organic compounds
Adjacent molecules of the title compound, C19H18ClN3O, are linked by an NO hydrogen bond [2.926 (2) Å] into a zigzag chain.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601467X/xu2034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680601467X/xu2034Isup2.hkl |
CCDC reference: 608537
Computing details top
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
(Z)-4-Benzylidene-1-(4-chlorophenyl)-2-propylamino-1H-imidazol-5(4H)-one top
Crystal data top
C19H18ClN3O | F(000) = 712 |
Mr = 339.81 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3657 reflections |
a = 10.9150 (7) Å | θ = 2.3–22.4° |
b = 12.9335 (8) Å | µ = 0.23 mm−1 |
c = 12.8701 (8) Å | T = 292 K |
β = 103.331 (1)° | Block, yellow |
V = 1767.9 (2) Å3 | 0.2 × 0.2 × 0.2 mm |
Z = 4 |
Data collection top
Bruker SMART APEX area-detector diffractometer | 2612 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
φ and ω scans | h = −13→14 |
16744 measured reflections | k = −16→16 |
4038 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0731P)2] where P = (Fo2 + 2Fc2)/3 |
4038 reflections | (Δ/σ)max = 0.001 |
245 parameters | Δρmax = 0.18 e Å−3 |
6 restraints | Δρmin = −0.23 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.43078 (7) | 0.61254 (4) | 0.62306 (6) | 0.1074 (3) | |
O1 | 0.25522 (14) | 0.22962 (9) | 0.90890 (10) | 0.0717 (4) | |
N1 | 0.27779 (14) | 0.19827 (10) | 0.73745 (10) | 0.0499 (4) | |
N2 | 0.22032 (14) | 0.02937 (10) | 0.71804 (10) | 0.0529 (4) | |
C1 | 0.31669 (17) | 0.29834 (12) | 0.71014 (12) | 0.0501 (4) | |
C2 | 0.42712 (18) | 0.31034 (14) | 0.67649 (14) | 0.0627 (5) | |
C3 | 0.4628 (2) | 0.40693 (15) | 0.64944 (16) | 0.0707 (6) | |
C4 | 0.3883 (2) | 0.49045 (14) | 0.65821 (15) | 0.0670 (5) | |
C5 | 0.2800 (2) | 0.47964 (13) | 0.69330 (15) | 0.0672 (5) | |
C6 | 0.24204 (19) | 0.38243 (12) | 0.71860 (14) | 0.0587 (5) | |
C7 | 0.24914 (16) | 0.17200 (13) | 0.83356 (13) | 0.0515 (4) | |
C8 | 0.21035 (16) | 0.06162 (12) | 0.81865 (12) | 0.0490 (4) | |
C9 | 0.25776 (17) | 0.10995 (11) | 0.67258 (13) | 0.0504 (4) | |
N3 | 0.27496 (18) | 0.11197 (10) | 0.57423 (11) | 0.0679 (6) | |
C10 | 0.2742 (5) | 0.0157 (3) | 0.5131 (3) | 0.0617 (13) | 0.612 (3) |
C11 | 0.3783 (6) | −0.0595 (4) | 0.5588 (4) | 0.0669 (14) | 0.612 (3) |
C12 | 0.3847 (4) | −0.1467 (2) | 0.4812 (3) | 0.0784 (11) | 0.612 (3) |
C10' | 0.2100 (7) | 0.0319 (6) | 0.4949 (5) | 0.073 (2) | 0.388 (3) |
C11' | 0.3107 (6) | −0.0366 (4) | 0.4650 (5) | 0.085 (2) | 0.388 (3) |
C12' | 0.3775 (12) | −0.1016 (7) | 0.5578 (8) | 0.101 (4) | 0.388 (3) |
C13 | 0.16922 (17) | 0.00765 (13) | 0.89299 (13) | 0.0553 (5) | |
C14 | 0.12379 (17) | −0.09906 (13) | 0.88653 (14) | 0.0549 (5) | |
C15 | 0.12365 (19) | −0.16436 (14) | 0.80050 (15) | 0.0653 (5) | |
C16 | 0.0783 (2) | −0.26386 (15) | 0.79929 (18) | 0.0746 (6) | |
C17 | 0.0332 (2) | −0.30097 (17) | 0.8838 (2) | 0.0783 (6) | |
C18 | 0.0319 (2) | −0.23816 (17) | 0.96882 (18) | 0.0803 (6) | |
C19 | 0.07598 (19) | −0.13815 (16) | 0.97019 (15) | 0.0701 (6) | |
H2 | 0.4774 | 0.2532 | 0.6721 | 0.075* | |
H3 | 0.5363 | 0.4155 | 0.6256 | 0.085* | |
H5 | 0.2318 | 0.5374 | 0.7002 | 0.081* | |
H6 | 0.1674 | 0.3741 | 0.7409 | 0.070* | |
H3n | 0.2867 | 0.1702 | 0.5457 | 0.081* | 0.612 (3) |
H10a | 0.2800 | 0.0334 | 0.4411 | 0.074* | 0.612 (3) |
H10b | 0.1941 | −0.0187 | 0.5081 | 0.074* | 0.612 (3) |
H11a | 0.3641 | −0.0882 | 0.6247 | 0.080* | 0.612 (3) |
H11b | 0.4581 | −0.0231 | 0.5755 | 0.080* | 0.612 (3) |
H12a | 0.4507 | −0.1938 | 0.5132 | 0.118* | 0.612 (3) |
H12b | 0.4019 | −0.1187 | 0.4170 | 0.118* | 0.612 (3) |
H12c | 0.3058 | −0.1828 | 0.4645 | 0.118* | 0.612 (3) |
H3n' | 0.3224 | 0.1582 | 0.5557 | 0.081* | 0.388 (3) |
H10c | 0.1606 | 0.0655 | 0.4317 | 0.087* | 0.388 (3) |
H10d | 0.1540 | −0.0098 | 0.5262 | 0.087* | 0.388 (3) |
H11c | 0.2716 | −0.0815 | 0.4063 | 0.102* | 0.388 (3) |
H11d | 0.3716 | 0.0065 | 0.4412 | 0.102* | 0.388 (3) |
H12d | 0.4458 | −0.1379 | 0.5388 | 0.151* | 0.388 (3) |
H12e | 0.3195 | −0.1506 | 0.5757 | 0.151* | 0.388 (3) |
H12f | 0.4097 | −0.0579 | 0.6182 | 0.151* | 0.388 (3) |
H13 | 0.1697 | 0.0424 | 0.9564 | 0.066* | |
H15 | 0.1545 | −0.1406 | 0.7433 | 0.078* | |
H16 | 0.0780 | −0.3064 | 0.7410 | 0.089* | |
H17 | 0.0039 | −0.3685 | 0.8829 | 0.094* | |
H18 | 0.0013 | −0.2629 | 1.0258 | 0.096* | |
H19 | 0.0738 | −0.0958 | 1.0282 | 0.084* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1282 (6) | 0.0640 (4) | 0.1156 (5) | −0.0377 (3) | −0.0014 (4) | 0.0183 (3) |
O1 | 0.1073 (12) | 0.0613 (8) | 0.0493 (7) | −0.0058 (7) | 0.0240 (7) | −0.0138 (6) |
N1 | 0.0666 (10) | 0.0408 (7) | 0.0428 (7) | −0.0013 (6) | 0.0136 (7) | −0.0012 (6) |
N2 | 0.0750 (10) | 0.0430 (7) | 0.0435 (8) | 0.0001 (7) | 0.0199 (7) | 0.0022 (6) |
C1 | 0.0640 (12) | 0.0431 (9) | 0.0408 (8) | −0.0034 (8) | 0.0069 (8) | −0.0014 (7) |
C2 | 0.0693 (13) | 0.0545 (11) | 0.0653 (12) | −0.0015 (9) | 0.0173 (10) | −0.0002 (9) |
C3 | 0.0727 (14) | 0.0690 (13) | 0.0701 (13) | −0.0183 (11) | 0.0159 (11) | 0.0025 (10) |
C4 | 0.0834 (15) | 0.0510 (11) | 0.0574 (11) | −0.0184 (10) | −0.0027 (10) | 0.0030 (8) |
C5 | 0.0864 (15) | 0.0457 (10) | 0.0625 (11) | 0.0035 (10) | 0.0029 (11) | −0.0008 (8) |
C6 | 0.0690 (13) | 0.0492 (10) | 0.0562 (11) | 0.0042 (8) | 0.0113 (9) | −0.0003 (8) |
C7 | 0.0626 (12) | 0.0509 (9) | 0.0414 (9) | 0.0038 (8) | 0.0128 (8) | −0.0009 (7) |
C8 | 0.0587 (11) | 0.0477 (9) | 0.0408 (8) | 0.0047 (8) | 0.0122 (8) | 0.0017 (7) |
C9 | 0.0678 (12) | 0.0412 (9) | 0.0437 (9) | 0.0035 (8) | 0.0157 (8) | 0.0010 (7) |
N3 | 0.1202 (16) | 0.0446 (8) | 0.0461 (9) | −0.0110 (8) | 0.0340 (9) | −0.0010 (6) |
C10 | 0.096 (4) | 0.046 (2) | 0.050 (2) | 0.007 (2) | 0.031 (2) | −0.0026 (17) |
C11 | 0.082 (3) | 0.059 (3) | 0.066 (3) | 0.004 (2) | 0.031 (2) | −0.008 (2) |
C12 | 0.091 (3) | 0.0538 (19) | 0.097 (3) | 0.0013 (17) | 0.036 (2) | −0.0169 (19) |
C10' | 0.118 (7) | 0.050 (4) | 0.057 (4) | −0.005 (4) | 0.034 (4) | −0.007 (3) |
C11' | 0.122 (6) | 0.075 (4) | 0.068 (4) | −0.022 (4) | 0.042 (4) | −0.016 (3) |
C12' | 0.131 (8) | 0.073 (7) | 0.097 (7) | 0.014 (6) | 0.022 (5) | −0.001 (6) |
C13 | 0.0656 (12) | 0.0595 (10) | 0.0425 (9) | 0.0026 (9) | 0.0157 (8) | 0.0009 (8) |
C14 | 0.0546 (11) | 0.0591 (11) | 0.0497 (10) | 0.0013 (8) | 0.0096 (8) | 0.0101 (8) |
C15 | 0.0798 (14) | 0.0562 (11) | 0.0638 (12) | 0.0016 (10) | 0.0246 (10) | 0.0074 (9) |
C16 | 0.0832 (16) | 0.0569 (12) | 0.0818 (14) | 0.0013 (10) | 0.0154 (12) | 0.0035 (10) |
C17 | 0.0647 (14) | 0.0647 (13) | 0.0973 (16) | −0.0073 (10) | 0.0019 (12) | 0.0229 (12) |
C18 | 0.0788 (16) | 0.0881 (16) | 0.0725 (14) | −0.0181 (12) | 0.0141 (12) | 0.0260 (12) |
C19 | 0.0714 (14) | 0.0843 (14) | 0.0549 (11) | −0.0126 (11) | 0.0152 (10) | 0.0106 (10) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.735 (2) | C18—C19 | 1.379 (3) |
O1—C7 | 1.213 (2) | C2—H2 | 0.93 |
N1—C7 | 1.386 (2) | C3—H3 | 0.93 |
N1—C9 | 1.402 (2) | C5—H5 | 0.93 |
N1—C1 | 1.431 (2) | C6—H6 | 0.93 |
N2—C9 | 1.306 (2) | N3—H3n | 0.86 |
N2—C8 | 1.388 (2) | C10—H10a | 0.97 |
C1—C6 | 1.378 (2) | C10—H10b | 0.97 |
C1—C2 | 1.380 (2) | C11—H11a | 0.97 |
C2—C3 | 1.377 (2) | C11—H11b | 0.97 |
C3—C4 | 1.372 (3) | C12—H12a | 0.96 |
C4—C5 | 1.366 (3) | C12—H12b | 0.96 |
C5—C6 | 1.386 (2) | C12—H12c | 0.96 |
C7—C8 | 1.489 (2) | C10'—H10c | 0.97 |
C8—C13 | 1.342 (2) | C10'—H10d | 0.97 |
C9—N3 | 1.322 (2) | C11'—H11c | 0.97 |
N3—C10 | 1.472 (4) | C11'—H11d | 0.97 |
C10—C11 | 1.508 (6) | C12'—H12d | 0.96 |
C11—C12 | 1.519 (5) | C12'—H12e | 0.96 |
C10'—C11' | 1.528 (7) | C12'—H12f | 0.96 |
C11'—C12' | 1.504 (8) | C13—H13 | 0.93 |
C13—C14 | 1.462 (2) | C15—H15 | 0.93 |
C14—C15 | 1.392 (3) | C16—H16 | 0.93 |
C14—C19 | 1.395 (2) | C17—H17 | 0.93 |
C15—C16 | 1.378 (2) | C18—H18 | 0.93 |
C16—C17 | 1.379 (3) | C19—H19 | 0.93 |
C17—C18 | 1.366 (3) | ||
C7—N1—C9 | 107.2 (1) | C9—N3—H3n | 119.6 |
C7—N1—C1 | 125.6 (1) | C10—N3—H3n | 119.6 |
C9—N1—C1 | 127.2 (1) | N3—C10—H10a | 108.5 |
C9—N2—C8 | 106.1 (1) | C11—C10—H10a | 108.5 |
C6—C1—C2 | 120.7 (2) | N3—C10—H10b | 108.5 |
C6—C1—N1 | 118.7 (2) | C11—C10—H10b | 108.5 |
C2—C1—N1 | 120.6 (2) | H10a—C10—H10b | 107.5 |
C3—C2—C1 | 120.0 (2) | C10—C11—H11a | 109.3 |
C4—C3—C2 | 119.1 (2) | C12—C11—H11a | 109.3 |
C5—C4—C3 | 121.4 (2) | C10—C11—H11b | 109.3 |
C5—C4—Cl1 | 118.9 (2) | C12—C11—H11b | 109.3 |
C3—C4—Cl1 | 119.7 (2) | H11a—C11—H11b | 108.0 |
C4—C5—C6 | 119.9 (2) | C11—C12—H12a | 109.5 |
C1—C6—C5 | 118.9 (2) | C11—C12—H12b | 109.5 |
O1—C7—N1 | 125.5 (2) | H12a—C12—H12b | 109.5 |
O1—C7—C8 | 130.8 (2) | C11—C12—H12c | 109.5 |
N1—C7—C8 | 103.7 (1) | H12a—C12—H12c | 109.5 |
C13—C8—N2 | 128.3 (2) | H12b—C12—H12c | 109.5 |
C13—C8—C7 | 122.6 (1) | C11'—C10'—H10c | 110.0 |
N2—C8—C7 | 109.1 (1) | C11'—C10'—H10d | 110.0 |
N2—C9—N3 | 125.0 (2) | H10c—C10'—H10d | 108.4 |
N2—C9—N1 | 113.9 (1) | C12'—C11'—H11c | 109.3 |
N3—C9—N1 | 121.1 (1) | C10'—C11'—H11c | 109.3 |
C9—N3—C10 | 120.7 (2) | C12'—C11'—H11d | 109.3 |
N3—C10—C11 | 115.2 (4) | C10'—C11'—H11d | 109.3 |
C10—C11—C12 | 111.6 (4) | H11c—C11'—H11d | 108.0 |
C12'—C11'—C10' | 111.6 (6) | C11'—C12'—H12d | 109.5 |
C8—C13—C14 | 127.9 (2) | C11'—C12'—H12e | 109.5 |
C15—C14—C19 | 117.5 (2) | H12d—C12'—H12e | 109.5 |
C15—C14—C13 | 123.8 (2) | C11'—C12'—H12f | 109.5 |
C19—C14—C13 | 118.7 (2) | H12d—C12'—H12f | 109.5 |
C16—C15—C14 | 120.7 (2) | H12e—C12'—H12f | 109.5 |
C15—C16—C17 | 120.6 (2) | C8—C13—H13 | 116.0 |
C18—C17—C16 | 119.8 (2) | C14—C13—H13 | 116.0 |
C17—C18—C19 | 120.0 (2) | C16—C15—H15 | 119.7 |
C18—C19—C14 | 121.4 (2) | C14—C15—H15 | 119.7 |
C3—C2—H2 | 120.0 | C15—C16—H16 | 119.7 |
C1—C2—H2 | 120.0 | C17—C16—H16 | 119.7 |
C4—C3—H3 | 120.5 | C18—C17—H17 | 120.1 |
C2—C3—H3 | 120.5 | C16—C17—H17 | 120.1 |
C4—C5—H5 | 120.0 | C17—C18—H18 | 120.0 |
C6—C5—H5 | 120.0 | C19—C18—H18 | 120.0 |
C1—C6—H6 | 120.6 | C18—C19—H19 | 119.3 |
C5—C6—H6 | 120.6 | C14—C19—H19 | 119.3 |
C7—N1—C1—C6 | −54.4 (2) | N1—C7—C8—N2 | 1.1 (2) |
C9—N1—C1—C6 | 123.5 (2) | C8—N2—C9—N3 | −177.9 (2) |
C7—N1—C1—C2 | 125.3 (2) | C8—N2—C9—N1 | 1.3 (2) |
C9—N1—C1—C2 | −56.8 (3) | C7—N1—C9—N2 | −0.7 (2) |
C6—C1—C2—C3 | −1.0 (3) | C1—N1—C9—N2 | −178.9 (2) |
N1—C1—C2—C3 | 179.4 (2) | C7—N1—C9—N3 | 178.6 (2) |
C1—C2—C3—C4 | 1.1 (3) | C1—N1—C9—N3 | 0.4 (3) |
C2—C3—C4—C5 | 0.1 (3) | N2—C9—N3—C10 | −11.0 (4) |
C2—C3—C4—Cl1 | −179.3 (2) | N1—C9—N3—C10 | 169.8 (3) |
C3—C4—C5—C6 | −1.5 (3) | C9—N3—C10—C11 | −63.8 (5) |
Cl1—C4—C5—C6 | 178.0 (1) | N3—C10—C11—C12 | −169.7 (4) |
C2—C1—C6—C5 | −0.4 (3) | N2—C8—C13—C14 | −0.3 (3) |
N1—C1—C6—C5 | 179.3 (2) | C7—C8—C13—C14 | 177.3 (2) |
C4—C5—C6—C1 | 1.6 (3) | C8—C13—C14—C15 | 4.0 (3) |
C9—N1—C7—O1 | −179.7 (2) | C8—C13—C14—C19 | −175.1 (2) |
C1—N1—C7—O1 | −1.5 (3) | C19—C14—C15—C16 | −0.3 (3) |
C9—N1—C7—C8 | −0.3 (2) | C13—C14—C15—C16 | −179.4 (2) |
C1—N1—C7—C8 | 178.0 (2) | C14—C15—C16—C17 | −0.6 (3) |
C9—N2—C8—C13 | 176.4 (2) | C15—C16—C17—C18 | 0.9 (3) |
C9—N2—C8—C7 | −1.5 (2) | C16—C17—C18—C19 | −0.3 (3) |
O1—C7—C8—C13 | 2.5 (3) | C17—C18—C19—C14 | −0.7 (3) |
N1—C7—C8—C13 | −176.9 (2) | C15—C14—C19—C18 | 1.0 (3) |
O1—C7—C8—N2 | −179.5 (2) | C13—C14—C19—C18 | −179.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3n···O1i | 0.86 | 2.15 | 2.926 (2) | 150 |
N3—H3n′···O1i | 0.86 | 2.36 | 2.926 (2) | 124 |
Symmetry code: (i) x, −y+1/2, z−1/2. |