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In the title compound, C15H20N2O2, the N atom of the diethyl­amine group has a planar environment, whereas the N atom of the dimethyl­amine group is pyramidal. Inter­molecular C—H...π and C—H...O inter­actions are observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026607/dn6246sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026607/dn6246Isup2.hkl
Contains datablock I

CCDC reference: 283906

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.162
  • Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.138 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.63 Ratio PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O1 .. 2.71 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O2 .. 2.71 Ang. PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CP
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 1823 Count of symmetry unique reflns 1836 Completeness (_total/calc) 99.29% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Crystal Clear (Rigaku, 1999); cell refinement: Crystal Clear; data reduction: Crystal Structure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEPIII for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

7-Diethylamino-3-dimethylamino-2H-1-benzopyran-2-one top
Crystal data top
C15H20N2O2F(000) = 560.00
Mr = 260.34Dx = 1.255 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2abCell parameters from 4379 reflections
a = 6.596 (3) Åθ = 3.1–27.5°
b = 14.360 (6) ŵ = 0.08 mm1
c = 14.549 (6) ÅT = 123 K
V = 1378.0 (10) Å3Prism, orange
Z = 40.15 × 0.14 × 0.10 mm
Data collection top
Rigaku Saturn
diffractometer
1467 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1Rint = 0.138
ω scansθmax = 27.5°
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
h = 88
Tmin = 0.987, Tmax = 0.992k = 1818
11200 measured reflectionsl = 1818
1823 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.057 w = 1/[0.9370σ(Fo2)]/(4Fo2)
wR(F2) = 0.163(Δ/σ)max = 0.0001
S = 1.00Δρmax = 0.31 e Å3
1817 reflectionsΔρmin = 0.31 e Å3
194 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3225 (2)0.81266 (12)0.61901 (13)0.0199 (4)
O20.4480 (3)0.70325 (14)0.70694 (16)0.0285 (5)
N10.0639 (3)0.62869 (14)0.74974 (14)0.0195 (5)
N20.1079 (3)1.05384 (17)0.41548 (17)0.0229 (5)
C10.2947 (4)0.73664 (19)0.67543 (19)0.0197 (6)
C20.0864 (4)0.70677 (18)0.69226 (19)0.0171 (5)
C30.0671 (4)0.74784 (17)0.64592 (18)0.0156 (5)
C40.0313 (4)0.82297 (19)0.58296 (18)0.0160 (5)
C50.1815 (4)0.86916 (18)0.53231 (18)0.0182 (5)
C60.1366 (4)0.94350 (19)0.47660 (19)0.0190 (6)
C70.0650 (4)0.97726 (18)0.46916 (18)0.0181 (6)
C80.2170 (4)0.93009 (18)0.51819 (18)0.0185 (6)
C90.1664 (4)0.85518 (18)0.57280 (18)0.0165 (5)
C100.1576 (5)0.6327 (2)0.8426 (2)0.0295 (7)
C110.1400 (4)0.5923 (2)0.7563 (2)0.0258 (7)
C120.3145 (4)1.0897 (2)0.4088 (2)0.0232 (6)
C130.3738 (5)1.1489 (2)0.4919 (2)0.0304 (7)
C140.0515 (4)1.1073 (2)0.3710 (2)0.0270 (7)
C150.1177 (5)1.0672 (2)0.2778 (2)0.0409 (9)
H10.20200.72670.65530.019*
H20.31800.84860.53670.022*
H30.24180.97250.44250.023*
H40.35430.94970.51370.022*
H50.06270.65770.88510.035*
H60.19550.57180.86150.035*
H70.27440.67130.84060.036*
H80.19670.58740.69640.031*
H90.22050.63310.79240.031*
H100.13690.53250.78420.031*
H110.32491.12680.35500.028*
H120.40531.03850.40440.028*
H130.43241.11010.53760.037*
H140.46951.19460.47340.037*
H150.25691.17870.51620.037*
H160.00331.16900.36190.032*
H170.16621.10860.41040.032*
H180.13301.00150.28230.049*
H190.01791.08130.23280.049*
H200.24331.09430.26040.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0138 (8)0.0187 (8)0.0273 (10)0.0002 (7)0.0025 (8)0.0043 (7)
O20.0146 (9)0.0304 (10)0.0403 (12)0.0006 (9)0.0049 (9)0.0105 (9)
N10.0202 (11)0.0178 (10)0.0206 (10)0.0007 (10)0.0015 (10)0.0050 (9)
N20.0180 (11)0.0204 (11)0.0302 (12)0.0025 (10)0.0021 (10)0.0085 (9)
C10.0195 (13)0.0181 (12)0.0216 (13)0.0007 (11)0.0001 (11)0.0005 (10)
C20.0172 (12)0.0141 (10)0.0201 (12)0.0002 (10)0.0017 (10)0.0036 (10)
C30.0129 (11)0.0153 (11)0.0185 (11)0.0020 (9)0.0031 (10)0.0020 (9)
C40.0144 (11)0.0170 (11)0.0167 (11)0.0006 (10)0.0001 (10)0.0003 (10)
C50.0157 (11)0.0177 (11)0.0212 (11)0.0001 (10)0.0010 (10)0.0009 (10)
C60.0141 (12)0.0205 (12)0.0224 (12)0.0028 (11)0.0018 (10)0.0012 (10)
C70.0190 (13)0.0151 (11)0.0203 (11)0.0003 (10)0.0016 (11)0.0005 (10)
C80.0147 (12)0.0162 (11)0.0245 (12)0.0006 (10)0.0012 (10)0.0005 (10)
C90.0141 (11)0.0168 (11)0.0188 (11)0.0024 (10)0.0012 (10)0.0011 (9)
C100.0301 (16)0.0324 (15)0.0261 (14)0.0027 (14)0.0066 (13)0.0077 (12)
C110.0269 (15)0.0205 (12)0.0299 (14)0.0045 (12)0.0007 (13)0.0056 (11)
C120.0174 (12)0.0219 (13)0.0303 (14)0.0017 (11)0.0007 (11)0.0048 (11)
C130.0281 (16)0.0254 (14)0.0377 (16)0.0065 (13)0.0004 (14)0.0040 (12)
C140.0228 (14)0.0191 (12)0.0391 (16)0.0005 (11)0.0036 (14)0.0095 (12)
C150.047 (2)0.0391 (17)0.0370 (17)0.0129 (17)0.0148 (16)0.0211 (15)
Geometric parameters (Å, º) top
O1—C11.378 (3)C3—H10.950
O1—C91.373 (3)C5—H20.950
O2—C11.209 (3)C6—H30.950
N1—C21.407 (3)C8—H40.950
N1—C101.486 (3)C10—H50.950
N1—C111.446 (3)C10—H60.950
N2—C71.378 (3)C10—H70.950
N2—C121.459 (3)C11—H80.950
N2—C141.455 (3)C11—H90.950
C1—C21.460 (3)C11—H100.950
C2—C31.352 (3)C12—H110.950
C3—C41.435 (3)C12—H120.950
C4—C51.401 (3)C13—H130.950
C4—C91.392 (3)C13—H140.950
C5—C61.373 (3)C13—H150.950
C6—C71.419 (3)C14—H160.950
C7—C81.405 (3)C14—H170.950
C8—C91.378 (3)C15—H180.950
C12—C131.529 (4)C15—H190.950
C14—C151.536 (4)C15—H200.950
C1—O1—C9123.0 (2)C9—C8—H4120.1
C2—N1—C10117.8 (2)N1—C10—H5109.4
C2—N1—C11115.2 (2)N1—C10—H6109.7
C10—N1—C11109.9 (2)N1—C10—H7109.3
C7—N2—C12120.7 (2)H5—C10—H6109.5
C7—N2—C14121.7 (2)H5—C10—H7109.5
C12—N2—C14117.3 (2)H6—C10—H7109.5
O1—C1—O2115.4 (2)N1—C11—H8109.4
O1—C1—C2117.3 (2)N1—C11—H9109.5
O2—C1—C2127.4 (2)N1—C11—H10109.5
N1—C2—C1115.7 (2)H8—C11—H9109.5
N1—C2—C3124.4 (2)H8—C11—H10109.5
C1—C2—C3119.5 (2)H9—C11—H10109.5
C2—C3—C4121.5 (2)N2—C12—H11108.7
C3—C4—C5125.1 (2)N2—C12—H12108.7
C3—C4—C9118.2 (2)C13—C12—H11108.7
C5—C4—C9116.7 (2)C13—C12—H12108.8
C4—C5—C6121.7 (2)H11—C12—H12109.5
C5—C6—C7120.9 (2)C12—C13—H13109.4
N2—C7—C6120.6 (2)C12—C13—H14109.3
N2—C7—C8121.7 (2)C12—C13—H15109.7
C6—C7—C8117.7 (2)H13—C13—H14109.5
C7—C8—C9119.7 (2)H13—C13—H15109.5
O1—C9—C4120.2 (2)H14—C13—H15109.5
O1—C9—C8116.6 (2)N2—C14—H16108.2
C4—C9—C8123.2 (2)N2—C14—H17108.5
N2—C12—C13112.5 (2)C15—C14—H16108.8
N2—C14—C15113.6 (2)C15—C14—H17108.3
C2—C3—H1119.4H16—C14—H17109.4
C4—C3—H1119.1C14—C15—H18109.9
C4—C5—H2119.2C14—C15—H19109.3
C6—C5—H2119.1C14—C15—H20109.2
C5—C6—H3119.5H18—C15—H19109.5
C7—C6—H3119.7H18—C15—H20109.5
C7—C8—H4120.2H19—C15—H20109.5
C1—O1—C9—C41.1 (3)O2—C1—C2—C3175.2 (2)
C1—O1—C9—C8179.5 (2)N1—C2—C3—C4175.2 (2)
C9—O1—C1—O2175.6 (2)C1—C2—C3—C42.5 (3)
C9—O1—C1—C25.8 (3)C2—C3—C4—C5179.95 (18)
C10—N1—C2—C155.5 (3)C2—C3—C4—C92.2 (3)
C10—N1—C2—C3131.6 (2)C3—C4—C5—C6176.8 (2)
C11—N1—C2—C1172.2 (2)C3—C4—C9—O13.0 (3)
C11—N1—C2—C30.7 (3)C3—C4—C9—C8176.4 (2)
C7—N2—C12—C1379.4 (3)C5—C4—C9—O1179.0 (2)
C12—N2—C7—C6179.0 (2)C5—C4—C9—C81.7 (3)
C12—N2—C7—C80.9 (3)C9—C4—C5—C61.1 (3)
C7—N2—C14—C1585.0 (3)C4—C5—C6—C70.8 (4)
C14—N2—C7—C65.2 (3)C5—C6—C7—N2177.8 (2)
C14—N2—C7—C8174.7 (2)C5—C6—C7—C82.1 (3)
C12—N2—C14—C15101.0 (3)N2—C7—C8—C9178.4 (2)
C14—N2—C12—C1394.7 (3)C6—C7—C8—C91.5 (3)
O1—C1—C2—N1179.7 (2)C7—C8—C9—O1179.7 (2)
O1—C1—C2—C36.4 (3)C7—C8—C9—C40.4 (4)
O2—C1—C2—N11.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H1···O2i0.952.453.380 (3)166 (1)
C5—H2···O1i0.952.713.599 (3)157 (1)
C11—H9···O2i0.952.713.230 (4)115 (1)
C15—H19···O1ii0.952.593.479 (4)155 (1)
C5—H2···Cpiii0.953.093.44104
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+2, z1/2; (iii) x1/2, y+3/2, z+1.
A comparison of selected bond lengths in (I) with related distances in coumarin (Å) top
Bond lengthCompound (I)Coumarin*
C1-C21.460 (3)1.448 (5)
C2-C31.352 (3)1.344 (5)
C3-C41.435 (3)1.432 (5)
C4-C51.401 (3)1.390 (5)
C4-C91.392 (3)1.395 (4)
C5-C61.373 (3)1.369 (5)
C6-C71.419 (3)1.368 (6)
C7-C81.405 (3)1.392 (5)
C8-C91.378 (3)1.383 (5)
O1-C11.378 (3)1.367 (4)
O1-C91.373 (3)1.378 (4)
O2-C11.209 (3)1.205 (5)
N1-C21.407 (3)
N1-C101.486 (3)
N1-C111.446 (3)
N2-C71.378 (3)
N2-C121.459 (3)
N2-C141.455 (3)
C12-C131.529 (4)
C14-C151.536 (4)
Notes: (*) Gavuzzo et al. (1974).
 

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