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6-Hydroxy-
N-(4-methoxyphenyl)-4-oxo-2,4-dihydro-1
H-pyrrolo[3,2,1-
ij]quinoline-5-carboxamide, C
19H
16N
2O
4, possesses strong diuretic properties and can be used as a new hypertension remedy. Two polymorphic modifications of this compound have been found, namely the triclinic polymorph (space group
P), with one molecule in the asymmetric unit, and the monoclinic polymorph (space group
P2
1/
n), with two molecules in asymmetric unit. An analysis of the pairwise interaction energies between the molecules in the crystal phase revealed differences in the crystal packing. The triclinic form has only one level of organization, namely a chain/column, while the monoclinic form has two levels of organization, with a chain/column as the primary basic structural motif and a layer as the secondary basic structural motif.
Supporting information
CCDC references: 1863529; 1863530
For both structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).
6-Hydroxy-
N-(4-methoxyphenyl)-4-oxo-2,4-dihydro-1
H-pyrrolo[3,2,1-
ij]quinoline-5-carboxamide (1m)
top
Crystal data top
C19H16N2O4 | F(000) = 1408 |
Mr = 336.34 | Dx = 1.439 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 16.3612 (6) Å | Cell parameters from 4692 reflections |
b = 8.4646 (3) Å | θ = 3.4–29.2° |
c = 23.6668 (12) Å | µ = 0.10 mm−1 |
β = 108.718 (5)° | T = 293 K |
V = 3104.3 (2) Å3 | Parallelepiped, colourless |
Z = 8 | 0.20 × 0.10 × 0.10 mm |
Data collection top
Agilent Xcalibur Sapphire3 diffractometer | 9030 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5185 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.039 |
ω–scan | θmax = 30.0°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −23→23 |
Tmin = 0.936, Tmax = 1.000 | k = −11→11 |
34873 measured reflections | l = −33→32 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.075P)2 + 0.1828P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
9030 reflections | Δρmax = 0.43 e Å−3 |
469 parameters | Δρmin = −0.19 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.74686 (8) | 0.49626 (16) | 0.48665 (6) | 0.0587 (3) | |
O2A | 0.70068 (8) | 0.14666 (16) | 0.63233 (6) | 0.0622 (4) | |
H2OA | 0.6448 (13) | 0.168 (2) | 0.5870 (10) | 0.072 (6)* | |
O3A | 0.58038 (8) | 0.19520 (16) | 0.54028 (6) | 0.0611 (3) | |
O4A | 0.26835 (8) | 0.42695 (18) | 0.30262 (6) | 0.0681 (4) | |
N1A | 0.85249 (8) | 0.44630 (16) | 0.57365 (6) | 0.0436 (3) | |
N2A | 0.59387 (9) | 0.37211 (19) | 0.47159 (7) | 0.0526 (4) | |
H2NA | 0.6437 (12) | 0.440 (2) | 0.4637 (8) | 0.063 (5)* | |
C1A | 0.88220 (10) | 0.37660 (19) | 0.62850 (7) | 0.0425 (4) | |
C2A | 0.96700 (11) | 0.4234 (2) | 0.65878 (9) | 0.0515 (4) | |
C3A | 1.00424 (12) | 0.3636 (2) | 0.71434 (9) | 0.0599 (5) | |
H3A | 1.060439 | 0.391757 | 0.736214 | 0.072* | |
C4A | 0.95778 (13) | 0.2587 (3) | 0.73894 (9) | 0.0654 (5) | |
H4A | 0.984081 | 0.219074 | 0.777134 | 0.078* | |
C5A | 0.87500 (12) | 0.2133 (2) | 0.70817 (8) | 0.0558 (5) | |
H5A | 0.845824 | 0.143024 | 0.725087 | 0.067* | |
C6A | 0.83457 (10) | 0.2749 (2) | 0.65042 (8) | 0.0463 (4) | |
C7A | 0.74839 (11) | 0.2460 (2) | 0.61244 (8) | 0.0463 (4) | |
C8A | 0.71632 (10) | 0.3204 (2) | 0.55778 (8) | 0.0443 (4) | |
C9A | 0.77049 (10) | 0.4271 (2) | 0.53587 (7) | 0.0443 (4) | |
C10A | 0.91971 (11) | 0.5454 (2) | 0.56190 (8) | 0.0515 (4) | |
H10A | 0.900249 | 0.653749 | 0.553662 | 0.062* | |
H10B | 0.935160 | 0.504818 | 0.528352 | 0.062* | |
C11A | 0.99610 (11) | 0.5344 (2) | 0.61976 (9) | 0.0574 (5) | |
H11A | 1.046828 | 0.493512 | 0.611972 | 0.069* | |
H11B | 1.009643 | 0.637359 | 0.638422 | 0.069* | |
C12A | 0.62522 (10) | 0.2913 (2) | 0.52212 (8) | 0.0478 (4) | |
C13A | 0.50888 (10) | 0.3741 (2) | 0.43050 (8) | 0.0470 (4) | |
C14A | 0.44826 (11) | 0.2568 (2) | 0.42463 (9) | 0.0572 (5) | |
H14A | 0.461797 | 0.168149 | 0.449062 | 0.069* | |
C15A | 0.36672 (11) | 0.2709 (3) | 0.38217 (9) | 0.0584 (5) | |
H15A | 0.325829 | 0.191907 | 0.378589 | 0.070* | |
C16A | 0.34666 (10) | 0.4006 (2) | 0.34573 (8) | 0.0523 (4) | |
C17A | 0.40749 (12) | 0.5162 (2) | 0.35083 (9) | 0.0589 (5) | |
H17A | 0.394352 | 0.603621 | 0.325711 | 0.071* | |
C18A | 0.48782 (12) | 0.5031 (2) | 0.39300 (9) | 0.0559 (5) | |
H18A | 0.528464 | 0.582360 | 0.396261 | 0.067* | |
C19A | 0.20382 (13) | 0.3108 (4) | 0.29391 (12) | 0.0920 (8) | |
H19D | 0.153321 | 0.342948 | 0.262212 | 0.138* | |
H19E | 0.189588 | 0.297943 | 0.329963 | 0.138* | |
H19F | 0.224567 | 0.212397 | 0.283621 | 0.138* | |
O1B | 0.04148 (7) | 0.75087 (15) | 0.52178 (6) | 0.0547 (3) | |
O2B | 0.16469 (10) | 1.10893 (16) | 0.41594 (6) | 0.0629 (4) | |
H2B | 0.0997 (19) | 1.097 (3) | 0.3881 (12) | 0.122 (10)* | |
O3B | 0.01404 (9) | 1.02595 (16) | 0.36929 (6) | 0.0623 (4) | |
O4B | −0.37976 (9) | 0.77522 (19) | 0.25318 (6) | 0.0698 (4) | |
N1B | 0.17953 (9) | 0.82858 (16) | 0.55953 (6) | 0.0461 (3) | |
N2B | −0.05060 (10) | 0.85478 (19) | 0.41577 (7) | 0.0508 (4) | |
H2NB | −0.0395 (14) | 0.807 (3) | 0.4485 (10) | 0.075 (7)* | |
C1B | 0.24943 (11) | 0.91730 (19) | 0.55775 (8) | 0.0454 (4) | |
C2B | 0.32110 (11) | 0.8902 (2) | 0.60702 (8) | 0.0506 (4) | |
C3B | 0.39528 (12) | 0.9713 (2) | 0.61031 (10) | 0.0598 (5) | |
H3B | 0.445269 | 0.955582 | 0.642410 | 0.072* | |
C4B | 0.39498 (13) | 1.0772 (2) | 0.56513 (10) | 0.0637 (5) | |
H4B | 0.445044 | 1.133367 | 0.568074 | 0.076* | |
C5B | 0.32319 (13) | 1.1012 (2) | 0.51657 (10) | 0.0593 (5) | |
H5B | 0.324988 | 1.172299 | 0.487043 | 0.071* | |
C6B | 0.24665 (11) | 1.0179 (2) | 0.51143 (8) | 0.0480 (4) | |
C7B | 0.16733 (12) | 1.02105 (19) | 0.46283 (8) | 0.0476 (4) | |
C8B | 0.09630 (11) | 0.93260 (19) | 0.46489 (8) | 0.0451 (4) | |
C9B | 0.10185 (11) | 0.83223 (19) | 0.51611 (8) | 0.0442 (4) | |
C10B | 0.20191 (11) | 0.7322 (2) | 0.61391 (8) | 0.0534 (4) | |
H10C | 0.193126 | 0.620777 | 0.604224 | 0.064* | |
H10D | 0.167387 | 0.761914 | 0.638739 | 0.064* | |
C11B | 0.29861 (12) | 0.7682 (2) | 0.64571 (10) | 0.0629 (5) | |
H11C | 0.307629 | 0.809139 | 0.685534 | 0.076* | |
H11D | 0.333335 | 0.673827 | 0.648551 | 0.076* | |
C12B | 0.01696 (11) | 0.9412 (2) | 0.41345 (8) | 0.0487 (4) | |
C13B | −0.13289 (11) | 0.8364 (2) | 0.37293 (8) | 0.0480 (4) | |
C14B | −0.15961 (12) | 0.9098 (2) | 0.31745 (8) | 0.0574 (5) | |
H14B | −0.121916 | 0.975500 | 0.306232 | 0.069* | |
C15B | −0.24170 (12) | 0.8853 (2) | 0.27922 (9) | 0.0597 (5) | |
H15B | −0.258941 | 0.934357 | 0.242099 | 0.072* | |
C16B | −0.29903 (11) | 0.7893 (2) | 0.29486 (8) | 0.0527 (4) | |
C17B | −0.27343 (11) | 0.7156 (2) | 0.34979 (8) | 0.0521 (4) | |
H17B | −0.311393 | 0.650005 | 0.360766 | 0.062* | |
C18B | −0.19070 (11) | 0.7402 (2) | 0.38840 (8) | 0.0510 (4) | |
H18B | −0.173635 | 0.691119 | 0.425511 | 0.061* | |
C19B | −0.44396 (13) | 0.6938 (3) | 0.26915 (10) | 0.0739 (6) | |
H19A | −0.496563 | 0.693558 | 0.236054 | 0.111* | |
H19B | −0.453541 | 0.745325 | 0.302620 | 0.111* | |
H19C | −0.425626 | 0.587021 | 0.279694 | 0.111* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0512 (7) | 0.0707 (9) | 0.0502 (8) | −0.0037 (6) | 0.0109 (6) | 0.0115 (6) |
O2A | 0.0534 (7) | 0.0717 (9) | 0.0629 (9) | −0.0112 (7) | 0.0207 (7) | 0.0129 (7) |
O3A | 0.0478 (7) | 0.0727 (9) | 0.0621 (9) | −0.0126 (6) | 0.0163 (6) | 0.0021 (7) |
O4A | 0.0468 (7) | 0.0895 (10) | 0.0583 (9) | 0.0047 (7) | 0.0035 (6) | −0.0025 (7) |
N1A | 0.0387 (7) | 0.0461 (7) | 0.0477 (9) | −0.0031 (6) | 0.0163 (6) | 0.0024 (6) |
N2A | 0.0423 (7) | 0.0629 (9) | 0.0488 (9) | 0.0001 (7) | 0.0094 (7) | 0.0008 (7) |
C1A | 0.0418 (8) | 0.0432 (9) | 0.0409 (9) | 0.0047 (7) | 0.0110 (7) | −0.0019 (7) |
C2A | 0.0436 (9) | 0.0513 (10) | 0.0570 (12) | −0.0002 (8) | 0.0123 (8) | −0.0026 (8) |
C3A | 0.0437 (9) | 0.0690 (12) | 0.0584 (12) | −0.0022 (9) | 0.0046 (9) | 0.0003 (10) |
C4A | 0.0605 (11) | 0.0759 (13) | 0.0510 (12) | 0.0023 (10) | 0.0055 (9) | 0.0105 (10) |
C5A | 0.0570 (10) | 0.0628 (11) | 0.0483 (11) | 0.0000 (9) | 0.0176 (9) | 0.0084 (9) |
C6A | 0.0452 (9) | 0.0507 (9) | 0.0455 (10) | 0.0015 (8) | 0.0180 (8) | −0.0018 (8) |
C7A | 0.0494 (9) | 0.0454 (9) | 0.0502 (11) | −0.0007 (7) | 0.0246 (8) | 0.0002 (8) |
C8A | 0.0368 (8) | 0.0484 (9) | 0.0486 (10) | −0.0023 (7) | 0.0147 (7) | −0.0094 (7) |
C9A | 0.0453 (8) | 0.0471 (9) | 0.0399 (10) | 0.0045 (7) | 0.0131 (7) | −0.0013 (7) |
C10A | 0.0465 (9) | 0.0494 (9) | 0.0616 (12) | −0.0070 (8) | 0.0214 (9) | −0.0005 (8) |
C11A | 0.0471 (9) | 0.0537 (10) | 0.0708 (13) | −0.0080 (8) | 0.0181 (9) | −0.0015 (9) |
C12A | 0.0414 (8) | 0.0535 (10) | 0.0497 (11) | −0.0019 (8) | 0.0162 (8) | −0.0070 (8) |
C13A | 0.0402 (8) | 0.0578 (10) | 0.0424 (10) | 0.0008 (8) | 0.0122 (7) | −0.0075 (8) |
C14A | 0.0472 (9) | 0.0641 (11) | 0.0573 (12) | −0.0014 (9) | 0.0127 (8) | 0.0044 (9) |
C15A | 0.0440 (9) | 0.0732 (13) | 0.0553 (12) | −0.0087 (9) | 0.0123 (8) | −0.0019 (10) |
C16A | 0.0412 (9) | 0.0703 (12) | 0.0435 (10) | 0.0057 (9) | 0.0110 (8) | −0.0094 (9) |
C17A | 0.0588 (11) | 0.0565 (11) | 0.0540 (12) | 0.0049 (9) | 0.0080 (9) | −0.0003 (9) |
C18A | 0.0528 (10) | 0.0523 (10) | 0.0578 (12) | −0.0039 (9) | 0.0109 (9) | −0.0042 (9) |
C19A | 0.0479 (11) | 0.133 (2) | 0.0800 (18) | −0.0116 (14) | −0.0009 (11) | −0.0004 (16) |
O1B | 0.0478 (6) | 0.0621 (8) | 0.0530 (8) | −0.0100 (6) | 0.0145 (6) | 0.0083 (6) |
O2B | 0.0735 (9) | 0.0617 (8) | 0.0604 (9) | −0.0073 (7) | 0.0308 (7) | 0.0105 (7) |
O3B | 0.0682 (8) | 0.0669 (8) | 0.0519 (8) | −0.0001 (7) | 0.0194 (7) | 0.0134 (6) |
O4B | 0.0569 (8) | 0.0909 (10) | 0.0530 (9) | 0.0029 (7) | 0.0054 (6) | 0.0048 (7) |
N1B | 0.0475 (7) | 0.0428 (7) | 0.0479 (9) | −0.0048 (6) | 0.0150 (7) | 0.0015 (6) |
N2B | 0.0507 (8) | 0.0577 (9) | 0.0435 (9) | 0.0021 (7) | 0.0146 (7) | 0.0050 (7) |
C1B | 0.0499 (9) | 0.0378 (8) | 0.0535 (11) | −0.0055 (7) | 0.0233 (8) | −0.0089 (7) |
C2B | 0.0495 (9) | 0.0471 (9) | 0.0562 (11) | −0.0033 (8) | 0.0184 (8) | −0.0080 (8) |
C3B | 0.0505 (10) | 0.0610 (11) | 0.0671 (13) | −0.0086 (9) | 0.0180 (9) | −0.0162 (10) |
C4B | 0.0567 (11) | 0.0626 (12) | 0.0784 (15) | −0.0167 (10) | 0.0312 (11) | −0.0163 (11) |
C5B | 0.0663 (12) | 0.0536 (11) | 0.0696 (14) | −0.0120 (9) | 0.0378 (11) | −0.0068 (9) |
C6B | 0.0546 (10) | 0.0419 (9) | 0.0545 (11) | −0.0050 (8) | 0.0274 (9) | −0.0074 (8) |
C7B | 0.0598 (10) | 0.0394 (8) | 0.0513 (11) | 0.0015 (8) | 0.0287 (9) | −0.0005 (7) |
C8B | 0.0520 (9) | 0.0405 (8) | 0.0476 (10) | 0.0014 (7) | 0.0227 (8) | −0.0011 (7) |
C9B | 0.0467 (9) | 0.0419 (8) | 0.0470 (10) | −0.0017 (7) | 0.0193 (8) | −0.0031 (7) |
C10B | 0.0553 (10) | 0.0528 (10) | 0.0479 (11) | −0.0080 (8) | 0.0107 (8) | 0.0054 (8) |
C11B | 0.0541 (10) | 0.0645 (12) | 0.0615 (13) | −0.0078 (9) | 0.0063 (9) | 0.0046 (10) |
C12B | 0.0569 (10) | 0.0460 (9) | 0.0473 (11) | 0.0049 (8) | 0.0223 (8) | −0.0022 (8) |
C13B | 0.0506 (9) | 0.0495 (9) | 0.0456 (10) | 0.0086 (8) | 0.0177 (8) | −0.0005 (8) |
C14B | 0.0599 (11) | 0.0684 (12) | 0.0468 (11) | −0.0011 (10) | 0.0211 (9) | 0.0050 (9) |
C15B | 0.0648 (11) | 0.0707 (13) | 0.0437 (11) | 0.0078 (10) | 0.0177 (9) | 0.0074 (9) |
C16B | 0.0516 (10) | 0.0573 (10) | 0.0474 (11) | 0.0080 (9) | 0.0134 (8) | −0.0048 (8) |
C17B | 0.0518 (10) | 0.0502 (10) | 0.0540 (11) | 0.0046 (8) | 0.0166 (9) | 0.0026 (8) |
C18B | 0.0563 (10) | 0.0505 (10) | 0.0454 (11) | 0.0091 (8) | 0.0151 (8) | 0.0043 (8) |
C19B | 0.0570 (11) | 0.0972 (17) | 0.0632 (14) | −0.0075 (12) | 0.0133 (10) | −0.0110 (12) |
Geometric parameters (Å, º) top
O1A—C9A | 1.249 (2) | O1B—C9B | 1.2461 (19) |
O2A—C7A | 1.332 (2) | O2B—C7B | 1.325 (2) |
O3A—C12A | 1.260 (2) | O3B—C12B | 1.256 (2) |
O4A—C16A | 1.376 (2) | O4B—C16B | 1.377 (2) |
O4A—C19A | 1.408 (3) | O4B—C19B | 1.406 (3) |
N1A—C9A | 1.362 (2) | N1B—C9B | 1.354 (2) |
N1A—C1A | 1.365 (2) | N1B—C1B | 1.380 (2) |
N1A—C10A | 1.479 (2) | N1B—C10B | 1.468 (2) |
N2A—C12A | 1.330 (2) | N2B—C12B | 1.341 (2) |
N2A—C13A | 1.418 (2) | N2B—C13B | 1.410 (2) |
C1A—C6A | 1.370 (2) | C1B—C6B | 1.377 (2) |
C1A—C2A | 1.399 (2) | C1B—C2B | 1.382 (2) |
C2A—C3A | 1.358 (3) | C2B—C3B | 1.374 (2) |
C2A—C11A | 1.498 (3) | C2B—C11B | 1.502 (3) |
C3A—C4A | 1.410 (3) | C3B—C4B | 1.394 (3) |
C4A—C5A | 1.371 (3) | C4B—C5B | 1.369 (3) |
C5A—C6A | 1.413 (3) | C5B—C6B | 1.408 (2) |
C6A—C7A | 1.429 (2) | C6B—C7B | 1.432 (3) |
C7A—C8A | 1.382 (2) | C7B—C8B | 1.396 (2) |
C8A—C9A | 1.472 (2) | C8B—C9B | 1.459 (2) |
C8A—C12A | 1.479 (2) | C8B—C12B | 1.469 (3) |
C10A—C11A | 1.532 (3) | C10B—C11B | 1.549 (2) |
C13A—C14A | 1.378 (2) | C13B—C18B | 1.383 (2) |
C13A—C18A | 1.379 (3) | C13B—C14B | 1.390 (2) |
C14A—C15A | 1.394 (3) | C14B—C15B | 1.373 (3) |
C15A—C16A | 1.369 (3) | C15B—C16B | 1.379 (3) |
C16A—C17A | 1.373 (3) | C16B—C17B | 1.380 (3) |
C17A—C18A | 1.376 (3) | C17B—C18B | 1.384 (2) |
| | | |
C16A—O4A—C19A | 118.10 (17) | C16B—O4B—C19B | 118.52 (16) |
C9A—N1A—C1A | 123.21 (14) | C9B—N1B—C1B | 123.34 (15) |
C9A—N1A—C10A | 125.40 (14) | C9B—N1B—C10B | 125.96 (14) |
C1A—N1A—C10A | 111.38 (13) | C1B—N1B—C10B | 110.69 (14) |
C12A—N2A—C13A | 129.29 (16) | C12B—N2B—C13B | 129.78 (17) |
N1A—C1A—C6A | 124.00 (15) | C6B—C1B—N1B | 123.00 (16) |
N1A—C1A—C2A | 110.89 (15) | C6B—C1B—C2B | 125.20 (16) |
C6A—C1A—C2A | 125.11 (16) | N1B—C1B—C2B | 111.79 (15) |
C3A—C2A—C1A | 116.96 (17) | C3B—C2B—C1B | 117.37 (17) |
C3A—C2A—C11A | 134.32 (16) | C3B—C2B—C11B | 133.89 (18) |
C1A—C2A—C11A | 108.72 (16) | C1B—C2B—C11B | 108.71 (15) |
C2A—C3A—C4A | 120.07 (17) | C2B—C3B—C4B | 119.47 (19) |
C5A—C4A—C3A | 121.91 (19) | C5B—C4B—C3B | 121.99 (18) |
C4A—C5A—C6A | 119.12 (18) | C4B—C5B—C6B | 119.87 (19) |
C1A—C6A—C5A | 116.83 (16) | C1B—C6B—C5B | 116.07 (18) |
C1A—C6A—C7A | 115.82 (16) | C1B—C6B—C7B | 116.16 (15) |
C5A—C6A—C7A | 127.33 (16) | C5B—C6B—C7B | 127.73 (17) |
O2A—C7A—C8A | 121.93 (16) | O2B—C7B—C8B | 121.76 (17) |
O2A—C7A—C6A | 117.23 (16) | O2B—C7B—C6B | 117.44 (16) |
C8A—C7A—C6A | 120.84 (15) | C8B—C7B—C6B | 120.79 (16) |
C7A—C8A—C9A | 121.26 (15) | C7B—C8B—C9B | 120.71 (16) |
C7A—C8A—C12A | 117.96 (15) | C7B—C8B—C12B | 117.93 (16) |
C9A—C8A—C12A | 120.78 (16) | C9B—C8B—C12B | 121.35 (15) |
O1A—C9A—N1A | 120.08 (15) | O1B—C9B—N1B | 119.28 (15) |
O1A—C9A—C8A | 125.12 (15) | O1B—C9B—C8B | 124.83 (16) |
N1A—C9A—C8A | 114.79 (15) | N1B—C9B—C8B | 115.89 (14) |
N1A—C10A—C11A | 103.89 (14) | N1B—C10B—C11B | 104.19 (14) |
C2A—C11A—C10A | 105.05 (14) | C2B—C11B—C10B | 104.54 (15) |
O3A—C12A—N2A | 122.71 (16) | O3B—C12B—N2B | 122.27 (17) |
O3A—C12A—C8A | 120.23 (17) | O3B—C12B—C8B | 120.37 (16) |
N2A—C12A—C8A | 117.05 (16) | N2B—C12B—C8B | 117.36 (16) |
C14A—C13A—C18A | 118.83 (16) | C18B—C13B—C14B | 118.59 (17) |
C14A—C13A—N2A | 125.16 (17) | C18B—C13B—N2B | 116.78 (16) |
C18A—C13A—N2A | 115.99 (16) | C14B—C13B—N2B | 124.62 (17) |
C13A—C14A—C15A | 120.17 (18) | C15B—C14B—C13B | 119.95 (18) |
C16A—C15A—C14A | 120.18 (18) | C14B—C15B—C16B | 121.21 (18) |
C15A—C16A—C17A | 119.72 (17) | O4B—C16B—C15B | 115.94 (17) |
C15A—C16A—O4A | 125.10 (17) | O4B—C16B—C17B | 124.56 (17) |
C17A—C16A—O4A | 115.18 (18) | C15B—C16B—C17B | 119.50 (17) |
C16A—C17A—C18A | 120.19 (18) | C16B—C17B—C18B | 119.37 (18) |
C17A—C18A—C13A | 120.90 (18) | C13B—C18B—C17B | 121.38 (17) |
| | | |
C9A—N1A—C1A—C6A | 3.0 (2) | C9B—N1B—C1B—C6B | −0.1 (2) |
C10A—N1A—C1A—C6A | −178.04 (15) | C10B—N1B—C1B—C6B | 179.59 (16) |
C9A—N1A—C1A—C2A | −176.87 (15) | C9B—N1B—C1B—C2B | −179.17 (15) |
C10A—N1A—C1A—C2A | 2.08 (19) | C10B—N1B—C1B—C2B | 0.6 (2) |
N1A—C1A—C2A—C3A | 179.43 (16) | C6B—C1B—C2B—C3B | 0.7 (3) |
C6A—C1A—C2A—C3A | −0.4 (3) | N1B—C1B—C2B—C3B | 179.66 (15) |
N1A—C1A—C2A—C11A | −0.3 (2) | C6B—C1B—C2B—C11B | −177.65 (17) |
C6A—C1A—C2A—C11A | 179.78 (16) | N1B—C1B—C2B—C11B | 1.4 (2) |
C1A—C2A—C3A—C4A | 0.3 (3) | C1B—C2B—C3B—C4B | 0.9 (3) |
C11A—C2A—C3A—C4A | 180.0 (2) | C11B—C2B—C3B—C4B | 178.7 (2) |
C2A—C3A—C4A—C5A | 0.3 (3) | C2B—C3B—C4B—C5B | −1.4 (3) |
C3A—C4A—C5A—C6A | −0.8 (3) | C3B—C4B—C5B—C6B | 0.3 (3) |
N1A—C1A—C6A—C5A | −179.84 (15) | N1B—C1B—C6B—C5B | 179.42 (15) |
C2A—C1A—C6A—C5A | 0.0 (3) | C2B—C1B—C6B—C5B | −1.7 (3) |
N1A—C1A—C6A—C7A | −1.3 (2) | N1B—C1B—C6B—C7B | −2.7 (2) |
C2A—C1A—C6A—C7A | 178.60 (16) | C2B—C1B—C6B—C7B | 176.18 (16) |
C4A—C5A—C6A—C1A | 0.6 (3) | C4B—C5B—C6B—C1B | 1.2 (3) |
C4A—C5A—C6A—C7A | −177.81 (18) | C4B—C5B—C6B—C7B | −176.40 (18) |
C1A—C6A—C7A—O2A | 179.50 (15) | C1B—C6B—C7B—O2B | −175.72 (14) |
C5A—C6A—C7A—O2A | −2.1 (3) | C5B—C6B—C7B—O2B | 1.9 (3) |
C1A—C6A—C7A—C8A | −1.3 (2) | C1B—C6B—C7B—C8B | 3.4 (2) |
C5A—C6A—C7A—C8A | 177.14 (17) | C5B—C6B—C7B—C8B | −179.08 (16) |
O2A—C7A—C8A—C9A | −178.63 (15) | O2B—C7B—C8B—C9B | 177.73 (15) |
C6A—C7A—C8A—C9A | 2.2 (2) | C6B—C7B—C8B—C9B | −1.3 (2) |
O2A—C7A—C8A—C12A | 2.2 (2) | O2B—C7B—C8B—C12B | −0.9 (2) |
C6A—C7A—C8A—C12A | −176.96 (15) | C6B—C7B—C8B—C12B | −179.92 (15) |
C1A—N1A—C9A—O1A | 178.83 (15) | C1B—N1B—C9B—O1B | −178.48 (14) |
C10A—N1A—C9A—O1A | 0.0 (3) | C10B—N1B—C9B—O1B | 1.8 (3) |
C1A—N1A—C9A—C8A | −2.0 (2) | C1B—N1B—C9B—C8B | 2.3 (2) |
C10A—N1A—C9A—C8A | 179.25 (14) | C10B—N1B—C9B—C8B | −177.40 (15) |
C7A—C8A—C9A—O1A | 178.60 (16) | C7B—C8B—C9B—O1B | 179.28 (15) |
C12A—C8A—C9A—O1A | −2.3 (3) | C12B—C8B—C9B—O1B | −2.1 (3) |
C7A—C8A—C9A—N1A | −0.6 (2) | C7B—C8B—C9B—N1B | −1.5 (2) |
C12A—C8A—C9A—N1A | 178.55 (14) | C12B—C8B—C9B—N1B | 177.04 (14) |
C9A—N1A—C10A—C11A | 176.08 (15) | C9B—N1B—C10B—C11B | 177.59 (16) |
C1A—N1A—C10A—C11A | −2.84 (19) | C1B—N1B—C10B—C11B | −2.13 (19) |
C3A—C2A—C11A—C10A | 178.9 (2) | C3B—C2B—C11B—C10B | 179.5 (2) |
C1A—C2A—C11A—C10A | −1.4 (2) | C1B—C2B—C11B—C10B | −2.6 (2) |
N1A—C10A—C11A—C2A | 2.46 (18) | N1B—C10B—C11B—C2B | 2.8 (2) |
C13A—N2A—C12A—O3A | 2.4 (3) | C13B—N2B—C12B—O3B | 1.5 (3) |
C13A—N2A—C12A—C8A | −176.59 (16) | C13B—N2B—C12B—C8B | −177.99 (16) |
C7A—C8A—C12A—O3A | −3.5 (2) | C7B—C8B—C12B—O3B | 0.0 (2) |
C9A—C8A—C12A—O3A | 177.37 (15) | C9B—C8B—C12B—O3B | −178.61 (15) |
C7A—C8A—C12A—N2A | 175.53 (15) | C7B—C8B—C12B—N2B | 179.51 (15) |
C9A—C8A—C12A—N2A | −3.6 (2) | C9B—C8B—C12B—N2B | 0.9 (2) |
C12A—N2A—C13A—C14A | −21.9 (3) | C12B—N2B—C13B—C18B | −178.96 (16) |
C12A—N2A—C13A—C18A | 159.89 (18) | C12B—N2B—C13B—C14B | −0.1 (3) |
C18A—C13A—C14A—C15A | −1.2 (3) | C18B—C13B—C14B—C15B | −0.4 (3) |
N2A—C13A—C14A—C15A | −179.40 (17) | N2B—C13B—C14B—C15B | −179.26 (17) |
C13A—C14A—C15A—C16A | 0.6 (3) | C13B—C14B—C15B—C16B | 0.4 (3) |
C14A—C15A—C16A—C17A | 0.6 (3) | C19B—O4B—C16B—C15B | −172.82 (18) |
C14A—C15A—C16A—O4A | −179.67 (17) | C19B—O4B—C16B—C17B | 6.8 (3) |
C19A—O4A—C16A—C15A | −1.5 (3) | C14B—C15B—C16B—O4B | 179.23 (18) |
C19A—O4A—C16A—C17A | 178.27 (19) | C14B—C15B—C16B—C17B | −0.4 (3) |
C15A—C16A—C17A—C18A | −1.0 (3) | O4B—C16B—C17B—C18B | −179.18 (17) |
O4A—C16A—C17A—C18A | 179.19 (17) | C15B—C16B—C17B—C18B | 0.4 (3) |
C16A—C17A—C18A—C13A | 0.4 (3) | C14B—C13B—C18B—C17B | 0.4 (3) |
C14A—C13A—C18A—C17A | 0.7 (3) | N2B—C13B—C18B—C17B | 179.38 (16) |
N2A—C13A—C18A—C17A | 179.11 (17) | C16B—C17B—C18B—C13B | −0.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2OA···O3A | 1.18 (2) | 1.28 (2) | 2.4571 (18) | 175.3 (19) |
O2B—H2B···O3B | 1.06 (3) | 1.46 (3) | 2.4579 (19) | 155 (3) |
N2A—H2NA···O1A | 1.060 (19) | 1.669 (19) | 2.6314 (19) | 148.4 (16) |
N2B—H2NB···O1B | 0.84 (2) | 1.87 (2) | 2.629 (2) | 149 (2) |
6-Hydroxy-
N-(4-methoxyphenyl)-4-oxo-2,4-dihydro-1
H-pyrrolo[3,2,1-
ij]quinoline-5-carboxamide (1t)
top
Crystal data top
C19H16N2O4 | Z = 2 |
Mr = 336.34 | F(000) = 352 |
Triclinic, P1 | Dx = 1.450 Mg m−3 |
a = 7.1048 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0882 (16) Å | Cell parameters from 568 reflections |
c = 11.5171 (17) Å | θ = 3.7–23.0° |
α = 73.761 (17)° | µ = 0.10 mm−1 |
β = 87.27 (2)° | T = 293 K |
γ = 76.48 (2)° | Stick, colourless |
V = 770.4 (3) Å3 | 0.20 × 0.05 × 0.04 mm |
Data collection top
Agilent Xcalibur Sapphire3 diffractometer | 2718 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1417 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.052 |
ω–scan | θmax = 25.0°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −8→8 |
Tmin = 0.149, Tmax = 1.000 | k = −11→11 |
5035 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.262 | w = 1/[σ2(Fo2) + (0.1293P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
2718 reflections | Δρmax = 0.39 e Å−3 |
235 parameters | Δρmin = −0.23 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.6158 (4) | 0.7240 (3) | 0.4080 (2) | 0.0554 (9) | |
O2 | 0.8627 (5) | 0.2542 (3) | 0.6600 (3) | 0.0565 (9) | |
H2O | 0.785 (8) | 0.312 (5) | 0.725 (4) | 0.089 (16)* | |
O3 | 0.6756 (4) | 0.4363 (3) | 0.7553 (2) | 0.0541 (9) | |
O4 | 0.2556 (5) | 0.9886 (3) | 0.9527 (3) | 0.0738 (11) | |
N1 | 0.7900 (5) | 0.5530 (3) | 0.3314 (3) | 0.0469 (9) | |
N2 | 0.5565 (5) | 0.6629 (4) | 0.6413 (3) | 0.0466 (9) | |
H2N | 0.557 (6) | 0.711 (5) | 0.561 (4) | 0.065 (14)* | |
C1 | 0.8900 (6) | 0.4165 (4) | 0.3412 (4) | 0.0432 (10) | |
C2 | 0.9568 (6) | 0.3965 (4) | 0.2307 (4) | 0.0500 (11) | |
C3 | 1.0568 (7) | 0.2640 (5) | 0.2304 (4) | 0.0597 (13) | |
H3 | 1.102870 | 0.246277 | 0.157988 | 0.072* | |
C4 | 1.0913 (7) | 0.1533 (5) | 0.3385 (4) | 0.0601 (13) | |
H4 | 1.159102 | 0.063109 | 0.336712 | 0.072* | |
C5 | 1.0253 (6) | 0.1776 (4) | 0.4473 (4) | 0.0519 (12) | |
H5 | 1.051723 | 0.104293 | 0.518496 | 0.062* | |
C6 | 0.9196 (6) | 0.3112 (4) | 0.4507 (4) | 0.0430 (10) | |
C7 | 0.8368 (6) | 0.3535 (4) | 0.5539 (4) | 0.0428 (10) | |
C8 | 0.7325 (6) | 0.4912 (4) | 0.5436 (3) | 0.0406 (10) | |
C9 | 0.7060 (6) | 0.5986 (4) | 0.4267 (4) | 0.0441 (10) | |
C10 | 0.7814 (7) | 0.6378 (5) | 0.2042 (4) | 0.0578 (12) | |
H10A | 0.838659 | 0.718367 | 0.195402 | 0.069* | |
H10B | 0.648498 | 0.672179 | 0.174520 | 0.069* | |
C11 | 0.8970 (7) | 0.5370 (5) | 0.1355 (4) | 0.0571 (12) | |
H11A | 0.817615 | 0.528997 | 0.072698 | 0.069* | |
H11B | 1.009539 | 0.569805 | 0.098909 | 0.069* | |
C12 | 0.6530 (6) | 0.5287 (4) | 0.6541 (4) | 0.0437 (10) | |
C13 | 0.4783 (6) | 0.7331 (4) | 0.7283 (4) | 0.0450 (10) | |
C14 | 0.4725 (6) | 0.6697 (4) | 0.8512 (4) | 0.0493 (11) | |
H14 | 0.518296 | 0.572238 | 0.881999 | 0.059* | |
C15 | 0.3972 (7) | 0.7532 (5) | 0.9289 (4) | 0.0524 (12) | |
H15 | 0.393262 | 0.710460 | 1.011458 | 0.063* | |
C16 | 0.3290 (6) | 0.8972 (4) | 0.8850 (4) | 0.0512 (11) | |
C17 | 0.3343 (7) | 0.9597 (5) | 0.7615 (4) | 0.0608 (13) | |
H17 | 0.288018 | 1.057137 | 0.730553 | 0.073* | |
C18 | 0.4075 (7) | 0.8786 (4) | 0.6849 (4) | 0.0540 (12) | |
H18 | 0.409665 | 0.921938 | 0.602302 | 0.065* | |
C19 | 0.2421 (9) | 0.9307 (6) | 1.0795 (4) | 0.0862 (18) | |
H19A | 0.173970 | 1.003741 | 1.114580 | 0.129* | |
H19B | 0.369788 | 0.892847 | 1.114885 | 0.129* | |
H19C | 0.173314 | 0.856348 | 1.094671 | 0.129* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.070 (2) | 0.0416 (18) | 0.0480 (18) | −0.0032 (15) | 0.0050 (15) | −0.0103 (14) |
O2 | 0.069 (2) | 0.0414 (17) | 0.0489 (18) | −0.0042 (15) | 0.0029 (15) | −0.0043 (14) |
O3 | 0.069 (2) | 0.0446 (17) | 0.0426 (17) | −0.0066 (15) | 0.0072 (14) | −0.0085 (14) |
O4 | 0.111 (3) | 0.0524 (19) | 0.051 (2) | −0.0009 (18) | 0.0165 (18) | −0.0198 (16) |
N1 | 0.056 (2) | 0.046 (2) | 0.0363 (19) | −0.0090 (17) | 0.0021 (16) | −0.0100 (16) |
N2 | 0.055 (2) | 0.046 (2) | 0.038 (2) | −0.0065 (17) | 0.0080 (17) | −0.0147 (17) |
C1 | 0.042 (3) | 0.047 (2) | 0.044 (2) | −0.0117 (19) | 0.0022 (19) | −0.018 (2) |
C2 | 0.050 (3) | 0.053 (3) | 0.052 (3) | −0.012 (2) | 0.007 (2) | −0.024 (2) |
C3 | 0.059 (3) | 0.066 (3) | 0.064 (3) | −0.015 (2) | 0.018 (2) | −0.038 (3) |
C4 | 0.061 (3) | 0.051 (3) | 0.073 (3) | −0.012 (2) | 0.014 (3) | −0.027 (3) |
C5 | 0.057 (3) | 0.041 (2) | 0.060 (3) | −0.013 (2) | 0.006 (2) | −0.016 (2) |
C6 | 0.043 (2) | 0.040 (2) | 0.049 (2) | −0.0086 (19) | −0.0025 (19) | −0.0167 (19) |
C7 | 0.040 (2) | 0.044 (2) | 0.044 (2) | −0.0109 (19) | 0.0004 (18) | −0.0101 (19) |
C8 | 0.043 (2) | 0.042 (2) | 0.040 (2) | −0.0115 (19) | 0.0064 (18) | −0.0150 (18) |
C9 | 0.050 (3) | 0.045 (3) | 0.039 (2) | −0.012 (2) | 0.0042 (19) | −0.0138 (19) |
C10 | 0.066 (3) | 0.061 (3) | 0.043 (3) | −0.010 (2) | 0.009 (2) | −0.014 (2) |
C11 | 0.063 (3) | 0.066 (3) | 0.043 (2) | −0.015 (2) | 0.005 (2) | −0.015 (2) |
C12 | 0.047 (3) | 0.045 (2) | 0.040 (2) | −0.012 (2) | 0.0005 (19) | −0.0119 (19) |
C13 | 0.045 (3) | 0.046 (2) | 0.044 (2) | −0.008 (2) | 0.0045 (19) | −0.0157 (19) |
C14 | 0.058 (3) | 0.040 (2) | 0.049 (3) | −0.008 (2) | 0.006 (2) | −0.013 (2) |
C15 | 0.064 (3) | 0.055 (3) | 0.037 (2) | −0.012 (2) | 0.004 (2) | −0.012 (2) |
C16 | 0.060 (3) | 0.046 (3) | 0.046 (3) | −0.004 (2) | 0.006 (2) | −0.017 (2) |
C17 | 0.080 (4) | 0.038 (2) | 0.055 (3) | −0.001 (2) | 0.008 (2) | −0.008 (2) |
C18 | 0.065 (3) | 0.048 (3) | 0.040 (2) | −0.006 (2) | 0.008 (2) | −0.006 (2) |
C19 | 0.122 (5) | 0.076 (4) | 0.048 (3) | 0.009 (3) | 0.007 (3) | −0.024 (3) |
Geometric parameters (Å, º) top
O1—C9 | 1.241 (5) | C6—C7 | 1.429 (6) |
O2—C7 | 1.335 (5) | C7—C8 | 1.388 (6) |
O2—H2O | 1.12 (6) | C8—C9 | 1.461 (5) |
O3—C12 | 1.263 (4) | C8—C12 | 1.477 (6) |
O3—H2O | 1.44 (6) | C10—C11 | 1.527 (7) |
O4—C16 | 1.368 (5) | C10—H10A | 0.9700 |
O4—C19 | 1.420 (6) | C10—H10B | 0.9700 |
N1—C9 | 1.365 (5) | C11—H11A | 0.9700 |
N1—C1 | 1.370 (5) | C11—H11B | 0.9700 |
N1—C10 | 1.471 (5) | C13—C14 | 1.384 (6) |
N2—C12 | 1.337 (5) | C13—C18 | 1.388 (6) |
N2—C13 | 1.405 (5) | C14—C15 | 1.401 (6) |
N2—H2N | 0.92 (4) | C14—H14 | 0.9300 |
C1—C2 | 1.388 (6) | C15—C16 | 1.373 (6) |
C1—C6 | 1.391 (5) | C15—H15 | 0.9300 |
C2—C3 | 1.360 (6) | C16—C17 | 1.388 (6) |
C2—C11 | 1.511 (6) | C17—C18 | 1.371 (6) |
C3—C4 | 1.407 (6) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.383 (6) | C19—H19A | 0.9600 |
C4—H4 | 0.9300 | C19—H19B | 0.9600 |
C5—C6 | 1.392 (6) | C19—H19C | 0.9600 |
C5—H5 | 0.9300 | | |
| | | |
C7—O2—H2O | 103 (3) | C11—C10—H10A | 110.7 |
C12—O3—H2O | 103 (2) | N1—C10—H10B | 110.7 |
C16—O4—C19 | 117.9 (4) | C11—C10—H10B | 110.7 |
C9—N1—C1 | 123.8 (3) | H10A—C10—H10B | 108.8 |
C9—N1—C10 | 126.4 (3) | C2—C11—C10 | 104.5 (3) |
C1—N1—C10 | 109.8 (3) | C2—C11—H11A | 110.8 |
C12—N2—C13 | 130.6 (4) | C10—C11—H11A | 110.8 |
C12—N2—H2N | 108 (3) | C2—C11—H11B | 110.8 |
C13—N2—H2N | 121 (3) | C10—C11—H11B | 110.8 |
N1—C1—C2 | 112.5 (3) | H11A—C11—H11B | 108.9 |
N1—C1—C6 | 122.9 (4) | O3—C12—N2 | 122.4 (4) |
C2—C1—C6 | 124.6 (4) | O3—C12—C8 | 120.5 (4) |
C3—C2—C1 | 117.1 (4) | N2—C12—C8 | 117.1 (3) |
C3—C2—C11 | 135.0 (4) | C14—C13—C18 | 118.8 (4) |
C1—C2—C11 | 107.8 (4) | C14—C13—N2 | 125.4 (4) |
C2—C3—C4 | 120.8 (4) | C18—C13—N2 | 115.7 (4) |
C2—C3—H3 | 119.6 | C13—C14—C15 | 119.6 (4) |
C4—C3—H3 | 119.6 | C13—C14—H14 | 120.2 |
C5—C4—C3 | 120.5 (4) | C15—C14—H14 | 120.2 |
C5—C4—H4 | 119.7 | C16—C15—C14 | 121.0 (4) |
C3—C4—H4 | 119.7 | C16—C15—H15 | 119.5 |
C4—C5—C6 | 120.3 (4) | C14—C15—H15 | 119.5 |
C4—C5—H5 | 119.9 | O4—C16—C15 | 125.8 (4) |
C6—C5—H5 | 119.9 | O4—C16—C17 | 115.2 (4) |
C1—C6—C5 | 116.7 (4) | C15—C16—C17 | 119.0 (4) |
C1—C6—C7 | 115.8 (4) | C18—C17—C16 | 120.3 (4) |
C5—C6—C7 | 127.6 (4) | C18—C17—H17 | 119.8 |
O2—C7—C8 | 121.8 (4) | C16—C17—H17 | 119.8 |
O2—C7—C6 | 116.9 (4) | C17—C18—C13 | 121.2 (4) |
C8—C7—C6 | 121.3 (3) | C17—C18—H18 | 119.4 |
C7—C8—C9 | 121.0 (4) | C13—C18—H18 | 119.4 |
C7—C8—C12 | 118.6 (3) | O4—C19—H19A | 109.5 |
C9—C8—C12 | 120.3 (4) | O4—C19—H19B | 109.5 |
O1—C9—N1 | 118.9 (4) | H19A—C19—H19B | 109.5 |
O1—C9—C8 | 125.9 (4) | O4—C19—H19C | 109.5 |
N1—C9—C8 | 115.2 (4) | H19A—C19—H19C | 109.5 |
N1—C10—C11 | 105.2 (3) | H19B—C19—H19C | 109.5 |
N1—C10—H10A | 110.7 | | |
| | | |
C9—N1—C1—C2 | 178.4 (4) | C7—C8—C9—O1 | −180.0 (4) |
C10—N1—C1—C2 | 0.8 (5) | C12—C8—C9—O1 | −1.7 (6) |
C9—N1—C1—C6 | −1.5 (6) | C7—C8—C9—N1 | 0.1 (6) |
C10—N1—C1—C6 | −179.2 (4) | C12—C8—C9—N1 | 178.3 (3) |
N1—C1—C2—C3 | −179.5 (4) | C9—N1—C10—C11 | −179.7 (4) |
C6—C1—C2—C3 | 0.5 (6) | C1—N1—C10—C11 | −2.1 (5) |
N1—C1—C2—C11 | 0.9 (5) | C3—C2—C11—C10 | 178.3 (5) |
C6—C1—C2—C11 | −179.1 (4) | C1—C2—C11—C10 | −2.1 (5) |
C1—C2—C3—C4 | −0.6 (6) | N1—C10—C11—C2 | 2.5 (5) |
C11—C2—C3—C4 | 178.9 (5) | C13—N2—C12—O3 | 6.1 (7) |
C2—C3—C4—C5 | −0.5 (7) | C13—N2—C12—C8 | −174.4 (4) |
C3—C4—C5—C6 | 1.6 (7) | C7—C8—C12—O3 | −1.7 (6) |
N1—C1—C6—C5 | −179.5 (4) | C9—C8—C12—O3 | 180.0 (3) |
C2—C1—C6—C5 | 0.6 (6) | C7—C8—C12—N2 | 178.8 (3) |
N1—C1—C6—C7 | 0.6 (6) | C9—C8—C12—N2 | 0.5 (6) |
C2—C1—C6—C7 | −179.3 (4) | C12—N2—C13—C14 | −5.9 (7) |
C4—C5—C6—C1 | −1.6 (6) | C12—N2—C13—C18 | 172.1 (4) |
C4—C5—C6—C7 | 178.3 (4) | C18—C13—C14—C15 | −0.5 (6) |
C1—C6—C7—O2 | 179.8 (3) | N2—C13—C14—C15 | 177.4 (4) |
C5—C6—C7—O2 | −0.1 (6) | C13—C14—C15—C16 | 0.0 (7) |
C1—C6—C7—C8 | 0.5 (6) | C19—O4—C16—C15 | −2.1 (7) |
C5—C6—C7—C8 | −179.4 (4) | C19—O4—C16—C17 | 178.5 (4) |
O2—C7—C8—C9 | 179.9 (4) | C14—C15—C16—O4 | −178.9 (4) |
C6—C7—C8—C9 | −0.9 (6) | C14—C15—C16—C17 | 0.4 (7) |
O2—C7—C8—C12 | 1.6 (6) | O4—C16—C17—C18 | 179.1 (4) |
C6—C7—C8—C12 | −179.1 (3) | C15—C16—C17—C18 | −0.3 (7) |
C1—N1—C9—O1 | −178.9 (3) | C16—C17—C18—C13 | −0.2 (7) |
C10—N1—C9—O1 | −1.6 (6) | C14—C13—C18—C17 | 0.6 (7) |
C1—N1—C9—C8 | 1.1 (6) | N2—C13—C18—C17 | −177.5 (4) |
C10—N1—C9—C8 | 178.4 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O3 | 1.12 (6) | 1.44 (6) | 2.488 (4) | 153 (4) |
N2—H2N···O1 | 0.92 (4) | 1.76 (5) | 2.619 (4) | 153 (4) |
Results of crystallization from different solvents topSolvent | Crystal form | Structure |
Methanol | Stick-like | 1t |
Ethanol | Prismatic | 1m |
Ethyl acetate | Prismatic | 1m |
Acetic acid | Plate-like | Solvate with acetic acid |
Dioxane | Stick-like | Solvate with dioxane |
N,N-Dimethylformamide | Prismatic | 1m |
Selected geometric parameters for molecule 1 in the triclinic and
monoclinic polymorphic forms topParameter | Polymorph 1t | Polymorph 1m | |
| | Molecule 1A | Molecule 1B |
The mean plane of tricyclic fragment and carbamide group (Å) | | | |
| 0.01 | 0.04 | 0.04 |
| | | |
Bond lengths (Å) | | | |
C9—O1 | 1.241 (5) | 1.249 (2) | 1.246 (2) |
C12—O3 | 1.262 (4) | 1.260 (2) | 1.256 (2) |
C7—C8 | 1.388 (5) | 1.382 (2) | 1.396 (3) |
C7—O2 | 1.335 (5) | 1.332 (2) | 1.325 (2) |
| | | |
Torsion angles (°) | | | |
O3—C12—N2—C13 | 6.0 (7) | 2.4 (3) | 1.5 (3) |
C12—N2—C13—C14 | -5.8 (7) | -21.9 (3) | -0.1 (3) |
C15—C16—O4—C19 | -2.1 (7) | -1.5 (3) | -172.8 (2) |
Geometric characteristics of the intramolecular hydrogen bonds
(Å, °) in molecule 1 in the triclinic and monoclinic polymorphic
forms topD—H···A | D—H | H···A | D···A | D—H···A |
Triclinic polymorph 1t | | | | |
O2—H2O···O3 | 1.12 (6) | 1.44 (6) | 2.488 (4) | 153 (4) |
N2—H2N···O1 | 0.92 (4) | 1.76 (5) | 2.619 (4) | 153 (4) |
| | | | |
Monoclinic polymorph 1m | | | | |
O2A—H2OA···O3A | 1.18 (2) | 1.28 (2) | 2.4571 (18) | 175.3 (19) |
O2B—H2OB···O3B | 1.06 (3) | 1.46 (3) | 2.4579 (19) | 155 (3) |
N2A—H2NA···O1A | 1.060 (19) | 1.669 (19) | 2.6314 (19) | 148.4 (16) |
N2B—H2NB···O1B | 0.84 (2) | 1.87 (2) | 2.629 (2) | 149 (2) |
Symmetry codes, interaction energy of the basic molecule with neighbouring
ones (Eint) with the highest values (more than 5% of total
interaction energy) and the contribution of this energy to the total
interaction energy (%) in 1t crystals (for full list of dimers see
Tables S1 in the supporting information) topDimer | Symmetry operation | Eint (kcal mol-1) | Contribution to the total interaction energy (%) |
1t_d1 | -x+1, -y+1, -z+1 | -24.1 | 26.3 |
1t_d2 | -x+2, -y+1, -z+1 | -25.2 | 27.6 |
1t_d3 | -x+1, -y+1, -z+2 | -6.1 | 6.7 |
1t_d4 | -x+1, -y+2, -z+1 | -6.2 | 6.8 |
Symmetry codes, interaction energy of the basic molecule with neighbouring
ones (Eint) with the highest values (more than 5% of total
interaction energy) and the contribution of this energy to the total
interaction energy (%) in 1m crystals (for full list of dimers see
Table S2 in the supporting information) topDimer | Molecules | Symmetry operation | Eint (kcal mol-1) | Contribution to the total interaction energy (%) |
Molecule 1A | | | | |
1m_d1 | 1A-1B | -x+1, -y+1, -z+1 | -23.0 | 27.0 |
1m_d2 | 1A-1A | -x+1, -y+1, -z+1 | -16.2 | 19.0 |
1m_d3 | 1A-1B | x+1, y, z | -7.2 | 8.4 |
1m_d4 | 1A-1B | -x+1, -y+2, -z+1 | -6.6 | 7.7 |
1m_d5 | 1A-1B | x, y-1, z | -5.7 | 6.7 |
1m_d6 | 1A-1A | x+1/2, -y+1/2, z+1/2 | -5.0 | 5.9 |
1m_d7 | 1A-1A | x-1/2, -y+1/2, z-1/2 | -5.0 | 5.9 |
| | | | |
Molecule 1B | | | | |
1m_d16 | 1B-1B | -x, -y+2, -z+1 | -24.6 | 26.6 |
1m_d17 | 1B-1A | -x+1, -y+1, -z+1 | -23.0 | 24.9 |
1m_d18 | 1B-1A | x-1, y, z | -7.2 | 7.8 |
1m_d19 | 1B-1A | -x+1, -y+2, -z+1 | -6.6 | 7.1 |
1m_d20 | 1B-1A | x, y+1, z | -5.7 | 6.2 |
Results of DSC analysis topStructure | Heating rate (°C min-1) | Melting point, Tonset (°C) | Melting point, Tpeak (°C) |
Polymorph 1m | 5 | 199.2 | 199.9 |
| 10 | 199.4 | 200.4 |
Polymorph 1t | 5 | 202.2 | 203.5 |
| 10 | 201.9 | 203.4 |
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