Crystal structure, Hirshfeld surface analysis and anti­oxidant capacity of 2,2′-{(1E,1′E)-[1,2-phenyl­enebis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­(5-benz­yloxy)phenol

The title Schiff base compound was synthesized via the condensation reaction of 1,2-di­amine­benzene with 4-benz­yloxy-2-hy­droxy­benzaldehyde. The mol­ecule is V-shaped and possesses mirror symmetry; the mirror bis­ects the central benzene ring. There are two intra­molecular O—H...N hydrogen bonds present forming S(6) ring motifs.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.053
• wR factor = 0.158
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT073_ALERT_1_A H-atoms ref, but _hydrogen_treatment Reported as     constr Check

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.006 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         23 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         53 %
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0      0.996 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          4 Note

   1 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

2,2'-{(1E,1'E)-[1,2-Phenylenebis(azanylylidene)]bis(methanylylidene)}bis(5-benzyloxy)phenol

Crystal data

C34H28N2O4	F(000) = 1112
Mr = 528.58	Dx = 1.267 Mg m^−3
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 1621 reflections
a = 35.297 (3) Å	θ = 2.2–21.3°
b = 9.3902 (6) Å	µ = 0.08 mm^−1
c = 8.3603 (5) Å	T = 293 K
V = 2771.0 (3) Å^3	Block, yellow
Z = 4	0.03 × 0.02 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.042
Detector resolution: 18.4 pixels mm^-1	θmax = 27.5°, θmin = 3.7°
φ and ω scans	h = −45→40
4493 measured reflections	k = −12→5
2516 independent reflections	l = −10→6
1691 reflections with I > 2σ(I)

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)] = 0.053	Hydrogen site location: mixed
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0817P)^2] where P = (Fo^2 + 2Fc^2)/3
2516 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.29 e Å^−3
1 restraint	Δρmin = −0.24 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
O1	0.05052 (9)	0.2350 (3)	0.3234 (5)	0.0693 (13)
O2	0.15676 (8)	0.0288 (3)	0.5919 (4)	0.0546 (9)
N1	0.03881 (9)	0.5084 (4)	0.3640 (5)	0.0487 (10)
C1	0.01955 (13)	0.8879 (4)	0.2654 (7)	0.0639 (15)
C2	0.03890 (12)	0.7645 (4)	0.2985 (6)	0.0567 (14)
C3	0.01982 (11)	0.6379 (4)	0.3322 (5)	0.0481 (11)
C4	0.06841 (12)	0.5103 (4)	0.4519 (6)	0.0495 (14)
C5	0.09057 (11)	0.3828 (4)	0.4833 (5)	0.0454 (11)
C6	0.08042 (11)	0.2506 (4)	0.4207 (5)	0.0475 (11)
C7	0.10168 (11)	0.1285 (4)	0.4566 (5)	0.0488 (11)
C8	0.13349 (11)	0.1401 (4)	0.5523 (5)	0.0463 (12)
C9	0.14420 (12)	0.2710 (4)	0.6146 (6)	0.0560 (16)
C10	0.12269 (12)	0.3889 (4)	0.5813 (5)	0.0560 (16)
C11	0.14781 (12)	−0.1086 (4)	0.5260 (6)	0.0547 (16)
C12	0.17886 (11)	−0.2104 (4)	0.5695 (5)	0.0449 (11)
C13	0.17544 (12)	−0.2993 (4)	0.6998 (6)	0.0543 (16)
C14	0.20330 (16)	−0.3988 (4)	0.7345 (6)	0.0677 (17)
C15	0.23502 (14)	−0.4070 (5)	0.6404 (7)	0.0700 (19)
C16	0.23920 (14)	−0.3165 (6)	0.5124 (7)	0.0697 (17)
C17	0.21118 (13)	−0.2190 (5)	0.4765 (6)	0.0617 (17)
H1	0.03276	0.97121	0.24301	0.0770*
H1O	0.04038	0.31254	0.30933	0.1040*
H2	0.06524	0.76529	0.29851	0.0680*
H4	0.0777 (10)	0.604 (4)	0.509 (5)	0.041 (9)*
H7	0.09442	0.04030	0.41635	0.0580*
H9	0.16571	0.27872	0.67824	0.0670*
H10	0.12968	0.47594	0.62529	0.0670*
H11A	0.12385	−0.14214	0.56862	0.0660*
H11B	0.14557	−0.10203	0.41061	0.0660*
H13	0.15420	−0.29259	0.76516	0.0650*
H14	0.20047	−0.45974	0.82141	0.0810*
H15	0.25371	−0.47378	0.66311	0.0840*
H16	0.26095	−0.32099	0.44979	0.0840*
H17	0.21407	−0.15860	0.38915	0.0740*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0640 (19)	0.0400 (16)	0.104 (3)	0.0056 (14)	−0.0359 (19)	−0.0063 (17)
O2	0.0595 (17)	0.0386 (14)	0.0658 (17)	0.0080 (12)	−0.0166 (15)	−0.0028 (14)
N1	0.0416 (17)	0.0335 (16)	0.071 (2)	0.0021 (14)	0.0019 (18)	0.0024 (15)
C1	0.063 (3)	0.0317 (19)	0.097 (3)	−0.0042 (16)	−0.001 (3)	0.003 (2)
C2	0.047 (2)	0.041 (2)	0.082 (3)	−0.0048 (17)	−0.002 (2)	0.000 (2)
C3	0.049 (2)	0.0322 (18)	0.063 (2)	0.0022 (16)	0.002 (2)	−0.0028 (17)
C4	0.049 (2)	0.0345 (19)	0.065 (3)	0.0002 (17)	0.003 (2)	−0.0024 (18)
C5	0.042 (2)	0.0373 (19)	0.057 (2)	−0.0015 (16)	0.002 (2)	−0.0033 (18)
C6	0.042 (2)	0.0364 (19)	0.064 (2)	−0.0017 (16)	−0.008 (2)	−0.0015 (17)
C7	0.051 (2)	0.0365 (18)	0.059 (2)	−0.0007 (16)	−0.010 (2)	−0.0041 (19)
C8	0.047 (2)	0.039 (2)	0.053 (2)	0.0063 (16)	−0.0047 (19)	0.0005 (17)
C9	0.058 (3)	0.045 (2)	0.065 (3)	−0.0010 (18)	−0.017 (2)	−0.003 (2)
C10	0.060 (3)	0.039 (2)	0.069 (3)	−0.0035 (18)	−0.011 (2)	−0.006 (2)
C11	0.059 (3)	0.041 (2)	0.064 (3)	0.0043 (19)	−0.013 (2)	−0.0047 (19)
C12	0.043 (2)	0.0378 (19)	0.054 (2)	0.0001 (16)	−0.0069 (18)	−0.0056 (18)
C13	0.054 (3)	0.049 (2)	0.060 (3)	0.0042 (18)	−0.004 (2)	−0.001 (2)
C14	0.082 (3)	0.051 (3)	0.070 (3)	0.013 (2)	−0.021 (3)	0.005 (2)
C15	0.060 (3)	0.055 (3)	0.095 (4)	0.020 (2)	−0.023 (3)	−0.028 (3)
C16	0.053 (3)	0.075 (3)	0.081 (3)	0.006 (2)	0.001 (3)	−0.021 (3)
C17	0.062 (3)	0.057 (3)	0.066 (3)	−0.005 (2)	−0.002 (2)	−0.001 (2)

Geometric parameters (Å, º)

O1—C6	1.341 (5)	C12—C13	1.378 (6)
O2—C8	1.370 (5)	C13—C14	1.387 (6)
O2—C11	1.438 (5)	C14—C15	1.371 (8)
N1—C3	1.414 (5)	C15—C16	1.374 (8)
N1—C4	1.278 (6)	C16—C17	1.381 (7)
O1—H1O	0.8200	C1—H1	0.9300
C1—C1^i	1.380 (6)	C2—H2	0.9300
C1—C2	1.373 (6)	C4—H4	1.05 (4)
C2—C3	1.395 (5)	C7—H7	0.9300
C3—C3^i	1.399 (5)	C9—H9	0.9300
C4—C5	1.454 (5)	C10—H10	0.9300
C5—C10	1.400 (6)	C11—H11A	0.9700
C5—C6	1.394 (5)	C11—H11B	0.9700
C6—C7	1.403 (5)	C13—H13	0.9300
C7—C8	1.383 (6)	C14—H14	0.9300
C8—C9	1.388 (6)	C15—H15	0.9300
C9—C10	1.371 (6)	C16—H16	0.9300
C11—C12	1.499 (6)	C17—H17	0.9300
C12—C17	1.383 (6)
C8—O2—C11	117.4 (3)	C12—C17—C16	120.5 (5)
C3—N1—C4	118.9 (4)	C2—C1—H1	120.00
C6—O1—H1O	109.00	C1^i—C1—H1	120.00
C1^i—C1—C2	119.8 (4)	C1—C2—H2	119.00
C1—C2—C3	121.3 (4)	C3—C2—H2	119.00
N1—C3—C3^i	118.3 (3)	N1—C4—H4	122 (2)
C2—C3—C3^i	118.9 (4)	C5—C4—H4	116 (2)
N1—C3—C2	122.8 (4)	C6—C7—H7	120.00
N1—C4—C5	122.2 (4)	C8—C7—H7	120.00
C4—C5—C10	120.5 (4)	C8—C9—H9	120.00
C6—C5—C10	117.7 (3)	C10—C9—H9	120.00
C4—C5—C6	121.8 (4)	C5—C10—H10	119.00
O1—C6—C7	117.5 (3)	C9—C10—H10	119.00
C5—C6—C7	120.7 (4)	O2—C11—H11A	110.00
O1—C6—C5	121.8 (3)	O2—C11—H11B	110.00
C6—C7—C8	119.6 (4)	C12—C11—H11A	110.00
O2—C8—C9	115.0 (4)	C12—C11—H11B	110.00
C7—C8—C9	120.5 (4)	H11A—C11—H11B	108.00
O2—C8—C7	124.5 (3)	C12—C13—H13	120.00
C8—C9—C10	119.2 (4)	C14—C13—H13	120.00
C5—C10—C9	122.3 (4)	C13—C14—H14	120.00
O2—C11—C12	108.6 (3)	C15—C14—H14	120.00
C11—C12—C13	120.9 (4)	C14—C15—H15	120.00
C13—C12—C17	118.8 (4)	C16—C15—H15	120.00
C11—C12—C17	120.3 (4)	C15—C16—H16	120.00
C12—C13—C14	120.8 (4)	C17—C16—H16	120.00
C13—C14—C15	119.8 (4)	C12—C17—H17	120.00
C14—C15—C16	120.0 (5)	C16—C17—H17	120.00
C15—C16—C17	120.2 (5)
C11—O2—C8—C7	1.5 (6)	C4—C5—C10—C9	179.6 (4)
C11—O2—C8—C9	−177.8 (4)	C6—C5—C10—C9	0.9 (6)
C8—O2—C11—C12	174.0 (3)	O1—C6—C7—C8	177.9 (4)
C4—N1—C3—C2	41.3 (6)	C5—C6—C7—C8	−1.4 (6)
C4—N1—C3—C3^i	−139.8 (4)	C6—C7—C8—O2	−178.4 (4)
C3—N1—C4—C5	−176.8 (4)	C6—C7—C8—C9	0.9 (6)
C1^i—C1—C2—C3	0.1 (8)	O2—C8—C9—C10	179.9 (4)
C2—C1—C1^i—C2^i	0.0 (9)	C7—C8—C9—C10	0.5 (7)
C1—C2—C3—N1	178.9 (5)	C8—C9—C10—C5	−1.4 (7)
C1—C2—C3—C3^i	−0.1 (7)	O2—C11—C12—C13	96.8 (4)
N1—C3—C3^i—N1^i	0.0 (6)	O2—C11—C12—C17	−84.8 (5)
N1—C3—C3^i—C2^i	−179.0 (4)	C11—C12—C13—C14	176.4 (4)
C2—C3—C3^i—N1^i	179.0 (4)	C17—C12—C13—C14	−2.0 (6)
C2—C3—C3^i—C2^i	0.0 (6)	C11—C12—C17—C16	−177.4 (4)
N1—C4—C5—C6	−0.9 (7)	C13—C12—C17—C16	1.0 (7)
N1—C4—C5—C10	−179.5 (4)	C12—C13—C14—C15	1.4 (7)
C4—C5—C6—O1	2.6 (6)	C13—C14—C15—C16	0.2 (7)
C4—C5—C6—C7	−178.2 (4)	C14—C15—C16—C17	−1.2 (8)
C10—C5—C6—O1	−178.8 (4)	C15—C16—C17—C12	0.6 (8)
C10—C5—C6—C7	0.5 (6)

Symmetry code: (i) −x, y, z.

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C5–C10 phenol ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.82	1.90	2.622 (5)	147
C2—H2···Cg2^ii	0.93	2.88	3.499 (5)	125
C13—H13···Cg2^iii	0.93	2.60	3.493 (5)	161

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