In the title compound, the benzodiazole unit is planar while the benzyl and propynyl substituents are rotated significantly out of this plane.
Supporting information
CCDC reference: 1879758
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.108
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.308 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 8 Report
Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 3 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
4 ALERT level G = General information/check it is not something unexpected
1 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
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae, et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
1-Benzyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1
H-1,3-benzodiazol-2-one
top
Crystal data top
C17H14N2O | F(000) = 552 |
Mr = 262.30 | Dx = 1.278 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 8.3567 (2) Å | Cell parameters from 9908 reflections |
b = 9.2040 (2) Å | θ = 2.5–74.9° |
c = 17.7868 (4) Å | µ = 0.64 mm−1 |
β = 94.559 (1)° | T = 298 K |
V = 1363.74 (5) Å3 | Block, colourless |
Z = 4 | 0.23 × 0.20 × 0.19 mm |
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2433 reflections with I > 2σ(I) |
Radiation source: INCOATEC IµS micro-focus source | Rint = 0.032 |
ω scans | θmax = 74.4°, θmin = 5.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −10→10 |
Tmin = 0.86, Tmax = 0.89 | k = −11→11 |
13551 measured reflections | l = −22→21 |
2778 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | All H-atom parameters refined |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0559P)2 + 0.1595P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2778 reflections | Δρmax = 0.15 e Å−3 |
238 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/1 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0123 (10) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.22681 (15) | 0.83445 (11) | 0.40629 (6) | 0.0792 (3) | |
N1 | 0.34376 (12) | 0.66295 (10) | 0.33147 (5) | 0.0533 (3) | |
N2 | 0.17477 (12) | 0.82074 (10) | 0.27629 (6) | 0.0543 (3) | |
C1 | 0.22401 (13) | 0.73060 (12) | 0.22001 (6) | 0.0491 (3) | |
C2 | 0.18494 (17) | 0.72757 (15) | 0.14354 (7) | 0.0629 (3) | |
H2 | 0.1121 (19) | 0.7990 (18) | 0.1214 (9) | 0.075 (4)* | |
C3 | 0.2547 (2) | 0.62075 (18) | 0.10228 (8) | 0.0734 (4) | |
H3 | 0.234 (2) | 0.617 (2) | 0.0472 (10) | 0.090 (5)* | |
C4 | 0.3609 (2) | 0.52123 (16) | 0.13680 (8) | 0.0703 (4) | |
H4 | 0.414 (2) | 0.4500 (18) | 0.1060 (9) | 0.077 (4)* | |
C5 | 0.40140 (16) | 0.52408 (14) | 0.21399 (8) | 0.0590 (3) | |
H5 | 0.476 (2) | 0.4532 (18) | 0.2392 (9) | 0.077 (4)* | |
C6 | 0.33092 (13) | 0.63007 (12) | 0.25513 (6) | 0.0478 (3) | |
C7 | 0.24590 (16) | 0.77932 (13) | 0.34550 (7) | 0.0555 (3) | |
C8 | 0.06278 (18) | 0.94116 (15) | 0.26623 (10) | 0.0675 (4) | |
H8A | −0.034 (2) | 0.908 (2) | 0.2331 (11) | 0.095 (6)* | |
H8B | 0.030 (2) | 0.965 (2) | 0.3179 (11) | 0.089 (5)* | |
C9 | 0.13423 (17) | 1.06640 (14) | 0.23111 (8) | 0.0633 (3) | |
C10 | 0.1922 (2) | 1.16568 (17) | 0.20289 (11) | 0.0854 (5) | |
H10 | 0.236 (3) | 1.249 (3) | 0.1798 (13) | 0.132 (8)* | |
C11 | 0.43747 (17) | 0.58361 (15) | 0.39115 (8) | 0.0600 (3) | |
H11A | 0.539 (2) | 0.5429 (18) | 0.3684 (9) | 0.080 (5)* | |
H11B | 0.4649 (19) | 0.6538 (18) | 0.4327 (10) | 0.080 (5)* | |
C12 | 0.34639 (14) | 0.45907 (12) | 0.42256 (6) | 0.0512 (3) | |
C13 | 0.23968 (18) | 0.48403 (17) | 0.47628 (8) | 0.0675 (4) | |
H13 | 0.223 (2) | 0.587 (2) | 0.4938 (9) | 0.087 (5)* | |
C14 | 0.1570 (2) | 0.3702 (2) | 0.50568 (10) | 0.0819 (5) | |
H14 | 0.086 (2) | 0.387 (2) | 0.5429 (12) | 0.107 (6)* | |
C15 | 0.1808 (2) | 0.2308 (2) | 0.48218 (11) | 0.0830 (5) | |
H15 | 0.123 (2) | 0.154 (2) | 0.5025 (10) | 0.095 (6)* | |
C16 | 0.2874 (3) | 0.20500 (18) | 0.42939 (11) | 0.0870 (5) | |
H16 | 0.306 (2) | 0.104 (2) | 0.4124 (11) | 0.106 (6)* | |
C17 | 0.3696 (2) | 0.31841 (15) | 0.39958 (9) | 0.0701 (4) | |
H17 | 0.446 (2) | 0.299 (2) | 0.3599 (12) | 0.103 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1247 (9) | 0.0571 (6) | 0.0569 (5) | 0.0079 (5) | 0.0134 (5) | −0.0057 (4) |
N1 | 0.0663 (6) | 0.0445 (5) | 0.0475 (5) | 0.0034 (4) | −0.0042 (4) | 0.0037 (4) |
N2 | 0.0612 (6) | 0.0435 (5) | 0.0583 (6) | 0.0059 (4) | 0.0049 (4) | 0.0066 (4) |
C1 | 0.0519 (6) | 0.0436 (6) | 0.0512 (6) | −0.0061 (4) | 0.0006 (4) | 0.0055 (4) |
C2 | 0.0717 (8) | 0.0593 (7) | 0.0557 (7) | −0.0085 (6) | −0.0081 (6) | 0.0106 (6) |
C3 | 0.1009 (11) | 0.0707 (9) | 0.0478 (7) | −0.0184 (8) | 0.0008 (7) | 0.0001 (6) |
C4 | 0.0940 (10) | 0.0571 (8) | 0.0619 (8) | −0.0090 (7) | 0.0197 (7) | −0.0083 (6) |
C5 | 0.0661 (7) | 0.0469 (6) | 0.0645 (7) | 0.0002 (5) | 0.0090 (6) | 0.0013 (5) |
C6 | 0.0524 (6) | 0.0413 (5) | 0.0493 (6) | −0.0050 (4) | 0.0014 (4) | 0.0035 (4) |
C7 | 0.0727 (8) | 0.0420 (6) | 0.0520 (6) | −0.0020 (5) | 0.0054 (5) | 0.0027 (5) |
C8 | 0.0649 (8) | 0.0524 (7) | 0.0868 (10) | 0.0123 (6) | 0.0158 (7) | 0.0174 (7) |
C9 | 0.0715 (8) | 0.0472 (6) | 0.0723 (8) | 0.0125 (6) | 0.0130 (6) | 0.0067 (6) |
C10 | 0.1019 (12) | 0.0519 (8) | 0.1070 (13) | 0.0087 (8) | 0.0373 (10) | 0.0107 (8) |
C11 | 0.0641 (7) | 0.0574 (7) | 0.0560 (7) | −0.0024 (6) | −0.0113 (6) | 0.0091 (6) |
C12 | 0.0549 (6) | 0.0490 (6) | 0.0478 (6) | 0.0059 (5) | −0.0082 (5) | 0.0057 (5) |
C13 | 0.0748 (8) | 0.0627 (8) | 0.0652 (8) | 0.0149 (7) | 0.0066 (6) | 0.0057 (6) |
C14 | 0.0666 (8) | 0.0971 (12) | 0.0833 (10) | 0.0159 (8) | 0.0131 (8) | 0.0295 (9) |
C15 | 0.0703 (9) | 0.0791 (11) | 0.0967 (12) | −0.0107 (8) | −0.0120 (8) | 0.0368 (9) |
C16 | 0.1131 (14) | 0.0506 (8) | 0.0956 (12) | −0.0019 (8) | −0.0018 (10) | 0.0065 (8) |
C17 | 0.0896 (10) | 0.0526 (7) | 0.0687 (8) | 0.0097 (7) | 0.0099 (7) | 0.0036 (6) |
Geometric parameters (Å, º) top
O1—C7 | 1.2163 (15) | C8—H8A | 1.01 (2) |
N1—C7 | 1.3823 (16) | C8—H8B | 1.004 (18) |
N1—C6 | 1.3869 (15) | C9—C10 | 1.166 (2) |
N1—C11 | 1.4632 (15) | C10—H10 | 0.95 (2) |
N2—C7 | 1.3775 (16) | C11—C12 | 1.5076 (17) |
N2—C1 | 1.3875 (15) | C11—H11A | 1.042 (17) |
N2—C8 | 1.4525 (16) | C11—H11B | 0.995 (18) |
C1—C2 | 1.3737 (17) | C12—C17 | 1.3761 (18) |
C1—C6 | 1.3985 (16) | C12—C13 | 1.3771 (19) |
C2—C3 | 1.383 (2) | C13—C14 | 1.381 (2) |
C2—H2 | 0.959 (17) | C13—H13 | 1.008 (19) |
C3—C4 | 1.384 (2) | C14—C15 | 1.369 (3) |
C3—H3 | 0.982 (18) | C14—H14 | 0.94 (2) |
C4—C5 | 1.388 (2) | C15—C16 | 1.366 (3) |
C4—H4 | 0.983 (17) | C15—H15 | 0.94 (2) |
C5—C6 | 1.3793 (17) | C16—C17 | 1.379 (2) |
C5—H5 | 0.986 (17) | C16—H16 | 0.99 (2) |
C8—C9 | 1.4610 (19) | C17—H17 | 1.00 (2) |
| | | |
O1···H8B | 2.492 (18) | C5···H11A | 2.897 (16) |
O1···H11B | 2.607 (16) | C5···H10vi | 2.93 (3) |
O1···H13 | 2.760 (18) | C8···H2 | 2.947 (16) |
O1···H16i | 2.568 (18) | C10···H8Aii | 2.874 (18) |
C2···C9 | 3.5265 (19) | C10···H14iii | 2.95 (2) |
C7···C13 | 3.5805 (19) | C10···H11Avii | 2.895 (17) |
C9···C1ii | 3.5236 (18) | C11···H5 | 2.998 (16) |
C10···N2ii | 3.4291 (19) | C13···H14v | 2.964 (17) |
C10···C8ii | 3.385 (2) | H3···O1iii | 2.542 (18) |
C10···C14iii | 3.512 (3) | H5···H11A | 2.46 (2) |
C11···C13iv | 3.495 (2) | H11A···H17 | 2.38 (2) |
C14···C14v | 3.543 (2) | H11B···H13 | 2.45 (2) |
C4···H10vi | 2.84 (3) | | |
| | | |
C7—N1—C6 | 110.18 (9) | N2—C8—H8B | 105.8 (10) |
C7—N1—C11 | 123.09 (10) | C9—C8—H8B | 111.9 (11) |
C6—N1—C11 | 126.62 (10) | H8A—C8—H8B | 109.7 (15) |
C7—N2—C1 | 110.34 (9) | C10—C9—C8 | 179.48 (16) |
C7—N2—C8 | 123.32 (11) | C9—C10—H10 | 178.1 (14) |
C1—N2—C8 | 126.34 (11) | N1—C11—C12 | 113.05 (10) |
C2—C1—N2 | 131.74 (11) | N1—C11—H11A | 107.8 (9) |
C2—C1—C6 | 121.46 (11) | C12—C11—H11A | 108.8 (9) |
N2—C1—C6 | 106.80 (10) | N1—C11—H11B | 107.1 (10) |
C1—C2—C3 | 117.56 (13) | C12—C11—H11B | 108.2 (9) |
C1—C2—H2 | 119.0 (10) | H11A—C11—H11B | 112.0 (13) |
C3—C2—H2 | 123.4 (10) | C17—C12—C13 | 118.52 (13) |
C2—C3—C4 | 121.16 (13) | C17—C12—C11 | 121.19 (12) |
C2—C3—H3 | 120.6 (11) | C13—C12—C11 | 120.28 (12) |
C4—C3—H3 | 118.2 (11) | C12—C13—C14 | 120.50 (15) |
C3—C4—C5 | 121.56 (14) | C12—C13—H13 | 119.1 (10) |
C3—C4—H4 | 119.7 (10) | C14—C13—H13 | 120.4 (10) |
C5—C4—H4 | 118.6 (10) | C15—C14—C13 | 120.41 (16) |
C6—C5—C4 | 117.22 (13) | C15—C14—H14 | 119.1 (14) |
C6—C5—H5 | 120.5 (10) | C13—C14—H14 | 120.5 (14) |
C4—C5—H5 | 122.3 (10) | C16—C15—C14 | 119.46 (16) |
C5—C6—N1 | 132.12 (11) | C16—C15—H15 | 120.9 (11) |
C5—C6—C1 | 121.03 (11) | C14—C15—H15 | 119.6 (11) |
N1—C6—C1 | 106.85 (10) | C15—C16—C17 | 120.33 (16) |
O1—C7—N2 | 126.95 (12) | C15—C16—H16 | 119.8 (12) |
O1—C7—N1 | 127.23 (12) | C17—C16—H16 | 119.8 (12) |
N2—C7—N1 | 105.82 (10) | C12—C17—C16 | 120.78 (15) |
N2—C8—C9 | 111.93 (11) | C12—C17—H17 | 119.1 (11) |
N2—C8—H8A | 108.6 (11) | C16—C17—H17 | 120.1 (11) |
C9—C8—H8A | 108.8 (11) | | |
| | | |
C7—N2—C1—C2 | 179.03 (13) | C1—N2—C7—N1 | 1.23 (13) |
C8—N2—C1—C2 | −0.1 (2) | C8—N2—C7—N1 | −179.61 (11) |
C7—N2—C1—C6 | −0.58 (13) | C6—N1—C7—O1 | 178.85 (13) |
C8—N2—C1—C6 | −179.71 (11) | C11—N1—C7—O1 | 2.4 (2) |
N2—C1—C2—C3 | −179.26 (12) | C6—N1—C7—N2 | −1.44 (13) |
C6—C1—C2—C3 | 0.29 (18) | C11—N1—C7—N2 | −177.93 (11) |
C1—C2—C3—C4 | −0.4 (2) | C7—N2—C8—C9 | 107.51 (15) |
C2—C3—C4—C5 | 0.2 (2) | C1—N2—C8—C9 | −73.46 (18) |
C3—C4—C5—C6 | 0.2 (2) | C7—N1—C11—C12 | 88.90 (15) |
C4—C5—C6—N1 | 179.75 (12) | C6—N1—C11—C12 | −87.00 (15) |
C4—C5—C6—C1 | −0.37 (18) | N1—C11—C12—C17 | 99.61 (15) |
C7—N1—C6—C5 | −179.00 (12) | N1—C11—C12—C13 | −81.60 (15) |
C11—N1—C6—C5 | −2.7 (2) | C17—C12—C13—C14 | −0.6 (2) |
C7—N1—C6—C1 | 1.11 (13) | C11—C12—C13—C14 | −179.46 (13) |
C11—N1—C6—C1 | 177.44 (11) | C12—C13—C14—C15 | 0.4 (2) |
C2—C1—C6—C5 | 0.12 (17) | C13—C14—C15—C16 | 0.1 (3) |
N2—C1—C6—C5 | 179.78 (10) | C14—C15—C16—C17 | −0.5 (3) |
C2—C1—C6—N1 | −179.98 (11) | C13—C12—C17—C16 | 0.3 (2) |
N2—C1—C6—N1 | −0.32 (12) | C11—C12—C17—C16 | 179.09 (14) |
C1—N2—C7—O1 | −179.06 (13) | C15—C16—C17—C12 | 0.3 (3) |
C8—N2—C7—O1 | 0.1 (2) | | |
Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) x, y−1, z; (vii) −x+1, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) topCg2 is the centroid of the C1–C6 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1iii | 0.982 (18) | 2.542 (18) | 3.4997 (18) | 165.1 (14) |
C16—H16···O1vi | 0.994 (18) | 2.568 (18) | 3.468 (2) | 150.6 (14) |
C17—H17···Cg2viii | 1.00 (2) | 2.831 (18) | 3.6964 (17) | 144.6 (15) |
Symmetry codes: (iii) x, −y+3/2, z−1/2; (vi) x, y−1, z; (viii) −x+1, y−1/2, −z+1/2. |