6,6′-[(1E,1′E)-Oxybis(4,1-phenyl­ene)bis­(aza­nylyl­idene)bis­(methanylyl­idene)]bis­(2-methyl­phenol): supra­molecular assemblies in two dimensions mediated by weak C—H...N, C—H...O and C—H...π inter­actions

The title compound is a flexible Schiff base, as illustrated by its dihedral angles. The sp²-hybridized character of the aza­nylyl­idene groups is confirmed by their bond lengths and bond angles. In the crystal, mol­ecules of the title compound are assembled into two-dimensional networks connected by weak C—H...O, C—H...N and C—H...π inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.131
• Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A      ..O1               2.72 Ang.

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         50 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         23 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

6,6'-[(1E,1'E)-Oxybis(4,1-phenylene)bis(azanylylidene)bis(methanylylidene)]bis(2-methylphenol)

Crystal data

C28H24N2O3	Z = 2
Mr = 436.49	F(000) = 460
Triclinic, P1	Dx = 1.331 Mg m^−3
a = 10.2293 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9623 (4) Å	Cell parameters from 9984 reflections
c = 11.3087 (4) Å	θ = 2.2–30.2°
α = 108.5568 (10)°	µ = 0.09 mm^−1
β = 96.7616 (10)°	T = 100 K
γ = 110.4087 (10)°	Block, yellow
V = 1088.76 (7) Å^3	0.35 × 0.31 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer	6513 independent reflections
Radiation source: fine-focus sealed tube	5433 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 30.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −14→14
Tmin = 0.903, Tmax = 0.960	k = −15→15
42726 measured reflections	l = −16→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.3053P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6513 reflections	Δρmax = 0.38 e Å^−3
308 parameters	Δρmin = −0.32 e Å^−3

Special details

Experimental. The following wavelength and cell were deduced by SADABS from the direction cosines etc. They are given here for emergency use only: CELL 0.71062 10.322 11.055 11.397 108.521 96.732 110.436

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
O1	0.76527 (8)	0.48598 (7)	0.45322 (7)	0.01951 (16)
O2	1.54997 (8)	1.09474 (8)	0.70552 (7)	0.02197 (16)
O3	0.06378 (8)	0.07922 (8)	0.64561 (7)	0.02142 (16)
N1	1.29823 (9)	0.93739 (9)	0.71785 (9)	0.01841 (17)
N2	0.32630 (9)	0.26192 (9)	0.67203 (8)	0.01845 (17)
C1	1.57792 (11)	1.16561 (10)	0.83396 (10)	0.01812 (19)
C2	1.70943 (11)	1.28524 (11)	0.89546 (11)	0.0208 (2)
C3	1.73960 (11)	1.35727 (11)	1.02776 (11)	0.0237 (2)
H3A	1.8280	1.4382	1.0703	0.028*
C4	1.64482 (12)	1.31511 (11)	1.10050 (11)	0.0237 (2)
H4A	1.6693	1.3654	1.1912	0.028*
C5	1.51434 (11)	1.19879 (11)	1.03847 (10)	0.0218 (2)
H5A	1.4485	1.1701	1.0870	0.026*
C6	1.47866 (11)	1.12316 (10)	0.90474 (10)	0.01809 (19)
C7	1.33802 (11)	1.00598 (11)	0.84107 (10)	0.01925 (19)
H7A	1.2739	0.9794	0.8916	0.023*
C8	1.16198 (10)	0.82216 (10)	0.65723 (10)	0.01726 (19)
C9	1.09958 (11)	0.79317 (10)	0.52934 (10)	0.01908 (19)
H9A	1.1491	0.8497	0.4867	0.023*
C10	0.96575 (11)	0.68236 (10)	0.46405 (10)	0.01876 (19)
H10A	0.9225	0.6645	0.3778	0.023*
C11	0.89561 (10)	0.59785 (10)	0.52567 (9)	0.01665 (18)
C12	0.95985 (10)	0.62060 (10)	0.65062 (10)	0.01793 (19)
H12A	0.9136	0.5592	0.6905	0.022*
C13	1.09192 (10)	0.73371 (10)	0.71658 (10)	0.01777 (19)
H13A	1.1350	0.7511	0.8028	0.021*
C14	0.66246 (10)	0.43684 (10)	0.51590 (9)	0.01645 (18)
C15	0.57873 (10)	0.29247 (10)	0.46457 (10)	0.01831 (19)
H15A	0.5973	0.2321	0.3937	0.022*
C16	0.46798 (11)	0.23692 (10)	0.51734 (10)	0.01851 (19)
H16A	0.4099	0.1383	0.4817	0.022*
C17	0.44103 (10)	0.32475 (10)	0.62243 (9)	0.01667 (18)
C18	0.52465 (10)	0.47018 (10)	0.67105 (9)	0.01735 (19)
H18A	0.5059	0.5310	0.7414	0.021*
C19	0.63458 (10)	0.52671 (10)	0.61781 (9)	0.01706 (19)
H19A	0.6902	0.6257	0.6506	0.020*
C20	0.33650 (11)	0.31399 (11)	0.79342 (10)	0.01902 (19)
H20A	0.4225	0.3926	0.8481	0.023*
C21	0.22143 (10)	0.25721 (10)	0.85028 (9)	0.01744 (19)
C22	0.24188 (11)	0.31750 (11)	0.98398 (10)	0.0217 (2)
H22A	0.3289	0.3969	1.0353	0.026*
C23	0.13736 (12)	0.26316 (12)	1.04218 (11)	0.0247 (2)
H23A	0.1518	0.3047	1.1329	0.030*
C24	0.01010 (12)	0.14628 (12)	0.96590 (11)	0.0237 (2)
H24A	−0.0613	0.1085	1.0064	0.028*
C25	−0.01556 (11)	0.08364 (11)	0.83349 (10)	0.0201 (2)
C26	0.09098 (11)	0.14035 (10)	0.77475 (9)	0.01703 (18)
C27	1.81029 (12)	1.33195 (13)	0.81651 (12)	0.0279 (2)
H27A	1.7559	1.3335	0.7401	0.042*
H27B	1.8558	1.2660	0.7894	0.042*
H27C	1.8849	1.4267	0.8686	0.042*
C28	−0.15322 (12)	−0.04094 (12)	0.75086 (12)	0.0289 (2)
H28A	−0.1306	−0.1120	0.6897	0.043*
H28B	−0.2132	−0.0103	0.7032	0.043*
H28C	−0.2056	−0.0817	0.8058	0.043*
H1O3	0.153 (2)	0.131 (2)	0.6250 (18)	0.052 (5)*
H1O2	1.458 (2)	1.027 (2)	0.6813 (19)	0.056 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0152 (3)	0.0190 (3)	0.0165 (3)	0.0016 (3)	0.0049 (3)	0.0028 (3)
O2	0.0198 (4)	0.0216 (4)	0.0199 (4)	0.0045 (3)	0.0050 (3)	0.0068 (3)
O3	0.0221 (4)	0.0196 (3)	0.0162 (3)	0.0042 (3)	0.0033 (3)	0.0043 (3)
N1	0.0148 (4)	0.0158 (4)	0.0220 (4)	0.0048 (3)	0.0036 (3)	0.0060 (3)
N2	0.0165 (4)	0.0193 (4)	0.0205 (4)	0.0071 (3)	0.0064 (3)	0.0086 (3)
C1	0.0165 (4)	0.0169 (4)	0.0213 (5)	0.0074 (4)	0.0037 (4)	0.0075 (4)
C2	0.0165 (4)	0.0184 (4)	0.0269 (5)	0.0066 (4)	0.0030 (4)	0.0097 (4)
C3	0.0169 (4)	0.0191 (5)	0.0290 (5)	0.0056 (4)	−0.0009 (4)	0.0060 (4)
C4	0.0219 (5)	0.0230 (5)	0.0216 (5)	0.0105 (4)	0.0006 (4)	0.0032 (4)
C5	0.0197 (5)	0.0234 (5)	0.0217 (5)	0.0104 (4)	0.0045 (4)	0.0066 (4)
C6	0.0162 (4)	0.0169 (4)	0.0203 (5)	0.0069 (3)	0.0039 (4)	0.0062 (4)
C7	0.0153 (4)	0.0178 (4)	0.0239 (5)	0.0061 (4)	0.0059 (4)	0.0075 (4)
C8	0.0139 (4)	0.0155 (4)	0.0208 (5)	0.0056 (3)	0.0048 (3)	0.0053 (4)
C9	0.0192 (4)	0.0176 (4)	0.0200 (5)	0.0062 (4)	0.0068 (4)	0.0076 (4)
C10	0.0192 (4)	0.0191 (4)	0.0169 (4)	0.0075 (4)	0.0047 (4)	0.0060 (4)
C11	0.0137 (4)	0.0152 (4)	0.0180 (4)	0.0052 (3)	0.0043 (3)	0.0032 (3)
C12	0.0165 (4)	0.0178 (4)	0.0199 (5)	0.0067 (4)	0.0057 (4)	0.0077 (4)
C13	0.0163 (4)	0.0190 (4)	0.0183 (4)	0.0076 (4)	0.0042 (3)	0.0071 (4)
C14	0.0135 (4)	0.0183 (4)	0.0158 (4)	0.0053 (3)	0.0038 (3)	0.0057 (3)
C15	0.0175 (4)	0.0171 (4)	0.0171 (4)	0.0067 (4)	0.0042 (3)	0.0032 (4)
C16	0.0171 (4)	0.0156 (4)	0.0192 (4)	0.0046 (3)	0.0035 (3)	0.0048 (4)
C17	0.0136 (4)	0.0185 (4)	0.0165 (4)	0.0056 (3)	0.0031 (3)	0.0064 (3)
C18	0.0165 (4)	0.0175 (4)	0.0166 (4)	0.0069 (3)	0.0037 (3)	0.0049 (3)
C19	0.0151 (4)	0.0150 (4)	0.0172 (4)	0.0045 (3)	0.0027 (3)	0.0039 (3)
C20	0.0154 (4)	0.0183 (4)	0.0207 (5)	0.0052 (3)	0.0035 (3)	0.0066 (4)
C21	0.0166 (4)	0.0173 (4)	0.0173 (4)	0.0064 (3)	0.0039 (3)	0.0060 (4)
C22	0.0203 (5)	0.0204 (5)	0.0190 (5)	0.0053 (4)	0.0030 (4)	0.0048 (4)
C23	0.0264 (5)	0.0266 (5)	0.0183 (5)	0.0094 (4)	0.0069 (4)	0.0064 (4)
C24	0.0226 (5)	0.0252 (5)	0.0245 (5)	0.0083 (4)	0.0104 (4)	0.0113 (4)
C25	0.0177 (4)	0.0179 (4)	0.0228 (5)	0.0054 (4)	0.0046 (4)	0.0078 (4)
C26	0.0174 (4)	0.0156 (4)	0.0176 (4)	0.0071 (3)	0.0035 (3)	0.0058 (3)
C27	0.0200 (5)	0.0257 (5)	0.0348 (6)	0.0039 (4)	0.0055 (4)	0.0142 (5)
C28	0.0216 (5)	0.0248 (5)	0.0303 (6)	0.0009 (4)	0.0042 (4)	0.0089 (5)

Geometric parameters (Å, º)

O1—C11	1.3841 (11)	C12—H12A	0.9500
O1—C14	1.3864 (11)	C13—H13A	0.9500
O2—C1	1.3506 (13)	C14—C15	1.3885 (13)
O2—H1O2	0.91 (2)	C14—C19	1.3895 (13)
O3—C26	1.3456 (12)	C15—C16	1.3855 (14)
O3—H1O3	0.988 (19)	C15—H15A	0.9500
N1—C7	1.2880 (14)	C16—C17	1.3962 (14)
N1—C8	1.4156 (12)	C16—H16A	0.9500
N2—C20	1.2834 (13)	C17—C18	1.3985 (13)
N2—C17	1.4154 (12)	C18—C19	1.3864 (13)
C1—C2	1.4078 (14)	C18—H18A	0.9500
C1—C6	1.4097 (14)	C19—H19A	0.9500
C2—C3	1.3880 (16)	C20—C21	1.4521 (14)
C2—C27	1.5045 (15)	C20—H20A	0.9500
C3—C4	1.3956 (16)	C21—C22	1.3998 (14)
C3—H3A	0.9500	C21—C26	1.4122 (13)
C4—C5	1.3866 (15)	C22—C23	1.3792 (15)
C4—H4A	0.9500	C22—H22A	0.9500
C5—C6	1.4030 (14)	C23—C24	1.3962 (15)
C5—H5A	0.9500	C23—H23A	0.9500
C6—C7	1.4549 (14)	C24—C25	1.3819 (15)
C7—H7A	0.9500	C24—H24A	0.9500
C8—C13	1.3954 (14)	C25—C26	1.4058 (14)
C8—C9	1.3960 (14)	C25—C28	1.5027 (15)
C9—C10	1.3879 (14)	C27—H27A	0.9800
C9—H9A	0.9500	C27—H27B	0.9800
C10—C11	1.3870 (14)	C27—H27C	0.9800
C10—H10A	0.9500	C28—H28A	0.9800
C11—C12	1.3905 (14)	C28—H28B	0.9800
C12—C13	1.3874 (13)	C28—H28C	0.9800
C11—O1—C14	118.92 (7)	C16—C15—H15A	120.2
C1—O2—H1O2	105.6 (12)	C14—C15—H15A	120.2
C26—O3—H1O3	104.7 (11)	C15—C16—C17	120.52 (9)
C7—N1—C8	121.11 (9)	C15—C16—H16A	119.7
C20—N2—C17	119.51 (9)	C17—C16—H16A	119.7
O2—C1—C2	117.80 (9)	C16—C17—C18	118.95 (9)
O2—C1—C6	121.55 (9)	C16—C17—N2	117.94 (9)
C2—C1—C6	120.64 (9)	C18—C17—N2	123.08 (9)
C3—C2—C1	118.03 (10)	C19—C18—C17	120.84 (9)
C3—C2—C27	122.46 (10)	C19—C18—H18A	119.6
C1—C2—C27	119.49 (10)	C17—C18—H18A	119.6
C2—C3—C4	122.38 (10)	C18—C19—C14	119.21 (9)
C2—C3—H3A	118.8	C18—C19—H19A	120.4
C4—C3—H3A	118.8	C14—C19—H19A	120.4
C5—C4—C3	119.06 (10)	N2—C20—C21	122.42 (9)
C5—C4—H4A	120.5	N2—C20—H20A	118.8
C3—C4—H4A	120.5	C21—C20—H20A	118.8
C4—C5—C6	120.60 (10)	C22—C21—C26	119.10 (9)
C4—C5—H5A	119.7	C22—C21—C20	119.12 (9)
C6—C5—H5A	119.7	C26—C21—C20	121.75 (9)
C5—C6—C1	119.24 (9)	C23—C22—C21	120.85 (10)
C5—C6—C7	119.47 (9)	C23—C22—H22A	119.6
C1—C6—C7	121.25 (9)	C21—C22—H22A	119.6
N1—C7—C6	121.63 (9)	C22—C23—C24	119.09 (10)
N1—C7—H7A	119.2	C22—C23—H23A	120.5
C6—C7—H7A	119.2	C24—C23—H23A	120.5
C13—C8—C9	119.20 (9)	C25—C24—C23	122.23 (10)
C13—C8—N1	123.39 (9)	C25—C24—H24A	118.9
C9—C8—N1	117.33 (9)	C23—C24—H24A	118.9
C10—C9—C8	120.50 (9)	C24—C25—C26	118.34 (9)
C10—C9—H9A	119.7	C24—C25—C28	122.39 (10)
C8—C9—H9A	119.7	C26—C25—C28	119.27 (9)
C11—C10—C9	119.52 (9)	O3—C26—C25	117.66 (9)
C11—C10—H10A	120.2	O3—C26—C21	121.97 (9)
C9—C10—H10A	120.2	C25—C26—C21	120.37 (9)
O1—C11—C10	116.44 (9)	C2—C27—H27A	109.5
O1—C11—C12	122.74 (9)	C2—C27—H27B	109.5
C10—C11—C12	120.67 (9)	H27A—C27—H27B	109.5
C13—C12—C11	119.50 (9)	C2—C27—H27C	109.5
C13—C12—H12A	120.2	H27A—C27—H27C	109.5
C11—C12—H12A	120.2	H27B—C27—H27C	109.5
C12—C13—C8	120.47 (9)	C25—C28—H28A	109.5
C12—C13—H13A	119.8	C25—C28—H28B	109.5
C8—C13—H13A	119.8	H28A—C28—H28B	109.5
O1—C14—C15	116.46 (8)	C25—C28—H28C	109.5
O1—C14—C19	122.52 (9)	H28A—C28—H28C	109.5
C15—C14—C19	120.80 (9)	H28B—C28—H28C	109.5
C16—C15—C14	119.63 (9)
O2—C1—C2—C3	−179.09 (9)	C11—O1—C14—C15	−144.71 (9)
C6—C1—C2—C3	1.68 (14)	C11—O1—C14—C19	40.71 (13)
O2—C1—C2—C27	2.00 (14)	O1—C14—C15—C16	−176.07 (8)
C6—C1—C2—C27	−177.23 (9)	C19—C14—C15—C16	−1.39 (15)
C1—C2—C3—C4	0.05 (16)	C14—C15—C16—C17	−0.68 (15)
C27—C2—C3—C4	178.92 (10)	C15—C16—C17—C18	1.97 (15)
C2—C3—C4—C5	−1.33 (16)	C15—C16—C17—N2	179.91 (9)
C3—C4—C5—C6	0.88 (16)	C20—N2—C17—C16	146.74 (10)
C4—C5—C6—C1	0.80 (15)	C20—N2—C17—C18	−35.40 (14)
C4—C5—C6—C7	−176.86 (9)	C16—C17—C18—C19	−1.23 (14)
O2—C1—C6—C5	178.69 (9)	N2—C17—C18—C19	−179.06 (9)
C2—C1—C6—C5	−2.11 (14)	C17—C18—C19—C14	−0.79 (14)
O2—C1—C6—C7	−3.69 (15)	O1—C14—C19—C18	176.47 (9)
C2—C1—C6—C7	175.51 (9)	C15—C14—C19—C18	2.12 (15)
C8—N1—C7—C6	179.01 (9)	C17—N2—C20—C21	178.32 (9)
C5—C6—C7—N1	177.01 (9)	N2—C20—C21—C22	178.44 (10)
C1—C6—C7—N1	−0.61 (15)	N2—C20—C21—C26	0.19 (15)
C7—N1—C8—C13	−30.61 (15)	C26—C21—C22—C23	0.78 (16)
C7—N1—C8—C9	152.59 (10)	C20—C21—C22—C23	−177.52 (10)
C13—C8—C9—C10	3.47 (15)	C21—C22—C23—C24	0.16 (17)
N1—C8—C9—C10	−179.59 (9)	C22—C23—C24—C25	−0.62 (17)
C8—C9—C10—C11	−1.67 (15)	C23—C24—C25—C26	0.10 (16)
C14—O1—C11—C10	−152.24 (9)	C23—C24—C25—C28	−179.15 (11)
C14—O1—C11—C12	32.17 (13)	C24—C25—C26—O3	−179.28 (9)
C9—C10—C11—O1	−177.53 (8)	C28—C25—C26—O3	0.00 (14)
C9—C10—C11—C12	−1.84 (15)	C24—C25—C26—C21	0.87 (15)
O1—C11—C12—C13	178.90 (9)	C28—C25—C26—C21	−179.86 (9)
C10—C11—C12—C13	3.49 (15)	C22—C21—C26—O3	178.85 (9)
C11—C12—C13—C8	−1.64 (15)	C20—C21—C26—O3	−2.90 (15)
C9—C8—C13—C12	−1.80 (15)	C22—C21—C26—C25	−1.30 (15)
N1—C8—C13—C12	−178.55 (9)	C20—C21—C26—C25	176.95 (9)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2	0.99 (2)	1.73 (2)	2.6441 (13)	151.0 (17)
O2—H1O2···N1	0.91 (2)	1.76 (2)	2.6011 (13)	151.4 (18)
C15—H15A···N1^i	0.95	2.53	3.4211 (15)	156
C4—H4A···O1^ii	0.95	2.72	3.6626 (14)	171
C27—H27A···Cg1^iii	0.98	2.98	3.9242 (14)	162

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