (17)
C12A—N1A—C3A126.49 (13)N1B—C3B—C4B110.17 (13)
C12A—N1A—H1C116.1 (13)N1B—C3B—C10B112.22 (12)
C12A—C13A—H13B112.5 (13)N1B—C3B—C2B106.84 (12)
C12A—C13A—H13A110.6 (14)N1B—C12B—C13B116.02 (16)
N1A—C3A—C10A111.00 (13)O1B—C11B—C1B113.36 (14)
N1A—C3A—C4A112.03 (12)O2B—C11B—O1B122.34 (15)
N1A—C3A—C2A106.31 (12)O2B—C11B—C1B124.30 (15)
N1A—C12A—C13A116.28 (15)O3B—C12B—N1B122.58 (16)
O1A—C11A—C1A112.35 (14)O3B—C12B—C13B121.35 (15)
O2A—C11A—O1A123.52 (14)H2C—C2B—H2D107.1 (15)
O2A—C11A—C1A124.09 (15)H2B—C2A—H2A106.6 (15)
O3A—C12A—N1A121.84 (15)H4B—C4A—H4A108.8 (15)
O3A—C12A—C13A121.86 (14)H4C—C4B—H4D108.2 (15)
C1B—C2B—H2C110.4 (11)H6C—C6B—H6D107.8 (16)
C1B—C2B—H2D110.3 (11)H6B—C6A—H6A108.6 (16)
C1B—C9B—H9D109.2 (11)H8B—C8A—H8A108.7 (15)
C1B—C9B—H9C109.5 (11)H8C—C8B—H8D108.4 (15)
C1B—C8B—H8C110.3 (10)H9A—C9A—H9B108.2 (15)
C1B—C8B—H8D108.9 (12)H9D—C9B—H9C108.6 (16)
C2B—C1B—C9B108.68 (13)H10A—C10A—H10B108.7 (15)
C3B—C2B—C1B110.52 (12)H10D—C10B—H10C110.3 (15)
C3B—C2B—H2C109.5 (11)H13A—C13A—H13C109 (2)
C3B—C2B—H2D109.0 (11)H13B—C13A—H13A110.7 (19)
C3B—N1B—H1D117.4 (13)H13B—C13A—H13C105 (2)
C3B—C10B—H10D110.2 (11)H13D—C13B—H13E109 (2)
C3B—C10B—H10C107.3 (11)H13D—C13B—H13F110 (2)
C3B—C4B—H4C110.8 (10)H13F—C13B—H13E107 (2)
C5B—C4B—H4D111.6 (11)
C13A—C12A—N1A—C3A174.35 (16)C13B—C12B—N1B—C3B171.35 (16)
O3A—C12A—N1A—C3A3.9 (3)O3B—C12B—N1B—C3B6.2 (3)
C2A—C1A—C11A—O1A164.46 (15)C2B—C1B—C11B—O1B168.34 (15)
C2A—C1A—C11A—O2A17.9 (2)C2B—C1B—C11B—O2B12.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O3Ai0.95 (3)1.61 (3)2.534 (2)163 (3)
O1B—H1B···O3Bii0.92 (4)1.73 (3)2.618 (2)163 (3)
N1A—H1C···O2Biii0.85 (2)2.17 (2)2.976 (2)158 (2)
N1B—H1D···O2Aiv0.85 (2)2.22 (2)3.006 (2)154 (2)
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x1/2, y+3/2, z1/2; (iii) x+1/2, y+3/2, z1/2; (iv) x1/2, y+3/2, z+1/2.
 

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