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.
Supporting information
CCDC reference: 289809
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.90 × 0.03 × 0.02 mm |
Z = 6 | |
Data collection top
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 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)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0533P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.090 (6) |
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. 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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O3Ci | 0.91 | 2.00 | 2.850 (6) | 154 |
N1A—H2A···O3Cii | 0.91 | 1.92 | 2.808 (7) | 164 |
N1A—H3A···O2Ciii | 0.91 | 1.89 | 2.720 (7) | 150 |
N2A—H4A···O3Aiv | 0.88 | 2.02 | 2.897 (7) | 174 |
C1A—H11A···O1Aiv | 1.00 | 2.54 | 3.172 (7) | 121 |
N1B—H1B···O2A | 0.91 | 1.93 | 2.796 (7) | 158 |
N1B—H2B···O3Av | 0.91 | 1.96 | 2.808 (6) | 154 |
N1B—H3B···O2Avi | 0.91 | 1.86 | 2.744 (7) | 163 |
N2B—H4B···O3Biv | 0.88 | 2.03 | 2.906 (7) | 172 |
C1B—H11B···O1Biv | 1.00 | 2.44 | 3.220 (7) | 134 |
N1C—H1C···O3Biv | 0.91 | 1.83 | 2.722 (7) | 167 |
N1C—H2C···O2Bvii | 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···O1Civ | 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. |