2,2′-[1,1′-(Propane-1,3-di­yl)bis­(nitrilo­ethyl­idyne)]diphenol

The structure of the title compound, C₁₉H₂₂N₂O₂, shows two intra­molecular O—H...N hydrogen-bonding inter­actions. The packing is stabilized through van der Waals contacts and two C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.193
• Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.857     0.984
            Tmin(prime) and Tmax expected:      0.976     0.984
            RR(prime) =      0.878
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C13
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        \P1
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        \P2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

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

   5 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993\bbr00q) in WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

2,2'-[1,1'-(Propane-1,3-diyl)bis(nitriloethylidyne)diphenol

Crystal data

C19H22N2O2	F(000) = 664
Mr = 310.39	Dx = 1.224 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7073 reflections
a = 12.4524 (4) Å	θ = 2.1–28°
b = 15.3347 (5) Å	µ = 0.08 mm^−1
c = 8.8832 (2) Å	T = 293 K
β = 96.991 (2)°	Plate, colourless
V = 1683.67 (9) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa-APEX2 diffractometer	4335 independent reflections
Radiation source: fine-focus sealed tube	2848 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω and φ scans	θmax = 28.7°, θmin = 1.7°
Absorption correction: multi-scan (Blessing, 1995)	h = −16→16
Tmin = 0.857, Tmax = 0.984	k = −20→20
20405 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1092P)^2 + 0.2308P] where P = (Fo^2 + 2Fc^2)/3
4335 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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.

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 > σ(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	0.08793 (16)	0.85107 (12)	1.1554 (2)	0.0605 (4)
C2	0.0515 (2)	0.83451 (15)	1.2956 (2)	0.0795 (6)
H2	0.1000	0.8150	1.3765	0.095*
C3	−0.0559 (2)	0.84689 (15)	1.3148 (2)	0.0818 (7)
H3	−0.0790	0.8359	1.4087	0.098*
C4	−0.12882 (18)	0.87509 (14)	1.1971 (2)	0.0726 (6)
H4	−0.2008	0.8840	1.2113	0.087*
C5	−0.09523 (15)	0.89015 (12)	1.0578 (2)	0.0612 (5)
H5	−0.1455	0.9089	0.9783	0.073*
C6	0.01260 (13)	0.87813 (10)	1.03197 (18)	0.0497 (4)
C7	0.04743 (13)	0.89107 (10)	0.88117 (18)	0.0485 (4)
C8	−0.03427 (15)	0.91290 (15)	0.7489 (2)	0.0659 (5)
H8A	0.0014	0.9193	0.6596	0.099*
H8B	−0.0698	0.9665	0.7685	0.099*
H8C	−0.0868	0.8669	0.7336	0.099*
C9	0.19118 (14)	0.88534 (13)	0.7236 (2)	0.0592 (4)
H9A	0.1767	0.9425	0.6790	0.071*
H9B	0.1558	0.8422	0.6548	0.071*
C10	0.31163 (14)	0.86895 (13)	0.7459 (2)	0.0619 (5)
H10A	0.3471	0.9175	0.8016	0.074*
H10B	0.3260	0.8169	0.8071	0.074*
C11	0.35990 (15)	0.85764 (12)	0.5993 (2)	0.0627 (5)
H11A	0.4358	0.8424	0.6214	0.075*
H11B	0.3233	0.8104	0.5412	0.075*
C12	0.38548 (12)	0.94528 (10)	0.38155 (18)	0.0489 (4)
C13	0.44276 (15)	0.87288 (13)	0.3096 (2)	0.0670 (5)
H13A	0.4458	0.8222	0.3735	0.101*
H13B	0.5149	0.8911	0.2971	0.101*
H13C	0.4041	0.8591	0.2124	0.101*
C14	0.37098 (11)	1.03009 (10)	0.30374 (17)	0.0473 (4)
C15	0.40440 (14)	1.04511 (13)	0.1617 (2)	0.0634 (5)
H15	0.4353	0.9996	0.1127	0.076*
C16	0.39290 (16)	1.12563 (16)	0.0914 (2)	0.0726 (6)
H16	0.4167	1.1341	−0.0027	0.087*
C17	0.34599 (15)	1.19306 (14)	0.1621 (2)	0.0667 (5)
H17	0.3382	1.2474	0.1154	0.080*
C18	0.31083 (14)	1.18080 (11)	0.3001 (2)	0.0578 (4)
H18	0.2789	1.2269	0.3461	0.069*
C19	0.32189 (12)	1.10045 (10)	0.37325 (17)	0.0474 (4)
N1	0.14839 (11)	0.88058 (9)	0.86902 (16)	0.0534 (3)
N2	0.34936 (11)	0.93775 (9)	0.51000 (16)	0.0525 (3)
O1	0.19250 (11)	0.83961 (11)	1.14088 (16)	0.0791 (4)
H1	0.2032	0.8515	1.0539	0.119*
O2	0.28584 (11)	1.09222 (8)	0.50796 (13)	0.0617 (3)
H2A	0.2646	1.0422	0.5179	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0714 (12)	0.0527 (9)	0.0571 (10)	−0.0003 (8)	0.0070 (8)	0.0004 (8)
C2	0.1118 (19)	0.0734 (13)	0.0532 (10)	0.0004 (12)	0.0095 (10)	0.0059 (9)
C3	0.1148 (19)	0.0740 (13)	0.0629 (12)	−0.0154 (12)	0.0366 (12)	−0.0073 (10)
C4	0.0762 (13)	0.0724 (13)	0.0742 (13)	−0.0181 (10)	0.0296 (10)	−0.0161 (10)
C5	0.0591 (10)	0.0628 (11)	0.0636 (10)	−0.0124 (8)	0.0144 (8)	−0.0103 (8)
C6	0.0518 (9)	0.0446 (8)	0.0530 (9)	−0.0085 (6)	0.0080 (6)	−0.0047 (6)
C7	0.0486 (9)	0.0458 (8)	0.0511 (8)	−0.0065 (6)	0.0056 (6)	−0.0015 (6)
C8	0.0536 (10)	0.0860 (14)	0.0573 (10)	−0.0021 (9)	0.0029 (7)	0.0004 (9)
C9	0.0520 (10)	0.0679 (11)	0.0592 (10)	−0.0012 (8)	0.0128 (7)	0.0073 (8)
C10	0.0521 (10)	0.0642 (11)	0.0712 (11)	0.0031 (8)	0.0143 (8)	0.0190 (8)
C11	0.0552 (10)	0.0523 (9)	0.0840 (12)	0.0074 (8)	0.0223 (8)	0.0129 (9)
C12	0.0355 (7)	0.0509 (9)	0.0613 (9)	−0.0018 (6)	0.0106 (6)	−0.0060 (7)
C13	0.0607 (11)	0.0606 (11)	0.0839 (13)	0.0060 (8)	0.0255 (9)	−0.0096 (9)
C14	0.0376 (7)	0.0544 (9)	0.0508 (8)	−0.0029 (6)	0.0089 (6)	−0.0018 (7)
C15	0.0571 (10)	0.0784 (12)	0.0577 (10)	0.0025 (9)	0.0197 (8)	−0.0008 (9)
C16	0.0691 (12)	0.0958 (16)	0.0550 (10)	−0.0065 (11)	0.0158 (8)	0.0152 (10)
C17	0.0648 (11)	0.0698 (12)	0.0627 (10)	−0.0108 (9)	−0.0035 (8)	0.0180 (9)
C18	0.0617 (10)	0.0510 (9)	0.0587 (9)	−0.0004 (8)	−0.0007 (7)	0.0009 (7)
C19	0.0443 (8)	0.0499 (9)	0.0479 (8)	−0.0029 (6)	0.0053 (6)	−0.0016 (6)
N1	0.0490 (8)	0.0559 (8)	0.0558 (8)	−0.0024 (6)	0.0088 (6)	0.0040 (6)
N2	0.0480 (7)	0.0483 (7)	0.0635 (8)	0.0012 (6)	0.0165 (6)	0.0053 (6)
O1	0.0682 (9)	0.0974 (11)	0.0696 (9)	0.0154 (7)	−0.0005 (6)	0.0132 (7)
O2	0.0784 (9)	0.0535 (7)	0.0577 (7)	0.0064 (6)	0.0259 (6)	−0.0008 (5)

Geometric parameters (Å, º)

C1—O1	1.336 (2)	C10—H10B	0.9700
C1—C2	1.400 (3)	C11—N2	1.460 (2)
C1—C6	1.415 (2)	C11—H11A	0.9700
C2—C3	1.382 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—N2	1.2817 (19)
C3—C4	1.369 (3)	C12—C14	1.473 (2)
C3—H3	0.9300	C12—C13	1.504 (2)
C4—C5	1.373 (3)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.402 (2)	C13—H13C	0.9600
C5—H5	0.9300	C14—C15	1.395 (2)
C6—C7	1.471 (2)	C14—C19	1.418 (2)
C7—N1	1.285 (2)	C15—C16	1.383 (3)
C7—C8	1.496 (2)	C15—H15	0.9300
C8—H8A	0.9600	C16—C17	1.376 (3)
C8—H8B	0.9600	C16—H16	0.9300
C8—H8C	0.9600	C17—C18	1.364 (3)
C9—N1	1.458 (2)	C17—H17	0.9300
C9—C10	1.510 (2)	C18—C19	1.392 (2)
C9—H9A	0.9700	C18—H18	0.9300
C9—H9B	0.9700	C19—O2	1.3343 (18)
C10—C11	1.509 (3)	O1—H1	0.8200
C10—H10A	0.9700	O2—H2A	0.8200
O1—C1—C2	119.14 (18)	H10A—C10—H10B	107.7
O1—C1—C6	121.74 (16)	N2—C11—C10	110.69 (14)
C2—C1—C6	119.12 (19)	N2—C11—H11A	109.5
C3—C2—C1	120.5 (2)	C10—C11—H11A	109.5
C3—C2—H2	119.7	N2—C11—H11B	109.5
C1—C2—H2	119.7	C10—C11—H11B	109.5
C4—C3—C2	120.74 (19)	H11A—C11—H11B	108.1
C4—C3—H3	119.6	N2—C12—C14	117.45 (13)
C2—C3—H3	119.6	N2—C12—C13	123.21 (16)
C3—C4—C5	119.7 (2)	C14—C12—C13	119.33 (14)
C3—C4—H4	120.2	C12—C13—H13A	109.5
C5—C4—H4	120.2	C12—C13—H13B	109.5
C4—C5—C6	121.90 (19)	H13A—C13—H13B	109.5
C4—C5—H5	119.1	C12—C13—H13C	109.5
C6—C5—H5	119.1	H13A—C13—H13C	109.5
C5—C6—C1	118.01 (16)	H13B—C13—H13C	109.5
C5—C6—C7	121.73 (15)	C15—C14—C19	117.39 (15)
C1—C6—C7	120.25 (15)	C15—C14—C12	122.48 (14)
N1—C7—C6	117.36 (14)	C19—C14—C12	120.14 (13)
N1—C7—C8	122.74 (15)	C16—C15—C14	121.97 (17)
C6—C7—C8	119.87 (15)	C16—C15—H15	119.0
C7—C8—H8A	109.5	C14—C15—H15	119.0
C7—C8—H8B	109.5	C17—C16—C15	119.45 (17)
H8A—C8—H8B	109.5	C17—C16—H16	120.3
C7—C8—H8C	109.5	C15—C16—H16	120.3
H8A—C8—H8C	109.5	C18—C17—C16	120.45 (18)
H8B—C8—H8C	109.5	C18—C17—H17	119.8
N1—C9—C10	109.86 (15)	C16—C17—H17	119.8
N1—C9—H9A	109.7	C17—C18—C19	121.15 (17)
C10—C9—H9A	109.7	C17—C18—H18	119.4
N1—C9—H9B	109.7	C19—C18—H18	119.4
C10—C9—H9B	109.7	O2—C19—C18	118.52 (14)
H9A—C9—H9B	108.2	O2—C19—C14	121.90 (14)
C11—C10—C9	113.56 (16)	C18—C19—C14	119.58 (15)
C11—C10—H10A	108.9	C7—N1—C9	122.34 (14)
C9—C10—H10A	108.9	C12—N2—C11	122.80 (14)
C11—C10—H10B	108.9	C1—O1—H1	109.5
C9—C10—H10B	108.9	C19—O2—H2A	109.5
O1—C1—C2—C3	179.1 (2)	N2—C12—C14—C19	2.0 (2)
C6—C1—C2—C3	−1.9 (3)	C13—C12—C14—C19	−176.92 (15)
C1—C2—C3—C4	0.3 (3)	C19—C14—C15—C16	1.4 (3)
C2—C3—C4—C5	0.9 (3)	C12—C14—C15—C16	−178.30 (17)
C3—C4—C5—C6	−0.5 (3)	C14—C15—C16—C17	−0.8 (3)
C4—C5—C6—C1	−1.1 (3)	C15—C16—C17—C18	−0.1 (3)
C4—C5—C6—C7	177.60 (16)	C16—C17—C18—C19	0.4 (3)
O1—C1—C6—C5	−178.82 (17)	C17—C18—C19—O2	−179.88 (15)
C2—C1—C6—C5	2.2 (3)	C17—C18—C19—C14	0.3 (2)
O1—C1—C6—C7	2.5 (3)	C15—C14—C19—O2	179.02 (15)
C2—C1—C6—C7	−176.45 (16)	C12—C14—C19—O2	−1.2 (2)
C5—C6—C7—N1	178.38 (15)	C15—C14—C19—C18	−1.2 (2)
C1—C6—C7—N1	−3.0 (2)	C12—C14—C19—C18	178.58 (14)
C5—C6—C7—C8	−3.4 (2)	C6—C7—N1—C9	175.41 (14)
C1—C6—C7—C8	175.25 (16)	C8—C7—N1—C9	−2.8 (3)
N1—C9—C10—C11	170.33 (15)	C10—C9—N1—C7	−179.11 (16)
C9—C10—C11—N2	64.1 (2)	C14—C12—N2—C11	−179.17 (15)
N2—C12—C14—C15	−178.23 (15)	C13—C12—N2—C11	−0.3 (3)
C13—C12—C14—C15	2.8 (2)	C10—C11—N2—C12	178.99 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.76	2.4912 (19)	148
O2—H2A···N2	0.82	1.92	2.4967 (17)	126
C8—H8B···Π1^i	0.96	2.88	3.558	129
C11—H11A···Π2^ii	0.97	2.82	3.678	148

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