5-Diethyl­amino-2-[(Z)-(4-methyl-3-nitro­phen­yl)imino­meth­yl]phenol

In the crystal structure of the title compound, C₁₈H₂₁N₃O₃, the mol­ecular conformation is stabilized by an intra­molecular O—H...N hydrogen bond. The dihedral angle between the two aromatic rings is 3.97 (12)°. The nitro group is almost coplanar with the aromatic ring to which it is attached [dihedral angle = 6.3 (4)°].

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.066
• wR factor = 0.192
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.839
            Test value =      0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       0.84 e/A   
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N21    -   C23'    ..      11.77 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        N21
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C23'

Alert level C
DIFMN02_ALERT_2_C  The minimum difference density is < -0.1*ZMAX*0.75
            _refine_diff_density_min given =     -0.655
            Test value =     -0.600
DIFMN03_ALERT_1_C  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............      -0.65 e/A   
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9

   0 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

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S1. Comment

Schiff bases are used as substrates in the preparation of a number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. They are also used as substrates in the preparation of number of biologically active compounds (Siddiqui et al., 2006). Some Schiff base derivatives are also known to have activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh & Dash, 1988; Varma et al., 1986), antitumor (Hodnett & Dunn, 1970; Misra et al., 1981; Agarwal et al., 1983) and as herbicides (Samadhiya & Halve, 2001). The crystal structures of (E)-2-hydroxy-5-methyl-3-[(4-methyl-2 pyridyl)iminomethyl] benzaldehyde (Büyükgüngör et al., 2007); (E)-2-hydroxy-5-methyl-3-[(2-pyridylimino) methyl]benzaldehyde Odabaşoğlu et al. (2007).

1-(4-{[(E)-(4-diethylamino-2-hydroxy phenyl)methylene]amino}phenyl)ethanone (Yathirajan et al. (2007), 2-{(E)-[(2-chloro-5-nitrophenyl)imino]methyl}-5-(diethylamino)phenol (Butcher et al., 2007), 2-bromo-N'-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate (Narayana et al., 2007), 2-bromo-N'-isopropylidene-5-methoxybenzohydrazide (Sarojini et al., 2007) have been reported. As a part of our ongoing investigations on the synthesis and structure of Schiff bases, we have determined the structure of the title compound (I).

In the structure of the title compound the oxazine ring adopts a half-chair conformation. The molecular conformation is stabilized by an intramolecular O—H···N hydroggen bond. The dihedral angle between the two aromatic rings is 3.97 (12) Å. The nitro groups is almost co planar with the aromatic ring to which it is attached [dihedral angle 6.3 (4)°].

Related literature

For related literature, see: Agarwal et al. (1983); Butcher et al. (2007); Büyükgüngör et al. (2007); El-Masry et al. (2000); Hodnett & Dunn (1970); Misra et al. (1981); Narayana et al. (2007); Odabaşoğlu et al. (2007); Pandey et al. (1999); Samadhiya & Halve (2001); Sarojini et al. (2007); Siddiqui et al. (2006); Singh & Dash (1988); Varma et al. (1986); Yathirajan et al. (2007).

S2. Experimental

A mixture of 4-methyl-3-nitroaniline (1.52 g, 0.01 mol) and 4-(diethylamino)-2-hydroxybenzaldehyde (1.93 g, 0.01 mol) in 35 ml of ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 9 h. On cooling, a solid separated. It was filtered off and recrystallized from acetone (m.p.: 403–407 K). Analysis found: C 65.98, H 6.41, N 12.78%; C₁₈H₂₁N₃O₃ requires: C 66.04, H 6.47, N 12.84%.

S3. Refinement

H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 U_eq(C) or U(H) = 1.5 U_eq(C_methyl)] using a riding model with C—H ranging from 0.95 Å to 0.99 Å. The methyl group bonded to the aromatic ring was allowed to rotate but not to tip. The hydroxyl H atom was freely refined. One of the ethyl chains is disordered over two sites with a site occupation factor of 0.602 (7) for the major occupied site. The bond lengths and angles of the disordered groups were restrained to have the same values as the non-disordered one.

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures

Fig. 1. Perspective view of the title compound with the atom numbering scheme and displacement ellipsoids drawn at the 50% probability level. The minor occupied site of the disordered ethyl chain is drawn with open bonds. The intramolecular hydrogen bond is shown as a dashed line.

5-Diethylamino-2-[(Z)-(4-methyl-3-nitrophenyl)iminomethyl]phenol

Crystal data

C18H21N3O3	F(000) = 696
Mr = 327.38	Dx = 1.316 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.3157 (4) Å	Cell parameters from 32963 reflections
b = 22.3708 (10) Å	θ = 2.8–27.5°
c = 10.3849 (6) Å	µ = 0.09 mm^−1
β = 103.571 (5)°	T = 173 K
V = 1652.12 (15) Å^3	Block, orange
Z = 4	0.41 × 0.37 × 0.33 mm

Data collection

STOE IPDS II two-circle- diffractometer	3334 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 27.6°, θmin = 2.7°
ω scans	h = −9→9
34345 measured reflections	k = −29→28
3823 independent reflections	l = −13→12

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 atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.192	w = 1/[σ^2(Fo^2) + (0.1026P)^2 + 1.2402P] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
3823 reflections	Δρmax = 0.84 e Å^−3
242 parameters	Δρmin = −0.66 e Å^−3
9 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.055 (7)

Special details

Experimental. ;

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.38176 (19)	0.59715 (6)	0.59143 (14)	0.0370 (3)
H1	0.322 (5)	0.5734 (15)	0.526 (3)	0.081 (10)*
O2	0.0769 (3)	0.39185 (11)	−0.12486 (19)	0.0797 (7)
O3	0.3429 (2)	0.43512 (10)	−0.05554 (17)	0.0634 (5)
N1	0.3258 (2)	0.53706 (7)	0.37122 (14)	0.0319 (3)
N2	0.1885 (2)	0.41980 (8)	−0.04052 (16)	0.0422 (4)
C1	0.2115 (2)	0.49854 (8)	0.27839 (17)	0.0313 (4)
C2	0.2568 (2)	0.47627 (8)	0.16421 (17)	0.0319 (4)
H2	0.3738	0.4860	0.1448	0.038*
C3	0.1293 (2)	0.43970 (8)	0.07904 (17)	0.0331 (4)
C4	−0.0456 (3)	0.42242 (9)	0.10075 (18)	0.0363 (4)
C5	−0.0846 (3)	0.44508 (10)	0.2170 (2)	0.0429 (5)
H5	−0.2005	0.4348	0.2377	0.051*
C6	0.0388 (3)	0.48186 (9)	0.30300 (19)	0.0400 (4)
H6	0.0054	0.4961	0.3806	0.048*
C7	−0.1915 (3)	0.38345 (10)	0.0125 (2)	0.0460 (5)
H7A	−0.2978	0.3776	0.0536	0.069*
H7B	−0.1358	0.3446	0.0005	0.069*
H7C	−0.2355	0.4029	−0.0738	0.069*
C8	0.4853 (2)	0.55697 (8)	0.35579 (16)	0.0314 (4)
H8	0.5288	0.5445	0.2808	0.038*
C11	0.5982 (2)	0.59736 (7)	0.44885 (16)	0.0303 (4)
C12	0.5429 (2)	0.61720 (7)	0.56401 (16)	0.0289 (4)
C13	0.6516 (3)	0.65743 (8)	0.65132 (18)	0.0336 (4)
H13	0.6094	0.6708	0.7262	0.040*
C14	0.8232 (3)	0.67875 (10)	0.6305 (2)	0.0485 (6)
C15	0.8784 (3)	0.65861 (11)	0.5147 (2)	0.0545 (6)
H15	0.9933	0.6723	0.4976	0.065*
C16	0.7681 (3)	0.61986 (9)	0.42803 (19)	0.0413 (5)
H16	0.8078	0.6078	0.3512	0.050*
N21	0.9350 (3)	0.71679 (12)	0.7186 (2)	0.0826 (9)
C21	0.8793 (3)	0.74053 (10)	0.8340 (2)	0.0443 (5)
H21A	0.9936	0.7539	0.8991	0.053*
H21B	0.8223	0.7078	0.8756	0.053*
C22	0.7429 (4)	0.79165 (10)	0.8061 (3)	0.0570 (6)
H22A	0.7130	0.8047	0.8889	0.086*
H22B	0.6275	0.7787	0.7437	0.086*
H22C	0.7992	0.8249	0.7676	0.086*
C23	1.1389 (6)	0.72798 (15)	0.7141 (3)	0.0403 (10)	0.602 (7)
H23A	1.2166	0.7372	0.8035	0.048*	0.602 (7)
H23B	1.1925	0.6927	0.6787	0.048*	0.602 (7)
C24	1.1300 (7)	0.78111 (17)	0.6227 (4)	0.0508 (11)	0.602 (7)
H24A	1.2571	0.7911	0.6143	0.076*	0.602 (7)
H24B	1.0761	0.8154	0.6594	0.076*	0.602 (7)
H24C	1.0511	0.7712	0.5353	0.076*	0.602 (7)
C23'	1.0482 (7)	0.7645 (2)	0.6538 (5)	0.0332 (13)	0.398 (7)
H23C	1.0022	0.7664	0.5563	0.040*	0.398 (7)
H23D	1.0447	0.8048	0.6922	0.040*	0.398 (7)
C24'	1.2430 (8)	0.7363 (3)	0.6948 (6)	0.0449 (15)	0.398 (7)
H24D	1.3333	0.7610	0.6621	0.067*	0.398 (7)
H24E	1.2396	0.6961	0.6569	0.067*	0.398 (7)
H24F	1.2813	0.7338	0.7916	0.067*	0.398 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0384 (7)	0.0395 (7)	0.0379 (7)	−0.0090 (5)	0.0184 (6)	−0.0085 (6)
O2	0.0791 (13)	0.1144 (17)	0.0515 (10)	−0.0434 (12)	0.0274 (9)	−0.0426 (11)
O3	0.0452 (9)	0.0981 (14)	0.0518 (9)	−0.0122 (9)	0.0212 (7)	−0.0298 (9)
N1	0.0352 (8)	0.0312 (7)	0.0286 (7)	0.0030 (6)	0.0062 (6)	−0.0011 (6)
N2	0.0437 (9)	0.0513 (10)	0.0318 (8)	−0.0039 (7)	0.0089 (7)	−0.0086 (7)
C1	0.0333 (8)	0.0316 (8)	0.0277 (8)	0.0048 (6)	0.0048 (6)	0.0006 (6)
C2	0.0306 (8)	0.0351 (9)	0.0296 (8)	0.0027 (7)	0.0064 (6)	0.0007 (7)
C3	0.0353 (9)	0.0373 (9)	0.0256 (8)	0.0035 (7)	0.0051 (7)	−0.0004 (7)
C4	0.0340 (9)	0.0396 (10)	0.0331 (9)	−0.0006 (7)	0.0034 (7)	0.0012 (7)
C5	0.0342 (9)	0.0546 (12)	0.0416 (10)	−0.0046 (8)	0.0125 (8)	−0.0033 (9)
C6	0.0387 (10)	0.0495 (11)	0.0341 (9)	0.0009 (8)	0.0130 (7)	−0.0055 (8)
C7	0.0405 (10)	0.0505 (12)	0.0428 (11)	−0.0081 (9)	0.0016 (8)	−0.0032 (9)
C8	0.0389 (9)	0.0300 (8)	0.0258 (8)	0.0041 (7)	0.0085 (7)	0.0008 (6)
C11	0.0374 (9)	0.0279 (8)	0.0271 (8)	0.0014 (6)	0.0107 (7)	0.0010 (6)
C12	0.0334 (8)	0.0265 (8)	0.0292 (8)	0.0007 (6)	0.0118 (6)	0.0028 (6)
C13	0.0409 (9)	0.0336 (9)	0.0311 (8)	−0.0050 (7)	0.0178 (7)	−0.0050 (7)
C14	0.0539 (12)	0.0533 (12)	0.0470 (11)	−0.0231 (10)	0.0295 (10)	−0.0202 (9)
C15	0.0573 (13)	0.0635 (14)	0.0552 (13)	−0.0289 (11)	0.0382 (11)	−0.0256 (11)
C16	0.0515 (11)	0.0436 (10)	0.0362 (9)	−0.0083 (8)	0.0248 (8)	−0.0083 (8)
N21	0.0802 (15)	0.1071 (19)	0.0811 (16)	−0.0645 (14)	0.0604 (13)	−0.0646 (15)
C21	0.0471 (11)	0.0501 (11)	0.0397 (10)	−0.0118 (9)	0.0181 (8)	−0.0151 (9)
C22	0.0653 (15)	0.0449 (12)	0.0582 (14)	−0.0102 (10)	0.0090 (11)	0.0005 (10)
C23	0.036 (2)	0.0433 (18)	0.0420 (17)	−0.0064 (14)	0.0097 (14)	−0.0062 (14)
C24	0.060 (3)	0.045 (2)	0.053 (2)	−0.0138 (18)	0.0234 (19)	−0.0036 (16)
C23'	0.032 (2)	0.028 (2)	0.043 (3)	−0.0066 (18)	0.017 (2)	−0.0013 (19)
C24'	0.029 (3)	0.052 (3)	0.055 (3)	−0.003 (2)	0.014 (2)	−0.007 (2)

Geometric parameters (Å, º)

O1—C12	1.353 (2)	C14—N21	1.370 (3)
O1—H1	0.89 (3)	C14—C15	1.429 (3)
O2—N2	1.220 (2)	C15—C16	1.368 (3)
O3—N2	1.225 (2)	C15—H15	0.9500
N1—C8	1.294 (2)	C16—H16	0.9500
N1—C1	1.411 (2)	N21—C21	1.454 (3)
N2—C3	1.476 (2)	N21—C23	1.524 (4)
C1—C2	1.396 (2)	N21—C23'	1.593 (6)
C1—C6	1.397 (3)	C21—C22	1.501 (3)
C2—C3	1.391 (2)	C21—H21A	0.9900
C2—H2	0.9500	C21—H21B	0.9900
C3—C4	1.404 (3)	C22—H22A	0.9800
C4—C5	1.399 (3)	C22—H22B	0.9800
C4—C7	1.510 (3)	C22—H22C	0.9800
C5—C6	1.382 (3)	C23—C24	1.513 (5)
C5—H5	0.9500	C23—H23A	0.9900
C6—H6	0.9500	C23—H23B	0.9900
C7—H7A	0.9800	C24—H24A	0.9800
C7—H7B	0.9800	C24—H24B	0.9800
C7—H7C	0.9800	C24—H24C	0.9800
C8—C11	1.435 (2)	C23'—C24'	1.524 (7)
C8—H8	0.9500	C23'—H23C	0.9900
C11—C16	1.404 (3)	C23'—H23D	0.9900
C11—C12	1.420 (2)	C24'—H24D	0.9800
C12—C13	1.388 (2)	C24'—H24E	0.9800
C13—C14	1.406 (3)	C24'—H24F	0.9800
C13—H13	0.9500
C12—O1—H1	109 (2)	C14—C15—H15	119.5
C8—N1—C1	122.18 (15)	C15—C16—C11	122.20 (17)
O2—N2—O3	122.25 (18)	C15—C16—H16	118.9
O2—N2—C3	118.63 (17)	C11—C16—H16	118.9
O3—N2—C3	118.95 (16)	C14—N21—C21	122.56 (18)
C2—C1—C6	117.71 (16)	C14—N21—C23	121.1 (2)
C2—C1—N1	125.28 (16)	C21—N21—C23	115.5 (2)
C6—C1—N1	117.01 (15)	C14—N21—C23'	115.0 (3)
C3—C2—C1	119.52 (16)	C21—N21—C23'	112.2 (2)
C3—C2—H2	120.2	N21—C21—C22	114.9 (2)
C1—C2—H2	120.2	N21—C21—H21A	108.5
C2—C3—C4	124.06 (16)	C22—C21—H21A	108.5
C2—C3—N2	115.27 (16)	N21—C21—H21B	108.5
C4—C3—N2	120.67 (16)	C22—C21—H21B	108.5
C5—C4—C3	114.64 (17)	H21A—C21—H21B	107.5
C5—C4—C7	118.31 (18)	C21—C22—H22A	109.5
C3—C4—C7	127.04 (17)	C21—C22—H22B	109.5
C6—C5—C4	122.57 (18)	H22A—C22—H22B	109.5
C6—C5—H5	118.7	C21—C22—H22C	109.5
C4—C5—H5	118.7	H22A—C22—H22C	109.5
C5—C6—C1	121.49 (17)	H22B—C22—H22C	109.5
C5—C6—H6	119.3	C24—C23—N21	104.5 (3)
C1—C6—H6	119.3	C24—C23—H23A	110.9
C4—C7—H7A	109.5	N21—C23—H23A	110.9
C4—C7—H7B	109.5	C24—C23—H23B	110.9
H7A—C7—H7B	109.5	N21—C23—H23B	110.9
C4—C7—H7C	109.5	H23A—C23—H23B	108.9
H7A—C7—H7C	109.5	C23—C24—H24A	109.5
H7B—C7—H7C	109.5	C23—C24—H24B	109.5
N1—C8—C11	121.82 (16)	H24A—C24—H24B	109.5
N1—C8—H8	119.1	C23—C24—H24C	109.5
C11—C8—H8	119.1	H24A—C24—H24C	109.5
C16—C11—C12	117.06 (16)	H24B—C24—H24C	109.5
C16—C11—C8	120.85 (16)	C24'—C23'—N21	98.7 (4)
C12—C11—C8	122.08 (16)	C24'—C23'—H23C	112.0
O1—C12—C13	118.13 (15)	N21—C23'—H23C	112.0
O1—C12—C11	120.53 (15)	C24'—C23'—H23D	112.0
C13—C12—C11	121.34 (16)	N21—C23'—H23D	112.0
C12—C13—C14	120.99 (16)	H23C—C23'—H23D	109.7
C12—C13—H13	119.5	C23'—C24'—H24D	109.5
C14—C13—H13	119.5	C23'—C24'—H24E	109.5
N21—C14—C13	121.52 (18)	H24D—C24'—H24E	109.5
N21—C14—C15	121.00 (18)	C23'—C24'—H24F	109.5
C13—C14—C15	117.47 (18)	H24D—C24'—H24F	109.5
C16—C15—C14	120.91 (18)	H24E—C24'—H24F	109.5
C16—C15—H15	119.5
C8—N1—C1—C2	2.0 (3)	C8—C11—C12—C13	−178.38 (16)
C8—N1—C1—C6	−177.52 (16)	O1—C12—C13—C14	178.26 (19)
C6—C1—C2—C3	1.1 (3)	C11—C12—C13—C14	−1.7 (3)
N1—C1—C2—C3	−178.46 (16)	C12—C13—C14—N21	−177.6 (2)
C1—C2—C3—C4	−0.8 (3)	C12—C13—C14—C15	1.6 (3)
C1—C2—C3—N2	178.49 (16)	N21—C14—C15—C16	178.9 (3)
O2—N2—C3—C2	−173.9 (2)	C13—C14—C15—C16	−0.3 (4)
O3—N2—C3—C2	1.5 (3)	C14—C15—C16—C11	−0.9 (4)
O2—N2—C3—C4	5.5 (3)	C12—C11—C16—C15	0.8 (3)
O3—N2—C3—C4	−179.13 (19)	C8—C11—C16—C15	179.7 (2)
C2—C3—C4—C5	0.1 (3)	C13—C14—N21—C21	−3.9 (5)
N2—C3—C4—C5	−179.22 (17)	C15—C14—N21—C21	176.9 (3)
C2—C3—C4—C7	179.40 (18)	C13—C14—N21—C23	165.2 (3)
N2—C3—C4—C7	0.1 (3)	C15—C14—N21—C23	−13.9 (5)
C3—C4—C5—C6	0.4 (3)	C13—C14—N21—C23'	−146.3 (3)
C7—C4—C5—C6	−178.99 (19)	C15—C14—N21—C23'	34.6 (4)
C4—C5—C6—C1	−0.1 (3)	C14—N21—C21—C22	−78.8 (3)
C2—C1—C6—C5	−0.6 (3)	C23—N21—C21—C22	111.4 (3)
N1—C1—C6—C5	178.94 (18)	C23'—N21—C21—C22	64.4 (3)
C1—N1—C8—C11	178.33 (15)	C14—N21—C23—C24	90.6 (4)
N1—C8—C11—C16	−178.02 (17)	C21—N21—C23—C24	−99.5 (3)
N1—C8—C11—C12	0.8 (3)	C23'—N21—C23—C24	−3.6 (3)
C16—C11—C12—O1	−179.47 (16)	C14—N21—C23'—C24'	−105.5 (4)
C8—C11—C12—O1	1.6 (3)	C21—N21—C23'—C24'	108.3 (3)
C16—C11—C12—C13	0.5 (3)	C23—N21—C23'—C24'	4.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.89 (3)	1.80 (3)	2.6010 (19)	147 (3)