2-(L-Alanylamino)-L-butyric acid

The title dipeptide, C₇H₁₄N₂O₃, with the common name L-alanyl-L-2-amino­butyric acid, has previously been crystallized as the 0.33-hydrate [Görbitz (2002). Acta Cryst. C58, o533-o536]. By using 1,1,1,3,3,3-hexa­fluoro­propan-2-ol as the solvent, water-free crystals were obtained. The two crystal structures are related (P2₁, Z' = 3 for both), but the mol­ecular conformations and details of the hydrogen-bonding network are different.

Key indicators

• Single-crystal X-ray study
• T = 105 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.066
• wR factor = 0.145
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.90 mm

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.776     0.998
            Tmin(prime) and Tmax expected:      0.916     0.999
            RR(prime) =      0.847
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

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           25.02
           From the CIF: _reflns_number_total               2752
           Count of symmetry unique reflns         2754
           Completeness (_total/calc)             99.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   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

   0 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
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

2-(L-alanylamino)-L-butyric acid

Crystal data

C7H14N2O3	F(000) = 564
Mr = 174.20	Dx = 1.244 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1396 reflections
a = 15.665 (5) Å	θ = 1.3–25.0°
b = 5.470 (2) Å	µ = 0.10 mm^−1
c = 17.147 (7) Å	T = 105 K
β = 108.233 (9)°	Needle, colourless
V = 1395.6 (9) Å^3	0.90 × 0.03 × 0.02 mm
Z = 6

Data collection

Siemens SMART CCD area-detector diffractometer	2752 independent reflections
Radiation source: fine-focus sealed tube	1596 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
Detector resolution: 8.3 pixels mm^-1	θmax = 25.0°, θmin = 1.3°
ω rotation scans	h = −18→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→6
Tmin = 0.776, Tmax = 0.999	l = −15→20
7493 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0533P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2752 reflections	Δρmax = 0.35 e Å^−3
340 parameters	Δρmin = −0.33 e Å^−3
325 restraints	Extinction correction: SHELXTL (Bruker, 2000), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.090 (6)

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.

Refinement. Data were collected by measuring three sets of exposures with the detector set at 2θ = 29°, crystal-to-detector distance 5.00 cm. Refinement of F² against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	−0.0020 (3)	0.6363 (8)	0.8838 (2)	0.0195 (11)
O2A	0.0093 (3)	0.6796 (9)	0.6167 (2)	0.0312 (12)
O3A	0.0296 (3)	1.0377 (8)	0.6796 (3)	0.0303 (13)
N1A	−0.0473 (3)	0.2058 (10)	0.9352 (3)	0.0196 (14)
H1A	0.0061	0.2217	0.9758	0.029*
H2A	−0.0738	0.0625	0.9417	0.029*
H3A	−0.0840	0.3327	0.9377	0.029*
N2A	0.0373 (3)	0.4732 (9)	0.7777 (3)	0.0261 (15)
H4A	0.0315	0.3457	0.7451	0.031*
C1A	−0.0315 (4)	0.2068 (10)	0.8542 (3)	0.0175 (16)
H11A	0.0169	0.0856	0.8561	0.021*
C2A	−0.1164 (4)	0.1276 (14)	0.7881 (3)	0.0288 (18)
H21A	−0.1064	0.1315	0.7345	0.043*
H22A	−0.1656	0.2390	0.7875	0.043*
H23A	−0.1322	−0.0390	0.7996	0.043*
C3A	0.0019 (4)	0.4603 (10)	0.8403 (3)	0.0191 (16)
C4A	0.0843 (3)	0.6873 (11)	0.7618 (3)	0.0173 (15)	0.63 (2)
H41A	0.0857	0.8091	0.8056	0.021*	0.63 (2)
C5A	0.1828 (5)	0.634 (3)	0.7680 (6)	0.031 (3)	0.63 (2)
H51A	0.1841	0.4954	0.7312	0.038*	0.63 (2)
H52A	0.2079	0.7785	0.7482	0.038*	0.63 (2)
C6A	0.2425 (6)	0.572 (3)	0.8544 (8)	0.041 (3)	0.63 (2)
H61A	0.2971	0.4906	0.8516	0.061*	0.63 (2)
H62A	0.2100	0.4632	0.8807	0.061*	0.63 (2)
H63A	0.2587	0.7228	0.8865	0.061*	0.63 (2)
C7A	0.0358 (4)	0.8090 (10)	0.6800 (3)	0.0152 (15)
C41A	0.0843 (3)	0.6873 (11)	0.7618 (3)	0.0173 (15)	0.37 (2)
H42A	0.0986	0.8062	0.8084	0.021*	0.37 (2)
C51A	0.1695 (12)	0.564 (5)	0.7534 (11)	0.031 (3)	0.37 (2)
H53A	0.1513	0.4363	0.7104	0.038*	0.37 (2)
H54A	0.2052	0.6873	0.7351	0.038*	0.37 (2)
C61A	0.2286 (12)	0.447 (6)	0.8325 (14)	0.041 (3)	0.37 (2)
H64A	0.2910	0.4428	0.8321	0.061*	0.37 (2)
H65A	0.2078	0.2801	0.8368	0.061*	0.37 (2)
H66A	0.2250	0.5434	0.8796	0.061*	0.37 (2)
O1B	0.1446 (3)	1.1508 (9)	0.5468 (3)	0.0264 (12)
O2B	0.4259 (3)	1.1649 (9)	0.5593 (2)	0.0220 (11)
O3B	0.3857 (3)	1.5252 (8)	0.5968 (3)	0.0252 (12)
N1B	0.0523 (3)	0.7634 (10)	0.4725 (3)	0.0176 (13)
H1B	0.0244	0.7495	0.5116	0.026*
H2B	0.0305	0.6480	0.4331	0.026*
H3B	0.0419	0.9147	0.4495	0.026*
N2B	0.2778 (3)	0.9571 (9)	0.5971 (3)	0.0209 (13)
H4B	0.3068	0.8184	0.5988	0.025*
C1B	0.1507 (3)	0.7274 (11)	0.5109 (3)	0.0171 (16)
H11B	0.1608	0.5949	0.5530	0.021*
C2B	0.1908 (4)	0.6481 (15)	0.4447 (4)	0.0271 (18)
H21B	0.1622	0.4957	0.4195	0.041*
H22B	0.2556	0.6219	0.4693	0.041*
H23B	0.1803	0.7757	0.4026	0.041*
C3B	0.1902 (4)	0.9662 (11)	0.5537 (3)	0.0172 (16)
C4B	0.3274 (3)	1.1683 (11)	0.6418 (3)	0.0177 (15)
H41B	0.2826	1.2888	0.6494	0.021*
C5B	0.3875 (4)	1.0889 (12)	0.7273 (3)	0.0234 (18)
H51B	0.3495	1.0127	0.7570	0.028*
H52B	0.4302	0.9631	0.7207	0.028*
C6B	0.4403 (5)	1.2966 (15)	0.7787 (4)	0.042 (2)
H61B	0.4604	1.2487	0.8366	0.063*
H62B	0.4019	1.4417	0.7715	0.063*
H63B	0.4927	1.3336	0.7611	0.063*
C7B	0.3830 (4)	1.2951 (10)	0.5945 (3)	0.0166 (16)
O1C	0.6181 (3)	1.0390 (9)	0.7192 (3)	0.0301 (13)
O2C	0.8002 (3)	0.4751 (8)	0.9087 (3)	0.0278 (12)
O3C	0.8635 (3)	0.8086 (8)	0.9788 (3)	0.0225 (12)
N1C	0.5378 (3)	0.7511 (10)	0.5893 (3)	0.0197 (14)
H1C	0.4849	0.6728	0.5832	0.030*
H2C	0.5527	0.7359	0.5423	0.030*
H3C	0.5319	0.9122	0.5998	0.030*
N2C	0.6704 (3)	0.7155 (10)	0.8036 (3)	0.0251 (15)
H4C	0.6661	0.5558	0.8073	0.030*
C1C	0.6094 (4)	0.6409 (12)	0.6586 (3)	0.0215 (16)
H11C	0.5875	0.4836	0.6752	0.026*
C2C	0.6928 (4)	0.5933 (17)	0.6332 (4)	0.048 (3)
H21C	0.7326	0.4798	0.6722	0.072*
H22C	0.7245	0.7477	0.6331	0.072*
H23C	0.6750	0.5218	0.5781	0.072*
C3C	0.6317 (4)	0.8211 (12)	0.7308 (3)	0.0223 (17)
C4C	0.7197 (4)	0.8524 (11)	0.8780 (3)	0.0264 (19)
H41C	0.7418	1.0088	0.8609	0.032*
C5C	0.6596 (5)	0.9139 (15)	0.9305 (4)	0.044 (2)
H51C	0.6936	1.0196	0.9767	0.053*
H52C	0.6071	1.0085	0.8968	0.053*
C6C	0.6260 (5)	0.6915 (18)	0.9651 (5)	0.058 (3)
H61C	0.5877	0.7444	0.9976	0.087*
H62C	0.6774	0.5995	1.0003	0.087*
H63C	0.5912	0.5870	0.9199	0.087*
C7C	0.8013 (4)	0.6999 (11)	0.9260 (3)	0.0229 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.030 (3)	0.010 (3)	0.019 (2)	0.005 (2)	0.010 (2)	0.001 (2)
O2A	0.051 (3)	0.020 (3)	0.022 (3)	−0.013 (3)	0.012 (2)	−0.008 (3)
O3A	0.050 (3)	0.017 (3)	0.027 (3)	0.003 (2)	0.016 (2)	0.002 (2)
N1A	0.025 (3)	0.015 (3)	0.018 (3)	−0.005 (3)	0.005 (2)	0.005 (3)
N2A	0.046 (3)	0.015 (3)	0.021 (3)	−0.001 (3)	0.016 (3)	−0.003 (3)
C1A	0.026 (4)	0.011 (4)	0.017 (3)	0.002 (3)	0.009 (3)	0.000 (3)
C2A	0.038 (4)	0.026 (4)	0.020 (3)	−0.002 (4)	0.006 (3)	0.000 (3)
C3A	0.023 (4)	0.014 (4)	0.019 (3)	0.004 (3)	0.005 (3)	0.003 (3)
C4A	0.020 (3)	0.016 (3)	0.016 (3)	−0.002 (3)	0.004 (3)	0.000 (3)
C5A	0.026 (4)	0.039 (6)	0.031 (4)	0.003 (4)	0.011 (4)	0.009 (4)
C6A	0.032 (5)	0.043 (6)	0.042 (5)	0.005 (5)	0.004 (4)	0.005 (5)
C7A	0.019 (3)	0.009 (3)	0.018 (3)	−0.002 (3)	0.006 (2)	−0.001 (3)
C41A	0.020 (3)	0.016 (3)	0.016 (3)	−0.002 (3)	0.004 (3)	0.000 (3)
C51A	0.026 (4)	0.039 (6)	0.031 (4)	0.003 (4)	0.011 (4)	0.009 (4)
C61A	0.032 (5)	0.043 (6)	0.042 (5)	0.005 (5)	0.004 (4)	0.005 (5)
O1B	0.024 (2)	0.010 (3)	0.039 (3)	0.002 (2)	0.001 (2)	0.001 (2)
O2B	0.029 (3)	0.016 (2)	0.022 (2)	0.004 (2)	0.010 (2)	0.000 (2)
O3B	0.019 (2)	0.017 (3)	0.038 (3)	−0.001 (2)	0.007 (2)	−0.005 (2)
N1B	0.024 (3)	0.011 (3)	0.016 (3)	−0.002 (2)	0.004 (2)	−0.003 (2)
N2B	0.021 (3)	0.010 (3)	0.031 (3)	−0.001 (3)	0.007 (3)	−0.006 (3)
C1B	0.019 (3)	0.010 (4)	0.021 (3)	0.005 (3)	0.005 (3)	−0.002 (3)
C2B	0.024 (4)	0.029 (4)	0.029 (4)	0.001 (3)	0.009 (3)	−0.014 (3)
C3B	0.019 (4)	0.017 (4)	0.016 (3)	0.002 (3)	0.006 (3)	0.004 (3)
C4B	0.015 (3)	0.011 (3)	0.029 (3)	0.001 (3)	0.008 (3)	−0.004 (3)
C5B	0.025 (4)	0.021 (4)	0.023 (4)	−0.002 (3)	0.006 (3)	0.002 (3)
C6B	0.037 (4)	0.046 (5)	0.041 (4)	−0.003 (4)	0.009 (4)	−0.010 (4)
C7B	0.018 (3)	0.011 (3)	0.018 (3)	0.002 (3)	0.001 (2)	0.002 (3)
O1C	0.033 (3)	0.020 (3)	0.032 (3)	0.006 (2)	0.002 (2)	0.001 (2)
O2C	0.026 (3)	0.018 (3)	0.033 (3)	0.000 (2)	0.002 (2)	0.001 (2)
O3C	0.025 (3)	0.018 (3)	0.023 (2)	−0.008 (2)	0.005 (2)	−0.003 (2)
N1C	0.021 (3)	0.016 (3)	0.022 (3)	−0.001 (3)	0.006 (2)	−0.002 (2)
N2C	0.025 (3)	0.022 (3)	0.024 (3)	−0.001 (3)	0.002 (2)	−0.002 (3)
C1C	0.026 (4)	0.020 (4)	0.015 (3)	0.009 (3)	0.002 (3)	0.010 (3)
C2C	0.041 (4)	0.069 (6)	0.033 (4)	0.036 (4)	0.010 (4)	0.004 (4)
C3C	0.023 (4)	0.017 (4)	0.026 (4)	0.005 (3)	0.005 (3)	0.005 (3)
C4C	0.028 (4)	0.022 (4)	0.024 (4)	−0.002 (3)	0.000 (3)	−0.004 (3)
C5C	0.038 (4)	0.046 (5)	0.043 (4)	0.016 (4)	0.007 (4)	−0.010 (4)
C6C	0.053 (5)	0.081 (6)	0.051 (5)	−0.009 (5)	0.032 (4)	−0.015 (5)
C7C	0.025 (4)	0.022 (4)	0.023 (3)	−0.004 (3)	0.009 (3)	0.001 (3)

Geometric parameters (Å, º)

O1A—C3A	1.232 (6)	C1B—C2B	1.523 (6)
O2A—C7A	1.254 (6)	C1B—C3B	1.531 (7)
O3A—C7A	1.255 (6)	C1B—H11B	1.0000
N1A—C1A	1.486 (6)	C2B—H21B	0.9800
N1A—H1A	0.9100	C2B—H22B	0.9800
N1A—H2A	0.9100	C2B—H23B	0.9800
N1A—H3A	0.9100	C4B—C5B	1.536 (7)
N2A—C3A	1.354 (6)	C4B—C7B	1.530 (6)
N2A—C4A	1.454 (6)	C4B—H41B	1.0000
N2A—H4A	0.8800	C5B—C6B	1.515 (7)
C1A—C2A	1.516 (7)	C5B—H51B	0.9900
C1A—C3A	1.527 (7)	C5B—H52B	0.9900
C1A—H11A	1.0000	C6B—H61B	0.9800
C2A—H21A	0.9800	C6B—H62B	0.9800
C2A—H22A	0.9800	C6B—H63B	0.9800
C2A—H23A	0.9800	O1C—C3C	1.216 (6)
C4A—C7A	1.522 (6)	O2C—C7C	1.263 (7)
C4A—C5A	1.541 (7)	O3C—C7C	1.254 (6)
C4A—H41A	1.0000	N1C—C1C	1.484 (6)
C5A—C6A	1.522 (8)	N1C—H1C	0.9100
C5A—H51A	0.9900	N1C—H2C	0.9100
C5A—H52A	0.9900	N1C—H3C	0.9100
C6A—H61A	0.9800	N2C—C3C	1.337 (6)
C6A—H62A	0.9800	N2C—C4C	1.472 (6)
C6A—H63A	0.9800	N2C—H4C	0.8800
C51A—C61A	1.522 (8)	C1C—C3C	1.534 (7)
C51A—H53A	0.9900	C1C—C2C	1.524 (7)
C51A—H54A	0.9900	C1C—H11C	1.0000
C61A—H64A	0.9800	C2C—H21C	0.9800
C61A—H65A	0.9800	C2C—H22C	0.9800
C61A—H66A	0.9800	C2C—H23C	0.9800
O1B—C3B	1.222 (6)	C4C—C5C	1.531 (7)
O2B—C7B	1.256 (6)	C4C—C7C	1.532 (7)
O3B—C7B	1.260 (6)	C4C—H41C	1.0000
N1B—C1B	1.487 (6)	C5C—C6C	1.518 (8)
N1B—H1B	0.9100	C5C—H51C	0.9900
N1B—H2B	0.9100	C5C—H52C	0.9900
N1B—H3B	0.9100	C6C—H61C	0.9800
N2B—C3B	1.342 (6)	C6C—H62C	0.9800
N2B—C4B	1.468 (6)	C6C—H63C	0.9800
N2B—H4B	0.8800
C1A—N1A—H1A	109.5	C1B—C2B—H23B	109.5
C1A—N1A—H2A	109.5	H21B—C2B—H23B	109.5
H1A—N1A—H2A	109.5	H22B—C2B—H23B	109.5
C1A—N1A—H3A	109.5	O1B—C3B—N2B	123.4 (5)
H1A—N1A—H3A	109.5	O1B—C3B—C1B	121.5 (5)
H2A—N1A—H3A	109.5	N2B—C3B—C1B	115.1 (5)
C3A—N2A—C4A	123.2 (5)	N2B—C4B—C5B	110.0 (4)
C3A—N2A—H4A	118.4	N2B—C4B—C7B	112.1 (4)
C4A—N2A—H4A	118.4	C5B—C4B—C7B	110.7 (4)
N1A—C1A—C2A	109.5 (4)	N2B—C4B—H41B	108.0
N1A—C1A—C3A	108.4 (4)	C5B—C4B—H41B	108.0
C2A—C1A—C3A	114.0 (5)	C7B—C4B—H41B	108.0
N1A—C1A—H11A	108.3	C6B—C5B—C4B	113.7 (5)
C2A—C1A—H11A	108.3	C6B—C5B—H51B	108.8
C3A—C1A—H11A	108.3	C4B—C5B—H51B	108.8
C1A—C2A—H21A	109.5	C6B—C5B—H52B	108.8
C1A—C2A—H22A	109.5	C4B—C5B—H52B	108.8
H21A—C2A—H22A	109.5	H51B—C5B—H52B	107.7
C1A—C2A—H23A	109.5	C5B—C6B—H61B	109.5
H21A—C2A—H23A	109.5	C5B—C6B—H62B	109.5
H22A—C2A—H23A	109.5	H61B—C6B—H62B	109.5
O1A—C3A—N2A	123.3 (5)	C5B—C6B—H63B	109.5
O1A—C3A—C1A	122.1 (4)	H61B—C6B—H63B	109.5
N2A—C3A—C1A	114.6 (5)	H62B—C6B—H63B	109.5
N2A—C4A—C7A	112.9 (4)	O2B—C7B—O3B	124.3 (5)
N2A—C4A—C5A	112.9 (7)	O2B—C7B—C4B	118.5 (5)
C7A—C4A—C5A	110.3 (5)	O3B—C7B—C4B	117.1 (5)
N2A—C4A—H41A	106.8	C1C—N1C—H1C	109.5
C7A—C4A—H41A	106.8	C1C—N1C—H2C	109.5
C5A—C4A—H41A	106.8	H1C—N1C—H2C	109.5
C6A—C5A—C4A	114.0 (5)	C1C—N1C—H3C	109.5
C6A—C5A—H51A	108.8	H1C—N1C—H3C	109.5
C4A—C5A—H51A	108.8	H2C—N1C—H3C	109.5
C6A—C5A—H52A	108.8	C3C—N2C—C4C	123.5 (5)
C4A—C5A—H52A	108.8	C3C—N2C—H4C	118.3
H51A—C5A—H52A	107.6	C4C—N2C—H4C	118.3
C5A—C6A—H61A	109.5	N1C—C1C—C3C	108.0 (4)
C5A—C6A—H62A	109.5	N1C—C1C—C2C	110.0 (4)
H61A—C6A—H62A	109.5	C3C—C1C—C2C	109.9 (5)
C5A—C6A—H63A	109.5	N1C—C1C—H11C	109.6
H61A—C6A—H63A	109.5	C3C—C1C—H11C	109.6
H62A—C6A—H63A	109.5	C2C—C1C—H11C	109.6
O3A—C7A—O2A	123.7 (5)	C1C—C2C—H21C	109.5
O3A—C7A—C4A	117.2 (5)	C1C—C2C—H22C	109.5
O2A—C7A—C4A	119.0 (5)	H21C—C2C—H22C	109.5
C61A—C51A—H53A	108.8	C1C—C2C—H23C	109.5
C61A—C51A—H54A	108.8	H21C—C2C—H23C	109.5
H53A—C51A—H54A	107.7	H22C—C2C—H23C	109.5
C51A—C61A—H64A	109.5	O1C—C3C—N2C	125.5 (5)
C51A—C61A—H65A	109.5	O1C—C3C—C1C	120.9 (5)
H64A—C61A—H65A	109.5	N2C—C3C—C1C	113.5 (5)
C51A—C61A—H66A	109.5	N2C—C4C—C5C	111.6 (5)
H64A—C61A—H66A	109.5	N2C—C4C—C7C	108.2 (5)
H65A—C61A—H66A	109.5	C5C—C4C—C7C	111.5 (5)
C1B—N1B—H1B	109.5	N2C—C4C—H41C	108.5
C1B—N1B—H2B	109.5	C5C—C4C—H41C	108.5
H1B—N1B—H2B	109.5	C7C—C4C—H41C	108.5
C1B—N1B—H3B	109.5	C6C—C5C—C4C	114.0 (6)
H1B—N1B—H3B	109.5	C6C—C5C—H51C	108.8
H2B—N1B—H3B	109.5	C4C—C5C—H51C	108.8
C3B—N2B—C4B	122.9 (5)	C6C—C5C—H52C	108.8
C3B—N2B—H4B	118.6	C4C—C5C—H52C	108.8
C4B—N2B—H4B	118.6	H51C—C5C—H52C	107.7
N1B—C1B—C2B	108.6 (4)	C5C—C6C—H61C	109.5
N1B—C1B—C3B	107.9 (4)	C5C—C6C—H62C	109.5
C2B—C1B—C3B	113.6 (5)	H61C—C6C—H62C	109.5
N1B—C1B—H11B	108.9	C5C—C6C—H63C	109.5
C2B—C1B—H11B	108.9	H61C—C6C—H63C	109.5
C3B—C1B—H11B	108.9	H62C—C6C—H63C	109.5
C1B—C2B—H21B	109.5	O3C—C7C—O2C	125.5 (5)
C1B—C2B—H22B	109.5	O3C—C7C—C4C	117.3 (5)
H21B—C2B—H22B	109.5	O2C—C7C—C4C	117.2 (5)
N1A—C1A—C3A—N2A	166.5 (5)	C2B—C1B—C3B—O1B	114.1 (7)
C1A—C3A—N2A—C4A	−170.9 (5)	C2B—C1B—C3B—N2B	−64.6 (7)
C3A—N2A—C4A—C7A	−115.3 (6)	C3B—N2B—C4B—C5B	136.2 (6)
N2A—C4A—C7A—O2A	−48.7 (7)	C7B—C4B—C5B—C6B	56.6 (7)
N2A—C4A—C5A—C6A	−67.1 (12)	C5B—C4B—C7B—O2B	80.8 (6)
C4A—N2A—C3A—O1A	7.9 (9)	N2B—C4B—C7B—O3B	140.8 (6)
N1A—C1A—C3A—O1A	−12.3 (8)	C5B—C4B—C7B—O3B	−96.0 (7)
C2A—C1A—C3A—O1A	109.8 (7)	N1C—C1C—C3C—N2C	158.0 (5)
C2A—C1A—C3A—N2A	−71.4 (7)	C1C—C3C—N2C—C4C	162.8 (5)
C3A—N2A—C4A—C5A	118.8 (7)	C3C—N2C—C4C—C7C	−141.8 (6)
C7A—C4A—C5A—C6A	165.5 (9)	N2C—C4C—C7C—O2C	−17.8 (7)
N2A—C4A—C7A—O3A	135.4 (6)	N2C—C4C—C5C—C6C	64.1 (7)
C5A—C4A—C7A—O3A	−97.3 (9)	C4C—N2C—C3C—O1C	−13.8 (11)
C5A—C4A—C7A—O2A	78.6 (9)	N1C—C1C—C3C—O1C	−25.2 (8)
N1B—C1B—C3B—N2B	174.9 (5)	C2C—C1C—C3C—O1C	94.8 (8)
C1B—C3B—N2B—C4B	179.6 (5)	C2C—C1C—C3C—N2C	−82.0 (7)
C3B—N2B—C4B—C7B	−100.2 (6)	C3C—N2C—C4C—C5C	95.2 (7)
N2B—C4B—C7B—O2B	−42.4 (7)	C7C—C4C—C5C—C6C	−57.0 (8)
N2B—C4B—C5B—C6B	−179.0 (5)	N2C—C4C—C7C—O3C	161.9 (5)
C4B—N2B—C3B—O1B	1.0 (9)	C5C—C4C—C7C—O3C	−75.0 (7)
N1B—C1B—C3B—O1B	−6.4 (8)	C5C—C4C—C7C—O2C	105.3 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O3C^i	0.91	2.00	2.850 (6)	154
N1A—H2A···O3C^ii	0.91	1.92	2.808 (7)	164
N1A—H3A···O2C^iii	0.91	1.89	2.720 (7)	150
N2A—H4A···O3A^iv	0.88	2.02	2.897 (7)	174
C1A—H11A···O1A^iv	1.00	2.54	3.172 (7)	121
N1B—H1B···O2A	0.91	1.93	2.796 (7)	158
N1B—H2B···O3A^v	0.91	1.96	2.808 (6)	154
N1B—H3B···O2A^vi	0.91	1.86	2.744 (7)	163
N2B—H4B···O3B^iv	0.88	2.03	2.906 (7)	172
C1B—H11B···O1B^iv	1.00	2.44	3.220 (7)	134
N1C—H1C···O3B^iv	0.91	1.83	2.722 (7)	167
N1C—H2C···O2B^vii	0.91	1.91	2.818 (6)	172
N1C—H3C···O2B	0.91	2.10	2.811 (7)	134
N2C—H4C···O2C	0.88	2.31	2.612 (6)	100
C1C—H11C···O1C^iv	1.00	2.55	3.442 (8)	149

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