2-((E)-{[3-(1H-Imidazol-1-yl)prop­yl]imino}­meth­yl)-4-[(E)-(2-methyl­phen­yl)diazen­yl]phenol

In the title compound, C₂₀H₂₁N₅O, an intra­molecular O—H...N hydrogen bond forms between the –OH substituent of the phenol ring and the adjacent imino­methyl N atom, enclosing an S6 ring. The dihedral angles between the imidazole ring and the methyl­phenyl and phenol rings are 86.93 (14) and 88.00 (13)°, respectively, while that between the methyl­phenyl and phenol rings is 2.18 (12)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.105
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.400
           From the CIF: _refine_ls_abs_structure_Flack_su    0.400
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.400 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.17 Check
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          4 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2-((E)-{[3-(1H-Imidazol-1-yl)propyl]imino}methyl)-4-[(E)-(2-methylphenyl)diazenyl]phenol

Crystal data

C20H21N5O	Dx = 1.258 Mg m^−3
Mr = 347.42	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 245 reflections
a = 9.7570 (3) Å	θ = 0.2–52°
b = 32.0691 (13) Å	µ = 0.08 mm^−1
c = 5.8643 (2) Å	T = 293 K
V = 1834.93 (11) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.12 mm
F(000) = 736

Data collection

Bruker APEXII CCD detector diffractometer	2978 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 26.0°, θmin = 1.3°
ω and φ scans	h = −12→11
25352 measured reflections	k = −39→39
3590 independent reflections	l = −7→7

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0669P)^2 + 0.0698P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.037	(Δ/σ)max < 0.001
wR(F^2) = 0.105	Δρmax = 0.18 e Å^−3
S = 1.04	Δρmin = −0.16 e Å^−3
3590 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
238 parameters	Extinction coefficient: 0.011 (3)
0 restraints	Absolute structure: Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: −0.4 (4)

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.

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

	x	y	z	Uiso*/Ueq
C12	0.3769 (2)	0.07393 (7)	0.3773 (4)	0.0467 (5)
H12	0.4141	0.0641	0.2415	0.056*
O1	0.41943 (18)	0.15905 (5)	0.7861 (3)	0.0678 (5)
H1	0.4841	0.1685	0.7134	0.102*
C11	0.4278 (2)	0.11065 (6)	0.4741 (4)	0.0418 (5)
C13	0.5404 (2)	0.13322 (7)	0.3685 (4)	0.0469 (5)
H13	0.5787	0.1233	0.2339	0.056*
N1	0.26508 (19)	−0.00103 (6)	0.2286 (3)	0.0531 (5)
N3	0.58696 (18)	0.16637 (5)	0.4584 (3)	0.0494 (5)
C8	0.2161 (2)	0.06705 (7)	0.6845 (4)	0.0555 (6)
H8	0.1450	0.0525	0.7539	0.067*
N2	0.2132 (2)	0.01415 (6)	0.4030 (3)	0.0541 (5)
C6	0.2023 (2)	−0.03952 (7)	0.1584 (4)	0.0489 (5)
C14	0.7004 (2)	0.18966 (7)	0.3569 (4)	0.0503 (6)
H14A	0.6653	0.2138	0.2761	0.060*
H14B	0.7487	0.1722	0.2484	0.060*
C9	0.2645 (2)	0.10291 (7)	0.7834 (4)	0.0563 (6)
H9	0.2260	0.1125	0.9186	0.068*
C7	0.2719 (2)	0.05208 (7)	0.4815 (4)	0.0471 (5)
C1	0.2536 (2)	−0.05815 (7)	−0.0377 (4)	0.0507 (6)
C5	0.0958 (3)	−0.05797 (8)	0.2794 (5)	0.0662 (7)
H5	0.0629	−0.0454	0.4115	0.079*
N4	0.99745 (18)	0.22455 (5)	0.3059 (3)	0.0441 (4)
C10	0.3715 (2)	0.12496 (6)	0.6814 (4)	0.0478 (5)
C17	1.1092 (2)	0.20035 (7)	0.3481 (4)	0.0542 (6)
H17	1.1344	0.1885	0.4866	0.065*
C20	0.3712 (3)	−0.03963 (9)	−0.1689 (5)	0.0686 (7)
H20A	0.3643	−0.0098	−0.1669	0.103*
H20B	0.3684	−0.0494	−0.3236	0.103*
H20C	0.4562	−0.0480	−0.0998	0.103*
C3	0.0873 (3)	−0.11327 (8)	0.0100 (6)	0.0672 (7)
H3	0.0485	−0.1380	−0.0415	0.081*
C16	0.8941 (2)	0.23810 (7)	0.4694 (4)	0.0552 (6)
H16A	0.8410	0.2605	0.4022	0.066*
H16B	0.9397	0.2491	0.6034	0.066*
C19	1.1760 (3)	0.19709 (8)	0.1467 (5)	0.0622 (7)
H19	1.2566	0.1822	0.1248	0.075*
C18	1.0022 (3)	0.23486 (8)	0.0844 (4)	0.0596 (6)
H18	0.9374	0.2516	0.0123	0.072*
C15	0.7975 (2)	0.20352 (7)	0.5421 (4)	0.0538 (6)
H15A	0.8512	0.1797	0.5914	0.065*
H15B	0.7443	0.2131	0.6718	0.065*
N5	1.1094 (2)	0.21854 (8)	−0.0191 (4)	0.0712 (6)
C4	0.0388 (3)	−0.09479 (8)	0.2045 (6)	0.0714 (8)
H4	−0.0325	−0.1071	0.2857	0.086*
C2	0.1933 (3)	−0.09525 (7)	−0.1093 (5)	0.0618 (7)
H2	0.2254	−0.1082	−0.2408	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C12	0.0489 (11)	0.0477 (11)	0.0437 (11)	0.0006 (10)	−0.0008 (10)	−0.0074 (10)
O1	0.0660 (11)	0.0584 (10)	0.0792 (12)	−0.0179 (8)	0.0269 (10)	−0.0315 (9)
C11	0.0404 (11)	0.0399 (10)	0.0451 (11)	0.0019 (8)	0.0003 (9)	−0.0026 (9)
C13	0.0470 (12)	0.0482 (11)	0.0456 (11)	0.0012 (10)	0.0048 (10)	−0.0057 (10)
N1	0.0543 (11)	0.0472 (10)	0.0579 (11)	−0.0060 (9)	−0.0022 (9)	−0.0101 (9)
N3	0.0454 (10)	0.0446 (10)	0.0581 (11)	−0.0036 (8)	0.0082 (9)	−0.0046 (8)
C8	0.0496 (12)	0.0528 (13)	0.0641 (15)	−0.0096 (11)	0.0106 (13)	−0.0070 (11)
N2	0.0536 (10)	0.0492 (11)	0.0595 (12)	−0.0063 (9)	−0.0010 (10)	−0.0111 (9)
C6	0.0450 (11)	0.0439 (11)	0.0577 (14)	−0.0012 (10)	−0.0072 (11)	−0.0080 (10)
C14	0.0494 (12)	0.0492 (12)	0.0524 (13)	−0.0049 (10)	0.0098 (11)	−0.0001 (10)
C9	0.0542 (14)	0.0571 (14)	0.0577 (14)	−0.0081 (11)	0.0152 (12)	−0.0164 (11)
C7	0.0454 (11)	0.0441 (11)	0.0517 (12)	−0.0043 (10)	−0.0044 (11)	−0.0041 (10)
C1	0.0504 (12)	0.0459 (11)	0.0557 (13)	0.0054 (10)	−0.0091 (11)	−0.0050 (10)
C5	0.0625 (14)	0.0585 (14)	0.0775 (18)	−0.0102 (12)	0.0078 (15)	−0.0180 (13)
N4	0.0449 (9)	0.0440 (9)	0.0435 (9)	−0.0058 (8)	0.0065 (9)	−0.0005 (8)
C10	0.0427 (11)	0.0439 (12)	0.0568 (13)	−0.0009 (9)	0.0031 (11)	−0.0103 (10)
C17	0.0508 (12)	0.0512 (12)	0.0606 (14)	−0.0055 (11)	−0.0064 (12)	0.0033 (11)
C20	0.0768 (17)	0.0621 (15)	0.0668 (16)	0.0011 (13)	0.0108 (15)	−0.0055 (13)
C3	0.0579 (14)	0.0482 (13)	0.096 (2)	−0.0028 (12)	−0.0175 (16)	−0.0191 (14)
C16	0.0547 (13)	0.0569 (14)	0.0539 (13)	−0.0120 (11)	0.0166 (12)	−0.0108 (11)
C19	0.0528 (13)	0.0512 (13)	0.0827 (19)	−0.0042 (11)	0.0115 (14)	−0.0136 (13)
C18	0.0678 (15)	0.0632 (15)	0.0480 (13)	0.0051 (13)	0.0092 (13)	0.0098 (11)
C15	0.0531 (12)	0.0587 (14)	0.0496 (13)	−0.0088 (11)	0.0104 (11)	0.0029 (11)
N5	0.0828 (15)	0.0772 (14)	0.0535 (12)	−0.0035 (13)	0.0235 (13)	−0.0049 (11)
C4	0.0605 (15)	0.0572 (15)	0.097 (2)	−0.0141 (12)	0.0049 (15)	−0.0138 (15)
C2	0.0670 (15)	0.0505 (13)	0.0679 (17)	0.0053 (12)	−0.0091 (14)	−0.0165 (12)

Geometric parameters (Å, º)

C12—C7	1.383 (3)	C5—C4	1.377 (3)
C12—C11	1.398 (3)	C5—H5	0.9300
C12—H12	0.9300	N4—C18	1.341 (3)
O1—C10	1.338 (3)	N4—C17	1.361 (3)
O1—H1	0.8200	N4—C16	1.458 (3)
C11—C10	1.410 (3)	C17—C19	1.353 (4)
C11—C13	1.454 (3)	C17—H17	0.9300
C13—N3	1.271 (3)	C20—H20A	0.9600
C13—H13	0.9300	C20—H20B	0.9600
N1—N2	1.240 (3)	C20—H20C	0.9600
N1—C6	1.439 (3)	C3—C4	1.370 (4)
N3—C14	1.462 (3)	C3—C2	1.376 (4)
C8—C9	1.372 (3)	C3—H3	0.9300
C8—C7	1.395 (3)	C16—C15	1.517 (3)
C8—H8	0.9300	C16—H16A	0.9700
N2—C7	1.421 (3)	C16—H16B	0.9700
C6—C1	1.389 (3)	C19—N5	1.357 (4)
C6—C5	1.390 (3)	C19—H19	0.9300
C14—C15	1.508 (3)	C18—N5	1.317 (3)
C14—H14A	0.9700	C18—H18	0.9300
C14—H14B	0.9700	C15—H15A	0.9700
C9—C10	1.396 (3)	C15—H15B	0.9700
C9—H9	0.9300	C4—H4	0.9300
C1—C2	1.392 (3)	C2—H2	0.9300
C1—C20	1.504 (4)
C7—C12—C11	120.7 (2)	O1—C10—C9	118.6 (2)
C7—C12—H12	119.7	O1—C10—C11	121.68 (19)
C11—C12—H12	119.7	C9—C10—C11	119.74 (19)
C10—O1—H1	109.5	C19—C17—N4	105.7 (2)
C12—C11—C10	119.04 (19)	C19—C17—H17	127.1
C12—C11—C13	120.97 (19)	N4—C17—H17	127.1
C10—C11—C13	119.95 (19)	C1—C20—H20A	109.5
N3—C13—C11	120.7 (2)	C1—C20—H20B	109.5
N3—C13—H13	119.7	H20A—C20—H20B	109.5
C11—C13—H13	119.7	C1—C20—H20C	109.5
N2—N1—C6	113.5 (2)	H20A—C20—H20C	109.5
C13—N3—C14	121.94 (19)	H20B—C20—H20C	109.5
C9—C8—C7	121.0 (2)	C4—C3—C2	120.1 (2)
C9—C8—H8	119.5	C4—C3—H3	120.0
C7—C8—H8	119.5	C2—C3—H3	120.0
N1—N2—C7	115.98 (19)	N4—C16—C15	113.40 (19)
C1—C6—C5	120.6 (2)	N4—C16—H16A	108.9
C1—C6—N1	116.9 (2)	C15—C16—H16A	108.9
C5—C6—N1	122.5 (2)	N4—C16—H16B	108.9
N3—C14—C15	109.41 (19)	C15—C16—H16B	108.9
N3—C14—H14A	109.8	H16A—C16—H16B	107.7
C15—C14—H14A	109.8	C17—C19—N5	110.8 (2)
N3—C14—H14B	109.8	C17—C19—H19	124.6
C15—C14—H14B	109.8	N5—C19—H19	124.6
H14A—C14—H14B	108.2	N5—C18—N4	112.1 (3)
C8—C9—C10	120.1 (2)	N5—C18—H18	124.0
C8—C9—H9	120.0	N4—C18—H18	124.0
C10—C9—H9	120.0	C14—C15—C16	113.8 (2)
C12—C7—C8	119.5 (2)	C14—C15—H15A	108.8
C12—C7—N2	126.1 (2)	C16—C15—H15A	108.8
C8—C7—N2	114.4 (2)	C14—C15—H15B	108.8
C6—C1—C2	117.7 (2)	C16—C15—H15B	108.8
C6—C1—C20	121.9 (2)	H15A—C15—H15B	107.7
C2—C1—C20	120.4 (2)	C18—N5—C19	104.6 (2)
C4—C5—C6	120.2 (3)	C3—C4—C5	119.8 (3)
C4—C5—H5	119.9	C3—C4—H4	120.1
C6—C5—H5	119.9	C5—C4—H4	120.1
C18—N4—C17	106.8 (2)	C3—C2—C1	121.6 (2)
C18—N4—C16	126.0 (2)	C3—C2—H2	119.2
C17—N4—C16	127.2 (2)	C1—C2—H2	119.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.82	1.80	2.534 (2)	148