Experimental
Crystal data
C14H10N2O Mr = 222.24 Orthorhombic, P n a 21 a = 20.1647 (4) Å b = 5.0223 (1) Å c = 21.8791 (5) Å V = 2215.77 (8) Å3 Z = 8 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.3 × 0.3 × 0.3 mm
|
Data collection
Bruker APEXII diffractometer 15055 measured reflections 2619 independent reflections 2042 reflections with I > 2σ(I) Rint = 0.030
|
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | N1—H1⋯N4i | 0.86 (3) | 2.11 (2) | 2.940 (3) | 161 (3) | N3—H3⋯N2 | 0.86 (3) | 2.28 (3) | 3.111 (3) | 164 (3) | Symmetry code: (i) . | |
Data collection: APEX2 (Bruker, 2005
); cell refinement: SAINT (Bruker, 2005
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: X-SEED (Barbour, 2001
); software used to prepare material for publication: publCIF (Westrip, 2010
).
Supporting information
The compound was synthesized from the reaction of isatin and aniline in ethanol according to a literature method (Grimshaw & Begley, 1974), and crystals were obtained by recrystallization from ethanol.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino H-atoms were located in a difference Fourier map, and were refined isotropically with a distance restraint of N–H 0.86±0.01 Å. Friedel pairs were merged.
Structure description
top For the synthesis, see: Grimshaw & Begley (1974). For the crystal structures of other phenyl-substituted derivatives, see: Akkurt et al. (2003); Hökelek et al. (2006); Öztürk et al. (2003).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
3-(Phenylimino)indolin-2-one
top Crystal data top C14H10N2O | F(000) = 928 |
Mr = 222.24 | Dx = 1.332 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3521 reflections |
a = 20.1647 (4) Å | θ = 2.7–25.7° |
b = 5.0223 (1) Å | µ = 0.09 mm−1 |
c = 21.8791 (5) Å | T = 293 K |
V = 2215.77 (8) Å3 | Block, orange |
Z = 8 | 0.3 × 0.3 × 0.3 mm |
Data collection top Bruker APEXII diffractometer | 2042 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
φ and ω scans | h = −24→26 |
15055 measured reflections | k = −3→6 |
2619 independent reflections | l = −28→28 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0745P)2 + 0.0171P] where P = (Fo2 + 2Fc2)/3 |
2619 reflections | (Δ/σ)max = 0.001 |
315 parameters | Δρmax = 0.19 e Å−3 |
3 restraints | Δρmin = −0.20 e Å−3 |
Crystal data top C14H10N2O | V = 2215.77 (8) Å3 |
Mr = 222.24 | Z = 8 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 20.1647 (4) Å | µ = 0.09 mm−1 |
b = 5.0223 (1) Å | T = 293 K |
c = 21.8791 (5) Å | 0.3 × 0.3 × 0.3 mm |
Data collection top Bruker APEXII diffractometer | 2042 reflections with I > 2σ(I) |
15055 measured reflections | Rint = 0.030 |
2619 independent reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.034 | 3 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.19 e Å−3 |
2619 reflections | Δρmin = −0.20 e Å−3 |
315 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.36628 (12) | 0.9072 (6) | 0.49888 (10) | 0.0769 (7) | |
O2 | 0.11993 (12) | 0.6636 (6) | 0.52675 (12) | 0.0816 (8) | |
N1 | 0.44843 (11) | 0.6264 (6) | 0.53285 (11) | 0.0543 (6) | |
N2 | 0.28865 (11) | 0.6607 (5) | 0.59271 (10) | 0.0505 (6) | |
N3 | 0.20427 (11) | 0.9352 (5) | 0.49173 (10) | 0.0535 (6) | |
N4 | 0.04413 (11) | 0.9133 (5) | 0.43186 (11) | 0.0525 (6) | |
C1 | 0.38742 (14) | 0.7371 (6) | 0.53269 (13) | 0.0535 (7) | |
C2 | 0.34907 (12) | 0.5996 (5) | 0.58405 (11) | 0.0462 (6) | |
C3 | 0.39537 (12) | 0.4079 (5) | 0.61115 (11) | 0.0446 (6) | |
C4 | 0.39058 (14) | 0.2185 (6) | 0.65685 (13) | 0.0519 (7) | |
H4 | 0.3517 | 0.2014 | 0.6794 | 0.062* | |
C5 | 0.44415 (16) | 0.0553 (6) | 0.66857 (15) | 0.0605 (7) | |
H5 | 0.4414 | −0.0724 | 0.6993 | 0.073* | |
C6 | 0.50158 (16) | 0.0802 (7) | 0.63515 (17) | 0.0663 (8) | |
H6 | 0.5370 | −0.0327 | 0.6436 | 0.080* | |
C7 | 0.50835 (15) | 0.2678 (7) | 0.58932 (15) | 0.0609 (8) | |
H7 | 0.5475 | 0.2840 | 0.5672 | 0.073* | |
C8 | 0.45450 (13) | 0.4302 (6) | 0.57769 (12) | 0.0481 (6) | |
C9 | 0.25376 (12) | 0.5309 (5) | 0.64115 (12) | 0.0454 (6) | |
C10 | 0.20928 (13) | 0.3331 (7) | 0.62764 (14) | 0.0565 (7) | |
H10 | 0.2017 | 0.2850 | 0.5872 | 0.068* | |
C11 | 0.17563 (15) | 0.2051 (7) | 0.67433 (17) | 0.0619 (8) | |
H11 | 0.1464 | 0.0673 | 0.6653 | 0.074* | |
C12 | 0.18528 (14) | 0.2810 (7) | 0.73385 (15) | 0.0594 (8) | |
H12 | 0.1628 | 0.1938 | 0.7651 | 0.071* | |
C13 | 0.22774 (15) | 0.4843 (6) | 0.74728 (13) | 0.0565 (7) | |
H13 | 0.2334 | 0.5381 | 0.7876 | 0.068* | |
C14 | 0.26251 (16) | 0.6108 (6) | 0.70102 (13) | 0.0536 (7) | |
H14 | 0.2916 | 0.7488 | 0.7102 | 0.064* | |
C15 | 0.14226 (13) | 0.8292 (7) | 0.49218 (13) | 0.0539 (7) | |
C16 | 0.10494 (12) | 0.9666 (5) | 0.44047 (11) | 0.0455 (6) | |
C17 | 0.15210 (13) | 1.1524 (5) | 0.41286 (11) | 0.0437 (6) | |
C18 | 0.14711 (14) | 1.3414 (6) | 0.36677 (13) | 0.0528 (7) | |
H18 | 0.1080 | 1.3596 | 0.3447 | 0.063* | |
C19 | 0.20099 (16) | 1.5019 (6) | 0.35414 (15) | 0.0609 (7) | |
H19 | 0.1983 | 1.6295 | 0.3235 | 0.073* | |
C20 | 0.25942 (17) | 1.4720 (7) | 0.38751 (17) | 0.0661 (8) | |
H20 | 0.2955 | 1.5803 | 0.3785 | 0.079* | |
C21 | 0.26500 (16) | 1.2858 (7) | 0.43355 (16) | 0.0620 (8) | |
H21 | 0.3042 | 1.2679 | 0.4555 | 0.074* | |
C22 | 0.21093 (13) | 1.1269 (5) | 0.44624 (12) | 0.0472 (6) | |
C23 | 0.00927 (12) | 1.0342 (6) | 0.38269 (12) | 0.0461 (6) | |
C24 | 0.01763 (15) | 0.9423 (6) | 0.32334 (14) | 0.0576 (7) | |
H24 | 0.0478 | 0.8065 | 0.3154 | 0.069* | |
C25 | −0.01848 (16) | 1.0510 (7) | 0.27619 (16) | 0.0610 (8) | |
H25 | −0.0126 | 0.9887 | 0.2365 | 0.073* | |
C26 | −0.06293 (15) | 1.2504 (7) | 0.28746 (16) | 0.0630 (8) | |
H26 | −0.0869 | 1.3255 | 0.2555 | 0.076* | |
C27 | −0.07213 (15) | 1.3401 (7) | 0.34652 (17) | 0.0687 (9) | |
H27 | −0.1025 | 1.4755 | 0.3541 | 0.082* | |
C28 | −0.03689 (14) | 1.2315 (7) | 0.39430 (14) | 0.0586 (7) | |
H28 | −0.0441 | 1.2903 | 0.4341 | 0.070* | |
H1 | 0.4791 (10) | 0.653 (6) | 0.5061 (10) | 0.052 (8)* | |
H3 | 0.2338 (12) | 0.883 (7) | 0.5172 (12) | 0.064 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0687 (14) | 0.0941 (18) | 0.0678 (15) | 0.0084 (12) | 0.0068 (11) | 0.0340 (13) |
O2 | 0.0684 (14) | 0.104 (2) | 0.0721 (14) | −0.0040 (13) | −0.0001 (12) | 0.0422 (15) |
N1 | 0.0457 (13) | 0.0711 (16) | 0.0461 (12) | −0.0002 (11) | 0.0104 (10) | 0.0017 (12) |
N2 | 0.0423 (12) | 0.0625 (15) | 0.0468 (12) | 0.0047 (10) | 0.0007 (9) | 0.0070 (11) |
N3 | 0.0483 (12) | 0.0653 (15) | 0.0470 (12) | 0.0081 (11) | −0.0064 (10) | 0.0028 (11) |
N4 | 0.0419 (12) | 0.0659 (15) | 0.0498 (12) | 0.0040 (11) | 0.0037 (9) | 0.0097 (11) |
C1 | 0.0477 (15) | 0.0673 (19) | 0.0454 (15) | −0.0002 (13) | 0.0020 (12) | 0.0021 (14) |
C2 | 0.0440 (13) | 0.0533 (15) | 0.0414 (12) | −0.0015 (11) | −0.0017 (10) | −0.0023 (12) |
C3 | 0.0424 (13) | 0.0466 (14) | 0.0447 (13) | 0.0000 (11) | −0.0018 (10) | −0.0070 (11) |
C4 | 0.0528 (15) | 0.0507 (15) | 0.0523 (16) | −0.0015 (12) | −0.0007 (12) | −0.0013 (13) |
C5 | 0.0673 (18) | 0.0514 (16) | 0.0628 (17) | 0.0045 (14) | −0.0089 (15) | 0.0015 (14) |
C6 | 0.0586 (17) | 0.0610 (18) | 0.079 (2) | 0.0137 (15) | −0.0129 (15) | −0.0068 (17) |
C7 | 0.0498 (16) | 0.0683 (19) | 0.0645 (19) | 0.0081 (13) | 0.0051 (14) | −0.0094 (16) |
C8 | 0.0452 (14) | 0.0521 (15) | 0.0471 (13) | 0.0008 (11) | 0.0006 (11) | −0.0098 (12) |
C9 | 0.0355 (12) | 0.0527 (15) | 0.0479 (13) | 0.0082 (11) | 0.0022 (10) | 0.0033 (12) |
C10 | 0.0534 (16) | 0.0620 (18) | 0.0541 (16) | −0.0013 (14) | −0.0060 (14) | −0.0022 (14) |
C11 | 0.0501 (16) | 0.0592 (17) | 0.076 (2) | −0.0087 (14) | −0.0041 (15) | 0.0083 (16) |
C12 | 0.0505 (17) | 0.0612 (18) | 0.067 (2) | 0.0046 (14) | 0.0100 (14) | 0.0159 (15) |
C13 | 0.0664 (17) | 0.0566 (16) | 0.0465 (14) | 0.0090 (14) | 0.0075 (13) | −0.0021 (13) |
C14 | 0.0539 (16) | 0.0525 (16) | 0.0544 (16) | −0.0026 (13) | 0.0024 (12) | −0.0016 (12) |
C15 | 0.0486 (15) | 0.0687 (19) | 0.0444 (15) | 0.0099 (14) | 0.0045 (12) | 0.0066 (13) |
C16 | 0.0411 (13) | 0.0532 (15) | 0.0422 (13) | 0.0076 (11) | 0.0045 (10) | 0.0025 (11) |
C17 | 0.0444 (14) | 0.0452 (14) | 0.0414 (13) | 0.0083 (11) | 0.0055 (10) | −0.0025 (10) |
C18 | 0.0525 (16) | 0.0513 (15) | 0.0545 (17) | 0.0073 (12) | 0.0051 (13) | 0.0036 (13) |
C19 | 0.0660 (18) | 0.0527 (16) | 0.0640 (17) | 0.0002 (14) | 0.0109 (15) | 0.0083 (15) |
C20 | 0.0609 (17) | 0.0572 (18) | 0.080 (2) | −0.0122 (15) | 0.0092 (17) | −0.0001 (17) |
C21 | 0.0492 (16) | 0.0621 (18) | 0.075 (2) | −0.0016 (13) | −0.0026 (15) | −0.0090 (17) |
C22 | 0.0468 (14) | 0.0480 (14) | 0.0467 (13) | 0.0062 (11) | 0.0026 (11) | −0.0062 (12) |
C23 | 0.0355 (12) | 0.0510 (15) | 0.0519 (14) | 0.0011 (11) | 0.0023 (10) | 0.0069 (12) |
C24 | 0.0606 (17) | 0.0549 (17) | 0.0572 (16) | 0.0146 (13) | 0.0025 (14) | 0.0000 (14) |
C25 | 0.0688 (19) | 0.0606 (18) | 0.0536 (15) | 0.0011 (15) | −0.0094 (14) | −0.0036 (15) |
C26 | 0.0542 (18) | 0.0700 (19) | 0.065 (2) | 0.0061 (15) | −0.0105 (14) | 0.0155 (16) |
C27 | 0.0550 (18) | 0.069 (2) | 0.082 (2) | 0.0236 (15) | 0.0052 (16) | 0.0144 (18) |
C28 | 0.0542 (16) | 0.0647 (19) | 0.0569 (17) | 0.0108 (14) | 0.0077 (14) | 0.0011 (14) |
Geometric parameters (Å, º) top O1—C1 | 1.208 (4) | C11—H11 | 0.9300 |
O2—C15 | 1.211 (4) | C12—C13 | 1.364 (5) |
N1—C1 | 1.350 (4) | C12—H12 | 0.9300 |
N1—C8 | 1.396 (4) | C13—C14 | 1.386 (4) |
N1—H1 | 0.86 (1) | C13—H13 | 0.9300 |
N2—C2 | 1.271 (3) | C14—H14 | 0.9300 |
N2—C9 | 1.429 (3) | C15—C16 | 1.524 (4) |
N3—C15 | 1.359 (4) | C16—C17 | 1.463 (4) |
N3—C22 | 1.391 (4) | C17—C18 | 1.389 (4) |
N3—H3 | 0.86 (1) | C17—C22 | 1.399 (4) |
N4—C16 | 1.269 (3) | C18—C19 | 1.381 (4) |
N4—C23 | 1.421 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.529 (4) | C19—C20 | 1.394 (5) |
C2—C3 | 1.466 (4) | C19—H19 | 0.9300 |
C3—C4 | 1.383 (4) | C20—C21 | 1.379 (5) |
C3—C8 | 1.404 (4) | C20—H20 | 0.9300 |
C4—C5 | 1.380 (4) | C21—C22 | 1.380 (4) |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.375 (5) | C23—C28 | 1.383 (4) |
C5—H5 | 0.9300 | C23—C24 | 1.389 (4) |
C6—C7 | 1.383 (5) | C24—C25 | 1.376 (4) |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—C8 | 1.382 (4) | C25—C26 | 1.366 (4) |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C9—C10 | 1.371 (4) | C26—C27 | 1.381 (5) |
C9—C14 | 1.381 (4) | C26—H26 | 0.9300 |
C10—C11 | 1.385 (4) | C27—C28 | 1.377 (4) |
C10—H10 | 0.9300 | C27—H27 | 0.9300 |
C11—C12 | 1.371 (5) | C28—H28 | 0.9300 |
| | | |
C1—N1—C8 | 111.9 (2) | C14—C13—H13 | 119.9 |
C1—N1—H1 | 126 (2) | C9—C14—C13 | 119.7 (3) |
C8—N1—H1 | 121 (2) | C9—C14—H14 | 120.2 |
C2—N2—C9 | 118.2 (2) | C13—C14—H14 | 120.2 |
C15—N3—C22 | 111.4 (2) | O2—C15—N3 | 128.0 (3) |
C15—N3—H3 | 121 (2) | O2—C15—C16 | 126.2 (3) |
C22—N3—H3 | 128 (2) | N3—C15—C16 | 105.7 (2) |
C16—N4—C23 | 120.0 (2) | N4—C16—C17 | 134.5 (2) |
O1—C1—N1 | 127.9 (3) | N4—C16—C15 | 119.4 (2) |
O1—C1—C2 | 126.2 (3) | C17—C16—C15 | 105.9 (2) |
N1—C1—C2 | 105.8 (2) | C18—C17—C22 | 120.2 (3) |
N2—C2—C3 | 135.1 (3) | C18—C17—C16 | 133.5 (3) |
N2—C2—C1 | 119.0 (2) | C22—C17—C16 | 106.1 (2) |
C3—C2—C1 | 105.8 (2) | C19—C18—C17 | 119.2 (3) |
C4—C3—C8 | 119.4 (3) | C19—C18—H18 | 120.4 |
C4—C3—C2 | 134.4 (2) | C17—C18—H18 | 120.4 |
C8—C3—C2 | 106.1 (2) | C18—C19—C20 | 119.8 (3) |
C5—C4—C3 | 119.2 (3) | C18—C19—H19 | 120.1 |
C5—C4—H4 | 120.4 | C20—C19—H19 | 120.1 |
C3—C4—H4 | 120.4 | C21—C20—C19 | 121.6 (3) |
C6—C5—C4 | 120.4 (3) | C21—C20—H20 | 119.2 |
C6—C5—H5 | 119.8 | C19—C20—H20 | 119.2 |
C4—C5—H5 | 119.8 | C20—C21—C22 | 118.3 (3) |
C5—C6—C7 | 122.0 (3) | C20—C21—H21 | 120.8 |
C5—C6—H6 | 119.0 | C22—C21—H21 | 120.8 |
C7—C6—H6 | 119.0 | C21—C22—N3 | 128.4 (3) |
C8—C7—C6 | 117.3 (3) | C21—C22—C17 | 120.8 (3) |
C8—C7—H7 | 121.4 | N3—C22—C17 | 110.8 (2) |
C6—C7—H7 | 121.4 | C28—C23—C24 | 119.5 (3) |
C7—C8—N1 | 128.0 (3) | C28—C23—N4 | 120.0 (3) |
C7—C8—C3 | 121.6 (3) | C24—C23—N4 | 120.4 (3) |
N1—C8—C3 | 110.4 (2) | C25—C24—C23 | 120.3 (3) |
C10—C9—C14 | 119.9 (3) | C25—C24—H24 | 119.8 |
C10—C9—N2 | 119.5 (3) | C23—C24—H24 | 119.8 |
C14—C9—N2 | 120.5 (3) | C26—C25—C24 | 120.2 (3) |
C9—C10—C11 | 119.9 (3) | C26—C25—H25 | 119.9 |
C9—C10—H10 | 120.1 | C24—C25—H25 | 119.9 |
C11—C10—H10 | 120.1 | C25—C26—C27 | 119.7 (3) |
C12—C11—C10 | 120.1 (3) | C25—C26—H26 | 120.1 |
C12—C11—H11 | 119.9 | C27—C26—H26 | 120.1 |
C10—C11—H11 | 119.9 | C28—C27—C26 | 120.8 (3) |
C13—C12—C11 | 120.1 (3) | C28—C27—H27 | 119.6 |
C13—C12—H12 | 119.9 | C26—C27—H27 | 119.6 |
C11—C12—H12 | 119.9 | C27—C28—C23 | 119.5 (3) |
C12—C13—C14 | 120.2 (3) | C27—C28—H28 | 120.3 |
C12—C13—H13 | 119.9 | C23—C28—H28 | 120.3 |
| | | |
C8—N1—C1—O1 | −178.4 (3) | C22—N3—C15—O2 | −178.1 (3) |
C8—N1—C1—C2 | 0.7 (3) | C22—N3—C15—C16 | 0.7 (3) |
C9—N2—C2—C3 | 3.4 (5) | C23—N4—C16—C17 | 5.7 (5) |
C9—N2—C2—C1 | −179.7 (2) | C23—N4—C16—C15 | −178.2 (2) |
O1—C1—C2—N2 | 1.5 (5) | O2—C15—C16—N4 | 1.7 (5) |
N1—C1—C2—N2 | −177.6 (3) | N3—C15—C16—N4 | −177.1 (3) |
O1—C1—C2—C3 | 179.3 (3) | O2—C15—C16—C17 | 178.9 (3) |
N1—C1—C2—C3 | 0.1 (3) | N3—C15—C16—C17 | 0.1 (3) |
N2—C2—C3—C4 | 0.2 (6) | N4—C16—C17—C18 | 0.4 (5) |
C1—C2—C3—C4 | −177.1 (3) | C15—C16—C17—C18 | −176.1 (3) |
N2—C2—C3—C8 | 176.3 (3) | N4—C16—C17—C22 | 175.8 (3) |
C1—C2—C3—C8 | −0.9 (3) | C15—C16—C17—C22 | −0.8 (3) |
C8—C3—C4—C5 | 0.0 (4) | C22—C17—C18—C19 | 0.4 (4) |
C2—C3—C4—C5 | 175.7 (3) | C16—C17—C18—C19 | 175.2 (3) |
C3—C4—C5—C6 | −0.1 (4) | C17—C18—C19—C20 | 0.1 (4) |
C4—C5—C6—C7 | 0.4 (5) | C18—C19—C20—C21 | −0.4 (5) |
C5—C6—C7—C8 | −0.6 (5) | C19—C20—C21—C22 | 0.0 (5) |
C6—C7—C8—N1 | −177.6 (3) | C20—C21—C22—N3 | −177.2 (3) |
C6—C7—C8—C3 | 0.4 (4) | C20—C21—C22—C17 | 0.6 (4) |
C1—N1—C8—C7 | 176.8 (3) | C15—N3—C22—C21 | 176.7 (3) |
C1—N1—C8—C3 | −1.4 (3) | C15—N3—C22—C17 | −1.2 (3) |
C4—C3—C8—C7 | −0.1 (4) | C18—C17—C22—C21 | −0.8 (4) |
C2—C3—C8—C7 | −177.0 (3) | C16—C17—C22—C21 | −176.9 (2) |
C4—C3—C8—N1 | 178.2 (2) | C18—C17—C22—N3 | 177.3 (2) |
C2—C3—C8—N1 | 1.4 (3) | C16—C17—C22—N3 | 1.2 (3) |
C2—N2—C9—C10 | −104.2 (3) | C16—N4—C23—C28 | −107.2 (3) |
C2—N2—C9—C14 | 78.5 (4) | C16—N4—C23—C24 | 77.5 (4) |
C14—C9—C10—C11 | −3.1 (4) | C28—C23—C24—C25 | 1.6 (5) |
N2—C9—C10—C11 | 179.5 (2) | N4—C23—C24—C25 | 176.9 (3) |
C9—C10—C11—C12 | 1.9 (4) | C23—C24—C25—C26 | −0.1 (5) |
C10—C11—C12—C13 | 0.5 (5) | C24—C25—C26—C27 | −0.9 (5) |
C11—C12—C13—C14 | −1.5 (5) | C25—C26—C27—C28 | 0.2 (5) |
C10—C9—C14—C13 | 2.1 (4) | C26—C27—C28—C23 | 1.4 (5) |
N2—C9—C14—C13 | 179.4 (2) | C24—C23—C28—C27 | −2.3 (5) |
C12—C13—C14—C9 | 0.3 (4) | N4—C23—C28—C27 | −177.6 (3) |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.86 (3) | 2.11 (2) | 2.940 (3) | 161 (3) |
N3—H3···N2 | 0.86 (3) | 2.28 (3) | 3.111 (3) | 164 (3) |
Symmetry code: (i) x+1/2, −y+3/2, z. |
Experimental details
Crystal data |
Chemical formula | C14H10N2O |
Mr | 222.24 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 293 |
a, b, c (Å) | 20.1647 (4), 5.0223 (1), 21.8791 (5) |
V (Å3) | 2215.77 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.3 × 0.3 × 0.3 |
|
Data collection |
Diffractometer | Bruker APEXII diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15055, 2619, 2042 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.118, 1.10 |
No. of reflections | 2619 |
No. of parameters | 315 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.20 |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.86 (3) | 2.11 (2) | 2.940 (3) | 161 (3) |
N3—H3···N2 | 0.86 (3) | 2.28 (3) | 3.111 (3) | 164 (3) |
Symmetry code: (i) x+1/2, −y+3/2, z. |
Acknowledgements
We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.
References
Akkurt, M., Öztürk, S., Erçağ, A., Özgür, M. Ü. & Heinemann, F. W. (2003). Acta Cryst. E59, o780–o782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Grimshaw, J. & Begley, W. J. (1974). Synthesis, pp. 496–498. CrossRef Google Scholar
Hökelek, T., Erçag, A., Çoruh, U., Vazquez-Lopez, E. M. & Özgür, M. Ü. (2006). Anal. Sci. X-Ray Struct. Anal. Online, 21, x129–x130. Google Scholar
Öztürk, S., Akkurt, M., Özgür, M. Ü., Erçağ, A. & Heinemann, F. W. (2003). Acta Cryst. E59, o569–o571. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
 | CRYSTALLOGRAPHIC COMMUNICATIONS |
ISSN: 2056-9890
Open

access