3-Acetamido­adamantane-1-carboxylic acid

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.

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

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Computing details

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

Crystal data

C13H19NO3	F(000) = 1024
Mr = 237.29	Dx = 1.314 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 13.3487 (6) Å	Cell parameters from 25 reflections
b = 10.5295 (5) Å	θ = 9–17.3°
c = 17.2793 (7) Å	µ = 0.76 mm^−1
β = 99.073 (3)°	T = 293 K
V = 2398.31 (18) Å^3	Prism, colourless
Z = 8	0.3 × 0.15 × 0.15 mm

Data collection

Enraf–Nonius TurboCAD4 diffractometer	Rint = 0.014
non–profiled ω/2θ scans	θmax = 76.5°, θmin = 3.9°
Absorption correction: ψ scan (8 reflections; North et al., 1968)	h = −16→0
Tmin = 0.845, Tmax = 0.892	k = −13→0
5262 measured reflections	l = −21→21
5043 independent reflections	3 standard reflections every 120 min
3856 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.8403P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.043	(Δ/σ)max < 0.001
wR(F^2) = 0.123	Δρmax = 0.28 e Å^−3
S = 1.03	Δρmin = −0.30 e Å^−3
5043 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
460 parameters	Extinction coefficient: 0.00042 (10)
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.73236 (10)	0.76432 (15)	−0.33889 (8)	0.0287 (3)
C2A	0.74078 (11)	0.72847 (17)	−0.42334 (8)	0.0319 (3)
C3A	0.63553 (10)	0.72823 (15)	−0.47430 (8)	0.0288 (3)
C4A	0.58878 (12)	0.86097 (16)	−0.47326 (9)	0.0359 (4)
C5A	0.58021 (13)	0.89759 (17)	−0.38859 (10)	0.0409 (4)
C6A	0.51263 (12)	0.8023 (2)	−0.35493 (11)	0.0467 (5)
C7A	0.55802 (12)	0.67003 (18)	−0.35652 (10)	0.0396 (4)
C8A	0.66310 (12)	0.66742 (17)	−0.30629 (9)	0.0353 (3)
C9A	0.68504 (13)	0.89718 (16)	−0.33762 (10)	0.0368 (4)
C10A	0.56738 (12)	0.63276 (17)	−0.44058 (9)	0.0359 (4)
C11A	0.83567 (11)	0.75888 (18)	−0.28739 (9)	0.0376 (4)
C12A	0.57947 (11)	0.67198 (16)	−0.61536 (9)	0.0345 (3)
C13A	0.61433 (15)	0.6220 (2)	−0.68769 (10)	0.0436 (4)
N1A	0.65137 (10)	0.69065 (15)	−0.55341 (7)	0.0363 (3)
O1A	0.83654 (10)	0.81748 (16)	−0.22049 (7)	0.0590 (4)
O2A	0.90778 (9)	0.70351 (18)	−0.30471 (8)	0.0676 (5)
O3A	0.48873 (8)	0.69180 (14)	−0.61250 (7)	0.0485 (3)
H1A	0.900 (2)	0.810 (3)	−0.1876 (17)	0.092 (9)*
H1C	0.7123 (15)	0.6789 (19)	−0.5608 (11)	0.044 (5)*
H2A	0.7709 (14)	0.641 (2)	−0.4259 (11)	0.046 (5)*
H2B	0.7850 (14)	0.7870 (18)	−0.4469 (11)	0.041 (5)*
H4A	0.6324 (13)	0.9179 (19)	−0.4965 (11)	0.041 (5)*
H4B	0.5214 (14)	0.8607 (17)	−0.5057 (11)	0.039 (5)*
H5A	0.5506 (14)	0.980 (2)	−0.3864 (11)	0.048 (5)*
H6A	0.4417 (16)	0.807 (2)	−0.3880 (13)	0.061 (6)*
H6B	0.5069 (15)	0.8244 (19)	−0.2985 (13)	0.052 (6)*
H7A	0.5151 (14)	0.6095 (19)	−0.3358 (11)	0.046 (5)*
H8A	0.6576 (14)	0.6883 (18)	−0.2505 (12)	0.046 (5)*
H8B	0.6965 (15)	0.580 (2)	−0.3079 (12)	0.053 (6)*
H9A	0.6780 (13)	0.9217 (18)	−0.2830 (11)	0.044 (5)*
H9B	0.7306 (13)	0.9577 (18)	−0.3570 (10)	0.040 (5)*
H10A	0.4999 (14)	0.6333 (18)	−0.4722 (11)	0.043 (5)*
H10B	0.5973 (14)	0.545 (2)	−0.4427 (11)	0.050 (5)*
H13A	0.5703 (17)	0.648 (2)	−0.7326 (14)	0.069 (7)*
H13B	0.6856 (17)	0.647 (2)	−0.6910 (13)	0.059 (6)*
H13C	0.615 (2)	0.529 (3)	−0.6859 (16)	0.098 (9)*
C1B	0.53434 (10)	0.74181 (15)	−0.06525 (8)	0.0315 (3)
C2B	0.52337 (11)	0.78781 (17)	0.01738 (9)	0.0328 (3)
C3B	0.62774 (10)	0.79710 (15)	0.06911 (8)	0.0298 (3)
C4B	0.69484 (13)	0.88976 (17)	0.03180 (9)	0.0366 (4)
C5B	0.70661 (12)	0.84276 (17)	−0.05016 (10)	0.0386 (4)
C6B	0.75590 (12)	0.71182 (19)	−0.04411 (11)	0.0439 (4)
C7B	0.68894 (12)	0.61968 (17)	−0.00734 (10)	0.0387 (4)
C8B	0.58580 (12)	0.61117 (16)	−0.06029 (10)	0.0365 (4)
C9B	0.60224 (13)	0.83667 (17)	−0.10146 (9)	0.0367 (4)
C10B	0.67611 (13)	0.66462 (16)	0.07496 (10)	0.0374 (4)
C11B	0.43115 (12)	0.73489 (18)	−0.11673 (9)	0.0398 (4)
C12B	0.68156 (12)	0.86865 (17)	0.20803 (9)	0.0378 (4)
C13B	0.64610 (18)	0.9352 (2)	0.27554 (12)	0.0534 (5)
N1B	0.61043 (10)	0.84525 (14)	0.14589 (7)	0.0362 (3)
O1B	0.43275 (10)	0.67524 (18)	−0.18276 (8)	0.0673 (5)
O2B	0.35546 (10)	0.7804 (2)	−0.10010 (9)	0.0860 (7)
O3B	0.77193 (9)	0.84158 (13)	0.20933 (7)	0.0476 (3)
H1B	0.370 (2)	0.672 (3)	−0.2128 (17)	0.091 (9)*
H1D	0.5492 (16)	0.8551 (19)	0.1528 (11)	0.047 (6)*
H2C	0.4788 (14)	0.7280 (18)	0.0423 (11)	0.045 (5)*
H2D	0.4903 (15)	0.873 (2)	0.0147 (11)	0.050 (5)*
H4C	0.7643 (14)	0.8973 (18)	0.0650 (11)	0.042 (5)*
H4D	0.6623 (14)	0.973 (2)	0.0298 (11)	0.047 (5)*
H5B	0.7494 (14)	0.9006 (18)	−0.0744 (11)	0.043 (5)*
H6C	0.8233 (17)	0.716 (2)	−0.0104 (13)	0.061 (6)*
H6D	0.7668 (14)	0.6777 (19)	−0.0994 (12)	0.049 (5)*
H7B	0.7219 (15)	0.537 (2)	−0.0037 (11)	0.054 (6)*
H8C	0.5959 (13)	0.5814 (17)	−0.1149 (11)	0.040 (5)*
H8D	0.5419 (15)	0.550 (2)	−0.0391 (12)	0.054 (6)*
H9C	0.5686 (15)	0.925 (2)	−0.1054 (12)	0.056 (6)*
H9D	0.6095 (13)	0.8077 (18)	−0.1555 (11)	0.042 (5)*
H10C	0.6296 (14)	0.6066 (19)	0.0992 (11)	0.045 (5)*
H10D	0.7432 (14)	0.6676 (17)	0.1076 (11)	0.042 (5)*
H13D	0.5744 (18)	0.922 (2)	0.2769 (13)	0.070 (7)*
H13E	0.658 (2)	1.026 (3)	0.2695 (16)	0.093 (9)*
H13F	0.6861 (19)	0.908 (3)	0.3255 (16)	0.083 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0230 (7)	0.0369 (8)	0.0242 (7)	0.0000 (6)	−0.0028 (5)	0.0009 (6)
C2A	0.0221 (7)	0.0463 (9)	0.0257 (7)	0.0009 (6)	−0.0015 (5)	0.0012 (6)
C3A	0.0231 (6)	0.0389 (8)	0.0223 (6)	−0.0017 (6)	−0.0027 (5)	0.0004 (6)
C4A	0.0331 (8)	0.0379 (9)	0.0326 (8)	0.0006 (7)	−0.0075 (6)	0.0065 (7)
C5A	0.0404 (9)	0.0395 (9)	0.0384 (9)	0.0144 (7)	−0.0076 (7)	−0.0041 (7)
C6A	0.0255 (8)	0.0748 (13)	0.0385 (9)	0.0064 (8)	0.0012 (7)	−0.0071 (9)
C7A	0.0327 (8)	0.0526 (10)	0.0336 (8)	−0.0146 (7)	0.0054 (6)	0.0017 (7)
C8A	0.0390 (8)	0.0397 (9)	0.0260 (7)	−0.0015 (7)	0.0012 (6)	0.0052 (6)
C9A	0.0378 (8)	0.0347 (9)	0.0341 (8)	−0.0007 (7)	−0.0062 (7)	−0.0020 (7)
C10A	0.0323 (8)	0.0406 (9)	0.0327 (8)	−0.0097 (7)	−0.0010 (6)	−0.0010 (7)
C11A	0.0276 (7)	0.0550 (10)	0.0276 (7)	0.0022 (7)	−0.0036 (6)	0.0014 (7)
C12A	0.0319 (8)	0.0428 (9)	0.0265 (7)	−0.0026 (6)	−0.0028 (6)	0.0024 (6)
C13A	0.0452 (10)	0.0546 (12)	0.0297 (8)	−0.0030 (8)	0.0014 (7)	−0.0023 (8)
N1A	0.0250 (6)	0.0563 (9)	0.0260 (6)	0.0010 (6)	−0.0009 (5)	−0.0017 (6)
O1A	0.0376 (7)	0.0977 (12)	0.0352 (6)	0.0150 (7)	−0.0147 (5)	−0.0190 (7)
O2A	0.0310 (6)	0.1223 (14)	0.0451 (7)	0.0220 (7)	−0.0076 (5)	−0.0205 (8)
O3A	0.0290 (6)	0.0829 (10)	0.0298 (6)	0.0014 (6)	−0.0069 (4)	−0.0035 (6)
C1B	0.0245 (7)	0.0419 (9)	0.0268 (7)	0.0024 (6)	0.0003 (5)	−0.0016 (6)
C2B	0.0239 (7)	0.0467 (9)	0.0266 (7)	0.0037 (6)	0.0005 (5)	−0.0021 (6)
C3B	0.0250 (7)	0.0381 (8)	0.0250 (7)	−0.0001 (6)	−0.0001 (5)	0.0007 (6)
C4B	0.0362 (8)	0.0388 (9)	0.0341 (8)	−0.0062 (7)	0.0031 (6)	−0.0014 (7)
C5B	0.0348 (8)	0.0472 (10)	0.0348 (8)	−0.0121 (7)	0.0090 (6)	0.0004 (7)
C6B	0.0241 (7)	0.0621 (12)	0.0456 (10)	0.0033 (7)	0.0054 (7)	−0.0098 (8)
C7B	0.0342 (8)	0.0382 (9)	0.0416 (9)	0.0110 (7)	−0.0008 (7)	−0.0015 (7)
C8B	0.0351 (8)	0.0364 (9)	0.0368 (8)	−0.0032 (7)	0.0022 (6)	−0.0023 (7)
C9B	0.0408 (9)	0.0420 (9)	0.0269 (7)	0.0008 (7)	0.0045 (6)	0.0026 (7)
C10B	0.0356 (8)	0.0394 (9)	0.0344 (8)	0.0044 (7)	−0.0029 (7)	0.0053 (7)
C11B	0.0279 (8)	0.0611 (11)	0.0290 (7)	0.0029 (7)	0.0003 (6)	−0.0039 (7)
C12B	0.0375 (8)	0.0446 (9)	0.0289 (7)	−0.0064 (7)	−0.0017 (6)	0.0025 (7)
C13B	0.0600 (13)	0.0616 (14)	0.0370 (10)	−0.0063 (10)	0.0024 (9)	−0.0123 (9)
N1B	0.0295 (7)	0.0506 (9)	0.0275 (6)	0.0011 (6)	0.0014 (5)	−0.0038 (6)
O1B	0.0373 (7)	0.1177 (14)	0.0416 (7)	0.0126 (8)	−0.0100 (6)	−0.0319 (8)
O2B	0.0309 (7)	0.1649 (19)	0.0570 (9)	0.0271 (9)	−0.0086 (6)	−0.0440 (11)
O3B	0.0337 (6)	0.0701 (9)	0.0347 (6)	−0.0039 (6)	−0.0077 (5)	0.0022 (6)

Geometric parameters (Å, º)

C1A—C2A	1.529 (2)	C1B—C8B	1.534 (2)
C1A—C8A	1.542 (2)	C1B—C11B	1.519 (2)
C1A—C9A	1.536 (2)	C2B—C3B	1.5352 (19)
C1A—C11A	1.5198 (19)	C2B—C1B	1.536 (2)
C2A—H2A	1.01 (2)	C2B—H2C	1.008 (19)
C2A—H2B	0.984 (19)	C2B—H2D	1.00 (2)
C3A—C2A	1.5359 (18)	C3B—C4B	1.534 (2)
C3A—C4A	1.532 (2)	C3B—C10B	1.534 (2)
C3A—C10A	1.531 (2)	C4B—H4C	1.013 (18)
C3A—N1A	1.4699 (19)	C4B—H4D	0.97 (2)
C4A—C5A	1.535 (2)	C5B—C6B	1.524 (3)
C4A—H4B	0.982 (18)	C5B—C4B	1.531 (2)
C4A—H4A	0.966 (19)	C5B—H5B	0.974 (19)
C5A—C6A	1.525 (3)	C6B—C7B	1.524 (3)
C5A—H5A	0.95 (2)	C6B—H6C	0.99 (2)
C6A—H6B	1.02 (2)	C6B—H6D	1.05 (2)
C6A—H6A	1.03 (2)	C7B—H7B	0.97 (2)
C7A—C6A	1.521 (3)	C8B—C7B	1.531 (2)
C7A—C10A	1.529 (2)	C8B—H8C	1.024 (18)
C7A—H7A	0.96 (2)	C8B—H8D	0.98 (2)
C8A—C7A	1.529 (2)	C9B—C5B	1.530 (2)
C8A—H8B	1.03 (2)	C9B—C1B	1.546 (2)
C8A—H8A	1.00 (2)	C9B—H9D	1.001 (19)
C9A—C5A	1.531 (2)	C9B—H9C	1.03 (2)
C9A—H9A	0.996 (19)	C10B—C7B	1.534 (2)
C9A—H9B	0.976 (19)	C10B—H10D	0.981 (19)
C10A—H10A	0.976 (19)	C10B—H10C	1.008 (19)
C10A—H10B	1.01 (2)	C11B—O2B	1.194 (2)
C12A—C13A	1.496 (2)	C13B—C12B	1.500 (3)
C13A—H13B	1.00 (2)	C13B—H13D	0.97 (2)
C13A—H13A	0.94 (2)	C13B—H13F	0.98 (3)
C13A—H13C	0.98 (3)	C13B—H13E	0.98 (3)
N1A—C12A	1.3348 (19)	N1B—C12B	1.3393 (19)
N1A—H1C	0.85 (2)	N1B—C3B	1.4720 (19)
O1A—C11A	1.309 (2)	N1B—H1D	0.85 (2)
O1A—H1A	0.95 (3)	O1B—C11B	1.305 (2)
O2A—C11A	1.203 (2)	O1B—H1B	0.92 (3)
O3A—C12A	1.2378 (19)	O3B—C12B	1.236 (2)
C1A—C9A—H9A	110.5 (11)	C3B—C4B—H4D	107.4 (11)
C1A—C8A—H8B	107.3 (11)	C4B—C3B—C10B	109.79 (13)
C1A—C2A—C3A	110.45 (12)	C4B—C3B—C2B	109.40 (13)
C1A—C9A—H9B	108.0 (11)	C4B—C5B—H5B	110.4 (11)
C1A—C2A—H2B	112.2 (11)	C5B—C4B—C3B	109.58 (13)
C1A—C2A—H2A	110.9 (11)	C5B—C4B—H4C	109.3 (10)
C1A—C8A—H8A	110.2 (11)	C5B—C6B—C7B	109.22 (13)
C2A—C1A—C9A	109.31 (13)	C5B—C6B—H6C	109.7 (13)
C2A—C1A—C8A	108.90 (13)	C5B—C9B—C1B	109.32 (13)
C3A—C2A—H2B	108.5 (11)	C5B—C9B—H9D	109.9 (10)
C3A—C2A—H2A	107.9 (11)	C5B—C9B—H9C	110.3 (11)
C3A—N1A—H1C	117.4 (13)	C5B—C6B—H6D	111.6 (11)
C3A—C4A—C5A	109.41 (13)	C6B—C5B—C9B	110.22 (14)
C3A—C10A—H10A	109.5 (11)	C6B—C5B—C4B	109.58 (15)
C3A—C10A—H10B	108.9 (11)	C6B—C5B—H5B	108.6 (11)
C3A—C4A—H4B	109.2 (11)	C6B—C7B—C8B	108.62 (14)
C3A—C4A—H4A	106.8 (11)	C6B—C7B—C10B	110.41 (15)
C4A—C3A—C2A	109.22 (12)	C6B—C7B—H7B	107.9 (12)
C4A—C5A—H5A	111.1 (12)	C6B—C7B—C8B	108.62 (14)
C5A—C4A—H4A	112.4 (11)	C6B—C7B—C10B	110.41 (15)
C5A—C9A—C1A	109.56 (13)	C6B—C7B—H7B	107.9 (12)
C5A—C9A—H9A	109.3 (10)	C7B—C10B—C3B	109.08 (13)
C5A—C9A—H9B	111.3 (10)	C7B—C10B—H10D	108.5 (11)
C5A—C4A—H4B	110.2 (10)	C7B—C10B—H10C	111.3 (11)
C6A—C7A—C10A	110.17 (15)	C7B—C8B—C1B	109.48 (13)
C6A—C7A—C8A	109.79 (14)	C7B—C8B—H8C	109.4 (10)
C6A—C7A—H7A	109.7 (11)	C7B—C8B—H8D	110.4 (12)
C6A—C5A—C9A	108.71 (14)	C7B—C6B—H6C	108.9 (13)
C6A—C5A—C4A	109.63 (15)	C7B—C6B—H6D	109.6 (11)
C6A—C5A—H5A	107.9 (12)	C8B—C7B—C10B	110.54 (14)
C7A—C8A—C1A	109.27 (12)	C8B—C7B—H7B	109.9 (12)
C7A—C8A—H8B	111.4 (11)	C8B—C1B—C2B	109.77 (13)
C7A—C8A—H8A	110.0 (11)	C8B—C1B—C9B	108.43 (13)
C7A—C10A—C3A	109.61 (13)	C8B—C7B—C10B	110.54 (14)
C7A—C10A—H10A	108.9 (11)	C8B—C7B—H7B	109.9 (12)
C7A—C10A—H10B	111.2 (11)	C9B—C5B—C4B	109.42 (14)
C8A—C7A—H7A	108.9 (11)	C9B—C5B—H5B	108.6 (11)
C9A—C5A—C4A	110.42 (14)	C10B—C3B—C2B	108.32 (13)
C9A—C5A—H5A	109.1 (12)	C10B—C7B—H7B	109.4 (12)
C9A—C1A—C8A	109.01 (13)	C10B—C7B—H7B	109.4 (12)
C10A—C7A—C8A	109.25 (14)	C11B—C1B—C8B	110.27 (13)
C10A—C7A—H7A	109.0 (12)	C11B—C1B—C2B	110.41 (12)
C10A—C3A—C4A	109.08 (13)	C11B—C1B—C9B	109.23 (13)
C10A—C3A—C2A	109.12 (12)	C12B—C13B—H13D	112.7 (14)
C11A—O1A—H1A	111.8 (17)	C12B—C13B—H13F	110.8 (15)
C11A—C1A—C2A	110.68 (12)	C12B—C13B—H13E	107.2 (16)
C11A—C1A—C9A	111.29 (13)	C12B—N1B—C3B	126.43 (14)
C11A—C1A—C8A	107.58 (12)	C12B—N1B—H1D	116.1 (13)
C12A—C13A—H13C	109.2 (16)	C11B—O1B—H1B	111.7 (17)
C12A—N1A—C3A	126.49 (13)	N1B—C3B—C4B	110.17 (13)
C12A—N1A—H1C	116.1 (13)	N1B—C3B—C10B	112.22 (12)
C12A—C13A—H13B	112.5 (13)	N1B—C3B—C2B	106.84 (12)
C12A—C13A—H13A	110.6 (14)	N1B—C12B—C13B	116.02 (16)
N1A—C3A—C10A	111.00 (13)	O1B—C11B—C1B	113.36 (14)
N1A—C3A—C4A	112.03 (12)	O2B—C11B—O1B	122.34 (15)
N1A—C3A—C2A	106.31 (12)	O2B—C11B—C1B	124.30 (15)
N1A—C12A—C13A	116.28 (15)	O3B—C12B—N1B	122.58 (16)
O1A—C11A—C1A	112.35 (14)	O3B—C12B—C13B	121.35 (15)
O2A—C11A—O1A	123.52 (14)	H2C—C2B—H2D	107.1 (15)
O2A—C11A—C1A	124.09 (15)	H2B—C2A—H2A	106.6 (15)
O3A—C12A—N1A	121.84 (15)	H4B—C4A—H4A	108.8 (15)
O3A—C12A—C13A	121.86 (14)	H4C—C4B—H4D	108.2 (15)
C1B—C2B—H2C	110.4 (11)	H6C—C6B—H6D	107.8 (16)
C1B—C2B—H2D	110.3 (11)	H6B—C6A—H6A	108.6 (16)
C1B—C9B—H9D	109.2 (11)	H8B—C8A—H8A	108.7 (15)
C1B—C9B—H9C	109.5 (11)	H8C—C8B—H8D	108.4 (15)
C1B—C8B—H8C	110.3 (10)	H9A—C9A—H9B	108.2 (15)
C1B—C8B—H8D	108.9 (12)	H9D—C9B—H9C	108.6 (16)
C2B—C1B—C9B	108.68 (13)	H10A—C10A—H10B	108.7 (15)
C3B—C2B—C1B	110.52 (12)	H10D—C10B—H10C	110.3 (15)
C3B—C2B—H2C	109.5 (11)	H13A—C13A—H13C	109 (2)
C3B—C2B—H2D	109.0 (11)	H13B—C13A—H13A	110.7 (19)
C3B—N1B—H1D	117.4 (13)	H13B—C13A—H13C	105 (2)
C3B—C10B—H10D	110.2 (11)	H13D—C13B—H13E	109 (2)
C3B—C10B—H10C	107.3 (11)	H13D—C13B—H13F	110 (2)
C3B—C4B—H4C	110.8 (10)	H13F—C13B—H13E	107 (2)
C5B—C4B—H4D	111.6 (11)
C13A—C12A—N1A—C3A	−174.35 (16)	C13B—C12B—N1B—C3B	171.35 (16)
O3A—C12A—N1A—C3A	3.9 (3)	O3B—C12B—N1B—C3B	−6.2 (3)
C2A—C1A—C11A—O1A	164.46 (15)	C2B—C1B—C11B—O1B	−168.34 (15)
C2A—C1A—C11A—O2A	−17.9 (2)	C2B—C1B—C11B—O2B	12.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O3A^i	0.95 (3)	1.61 (3)	2.534 (2)	163 (3)
O1B—H1B···O3B^ii	0.92 (4)	1.73 (3)	2.618 (2)	163 (3)
N1A—H1C···O2B^iii	0.85 (2)	2.17 (2)	2.976 (2)	158 (2)
N1B—H1D···O2A^iv	0.85 (2)	2.22 (2)	3.006 (2)	154 (2)

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1/2, −y+3/2, z−1/2; (iv) x−1/2, −y+3/2, z+1/2.