Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The structure of the title compound, C19H18N2O, was studied in the course of our investigations on organic non-linear optical (NLO) materials. Its mol­ecule with the exception of the C(CH3)2 group is nearly planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008480/ya6027sup1.cif
Contains datablocks I, ccd1444

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008480/ya6027Isup2.hkl
Contains datablock I

CCDC reference: 170318

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.095
  • Data-to-parameter ratio = 9.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
ABSMU_01 Alert B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.074 Value of mu given = 0.070
Yellow Alert Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(15) - C(16) = 1.43 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(15) - C(17) = 1.43 Ang. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.40 From the CIF: _reflns_number_total 1921 Count of symmetry unique reflns 1962 Completeness (_total/calc) 97.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995).

(I) top
Crystal data top
C19H18N2ODx = 1.187 Mg m3
Mr = 290.35Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 10060 reflections
a = 15.4413 (3) Åθ = 3.1–27.4°
b = 10.9988 (3) ŵ = 0.07 mm1
c = 9.5699 (2) ÅT = 291 K
V = 1625.31 (6) Å3Block, red
Z = 40.25 × 0.23 × 0.23 mm
F(000) = 616
Data collection top
Nonius KappaCCD
diffractometer
1302 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 27.4°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 1919
201 frames via ω–rotation (Δω=1%) and two times 20 s per frame (two sets at different κ–angles) scansk = 1414
1921 measured reflectionsl = 1212
1921 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0555P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
1921 reflectionsΔρmax = 0.12 e Å3
203 parametersΔρmin = 0.11 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (3)
Special details top

Experimental. The data collection covered the whole sphere of reciprocal space. The crystal-to-detector distance was 34 mm. Crystal decay was monitored by repeating the initial frames at the end of data collection and analysing the duplicate reflections.

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 (Å2) top
xyzUiso*/Ueq
O10.54750 (10)0.15514 (18)0.5395 (2)0.0749 (6)
H10.57830.18700.59890.112*
N10.83970 (17)0.2503 (2)0.7355 (3)0.0753 (7)
N20.58520 (17)0.2233 (2)0.5335 (3)0.0827 (7)
C10.69221 (13)0.04293 (19)0.1955 (2)0.0426 (5)
C20.73123 (13)0.09715 (19)0.3099 (2)0.0468 (6)
H20.79090.10820.30890.056*
C30.68509 (14)0.1355 (2)0.4254 (2)0.0478 (5)
H30.71340.17250.49990.057*
C40.59748 (13)0.1186 (2)0.4293 (2)0.0509 (6)
C50.55606 (15)0.0642 (3)0.3172 (3)0.0652 (7)
H50.49640.05280.31980.078*
C60.60214 (14)0.0271 (2)0.2025 (3)0.0592 (7)
H60.57330.00920.12820.071*
C70.74379 (14)0.00947 (19)0.0751 (2)0.0444 (5)
H70.80340.01620.08620.053*
C80.71726 (14)0.0297 (2)0.0493 (2)0.0465 (6)
H80.65790.03910.06170.056*
C90.77203 (13)0.05884 (18)0.1669 (2)0.0416 (5)
C100.73713 (13)0.10251 (19)0.2865 (2)0.0454 (5)
H100.67720.10860.29220.054*
C110.78721 (13)0.13980 (19)0.4043 (2)0.0428 (5)
C120.88379 (13)0.1336 (2)0.3922 (3)0.0552 (6)
H12A0.90820.12080.48450.066*
H12B0.90510.21100.35790.066*
C130.91548 (13)0.0324 (2)0.2950 (2)0.0504 (6)
C140.86870 (13)0.0443 (2)0.1551 (2)0.0453 (5)
H14A0.89200.11410.10570.054*
H14B0.88090.02730.09940.054*
C150.74921 (14)0.18608 (19)0.5220 (2)0.0479 (6)
C160.79921 (16)0.2226 (2)0.6404 (3)0.0542 (6)
C170.65798 (18)0.2053 (2)0.5306 (3)0.0544 (6)
C181.01269 (15)0.0488 (3)0.2716 (3)0.0791 (9)
H18A1.04230.04480.35970.119*
H18B1.02320.12630.22890.119*
H18C1.03360.01460.21150.119*
C190.89807 (17)0.0923 (2)0.3597 (3)0.0710 (7)
H19A0.83670.10440.36850.107*
H19B0.92450.09640.45040.107*
H19C0.92210.15450.30080.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0675 (10)0.1041 (14)0.0531 (11)0.0104 (10)0.0201 (9)0.0254 (10)
N10.0944 (17)0.0894 (15)0.0420 (13)0.0080 (12)0.0055 (13)0.0218 (12)
N20.0766 (16)0.0971 (18)0.0743 (17)0.0156 (13)0.0113 (15)0.0127 (14)
C10.0457 (12)0.0476 (12)0.0343 (13)0.0012 (9)0.0037 (10)0.0037 (10)
C20.0425 (11)0.0571 (13)0.0407 (14)0.0006 (10)0.0011 (11)0.0034 (11)
C30.0547 (13)0.0551 (13)0.0337 (12)0.0009 (10)0.0031 (11)0.0097 (11)
C40.0536 (15)0.0588 (14)0.0402 (14)0.0019 (10)0.0149 (12)0.0075 (11)
C50.0458 (13)0.0960 (19)0.0539 (17)0.0160 (12)0.0098 (14)0.0177 (15)
C60.0514 (13)0.0843 (17)0.0419 (15)0.0173 (11)0.0042 (12)0.0168 (14)
C70.0444 (11)0.0528 (13)0.0361 (13)0.0003 (9)0.0016 (10)0.0007 (10)
C80.0449 (11)0.0583 (14)0.0364 (14)0.0036 (10)0.0034 (11)0.0079 (10)
C90.0466 (11)0.0451 (11)0.0330 (12)0.0015 (9)0.0014 (11)0.0031 (10)
C100.0464 (11)0.0528 (13)0.0369 (12)0.0026 (9)0.0021 (11)0.0064 (11)
C110.0542 (12)0.0414 (11)0.0327 (12)0.0024 (9)0.0015 (11)0.0023 (10)
C120.0542 (12)0.0713 (16)0.0400 (14)0.0005 (11)0.0060 (11)0.0138 (12)
C130.0467 (12)0.0679 (15)0.0367 (13)0.0072 (10)0.0045 (11)0.0110 (12)
C140.0475 (12)0.0532 (13)0.0352 (13)0.0001 (9)0.0007 (10)0.0055 (11)
C150.0625 (14)0.0471 (13)0.0341 (13)0.0061 (10)0.0010 (12)0.0055 (11)
C160.0719 (16)0.0554 (14)0.0354 (14)0.0072 (11)0.0041 (13)0.0092 (12)
C170.0690 (18)0.0550 (14)0.0392 (14)0.0085 (11)0.0074 (13)0.0059 (11)
C180.0472 (13)0.135 (3)0.0550 (18)0.0085 (15)0.0070 (14)0.0223 (18)
C190.0890 (17)0.0771 (17)0.0470 (16)0.0217 (13)0.0105 (14)0.0007 (15)
Geometric parameters (Å, º) top
O1—C41.368 (3)C10—C111.427 (3)
O1—H10.820C10—H100.930
N1—C161.145 (3)C11—C151.368 (3)
N2—C171.141 (3)C11—C121.497 (3)
C1—C21.385 (3)C12—C131.531 (3)
C1—C61.403 (3)C12—H12A0.970
C1—C71.448 (3)C12—H12B0.970
C2—C31.381 (3)C13—C141.527 (3)
C2—H20.930C13—C181.528 (3)
C3—C41.366 (3)C13—C191.529 (4)
C3—H30.930C14—H14A0.970
C4—C51.385 (3)C14—H14B0.970
C5—C61.370 (3)C15—C171.427 (4)
C5—H50.930C15—C161.429 (4)
C6—H60.930C18—H18A0.960
C7—C81.330 (3)C18—H18B0.960
C7—H70.930C18—H18C0.960
C8—C91.444 (3)C19—H19A0.960
C8—H80.930C19—H19B0.960
C9—C101.353 (3)C19—H19C0.960
C9—C141.505 (3)
C4—O1—H1109.5C11—C12—H12A108.9
C2—C1—C6116.51 (19)C13—C12—H12A108.9
C2—C1—C7119.96 (17)C11—C12—H12B108.9
C6—C1—C7123.50 (19)C13—C12—H12B108.9
C3—C2—C1122.69 (18)H12A—C12—H12B107.7
C3—C2—H2118.7C14—C13—C18109.04 (19)
C1—C2—H2118.7C14—C13—C19110.42 (19)
C4—C3—C2119.4 (2)C18—C13—C19109.7 (2)
C4—C3—H3120.3C14—C13—C12108.62 (18)
C2—C3—H3120.3C18—C13—C12108.51 (18)
C3—C4—O1122.7 (2)C19—C13—C12110.5 (2)
C3—C4—C5119.7 (2)C9—C14—C13114.35 (19)
O1—C4—C5117.64 (18)C9—C14—H14A108.7
C6—C5—C4120.6 (2)C13—C14—H14A108.7
C6—C5—H5119.7C9—C14—H14B108.7
C4—C5—H5119.7C13—C14—H14B108.7
C5—C6—C1121.1 (2)H14A—C14—H14B107.6
C5—C6—H6119.5C11—C15—C17121.8 (2)
C1—C6—H6119.5C11—C15—C16121.73 (19)
C8—C7—C1128.66 (18)C17—C15—C16116.4 (2)
C8—C7—H7115.7N1—C16—C15179.0 (3)
C1—C7—H7115.7N2—C17—C15177.6 (3)
C7—C8—C9126.08 (19)C13—C18—H18A109.5
C7—C8—H8117.0C13—C18—H18B109.5
C9—C8—H8117.0H18A—C18—H18B109.5
C10—C9—C8120.31 (17)C13—C18—H18C109.5
C10—C9—C14119.74 (19)H18A—C18—H18C109.5
C8—C9—C14119.91 (19)H18B—C18—H18C109.5
C9—C10—C11123.66 (18)C13—C19—H19A109.5
C9—C10—H10118.2C13—C19—H19B109.5
C11—C10—H10118.2H19A—C19—H19B109.5
C15—C11—C10121.65 (17)C13—C19—H19C109.5
C15—C11—C12120.49 (19)H19A—C19—H19C109.5
C10—C11—C12117.76 (18)H19B—C19—H19C109.5
C11—C12—C13113.46 (18)
C6—C1—C2—C30.7 (3)C9—C10—C11—C15178.5 (2)
C7—C1—C2—C3177.37 (19)C9—C10—C11—C122.0 (3)
C1—C2—C3—C40.8 (3)C15—C11—C12—C13153.2 (2)
C2—C3—C4—O1179.4 (2)C10—C11—C12—C1330.2 (3)
C2—C3—C4—C50.5 (3)C11—C12—C13—C1452.0 (3)
C3—C4—C5—C60.1 (4)C11—C12—C13—C18170.4 (2)
O1—C4—C5—C6179.0 (2)C11—C12—C13—C1969.2 (3)
C4—C5—C6—C10.0 (4)C10—C9—C14—C1323.2 (3)
C2—C1—C6—C50.2 (3)C8—C9—C14—C13158.7 (2)
C7—C1—C6—C5177.7 (2)C18—C13—C14—C9166.7 (2)
C2—C1—C7—C8171.4 (2)C19—C13—C14—C972.7 (2)
C6—C1—C7—C86.5 (4)C12—C13—C14—C948.6 (3)
C1—C7—C8—C9178.3 (2)C10—C11—C15—C173.2 (3)
C7—C8—C9—C10177.4 (2)C12—C11—C15—C17173.1 (2)
C7—C8—C9—C140.7 (3)C10—C11—C15—C16179.5 (2)
C8—C9—C10—C11176.37 (19)C12—C11—C15—C164.1 (3)
C14—C9—C10—C111.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.822.142.958 (3)173
Symmetry code: (i) x+3/2, y+1/2, z+3/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds