The title compound, commonly known as lidocaine, C14H22N2O, is a well known drug with local anaesthetic and anti-arrhythmic properties. Its structure has been reported previously, based on data of limited quality [Hanson & Banner (1974), Acta Cryst. B30, 2486-2488]. Results from a data collection at 173 K are now reported. The structure is characterized by the presence of two independent molecules in the asymmetric unit and by chains of hydrogen-bonded molecules in the crystal structure.
Supporting information
CCDC reference: 636633
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.047
- wR factor = 0.150
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT412_ALERT_2_B Short Intra XH3 .. XHn H12B .. H13A .. 1.79 Ang.
Alert level C
CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that
calculated from the cell parameter s.u.'s by > 2
Calculated cell volume su = 15.09
Cell volume su given = 12.00
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.31 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.96 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT391_ALERT_3_C Deviating Methyl C28 H-C-H Bond Angle ...... 101.00 Deg.
PLAT391_ALERT_3_C Deviating Methyl C28 H-C-H Bond Angle ...... 118.00 Deg.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 44.10 Deg.
C13B -N2 -C13A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 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
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
2-(Diethylamino)-
N-(2,6-dimethylphenyl)acetamide
top
Crystal data top
C14H22N2O | F(000) = 1024 |
Mr = 234.34 | Dx = 1.094 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 12697 reflections |
a = 12.9590 (3) Å | θ = 4.0–68.2° |
b = 13.8003 (3) Å | µ = 0.54 mm−1 |
c = 18.8288 (5) Å | T = 173 K |
β = 122.340 (3)° | Elongated prism, colourless |
V = 2845.00 (12) Å3 | 0.65 × 0.2 × 0.2 mm |
Z = 8 | |
Data collection top
Oxford Excalibur PX Ultra CCD area-detector diffractometer | 5218 independent reflections |
Radiation source: fine-focus sealed tube | 3547 reflections with I > 2σ(I) |
Oxford Enhance ULTRA assembly monochromator | Rint = 0.052 |
Detector resolution: 8.1241 pixels mm-1 | θmax = 68.2°, θmin = 4.0° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2006) | k = −16→16 |
Tmin = 0.763, Tmax = 0.897 | l = −22→19 |
34455 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0974P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
5218 reflections | Δρmax = 0.29 e Å−3 |
433 parameters | Δρmin = −0.24 e Å−3 |
6 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0015 (5) |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.15671 (15) | 0.26110 (12) | 0.54100 (9) | 0.0456 (4) | |
C2 | 0.10636 (16) | 0.35046 (12) | 0.50453 (10) | 0.0499 (4) | |
C3 | 0.1864 (2) | 0.43133 (15) | 0.50737 (14) | 0.0644 (5) | |
H3A | 0.249 (2) | 0.4552 (19) | 0.5693 (16) | 0.097* | |
H3B | 0.139 (2) | 0.488 (2) | 0.4739 (16) | 0.097* | |
H3C | 0.233 (2) | 0.4109 (19) | 0.4835 (16) | 0.097* | |
C4 | −0.01866 (17) | 0.36272 (15) | 0.46631 (10) | 0.0565 (5) | |
H4 | −0.0564 (19) | 0.4283 (15) | 0.4411 (13) | 0.068* | |
C5 | −0.09076 (19) | 0.28902 (16) | 0.46509 (11) | 0.0623 (5) | |
H5 | −0.176 (2) | 0.3027 (16) | 0.4401 (14) | 0.075* | |
C6 | −0.03930 (19) | 0.20077 (17) | 0.50129 (12) | 0.0631 (5) | |
H6 | −0.087 (2) | 0.1522 (17) | 0.5007 (13) | 0.076* | |
C7 | 0.08543 (17) | 0.18487 (13) | 0.53983 (11) | 0.0538 (4) | |
C8 | 0.1418 (2) | 0.08855 (17) | 0.57887 (17) | 0.0738 (6) | |
H8A | 0.208 (3) | 0.104 (2) | 0.6339 (19) | 0.111* | |
H8B | 0.080 (3) | 0.044 (2) | 0.5824 (17) | 0.111* | |
H8C | 0.164 (3) | 0.050 (2) | 0.5439 (18) | 0.111* | |
N1 | 0.28542 (13) | 0.24867 (10) | 0.58133 (8) | 0.0475 (3) | |
H1N | 0.3324 (19) | 0.2760 (14) | 0.6283 (13) | 0.057* | |
C9 | 0.33741 (15) | 0.20074 (12) | 0.54664 (9) | 0.0456 (4) | |
O1 | 0.27929 (12) | 0.15840 (10) | 0.47863 (7) | 0.0626 (4) | |
C10 | 0.47476 (17) | 0.20231 (16) | 0.59600 (11) | 0.0543 (4) | |
H10A | 0.5049 (19) | 0.1354 (16) | 0.6056 (12) | 0.065* | |
H10B | 0.502 (2) | 0.2338 (14) | 0.5624 (13) | 0.065* | |
N2 | 0.52983 (13) | 0.25150 (10) | 0.67615 (8) | 0.0515 (4) | |
C11 | 0.6027 (3) | 0.3329 (2) | 0.6818 (2) | 0.1123 (11) | |
H11A | 0.5592 | 0.3692 | 0.6282 | 0.135* | |
H11B | 0.6806 | 0.3092 | 0.6902 | 0.135* | |
C12 | 0.6296 (4) | 0.3999 (3) | 0.7527 (3) | 0.1510 (17) | |
H12A | 0.6687 | 0.4589 | 0.7492 | 0.226* | |
H12B | 0.6845 | 0.3676 | 0.8065 | 0.226* | |
H12C | 0.5532 | 0.4169 | 0.7487 | 0.226* | |
C13A | 0.6300 (4) | 0.1952 (3) | 0.7466 (2) | 0.0666 (15) | 0.512 (7) |
H13A | 0.6821 | 0.2385 | 0.7948 | 0.080* | 0.512 (7) |
H13B | 0.6814 | 0.1646 | 0.7286 | 0.080* | 0.512 (7) |
C14A | 0.5729 (9) | 0.1186 (5) | 0.7720 (4) | 0.107 (3) | 0.512 (7) |
H14A | 0.6372 | 0.0823 | 0.8202 | 0.161* | 0.512 (7) |
H14B | 0.5248 | 0.0742 | 0.7248 | 0.161* | 0.512 (7) |
H14C | 0.5195 | 0.1494 | 0.7874 | 0.161* | 0.512 (7) |
C13B | 0.5404 (4) | 0.1832 (3) | 0.7401 (2) | 0.0608 (15) | 0.488 (7) |
H13C | 0.4627 | 0.1473 | 0.7166 | 0.073* | 0.488 (7) |
H13D | 0.5540 | 0.2203 | 0.7894 | 0.073* | 0.488 (7) |
C14B | 0.6424 (5) | 0.1124 (5) | 0.7681 (3) | 0.087 (2) | 0.488 (7) |
H14D | 0.6455 | 0.0687 | 0.8102 | 0.131* | 0.488 (7) |
H14E | 0.7200 | 0.1475 | 0.7928 | 0.131* | 0.488 (7) |
H14F | 0.6287 | 0.0746 | 0.7197 | 0.131* | 0.488 (7) |
C15 | 0.41740 (15) | 0.23171 (12) | 0.38461 (9) | 0.0450 (4) | |
C16 | 0.53186 (16) | 0.18730 (13) | 0.42800 (10) | 0.0500 (4) | |
C17 | 0.5440 (2) | 0.08044 (16) | 0.42437 (14) | 0.0667 (5) | |
H17A | 0.518 (2) | 0.0584 (19) | 0.3647 (18) | 0.100* | |
H17B | 0.622 (3) | 0.057 (2) | 0.4606 (18) | 0.100* | |
H17C | 0.493 (3) | 0.043 (2) | 0.4381 (17) | 0.100* | |
C18 | 0.63408 (19) | 0.24638 (16) | 0.47592 (12) | 0.0620 (5) | |
H18 | 0.710 (2) | 0.2162 (16) | 0.5054 (14) | 0.074* | |
C19 | 0.6225 (2) | 0.34411 (17) | 0.48077 (14) | 0.0710 (6) | |
H19 | 0.690 (2) | 0.3808 (18) | 0.5093 (15) | 0.085* | |
C20 | 0.5087 (2) | 0.38660 (16) | 0.43738 (14) | 0.0721 (6) | |
H20 | 0.504 (2) | 0.4551 (19) | 0.4432 (15) | 0.087* | |
C21 | 0.40342 (18) | 0.33134 (13) | 0.38851 (11) | 0.0569 (5) | |
C22 | 0.2787 (2) | 0.3761 (2) | 0.34170 (17) | 0.0798 (6) | |
H22A | 0.215 (3) | 0.343 (2) | 0.3521 (19) | 0.120* | |
H22B | 0.283 (3) | 0.447 (3) | 0.3518 (18) | 0.120* | |
H22C | 0.247 (3) | 0.366 (2) | 0.285 (2) | 0.120* | |
N3 | 0.31060 (13) | 0.17385 (10) | 0.33790 (8) | 0.0475 (3) | |
H3N | 0.2676 (18) | 0.1613 (14) | 0.3609 (12) | 0.057* | |
C23 | 0.27214 (16) | 0.13607 (12) | 0.26209 (9) | 0.0482 (4) | |
O2 | 0.32684 (12) | 0.14519 (10) | 0.22571 (7) | 0.0617 (4) | |
C24 | 0.15472 (19) | 0.07774 (16) | 0.22338 (11) | 0.0603 (5) | |
H24A | 0.110 (2) | 0.0974 (15) | 0.1637 (14) | 0.072* | |
H24B | 0.1781 (19) | 0.0103 (17) | 0.2257 (13) | 0.072* | |
N4 | 0.08903 (13) | 0.08973 (11) | 0.26510 (8) | 0.0561 (4) | |
C25 | 0.0375 (2) | −0.00111 (18) | 0.27340 (14) | 0.0752 (6) | |
H25A | 0.003 (2) | −0.0423 (18) | 0.2210 (16) | 0.090* | |
H25B | −0.032 (2) | 0.0187 (18) | 0.2828 (15) | 0.090* | |
C26 | 0.1318 (3) | −0.0596 (2) | 0.34719 (17) | 0.0943 (9) | |
H26A | 0.161 (3) | −0.020 (3) | 0.398 (2) | 0.141* | |
H26B | 0.101 (3) | −0.122 (3) | 0.358 (2) | 0.141* | |
H26C | 0.205 (3) | −0.074 (2) | 0.339 (2) | 0.141* | |
C27 | 0.0012 (2) | 0.1701 (2) | 0.23025 (14) | 0.0779 (6) | |
H27A | −0.072 (2) | 0.1473 (18) | 0.1716 (17) | 0.094* | |
H27B | 0.044 (2) | 0.2244 (19) | 0.2136 (16) | 0.094* | |
C28 | −0.0307 (3) | 0.2088 (3) | 0.2911 (2) | 0.0973 (8) | |
H28A | −0.092 (4) | 0.267 (3) | 0.262 (2) | 0.146* | |
H28B | −0.087 (4) | 0.158 (3) | 0.296 (2) | 0.146* | |
H28C | 0.052 (4) | 0.229 (3) | 0.347 (2) | 0.146* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0438 (9) | 0.0542 (9) | 0.0381 (7) | −0.0009 (7) | 0.0214 (7) | −0.0029 (7) |
C2 | 0.0544 (10) | 0.0546 (10) | 0.0414 (8) | 0.0003 (8) | 0.0261 (8) | −0.0029 (7) |
C3 | 0.0713 (14) | 0.0555 (11) | 0.0691 (12) | −0.0055 (10) | 0.0394 (11) | 0.0005 (9) |
C4 | 0.0557 (11) | 0.0637 (11) | 0.0457 (9) | 0.0076 (9) | 0.0241 (8) | 0.0027 (8) |
C5 | 0.0478 (11) | 0.0838 (14) | 0.0517 (10) | 0.0044 (10) | 0.0241 (9) | 0.0018 (9) |
C6 | 0.0532 (12) | 0.0750 (13) | 0.0641 (11) | −0.0103 (10) | 0.0332 (9) | −0.0004 (10) |
C7 | 0.0533 (11) | 0.0581 (10) | 0.0518 (9) | −0.0020 (8) | 0.0293 (8) | 0.0010 (8) |
C8 | 0.0744 (15) | 0.0604 (13) | 0.0903 (15) | −0.0004 (11) | 0.0467 (12) | 0.0130 (12) |
N1 | 0.0437 (8) | 0.0578 (8) | 0.0388 (6) | −0.0030 (6) | 0.0207 (6) | −0.0096 (6) |
C9 | 0.0491 (9) | 0.0515 (9) | 0.0374 (7) | −0.0033 (7) | 0.0239 (7) | −0.0043 (7) |
O1 | 0.0562 (8) | 0.0858 (9) | 0.0469 (6) | −0.0128 (6) | 0.0283 (6) | −0.0220 (6) |
C10 | 0.0509 (10) | 0.0668 (12) | 0.0475 (9) | −0.0021 (9) | 0.0279 (8) | −0.0107 (8) |
N2 | 0.0505 (9) | 0.0533 (8) | 0.0406 (7) | −0.0013 (6) | 0.0177 (6) | −0.0056 (6) |
C11 | 0.126 (2) | 0.112 (2) | 0.144 (3) | −0.0615 (19) | 0.102 (2) | −0.0683 (19) |
C12 | 0.210 (4) | 0.119 (2) | 0.194 (4) | −0.096 (3) | 0.155 (3) | −0.100 (3) |
C13A | 0.067 (3) | 0.060 (3) | 0.050 (2) | 0.007 (2) | 0.0160 (19) | 0.0060 (17) |
C14A | 0.196 (9) | 0.063 (4) | 0.097 (4) | −0.001 (5) | 0.102 (6) | 0.007 (3) |
C13B | 0.056 (3) | 0.071 (3) | 0.048 (2) | 0.000 (2) | 0.0227 (19) | −0.005 (2) |
C14B | 0.078 (4) | 0.080 (4) | 0.054 (3) | 0.022 (3) | 0.003 (2) | −0.008 (3) |
C15 | 0.0444 (9) | 0.0511 (9) | 0.0409 (8) | −0.0049 (7) | 0.0238 (7) | −0.0012 (7) |
C16 | 0.0475 (10) | 0.0601 (10) | 0.0443 (8) | −0.0018 (8) | 0.0258 (7) | 0.0042 (7) |
C17 | 0.0685 (14) | 0.0639 (13) | 0.0613 (11) | 0.0127 (10) | 0.0306 (10) | 0.0076 (9) |
C18 | 0.0449 (11) | 0.0835 (15) | 0.0553 (10) | −0.0080 (9) | 0.0252 (9) | 0.0068 (9) |
C19 | 0.0589 (13) | 0.0768 (15) | 0.0649 (12) | −0.0259 (11) | 0.0247 (10) | −0.0033 (10) |
C20 | 0.0816 (16) | 0.0513 (11) | 0.0735 (13) | −0.0144 (11) | 0.0348 (12) | −0.0078 (10) |
C21 | 0.0595 (11) | 0.0541 (10) | 0.0541 (9) | −0.0006 (8) | 0.0284 (9) | 0.0005 (8) |
C22 | 0.0757 (16) | 0.0687 (14) | 0.0803 (14) | 0.0179 (12) | 0.0318 (13) | 0.0009 (12) |
N3 | 0.0465 (8) | 0.0575 (8) | 0.0411 (7) | −0.0102 (6) | 0.0251 (6) | −0.0044 (6) |
C23 | 0.0542 (10) | 0.0518 (9) | 0.0382 (8) | 0.0006 (7) | 0.0244 (7) | 0.0048 (7) |
O2 | 0.0650 (8) | 0.0828 (9) | 0.0437 (6) | −0.0031 (7) | 0.0333 (6) | 0.0053 (6) |
C24 | 0.0639 (12) | 0.0694 (12) | 0.0434 (9) | −0.0144 (10) | 0.0261 (8) | −0.0091 (9) |
N4 | 0.0469 (8) | 0.0696 (10) | 0.0449 (7) | −0.0125 (7) | 0.0199 (6) | −0.0005 (7) |
C25 | 0.0693 (14) | 0.0842 (15) | 0.0646 (12) | −0.0299 (12) | 0.0309 (11) | −0.0064 (11) |
C26 | 0.118 (2) | 0.0832 (17) | 0.0694 (14) | −0.0216 (16) | 0.0417 (15) | 0.0085 (12) |
C27 | 0.0580 (13) | 0.0978 (17) | 0.0643 (12) | 0.0056 (12) | 0.0235 (10) | 0.0148 (12) |
C28 | 0.0664 (16) | 0.129 (2) | 0.0957 (18) | 0.0241 (16) | 0.0425 (14) | 0.0106 (17) |
Geometric parameters (Å, º) top
C1—C2 | 1.392 (2) | C14B—H14D | 0.9800 |
C1—C7 | 1.392 (2) | C14B—H14E | 0.9800 |
C1—N1 | 1.426 (2) | C14B—H14F | 0.9800 |
C2—C4 | 1.387 (3) | C15—C21 | 1.394 (3) |
C2—C3 | 1.505 (3) | C15—C16 | 1.395 (2) |
C3—H3A | 1.06 (3) | C15—N3 | 1.423 (2) |
C3—H3B | 0.99 (3) | C16—C18 | 1.398 (3) |
C3—H3C | 0.97 (3) | C16—C17 | 1.488 (3) |
C4—C5 | 1.373 (3) | C17—H17A | 1.03 (3) |
C4—H4 | 1.02 (2) | C17—H17B | 0.92 (3) |
C5—C6 | 1.381 (3) | C17—H17C | 0.98 (3) |
C5—H5 | 0.96 (2) | C18—C19 | 1.366 (3) |
C6—C7 | 1.390 (3) | C18—H18 | 0.93 (2) |
C6—H6 | 0.91 (2) | C19—C20 | 1.377 (3) |
C7—C8 | 1.506 (3) | C19—H19 | 0.90 (3) |
C8—H8A | 0.95 (3) | C20—C21 | 1.395 (3) |
C8—H8B | 1.04 (3) | C20—H20 | 0.96 (3) |
C8—H8C | 1.01 (3) | C21—C22 | 1.499 (3) |
N1—C9 | 1.338 (2) | C22—H22A | 1.05 (3) |
N1—H1N | 0.85 (2) | C22—H22B | 1.00 (3) |
C9—O1 | 1.2314 (19) | C22—H22C | 0.92 (3) |
C9—C10 | 1.504 (3) | N3—C23 | 1.340 (2) |
C10—N2 | 1.447 (2) | N3—H3N | 0.89 (2) |
C10—H10A | 0.98 (2) | C23—O2 | 1.228 (2) |
C10—H10B | 0.97 (2) | C23—C24 | 1.519 (3) |
N2—C11 | 1.434 (3) | C24—N4 | 1.444 (2) |
N2—C13B | 1.476 (4) | C24—H24A | 0.99 (2) |
N2—C13A | 1.486 (4) | C24—H24B | 0.97 (2) |
C11—C12 | 1.504 (3) | N4—C25 | 1.468 (3) |
C11—H11A | 0.9900 | N4—C27 | 1.469 (3) |
C11—H11B | 0.9900 | C25—C26 | 1.503 (4) |
C12—H12A | 0.9800 | C25—H25A | 1.01 (3) |
C12—H12B | 0.9800 | C25—H25B | 1.04 (3) |
C12—H12C | 0.9800 | C26—H26A | 0.99 (4) |
C13A—C14A | 1.507 (5) | C26—H26B | 1.02 (4) |
C13A—H13A | 0.9900 | C26—H26C | 1.06 (4) |
C13A—H13B | 0.9900 | C27—C28 | 1.508 (4) |
C14A—H14A | 0.9800 | C27—H27A | 1.05 (3) |
C14A—H14B | 0.9800 | C27—H27B | 1.08 (3) |
C14A—H14C | 0.9800 | C28—H28A | 1.06 (4) |
C13B—C14B | 1.495 (5) | C28—H28B | 1.05 (4) |
C13B—H13C | 0.9900 | C28—H28C | 1.06 (4) |
C13B—H13D | 0.9900 | | |
| | | |
C2—C1—C7 | 121.97 (16) | H14D—C14B—H14E | 109.5 |
C2—C1—N1 | 118.38 (15) | C13B—C14B—H14F | 109.5 |
C7—C1—N1 | 119.65 (15) | H14D—C14B—H14F | 109.5 |
C4—C2—C1 | 118.24 (17) | H14E—C14B—H14F | 109.5 |
C4—C2—C3 | 121.30 (18) | C21—C15—C16 | 122.00 (16) |
C1—C2—C3 | 120.46 (17) | C21—C15—N3 | 118.38 (15) |
C2—C3—H3A | 112.5 (14) | C16—C15—N3 | 119.55 (15) |
C2—C3—H3B | 112.7 (15) | C15—C16—C18 | 117.72 (18) |
H3A—C3—H3B | 108 (2) | C15—C16—C17 | 120.90 (17) |
C2—C3—H3C | 110.9 (16) | C18—C16—C17 | 121.38 (18) |
H3A—C3—H3C | 107 (2) | C16—C17—H17A | 111.2 (14) |
H3B—C3—H3C | 105 (2) | C16—C17—H17B | 114.1 (17) |
C5—C4—C2 | 120.93 (19) | H17A—C17—H17B | 107 (2) |
C5—C4—H4 | 119.9 (12) | C16—C17—H17C | 113.8 (16) |
C2—C4—H4 | 119.1 (12) | H17A—C17—H17C | 105 (2) |
C4—C5—C6 | 120.03 (19) | H17B—C17—H17C | 105 (2) |
C4—C5—H5 | 117.2 (14) | C19—C18—C16 | 121.3 (2) |
C6—C5—H5 | 122.8 (14) | C19—C18—H18 | 121.4 (14) |
C5—C6—C7 | 121.1 (2) | C16—C18—H18 | 117.3 (14) |
C5—C6—H6 | 119.8 (15) | C18—C19—C20 | 120.2 (2) |
C7—C6—H6 | 119.1 (14) | C18—C19—H19 | 119.1 (16) |
C6—C7—C1 | 117.72 (18) | C20—C19—H19 | 120.5 (16) |
C6—C7—C8 | 121.29 (19) | C19—C20—C21 | 121.2 (2) |
C1—C7—C8 | 120.98 (18) | C19—C20—H20 | 117.5 (15) |
C7—C8—H8A | 104.8 (19) | C21—C20—H20 | 121.3 (15) |
C7—C8—H8B | 111.1 (16) | C15—C21—C20 | 117.71 (18) |
H8A—C8—H8B | 110 (2) | C15—C21—C22 | 120.35 (18) |
C7—C8—H8C | 112.6 (17) | C20—C21—C22 | 121.9 (2) |
H8A—C8—H8C | 115 (3) | C21—C22—H22A | 114.5 (17) |
H8B—C8—H8C | 104 (2) | C21—C22—H22B | 111.3 (18) |
C9—N1—C1 | 123.42 (14) | H22A—C22—H22B | 111 (2) |
C9—N1—H1N | 117.5 (14) | C21—C22—H22C | 107 (2) |
C1—N1—H1N | 118.9 (14) | H22A—C22—H22C | 104 (3) |
O1—C9—N1 | 123.69 (16) | H22B—C22—H22C | 109 (3) |
O1—C9—C10 | 120.85 (14) | C23—N3—C15 | 124.13 (14) |
N1—C9—C10 | 115.46 (14) | C23—N3—H3N | 118.1 (12) |
N2—C10—C9 | 114.30 (14) | C15—N3—H3N | 117.7 (12) |
N2—C10—H10A | 108.9 (12) | O2—C23—N3 | 123.88 (16) |
C9—C10—H10A | 108.9 (12) | O2—C23—C24 | 121.05 (15) |
N2—C10—H10B | 108.6 (12) | N3—C23—C24 | 115.05 (15) |
C9—C10—H10B | 108.9 (13) | N4—C24—C23 | 114.14 (14) |
H10A—C10—H10B | 107.0 (17) | N4—C24—H24A | 115.5 (12) |
C11—N2—C10 | 112.48 (17) | C23—C24—H24A | 103.1 (12) |
C11—N2—C13B | 132.0 (2) | N4—C24—H24B | 110.2 (13) |
C10—N2—C13B | 109.3 (2) | C23—C24—H24B | 106.1 (13) |
C11—N2—C13A | 96.7 (3) | H24A—C24—H24B | 107.0 (18) |
C10—N2—C13A | 113.2 (2) | C24—N4—C25 | 113.23 (18) |
C13B—N2—C13A | 44.1 (2) | C24—N4—C27 | 112.65 (16) |
N2—C11—C12 | 112.2 (2) | C25—N4—C27 | 113.86 (18) |
N2—C11—H11A | 109.2 | N4—C25—C26 | 111.47 (19) |
C12—C11—H11A | 109.2 | N4—C25—H25A | 111.4 (14) |
N2—C11—H11B | 109.2 | C26—C25—H25A | 108.4 (14) |
C12—C11—H11B | 109.2 | N4—C25—H25B | 106.1 (14) |
H11A—C11—H11B | 107.9 | C26—C25—H25B | 109.4 (14) |
C11—C12—H12A | 109.5 | H25A—C25—H25B | 110 (2) |
C11—C12—H12B | 109.5 | C25—C26—H26A | 107 (2) |
H12A—C12—H12B | 109.5 | C25—C26—H26B | 116 (2) |
C11—C12—H12C | 109.5 | H26A—C26—H26B | 105 (3) |
H12A—C12—H12C | 109.5 | C25—C26—H26C | 108.1 (19) |
H12B—C12—H12C | 109.5 | H26A—C26—H26C | 110 (3) |
N2—C13A—C14A | 107.9 (5) | H26B—C26—H26C | 111 (3) |
N2—C13A—H13A | 110.1 | N4—C27—C28 | 112.9 (2) |
C14A—C13A—H13A | 110.1 | N4—C27—H27A | 106.9 (14) |
N2—C13A—H13B | 110.1 | C28—C27—H27A | 116.7 (14) |
C14A—C13A—H13B | 110.1 | N4—C27—H27B | 104.9 (14) |
H13A—C13A—H13B | 108.4 | C28—C27—H27B | 111.7 (14) |
N2—C13B—C14B | 112.6 (4) | H27A—C27—H27B | 102.6 (19) |
N2—C13B—H13C | 109.1 | C27—C28—H28A | 108 (2) |
C14B—C13B—H13C | 109.1 | C27—C28—H28B | 108 (2) |
N2—C13B—H13D | 109.1 | H28A—C28—H28B | 101 (3) |
C14B—C13B—H13D | 109.1 | C27—C28—H28C | 107 (2) |
H13C—C13B—H13D | 107.8 | H28A—C28—H28C | 114 (3) |
C13B—C14B—H14D | 109.5 | H28B—C28—H28C | 118 (3) |
C13B—C14B—H14E | 109.5 | | |
| | | |
C7—C1—C2—C4 | 0.1 (2) | C11—N2—C13B—C14B | −73.6 (4) |
N1—C1—C2—C4 | −179.17 (14) | C10—N2—C13B—C14B | 75.7 (4) |
C7—C1—C2—C3 | 179.73 (16) | C13A—N2—C13B—C14B | −28.1 (4) |
N1—C1—C2—C3 | 0.4 (2) | C21—C15—C16—C18 | −0.4 (2) |
C1—C2—C4—C5 | 0.6 (2) | N3—C15—C16—C18 | −177.41 (14) |
C3—C2—C4—C5 | −179.03 (18) | C21—C15—C16—C17 | 178.53 (17) |
C2—C4—C5—C6 | −0.8 (3) | N3—C15—C16—C17 | 1.5 (2) |
C4—C5—C6—C7 | 0.4 (3) | C15—C16—C18—C19 | 0.5 (3) |
C5—C6—C7—C1 | 0.3 (3) | C17—C16—C18—C19 | −178.40 (19) |
C5—C6—C7—C8 | −179.6 (2) | C16—C18—C19—C20 | −0.6 (3) |
C2—C1—C7—C6 | −0.5 (2) | C18—C19—C20—C21 | 0.6 (3) |
N1—C1—C7—C6 | 178.75 (15) | C16—C15—C21—C20 | 0.4 (3) |
C2—C1—C7—C8 | 179.32 (18) | N3—C15—C21—C20 | 177.41 (16) |
N1—C1—C7—C8 | −1.4 (3) | C16—C15—C21—C22 | −179.32 (18) |
C2—C1—N1—C9 | −102.67 (19) | N3—C15—C21—C22 | −2.3 (3) |
C7—C1—N1—C9 | 78.0 (2) | C19—C20—C21—C15 | −0.5 (3) |
C1—N1—C9—O1 | −4.0 (3) | C19—C20—C21—C22 | 179.2 (2) |
C1—N1—C9—C10 | 175.29 (16) | C21—C15—N3—C23 | 104.99 (19) |
O1—C9—C10—N2 | −177.58 (16) | C16—C15—N3—C23 | −77.9 (2) |
N1—C9—C10—N2 | 3.1 (2) | C15—N3—C23—O2 | 2.0 (3) |
C9—C10—N2—C11 | −119.5 (2) | C15—N3—C23—C24 | −179.22 (16) |
C9—C10—N2—C13B | 84.8 (3) | O2—C23—C24—N4 | −168.24 (17) |
C9—C10—N2—C13A | 132.1 (2) | N3—C23—C24—N4 | 13.0 (2) |
C10—N2—C11—C12 | 163.5 (3) | C23—C24—N4—C25 | −139.36 (17) |
C13B—N2—C11—C12 | −48.0 (5) | C23—C24—N4—C27 | 89.6 (2) |
C13A—N2—C11—C12 | −77.9 (3) | C24—N4—C25—C26 | 81.4 (2) |
C11—N2—C13A—C14A | 163.3 (4) | C27—N4—C25—C26 | −148.2 (2) |
C10—N2—C13A—C14A | −78.7 (4) | C24—N4—C27—C28 | −157.4 (2) |
C13B—N2—C13A—C14A | 15.5 (3) | C25—N4—C27—C28 | 71.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O1 | 0.89 (2) | 2.14 (2) | 2.8952 (18) | 142.6 (17) |
N1—H1N···O2i | 0.85 (2) | 2.17 (2) | 2.8746 (17) | 140.9 (18) |
N1—H1N···N2 | 0.85 (2) | 2.24 (2) | 2.678 (2) | 112.3 (16) |
N3—H3N···N4 | 0.89 (2) | 2.262 (19) | 2.695 (2) | 109.7 (15) |
Symmetry code: (i) x, −y+1/2, z+1/2. |