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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2574.
Published online 2009 September 30. doi:  10.1107/S1600536809038859
PMCID: PMC2970238

4-(Methyl­amino)benzoic acid

Abstract

The asymmetric unit of the title compound, C8H9NO2, contains three crystallographically independent mol­ecules, which are essentially planar, the carboxyl O atoms deviating by 0.091 (3), 0.101 (2) and 0.164 (3) Å from the mean plane through the non-H atoms. In the crystal, all three mol­ecules form O—H(...)O hydrogen-bonded about inversion centers, forming eight-membered rings with graph-set notation R 2 2(8). In addition, N—H(...)O hydrogen bonding and C—H(...)π inter­actions reinforce the packing.

Related literature

For comparison bond-length data in some substituted amino benzoic acid compounds, see: Dzierżawska-Majewska et al. (2006 [triangle]); Smith et al. (2007 [triangle]).

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Object name is e-65-o2574-scheme1.jpg

Experimental

Crystal data

  • C8H9NO2
  • M r = 151.16
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2574-efi1.jpg
  • a = 5.0456 (3) Å
  • b = 36.339 (2) Å
  • c = 12.6496 (5) Å
  • β = 96.129 (4)°
  • V = 2306.1 (2) Å3
  • Z = 12
  • Cu Kα radiation
  • μ = 0.78 mm−1
  • T = 296 K
  • 0.11 × 0.08 × 0.06 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini CCD detector
  • Absorption correction: none
  • 7671 measured reflections
  • 4266 independent reflections
  • 2680 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.239
  • S = 1.08
  • 4266 reflections
  • 301 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038859/hg2564sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038859/hg2564Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Cumhriyet University Reseach Foundation (CUBAP grant No 2009/F-266) for financial support.

supplementary crystallographic information

Comment

Three independent molecules of the title compound (I) in the asymmetric unit are shown in Fig. 1.The bond lengths and angles in the three molecules have normal values. These molecules are not essentially planar (r.m.s. deviations from the mean plane of the non-H atoms are -0.091 (3) Å for atom O1 of the molecule 1, -0.101 (2)Å and 0.164 (3) Å, for atoms O1, O3 and O5 of each molecule, respectively). The dihedral angles between the benzene rings A(C2–C7), B(C10–C17) and C(C18–C23) are A/B = 88.27 (15)°, A/C = 10.63 (16)° and B/C = 89.16 (15)°.

In this structure, the three molecules all form O—H···O hydrogen bonded dimers, between molecules lying about inversion centers, forming eight-membered rings with an R22(8) motif in graph-set notation (Fig. 2). Further, N—H···O hydrogen bonding and C—H···π interactions reinforces the packing (Table 1, Fig. 3).

Experimental

4-(Methylamino)benzoic acid (0.60468 g, 0.4 mol) (Aldrich) was added to water of 300 ml. The temperature was kept constant at 343 K and solution stirred in a mixer for 1 h, and then solution was left at room temperature to be crystalline. A day later, colourless crystals formed.

Refinement

All H atoms were observed in a differences Fourier map. The H atoms in the title compound were placed geometrically [C—H = 0.93 Å for aromatic, C—H = 0.93 Å for methyl, O—H = 0.82 Å for hydroxyl and N—H = 0.86 Å for NH] and refined with Uiso(H) = 1.2 or 1.5Ueq(C, N,O), using a riding model. To determine the OH groups correctly, the OH H atoms were geometrically located to both oxygen atoms of the carboxyl group of each molecule, in which their total s.o.f. will be 1. In the final refinement, the values of the s.o.f. 's were determined [0.74 (5) for O1 and 0.26 (5) for O2 in molecule IA, 0.16 (6) for O3 and 0.86 (6) for O4 in molecule IB and 0.75 (5) for O5 and 0.25 (5) for O6 in molecule IC]. Then, via the only OH H atoms with the high s.o.f.'s, the refinement process was maintained. Unlike the other two molecules, in the molecule B of the three molecules in the asymmetric unit, the OH H atom is located to the O4(HO4) atom in the opposite direction of the –NHCH3 group.

Figures

Fig. 1.
View of the three molecules in the asymmetric unit of the title compound with numbering scheme and thermal ellipsoids drawn at 30% probability.
Fig. 2.
The packing diagram and hydrogen bonding of compound (I) viewed down a axis.
Fig. 3.
View of the packing of (I) viewed down c axis.

Crystal data

C8H9NO2F(000) = 960
Mr = 151.16Dx = 1.306 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ynCell parameters from 2063 reflections
a = 5.0456 (3) Åθ = 3.5–70.5°
b = 36.339 (2) ŵ = 0.78 mm1
c = 12.6496 (5) ÅT = 296 K
β = 96.129 (4)°Prism, colourless
V = 2306.1 (2) Å30.11 × 0.08 × 0.06 mm
Z = 12

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini CCD detector2680 reflections with I > 2σ(I)
Radiation source: Enhance (Cu) X-ray SourceRint = 0.043
graphiteθmax = 70.9°, θmin = 3.7°
Detector resolution: 10.2673 pixels mm-1h = −6→4
ω scansk = −42→43
7671 measured reflectionsl = −15→14
4266 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.1482P)2] where P = (Fo2 + 2Fc2)/3
4266 reflections(Δ/σ)max < 0.001
301 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)

xyzUiso*/Ueq
O1−0.5205 (5)0.12626 (7)−0.07946 (17)0.0620 (8)
O2−0.5929 (5)0.14715 (7)0.08094 (18)0.0641 (8)
N10.3153 (6)0.02834 (8)0.2055 (2)0.0596 (10)
C1−0.4683 (6)0.12683 (9)0.0238 (3)0.0507 (10)
C2−0.2579 (6)0.10184 (9)0.0690 (2)0.0492 (10)
C3−0.1092 (7)0.08070 (9)0.0043 (3)0.0539 (10)
C40.0835 (6)0.05678 (9)0.0485 (2)0.0530 (10)
C50.1363 (6)0.05280 (9)0.1578 (2)0.0487 (9)
C6−0.0136 (7)0.07442 (10)0.2229 (2)0.0580 (10)
C7−0.2032 (7)0.09828 (10)0.1783 (3)0.0598 (11)
C80.4803 (7)0.00493 (10)0.1470 (3)0.0631 (12)
O30.2287 (4)0.02308 (6)0.44193 (16)0.0521 (7)
O40.1669 (5)0.02371 (7)0.61435 (17)0.0598 (8)
N21.0422 (6)0.14849 (8)0.6220 (2)0.0591 (10)
C90.2865 (6)0.03502 (8)0.5326 (2)0.0459 (9)
C100.4885 (6)0.06362 (8)0.5575 (2)0.0444 (9)
C110.6396 (6)0.07621 (9)0.4797 (2)0.0477 (9)
C120.8277 (6)0.10371 (8)0.4994 (2)0.0475 (9)
C130.8671 (6)0.12006 (8)0.6004 (2)0.0470 (9)
C140.7175 (6)0.10686 (9)0.6793 (2)0.0514 (10)
C150.5309 (6)0.07949 (9)0.6592 (2)0.0518 (10)
C161.2134 (7)0.16264 (10)0.5479 (3)0.0610 (11)
O50.9848 (5)0.18634 (7)1.01396 (17)0.0577 (8)
O61.0807 (4)0.17171 (6)0.85095 (17)0.0574 (8)
N30.1885 (6)0.29613 (8)0.7547 (2)0.0628 (10)
C170.9450 (6)0.18920 (9)0.9107 (2)0.0484 (10)
C180.7373 (6)0.21582 (8)0.8699 (3)0.0491 (10)
C190.5713 (6)0.23242 (9)0.9371 (3)0.0516 (10)
C200.3868 (6)0.25830 (9)0.8989 (3)0.0536 (10)
C210.3610 (6)0.26915 (9)0.7929 (2)0.0507 (10)
C220.5231 (7)0.25154 (9)0.7247 (3)0.0585 (11)
C230.7058 (7)0.22514 (9)0.7627 (3)0.0569 (11)
C240.0149 (7)0.31542 (10)0.8198 (3)0.0652 (12)
H10.331200.026700.273700.0720*
HO1−0.637700.14130−0.097700.0930*
H3A−0.140700.08280−0.069300.0650*
H40.180400.043000.004100.0630*
H60.017000.072400.296500.0690*
H7−0.298100.112500.222400.0720*
H8A0.36910−0.011700.103200.0950*
H8B0.60030−0.008800.196000.0950*
H8C0.580800.019800.102900.0950*
H21.050100.158500.683800.0710*
HO40.037500.011100.593100.0900*
H110.613700.065900.412100.0570*
H120.927800.111400.445800.0570*
H140.745100.116900.747200.0620*
H150.432700.071500.713000.0620*
H16A1.329400.143400.528400.0910*
H16B1.318100.182500.580300.0910*
H16C1.107100.171400.485600.0910*
H30.182700.302000.688600.0750*
HO51.108000.172001.030200.0870*
H190.585500.225901.008600.0620*
H200.276600.268800.945100.0640*
H220.507200.257700.653000.0700*
H230.808900.213500.716100.0680*
H24A−0.096900.298000.851000.0980*
H24B−0.094200.332500.776500.0980*
H24C0.120500.328600.875000.0980*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0639 (15)0.0705 (16)0.0507 (12)0.0160 (12)0.0017 (11)0.0032 (11)
O20.0620 (14)0.0708 (16)0.0587 (13)0.0156 (12)0.0035 (11)−0.0050 (12)
N10.0614 (16)0.0710 (19)0.0462 (14)0.0174 (14)0.0046 (12)0.0048 (13)
C10.0458 (16)0.0541 (18)0.0525 (17)0.0004 (14)0.0061 (14)0.0050 (15)
C20.0448 (16)0.0522 (18)0.0513 (16)0.0043 (13)0.0080 (13)0.0014 (14)
C30.0555 (18)0.061 (2)0.0451 (15)0.0011 (15)0.0054 (14)0.0020 (15)
C40.0520 (17)0.058 (2)0.0495 (17)0.0081 (15)0.0079 (14)−0.0025 (15)
C50.0414 (15)0.0537 (18)0.0513 (16)−0.0015 (13)0.0062 (13)0.0029 (14)
C60.0600 (19)0.071 (2)0.0428 (15)0.0112 (17)0.0052 (14)0.0001 (15)
C70.062 (2)0.066 (2)0.0512 (18)0.0112 (17)0.0053 (15)−0.0032 (16)
C80.064 (2)0.065 (2)0.060 (2)0.0114 (17)0.0052 (16)0.0013 (17)
O30.0541 (12)0.0559 (13)0.0456 (11)−0.0049 (10)0.0020 (9)0.0007 (10)
O40.0584 (14)0.0741 (17)0.0470 (12)−0.0168 (12)0.0063 (10)0.0013 (11)
N20.0625 (17)0.0565 (17)0.0594 (16)−0.0091 (13)0.0113 (13)−0.0141 (13)
C90.0434 (15)0.0498 (17)0.0443 (15)0.0059 (13)0.0034 (13)0.0060 (13)
C100.0426 (15)0.0470 (16)0.0434 (15)0.0029 (12)0.0041 (12)0.0026 (13)
C110.0485 (16)0.0497 (17)0.0451 (15)0.0030 (13)0.0061 (13)−0.0054 (13)
C120.0429 (15)0.0536 (18)0.0477 (16)−0.0006 (13)0.0127 (13)−0.0019 (14)
C130.0446 (15)0.0448 (16)0.0509 (16)0.0028 (12)0.0024 (13)0.0003 (13)
C140.0584 (18)0.0542 (19)0.0417 (15)−0.0022 (15)0.0057 (14)−0.0034 (14)
C150.0549 (18)0.0575 (19)0.0438 (15)−0.0017 (15)0.0092 (13)0.0025 (14)
C160.0547 (19)0.056 (2)0.073 (2)−0.0041 (16)0.0097 (17)0.0014 (17)
O50.0566 (14)0.0633 (15)0.0522 (12)0.0102 (11)0.0010 (10)0.0001 (11)
O60.0572 (13)0.0593 (14)0.0545 (12)0.0078 (11)0.0009 (10)−0.0070 (11)
N30.0596 (17)0.0620 (18)0.0664 (17)0.0113 (14)0.0054 (14)0.0139 (15)
C170.0451 (16)0.0451 (17)0.0535 (17)−0.0046 (13)−0.0010 (14)−0.0052 (14)
C180.0428 (16)0.0458 (17)0.0568 (17)−0.0044 (13)−0.0030 (14)−0.0016 (14)
C190.0511 (17)0.0518 (18)0.0510 (17)−0.0050 (14)0.0017 (14)0.0050 (14)
C200.0451 (16)0.0545 (19)0.0606 (18)−0.0004 (14)0.0030 (14)−0.0015 (15)
C210.0442 (16)0.0481 (17)0.0591 (18)−0.0035 (13)0.0022 (14)0.0003 (14)
C220.064 (2)0.057 (2)0.0528 (18)0.0046 (16)−0.0019 (16)0.0018 (15)
C230.0602 (19)0.056 (2)0.0529 (18)0.0052 (15)−0.0007 (15)−0.0076 (15)
C240.055 (2)0.059 (2)0.080 (2)0.0056 (16)−0.0002 (18)0.0012 (18)

Geometric parameters (Å, °)

O1—C11.305 (4)C8—H8C0.9600
O2—C11.249 (4)C8—H8A0.9600
O1—HO10.8200C9—C101.466 (4)
O3—C91.232 (3)C10—C111.385 (4)
O4—C91.318 (4)C10—C151.405 (4)
O4—HO40.8200C11—C121.382 (4)
O5—C171.304 (3)C12—C131.404 (4)
O6—C171.247 (4)C13—C141.399 (4)
O5—HO50.8200C14—C151.375 (4)
N1—C81.448 (5)C11—H110.9300
N1—C51.361 (4)C12—H120.9300
N1—H10.8600C14—H140.9300
N2—C161.436 (5)C15—H150.9300
N2—C131.368 (4)C16—H16C0.9600
N2—H20.8600C16—H16B0.9600
N3—C241.446 (5)C16—H16A0.9600
N3—C211.365 (4)C17—C181.478 (4)
N3—H30.8600C18—C231.390 (5)
C1—C21.466 (4)C18—C191.393 (5)
C2—C31.398 (5)C19—C201.374 (5)
C2—C71.387 (5)C20—C211.390 (5)
C3—C41.378 (5)C21—C221.405 (5)
C4—C51.387 (4)C22—C231.381 (5)
C5—C61.414 (4)C19—H190.9300
C6—C71.368 (5)C20—H200.9300
C3—H3A0.9300C22—H220.9300
C4—H40.9300C23—H230.9300
C6—H60.9300C24—H24A0.9600
C7—H70.9300C24—H24B0.9600
C8—H8B0.9600C24—H24C0.9600
O1···O6i2.678 (3)C20···H24Aviii3.0900
O1···C17ii3.290 (4)C20···H24A2.8400
O2···C24iii3.305 (4)C20···H16Cxv2.9500
O2···O5i2.627 (4)C20···H24C2.8900
O2···C17i3.367 (4)C21···H24Aviii2.9500
O2···N3iii3.229 (4)C22···H24Aviii2.9000
O3···C9iv3.221 (4)C23···H24Aviii3.0000
O3···C9v3.391 (4)C24···H7ix3.0900
O3···N13.074 (3)C24···H202.5800
O3···O4v2.661 (3)H1···O32.2500
O4···O3v2.661 (3)H1···H62.3300
O5···C1vi3.159 (4)H1···H112.5700
O5···C2vi3.405 (4)HO1···O6i1.8600
O5···O2vii2.627 (4)HO1···C17i2.7400
O6···N23.003 (3)HO1···HO5i2.4400
O6···C19viii3.407 (4)H2···O62.1600
O6···C1vii3.400 (4)H2···H232.4000
O6···O1vii2.678 (3)H2···H142.3600
O1···H14ii2.7100HO4···HO4v2.4800
O1···H3A2.4800HO4···O3v1.8500
O2···HO5i1.8200HO4···C9v2.7300
O2···H24Biii2.5800H3···O5iii2.8500
O2···H72.5400H3···H19iii2.4900
O2···H3iii2.6100H3···H222.3700
O3···H62.7100H3···O2ix2.6100
O3···H112.5500HO5···HO1vii2.4400
O3···H12.2500HO5···O2vii1.8200
O3···HO4v1.8500HO5···C1vii2.7000
O4···H152.4500H3A···O12.4800
O4···H8Biv2.6100H4···H8C2.4100
O5···H3ix2.8500H4···H8A2.4800
O5···H22ix2.6800H4···C82.6200
O5···H192.4700H6···O32.7100
O6···H232.5700H6···H12.3300
O6···H22.1600H6···C12x3.0500
O6···HO1vii1.8600H6···H12x2.4400
O6···H142.8400H7···O22.5400
N1···O33.074 (3)H7···C24iii3.0900
N2···O63.003 (3)H8A···C42.9200
N3···O2ix3.229 (4)H8A···C3xiii3.0800
N2···H232.9500H8A···H42.4800
C1···O6i3.400 (4)H8B···O4iv2.6100
C1···C4x3.441 (4)H8B···H15iv2.5700
C1···O5ii3.159 (4)H8C···H42.4100
C1···C17ii3.489 (4)H8C···C4viii3.0100
C2···O5ii3.405 (4)H8C···C42.8600
C4···C1viii3.441 (4)H8C···C5viii3.0600
C9···C9iv3.490 (4)H8C···C3viii3.0500
C9···O3iv3.221 (4)H11···H12.5700
C9···C11x3.588 (4)H11···O32.5500
C9···C12x3.400 (4)H12···H16C2.3900
C9···O3v3.391 (4)H12···C162.6100
C11···C9viii3.588 (4)H12···H16A2.4700
C12···C9viii3.400 (4)H12···H6viii2.4400
C14···C16x3.527 (5)H14···O1vi2.7100
C16···C14viii3.527 (5)H14···H22.3600
C16···C24xi3.495 (5)H14···O62.8400
C17···C19viii3.513 (4)H15···O42.4500
C17···C20viii3.372 (4)H15···H8Biv2.5700
C17···C1vi3.489 (4)H16A···C11viii3.0000
C17···O2vii3.367 (4)H16A···C122.9000
C17···O1vi3.290 (4)H16A···C10viii3.0200
C19···C17x3.513 (4)H16A···C13viii2.9000
C19···O6x3.407 (4)H16A···C14viii2.9100
C20···C17x3.372 (4)H16A···C12viii2.9600
C22···C24viii3.515 (5)H16A···H122.4700
C24···C22x3.515 (5)H16A···C15viii2.9700
C24···O2ix3.305 (4)H16C···C20xiv2.9500
C24···C16xii3.495 (5)H16C···H122.3900
C1···HO5i2.7000H16C···C122.8500
C3···H8Cx3.0500H19···O52.4700
C3···H8Axiii3.0800H19···H3ix2.4900
C4···H8A2.9200H20···C242.5800
C4···H8C2.8600H20···H24A2.3700
C4···H8Cx3.0100H20···H24C2.4500
C5···H8Cx3.0600H22···H32.3700
C8···H42.6200H22···O5iii2.6800
C9···HO4v2.7300H23···O62.5700
C10···H16Ax3.0200H23···N22.9500
C11···H16Ax3.0000H23···H22.4000
C12···H16C2.8500H24A···C20x3.0900
C12···H6viii3.0500H24A···C202.8400
C12···H16A2.9000H24A···C21x2.9500
C12···H16Ax2.9600H24A···C22x2.9000
C12···H24Cxiv3.0400H24A···C23x3.0000
C13···H16Ax2.9000H24A···H202.3700
C14···H16Ax2.9100H24B···O2ix2.5800
C15···H16Ax2.9700H24C···C202.8900
C16···H122.6100H24C···H202.4500
C17···HO1vii2.7400H24C···C12xv3.0400
C1—O1—HO1109.00C12—C13—C14118.0 (3)
C9—O4—HO4109.00N2—C13—C14120.2 (2)
C17—O5—HO5109.00N2—C13—C12121.8 (3)
C5—N1—C8123.2 (3)C13—C14—C15121.8 (2)
C5—N1—H1118.00C10—C15—C14120.0 (3)
C8—N1—H1118.00C12—C11—H11119.00
C13—N2—C16124.1 (3)C10—C11—H11119.00
C16—N2—H2118.00C11—C12—H12120.00
C13—N2—H2118.00C13—C12—H12120.00
C21—N3—C24123.3 (3)C13—C14—H14119.00
C24—N3—H3118.00C15—C14—H14119.00
C21—N3—H3118.00C10—C15—H15120.00
O1—C1—C2116.2 (3)C14—C15—H15120.00
O1—C1—O2121.9 (3)N2—C16—H16B109.00
O2—C1—C2121.9 (3)N2—C16—H16C109.00
C1—C2—C7120.4 (3)H16A—C16—H16B110.00
C3—C2—C7118.1 (3)H16A—C16—H16C109.00
C1—C2—C3121.6 (3)N2—C16—H16A109.00
C2—C3—C4120.6 (3)H16B—C16—H16C110.00
C3—C4—C5121.5 (3)O6—C17—C18122.5 (3)
N1—C5—C4123.9 (3)O5—C17—C18115.4 (3)
N1—C5—C6118.4 (2)O5—C17—O6122.1 (3)
C4—C5—C6117.7 (3)C17—C18—C19121.4 (3)
C5—C6—C7120.4 (3)C17—C18—C23120.2 (3)
C2—C7—C6121.8 (3)C19—C18—C23118.4 (3)
C4—C3—H3A120.00C18—C19—C20120.7 (3)
C2—C3—H3A120.00C19—C20—C21121.6 (3)
C3—C4—H4119.00N3—C21—C22120.1 (3)
C5—C4—H4119.00N3—C21—C20122.4 (3)
C7—C6—H6120.00C20—C21—C22117.5 (3)
C5—C6—H6120.00C21—C22—C23120.9 (3)
C6—C7—H7119.00C18—C23—C22120.8 (3)
C2—C7—H7119.00C18—C19—H19120.00
H8A—C8—H8C109.00C20—C19—H19120.00
H8A—C8—H8B110.00C19—C20—H20119.00
H8B—C8—H8C109.00C21—C20—H20119.00
N1—C8—H8A109.00C21—C22—H22120.00
N1—C8—H8C110.00C23—C22—H22119.00
N1—C8—H8B109.00C18—C23—H23120.00
O3—C9—C10122.7 (2)C22—C23—H23120.00
O3—C9—O4122.6 (3)N3—C24—H24A109.00
O4—C9—C10114.8 (2)N3—C24—H24B109.00
C11—C10—C15118.3 (3)N3—C24—H24C109.00
C9—C10—C15121.5 (3)H24A—C24—H24B110.00
C9—C10—C11120.3 (2)H24A—C24—H24C110.00
C10—C11—C12122.0 (2)H24B—C24—H24C109.00
C11—C12—C13119.9 (3)
C8—N1—C5—C43.1 (5)C9—C10—C15—C14−178.5 (3)
C8—N1—C5—C6−179.7 (3)C9—C10—C11—C12178.5 (3)
C16—N2—C13—C14176.8 (3)C15—C10—C11—C12−0.2 (5)
C16—N2—C13—C12−4.4 (5)C11—C10—C15—C140.3 (5)
C24—N3—C21—C20−1.0 (5)C10—C11—C12—C13−0.9 (5)
C24—N3—C21—C22179.8 (3)C11—C12—C13—C141.9 (4)
O2—C1—C2—C74.4 (5)C11—C12—C13—N2−177.0 (3)
O1—C1—C2—C7−174.7 (3)N2—C13—C14—C15177.0 (3)
O2—C1—C2—C3−176.4 (3)C12—C13—C14—C15−1.9 (5)
O1—C1—C2—C34.6 (5)C13—C14—C15—C100.8 (5)
C7—C2—C3—C40.8 (5)O5—C17—C18—C19−8.9 (4)
C1—C2—C7—C6178.1 (3)O5—C17—C18—C23170.4 (3)
C1—C2—C3—C4−178.5 (3)O6—C17—C18—C19173.9 (3)
C3—C2—C7—C6−1.2 (5)O6—C17—C18—C23−6.9 (5)
C2—C3—C4—C50.1 (5)C17—C18—C19—C20177.2 (3)
C3—C4—C5—C6−0.5 (5)C23—C18—C19—C20−2.1 (5)
C3—C4—C5—N1176.8 (3)C17—C18—C23—C22−176.2 (3)
C4—C5—C6—C70.0 (5)C19—C18—C23—C223.1 (5)
N1—C5—C6—C7−177.4 (3)C18—C19—C20—C21−0.8 (5)
C5—C6—C7—C20.9 (5)C19—C20—C21—N3−176.6 (3)
O4—C9—C10—C11176.1 (3)C19—C20—C21—C222.6 (5)
O4—C9—C10—C15−5.2 (4)N3—C21—C22—C23177.6 (3)
O3—C9—C10—C15173.2 (3)C20—C21—C22—C23−1.7 (5)
O3—C9—C10—C11−5.5 (5)C21—C22—C23—C18−1.2 (5)

Symmetry codes: (i) x−2, y, z−1; (ii) x−1, y, z−1; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1, −y, −z+1; (v) −x, −y, −z+1; (vi) x+1, y, z+1; (vii) x+2, y, z+1; (viii) x+1, y, z; (ix) x+1/2, −y+1/2, z+1/2; (x) x−1, y, z; (xi) x+3/2, −y+1/2, z−1/2; (xii) x−3/2, −y+1/2, z+1/2; (xiii) −x, −y, −z; (xiv) x+1/2, −y+1/2, z−1/2; (xv) x−1/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O30.862.253.074 (3)161
O1—HO1···O6i0.821.862.678 (3)174
N2—H2···O60.862.163.003 (3)168
O4—HO4···O3v0.821.852.661 (3)171
O5—HO5···O2vii0.821.822.627 (4)170
C24—H24B···O2ix0.962.583.305 (4)132
C8—H8C···Cg1viii0.962.763.564 (4)142
C16—H16A···Cg2viii0.962.613.482 (4)151
C24—H24A···Cg3x0.962.703.572 (4)150

Symmetry codes: (i) x−2, y, z−1; (v) −x, −y, −z+1; (vii) x+2, y, z+1; (ix) x+1/2, −y+1/2, z+1/2; (viii) x+1, y, z; (x) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2564).

References

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