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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001523/fl2092sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001523/fl2092Isup2.hkl
Contains datablock I

CCDC reference: 636633

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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
C14H22N2OF(000) = 1024
Mr = 234.34Dx = 1.094 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 12697 reflections
a = 12.9590 (3) Åθ = 4.0–68.2°
b = 13.8003 (3) ŵ = 0.54 mm1
c = 18.8288 (5) ÅT = 173 K
β = 122.340 (3)°Elongated prism, colourless
V = 2845.00 (12) Å30.65 × 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 tube3547 reflections with I > 2σ(I)
Oxford Enhance ULTRA assembly monochromatorRint = 0.052
Detector resolution: 8.1241 pixels mm-1θmax = 68.2°, θmin = 4.0°
ω scansh = 1515
Absorption correction: multi-scan
(ABSPACK; Oxford Diffraction, 2006)
k = 1616
Tmin = 0.763, Tmax = 0.897l = 2219
34455 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047H 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 reflectionsΔρmax = 0.29 e Å3
433 parametersΔρmin = 0.24 e Å3
6 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/UeqOcc. (<1)
C10.15671 (15)0.26110 (12)0.54100 (9)0.0456 (4)
C20.10636 (16)0.35046 (12)0.50453 (10)0.0499 (4)
C30.1864 (2)0.43133 (15)0.50737 (14)0.0644 (5)
H3A0.249 (2)0.4552 (19)0.5693 (16)0.097*
H3B0.139 (2)0.488 (2)0.4739 (16)0.097*
H3C0.233 (2)0.4109 (19)0.4835 (16)0.097*
C40.01866 (17)0.36272 (15)0.46631 (10)0.0565 (5)
H40.0564 (19)0.4283 (15)0.4411 (13)0.068*
C50.09076 (19)0.28902 (16)0.46509 (11)0.0623 (5)
H50.176 (2)0.3027 (16)0.4401 (14)0.075*
C60.03930 (19)0.20077 (17)0.50129 (12)0.0631 (5)
H60.087 (2)0.1522 (17)0.5007 (13)0.076*
C70.08543 (17)0.18487 (13)0.53983 (11)0.0538 (4)
C80.1418 (2)0.08855 (17)0.57887 (17)0.0738 (6)
H8A0.208 (3)0.104 (2)0.6339 (19)0.111*
H8B0.080 (3)0.044 (2)0.5824 (17)0.111*
H8C0.164 (3)0.050 (2)0.5439 (18)0.111*
N10.28542 (13)0.24867 (10)0.58133 (8)0.0475 (3)
H1N0.3324 (19)0.2760 (14)0.6283 (13)0.057*
C90.33741 (15)0.20074 (12)0.54664 (9)0.0456 (4)
O10.27929 (12)0.15840 (10)0.47863 (7)0.0626 (4)
C100.47476 (17)0.20231 (16)0.59600 (11)0.0543 (4)
H10A0.5049 (19)0.1354 (16)0.6056 (12)0.065*
H10B0.502 (2)0.2338 (14)0.5624 (13)0.065*
N20.52983 (13)0.25150 (10)0.67615 (8)0.0515 (4)
C110.6027 (3)0.3329 (2)0.6818 (2)0.1123 (11)
H11A0.55920.36920.62820.135*
H11B0.68060.30920.69020.135*
C120.6296 (4)0.3999 (3)0.7527 (3)0.1510 (17)
H12A0.66870.45890.74920.226*
H12B0.68450.36760.80650.226*
H12C0.55320.41690.74870.226*
C13A0.6300 (4)0.1952 (3)0.7466 (2)0.0666 (15)0.512 (7)
H13A0.68210.23850.79480.080*0.512 (7)
H13B0.68140.16460.72860.080*0.512 (7)
C14A0.5729 (9)0.1186 (5)0.7720 (4)0.107 (3)0.512 (7)
H14A0.63720.08230.82020.161*0.512 (7)
H14B0.52480.07420.72480.161*0.512 (7)
H14C0.51950.14940.78740.161*0.512 (7)
C13B0.5404 (4)0.1832 (3)0.7401 (2)0.0608 (15)0.488 (7)
H13C0.46270.14730.71660.073*0.488 (7)
H13D0.55400.22030.78940.073*0.488 (7)
C14B0.6424 (5)0.1124 (5)0.7681 (3)0.087 (2)0.488 (7)
H14D0.64550.06870.81020.131*0.488 (7)
H14E0.72000.14750.79280.131*0.488 (7)
H14F0.62870.07460.71970.131*0.488 (7)
C150.41740 (15)0.23171 (12)0.38461 (9)0.0450 (4)
C160.53186 (16)0.18730 (13)0.42800 (10)0.0500 (4)
C170.5440 (2)0.08044 (16)0.42437 (14)0.0667 (5)
H17A0.518 (2)0.0584 (19)0.3647 (18)0.100*
H17B0.622 (3)0.057 (2)0.4606 (18)0.100*
H17C0.493 (3)0.043 (2)0.4381 (17)0.100*
C180.63408 (19)0.24638 (16)0.47592 (12)0.0620 (5)
H180.710 (2)0.2162 (16)0.5054 (14)0.074*
C190.6225 (2)0.34411 (17)0.48077 (14)0.0710 (6)
H190.690 (2)0.3808 (18)0.5093 (15)0.085*
C200.5087 (2)0.38660 (16)0.43738 (14)0.0721 (6)
H200.504 (2)0.4551 (19)0.4432 (15)0.087*
C210.40342 (18)0.33134 (13)0.38851 (11)0.0569 (5)
C220.2787 (2)0.3761 (2)0.34170 (17)0.0798 (6)
H22A0.215 (3)0.343 (2)0.3521 (19)0.120*
H22B0.283 (3)0.447 (3)0.3518 (18)0.120*
H22C0.247 (3)0.366 (2)0.285 (2)0.120*
N30.31060 (13)0.17385 (10)0.33790 (8)0.0475 (3)
H3N0.2676 (18)0.1613 (14)0.3609 (12)0.057*
C230.27214 (16)0.13607 (12)0.26209 (9)0.0482 (4)
O20.32684 (12)0.14519 (10)0.22571 (7)0.0617 (4)
C240.15472 (19)0.07774 (16)0.22338 (11)0.0603 (5)
H24A0.110 (2)0.0974 (15)0.1637 (14)0.072*
H24B0.1781 (19)0.0103 (17)0.2257 (13)0.072*
N40.08903 (13)0.08973 (11)0.26510 (8)0.0561 (4)
C250.0375 (2)0.00111 (18)0.27340 (14)0.0752 (6)
H25A0.003 (2)0.0423 (18)0.2210 (16)0.090*
H25B0.032 (2)0.0187 (18)0.2828 (15)0.090*
C260.1318 (3)0.0596 (2)0.34719 (17)0.0943 (9)
H26A0.161 (3)0.020 (3)0.398 (2)0.141*
H26B0.101 (3)0.122 (3)0.358 (2)0.141*
H26C0.205 (3)0.074 (2)0.339 (2)0.141*
C270.0012 (2)0.1701 (2)0.23025 (14)0.0779 (6)
H27A0.072 (2)0.1473 (18)0.1716 (17)0.094*
H27B0.044 (2)0.2244 (19)0.2136 (16)0.094*
C280.0307 (3)0.2088 (3)0.2911 (2)0.0973 (8)
H28A0.092 (4)0.267 (3)0.262 (2)0.146*
H28B0.087 (4)0.158 (3)0.296 (2)0.146*
H28C0.052 (4)0.229 (3)0.347 (2)0.146*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0438 (9)0.0542 (9)0.0381 (7)0.0009 (7)0.0214 (7)0.0029 (7)
C20.0544 (10)0.0546 (10)0.0414 (8)0.0003 (8)0.0261 (8)0.0029 (7)
C30.0713 (14)0.0555 (11)0.0691 (12)0.0055 (10)0.0394 (11)0.0005 (9)
C40.0557 (11)0.0637 (11)0.0457 (9)0.0076 (9)0.0241 (8)0.0027 (8)
C50.0478 (11)0.0838 (14)0.0517 (10)0.0044 (10)0.0241 (9)0.0018 (9)
C60.0532 (12)0.0750 (13)0.0641 (11)0.0103 (10)0.0332 (9)0.0004 (10)
C70.0533 (11)0.0581 (10)0.0518 (9)0.0020 (8)0.0293 (8)0.0010 (8)
C80.0744 (15)0.0604 (13)0.0903 (15)0.0004 (11)0.0467 (12)0.0130 (12)
N10.0437 (8)0.0578 (8)0.0388 (6)0.0030 (6)0.0207 (6)0.0096 (6)
C90.0491 (9)0.0515 (9)0.0374 (7)0.0033 (7)0.0239 (7)0.0043 (7)
O10.0562 (8)0.0858 (9)0.0469 (6)0.0128 (6)0.0283 (6)0.0220 (6)
C100.0509 (10)0.0668 (12)0.0475 (9)0.0021 (9)0.0279 (8)0.0107 (8)
N20.0505 (9)0.0533 (8)0.0406 (7)0.0013 (6)0.0177 (6)0.0056 (6)
C110.126 (2)0.112 (2)0.144 (3)0.0615 (19)0.102 (2)0.0683 (19)
C120.210 (4)0.119 (2)0.194 (4)0.096 (3)0.155 (3)0.100 (3)
C13A0.067 (3)0.060 (3)0.050 (2)0.007 (2)0.0160 (19)0.0060 (17)
C14A0.196 (9)0.063 (4)0.097 (4)0.001 (5)0.102 (6)0.007 (3)
C13B0.056 (3)0.071 (3)0.048 (2)0.000 (2)0.0227 (19)0.005 (2)
C14B0.078 (4)0.080 (4)0.054 (3)0.022 (3)0.003 (2)0.008 (3)
C150.0444 (9)0.0511 (9)0.0409 (8)0.0049 (7)0.0238 (7)0.0012 (7)
C160.0475 (10)0.0601 (10)0.0443 (8)0.0018 (8)0.0258 (7)0.0042 (7)
C170.0685 (14)0.0639 (13)0.0613 (11)0.0127 (10)0.0306 (10)0.0076 (9)
C180.0449 (11)0.0835 (15)0.0553 (10)0.0080 (9)0.0252 (9)0.0068 (9)
C190.0589 (13)0.0768 (15)0.0649 (12)0.0259 (11)0.0247 (10)0.0033 (10)
C200.0816 (16)0.0513 (11)0.0735 (13)0.0144 (11)0.0348 (12)0.0078 (10)
C210.0595 (11)0.0541 (10)0.0541 (9)0.0006 (8)0.0284 (9)0.0005 (8)
C220.0757 (16)0.0687 (14)0.0803 (14)0.0179 (12)0.0318 (13)0.0009 (12)
N30.0465 (8)0.0575 (8)0.0411 (7)0.0102 (6)0.0251 (6)0.0044 (6)
C230.0542 (10)0.0518 (9)0.0382 (8)0.0006 (7)0.0244 (7)0.0048 (7)
O20.0650 (8)0.0828 (9)0.0437 (6)0.0031 (7)0.0333 (6)0.0053 (6)
C240.0639 (12)0.0694 (12)0.0434 (9)0.0144 (10)0.0261 (8)0.0091 (9)
N40.0469 (8)0.0696 (10)0.0449 (7)0.0125 (7)0.0199 (6)0.0005 (7)
C250.0693 (14)0.0842 (15)0.0646 (12)0.0299 (12)0.0309 (11)0.0064 (11)
C260.118 (2)0.0832 (17)0.0694 (14)0.0216 (16)0.0417 (15)0.0085 (12)
C270.0580 (13)0.0978 (17)0.0643 (12)0.0056 (12)0.0235 (10)0.0148 (12)
C280.0664 (16)0.129 (2)0.0957 (18)0.0241 (16)0.0425 (14)0.0106 (17)
Geometric parameters (Å, º) top
C1—C21.392 (2)C14B—H14D0.9800
C1—C71.392 (2)C14B—H14E0.9800
C1—N11.426 (2)C14B—H14F0.9800
C2—C41.387 (3)C15—C211.394 (3)
C2—C31.505 (3)C15—C161.395 (2)
C3—H3A1.06 (3)C15—N31.423 (2)
C3—H3B0.99 (3)C16—C181.398 (3)
C3—H3C0.97 (3)C16—C171.488 (3)
C4—C51.373 (3)C17—H17A1.03 (3)
C4—H41.02 (2)C17—H17B0.92 (3)
C5—C61.381 (3)C17—H17C0.98 (3)
C5—H50.96 (2)C18—C191.366 (3)
C6—C71.390 (3)C18—H180.93 (2)
C6—H60.91 (2)C19—C201.377 (3)
C7—C81.506 (3)C19—H190.90 (3)
C8—H8A0.95 (3)C20—C211.395 (3)
C8—H8B1.04 (3)C20—H200.96 (3)
C8—H8C1.01 (3)C21—C221.499 (3)
N1—C91.338 (2)C22—H22A1.05 (3)
N1—H1N0.85 (2)C22—H22B1.00 (3)
C9—O11.2314 (19)C22—H22C0.92 (3)
C9—C101.504 (3)N3—C231.340 (2)
C10—N21.447 (2)N3—H3N0.89 (2)
C10—H10A0.98 (2)C23—O21.228 (2)
C10—H10B0.97 (2)C23—C241.519 (3)
N2—C111.434 (3)C24—N41.444 (2)
N2—C13B1.476 (4)C24—H24A0.99 (2)
N2—C13A1.486 (4)C24—H24B0.97 (2)
C11—C121.504 (3)N4—C251.468 (3)
C11—H11A0.9900N4—C271.469 (3)
C11—H11B0.9900C25—C261.503 (4)
C12—H12A0.9800C25—H25A1.01 (3)
C12—H12B0.9800C25—H25B1.04 (3)
C12—H12C0.9800C26—H26A0.99 (4)
C13A—C14A1.507 (5)C26—H26B1.02 (4)
C13A—H13A0.9900C26—H26C1.06 (4)
C13A—H13B0.9900C27—C281.508 (4)
C14A—H14A0.9800C27—H27A1.05 (3)
C14A—H14B0.9800C27—H27B1.08 (3)
C14A—H14C0.9800C28—H28A1.06 (4)
C13B—C14B1.495 (5)C28—H28B1.05 (4)
C13B—H13C0.9900C28—H28C1.06 (4)
C13B—H13D0.9900
C2—C1—C7121.97 (16)H14D—C14B—H14E109.5
C2—C1—N1118.38 (15)C13B—C14B—H14F109.5
C7—C1—N1119.65 (15)H14D—C14B—H14F109.5
C4—C2—C1118.24 (17)H14E—C14B—H14F109.5
C4—C2—C3121.30 (18)C21—C15—C16122.00 (16)
C1—C2—C3120.46 (17)C21—C15—N3118.38 (15)
C2—C3—H3A112.5 (14)C16—C15—N3119.55 (15)
C2—C3—H3B112.7 (15)C15—C16—C18117.72 (18)
H3A—C3—H3B108 (2)C15—C16—C17120.90 (17)
C2—C3—H3C110.9 (16)C18—C16—C17121.38 (18)
H3A—C3—H3C107 (2)C16—C17—H17A111.2 (14)
H3B—C3—H3C105 (2)C16—C17—H17B114.1 (17)
C5—C4—C2120.93 (19)H17A—C17—H17B107 (2)
C5—C4—H4119.9 (12)C16—C17—H17C113.8 (16)
C2—C4—H4119.1 (12)H17A—C17—H17C105 (2)
C4—C5—C6120.03 (19)H17B—C17—H17C105 (2)
C4—C5—H5117.2 (14)C19—C18—C16121.3 (2)
C6—C5—H5122.8 (14)C19—C18—H18121.4 (14)
C5—C6—C7121.1 (2)C16—C18—H18117.3 (14)
C5—C6—H6119.8 (15)C18—C19—C20120.2 (2)
C7—C6—H6119.1 (14)C18—C19—H19119.1 (16)
C6—C7—C1117.72 (18)C20—C19—H19120.5 (16)
C6—C7—C8121.29 (19)C19—C20—C21121.2 (2)
C1—C7—C8120.98 (18)C19—C20—H20117.5 (15)
C7—C8—H8A104.8 (19)C21—C20—H20121.3 (15)
C7—C8—H8B111.1 (16)C15—C21—C20117.71 (18)
H8A—C8—H8B110 (2)C15—C21—C22120.35 (18)
C7—C8—H8C112.6 (17)C20—C21—C22121.9 (2)
H8A—C8—H8C115 (3)C21—C22—H22A114.5 (17)
H8B—C8—H8C104 (2)C21—C22—H22B111.3 (18)
C9—N1—C1123.42 (14)H22A—C22—H22B111 (2)
C9—N1—H1N117.5 (14)C21—C22—H22C107 (2)
C1—N1—H1N118.9 (14)H22A—C22—H22C104 (3)
O1—C9—N1123.69 (16)H22B—C22—H22C109 (3)
O1—C9—C10120.85 (14)C23—N3—C15124.13 (14)
N1—C9—C10115.46 (14)C23—N3—H3N118.1 (12)
N2—C10—C9114.30 (14)C15—N3—H3N117.7 (12)
N2—C10—H10A108.9 (12)O2—C23—N3123.88 (16)
C9—C10—H10A108.9 (12)O2—C23—C24121.05 (15)
N2—C10—H10B108.6 (12)N3—C23—C24115.05 (15)
C9—C10—H10B108.9 (13)N4—C24—C23114.14 (14)
H10A—C10—H10B107.0 (17)N4—C24—H24A115.5 (12)
C11—N2—C10112.48 (17)C23—C24—H24A103.1 (12)
C11—N2—C13B132.0 (2)N4—C24—H24B110.2 (13)
C10—N2—C13B109.3 (2)C23—C24—H24B106.1 (13)
C11—N2—C13A96.7 (3)H24A—C24—H24B107.0 (18)
C10—N2—C13A113.2 (2)C24—N4—C25113.23 (18)
C13B—N2—C13A44.1 (2)C24—N4—C27112.65 (16)
N2—C11—C12112.2 (2)C25—N4—C27113.86 (18)
N2—C11—H11A109.2N4—C25—C26111.47 (19)
C12—C11—H11A109.2N4—C25—H25A111.4 (14)
N2—C11—H11B109.2C26—C25—H25A108.4 (14)
C12—C11—H11B109.2N4—C25—H25B106.1 (14)
H11A—C11—H11B107.9C26—C25—H25B109.4 (14)
C11—C12—H12A109.5H25A—C25—H25B110 (2)
C11—C12—H12B109.5C25—C26—H26A107 (2)
H12A—C12—H12B109.5C25—C26—H26B116 (2)
C11—C12—H12C109.5H26A—C26—H26B105 (3)
H12A—C12—H12C109.5C25—C26—H26C108.1 (19)
H12B—C12—H12C109.5H26A—C26—H26C110 (3)
N2—C13A—C14A107.9 (5)H26B—C26—H26C111 (3)
N2—C13A—H13A110.1N4—C27—C28112.9 (2)
C14A—C13A—H13A110.1N4—C27—H27A106.9 (14)
N2—C13A—H13B110.1C28—C27—H27A116.7 (14)
C14A—C13A—H13B110.1N4—C27—H27B104.9 (14)
H13A—C13A—H13B108.4C28—C27—H27B111.7 (14)
N2—C13B—C14B112.6 (4)H27A—C27—H27B102.6 (19)
N2—C13B—H13C109.1C27—C28—H28A108 (2)
C14B—C13B—H13C109.1C27—C28—H28B108 (2)
N2—C13B—H13D109.1H28A—C28—H28B101 (3)
C14B—C13B—H13D109.1C27—C28—H28C107 (2)
H13C—C13B—H13D107.8H28A—C28—H28C114 (3)
C13B—C14B—H14D109.5H28B—C28—H28C118 (3)
C13B—C14B—H14E109.5
C7—C1—C2—C40.1 (2)C11—N2—C13B—C14B73.6 (4)
N1—C1—C2—C4179.17 (14)C10—N2—C13B—C14B75.7 (4)
C7—C1—C2—C3179.73 (16)C13A—N2—C13B—C14B28.1 (4)
N1—C1—C2—C30.4 (2)C21—C15—C16—C180.4 (2)
C1—C2—C4—C50.6 (2)N3—C15—C16—C18177.41 (14)
C3—C2—C4—C5179.03 (18)C21—C15—C16—C17178.53 (17)
C2—C4—C5—C60.8 (3)N3—C15—C16—C171.5 (2)
C4—C5—C6—C70.4 (3)C15—C16—C18—C190.5 (3)
C5—C6—C7—C10.3 (3)C17—C16—C18—C19178.40 (19)
C5—C6—C7—C8179.6 (2)C16—C18—C19—C200.6 (3)
C2—C1—C7—C60.5 (2)C18—C19—C20—C210.6 (3)
N1—C1—C7—C6178.75 (15)C16—C15—C21—C200.4 (3)
C2—C1—C7—C8179.32 (18)N3—C15—C21—C20177.41 (16)
N1—C1—C7—C81.4 (3)C16—C15—C21—C22179.32 (18)
C2—C1—N1—C9102.67 (19)N3—C15—C21—C222.3 (3)
C7—C1—N1—C978.0 (2)C19—C20—C21—C150.5 (3)
C1—N1—C9—O14.0 (3)C19—C20—C21—C22179.2 (2)
C1—N1—C9—C10175.29 (16)C21—C15—N3—C23104.99 (19)
O1—C9—C10—N2177.58 (16)C16—C15—N3—C2377.9 (2)
N1—C9—C10—N23.1 (2)C15—N3—C23—O22.0 (3)
C9—C10—N2—C11119.5 (2)C15—N3—C23—C24179.22 (16)
C9—C10—N2—C13B84.8 (3)O2—C23—C24—N4168.24 (17)
C9—C10—N2—C13A132.1 (2)N3—C23—C24—N413.0 (2)
C10—N2—C11—C12163.5 (3)C23—C24—N4—C25139.36 (17)
C13B—N2—C11—C1248.0 (5)C23—C24—N4—C2789.6 (2)
C13A—N2—C11—C1277.9 (3)C24—N4—C25—C2681.4 (2)
C11—N2—C13A—C14A163.3 (4)C27—N4—C25—C26148.2 (2)
C10—N2—C13A—C14A78.7 (4)C24—N4—C27—C28157.4 (2)
C13B—N2—C13A—C14A15.5 (3)C25—N4—C27—C2871.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O10.89 (2)2.14 (2)2.8952 (18)142.6 (17)
N1—H1N···O2i0.85 (2)2.17 (2)2.8746 (17)140.9 (18)
N1—H1N···N20.85 (2)2.24 (2)2.678 (2)112.3 (16)
N3—H3N···N40.89 (2)2.262 (19)2.695 (2)109.7 (15)
Symmetry code: (i) x, y+1/2, z+1/2.
 

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