5-(Diethyl­amino)-2-[(Z)-(1-naphthyl­imino)meth­yl]phenol

In the title mol­ecule, C₂₁H₂₂N₂O, the angle between the mean planes of the 1-naphthyl­imino and 2-methyl­yphenyl groups is 63.3 (2)°. The two diethyl extensions from the 5-diethyl­amino group are twisted in a + and − anti­periplanar conformation. One of the ethyl arms is disordered over two conformations with occupancies of 0.644 (3) and 0.356 (3). The crystal packing is stabilized by inter­molecular C—H...π inter­actions between π orbitals of the 1-naphthyl (I/II) rings and H atoms from a nearby benzene ring as well as from an ethyl C atom of an ethyl­amino group. The mol­ecules are stacked along the b axis in alternate inverted chains with the 1-naphthyl rings obliquely parallel to the ab face of the unit cell. Intra­molecular inter­actions between the hydroxyl H atom and the imino N atom provide additional conformational stability.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.047
• wR factor = 0.129
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.782     1.000
            Tmin(prime) and Tmax expected:      0.965     0.974
            RR(prime) =      0.789
            Please check that your absorption correction is appropriate.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.974
            Tmax scaled      0.974 Tmin scaled      0.761
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           32.52
           From the CIF: _reflns_number_total               3003
           Count of symmetry unique reflns         3276
           Completeness (_total/calc)             91.67%
           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
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

---

S1. Comment

Schiff bases are synthesized from an aromatic amine and a carbonyl compound by nucleophilic addition forming a hemiaminal, followed by a dehydration to generate an imine. Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives are also known to have biological activities such as antimicrobial (El-Masry et al. 2000; Pandey et al. 1999), antifungal (Singh et al. 1988; Varma et al., 1986), antitumor (Hodnett et al. 1970; Misra et al. 1981; Agarwal et al., 1983) and as herbicides (Samadhiya & Halve, 2001). The crysta 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 (Odabasoglu 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) have been reported. A new Schiff base, (I), C₂₁H₂₂N₂O is prepared and its crystal structure is reported.

The angle between the mean planes of the 1-naphthylimino and 2-methylyphenyl groups is 63.3 (2)° (Fig. 1). The two diethyl extensions from the 5-diethylamino group are twisted in a + and - antiperiplanar conformation. One of the ethyl arms C19—C19 is disordered over two conformations which are constrained to have similar metrical parameters with occupancies of 0.644 (3) [C18B & C19B)] and 0.356 (3) [C18A & C19A], respectively. Crystal packing is stabilized by intermolecular C—H···Cg1/Cg2 packing interactions between Cg1/Cg2-π orbitals of the 1-naphthyl (I/II) rings and hydrogen atoms from a nearby phenyl ring [Cg1/Cg2 = center of gravity of the 1-naphthyl (I/II) rings, respectively] as well as between a disordered ethyl carbon from an ethylamino group and Cg1 (Fig. 2). The molecules are stacked along the b axis in alternate, inverted chains with the 1-naphthyl rings obliquely parallel to the ab face of the unit cell (Fig. 3). Intramolecular interactions between the hydroxyl hydrogen atom and the imino nitrogen atom [O1—H10···N1 = 2.6060 (14) Å] in the asymmetric unit provide additional crystal stability.

Related literature

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

S2. Experimental

A mixture of naphthalen-1-amine (1.43 g, 0.01 mol) and 4-(diethylamino)-2-hydroxybenzaldehyde (1.93 g, 0.01 mol) in 30 ml of ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 5 h (Fig. 4). On cooling, the solid separated was filtered and recrystallized from acetone (m.p.: 371–373 K). Analysis found: C 79.11, H 6.89, N 8.72%; C₂₁H₂₂N₂O requires: C 79.21, H 6.96, N 8.80%.

S3. Refinement

In the absence of anomalous scatterers Friedel pairs had been merged. The hydroxyl hydrogen atom (H10) was located in a difference Fourier map and along with all other all other H atoms placed in their calculated positions and then refined using the riding model with O—H = 0.82 Å and C—H = 0.93 to 0.97 Å, and with U_iso(H) = 1.19–1.49U_eq(C, O). Atoms C17 and C18 are disordered with refined occupancies of 0.4267 (14) [A] and 0.5733 (14) [B], respectively.

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

	Fig. 1. Molecular structure of the title compound, showing atom labeling and 50% probability displacement ellipsoids. Atoms C18 and C19 are disordered over two conformations which are constrained to have similar metrical parameters with occupanicies of 0.644 (3) [C18B & C19B)] and 0.356 (3) [C18A & C19A], respectively. Dashed lines indicate intramolecular O1—H10···N1 hydrogen bonds.
	Fig. 2. Packing diagram of the title compound, viewed down the a axis.
	Fig. 3. Packing diagram of the title compound, viewed down the c axis. Dashed lines indicate intramolecular O1—H10···N1 hydrogen bonds.
	Fig. 4. Synthetic scheme for C21H22N2O.

5-(Diethylamino)-2-[(Z)-(1-naphthylimino)methyl]phenol

Crystal data

C21H22N2O	F(000) = 340
Mr = 318.41	Dx = 1.209 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3058 reflections
a = 7.5329 (5) Å	θ = 4.8–32.5°
b = 14.6040 (1) Å	µ = 0.08 mm^−1
c = 7.9904 (5) Å	T = 296 K
β = 95.951 (6)°	Prism, pale yellow
V = 874.29 (10) Å^3	0.47 × 0.42 × 0.35 mm
Z = 2

Data collection

Oxford Diffraction Gemini R CCD diffractometer	3003 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 10.5081 pixels mm^-1	θmax = 32.5°, θmin = 4.8°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −21→21
Tmin = 0.782, Tmax = 1.000	l = −11→11
8501 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0765P)^2] where P = (Fo^2 + 2Fc^2)/3
3003 reflections	(Δ/σ)max = 0.036
228 parameters	Δρmax = 0.23 e Å^−3
1 restraint	Δρmin = −0.22 e Å^−3

Special details

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	0.44021 (13)	0.32600 (7)	0.87995 (13)	0.0690 (3)
H1O	0.3569	0.3617	0.8848	0.083*
N1	0.13393 (14)	0.40391 (7)	0.78988 (14)	0.0514 (3)
N2	0.57713 (17)	0.04299 (9)	0.62685 (14)	0.0650 (4)
C1	0.00190 (15)	0.46814 (9)	0.82282 (15)	0.0465 (3)
C2	−0.16455 (18)	0.44247 (11)	0.86254 (17)	0.0557 (4)
H2A	−0.1983	0.3812	0.8548	0.067*
C3	−0.28310 (18)	0.50751 (11)	0.91432 (17)	0.0597 (4)
H3A	−0.3944	0.4887	0.9420	0.072*
C4	−0.23931 (19)	0.59759 (12)	0.92512 (18)	0.0618 (4)
H4A	−0.3197	0.6398	0.9609	0.074*
C5	−0.06962 (18)	0.62741 (10)	0.88146 (15)	0.0503 (3)
C6	−0.0191 (2)	0.72118 (11)	0.88894 (19)	0.0647 (4)
H6A	−0.0978	0.7647	0.9234	0.078*
C7	0.1446 (2)	0.74816 (11)	0.8459 (2)	0.0677 (5)
H7A	0.1769	0.8096	0.8518	0.081*
C8	0.2618 (2)	0.68327 (11)	0.79346 (18)	0.0621 (4)
H8A	0.3719	0.7020	0.7628	0.074*
C9	0.21839 (18)	0.59312 (10)	0.78615 (17)	0.0528 (4)
H9A	0.2997	0.5510	0.7517	0.063*
C10	0.05183 (17)	0.56224 (9)	0.82993 (14)	0.0448 (3)
C11	0.09765 (17)	0.33416 (9)	0.69144 (16)	0.0502 (3)
H11A	−0.0150	0.3305	0.6321	0.060*
C12	0.22364 (17)	0.26267 (9)	0.67030 (15)	0.0470 (3)
C13	0.39169 (16)	0.25952 (9)	0.76692 (15)	0.0478 (3)
C14	0.50757 (17)	0.18848 (10)	0.75195 (16)	0.0516 (4)
H14A	0.6171	0.1883	0.8174	0.062*
C15	0.46460 (17)	0.11565 (10)	0.63957 (15)	0.0494 (3)
C16	0.29674 (19)	0.12017 (11)	0.53899 (17)	0.0610 (4)
H16A	0.2639	0.0741	0.4616	0.073*
C17	0.18444 (19)	0.19213 (10)	0.55627 (17)	0.0591 (4)
H17A	0.0765	0.1939	0.4883	0.071*
C18A	0.7636 (6)	0.0545 (4)	0.7223 (6)	0.0672 (7)	0.356 (3)
H18A	0.8217	0.1071	0.6778	0.081*	0.356 (3)
H18B	0.7516	0.0662	0.8401	0.081*	0.356 (3)
C19A	0.8621 (6)	−0.0171 (10)	0.7100 (9)	0.187 (3)	0.356 (3)
H19A	0.9649	−0.0136	0.7915	0.280*	0.356 (3)
H19B	0.8999	−0.0200	0.5990	0.280*	0.356 (3)
H19C	0.7947	−0.0711	0.7304	0.280*	0.356 (3)
C18B	0.7214 (3)	0.0213 (2)	0.7592 (3)	0.0672 (7)	0.644 (3)
H18C	0.7000	−0.0386	0.8058	0.081*	0.644 (3)
H18D	0.7214	0.0659	0.8491	0.081*	0.644 (3)
C19B	0.9046 (4)	0.0216 (6)	0.6908 (5)	0.187 (3)	0.644 (3)
H19D	0.9947	0.0035	0.7782	0.280*	0.644 (3)
H19E	0.9303	0.0821	0.6529	0.280*	0.644 (3)
H19F	0.9032	−0.0205	0.5984	0.280*	0.644 (3)
C20	0.5237 (2)	−0.03633 (11)	0.52343 (19)	0.0613 (4)
H20A	0.6303	−0.0672	0.4942	0.074*
H20B	0.4581	−0.0153	0.4197	0.074*
C21	0.4101 (3)	−0.10460 (16)	0.6054 (3)	0.1049 (7)
H21A	0.3791	−0.1541	0.5289	0.157*
H21B	0.3033	−0.0751	0.6337	0.157*
H21C	0.4756	−0.1281	0.7058	0.157*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0547 (5)	0.0600 (6)	0.0886 (7)	−0.0032 (5)	−0.0097 (5)	−0.0216 (6)
N1	0.0516 (5)	0.0430 (6)	0.0596 (6)	−0.0019 (5)	0.0053 (5)	0.0035 (5)
N2	0.0665 (7)	0.0656 (8)	0.0596 (6)	0.0245 (6)	−0.0088 (6)	−0.0160 (6)
C1	0.0457 (6)	0.0477 (7)	0.0455 (6)	0.0015 (6)	0.0024 (5)	0.0017 (6)
C2	0.0539 (7)	0.0546 (8)	0.0587 (7)	−0.0051 (6)	0.0060 (6)	0.0070 (6)
C3	0.0477 (7)	0.0759 (10)	0.0560 (7)	−0.0026 (7)	0.0078 (6)	−0.0003 (7)
C4	0.0571 (7)	0.0722 (10)	0.0568 (7)	0.0105 (8)	0.0089 (6)	−0.0107 (7)
C5	0.0581 (7)	0.0513 (7)	0.0416 (6)	0.0013 (6)	0.0063 (5)	−0.0057 (5)
C6	0.0795 (9)	0.0520 (8)	0.0633 (8)	0.0069 (8)	0.0101 (7)	−0.0139 (7)
C7	0.0882 (10)	0.0440 (7)	0.0707 (9)	−0.0110 (8)	0.0076 (8)	−0.0068 (7)
C8	0.0638 (8)	0.0569 (9)	0.0658 (8)	−0.0109 (8)	0.0082 (7)	−0.0003 (7)
C9	0.0526 (7)	0.0496 (8)	0.0559 (7)	0.0010 (6)	0.0048 (6)	0.0003 (6)
C10	0.0471 (6)	0.0496 (7)	0.0368 (5)	0.0002 (6)	0.0006 (5)	−0.0023 (5)
C11	0.0532 (7)	0.0469 (7)	0.0493 (6)	0.0032 (6)	−0.0010 (5)	0.0041 (6)
C12	0.0514 (6)	0.0430 (7)	0.0454 (6)	0.0007 (6)	−0.0001 (5)	0.0051 (5)
C13	0.0495 (7)	0.0433 (7)	0.0500 (6)	−0.0092 (6)	0.0030 (6)	−0.0043 (6)
C14	0.0429 (6)	0.0588 (8)	0.0518 (7)	−0.0026 (6)	−0.0013 (5)	−0.0021 (6)
C15	0.0494 (7)	0.0522 (8)	0.0464 (6)	0.0020 (6)	0.0045 (5)	−0.0025 (6)
C16	0.0621 (8)	0.0622 (8)	0.0557 (7)	0.0087 (7)	−0.0086 (6)	−0.0145 (7)
C17	0.0571 (7)	0.0624 (9)	0.0536 (7)	0.0105 (7)	−0.0143 (6)	−0.0084 (7)
C18A	0.0683 (12)	0.0760 (17)	0.0551 (11)	0.0169 (12)	−0.0047 (9)	−0.0071 (11)
C19A	0.0287 (12)	0.443 (9)	0.0883 (16)	−0.048 (3)	0.0068 (12)	0.020 (3)
C18B	0.0683 (12)	0.0760 (17)	0.0551 (11)	0.0169 (12)	−0.0047 (9)	−0.0071 (11)
C19B	0.0287 (12)	0.443 (9)	0.0883 (16)	−0.048 (3)	0.0068 (12)	0.020 (3)
C20	0.0633 (7)	0.0632 (9)	0.0583 (8)	0.0090 (8)	0.0102 (6)	−0.0095 (7)
C21	0.1101 (14)	0.0808 (14)	0.1280 (16)	−0.0032 (13)	0.0325 (12)	0.0187 (13)

Geometric parameters (Å, º)

O1—C13	1.3503 (16)	C12—C17	1.3867 (19)
O1—H1O	0.8200	C12—C13	1.4135 (17)
N1—C11	1.2987 (17)	C13—C14	1.3691 (19)
N1—C1	1.4116 (17)	C14—C15	1.4080 (19)
N2—C15	1.3684 (19)	C14—H14A	0.9300
N2—C20	1.455 (2)	C15—C16	1.4277 (19)
N2—C18B	1.470 (3)	C16—C17	1.365 (2)
N2—C18A	1.537 (5)	C16—H16A	0.9300
C1—C2	1.3769 (18)	C17—H17A	0.9300
C1—C10	1.4244 (19)	C18A—C19A	1.293 (13)
C2—C3	1.396 (2)	C18A—H18A	0.9700
C2—H2A	0.9300	C18A—H18B	0.9700
C3—C4	1.357 (2)	C19A—H19A	0.9600
C3—H3A	0.9300	C19A—H19B	0.9600
C4—C5	1.427 (2)	C19A—H19C	0.9600
C4—H4A	0.9300	C18B—C19B	1.536 (4)
C5—C10	1.4108 (19)	C18B—H18C	0.9700
C5—C6	1.421 (2)	C18B—H18D	0.9700
C6—C7	1.371 (2)	C19B—H19D	0.9600
C6—H6A	0.9300	C19B—H19E	0.9600
C7—C8	1.389 (2)	C19B—H19F	0.9600
C7—H7A	0.9300	C20—C21	1.507 (3)
C8—C9	1.356 (2)	C20—H20A	0.9700
C8—H8A	0.9300	C20—H20B	0.9700
C9—C10	1.4110 (19)	C21—H21A	0.9600
C9—H9A	0.9300	C21—H21B	0.9600
C11—C12	1.4327 (19)	C21—H21C	0.9600
C11—H11A	0.9300
C13—O1—H1O	109.5	O1—C13—C12	120.46 (12)
C11—N1—C1	121.73 (11)	C14—C13—C12	121.33 (11)
C15—N2—C20	121.50 (12)	C13—C14—C15	121.45 (11)
C15—N2—C18B	122.08 (15)	C13—C14—H14A	119.3
C20—N2—C18B	112.15 (16)	C15—C14—H14A	119.3
C15—N2—C18A	114.8 (2)	N2—C15—C14	122.00 (11)
C20—N2—C18A	123.6 (2)	N2—C15—C16	120.89 (12)
C18B—N2—C18A	25.5 (2)	C14—C15—C16	117.11 (12)
C2—C1—N1	122.56 (13)	C17—C16—C15	120.05 (13)
C2—C1—C10	119.77 (12)	C17—C16—H16A	120.0
N1—C1—C10	117.40 (11)	C15—C16—H16A	120.0
C1—C2—C3	120.60 (14)	C16—C17—C12	123.12 (13)
C1—C2—H2A	119.7	C16—C17—H17A	118.4
C3—C2—H2A	119.7	C12—C17—H17A	118.4
C4—C3—C2	121.33 (13)	C19A—C18A—N2	112.1 (5)
C4—C3—H3A	119.3	C19A—C18A—H18A	109.2
C2—C3—H3A	119.3	N2—C18A—H18A	109.2
C3—C4—C5	119.88 (14)	C19A—C18A—H18B	109.2
C3—C4—H4A	120.1	N2—C18A—H18B	109.2
C5—C4—H4A	120.1	H18A—C18A—H18B	107.9
C10—C5—C6	118.91 (13)	N2—C18B—C19B	111.6 (2)
C10—C5—C4	119.32 (13)	N2—C18B—H18C	109.3
C6—C5—C4	121.77 (14)	C19B—C18B—H18C	109.3
C7—C6—C5	120.68 (15)	N2—C18B—H18D	109.3
C7—C6—H6A	119.7	C19B—C18B—H18D	109.3
C5—C6—H6A	119.7	H18C—C18B—H18D	108.0
C6—C7—C8	119.71 (15)	C18B—C19B—H19D	109.5
C6—C7—H7A	120.1	C18B—C19B—H19E	109.5
C8—C7—H7A	120.1	H19D—C19B—H19E	109.5
C9—C8—C7	121.14 (14)	C18B—C19B—H19F	109.5
C9—C8—H8A	119.4	H19D—C19B—H19F	109.5
C7—C8—H8A	119.4	H19E—C19B—H19F	109.5
C8—C9—C10	121.07 (14)	N2—C20—C21	114.57 (15)
C8—C9—H9A	119.5	N2—C20—H20A	108.6
C10—C9—H9A	119.5	C21—C20—H20A	108.6
C5—C10—C9	118.49 (12)	N2—C20—H20B	108.6
C5—C10—C1	119.08 (12)	C21—C20—H20B	108.6
C9—C10—C1	122.44 (12)	H20A—C20—H20B	107.6
N1—C11—C12	122.86 (11)	C20—C21—H21A	109.5
N1—C11—H11A	118.6	C20—C21—H21B	109.5
C12—C11—H11A	118.6	H21A—C21—H21B	109.5
C17—C12—C13	116.90 (12)	C20—C21—H21C	109.5
C17—C12—C11	121.35 (12)	H21A—C21—H21C	109.5
C13—C12—C11	121.74 (11)	H21B—C21—H21C	109.5
O1—C13—C14	118.19 (11)
C11—N1—C1—C2	46.16 (18)	C11—C12—C13—O1	−1.77 (19)
C11—N1—C1—C10	−139.83 (12)	C17—C12—C13—C14	−2.00 (19)
N1—C1—C2—C3	172.06 (12)	C11—C12—C13—C14	176.64 (12)
C10—C1—C2—C3	−1.81 (19)	O1—C13—C14—C15	178.56 (12)
C1—C2—C3—C4	0.8 (2)	C12—C13—C14—C15	0.1 (2)
C2—C3—C4—C5	0.6 (2)	C20—N2—C15—C14	173.50 (13)
C3—C4—C5—C10	−0.97 (19)	C18B—N2—C15—C14	18.5 (2)
C3—C4—C5—C6	179.22 (14)	C18A—N2—C15—C14	−9.3 (3)
C10—C5—C6—C7	0.4 (2)	C20—N2—C15—C16	−6.1 (2)
C4—C5—C6—C7	−179.83 (13)	C18B—N2—C15—C16	−161.04 (18)
C5—C6—C7—C8	0.4 (2)	C18A—N2—C15—C16	171.1 (2)
C6—C7—C8—C9	−0.9 (2)	C13—C14—C15—N2	−178.13 (12)
C7—C8—C9—C10	0.7 (2)	C13—C14—C15—C16	1.5 (2)
C6—C5—C10—C9	−0.63 (17)	N2—C15—C16—C17	178.46 (14)
C4—C5—C10—C9	179.56 (12)	C14—C15—C16—C17	−1.1 (2)
C6—C5—C10—C1	179.79 (12)	C15—C16—C17—C12	−0.8 (2)
C4—C5—C10—C1	−0.02 (17)	C13—C12—C17—C16	2.3 (2)
C8—C9—C10—C5	0.12 (19)	C11—C12—C17—C16	−176.30 (14)
C8—C9—C10—C1	179.69 (13)	C15—N2—C18A—C19A	178.1 (5)
C2—C1—C10—C5	1.40 (17)	C20—N2—C18A—C19A	−4.8 (6)
N1—C1—C10—C5	−172.78 (10)	C18B—N2—C18A—C19A	65.1 (6)
C2—C1—C10—C9	−178.16 (12)	C15—N2—C18B—C19B	−121.8 (4)
N1—C1—C10—C9	7.66 (17)	C20—N2—C18B—C19B	81.2 (4)
C1—N1—C11—C12	−172.94 (12)	C18A—N2—C18B—C19B	−41.2 (6)
N1—C11—C12—C17	−175.92 (13)	C15—N2—C20—C21	−81.05 (19)
N1—C11—C12—C13	5.5 (2)	C18B—N2—C20—C21	76.2 (2)
C17—C12—C13—O1	179.60 (12)	C18A—N2—C20—C21	102.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.82	1.87	2.6060 (14)	148
C16—H16A···Cg1^i^i	0.93	2.84	3.6475 (15)	145
C17—H17A···Cg2^i^i	0.93	2.85	3.6502 (15)	145
C19A—H19A···Cg1^ii^ii	0.88	2.88	3.747 (7)	142
C19B—H19D···Cg1^ii^ii	0.88	2.88	3.688 (4)	149

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y−1/2, −z+2.