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In the title compound, C
15H
20N
2O
2, 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
CCDC reference: 283906
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (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
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-2
H-1-benzopyran-2-one
top
Crystal data top
C15H20N2O2 | F(000) = 560.00 |
Mr = 260.34 | Dx = 1.255 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4379 reflections |
a = 6.596 (3) Å | θ = 3.1–27.5° |
b = 14.360 (6) Å | µ = 0.08 mm−1 |
c = 14.549 (6) Å | T = 123 K |
V = 1378.0 (10) Å3 | Prism, orange |
Z = 4 | 0.15 × 0.14 × 0.10 mm |
Data collection top
Rigaku Saturn diffractometer | 1467 reflections with F2 > 2σ(F2) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.138 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (REQAB; Jacobson, 1998) | h = −8→8 |
Tmin = 0.987, Tmax = 0.992 | k = −18→18 |
11200 measured reflections | l = −18→18 |
1823 independent reflections | |
Refinement top
Refinement on F2 | H-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 = 1.00 | Δρmax = 0.31 e Å−3 |
1817 reflections | Δρmin = −0.31 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.3225 (2) | 0.81266 (12) | 0.61901 (13) | 0.0199 (4) | |
O2 | 0.4480 (3) | 0.70325 (14) | 0.70694 (16) | 0.0285 (5) | |
N1 | 0.0639 (3) | 0.62869 (14) | 0.74974 (14) | 0.0195 (5) | |
N2 | 0.1079 (3) | 1.05384 (17) | 0.41548 (17) | 0.0229 (5) | |
C1 | 0.2947 (4) | 0.73664 (19) | 0.67543 (19) | 0.0197 (6) | |
C2 | 0.0864 (4) | 0.70677 (18) | 0.69226 (19) | 0.0171 (5) | |
C3 | −0.0671 (4) | 0.74784 (17) | 0.64592 (18) | 0.0156 (5) | |
C4 | −0.0313 (4) | 0.82297 (19) | 0.58296 (18) | 0.0160 (5) | |
C5 | −0.1815 (4) | 0.86916 (18) | 0.53231 (18) | 0.0182 (5) | |
C6 | −0.1366 (4) | 0.94350 (19) | 0.47660 (19) | 0.0190 (6) | |
C7 | 0.0650 (4) | 0.97726 (18) | 0.46916 (18) | 0.0181 (6) | |
C8 | 0.2170 (4) | 0.93009 (18) | 0.51819 (18) | 0.0185 (6) | |
C9 | 0.1664 (4) | 0.85518 (18) | 0.57280 (18) | 0.0165 (5) | |
C10 | 0.1576 (5) | 0.6327 (2) | 0.8426 (2) | 0.0295 (7) | |
C11 | −0.1400 (4) | 0.5923 (2) | 0.7563 (2) | 0.0258 (7) | |
C12 | 0.3145 (4) | 1.0897 (2) | 0.4088 (2) | 0.0232 (6) | |
C13 | 0.3738 (5) | 1.1489 (2) | 0.4919 (2) | 0.0304 (7) | |
C14 | −0.0515 (4) | 1.1073 (2) | 0.3710 (2) | 0.0270 (7) | |
C15 | −0.1177 (5) | 1.0672 (2) | 0.2778 (2) | 0.0409 (9) | |
H1 | −0.2020 | 0.7267 | 0.6553 | 0.019* | |
H2 | −0.3180 | 0.8486 | 0.5367 | 0.022* | |
H3 | −0.2418 | 0.9725 | 0.4425 | 0.023* | |
H4 | 0.3543 | 0.9497 | 0.5137 | 0.022* | |
H5 | 0.0627 | 0.6577 | 0.8851 | 0.035* | |
H6 | 0.1955 | 0.5718 | 0.8615 | 0.035* | |
H7 | 0.2744 | 0.6713 | 0.8406 | 0.036* | |
H8 | −0.1967 | 0.5874 | 0.6964 | 0.031* | |
H9 | −0.2205 | 0.6331 | 0.7924 | 0.031* | |
H10 | −0.1369 | 0.5325 | 0.7842 | 0.031* | |
H11 | 0.3249 | 1.1268 | 0.3550 | 0.028* | |
H12 | 0.4053 | 1.0385 | 0.4044 | 0.028* | |
H13 | 0.4324 | 1.1101 | 0.5376 | 0.037* | |
H14 | 0.4695 | 1.1946 | 0.4734 | 0.037* | |
H15 | 0.2569 | 1.1787 | 0.5162 | 0.037* | |
H16 | −0.0033 | 1.1690 | 0.3619 | 0.032* | |
H17 | −0.1662 | 1.1086 | 0.4104 | 0.032* | |
H18 | −0.1330 | 1.0015 | 0.2823 | 0.049* | |
H19 | −0.0179 | 1.0813 | 0.2328 | 0.049* | |
H20 | −0.2433 | 1.0943 | 0.2604 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0138 (8) | 0.0187 (8) | 0.0273 (10) | 0.0002 (7) | −0.0025 (8) | 0.0043 (7) |
O2 | 0.0146 (9) | 0.0304 (10) | 0.0403 (12) | 0.0006 (9) | −0.0049 (9) | 0.0105 (9) |
N1 | 0.0202 (11) | 0.0178 (10) | 0.0206 (10) | 0.0007 (10) | −0.0015 (10) | 0.0050 (9) |
N2 | 0.0180 (11) | 0.0204 (11) | 0.0302 (12) | −0.0025 (10) | −0.0021 (10) | 0.0085 (9) |
C1 | 0.0195 (13) | 0.0181 (12) | 0.0216 (13) | −0.0007 (11) | −0.0001 (11) | 0.0005 (10) |
C2 | 0.0172 (12) | 0.0141 (10) | 0.0201 (12) | 0.0002 (10) | 0.0017 (10) | −0.0036 (10) |
C3 | 0.0129 (11) | 0.0153 (11) | 0.0185 (11) | −0.0020 (9) | 0.0031 (10) | −0.0020 (9) |
C4 | 0.0144 (11) | 0.0170 (11) | 0.0167 (11) | 0.0006 (10) | 0.0001 (10) | −0.0003 (10) |
C5 | 0.0157 (11) | 0.0177 (11) | 0.0212 (11) | −0.0001 (10) | 0.0010 (10) | 0.0009 (10) |
C6 | 0.0141 (12) | 0.0205 (12) | 0.0224 (12) | 0.0028 (11) | −0.0018 (10) | 0.0012 (10) |
C7 | 0.0190 (13) | 0.0151 (11) | 0.0203 (11) | −0.0003 (10) | 0.0016 (11) | −0.0005 (10) |
C8 | 0.0147 (12) | 0.0162 (11) | 0.0245 (12) | 0.0006 (10) | 0.0012 (10) | 0.0005 (10) |
C9 | 0.0141 (11) | 0.0168 (11) | 0.0188 (11) | 0.0024 (10) | −0.0012 (10) | −0.0011 (9) |
C10 | 0.0301 (16) | 0.0324 (15) | 0.0261 (14) | −0.0027 (14) | −0.0066 (13) | 0.0077 (12) |
C11 | 0.0269 (15) | 0.0205 (12) | 0.0299 (14) | −0.0045 (12) | 0.0007 (13) | 0.0056 (11) |
C12 | 0.0174 (12) | 0.0219 (13) | 0.0303 (14) | −0.0017 (11) | 0.0007 (11) | 0.0048 (11) |
C13 | 0.0281 (16) | 0.0254 (14) | 0.0377 (16) | −0.0065 (13) | −0.0004 (14) | −0.0040 (12) |
C14 | 0.0228 (14) | 0.0191 (12) | 0.0391 (16) | 0.0005 (11) | −0.0036 (14) | 0.0095 (12) |
C15 | 0.047 (2) | 0.0391 (17) | 0.0370 (17) | −0.0129 (17) | −0.0148 (16) | 0.0211 (15) |
Geometric parameters (Å, º) top
O1—C1 | 1.378 (3) | C3—H1 | 0.950 |
O1—C9 | 1.373 (3) | C5—H2 | 0.950 |
O2—C1 | 1.209 (3) | C6—H3 | 0.950 |
N1—C2 | 1.407 (3) | C8—H4 | 0.950 |
N1—C10 | 1.486 (3) | C10—H5 | 0.950 |
N1—C11 | 1.446 (3) | C10—H6 | 0.950 |
N2—C7 | 1.378 (3) | C10—H7 | 0.950 |
N2—C12 | 1.459 (3) | C11—H8 | 0.950 |
N2—C14 | 1.455 (3) | C11—H9 | 0.950 |
C1—C2 | 1.460 (3) | C11—H10 | 0.950 |
C2—C3 | 1.352 (3) | C12—H11 | 0.950 |
C3—C4 | 1.435 (3) | C12—H12 | 0.950 |
C4—C5 | 1.401 (3) | C13—H13 | 0.950 |
C4—C9 | 1.392 (3) | C13—H14 | 0.950 |
C5—C6 | 1.373 (3) | C13—H15 | 0.950 |
C6—C7 | 1.419 (3) | C14—H16 | 0.950 |
C7—C8 | 1.405 (3) | C14—H17 | 0.950 |
C8—C9 | 1.378 (3) | C15—H18 | 0.950 |
C12—C13 | 1.529 (4) | C15—H19 | 0.950 |
C14—C15 | 1.536 (4) | C15—H20 | 0.950 |
| | | |
C1—O1—C9 | 123.0 (2) | C9—C8—H4 | 120.1 |
C2—N1—C10 | 117.8 (2) | N1—C10—H5 | 109.4 |
C2—N1—C11 | 115.2 (2) | N1—C10—H6 | 109.7 |
C10—N1—C11 | 109.9 (2) | N1—C10—H7 | 109.3 |
C7—N2—C12 | 120.7 (2) | H5—C10—H6 | 109.5 |
C7—N2—C14 | 121.7 (2) | H5—C10—H7 | 109.5 |
C12—N2—C14 | 117.3 (2) | H6—C10—H7 | 109.5 |
O1—C1—O2 | 115.4 (2) | N1—C11—H8 | 109.4 |
O1—C1—C2 | 117.3 (2) | N1—C11—H9 | 109.5 |
O2—C1—C2 | 127.4 (2) | N1—C11—H10 | 109.5 |
N1—C2—C1 | 115.7 (2) | H8—C11—H9 | 109.5 |
N1—C2—C3 | 124.4 (2) | H8—C11—H10 | 109.5 |
C1—C2—C3 | 119.5 (2) | H9—C11—H10 | 109.5 |
C2—C3—C4 | 121.5 (2) | N2—C12—H11 | 108.7 |
C3—C4—C5 | 125.1 (2) | N2—C12—H12 | 108.7 |
C3—C4—C9 | 118.2 (2) | C13—C12—H11 | 108.7 |
C5—C4—C9 | 116.7 (2) | C13—C12—H12 | 108.8 |
C4—C5—C6 | 121.7 (2) | H11—C12—H12 | 109.5 |
C5—C6—C7 | 120.9 (2) | C12—C13—H13 | 109.4 |
N2—C7—C6 | 120.6 (2) | C12—C13—H14 | 109.3 |
N2—C7—C8 | 121.7 (2) | C12—C13—H15 | 109.7 |
C6—C7—C8 | 117.7 (2) | H13—C13—H14 | 109.5 |
C7—C8—C9 | 119.7 (2) | H13—C13—H15 | 109.5 |
O1—C9—C4 | 120.2 (2) | H14—C13—H15 | 109.5 |
O1—C9—C8 | 116.6 (2) | N2—C14—H16 | 108.2 |
C4—C9—C8 | 123.2 (2) | N2—C14—H17 | 108.5 |
N2—C12—C13 | 112.5 (2) | C15—C14—H16 | 108.8 |
N2—C14—C15 | 113.6 (2) | C15—C14—H17 | 108.3 |
C2—C3—H1 | 119.4 | H16—C14—H17 | 109.4 |
C4—C3—H1 | 119.1 | C14—C15—H18 | 109.9 |
C4—C5—H2 | 119.2 | C14—C15—H19 | 109.3 |
C6—C5—H2 | 119.1 | C14—C15—H20 | 109.2 |
C5—C6—H3 | 119.5 | H18—C15—H19 | 109.5 |
C7—C6—H3 | 119.7 | H18—C15—H20 | 109.5 |
C7—C8—H4 | 120.2 | H19—C15—H20 | 109.5 |
| | | |
C1—O1—C9—C4 | 1.1 (3) | O2—C1—C2—C3 | −175.2 (2) |
C1—O1—C9—C8 | −179.5 (2) | N1—C2—C3—C4 | −175.2 (2) |
C9—O1—C1—O2 | 175.6 (2) | C1—C2—C3—C4 | −2.5 (3) |
C9—O1—C1—C2 | −5.8 (3) | C2—C3—C4—C5 | 179.95 (18) |
C10—N1—C2—C1 | 55.5 (3) | C2—C3—C4—C9 | −2.2 (3) |
C10—N1—C2—C3 | −131.6 (2) | C3—C4—C5—C6 | 176.8 (2) |
C11—N1—C2—C1 | −172.2 (2) | C3—C4—C9—O1 | 3.0 (3) |
C11—N1—C2—C3 | 0.7 (3) | C3—C4—C9—C8 | −176.4 (2) |
C7—N2—C12—C13 | −79.4 (3) | C5—C4—C9—O1 | −179.0 (2) |
C12—N2—C7—C6 | 179.0 (2) | C5—C4—C9—C8 | 1.7 (3) |
C12—N2—C7—C8 | −0.9 (3) | C9—C4—C5—C6 | −1.1 (3) |
C7—N2—C14—C15 | −85.0 (3) | C4—C5—C6—C7 | −0.8 (4) |
C14—N2—C7—C6 | 5.2 (3) | C5—C6—C7—N2 | −177.8 (2) |
C14—N2—C7—C8 | −174.7 (2) | C5—C6—C7—C8 | 2.1 (3) |
C12—N2—C14—C15 | 101.0 (3) | N2—C7—C8—C9 | 178.4 (2) |
C14—N2—C12—C13 | 94.7 (3) | C6—C7—C8—C9 | −1.5 (3) |
O1—C1—C2—N1 | 179.7 (2) | C7—C8—C9—O1 | −179.7 (2) |
O1—C1—C2—C3 | 6.4 (3) | C7—C8—C9—C4 | −0.4 (4) |
O2—C1—C2—N1 | −1.9 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H1···O2i | 0.95 | 2.45 | 3.380 (3) | 166 (1) |
C5—H2···O1i | 0.95 | 2.71 | 3.599 (3) | 157 (1) |
C11—H9···O2i | 0.95 | 2.71 | 3.230 (4) | 115 (1) |
C15—H19···O1ii | 0.95 | 2.59 | 3.479 (4) | 155 (1) |
C5—H2···Cpiii | 0.95 | 3.09 | 3.44 | 104 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, −y+2, z−1/2; (iii) x−1/2, −y+3/2, −z+1. |
A comparison of selected bond lengths in (I) with related distances in coumarin
(Å) topBond length | Compound (I) | Coumarin* |
C1-C2 | 1.460 (3) | 1.448 (5) |
C2-C3 | 1.352 (3) | 1.344 (5) |
C3-C4 | 1.435 (3) | 1.432 (5) |
C4-C5 | 1.401 (3) | 1.390 (5) |
C4-C9 | 1.392 (3) | 1.395 (4) |
C5-C6 | 1.373 (3) | 1.369 (5) |
C6-C7 | 1.419 (3) | 1.368 (6) |
C7-C8 | 1.405 (3) | 1.392 (5) |
C8-C9 | 1.378 (3) | 1.383 (5) |
O1-C1 | 1.378 (3) | 1.367 (4) |
O1-C9 | 1.373 (3) | 1.378 (4) |
O2-C1 | 1.209 (3) | 1.205 (5) |
N1-C2 | 1.407 (3) | |
N1-C10 | 1.486 (3) | |
N1-C11 | 1.446 (3) | |
N2-C7 | 1.378 (3) | |
N2-C12 | 1.459 (3) | |
N2-C14 | 1.455 (3) | |
C12-C13 | 1.529 (4) | |
C14-C15 | 1.536 (4) | |
Notes: (*) Gavuzzo et al. (1974). |
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