Crystal structure of 2-{[(E)-(4-anilinophen­yl)iminium­yl]meth­yl}-5-(di­ethyl­amino)­phenolate

The title compound, C₂₃H₂₅N₃O, crystallized with one single mol­ecule in the asymmetric unit and present in the zwitterionic form. In the crystal, mol­ecules are connected by N—H...O hydrogen bonds generating –A–B–A–B– zigzag chains extending along [010]. The chains are linked via C—H...π inter­actions and π–π inter­actions [with a centroid–centroid distance of 3.444 (3) Å)] between the benzene ring and the imino group of symmetry-related mol­ecules, forming slabs lying parallel to (100).

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.138
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.101 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          2 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          42 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...         15 Check

   0 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
   5 ALERT level G = General information/check it is not something unexpected

   1 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
   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

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenberg & Putz, 2006) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

2-{[(E)-(4-Anilinophenyl)iminiumyl]methyl}-5-(diethylamino)phenolate

Crystal data

C23H25N3O	F(000) = 768
Mr = 359.46	Dx = 1.267 Mg m^−3
Monoclinic, P21/c	Melting point: 270 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 18.0358 (16) Å	Cell parameters from 2553 reflections
b = 11.3851 (8) Å	θ = 2.7–23.7°
c = 9.4815 (9) Å	µ = 0.08 mm^−1
β = 104.560 (3)°	T = 100 K
V = 1884.4 (3) Å^3	Needle, dark yellow
Z = 4	0.20 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer	3322 independent reflections
Radiation source: fine-focus sealed tube	2186 reflections with I > 2σ(I)'
Graphite monochromator	Rint = 0.078
ω–scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→21
Tmin = 0.984, Tmax = 0.991	k = −13→13
14768 measured reflections	l = −11→11

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0763P)^2] where P = (Fo^2 + 2Fc^2)/3
3322 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.16973 (12)	0.14061 (19)	−0.0731 (3)	0.0162 (5)
C2	0.22412 (11)	0.10711 (19)	−0.1497 (2)	0.0168 (5)
H2	0.2319	0.0275	−0.1624	0.020*
C3	0.26674 (11)	0.18820 (19)	−0.2072 (2)	0.0160 (5)
C4	0.25415 (12)	0.31118 (19)	−0.1877 (3)	0.0174 (5)
H4	0.2823	0.3671	−0.2235	0.021*
C5	0.20136 (12)	0.34542 (19)	−0.1173 (3)	0.0185 (5)
H5	0.1937	0.4254	−0.1069	0.022*
C6	0.15719 (11)	0.26528 (18)	−0.0586 (2)	0.0156 (5)
C7	0.36691 (12)	0.2388 (2)	−0.3332 (3)	0.0220 (6)
H7A	0.3355	0.3049	−0.3767	0.026*
H7B	0.3863	0.2018	−0.4089	0.026*
C8	0.43420 (13)	0.2845 (2)	−0.2161 (3)	0.0284 (6)
H8A	0.4157	0.3308	−0.1476	0.043*
H8B	0.4661	0.3322	−0.2602	0.043*
H8C	0.4634	0.2195	−0.1666	0.043*
C9	0.33326 (15)	0.0308 (2)	−0.3032 (3)	0.0325 (7)
H9A	0.3523	0.0229	−0.3898	0.039*
H9B	0.2852	−0.0117	−0.3203	0.039*
C10	0.39020 (15)	−0.0248 (2)	−0.1758 (3)	0.0445 (8)
H10A	0.4397	0.0102	−0.1658	0.067*
H10B	0.3932	−0.1076	−0.1927	0.067*
H10C	0.3738	−0.0122	−0.0882	0.067*
C11	0.10234 (11)	0.30625 (19)	0.0085 (2)	0.0175 (5)
H11	0.0970	0.3871	0.0163	0.021*
C12	−0.00088 (11)	0.27358 (19)	0.1280 (2)	0.0159 (5)
C13	−0.00286 (12)	0.38568 (19)	0.1858 (3)	0.0180 (6)
H13	0.0362	0.4388	0.1853	0.022*
C14	−0.06264 (11)	0.41801 (19)	0.2439 (3)	0.0183 (6)
H14	−0.0639	0.4936	0.2805	0.022*
C15	−0.12107 (12)	0.33966 (19)	0.2488 (3)	0.0163 (5)
C16	−0.11642 (12)	0.22592 (19)	0.1981 (3)	0.0202 (6)
H16	−0.1534	0.1710	0.2052	0.024*
C17	−0.05756 (12)	0.19375 (19)	0.1374 (3)	0.0182 (5)
H17	−0.0558	0.1178	0.1024	0.022*
C18	−0.25825 (12)	0.36660 (18)	0.2449 (3)	0.0167 (5)
C19	−0.30949 (12)	0.41195 (19)	0.3197 (3)	0.0201 (6)
H19	−0.2908	0.4431	0.4126	0.024*
C20	−0.38707 (12)	0.41113 (19)	0.2581 (3)	0.0231 (6)
H20	−0.4201	0.4423	0.3095	0.028*
C21	−0.41679 (13)	0.3645 (2)	0.1205 (3)	0.0251 (6)
H21	−0.4693	0.3646	0.0789	0.030*
C22	−0.36671 (13)	0.31798 (19)	0.0465 (3)	0.0241 (6)
H22	−0.3860	0.2859	−0.0457	0.029*
C23	−0.28811 (12)	0.31815 (19)	0.1069 (3)	0.0204 (6)
H23	−0.2554	0.2860	0.0555	0.025*
N1	0.31894 (10)	0.15485 (16)	−0.2813 (2)	0.0205 (5)
N2	0.05736 (10)	0.23777 (17)	0.0618 (2)	0.0170 (5)
N3	−0.18057 (10)	0.37535 (18)	0.3112 (2)	0.0199 (5)
O1	0.13165 (8)	0.06417 (12)	−0.01909 (17)	0.0187 (4)
H2N	0.0678 (14)	0.161 (2)	0.050 (3)	0.038 (8)*
H3H	−0.1685 (13)	0.430 (2)	0.374 (3)	0.024 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0140 (11)	0.0188 (12)	0.0139 (14)	−0.0018 (10)	−0.0001 (10)	0.0019 (10)
C2	0.0178 (12)	0.0127 (12)	0.0190 (15)	0.0013 (9)	0.0028 (11)	−0.0016 (10)
C3	0.0122 (11)	0.0231 (13)	0.0108 (13)	0.0026 (10)	−0.0006 (10)	−0.0003 (10)
C4	0.0147 (12)	0.0174 (12)	0.0191 (14)	−0.0012 (10)	0.0026 (11)	0.0042 (10)
C5	0.0168 (12)	0.0165 (12)	0.0204 (15)	0.0024 (10)	0.0012 (11)	0.0018 (10)
C6	0.0119 (11)	0.0172 (12)	0.0161 (14)	0.0006 (10)	0.0008 (10)	0.0015 (10)
C7	0.0190 (12)	0.0279 (14)	0.0209 (15)	0.0008 (11)	0.0086 (11)	0.0013 (11)
C8	0.0212 (13)	0.0314 (15)	0.0331 (17)	−0.0008 (11)	0.0074 (12)	0.0004 (12)
C9	0.0409 (15)	0.0240 (14)	0.0423 (19)	0.0041 (12)	0.0286 (14)	−0.0026 (13)
C10	0.0403 (16)	0.0339 (16)	0.069 (2)	0.0145 (13)	0.0320 (17)	0.0186 (16)
C11	0.0166 (12)	0.0146 (12)	0.0191 (15)	−0.0008 (10)	0.0004 (11)	0.0022 (10)
C12	0.0134 (11)	0.0201 (13)	0.0138 (14)	0.0018 (10)	0.0024 (10)	0.0015 (10)
C13	0.0139 (12)	0.0185 (13)	0.0200 (15)	−0.0027 (10)	0.0015 (11)	0.0003 (10)
C14	0.0166 (12)	0.0172 (12)	0.0200 (15)	0.0010 (10)	0.0026 (11)	−0.0029 (10)
C15	0.0144 (11)	0.0195 (13)	0.0142 (14)	0.0019 (10)	0.0021 (10)	0.0000 (10)
C16	0.0164 (12)	0.0177 (13)	0.0264 (16)	−0.0027 (10)	0.0054 (11)	0.0016 (11)
C17	0.0173 (12)	0.0152 (12)	0.0206 (15)	0.0005 (10)	0.0021 (11)	−0.0027 (10)
C18	0.0161 (12)	0.0121 (11)	0.0222 (15)	0.0000 (10)	0.0054 (11)	0.0052 (10)
C19	0.0207 (12)	0.0173 (13)	0.0232 (15)	−0.0022 (10)	0.0073 (11)	−0.0002 (11)
C20	0.0174 (13)	0.0212 (13)	0.0336 (18)	0.0009 (10)	0.0120 (12)	0.0020 (12)
C21	0.0134 (12)	0.0228 (13)	0.0367 (18)	−0.0020 (10)	0.0019 (12)	0.0015 (12)
C22	0.0227 (13)	0.0225 (13)	0.0238 (16)	−0.0027 (11)	−0.0003 (12)	−0.0014 (11)
C23	0.0198 (12)	0.0176 (13)	0.0246 (16)	0.0018 (10)	0.0069 (11)	0.0012 (11)
N1	0.0204 (10)	0.0201 (11)	0.0232 (13)	0.0025 (9)	0.0095 (9)	0.0008 (9)
N2	0.0165 (10)	0.0148 (11)	0.0202 (13)	0.0016 (9)	0.0056 (9)	0.0002 (9)
N3	0.0138 (10)	0.0225 (12)	0.0238 (13)	−0.0010 (9)	0.0052 (9)	−0.0077 (10)
O1	0.0161 (8)	0.0164 (8)	0.0241 (10)	−0.0014 (7)	0.0064 (7)	0.0021 (7)

Geometric parameters (Å, º)

C1—O1	1.292 (2)	C11—H11	0.9300
C1—C2	1.412 (3)	C12—C17	1.387 (3)
C1—C6	1.449 (3)	C12—C13	1.393 (3)
C2—C3	1.397 (3)	C12—N2	1.413 (3)
C2—H2	0.9300	C13—C14	1.378 (3)
C3—N1	1.363 (3)	C13—H13	0.9300
C3—C4	1.438 (3)	C14—C15	1.390 (3)
C4—C5	1.351 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.391 (3)
C5—C6	1.414 (3)	C15—N3	1.409 (3)
C5—H5	0.9300	C16—C17	1.378 (3)
C6—C11	1.385 (3)	C16—H16	0.9300
C7—N1	1.455 (3)	C17—H17	0.9300
C7—C8	1.516 (3)	C18—N3	1.388 (3)
C7—H7A	0.9700	C18—C23	1.397 (3)
C7—H7B	0.9700	C18—C19	1.398 (3)
C8—H8A	0.9600	C19—C20	1.374 (3)
C8—H8B	0.9600	C19—H19	0.9300
C8—H8C	0.9600	C20—C21	1.385 (3)
C9—N1	1.460 (3)	C20—H20	0.9300
C9—C10	1.513 (4)	C21—C22	1.381 (3)
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	C22—C23	1.389 (3)
C10—H10A	0.9600	C22—H22	0.9300
C10—H10B	0.9600	C23—H23	0.9300
C10—H10C	0.9600	N2—H2N	0.90 (2)
C11—N2	1.314 (3)	N3—H3H	0.85 (2)
O1—C1—C2	122.0 (2)	C17—C12—C13	118.9 (2)
O1—C1—C6	120.73 (19)	C17—C12—N2	118.80 (19)
C2—C1—C6	117.29 (19)	C13—C12—N2	122.34 (19)
C3—C2—C1	123.0 (2)	C14—C13—C12	120.1 (2)
C3—C2—H2	118.5	C14—C13—H13	119.9
C1—C2—H2	118.5	C12—C13—H13	119.9
N1—C3—C2	122.4 (2)	C13—C14—C15	121.2 (2)
N1—C3—C4	119.32 (19)	C13—C14—H14	119.4
C2—C3—C4	118.23 (19)	C15—C14—H14	119.4
C5—C4—C3	119.9 (2)	C14—C15—C16	118.27 (19)
C5—C4—H4	120.0	C14—C15—N3	119.5 (2)
C3—C4—H4	120.0	C16—C15—N3	122.1 (2)
C4—C5—C6	123.0 (2)	C17—C16—C15	120.8 (2)
C4—C5—H5	118.5	C17—C16—H16	119.6
C6—C5—H5	118.5	C15—C16—H16	119.6
C11—C6—C5	120.1 (2)	C16—C17—C12	120.7 (2)
C11—C6—C1	121.3 (2)	C16—C17—H17	119.7
C5—C6—C1	118.54 (19)	C12—C17—H17	119.7
N1—C7—C8	114.40 (19)	N3—C18—C23	124.1 (2)
N1—C7—H7A	108.7	N3—C18—C19	117.7 (2)
C8—C7—H7A	108.7	C23—C18—C19	118.2 (2)
N1—C7—H7B	108.7	C20—C19—C18	120.9 (2)
C8—C7—H7B	108.7	C20—C19—H19	119.5
H7A—C7—H7B	107.6	C18—C19—H19	119.5
C7—C8—H8A	109.5	C19—C20—C21	121.0 (2)
C7—C8—H8B	109.5	C19—C20—H20	119.5
H8A—C8—H8B	109.5	C21—C20—H20	119.5
C7—C8—H8C	109.5	C22—C21—C20	118.5 (2)
H8A—C8—H8C	109.5	C22—C21—H21	120.7
H8B—C8—H8C	109.5	C20—C21—H21	120.7
N1—C9—C10	113.6 (2)	C21—C22—C23	121.3 (2)
N1—C9—H9A	108.9	C21—C22—H22	119.3
C10—C9—H9A	108.9	C23—C22—H22	119.3
N1—C9—H9B	108.9	C22—C23—C18	120.0 (2)
C10—C9—H9B	108.9	C22—C23—H23	120.0
H9A—C9—H9B	107.7	C18—C23—H23	120.0
C9—C10—H10A	109.5	C3—N1—C7	122.52 (19)
C9—C10—H10B	109.5	C3—N1—C9	120.85 (19)
H10A—C10—H10B	109.5	C7—N1—C9	116.48 (18)
C9—C10—H10C	109.5	C11—N2—C12	126.83 (19)
H10A—C10—H10C	109.5	C11—N2—H2N	110.9 (15)
H10B—C10—H10C	109.5	C12—N2—H2N	122.3 (16)
N2—C11—C6	123.9 (2)	C18—N3—C15	125.3 (2)
N2—C11—H11	118.0	C18—N3—H3H	114.8 (15)
C6—C11—H11	118.0	C15—N3—H3H	114.7 (16)
O1—C1—C2—C3	−179.1 (2)	N2—C12—C17—C16	−178.5 (2)
C6—C1—C2—C3	1.7 (3)	N3—C18—C19—C20	177.1 (2)
C1—C2—C3—N1	−179.8 (2)	C23—C18—C19—C20	−1.3 (3)
C1—C2—C3—C4	−0.3 (3)	C18—C19—C20—C21	0.5 (3)
N1—C3—C4—C5	178.5 (2)	C19—C20—C21—C22	0.4 (3)
C2—C3—C4—C5	−1.0 (3)	C20—C21—C22—C23	−0.5 (3)
C3—C4—C5—C6	0.8 (3)	C21—C22—C23—C18	−0.4 (3)
C4—C5—C6—C11	−178.0 (2)	N3—C18—C23—C22	−177.1 (2)
C4—C5—C6—C1	0.8 (3)	C19—C18—C23—C22	1.2 (3)
O1—C1—C6—C11	−2.4 (3)	C2—C3—N1—C7	−175.9 (2)
C2—C1—C6—C11	176.8 (2)	C4—C3—N1—C7	4.5 (3)
O1—C1—C6—C5	178.8 (2)	C2—C3—N1—C9	−0.5 (3)
C2—C1—C6—C5	−2.0 (3)	C4—C3—N1—C9	180.0 (2)
C5—C6—C11—N2	177.8 (2)	C8—C7—N1—C3	77.6 (3)
C1—C6—C11—N2	−0.9 (3)	C8—C7—N1—C9	−98.1 (2)
C17—C12—C13—C14	−3.6 (3)	C10—C9—N1—C3	−84.0 (3)
N2—C12—C13—C14	177.3 (2)	C10—C9—N1—C7	91.7 (3)
C12—C13—C14—C15	1.3 (3)	C6—C11—N2—C12	−178.3 (2)
C13—C14—C15—C16	2.2 (3)	C17—C12—N2—C11	160.3 (2)
C13—C14—C15—N3	179.0 (2)	C13—C12—N2—C11	−20.5 (3)
C14—C15—C16—C17	−3.4 (3)	C23—C18—N3—C15	1.5 (3)
N3—C15—C16—C17	179.9 (2)	C19—C18—N3—C15	−176.8 (2)
C15—C16—C17—C12	1.2 (4)	C14—C15—N3—C18	127.6 (2)
C13—C12—C17—C16	2.3 (3)	C16—C15—N3—C18	−55.7 (3)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.90 (2)	1.83 (2)	2.609 (2)	143 (2)
N3—H3H···O1^i	0.85 (2)	2.05 (2)	2.900 (3)	175 (2)
C7—H7A···Cg^ii	0.97	2.87	3.465 (3)	121

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