Crystal structure of (E)-N-[(2-meth­oxy­naphthalen-1-yl)methyl­idene]-3-nitro­aniline

In the title compound, C₁₈H₁₄N₂O₃, the dihedral angle between the naphthalene ring system and the benzene ring is 59.99 (13)°. A short intra­molecular C—H...N contact closes an S(6) ring. The nitro group is disordered over two orientations in a statistical ratio. In the crystal, weak C—H...O hydrogen bonds and very weak π–π stacking inter­actions [centroid–centroid separation = 3.9168 (17) Å] are observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.055
• wR factor = 0.143
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT482_ALERT_4_A Small D-H..A Angle Rep for C16    ..  N2      ..       2.96 Degree
PLAT482_ALERT_4_A Small D-H..A Angle Rep for C13    ..  O1'     ..       3.32 Degree
PLAT482_ALERT_4_A Small D-H..A Angle Rep for C18    ..  O2      ..       3.13 Degree
PLAT776_ALERT_1_A Suspect D-H Dist in CIF:   C13    --  H13     ..       2.66 Ang.
PLAT776_ALERT_1_A Suspect D-H Dist in CIF:   C18    --  H18A    ..       3.56 Ang.

Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.485 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          9 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          9 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         42 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report

   5 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

# start Validation Reply Form
_vrf_PLAT482_I
;
PROBLEM: Small D-H..A Angle Rep for C16    ..  N2      ..       2.96 Degree
RESPONSE: ...
;
_vrf_PLAT776_I
;
PROBLEM: Suspect D-H Dist in CIF:   C13    --  H13     ..       2.66 Ang.
RESPONSE: ...
;
# end Validation Reply Form

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S1. Chemical context

Schiff bases are considered an important class of organic compounds, which have wide applications. In recent years, they have gained significant inter­est in the area of drug research and development owing to the broad bioactivities such as insecticidal, anti­bacterial, anti­tuberculosis and anti­microbial reported for the compounds and their metal complexes. These compounds play an important role in biological systems and are observed in various enzymes such as transaminases, tryptophan synthase etc. The important physical and biological properties of these compounds are related to the presence of the intra­molecular hydrogen bond and proton transfer equilibrium. Schiff bases have also been utilized as ligands to synthesize metal complexes with inter­esting applications. The steric and inductive effects introduced by substituents present on the aromatic portion of the Schiff base can influence the properties of the ligand significantly. In continuation of our efforts in understanding the role of subtle electronic variations such as substituent effects on Chemistry and activity of Schiff bases and their metal complexes, we herein report the crystal structure of Schiff base derived from 3-nitro­aniline and 2-meth­oxy naphthaldehyde (Tolulope et al., 2013).

S2. Structural commentary

The molecule of title compound is non-planar, with a dihedral angle between the naphthyl and phenyl aromatic rings of 59.99 (13)°, in which the two rings are twisted from one another. The C9—O3 single bond of 1.358 (3) Å and the C7═N2 double bond of 1.261 (3) Å .The bond angle of C5—N2—C7 of the imine group is 117.5 (2)°, less than 120°. The bond length of the nitro group is N1—O2(1.241 (6)Å) and N1—O1(1.239 (6)Å) and bond angle in O2—N1—O1 is 123.4 (12)° which is more than the planar bond angle of 120°. The torsion angles C8—C7—N2—C5 is 178.1 (2)°.These values support that the configurations about the N2=C7 bond is anti­(E-form), which is in accordance with the enol-imine tautomeric form.

S3. Supra­molecular features

The title compound has an intra molecular C16— H16···N2 hydrogen bond forming an S(6) motif (Table 2). Also there is a C—H···O inter­molecular inter­action, in which a C—H of the naphthyl ring of one molecule and O-atom of the nitro group of another molecule are linked to one another.

S4. Synthesis and crystallization

The block-like, yellow single crystals of the compound C₁₈ H₁₄ N₂ O₃, were grown using 1:1 mixture of CHCl₃ and methanol as solvent by slow evaporation technique.

S5. Refinement

The hydrogen atoms in the structure were positioned geometrically (C—H = 0.93–0.98 Å. N—H = 0.86Å) and were refined using a riding model with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl and 1.2 for all other atoms. The two oxygen atoms of the nitro group are disordered over two orientations. The SADI, SIMU, and ISOR commands in SHELXL (Sheldrick, 2015) were used to model the disorder.

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature

For background to Schiff bases, see: Tolulope et al. (2013).

Structure description

Schiff bases are considered an important class of organic compounds, which have wide applications. In recent years, they have gained significant inter­est in the area of drug research and development owing to the broad bioactivities such as insecticidal, anti­bacterial, anti­tuberculosis and anti­microbial reported for the compounds and their metal complexes. These compounds play an important role in biological systems and are observed in various enzymes such as transaminases, tryptophan synthase etc. The important physical and biological properties of these compounds are related to the presence of the intra­molecular hydrogen bond and proton transfer equilibrium. Schiff bases have also been utilized as ligands to synthesize metal complexes with inter­esting applications. The steric and inductive effects introduced by substituents present on the aromatic portion of the Schiff base can influence the properties of the ligand significantly. In continuation of our efforts in understanding the role of subtle electronic variations such as substituent effects on Chemistry and activity of Schiff bases and their metal complexes, we herein report the crystal structure of Schiff base derived from 3-nitro­aniline and 2-meth­oxy naphthaldehyde (Tolulope et al., 2013).

The molecule of title compound is non-planar, with a dihedral angle between the naphthyl and phenyl aromatic rings of 59.99 (13)°, in which the two rings are twisted from one another. The C9—O3 single bond of 1.358 (3) Å and the C7═N2 double bond of 1.261 (3) Å .The bond angle of C5—N2—C7 of the imine group is 117.5 (2)°, less than 120°. The bond length of the nitro group is N1—O2(1.241 (6)Å) and N1—O1(1.239 (6)Å) and bond angle in O2—N1—O1 is 123.4 (12)° which is more than the planar bond angle of 120°. The torsion angles C8—C7—N2—C5 is 178.1 (2)°.These values support that the configurations about the N2=C7 bond is anti­(E-form), which is in accordance with the enol-imine tautomeric form.

The title compound has an intra molecular C16— H16···N2 hydrogen bond forming an S(6) motif (Table 2). Also there is a C—H···O inter­molecular inter­action, in which a C—H of the naphthyl ring of one molecule and O-atom of the nitro group of another molecule are linked to one another.

For background to Schiff bases, see: Tolulope et al. (2013).

Synthesis and crystallization

The block-like, yellow single crystals of the compound C₁₈ H₁₄ N₂ O₃, were grown using 1:1 mixture of CHCl₃ and methanol as solvent by slow evaporation technique.

Refinement details

The hydrogen atoms in the structure were positioned geometrically (C—H = 0.93–0.98 Å. N—H = 0.86Å) and were refined using a riding model with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl and 1.2 for all other atoms. The two oxygen atoms of the nitro group are disordered over two orientations. The SADI, SIMU, and ISOR commands in SHELXL (Sheldrick, 2015) were used to model the disorder.

Crystal data, data collection and structure refinement details are summarized in Table 1.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures

	Fig. 1. Plot of the title compound showing the intramolecular C—H···N interaction as a dashed line.
	Fig. 2. Crystal packing diagram showing the C—H···N and C—H···O interactions as dashed lines

(E)-N-[(2-Methoxynaphthalen-1-yl)methylidene]-3-nitroaniline

Crystal data

C18H14N2O3	Dx = 1.362 Mg m^−3
Mr = 306.31	Melting point: 407 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8481 (7) Å	Cell parameters from 5867 reflections
b = 15.4085 (6) Å	θ = 2.6–29.9°
c = 7.6232 (3) Å	µ = 0.09 mm^−1
β = 98.040 (4)°	T = 293 K
V = 1494.33 (12) Å^3	Block, yellow
Z = 4	0.35 × 0.30 × 0.25 mm
F(000) = 640

Data collection

Bruker Kappa APEXII CCD diffractometer	2622 independent reflections
Radiation source: fine-focus sealed tube	1646 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω and φ scan	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→15
Tmin = 0.957, Tmax = 0.989	k = −18→18
21149 measured reflections	l = −9→8

Refinement

Refinement on F^2	42 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 0.9181P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
2622 reflections	Δρmax = 0.16 e Å^−3
227 parameters	Δρmin = −0.17 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.0584 (2)	−0.09762 (18)	0.7746 (4)	0.0523 (7)
C2	−0.0226 (2)	−0.03905 (19)	0.7675 (4)	0.0523 (7)
H2	−0.0893	−0.0562	0.7877	0.063*
C3	−0.0015 (2)	0.0457 (2)	0.7296 (4)	0.0566 (8)
H3	−0.0545	0.0870	0.7247	0.068*
C4	0.0976 (2)	0.07014 (18)	0.6986 (4)	0.0517 (7)
H4	0.1103	0.1276	0.6710	0.062*
C5	0.17862 (19)	0.01015 (18)	0.7081 (3)	0.0461 (7)
C6	0.1585 (2)	−0.07494 (18)	0.7487 (4)	0.0498 (7)
H6	0.2118	−0.1162	0.7583	0.060*
C7	0.2942 (2)	0.07229 (17)	0.5418 (4)	0.0475 (7)
H7	0.2333	0.0823	0.4630	0.057*
C8	0.39198 (19)	0.10445 (16)	0.4875 (3)	0.0430 (6)
C9	0.3839 (2)	0.13912 (17)	0.3178 (4)	0.0485 (7)
C10	0.4724 (2)	0.17407 (18)	0.2520 (4)	0.0571 (8)
H10	0.4658	0.1972	0.1383	0.069*
C11	0.5665 (2)	0.17361 (19)	0.3552 (4)	0.0585 (8)
H11	0.6242	0.1970	0.3107	0.070*
C12	0.5808 (2)	0.13905 (17)	0.5278 (4)	0.0480 (7)
C13	0.6798 (2)	0.1397 (2)	0.6330 (4)	0.0622 (8)
H13	0.7372	0.1626	0.5870	0.075*
C14	0.6933 (2)	0.1077 (2)	0.7988 (5)	0.0649 (9)
H14	0.7595	0.1082	0.8662	0.078*
C15	0.6069 (2)	0.0736 (2)	0.8696 (4)	0.0622 (8)
H15	0.6161	0.0521	0.9847	0.075*
C16	0.5094 (2)	0.07154 (18)	0.7716 (4)	0.0537 (7)
H16	0.4532	0.0484	0.8211	0.064*
C17	0.49240 (19)	0.10383 (16)	0.5969 (3)	0.0424 (6)
C18	0.2726 (3)	0.1775 (2)	0.0501 (4)	0.0753 (10)
H18A	0.2006	0.1711	−0.0023	0.113*
H18B	0.2897	0.2381	0.0620	0.113*
H18C	0.3176	0.1502	−0.0242	0.113*
N1	0.0376 (2)	−0.18893 (19)	0.8121 (5)	0.0849 (9)
N2	0.28245 (17)	0.03270 (16)	0.6825 (3)	0.0544 (6)
O3	0.28735 (15)	0.13796 (14)	0.2188 (3)	0.0669 (6)
O1	0.1053 (10)	−0.2414 (9)	0.778 (4)	0.106 (5)	0.50 (4)
O2	−0.0433 (13)	−0.2105 (10)	0.869 (4)	0.108 (5)	0.50 (4)
O1'	0.1105 (8)	−0.2356 (11)	0.876 (4)	0.106 (5)	0.50 (4)
O2'	−0.0556 (6)	−0.2107 (9)	0.772 (3)	0.097 (4)	0.50 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0460 (16)	0.0463 (17)	0.0646 (19)	−0.0062 (13)	0.0072 (14)	0.0025 (14)
C2	0.0372 (15)	0.061 (2)	0.0598 (18)	−0.0039 (13)	0.0102 (13)	−0.0005 (15)
C3	0.0424 (16)	0.059 (2)	0.069 (2)	0.0107 (14)	0.0099 (14)	0.0020 (15)
C4	0.0476 (16)	0.0463 (16)	0.0620 (18)	−0.0013 (13)	0.0096 (13)	0.0044 (14)
C5	0.0354 (14)	0.0553 (18)	0.0477 (16)	−0.0035 (13)	0.0059 (12)	−0.0008 (13)
C6	0.0393 (15)	0.0476 (17)	0.0625 (18)	0.0038 (12)	0.0077 (13)	0.0042 (13)
C7	0.0418 (15)	0.0458 (16)	0.0548 (18)	−0.0055 (12)	0.0063 (13)	−0.0008 (13)
C8	0.0444 (16)	0.0331 (14)	0.0543 (17)	−0.0011 (11)	0.0163 (13)	−0.0015 (12)
C9	0.0487 (17)	0.0414 (16)	0.0577 (18)	−0.0013 (12)	0.0149 (14)	−0.0002 (13)
C10	0.062 (2)	0.0522 (18)	0.0618 (19)	−0.0004 (14)	0.0238 (16)	0.0072 (14)
C11	0.0534 (19)	0.0560 (19)	0.072 (2)	−0.0088 (14)	0.0310 (16)	−0.0021 (15)
C12	0.0446 (16)	0.0420 (16)	0.0609 (18)	−0.0049 (12)	0.0196 (14)	−0.0074 (13)
C13	0.0451 (18)	0.072 (2)	0.073 (2)	−0.0127 (15)	0.0206 (16)	−0.0146 (17)
C14	0.0406 (17)	0.081 (2)	0.073 (2)	−0.0059 (15)	0.0070 (15)	−0.0106 (18)
C15	0.0538 (19)	0.073 (2)	0.0598 (19)	−0.0040 (16)	0.0084 (15)	0.0028 (16)
C16	0.0436 (16)	0.0553 (18)	0.0644 (19)	−0.0043 (13)	0.0146 (14)	0.0028 (15)
C17	0.0420 (15)	0.0313 (14)	0.0567 (17)	−0.0024 (11)	0.0164 (13)	−0.0051 (12)
C18	0.074 (2)	0.091 (3)	0.061 (2)	−0.0056 (19)	0.0080 (17)	0.0119 (18)
N1	0.062 (2)	0.0590 (19)	0.136 (3)	−0.0098 (16)	0.021 (2)	0.0112 (19)
N2	0.0412 (13)	0.0627 (16)	0.0610 (15)	−0.0060 (11)	0.0132 (11)	0.0063 (13)
O3	0.0566 (13)	0.0810 (15)	0.0629 (13)	−0.0057 (11)	0.0072 (10)	0.0200 (11)
O1	0.086 (5)	0.061 (4)	0.170 (12)	0.014 (3)	0.012 (6)	0.019 (6)
O2	0.094 (6)	0.071 (4)	0.172 (12)	−0.023 (4)	0.066 (6)	0.021 (8)
O1'	0.083 (5)	0.069 (5)	0.165 (12)	0.003 (4)	0.008 (6)	0.056 (7)
O2'	0.074 (4)	0.067 (4)	0.153 (11)	−0.025 (3)	0.029 (4)	0.002 (7)

Geometric parameters (Å, º)

C1—C2	1.372 (4)	C11—H11	0.9300
C1—C6	1.374 (4)	C11—C12	1.407 (4)
C1—N1	1.468 (4)	C12—C13	1.406 (4)
C2—H2	0.9300	C12—C17	1.425 (3)
C2—C3	1.372 (4)	C13—H13	0.9300
C3—H3	0.9300	C13—C14	1.345 (4)
C3—C4	1.380 (4)	C14—H14	0.9300
C4—H4	0.9300	C14—C15	1.402 (4)
C4—C5	1.386 (4)	C15—H15	0.9300
C5—C6	1.380 (4)	C15—C16	1.366 (4)
C5—N2	1.418 (3)	C16—H16	0.9300
C6—H6	0.9300	C16—C17	1.410 (4)
C7—H7	0.9300	C18—H18A	0.9600
C7—C8	1.463 (3)	C18—H18B	0.9600
C7—N2	1.261 (3)	C18—H18C	0.9600
C8—C9	1.390 (4)	C18—O3	1.412 (3)
C8—C17	1.435 (4)	N1—O1	1.241 (6)
C9—C10	1.412 (4)	N1—O2	1.227 (6)
C9—O3	1.358 (3)	N1—O1'	1.227 (6)
C10—H10	0.9300	N1—O2'	1.239 (6)
C10—C11	1.347 (4)
C2—C1—C6	123.1 (3)	C11—C12—C17	118.9 (3)
C2—C1—N1	118.7 (3)	C13—C12—C11	121.4 (3)
C6—C1—N1	118.2 (3)	C13—C12—C17	119.7 (3)
C1—C2—H2	121.2	C12—C13—H13	119.3
C3—C2—C1	117.6 (3)	C14—C13—C12	121.4 (3)
C3—C2—H2	121.2	C14—C13—H13	119.3
C2—C3—H3	119.7	C13—C14—H14	120.2
C2—C3—C4	120.7 (3)	C13—C14—C15	119.6 (3)
C4—C3—H3	119.7	C15—C14—H14	120.2
C3—C4—H4	119.6	C14—C15—H15	119.6
C3—C4—C5	120.9 (3)	C16—C15—C14	120.9 (3)
C5—C4—H4	119.6	C16—C15—H15	119.6
C4—C5—N2	122.9 (2)	C15—C16—H16	119.4
C6—C5—C4	118.8 (2)	C15—C16—C17	121.1 (3)
C6—C5—N2	118.2 (2)	C17—C16—H16	119.4
C1—C6—C5	118.9 (2)	C12—C17—C8	118.8 (2)
C1—C6—H6	120.6	C16—C17—C8	124.0 (2)
C5—C6—H6	120.6	C16—C17—C12	117.2 (2)
C8—C7—H7	116.1	H18A—C18—H18B	109.5
N2—C7—H7	116.1	H18A—C18—H18C	109.5
N2—C7—C8	127.9 (3)	H18B—C18—H18C	109.5
C9—C8—C7	116.0 (2)	O3—C18—H18A	109.5
C9—C8—C17	119.2 (2)	O3—C18—H18B	109.5
C17—C8—C7	124.8 (2)	O3—C18—H18C	109.5
C8—C9—C10	121.2 (3)	O1—N1—C1	115.6 (9)
O3—C9—C8	117.1 (2)	O2—N1—C1	121.0 (8)
O3—C9—C10	121.7 (3)	O2—N1—O1	123.4 (12)
C9—C10—H10	120.3	O1'—N1—C1	119.3 (8)
C11—C10—C9	119.5 (3)	O1'—N1—O2'	126.6 (12)
C11—C10—H10	120.3	O2'—N1—C1	114.1 (8)
C10—C11—H11	118.7	C7—N2—C5	117.5 (2)
C10—C11—C12	122.5 (3)	C9—O3—C18	119.7 (2)
C12—C11—H11	118.7
C1—C2—C3—C4	0.5 (4)	C9—C8—C17—C16	179.0 (2)
C2—C1—C6—C5	−2.1 (4)	C9—C10—C11—C12	0.3 (4)
C2—C1—N1—O1	164.6 (15)	C10—C9—O3—C18	−4.2 (4)
C2—C1—N1—O2	−13.9 (19)	C10—C11—C12—C13	−179.8 (3)
C2—C1—N1—O1'	−156.0 (17)	C10—C11—C12—C17	−0.6 (4)
C2—C1—N1—O2'	24.5 (14)	C11—C12—C13—C14	179.1 (3)
C2—C3—C4—C5	−1.1 (4)	C11—C12—C17—C8	0.3 (4)
C3—C4—C5—C6	0.2 (4)	C11—C12—C17—C16	−178.6 (2)
C3—C4—C5—N2	−178.1 (2)	C12—C13—C14—C15	−0.5 (5)
C4—C5—C6—C1	1.3 (4)	C13—C12—C17—C8	179.6 (2)
C4—C5—N2—C7	−53.8 (4)	C13—C12—C17—C16	0.6 (4)
C6—C1—C2—C3	1.1 (4)	C13—C14—C15—C16	0.7 (5)
C6—C1—N1—O1	−15.6 (15)	C14—C15—C16—C17	−0.2 (5)
C6—C1—N1—O2	165.9 (18)	C15—C16—C17—C8	−179.3 (3)
C6—C1—N1—O1'	23.9 (17)	C15—C16—C17—C12	−0.4 (4)
C6—C1—N1—O2'	−155.6 (13)	C17—C8—C9—C10	−0.4 (4)
C6—C5—N2—C7	127.9 (3)	C17—C8—C9—O3	179.7 (2)
C7—C8—C9—C10	178.5 (2)	C17—C12—C13—C14	−0.1 (4)
C7—C8—C9—O3	−1.4 (3)	N1—C1—C2—C3	−179.0 (3)
C7—C8—C17—C12	−178.7 (2)	N1—C1—C6—C5	178.1 (3)
C7—C8—C17—C16	0.2 (4)	N2—C5—C6—C1	179.7 (2)
C8—C7—N2—C5	178.1 (2)	N2—C7—C8—C9	174.4 (3)
C8—C9—C10—C11	0.2 (4)	N2—C7—C8—C17	−6.8 (4)
C8—C9—O3—C18	175.7 (3)	O3—C9—C10—C11	−179.9 (3)
C9—C8—C17—C12	0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N2	0.93	2.31	2.961 (3)	127
C13—H13···O1′^i	0.93	2.49	3.318 (14)	148
C18—H18A···O2^ii	0.96	2.46	3.135 (18)	127

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, −y, −z+1.