3,4-Bis(2-hydr­oxy-3-methoxy­benzyl­idene­amino)pyridine

In the title mol­ecule, C₂₁H₁₉N₃O₄, the benzene rings of the two ortho 2-hydr­oxy-3-methoxy­benzyl­ideneamine substituents are twisted with respect to the central pyridine ring by 29.4 (1) and 41.4 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.147
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C12    -   C13    ...       1.39 Ang.

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

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 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; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

3,4-Bis(2-hydroxy-3-methoxybenzylideneamino)pyridine

Crystal data

C21H19N3O4	F(000) = 792
Mr = 377.39	Dx = 1.318 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2192 reflections
a = 7.034 (1) Å	θ = 2.5–21.8°
b = 12.419 (1) Å	µ = 0.09 mm^−1
c = 21.788 (2) Å	T = 295 K
β = 92.142 (2)°	Block, orange
V = 1902.1 (4) Å^3	0.36 × 0.24 × 0.21 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2345 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −7→8
10912 measured reflections	k = −8→16
4248 independent reflections	l = −23→28

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.065P)^2 + 0.2087P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4248 reflections	Δρmax = 0.22 e Å^−3
264 parameters	Δρmin = −0.19 e Å^−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

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)
O1	0.0339 (2)	0.20362 (14)	0.41887 (7)	0.0782 (5)
O2	0.2518 (2)	0.29034 (13)	0.33748 (7)	0.0659 (4)
H2O	0.303 (3)	0.3183 (19)	0.3055 (8)	0.098 (9)*
O3	0.44429 (18)	0.56335 (13)	0.35979 (6)	0.0600 (4)
H3O	0.448 (3)	0.5413 (19)	0.3225 (6)	0.089 (9)*
O4	0.5040 (2)	0.62502 (13)	0.47381 (6)	0.0657 (4)
N1	0.3003 (2)	0.35208 (13)	0.22410 (7)	0.0527 (4)
N2	0.5822 (2)	0.49592 (13)	0.25682 (7)	0.0496 (4)
N3	0.6459 (4)	0.4780 (2)	0.08874 (11)	0.1017 (8)	0.50
C3'	0.6459 (4)	0.4780 (2)	0.08874 (11)	0.1017 (8)	0.50
H3'	0.7214	0.5078	0.0590	0.122*	0.50
C1	0.0747 (3)	0.26176 (16)	0.31792 (9)	0.0525 (5)
C2	−0.0456 (3)	0.21611 (17)	0.36091 (10)	0.0581 (5)
C3	−0.2279 (3)	0.18738 (19)	0.34292 (12)	0.0692 (6)
H3	−0.3083	0.1582	0.3715	0.083*
C4	−0.2928 (3)	0.20150 (18)	0.28276 (12)	0.0731 (7)
H4	−0.4167	0.1821	0.2712	0.088*
C5	−0.1769 (3)	0.24350 (18)	0.24030 (11)	0.0659 (6)
H5	−0.2215	0.2516	0.1998	0.079*
C6	0.0095 (3)	0.27476 (16)	0.25713 (9)	0.0516 (5)
C7	0.1285 (3)	0.32148 (16)	0.21169 (9)	0.0565 (5)
H7	0.0790	0.3298	0.1718	0.068*
C8	−0.0751 (4)	0.1513 (2)	0.46337 (11)	0.0955 (9)
H8A	0.0005	0.1426	0.5006	0.143*
H8B	−0.1146	0.0820	0.4482	0.143*
H8C	−0.1852	0.1940	0.4714	0.143*
C9	0.4132 (3)	0.39408 (16)	0.17756 (9)	0.0524 (5)
C10	0.3902 (4)	0.36258 (19)	0.11620 (10)	0.0702 (6)
H10	0.2956	0.3133	0.1050	0.084*
C11	0.5053 (4)	0.4034 (2)	0.07187 (11)	0.1001 (9)	0.50
H11	0.4894	0.3813	0.0312	0.120*	0.50
N11'	0.5053 (4)	0.4034 (2)	0.07187 (11)	0.1001 (9)	0.50
C12	0.6730 (3)	0.50749 (19)	0.14942 (10)	0.0689 (6)
H12	0.7683	0.5565	0.1603	0.083*
C13	0.5597 (3)	0.46512 (16)	0.19473 (8)	0.0515 (5)
C14	0.7485 (3)	0.51181 (15)	0.28101 (9)	0.0521 (5)
H14	0.8533	0.4996	0.2572	0.063*
C15	0.7808 (2)	0.54772 (15)	0.34332 (9)	0.0485 (5)
C16	0.9667 (3)	0.55853 (18)	0.36768 (11)	0.0627 (6)
H16	1.0688	0.5430	0.3433	0.075*
C17	0.9997 (3)	0.5914 (2)	0.42659 (11)	0.0709 (7)
H17	1.1240	0.5989	0.4420	0.085*
C18	0.8482 (3)	0.61378 (17)	0.46400 (10)	0.0633 (6)
H18	0.8720	0.6353	0.5044	0.076*
C19	0.6628 (3)	0.60425 (16)	0.44133 (9)	0.0520 (5)
C20	0.6280 (2)	0.57152 (15)	0.38063 (8)	0.0472 (5)
C21	0.5334 (4)	0.6494 (2)	0.53719 (9)	0.0768 (7)
H21A	0.4129	0.6523	0.5564	0.115*
H21B	0.5960	0.7178	0.5415	0.115*
H21C	0.6111	0.5945	0.5564	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0779 (10)	0.0898 (13)	0.0678 (10)	−0.0215 (9)	0.0158 (8)	0.0065 (9)
O2	0.0525 (9)	0.0842 (12)	0.0607 (10)	−0.0193 (8)	−0.0014 (7)	0.0059 (8)
O3	0.0394 (8)	0.0892 (12)	0.0515 (9)	−0.0003 (7)	0.0008 (6)	−0.0052 (8)
O4	0.0644 (9)	0.0838 (11)	0.0487 (8)	0.0036 (8)	0.0004 (7)	−0.0056 (7)
N1	0.0541 (10)	0.0470 (10)	0.0570 (10)	−0.0033 (8)	0.0018 (8)	−0.0013 (8)
N2	0.0500 (10)	0.0458 (9)	0.0534 (9)	−0.0033 (7)	0.0072 (7)	−0.0001 (8)
N3	0.129 (2)	0.096 (2)	0.0825 (17)	−0.0156 (17)	0.0349 (15)	−0.0109 (15)
C3'	0.129 (2)	0.096 (2)	0.0825 (17)	−0.0156 (17)	0.0349 (15)	−0.0109 (15)
C1	0.0445 (11)	0.0437 (11)	0.0695 (13)	−0.0052 (9)	0.0050 (10)	−0.0068 (10)
C2	0.0559 (13)	0.0515 (13)	0.0676 (14)	−0.0056 (10)	0.0099 (10)	−0.0070 (11)
C3	0.0560 (13)	0.0607 (14)	0.0922 (18)	−0.0128 (11)	0.0205 (12)	−0.0101 (13)
C4	0.0450 (12)	0.0626 (15)	0.112 (2)	−0.0091 (11)	0.0038 (13)	−0.0157 (14)
C5	0.0555 (14)	0.0581 (14)	0.0833 (15)	−0.0004 (11)	−0.0082 (11)	−0.0112 (12)
C6	0.0441 (11)	0.0423 (11)	0.0684 (13)	0.0003 (9)	−0.0001 (9)	−0.0065 (10)
C7	0.0589 (13)	0.0493 (12)	0.0606 (13)	0.0020 (10)	−0.0053 (10)	−0.0043 (10)
C8	0.098 (2)	0.100 (2)	0.0907 (19)	−0.0141 (17)	0.0287 (16)	0.0251 (17)
C9	0.0636 (13)	0.0434 (11)	0.0507 (11)	0.0008 (10)	0.0092 (9)	−0.0002 (9)
C10	0.0898 (17)	0.0616 (15)	0.0595 (13)	−0.0097 (13)	0.0084 (12)	−0.0112 (12)
C11	0.132 (2)	0.094 (2)	0.0760 (16)	−0.0124 (17)	0.0239 (16)	−0.0168 (14)
N11'	0.132 (2)	0.094 (2)	0.0760 (16)	−0.0124 (17)	0.0239 (16)	−0.0168 (14)
C12	0.0851 (16)	0.0618 (14)	0.0614 (14)	−0.0133 (12)	0.0244 (12)	−0.0056 (11)
C13	0.0591 (12)	0.0453 (11)	0.0508 (11)	0.0020 (10)	0.0116 (9)	−0.0025 (9)
C14	0.0482 (12)	0.0445 (11)	0.0646 (13)	0.0012 (9)	0.0145 (9)	0.0000 (10)
C15	0.0410 (10)	0.0425 (11)	0.0623 (12)	−0.0013 (8)	0.0033 (9)	0.0045 (9)
C16	0.0416 (11)	0.0653 (14)	0.0811 (16)	−0.0008 (10)	0.0004 (10)	0.0059 (12)
C17	0.0483 (13)	0.0760 (17)	0.0869 (17)	−0.0054 (11)	−0.0166 (12)	0.0081 (13)
C18	0.0650 (14)	0.0624 (14)	0.0611 (13)	−0.0055 (11)	−0.0163 (11)	0.0071 (11)
C19	0.0523 (12)	0.0508 (12)	0.0527 (12)	−0.0009 (9)	−0.0023 (9)	0.0055 (9)
C20	0.0402 (11)	0.0469 (11)	0.0541 (11)	−0.0033 (8)	−0.0032 (8)	0.0055 (9)
C21	0.1014 (18)	0.0795 (17)	0.0492 (13)	0.0021 (14)	0.0015 (12)	−0.0036 (12)

Geometric parameters (Å, º)

O1—C2	1.371 (2)	C8—H8A	0.9600
O1—C8	1.416 (3)	C8—H8B	0.9600
O2—C1	1.349 (2)	C8—H8C	0.9600
O2—H2O	0.869 (10)	C9—C10	1.396 (3)
O3—C20	1.358 (2)	C9—C13	1.397 (3)
O3—H3O	0.858 (9)	C10—C11	1.380 (3)
O4—C19	1.369 (2)	C10—H10	0.9300
O4—C21	1.421 (2)	C11—H11	0.9300
N1—C7	1.286 (2)	C12—C13	1.395 (3)
N1—C9	1.411 (2)	C12—H12	0.9300
N2—C14	1.280 (2)	C14—C15	1.439 (3)
N2—C13	1.409 (2)	C14—H14	0.9300
N3—C12	1.378 (3)	C15—C16	1.399 (3)
N3—C11	1.394 (4)	C15—C20	1.403 (2)
C1—C6	1.395 (3)	C16—C17	1.359 (3)
C1—C2	1.405 (3)	C16—H16	0.9300
C2—C3	1.374 (3)	C17—C18	1.394 (3)
C3—C4	1.383 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.382 (3)
C4—C5	1.359 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.396 (3)
C5—C6	1.403 (3)	C21—H21A	0.9600
C5—H5	0.9300	C21—H21B	0.9600
C6—C7	1.442 (3)	C21—H21C	0.9600
C7—H7	0.9300
C2—O1—C8	118.02 (19)	C11—C10—H10	119.4
C1—O2—H2O	104.9 (17)	C9—C10—H10	119.4
C20—O3—H3O	106.0 (16)	C10—C11—N3	119.2 (2)
C19—O4—C21	116.76 (16)	C10—C11—H11	120.4
C7—N1—C9	120.52 (17)	N3—C11—H11	120.4
C14—N2—C13	120.35 (16)	N3—C12—C13	121.1 (2)
C12—N3—C11	120.1 (2)	N3—C12—H12	119.5
O2—C1—C6	122.45 (18)	C13—C12—H12	119.5
O2—C1—C2	117.88 (19)	C12—C13—C9	118.94 (18)
C6—C1—C2	119.67 (18)	C12—C13—N2	122.04 (18)
O1—C2—C3	125.3 (2)	C9—C13—N2	118.94 (16)
O1—C2—C1	115.12 (18)	N2—C14—C15	123.11 (17)
C3—C2—C1	119.6 (2)	N2—C14—H14	118.4
C2—C3—C4	120.6 (2)	C15—C14—H14	118.4
C2—C3—H3	119.7	C16—C15—C20	119.02 (18)
C4—C3—H3	119.7	C16—C15—C14	120.04 (17)
C5—C4—C3	120.6 (2)	C20—C15—C14	120.94 (16)
C5—C4—H4	119.7	C17—C16—C15	120.8 (2)
C3—C4—H4	119.7	C17—C16—H16	119.6
C4—C5—C6	120.4 (2)	C15—C16—H16	119.6
C4—C5—H5	119.8	C16—C17—C18	120.3 (2)
C6—C5—H5	119.8	C16—C17—H17	119.8
C1—C6—C5	119.15 (19)	C18—C17—H17	119.8
C1—C6—C7	121.31 (18)	C19—C18—C17	120.4 (2)
C5—C6—C7	119.52 (19)	C19—C18—H18	119.8
N1—C7—C6	122.67 (19)	C17—C18—H18	119.8
N1—C7—H7	118.7	O4—C19—C18	125.21 (18)
C6—C7—H7	118.7	O4—C19—C20	115.26 (16)
O1—C8—H8A	109.5	C18—C19—C20	119.53 (19)
O1—C8—H8B	109.5	O3—C20—C19	117.99 (17)
H8A—C8—H8B	109.5	O3—C20—C15	122.06 (17)
O1—C8—H8C	109.5	C19—C20—C15	119.94 (17)
H8A—C8—H8C	109.5	O4—C21—H21A	109.5
H8B—C8—H8C	109.5	O4—C21—H21B	109.5
C10—C9—C13	119.42 (18)	H21A—C21—H21B	109.5
C10—C9—N1	122.43 (19)	O4—C21—H21C	109.5
C13—C9—N1	118.05 (17)	H21A—C21—H21C	109.5
C11—C10—C9	121.2 (2)	H21B—C21—H21C	109.5
C8—O1—C2—C3	3.9 (3)	N3—C12—C13—N2	−178.6 (2)
C8—O1—C2—C1	−175.8 (2)	C10—C9—C13—C12	3.5 (3)
O2—C1—C2—O1	−1.3 (3)	N1—C9—C13—C12	179.96 (18)
C6—C1—C2—O1	177.97 (18)	C10—C9—C13—N2	−179.67 (19)
O2—C1—C2—C3	179.09 (19)	N1—C9—C13—N2	−3.2 (3)
C6—C1—C2—C3	−1.7 (3)	C14—N2—C13—C12	−38.6 (3)
O1—C2—C3—C4	−178.6 (2)	C14—N2—C13—C9	144.74 (19)
C1—C2—C3—C4	1.0 (3)	C13—N2—C14—C15	177.30 (17)
C2—C3—C4—C5	0.4 (4)	N2—C14—C15—C16	176.97 (19)
C3—C4—C5—C6	−1.0 (3)	N2—C14—C15—C20	−2.5 (3)
O2—C1—C6—C5	−179.75 (18)	C20—C15—C16—C17	0.1 (3)
C2—C1—C6—C5	1.1 (3)	C14—C15—C16—C17	−179.4 (2)
O2—C1—C6—C7	−0.9 (3)	C15—C16—C17—C18	0.7 (3)
C2—C1—C6—C7	179.87 (18)	C16—C17—C18—C19	−0.9 (3)
C4—C5—C6—C1	0.3 (3)	C21—O4—C19—C18	−5.6 (3)
C4—C5—C6—C7	−178.6 (2)	C21—O4—C19—C20	174.69 (19)
C9—N1—C7—C6	177.91 (17)	C17—C18—C19—O4	−179.4 (2)
C1—C6—C7—N1	1.0 (3)	C17—C18—C19—C20	0.2 (3)
C5—C6—C7—N1	179.81 (19)	O4—C19—C20—O3	−0.1 (3)
C7—N1—C9—C10	−29.9 (3)	C18—C19—C20—O3	−179.78 (18)
C7—N1—C9—C13	153.82 (19)	O4—C19—C20—C15	−179.73 (17)
C13—C9—C10—C11	−2.3 (4)	C18—C19—C20—C15	0.5 (3)
N1—C9—C10—C11	−178.6 (2)	C16—C15—C20—O3	179.61 (18)
C9—C10—C11—N3	−0.5 (4)	C14—C15—C20—O3	−0.9 (3)
C12—N3—C11—C10	2.2 (4)	C16—C15—C20—C19	−0.7 (3)
C11—N3—C12—C13	−1.0 (4)	C14—C15—C20—C19	178.76 (18)
N3—C12—C13—C9	−1.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N1	0.87 (1)	1.82 (2)	2.621 (2)	152 (2)
O3—H3O···N2	0.86 (1)	1.83 (1)	2.615 (2)	151 (2)