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In the title compound, the benzo­diazole unit is planar while the benzyl and propynyl substituents are rotated significantly out of this plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018016298/xu5952sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018016298/xu5952Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2056989018016298/xu5952Isup3.cdx
Supplementary material

CCDC reference: 1879758

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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-1H-1,3-benzodiazol-2-one top
Crystal data top
C17H14N2OF(000) = 552
Mr = 262.30Dx = 1.278 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 8.3567 (2) ÅCell parameters from 9908 reflections
b = 9.2040 (2) Åθ = 2.5–74.9°
c = 17.7868 (4) ŵ = 0.64 mm1
β = 94.559 (1)°T = 298 K
V = 1363.74 (5) Å3Block, colourless
Z = 40.23 × 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 sourceRint = 0.032
ω scansθmax = 74.4°, θmin = 5.0°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1010
Tmin = 0.86, Tmax = 0.89k = 1111
13551 measured reflectionsl = 2221
2778 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038All 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 reflectionsΔρmax = 0.15 e Å3
238 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL-2018/1 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.22681 (15)0.83445 (11)0.40629 (6)0.0792 (3)
N10.34376 (12)0.66295 (10)0.33147 (5)0.0533 (3)
N20.17477 (12)0.82074 (10)0.27629 (6)0.0543 (3)
C10.22401 (13)0.73060 (12)0.22001 (6)0.0491 (3)
C20.18494 (17)0.72757 (15)0.14354 (7)0.0629 (3)
H20.1121 (19)0.7990 (18)0.1214 (9)0.075 (4)*
C30.2547 (2)0.62075 (18)0.10228 (8)0.0734 (4)
H30.234 (2)0.617 (2)0.0472 (10)0.090 (5)*
C40.3609 (2)0.52123 (16)0.13680 (8)0.0703 (4)
H40.414 (2)0.4500 (18)0.1060 (9)0.077 (4)*
C50.40140 (16)0.52408 (14)0.21399 (8)0.0590 (3)
H50.476 (2)0.4532 (18)0.2392 (9)0.077 (4)*
C60.33092 (13)0.63007 (12)0.25513 (6)0.0478 (3)
C70.24590 (16)0.77932 (13)0.34550 (7)0.0555 (3)
C80.06278 (18)0.94116 (15)0.26623 (10)0.0675 (4)
H8A0.034 (2)0.908 (2)0.2331 (11)0.095 (6)*
H8B0.030 (2)0.965 (2)0.3179 (11)0.089 (5)*
C90.13423 (17)1.06640 (14)0.23111 (8)0.0633 (3)
C100.1922 (2)1.16568 (17)0.20289 (11)0.0854 (5)
H100.236 (3)1.249 (3)0.1798 (13)0.132 (8)*
C110.43747 (17)0.58361 (15)0.39115 (8)0.0600 (3)
H11A0.539 (2)0.5429 (18)0.3684 (9)0.080 (5)*
H11B0.4649 (19)0.6538 (18)0.4327 (10)0.080 (5)*
C120.34639 (14)0.45907 (12)0.42256 (6)0.0512 (3)
C130.23968 (18)0.48403 (17)0.47628 (8)0.0675 (4)
H130.223 (2)0.587 (2)0.4938 (9)0.087 (5)*
C140.1570 (2)0.3702 (2)0.50568 (10)0.0819 (5)
H140.086 (2)0.387 (2)0.5429 (12)0.107 (6)*
C150.1808 (2)0.2308 (2)0.48218 (11)0.0830 (5)
H150.123 (2)0.154 (2)0.5025 (10)0.095 (6)*
C160.2874 (3)0.20500 (18)0.42939 (11)0.0870 (5)
H160.306 (2)0.104 (2)0.4124 (11)0.106 (6)*
C170.3696 (2)0.31841 (15)0.39958 (9)0.0701 (4)
H170.446 (2)0.299 (2)0.3599 (12)0.103 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1247 (9)0.0571 (6)0.0569 (5)0.0079 (5)0.0134 (5)0.0057 (4)
N10.0663 (6)0.0445 (5)0.0475 (5)0.0034 (4)0.0042 (4)0.0037 (4)
N20.0612 (6)0.0435 (5)0.0583 (6)0.0059 (4)0.0049 (4)0.0066 (4)
C10.0519 (6)0.0436 (6)0.0512 (6)0.0061 (4)0.0006 (4)0.0055 (4)
C20.0717 (8)0.0593 (7)0.0557 (7)0.0085 (6)0.0081 (6)0.0106 (6)
C30.1009 (11)0.0707 (9)0.0478 (7)0.0184 (8)0.0008 (7)0.0001 (6)
C40.0940 (10)0.0571 (8)0.0619 (8)0.0090 (7)0.0197 (7)0.0083 (6)
C50.0661 (7)0.0469 (6)0.0645 (7)0.0002 (5)0.0090 (6)0.0013 (5)
C60.0524 (6)0.0413 (5)0.0493 (6)0.0050 (4)0.0014 (4)0.0035 (4)
C70.0727 (8)0.0420 (6)0.0520 (6)0.0020 (5)0.0054 (5)0.0027 (5)
C80.0649 (8)0.0524 (7)0.0868 (10)0.0123 (6)0.0158 (7)0.0174 (7)
C90.0715 (8)0.0472 (6)0.0723 (8)0.0125 (6)0.0130 (6)0.0067 (6)
C100.1019 (12)0.0519 (8)0.1070 (13)0.0087 (8)0.0373 (10)0.0107 (8)
C110.0641 (7)0.0574 (7)0.0560 (7)0.0024 (6)0.0113 (6)0.0091 (6)
C120.0549 (6)0.0490 (6)0.0478 (6)0.0059 (5)0.0082 (5)0.0057 (5)
C130.0748 (8)0.0627 (8)0.0652 (8)0.0149 (7)0.0066 (6)0.0057 (6)
C140.0666 (8)0.0971 (12)0.0833 (10)0.0159 (8)0.0131 (8)0.0295 (9)
C150.0703 (9)0.0791 (11)0.0967 (12)0.0107 (8)0.0120 (8)0.0368 (9)
C160.1131 (14)0.0506 (8)0.0956 (12)0.0019 (8)0.0018 (10)0.0065 (8)
C170.0896 (10)0.0526 (7)0.0687 (8)0.0097 (7)0.0099 (7)0.0036 (6)
Geometric parameters (Å, º) top
O1—C71.2163 (15)C8—H8A1.01 (2)
N1—C71.3823 (16)C8—H8B1.004 (18)
N1—C61.3869 (15)C9—C101.166 (2)
N1—C111.4632 (15)C10—H100.95 (2)
N2—C71.3775 (16)C11—C121.5076 (17)
N2—C11.3875 (15)C11—H11A1.042 (17)
N2—C81.4525 (16)C11—H11B0.995 (18)
C1—C21.3737 (17)C12—C171.3761 (18)
C1—C61.3985 (16)C12—C131.3771 (19)
C2—C31.383 (2)C13—C141.381 (2)
C2—H20.959 (17)C13—H131.008 (19)
C3—C41.384 (2)C14—C151.369 (3)
C3—H30.982 (18)C14—H140.94 (2)
C4—C51.388 (2)C15—C161.366 (3)
C4—H40.983 (17)C15—H150.94 (2)
C5—C61.3793 (17)C16—C171.379 (2)
C5—H50.986 (17)C16—H160.99 (2)
C8—C91.4610 (19)C17—H171.00 (2)
O1···H8B2.492 (18)C5···H11A2.897 (16)
O1···H11B2.607 (16)C5···H10vi2.93 (3)
O1···H132.760 (18)C8···H22.947 (16)
O1···H16i2.568 (18)C10···H8Aii2.874 (18)
C2···C93.5265 (19)C10···H14iii2.95 (2)
C7···C133.5805 (19)C10···H11Avii2.895 (17)
C9···C1ii3.5236 (18)C11···H52.998 (16)
C10···N2ii3.4291 (19)C13···H14v2.964 (17)
C10···C8ii3.385 (2)H3···O1iii2.542 (18)
C10···C14iii3.512 (3)H5···H11A2.46 (2)
C11···C13iv3.495 (2)H11A···H172.38 (2)
C14···C14v3.543 (2)H11B···H132.45 (2)
C4···H10vi2.84 (3)
C7—N1—C6110.18 (9)N2—C8—H8B105.8 (10)
C7—N1—C11123.09 (10)C9—C8—H8B111.9 (11)
C6—N1—C11126.62 (10)H8A—C8—H8B109.7 (15)
C7—N2—C1110.34 (9)C10—C9—C8179.48 (16)
C7—N2—C8123.32 (11)C9—C10—H10178.1 (14)
C1—N2—C8126.34 (11)N1—C11—C12113.05 (10)
C2—C1—N2131.74 (11)N1—C11—H11A107.8 (9)
C2—C1—C6121.46 (11)C12—C11—H11A108.8 (9)
N2—C1—C6106.80 (10)N1—C11—H11B107.1 (10)
C1—C2—C3117.56 (13)C12—C11—H11B108.2 (9)
C1—C2—H2119.0 (10)H11A—C11—H11B112.0 (13)
C3—C2—H2123.4 (10)C17—C12—C13118.52 (13)
C2—C3—C4121.16 (13)C17—C12—C11121.19 (12)
C2—C3—H3120.6 (11)C13—C12—C11120.28 (12)
C4—C3—H3118.2 (11)C12—C13—C14120.50 (15)
C3—C4—C5121.56 (14)C12—C13—H13119.1 (10)
C3—C4—H4119.7 (10)C14—C13—H13120.4 (10)
C5—C4—H4118.6 (10)C15—C14—C13120.41 (16)
C6—C5—C4117.22 (13)C15—C14—H14119.1 (14)
C6—C5—H5120.5 (10)C13—C14—H14120.5 (14)
C4—C5—H5122.3 (10)C16—C15—C14119.46 (16)
C5—C6—N1132.12 (11)C16—C15—H15120.9 (11)
C5—C6—C1121.03 (11)C14—C15—H15119.6 (11)
N1—C6—C1106.85 (10)C15—C16—C17120.33 (16)
O1—C7—N2126.95 (12)C15—C16—H16119.8 (12)
O1—C7—N1127.23 (12)C17—C16—H16119.8 (12)
N2—C7—N1105.82 (10)C12—C17—C16120.78 (15)
N2—C8—C9111.93 (11)C12—C17—H17119.1 (11)
N2—C8—H8A108.6 (11)C16—C17—H17120.1 (11)
C9—C8—H8A108.8 (11)
C7—N2—C1—C2179.03 (13)C1—N2—C7—N11.23 (13)
C8—N2—C1—C20.1 (2)C8—N2—C7—N1179.61 (11)
C7—N2—C1—C60.58 (13)C6—N1—C7—O1178.85 (13)
C8—N2—C1—C6179.71 (11)C11—N1—C7—O12.4 (2)
N2—C1—C2—C3179.26 (12)C6—N1—C7—N21.44 (13)
C6—C1—C2—C30.29 (18)C11—N1—C7—N2177.93 (11)
C1—C2—C3—C40.4 (2)C7—N2—C8—C9107.51 (15)
C2—C3—C4—C50.2 (2)C1—N2—C8—C973.46 (18)
C3—C4—C5—C60.2 (2)C7—N1—C11—C1288.90 (15)
C4—C5—C6—N1179.75 (12)C6—N1—C11—C1287.00 (15)
C4—C5—C6—C10.37 (18)N1—C11—C12—C1799.61 (15)
C7—N1—C6—C5179.00 (12)N1—C11—C12—C1381.60 (15)
C11—N1—C6—C52.7 (2)C17—C12—C13—C140.6 (2)
C7—N1—C6—C11.11 (13)C11—C12—C13—C14179.46 (13)
C11—N1—C6—C1177.44 (11)C12—C13—C14—C150.4 (2)
C2—C1—C6—C50.12 (17)C13—C14—C15—C160.1 (3)
N2—C1—C6—C5179.78 (10)C14—C15—C16—C170.5 (3)
C2—C1—C6—N1179.98 (11)C13—C12—C17—C160.3 (2)
N2—C1—C6—N10.32 (12)C11—C12—C17—C16179.09 (14)
C1—N2—C7—O1179.06 (13)C15—C16—C17—C120.3 (3)
C8—N2—C7—O10.1 (2)
Symmetry codes: (i) x, y+1, z; (ii) x, y+1/2, z+1/2; (iii) x, y+3/2, z1/2; (iv) x+1, y+1, z+1; (v) x, y+1, z+1; (vi) x, y1, z; (vii) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···O1iii0.982 (18)2.542 (18)3.4997 (18)165.1 (14)
C16—H16···O1vi0.994 (18)2.568 (18)3.468 (2)150.6 (14)
C17—H17···Cg2viii1.00 (2)2.831 (18)3.6964 (17)144.6 (15)
Symmetry codes: (iii) x, y+3/2, z1/2; (vi) x, y1, z; (viii) x+1, y1/2, z+1/2.
 

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