Crystal structure of (Z)-N-benzyl­idene-1-phenyl­methanamine oxide hydrogen peroxide monosolvate

The title structure consists of a (Z)-N-benzyl­idene-1-phenyl­methanamine oxide and a hydrogen peroxide mol­ecule linked through both O—H groups into a one-dimensional chain structure.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.077
• wR factor = 0.218
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.007 Ang.
PLAT355_ALERT_3_C Long    O-H (X0.82,N0.98A)  O1     -   H1     ..       1.05 Ang.
PLAT355_ALERT_3_C Long    O-H (X0.82,N0.98A)  O2     -   H2     ..       1.06 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      6.673 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.596         25 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2016 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 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

   2 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
   7 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

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Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(Z)-N-Benzylidene-1-phenylmethanamine oxide hydrogen peroxide monosolvate

Crystal data

C14H13NO·H2O2	F(000) = 520
Mr = 245.27	Dx = 1.287 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 737 reflections
a = 21.802 (15) Å	θ = 3.2–21.9°
b = 4.597 (3) Å	µ = 0.09 mm^−1
c = 12.742 (9) Å	T = 150 K
β = 97.598 (11)°	Needle, colourless
V = 1265.8 (16) Å^3	0.40 × 0.04 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEXII area-detector diffractometer	2227 independent reflections
Radiation source: fine-focus sealed tube	1113 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.108
ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −25→25
Tmin = 0.965, Tmax = 0.996	k = −5→5
7458 measured reflections	l = −15→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.077	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.218	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2227 reflections	Δρmax = 0.27 e Å^−3
172 parameters	Δρmin = −0.26 e Å^−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (6)

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.

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 > 2sigma(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
O1	0.23321 (15)	0.7522 (7)	1.0077 (3)	0.0427 (9)
O2	0.28942 (16)	0.9116 (7)	0.9911 (3)	0.0442 (10)
O3	0.22608 (15)	0.3093 (6)	0.8666 (2)	0.0377 (9)
N1	0.23366 (18)	0.3713 (7)	0.7676 (3)	0.0319 (10)
C11	0.2883 (2)	0.5529 (9)	0.7569 (4)	0.0342 (12)
H112	0.2894	0.7210	0.8057	0.041*
H111	0.2855	0.6284	0.6836	0.041*
C12	0.3463 (2)	0.3775 (9)	0.7821 (4)	0.0344 (12)
C13	0.3802 (2)	0.3866 (10)	0.8826 (4)	0.0438 (13)
H13	0.3672	0.5083	0.9356	0.053*
C14	0.4332 (2)	0.2183 (12)	0.9054 (5)	0.0573 (16)
H14	0.4563	0.2229	0.9741	0.069*
C15	0.4521 (3)	0.0431 (12)	0.8270 (5)	0.0592 (17)
H15	0.4888	−0.0694	0.8422	0.071*
C16	0.4190 (2)	0.0295 (12)	0.7281 (5)	0.0521 (15)
H16	0.4317	−0.0952	0.6756	0.063*
C17	0.3671 (2)	0.1997 (10)	0.7062 (4)	0.0423 (13)
H17	0.3447	0.1954	0.6370	0.051*
C21	0.1988 (2)	0.2713 (9)	0.6851 (4)	0.0334 (11)
H21	0.2083	0.3366	0.6184	0.040*
C22	0.1470 (2)	0.0714 (9)	0.6825 (4)	0.0330 (12)
C23	0.1155 (2)	0.0141 (11)	0.5825 (4)	0.0432 (13)
H23	0.1280	0.1064	0.5221	0.052*
C24	0.0658 (2)	−0.1774 (11)	0.5704 (4)	0.0480 (14)
H24	0.0438	−0.2129	0.5022	0.058*
C25	0.0486 (2)	−0.3157 (11)	0.6579 (4)	0.0479 (14)
H25	0.0149	−0.4481	0.6499	0.057*
C26	0.0800 (2)	−0.2629 (11)	0.7565 (4)	0.0443 (14)
H26	0.0681	−0.3606	0.8164	0.053*
C27	0.1284 (2)	−0.0708 (9)	0.7696 (4)	0.0356 (12)
H27	0.1495	−0.0341	0.8384	0.043*
H1	0.232 (2)	0.588 (9)	0.950 (4)	0.060 (15)*
H2	0.268 (2)	1.058 (10)	0.933 (4)	0.057 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.054 (2)	0.0379 (19)	0.038 (2)	−0.0100 (17)	0.0135 (17)	−0.0039 (15)
O2	0.050 (2)	0.0394 (19)	0.044 (2)	−0.0075 (17)	0.0069 (18)	−0.0001 (16)
O3	0.052 (2)	0.0361 (17)	0.026 (2)	−0.0051 (15)	0.0106 (16)	0.0026 (14)
N1	0.041 (2)	0.027 (2)	0.029 (2)	0.0001 (18)	0.012 (2)	−0.0011 (17)
C11	0.041 (3)	0.033 (2)	0.029 (3)	−0.005 (2)	0.008 (2)	−0.001 (2)
C12	0.038 (3)	0.030 (2)	0.036 (3)	−0.007 (2)	0.006 (2)	0.004 (2)
C13	0.043 (3)	0.045 (3)	0.044 (4)	0.000 (3)	0.005 (3)	0.005 (2)
C14	0.047 (3)	0.064 (4)	0.058 (4)	0.003 (3)	−0.002 (3)	0.019 (3)
C15	0.052 (4)	0.048 (3)	0.080 (5)	0.004 (3)	0.020 (4)	0.016 (3)
C16	0.044 (3)	0.054 (3)	0.060 (4)	0.004 (3)	0.014 (3)	0.006 (3)
C17	0.042 (3)	0.043 (3)	0.043 (3)	−0.002 (3)	0.012 (3)	0.004 (2)
C21	0.038 (3)	0.031 (2)	0.031 (3)	0.004 (2)	0.001 (2)	0.001 (2)
C22	0.035 (3)	0.034 (2)	0.030 (3)	0.004 (2)	0.007 (2)	0.000 (2)
C23	0.046 (3)	0.047 (3)	0.035 (3)	0.000 (3)	0.004 (3)	−0.003 (2)
C24	0.039 (3)	0.056 (3)	0.046 (4)	−0.005 (3)	−0.005 (3)	−0.007 (3)
C25	0.042 (3)	0.051 (3)	0.053 (4)	−0.008 (3)	0.016 (3)	−0.013 (3)
C26	0.051 (3)	0.042 (3)	0.043 (3)	−0.002 (3)	0.017 (3)	−0.005 (2)
C27	0.033 (3)	0.038 (3)	0.037 (3)	−0.001 (2)	0.009 (2)	−0.004 (2)

Geometric parameters (Å, º)

O1—O2	1.467 (4)	C16—C17	1.375 (7)
O1—H1	1.05 (4)	C16—H16	0.9500
O2—H2	1.06 (4)	C17—H17	0.9500
O3—N1	1.325 (4)	C21—C22	1.454 (6)
N1—C21	1.297 (6)	C21—H21	0.9500
N1—C11	1.475 (6)	C22—C23	1.390 (6)
C11—C12	1.498 (6)	C22—C27	1.393 (6)
C11—H112	0.9900	C23—C24	1.388 (7)
C11—H111	0.9900	C23—H23	0.9500
C12—C17	1.388 (6)	C24—C25	1.378 (7)
C12—C13	1.392 (7)	C24—H24	0.9500
C13—C14	1.388 (7)	C25—C26	1.371 (7)
C13—H13	0.9500	C25—H25	0.9500
C14—C15	1.389 (8)	C26—C27	1.368 (7)
C14—H14	0.9500	C26—H26	0.9500
C15—C16	1.368 (8)	C27—H27	0.9500
C15—H15	0.9500
O2—O1—H1	102 (3)	C17—C16—H16	120.6
O1—O2—H2	97 (3)	C16—C17—C12	122.0 (5)
C21—N1—O3	124.2 (4)	C16—C17—H17	119.0
C21—N1—C11	121.3 (4)	C12—C17—H17	119.0
O3—N1—C11	114.4 (4)	N1—C21—C22	127.8 (4)
N1—C11—C12	110.1 (3)	N1—C21—H21	116.1
N1—C11—H112	109.6	C22—C21—H21	116.1
C12—C11—H112	109.6	C23—C22—C27	118.8 (4)
N1—C11—H111	109.6	C23—C22—C21	115.4 (4)
C12—C11—H111	109.6	C27—C22—C21	125.8 (5)
H112—C11—H111	108.1	C24—C23—C22	120.3 (5)
C17—C12—C13	118.4 (5)	C24—C23—H23	119.8
C17—C12—C11	120.8 (5)	C22—C23—H23	119.8
C13—C12—C11	120.9 (4)	C25—C24—C23	119.6 (5)
C14—C13—C12	120.2 (5)	C25—C24—H24	120.2
C14—C13—H13	119.9	C23—C24—H24	120.2
C12—C13—H13	119.9	C26—C25—C24	120.2 (5)
C13—C14—C15	119.3 (6)	C26—C25—H25	119.9
C13—C14—H14	120.3	C24—C25—H25	119.9
C15—C14—H14	120.3	C27—C26—C25	120.6 (5)
C16—C15—C14	121.3 (6)	C27—C26—H26	119.7
C16—C15—H15	119.4	C25—C26—H26	119.7
C14—C15—H15	119.4	C26—C27—C22	120.4 (5)
C15—C16—C17	118.8 (5)	C26—C27—H27	119.8
C15—C16—H16	120.6	C22—C27—H27	119.8
C21—N1—C11—C12	−103.9 (5)	C11—N1—C21—C22	174.4 (4)
O3—N1—C11—C12	72.7 (4)	N1—C21—C22—C23	176.4 (4)
N1—C11—C12—C17	82.7 (5)	N1—C21—C22—C27	−6.0 (7)
N1—C11—C12—C13	−96.6 (5)	C27—C22—C23—C24	1.2 (7)
C17—C12—C13—C14	−0.7 (7)	C21—C22—C23—C24	179.0 (4)
C11—C12—C13—C14	178.7 (4)	C22—C23—C24—C25	−1.4 (7)
C12—C13—C14—C15	0.5 (7)	C23—C24—C25—C26	0.5 (7)
C13—C14—C15—C16	−1.1 (8)	C24—C25—C26—C27	0.6 (7)
C14—C15—C16—C17	1.8 (8)	C25—C26—C27—C22	−0.8 (7)
C15—C16—C17—C12	−2.0 (7)	C23—C22—C27—C26	−0.1 (7)
C13—C12—C17—C16	1.4 (7)	C21—C22—C27—C26	−177.6 (4)
C11—C12—C17—C16	−178.0 (4)	H1—O1—O2—H2	88 (4)
O3—N1—C21—C22	−1.8 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	1.05 (5)	1.66 (5)	2.707 (5)	174 (4)
O2—H2···O3^i	1.06 (5)	1.64 (5)	2.681 (5)	166 (4)
C21—H21···O1^ii	0.95	2.46	3.304 (6)	148
C27—H27···O3	0.95	2.29	2.902 (6)	121
C11—H111···O1^ii	0.99	2.44	3.364 (7)	155
C11—H111···O2^ii	0.99	2.47	3.394 (7)	155
C11—H112···O2	0.99	2.52	3.407 (7)	149

Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z−1/2.