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6-Hy­droxy-N-(4-meth­oxy­phen­yl)-4-oxo-2,4-di­hydro-1H-pyrrolo­[3,2,1-ij]quinoline-5-carboxamide, C19H16N2O4, 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\overline{1}), with one mol­ecule in the asymmetric unit, and the monoclinic polymorph (space group P21/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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618016352/jx3022sup1.cif
Contains datablocks 1m, 1t, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618016352/jx30221msup2.hkl
Contains datablock 1m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618016352/jx30221tsup3.hkl
Contains datablock 1t

CCDC references: 1863529; 1863530

Computing details top

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-1H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide (1m) top
Crystal data top
C19H16N2O4F(000) = 1408
Mr = 336.34Dx = 1.439 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 16.3612 (6) ÅCell parameters from 4692 reflections
b = 8.4646 (3) Åθ = 3.4–29.2°
c = 23.6668 (12) ŵ = 0.10 mm1
β = 108.718 (5)°T = 293 K
V = 3104.3 (2) Å3Parallelepiped, colourless
Z = 80.20 × 0.10 × 0.10 mm
Data collection top
Agilent Xcalibur Sapphire3
diffractometer
9030 independent reflections
Radiation source: Enhance (Mo) X-ray Source5185 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm-1Rint = 0.039
ω–scanθmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
h = 2323
Tmin = 0.936, Tmax = 1.000k = 1111
34873 measured reflectionsl = 3332
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.059H 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 reflectionsΔρmax = 0.43 e Å3
469 parametersΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
O1A0.74686 (8)0.49626 (16)0.48665 (6)0.0587 (3)
O2A0.70068 (8)0.14666 (16)0.63233 (6)0.0622 (4)
H2OA0.6448 (13)0.168 (2)0.5870 (10)0.072 (6)*
O3A0.58038 (8)0.19520 (16)0.54028 (6)0.0611 (3)
O4A0.26835 (8)0.42695 (18)0.30262 (6)0.0681 (4)
N1A0.85249 (8)0.44630 (16)0.57365 (6)0.0436 (3)
N2A0.59387 (9)0.37211 (19)0.47159 (7)0.0526 (4)
H2NA0.6437 (12)0.440 (2)0.4637 (8)0.063 (5)*
C1A0.88220 (10)0.37660 (19)0.62850 (7)0.0425 (4)
C2A0.96700 (11)0.4234 (2)0.65878 (9)0.0515 (4)
C3A1.00424 (12)0.3636 (2)0.71434 (9)0.0599 (5)
H3A1.0604390.3917570.7362140.072*
C4A0.95778 (13)0.2587 (3)0.73894 (9)0.0654 (5)
H4A0.9840810.2190740.7771340.078*
C5A0.87500 (12)0.2133 (2)0.70817 (8)0.0558 (5)
H5A0.8458240.1430240.7250870.067*
C6A0.83457 (10)0.2749 (2)0.65042 (8)0.0463 (4)
C7A0.74839 (11)0.2460 (2)0.61244 (8)0.0463 (4)
C8A0.71632 (10)0.3204 (2)0.55778 (8)0.0443 (4)
C9A0.77049 (10)0.4271 (2)0.53587 (7)0.0443 (4)
C10A0.91971 (11)0.5454 (2)0.56190 (8)0.0515 (4)
H10A0.9002490.6537490.5536620.062*
H10B0.9351600.5048180.5283520.062*
C11A0.99610 (11)0.5344 (2)0.61976 (9)0.0574 (5)
H11A1.0468280.4935120.6119720.069*
H11B1.0096430.6373590.6384220.069*
C12A0.62522 (10)0.2913 (2)0.52212 (8)0.0478 (4)
C13A0.50888 (10)0.3741 (2)0.43050 (8)0.0470 (4)
C14A0.44826 (11)0.2568 (2)0.42463 (9)0.0572 (5)
H14A0.4617970.1681490.4490620.069*
C15A0.36672 (11)0.2709 (3)0.38217 (9)0.0584 (5)
H15A0.3258290.1919070.3785890.070*
C16A0.34666 (10)0.4006 (2)0.34573 (8)0.0523 (4)
C17A0.40749 (12)0.5162 (2)0.35083 (9)0.0589 (5)
H17A0.3943520.6036210.3257110.071*
C18A0.48782 (12)0.5031 (2)0.39300 (9)0.0559 (5)
H18A0.5284640.5823600.3962610.067*
C19A0.20382 (13)0.3108 (4)0.29391 (12)0.0920 (8)
H19D0.1533210.3429480.2622120.138*
H19E0.1895880.2979430.3299630.138*
H19F0.2245670.2123970.2836210.138*
O1B0.04148 (7)0.75087 (15)0.52178 (6)0.0547 (3)
O2B0.16469 (10)1.10893 (16)0.41594 (6)0.0629 (4)
H2B0.0997 (19)1.097 (3)0.3881 (12)0.122 (10)*
O3B0.01404 (9)1.02595 (16)0.36929 (6)0.0623 (4)
O4B0.37976 (9)0.77522 (19)0.25318 (6)0.0698 (4)
N1B0.17953 (9)0.82858 (16)0.55953 (6)0.0461 (3)
N2B0.05060 (10)0.85478 (19)0.41577 (7)0.0508 (4)
H2NB0.0395 (14)0.807 (3)0.4485 (10)0.075 (7)*
C1B0.24943 (11)0.91730 (19)0.55775 (8)0.0454 (4)
C2B0.32110 (11)0.8902 (2)0.60702 (8)0.0506 (4)
C3B0.39528 (12)0.9713 (2)0.61031 (10)0.0598 (5)
H3B0.4452690.9555820.6424100.072*
C4B0.39498 (13)1.0772 (2)0.56513 (10)0.0637 (5)
H4B0.4450441.1333670.5680740.076*
C5B0.32319 (13)1.1012 (2)0.51657 (10)0.0593 (5)
H5B0.3249881.1722990.4870430.071*
C6B0.24665 (11)1.0179 (2)0.51143 (8)0.0480 (4)
C7B0.16733 (12)1.02105 (19)0.46283 (8)0.0476 (4)
C8B0.09630 (11)0.93260 (19)0.46489 (8)0.0451 (4)
C9B0.10185 (11)0.83223 (19)0.51611 (8)0.0442 (4)
C10B0.20191 (11)0.7322 (2)0.61391 (8)0.0534 (4)
H10C0.1931260.6207770.6042240.064*
H10D0.1673870.7619140.6387390.064*
C11B0.29861 (12)0.7682 (2)0.64571 (10)0.0629 (5)
H11C0.3076290.8091390.6855340.076*
H11D0.3333350.6738270.6485510.076*
C12B0.01696 (11)0.9412 (2)0.41345 (8)0.0487 (4)
C13B0.13289 (11)0.8364 (2)0.37293 (8)0.0480 (4)
C14B0.15961 (12)0.9098 (2)0.31745 (8)0.0574 (5)
H14B0.1219160.9755000.3062320.069*
C15B0.24170 (12)0.8853 (2)0.27922 (9)0.0597 (5)
H15B0.2589410.9343570.2420990.072*
C16B0.29903 (11)0.7893 (2)0.29486 (8)0.0527 (4)
C17B0.27343 (11)0.7156 (2)0.34979 (8)0.0521 (4)
H17B0.3113930.6500050.3607660.062*
C18B0.19070 (11)0.7402 (2)0.38840 (8)0.0510 (4)
H18B0.1736350.6911190.4255110.061*
C19B0.44396 (13)0.6938 (3)0.26915 (10)0.0739 (6)
H19A0.4965630.6935580.2360540.111*
H19B0.4535410.7453250.3026200.111*
H19C0.4256260.5870210.2796940.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0512 (7)0.0707 (9)0.0502 (8)0.0037 (6)0.0109 (6)0.0115 (6)
O2A0.0534 (7)0.0717 (9)0.0629 (9)0.0112 (7)0.0207 (7)0.0129 (7)
O3A0.0478 (7)0.0727 (9)0.0621 (9)0.0126 (6)0.0163 (6)0.0021 (7)
O4A0.0468 (7)0.0895 (10)0.0583 (9)0.0047 (7)0.0035 (6)0.0025 (7)
N1A0.0387 (7)0.0461 (7)0.0477 (9)0.0031 (6)0.0163 (6)0.0024 (6)
N2A0.0423 (7)0.0629 (9)0.0488 (9)0.0001 (7)0.0094 (7)0.0008 (7)
C1A0.0418 (8)0.0432 (9)0.0409 (9)0.0047 (7)0.0110 (7)0.0019 (7)
C2A0.0436 (9)0.0513 (10)0.0570 (12)0.0002 (8)0.0123 (8)0.0026 (8)
C3A0.0437 (9)0.0690 (12)0.0584 (12)0.0022 (9)0.0046 (9)0.0003 (10)
C4A0.0605 (11)0.0759 (13)0.0510 (12)0.0023 (10)0.0055 (9)0.0105 (10)
C5A0.0570 (10)0.0628 (11)0.0483 (11)0.0000 (9)0.0176 (9)0.0084 (9)
C6A0.0452 (9)0.0507 (9)0.0455 (10)0.0015 (8)0.0180 (8)0.0018 (8)
C7A0.0494 (9)0.0454 (9)0.0502 (11)0.0007 (7)0.0246 (8)0.0002 (8)
C8A0.0368 (8)0.0484 (9)0.0486 (10)0.0023 (7)0.0147 (7)0.0094 (7)
C9A0.0453 (8)0.0471 (9)0.0399 (10)0.0045 (7)0.0131 (7)0.0013 (7)
C10A0.0465 (9)0.0494 (9)0.0616 (12)0.0070 (8)0.0214 (9)0.0005 (8)
C11A0.0471 (9)0.0537 (10)0.0708 (13)0.0080 (8)0.0181 (9)0.0015 (9)
C12A0.0414 (8)0.0535 (10)0.0497 (11)0.0019 (8)0.0162 (8)0.0070 (8)
C13A0.0402 (8)0.0578 (10)0.0424 (10)0.0008 (8)0.0122 (7)0.0075 (8)
C14A0.0472 (9)0.0641 (11)0.0573 (12)0.0014 (9)0.0127 (8)0.0044 (9)
C15A0.0440 (9)0.0732 (13)0.0553 (12)0.0087 (9)0.0123 (8)0.0019 (10)
C16A0.0412 (9)0.0703 (12)0.0435 (10)0.0057 (9)0.0110 (8)0.0094 (9)
C17A0.0588 (11)0.0565 (11)0.0540 (12)0.0049 (9)0.0080 (9)0.0003 (9)
C18A0.0528 (10)0.0523 (10)0.0578 (12)0.0039 (9)0.0109 (9)0.0042 (9)
C19A0.0479 (11)0.133 (2)0.0800 (18)0.0116 (14)0.0009 (11)0.0004 (16)
O1B0.0478 (6)0.0621 (8)0.0530 (8)0.0100 (6)0.0145 (6)0.0083 (6)
O2B0.0735 (9)0.0617 (8)0.0604 (9)0.0073 (7)0.0308 (7)0.0105 (7)
O3B0.0682 (8)0.0669 (8)0.0519 (8)0.0001 (7)0.0194 (7)0.0134 (6)
O4B0.0569 (8)0.0909 (10)0.0530 (9)0.0029 (7)0.0054 (6)0.0048 (7)
N1B0.0475 (7)0.0428 (7)0.0479 (9)0.0048 (6)0.0150 (7)0.0015 (6)
N2B0.0507 (8)0.0577 (9)0.0435 (9)0.0021 (7)0.0146 (7)0.0050 (7)
C1B0.0499 (9)0.0378 (8)0.0535 (11)0.0055 (7)0.0233 (8)0.0089 (7)
C2B0.0495 (9)0.0471 (9)0.0562 (11)0.0033 (8)0.0184 (8)0.0080 (8)
C3B0.0505 (10)0.0610 (11)0.0671 (13)0.0086 (9)0.0180 (9)0.0162 (10)
C4B0.0567 (11)0.0626 (12)0.0784 (15)0.0167 (10)0.0312 (11)0.0163 (11)
C5B0.0663 (12)0.0536 (11)0.0696 (14)0.0120 (9)0.0378 (11)0.0068 (9)
C6B0.0546 (10)0.0419 (9)0.0545 (11)0.0050 (8)0.0274 (9)0.0074 (8)
C7B0.0598 (10)0.0394 (8)0.0513 (11)0.0015 (8)0.0287 (9)0.0005 (7)
C8B0.0520 (9)0.0405 (8)0.0476 (10)0.0014 (7)0.0227 (8)0.0011 (7)
C9B0.0467 (9)0.0419 (8)0.0470 (10)0.0017 (7)0.0193 (8)0.0031 (7)
C10B0.0553 (10)0.0528 (10)0.0479 (11)0.0080 (8)0.0107 (8)0.0054 (8)
C11B0.0541 (10)0.0645 (12)0.0615 (13)0.0078 (9)0.0063 (9)0.0046 (10)
C12B0.0569 (10)0.0460 (9)0.0473 (11)0.0049 (8)0.0223 (8)0.0022 (8)
C13B0.0506 (9)0.0495 (9)0.0456 (10)0.0086 (8)0.0177 (8)0.0005 (8)
C14B0.0599 (11)0.0684 (12)0.0468 (11)0.0011 (10)0.0211 (9)0.0050 (9)
C15B0.0648 (11)0.0707 (13)0.0437 (11)0.0078 (10)0.0177 (9)0.0074 (9)
C16B0.0516 (10)0.0573 (10)0.0474 (11)0.0080 (9)0.0134 (8)0.0048 (8)
C17B0.0518 (10)0.0502 (10)0.0540 (11)0.0046 (8)0.0166 (9)0.0026 (8)
C18B0.0563 (10)0.0505 (10)0.0454 (11)0.0091 (8)0.0151 (8)0.0043 (8)
C19B0.0570 (11)0.0972 (17)0.0632 (14)0.0075 (12)0.0133 (10)0.0110 (12)
Geometric parameters (Å, º) top
O1A—C9A1.249 (2)O1B—C9B1.2461 (19)
O2A—C7A1.332 (2)O2B—C7B1.325 (2)
O3A—C12A1.260 (2)O3B—C12B1.256 (2)
O4A—C16A1.376 (2)O4B—C16B1.377 (2)
O4A—C19A1.408 (3)O4B—C19B1.406 (3)
N1A—C9A1.362 (2)N1B—C9B1.354 (2)
N1A—C1A1.365 (2)N1B—C1B1.380 (2)
N1A—C10A1.479 (2)N1B—C10B1.468 (2)
N2A—C12A1.330 (2)N2B—C12B1.341 (2)
N2A—C13A1.418 (2)N2B—C13B1.410 (2)
C1A—C6A1.370 (2)C1B—C6B1.377 (2)
C1A—C2A1.399 (2)C1B—C2B1.382 (2)
C2A—C3A1.358 (3)C2B—C3B1.374 (2)
C2A—C11A1.498 (3)C2B—C11B1.502 (3)
C3A—C4A1.410 (3)C3B—C4B1.394 (3)
C4A—C5A1.371 (3)C4B—C5B1.369 (3)
C5A—C6A1.413 (3)C5B—C6B1.408 (2)
C6A—C7A1.429 (2)C6B—C7B1.432 (3)
C7A—C8A1.382 (2)C7B—C8B1.396 (2)
C8A—C9A1.472 (2)C8B—C9B1.459 (2)
C8A—C12A1.479 (2)C8B—C12B1.469 (3)
C10A—C11A1.532 (3)C10B—C11B1.549 (2)
C13A—C14A1.378 (2)C13B—C18B1.383 (2)
C13A—C18A1.379 (3)C13B—C14B1.390 (2)
C14A—C15A1.394 (3)C14B—C15B1.373 (3)
C15A—C16A1.369 (3)C15B—C16B1.379 (3)
C16A—C17A1.373 (3)C16B—C17B1.380 (3)
C17A—C18A1.376 (3)C17B—C18B1.384 (2)
C16A—O4A—C19A118.10 (17)C16B—O4B—C19B118.52 (16)
C9A—N1A—C1A123.21 (14)C9B—N1B—C1B123.34 (15)
C9A—N1A—C10A125.40 (14)C9B—N1B—C10B125.96 (14)
C1A—N1A—C10A111.38 (13)C1B—N1B—C10B110.69 (14)
C12A—N2A—C13A129.29 (16)C12B—N2B—C13B129.78 (17)
N1A—C1A—C6A124.00 (15)C6B—C1B—N1B123.00 (16)
N1A—C1A—C2A110.89 (15)C6B—C1B—C2B125.20 (16)
C6A—C1A—C2A125.11 (16)N1B—C1B—C2B111.79 (15)
C3A—C2A—C1A116.96 (17)C3B—C2B—C1B117.37 (17)
C3A—C2A—C11A134.32 (16)C3B—C2B—C11B133.89 (18)
C1A—C2A—C11A108.72 (16)C1B—C2B—C11B108.71 (15)
C2A—C3A—C4A120.07 (17)C2B—C3B—C4B119.47 (19)
C5A—C4A—C3A121.91 (19)C5B—C4B—C3B121.99 (18)
C4A—C5A—C6A119.12 (18)C4B—C5B—C6B119.87 (19)
C1A—C6A—C5A116.83 (16)C1B—C6B—C5B116.07 (18)
C1A—C6A—C7A115.82 (16)C1B—C6B—C7B116.16 (15)
C5A—C6A—C7A127.33 (16)C5B—C6B—C7B127.73 (17)
O2A—C7A—C8A121.93 (16)O2B—C7B—C8B121.76 (17)
O2A—C7A—C6A117.23 (16)O2B—C7B—C6B117.44 (16)
C8A—C7A—C6A120.84 (15)C8B—C7B—C6B120.79 (16)
C7A—C8A—C9A121.26 (15)C7B—C8B—C9B120.71 (16)
C7A—C8A—C12A117.96 (15)C7B—C8B—C12B117.93 (16)
C9A—C8A—C12A120.78 (16)C9B—C8B—C12B121.35 (15)
O1A—C9A—N1A120.08 (15)O1B—C9B—N1B119.28 (15)
O1A—C9A—C8A125.12 (15)O1B—C9B—C8B124.83 (16)
N1A—C9A—C8A114.79 (15)N1B—C9B—C8B115.89 (14)
N1A—C10A—C11A103.89 (14)N1B—C10B—C11B104.19 (14)
C2A—C11A—C10A105.05 (14)C2B—C11B—C10B104.54 (15)
O3A—C12A—N2A122.71 (16)O3B—C12B—N2B122.27 (17)
O3A—C12A—C8A120.23 (17)O3B—C12B—C8B120.37 (16)
N2A—C12A—C8A117.05 (16)N2B—C12B—C8B117.36 (16)
C14A—C13A—C18A118.83 (16)C18B—C13B—C14B118.59 (17)
C14A—C13A—N2A125.16 (17)C18B—C13B—N2B116.78 (16)
C18A—C13A—N2A115.99 (16)C14B—C13B—N2B124.62 (17)
C13A—C14A—C15A120.17 (18)C15B—C14B—C13B119.95 (18)
C16A—C15A—C14A120.18 (18)C14B—C15B—C16B121.21 (18)
C15A—C16A—C17A119.72 (17)O4B—C16B—C15B115.94 (17)
C15A—C16A—O4A125.10 (17)O4B—C16B—C17B124.56 (17)
C17A—C16A—O4A115.18 (18)C15B—C16B—C17B119.50 (17)
C16A—C17A—C18A120.19 (18)C16B—C17B—C18B119.37 (18)
C17A—C18A—C13A120.90 (18)C13B—C18B—C17B121.38 (17)
C9A—N1A—C1A—C6A3.0 (2)C9B—N1B—C1B—C6B0.1 (2)
C10A—N1A—C1A—C6A178.04 (15)C10B—N1B—C1B—C6B179.59 (16)
C9A—N1A—C1A—C2A176.87 (15)C9B—N1B—C1B—C2B179.17 (15)
C10A—N1A—C1A—C2A2.08 (19)C10B—N1B—C1B—C2B0.6 (2)
N1A—C1A—C2A—C3A179.43 (16)C6B—C1B—C2B—C3B0.7 (3)
C6A—C1A—C2A—C3A0.4 (3)N1B—C1B—C2B—C3B179.66 (15)
N1A—C1A—C2A—C11A0.3 (2)C6B—C1B—C2B—C11B177.65 (17)
C6A—C1A—C2A—C11A179.78 (16)N1B—C1B—C2B—C11B1.4 (2)
C1A—C2A—C3A—C4A0.3 (3)C1B—C2B—C3B—C4B0.9 (3)
C11A—C2A—C3A—C4A180.0 (2)C11B—C2B—C3B—C4B178.7 (2)
C2A—C3A—C4A—C5A0.3 (3)C2B—C3B—C4B—C5B1.4 (3)
C3A—C4A—C5A—C6A0.8 (3)C3B—C4B—C5B—C6B0.3 (3)
N1A—C1A—C6A—C5A179.84 (15)N1B—C1B—C6B—C5B179.42 (15)
C2A—C1A—C6A—C5A0.0 (3)C2B—C1B—C6B—C5B1.7 (3)
N1A—C1A—C6A—C7A1.3 (2)N1B—C1B—C6B—C7B2.7 (2)
C2A—C1A—C6A—C7A178.60 (16)C2B—C1B—C6B—C7B176.18 (16)
C4A—C5A—C6A—C1A0.6 (3)C4B—C5B—C6B—C1B1.2 (3)
C4A—C5A—C6A—C7A177.81 (18)C4B—C5B—C6B—C7B176.40 (18)
C1A—C6A—C7A—O2A179.50 (15)C1B—C6B—C7B—O2B175.72 (14)
C5A—C6A—C7A—O2A2.1 (3)C5B—C6B—C7B—O2B1.9 (3)
C1A—C6A—C7A—C8A1.3 (2)C1B—C6B—C7B—C8B3.4 (2)
C5A—C6A—C7A—C8A177.14 (17)C5B—C6B—C7B—C8B179.08 (16)
O2A—C7A—C8A—C9A178.63 (15)O2B—C7B—C8B—C9B177.73 (15)
C6A—C7A—C8A—C9A2.2 (2)C6B—C7B—C8B—C9B1.3 (2)
O2A—C7A—C8A—C12A2.2 (2)O2B—C7B—C8B—C12B0.9 (2)
C6A—C7A—C8A—C12A176.96 (15)C6B—C7B—C8B—C12B179.92 (15)
C1A—N1A—C9A—O1A178.83 (15)C1B—N1B—C9B—O1B178.48 (14)
C10A—N1A—C9A—O1A0.0 (3)C10B—N1B—C9B—O1B1.8 (3)
C1A—N1A—C9A—C8A2.0 (2)C1B—N1B—C9B—C8B2.3 (2)
C10A—N1A—C9A—C8A179.25 (14)C10B—N1B—C9B—C8B177.40 (15)
C7A—C8A—C9A—O1A178.60 (16)C7B—C8B—C9B—O1B179.28 (15)
C12A—C8A—C9A—O1A2.3 (3)C12B—C8B—C9B—O1B2.1 (3)
C7A—C8A—C9A—N1A0.6 (2)C7B—C8B—C9B—N1B1.5 (2)
C12A—C8A—C9A—N1A178.55 (14)C12B—C8B—C9B—N1B177.04 (14)
C9A—N1A—C10A—C11A176.08 (15)C9B—N1B—C10B—C11B177.59 (16)
C1A—N1A—C10A—C11A2.84 (19)C1B—N1B—C10B—C11B2.13 (19)
C3A—C2A—C11A—C10A178.9 (2)C3B—C2B—C11B—C10B179.5 (2)
C1A—C2A—C11A—C10A1.4 (2)C1B—C2B—C11B—C10B2.6 (2)
N1A—C10A—C11A—C2A2.46 (18)N1B—C10B—C11B—C2B2.8 (2)
C13A—N2A—C12A—O3A2.4 (3)C13B—N2B—C12B—O3B1.5 (3)
C13A—N2A—C12A—C8A176.59 (16)C13B—N2B—C12B—C8B177.99 (16)
C7A—C8A—C12A—O3A3.5 (2)C7B—C8B—C12B—O3B0.0 (2)
C9A—C8A—C12A—O3A177.37 (15)C9B—C8B—C12B—O3B178.61 (15)
C7A—C8A—C12A—N2A175.53 (15)C7B—C8B—C12B—N2B179.51 (15)
C9A—C8A—C12A—N2A3.6 (2)C9B—C8B—C12B—N2B0.9 (2)
C12A—N2A—C13A—C14A21.9 (3)C12B—N2B—C13B—C18B178.96 (16)
C12A—N2A—C13A—C18A159.89 (18)C12B—N2B—C13B—C14B0.1 (3)
C18A—C13A—C14A—C15A1.2 (3)C18B—C13B—C14B—C15B0.4 (3)
N2A—C13A—C14A—C15A179.40 (17)N2B—C13B—C14B—C15B179.26 (17)
C13A—C14A—C15A—C16A0.6 (3)C13B—C14B—C15B—C16B0.4 (3)
C14A—C15A—C16A—C17A0.6 (3)C19B—O4B—C16B—C15B172.82 (18)
C14A—C15A—C16A—O4A179.67 (17)C19B—O4B—C16B—C17B6.8 (3)
C19A—O4A—C16A—C15A1.5 (3)C14B—C15B—C16B—O4B179.23 (18)
C19A—O4A—C16A—C17A178.27 (19)C14B—C15B—C16B—C17B0.4 (3)
C15A—C16A—C17A—C18A1.0 (3)O4B—C16B—C17B—C18B179.18 (17)
O4A—C16A—C17A—C18A179.19 (17)C15B—C16B—C17B—C18B0.4 (3)
C16A—C17A—C18A—C13A0.4 (3)C14B—C13B—C18B—C17B0.4 (3)
C14A—C13A—C18A—C17A0.7 (3)N2B—C13B—C18B—C17B179.38 (16)
N2A—C13A—C18A—C17A179.11 (17)C16B—C17B—C18B—C13B0.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2OA···O3A1.18 (2)1.28 (2)2.4571 (18)175.3 (19)
O2B—H2B···O3B1.06 (3)1.46 (3)2.4579 (19)155 (3)
N2A—H2NA···O1A1.060 (19)1.669 (19)2.6314 (19)148.4 (16)
N2B—H2NB···O1B0.84 (2)1.87 (2)2.629 (2)149 (2)
6-Hydroxy-N-(4-methoxyphenyl)-4-oxo-2,4-dihydro-1H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide (1t) top
Crystal data top
C19H16N2O4Z = 2
Mr = 336.34F(000) = 352
Triclinic, P1Dx = 1.450 Mg m3
a = 7.1048 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0882 (16) ÅCell parameters from 568 reflections
c = 11.5171 (17) Åθ = 3.7–23.0°
α = 73.761 (17)°µ = 0.10 mm1
β = 87.27 (2)°T = 293 K
γ = 76.48 (2)°Stick, colourless
V = 770.4 (3) Å30.20 × 0.05 × 0.04 mm
Data collection top
Agilent Xcalibur Sapphire3
diffractometer
2718 independent reflections
Radiation source: Enhance (Mo) X-ray Source1417 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm-1Rint = 0.052
ω–scanθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
h = 88
Tmin = 0.149, Tmax = 1.000k = 1111
5035 measured reflectionsl = 1313
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.088H 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 reflectionsΔρmax = 0.39 e Å3
235 parametersΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
O10.6158 (4)0.7240 (3)0.4080 (2)0.0554 (9)
O20.8627 (5)0.2542 (3)0.6600 (3)0.0565 (9)
H2O0.785 (8)0.312 (5)0.725 (4)0.089 (16)*
O30.6756 (4)0.4363 (3)0.7553 (2)0.0541 (9)
O40.2556 (5)0.9886 (3)0.9527 (3)0.0738 (11)
N10.7900 (5)0.5530 (3)0.3314 (3)0.0469 (9)
N20.5565 (5)0.6629 (4)0.6413 (3)0.0466 (9)
H2N0.557 (6)0.711 (5)0.561 (4)0.065 (14)*
C10.8900 (6)0.4165 (4)0.3412 (4)0.0432 (10)
C20.9568 (6)0.3965 (4)0.2307 (4)0.0500 (11)
C31.0568 (7)0.2640 (5)0.2304 (4)0.0597 (13)
H31.1028700.2462770.1579880.072*
C41.0913 (7)0.1533 (5)0.3385 (4)0.0601 (13)
H41.1591020.0631090.3367120.072*
C51.0253 (6)0.1776 (4)0.4473 (4)0.0519 (12)
H51.0517230.1042930.5184960.062*
C60.9196 (6)0.3112 (4)0.4507 (4)0.0430 (10)
C70.8368 (6)0.3535 (4)0.5539 (4)0.0428 (10)
C80.7325 (6)0.4912 (4)0.5436 (3)0.0406 (10)
C90.7060 (6)0.5986 (4)0.4267 (4)0.0441 (10)
C100.7814 (7)0.6378 (5)0.2042 (4)0.0578 (12)
H10A0.8386590.7183670.1954020.069*
H10B0.6484980.6721790.1745200.069*
C110.8970 (7)0.5370 (5)0.1355 (4)0.0571 (12)
H11A0.8176150.5289970.0726980.069*
H11B1.0095390.5698050.0989090.069*
C120.6530 (6)0.5287 (4)0.6541 (4)0.0437 (10)
C130.4783 (6)0.7331 (4)0.7283 (4)0.0450 (10)
C140.4725 (6)0.6697 (4)0.8512 (4)0.0493 (11)
H140.5182960.5722380.8819990.059*
C150.3972 (7)0.7532 (5)0.9289 (4)0.0524 (12)
H150.3932620.7104601.0114580.063*
C160.3290 (6)0.8972 (4)0.8850 (4)0.0512 (11)
C170.3343 (7)0.9597 (5)0.7615 (4)0.0608 (13)
H170.2880181.0571370.7305530.073*
C180.4075 (7)0.8786 (4)0.6849 (4)0.0540 (12)
H180.4096650.9219380.6023020.065*
C190.2421 (9)0.9307 (6)1.0795 (4)0.0862 (18)
H19A0.1739701.0037411.1145800.129*
H19B0.3697880.8928471.1148850.129*
H19C0.1733140.8563481.0946710.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.070 (2)0.0416 (18)0.0480 (18)0.0032 (15)0.0050 (15)0.0103 (14)
O20.069 (2)0.0414 (17)0.0489 (18)0.0042 (15)0.0029 (15)0.0043 (14)
O30.069 (2)0.0446 (17)0.0426 (17)0.0066 (15)0.0072 (14)0.0085 (14)
O40.111 (3)0.0524 (19)0.051 (2)0.0009 (18)0.0165 (18)0.0198 (16)
N10.056 (2)0.046 (2)0.0363 (19)0.0090 (17)0.0021 (16)0.0100 (16)
N20.055 (2)0.046 (2)0.038 (2)0.0065 (17)0.0080 (17)0.0147 (17)
C10.042 (3)0.047 (2)0.044 (2)0.0117 (19)0.0022 (19)0.018 (2)
C20.050 (3)0.053 (3)0.052 (3)0.012 (2)0.007 (2)0.024 (2)
C30.059 (3)0.066 (3)0.064 (3)0.015 (2)0.018 (2)0.038 (3)
C40.061 (3)0.051 (3)0.073 (3)0.012 (2)0.014 (3)0.027 (3)
C50.057 (3)0.041 (2)0.060 (3)0.013 (2)0.006 (2)0.016 (2)
C60.043 (2)0.040 (2)0.049 (2)0.0086 (19)0.0025 (19)0.0167 (19)
C70.040 (2)0.044 (2)0.044 (2)0.0109 (19)0.0004 (18)0.0101 (19)
C80.043 (2)0.042 (2)0.040 (2)0.0115 (19)0.0064 (18)0.0150 (18)
C90.050 (3)0.045 (3)0.039 (2)0.012 (2)0.0042 (19)0.0138 (19)
C100.066 (3)0.061 (3)0.043 (3)0.010 (2)0.009 (2)0.014 (2)
C110.063 (3)0.066 (3)0.043 (2)0.015 (2)0.005 (2)0.015 (2)
C120.047 (3)0.045 (2)0.040 (2)0.012 (2)0.0005 (19)0.0119 (19)
C130.045 (3)0.046 (2)0.044 (2)0.008 (2)0.0045 (19)0.0157 (19)
C140.058 (3)0.040 (2)0.049 (3)0.008 (2)0.006 (2)0.013 (2)
C150.064 (3)0.055 (3)0.037 (2)0.012 (2)0.004 (2)0.012 (2)
C160.060 (3)0.046 (3)0.046 (3)0.004 (2)0.006 (2)0.017 (2)
C170.080 (4)0.038 (2)0.055 (3)0.001 (2)0.008 (2)0.008 (2)
C180.065 (3)0.048 (3)0.040 (2)0.006 (2)0.008 (2)0.006 (2)
C190.122 (5)0.076 (4)0.048 (3)0.009 (3)0.007 (3)0.024 (3)
Geometric parameters (Å, º) top
O1—C91.241 (5)C6—C71.429 (6)
O2—C71.335 (5)C7—C81.388 (6)
O2—H2O1.12 (6)C8—C91.461 (5)
O3—C121.263 (4)C8—C121.477 (6)
O3—H2O1.44 (6)C10—C111.527 (7)
O4—C161.368 (5)C10—H10A0.9700
O4—C191.420 (6)C10—H10B0.9700
N1—C91.365 (5)C11—H11A0.9700
N1—C11.370 (5)C11—H11B0.9700
N1—C101.471 (5)C13—C141.384 (6)
N2—C121.337 (5)C13—C181.388 (6)
N2—C131.405 (5)C14—C151.401 (6)
N2—H2N0.92 (4)C14—H140.9300
C1—C21.388 (6)C15—C161.373 (6)
C1—C61.391 (5)C15—H150.9300
C2—C31.360 (6)C16—C171.388 (6)
C2—C111.511 (6)C17—C181.371 (6)
C3—C41.407 (6)C17—H170.9300
C3—H30.9300C18—H180.9300
C4—C51.383 (6)C19—H19A0.9600
C4—H40.9300C19—H19B0.9600
C5—C61.392 (6)C19—H19C0.9600
C5—H50.9300
C7—O2—H2O103 (3)C11—C10—H10A110.7
C12—O3—H2O103 (2)N1—C10—H10B110.7
C16—O4—C19117.9 (4)C11—C10—H10B110.7
C9—N1—C1123.8 (3)H10A—C10—H10B108.8
C9—N1—C10126.4 (3)C2—C11—C10104.5 (3)
C1—N1—C10109.8 (3)C2—C11—H11A110.8
C12—N2—C13130.6 (4)C10—C11—H11A110.8
C12—N2—H2N108 (3)C2—C11—H11B110.8
C13—N2—H2N121 (3)C10—C11—H11B110.8
N1—C1—C2112.5 (3)H11A—C11—H11B108.9
N1—C1—C6122.9 (4)O3—C12—N2122.4 (4)
C2—C1—C6124.6 (4)O3—C12—C8120.5 (4)
C3—C2—C1117.1 (4)N2—C12—C8117.1 (3)
C3—C2—C11135.0 (4)C14—C13—C18118.8 (4)
C1—C2—C11107.8 (4)C14—C13—N2125.4 (4)
C2—C3—C4120.8 (4)C18—C13—N2115.7 (4)
C2—C3—H3119.6C13—C14—C15119.6 (4)
C4—C3—H3119.6C13—C14—H14120.2
C5—C4—C3120.5 (4)C15—C14—H14120.2
C5—C4—H4119.7C16—C15—C14121.0 (4)
C3—C4—H4119.7C16—C15—H15119.5
C4—C5—C6120.3 (4)C14—C15—H15119.5
C4—C5—H5119.9O4—C16—C15125.8 (4)
C6—C5—H5119.9O4—C16—C17115.2 (4)
C1—C6—C5116.7 (4)C15—C16—C17119.0 (4)
C1—C6—C7115.8 (4)C18—C17—C16120.3 (4)
C5—C6—C7127.6 (4)C18—C17—H17119.8
O2—C7—C8121.8 (4)C16—C17—H17119.8
O2—C7—C6116.9 (4)C17—C18—C13121.2 (4)
C8—C7—C6121.3 (3)C17—C18—H18119.4
C7—C8—C9121.0 (4)C13—C18—H18119.4
C7—C8—C12118.6 (3)O4—C19—H19A109.5
C9—C8—C12120.3 (4)O4—C19—H19B109.5
O1—C9—N1118.9 (4)H19A—C19—H19B109.5
O1—C9—C8125.9 (4)O4—C19—H19C109.5
N1—C9—C8115.2 (4)H19A—C19—H19C109.5
N1—C10—C11105.2 (3)H19B—C19—H19C109.5
N1—C10—H10A110.7
C9—N1—C1—C2178.4 (4)C7—C8—C9—O1180.0 (4)
C10—N1—C1—C20.8 (5)C12—C8—C9—O11.7 (6)
C9—N1—C1—C61.5 (6)C7—C8—C9—N10.1 (6)
C10—N1—C1—C6179.2 (4)C12—C8—C9—N1178.3 (3)
N1—C1—C2—C3179.5 (4)C9—N1—C10—C11179.7 (4)
C6—C1—C2—C30.5 (6)C1—N1—C10—C112.1 (5)
N1—C1—C2—C110.9 (5)C3—C2—C11—C10178.3 (5)
C6—C1—C2—C11179.1 (4)C1—C2—C11—C102.1 (5)
C1—C2—C3—C40.6 (6)N1—C10—C11—C22.5 (5)
C11—C2—C3—C4178.9 (5)C13—N2—C12—O36.1 (7)
C2—C3—C4—C50.5 (7)C13—N2—C12—C8174.4 (4)
C3—C4—C5—C61.6 (7)C7—C8—C12—O31.7 (6)
N1—C1—C6—C5179.5 (4)C9—C8—C12—O3180.0 (3)
C2—C1—C6—C50.6 (6)C7—C8—C12—N2178.8 (3)
N1—C1—C6—C70.6 (6)C9—C8—C12—N20.5 (6)
C2—C1—C6—C7179.3 (4)C12—N2—C13—C145.9 (7)
C4—C5—C6—C11.6 (6)C12—N2—C13—C18172.1 (4)
C4—C5—C6—C7178.3 (4)C18—C13—C14—C150.5 (6)
C1—C6—C7—O2179.8 (3)N2—C13—C14—C15177.4 (4)
C5—C6—C7—O20.1 (6)C13—C14—C15—C160.0 (7)
C1—C6—C7—C80.5 (6)C19—O4—C16—C152.1 (7)
C5—C6—C7—C8179.4 (4)C19—O4—C16—C17178.5 (4)
O2—C7—C8—C9179.9 (4)C14—C15—C16—O4178.9 (4)
C6—C7—C8—C90.9 (6)C14—C15—C16—C170.4 (7)
O2—C7—C8—C121.6 (6)O4—C16—C17—C18179.1 (4)
C6—C7—C8—C12179.1 (3)C15—C16—C17—C180.3 (7)
C1—N1—C9—O1178.9 (3)C16—C17—C18—C130.2 (7)
C10—N1—C9—O11.6 (6)C14—C13—C18—C170.6 (7)
C1—N1—C9—C81.1 (6)N2—C13—C18—C17177.5 (4)
C10—N1—C9—C8178.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O31.12 (6)1.44 (6)2.488 (4)153 (4)
N2—H2N···O10.92 (4)1.76 (5)2.619 (4)153 (4)
Results of crystallization from different solvents top
SolventCrystal formStructure
MethanolStick-like1t
EthanolPrismatic1m
Ethyl acetatePrismatic1m
Acetic acidPlate-likeSolvate with acetic acid
DioxaneStick-likeSolvate with dioxane
N,N-DimethylformamidePrismatic1m
Selected geometric parameters for molecule 1 in the triclinic and monoclinic polymorphic forms top
ParameterPolymorph 1tPolymorph 1m
Molecule 1AMolecule 1B
The mean plane of tricyclic fragment and carbamide group (Å)
0.010.040.04
Bond lengths (Å)
C9—O11.241 (5)1.249 (2)1.246 (2)
C12—O31.262 (4)1.260 (2)1.256 (2)
C7—C81.388 (5)1.382 (2)1.396 (3)
C7—O21.335 (5)1.332 (2)1.325 (2)
Torsion angles (°)
O3—C12—N2—C136.0 (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 top
D—H···AD—HH···AD···AD—H···A
Triclinic polymorph 1t
O2—H2O···O31.12 (6)1.44 (6)2.488 (4)153 (4)
N2—H2N···O10.92 (4)1.76 (5)2.619 (4)153 (4)
Monoclinic polymorph 1m
O2A—H2OA···O3A1.18 (2)1.28 (2)2.4571 (18)175.3 (19)
O2B—H2OB···O3B1.06 (3)1.46 (3)2.4579 (19)155 (3)
N2A—H2NA···O1A1.060 (19)1.669 (19)2.6314 (19)148.4 (16)
N2B—H2NB···O1B0.84 (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) top
DimerSymmetry operationEint (kcal mol-1)Contribution to the total interaction energy (%)
1t_d1-x+1, -y+1, -z+1-24.126.3
1t_d2-x+2, -y+1, -z+1-25.227.6
1t_d3-x+1, -y+1, -z+2-6.16.7
1t_d4-x+1, -y+2, -z+1-6.26.8
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) top
DimerMoleculesSymmetry operationEint (kcal mol-1)Contribution to the total interaction energy (%)
Molecule 1A
1m_d11A-1B-x+1, -y+1, -z+1-23.027.0
1m_d21A-1A-x+1, -y+1, -z+1-16.219.0
1m_d31A-1Bx+1, y, z-7.28.4
1m_d41A-1B-x+1, -y+2, -z+1-6.67.7
1m_d51A-1Bx, y-1, z-5.76.7
1m_d61A-1Ax+1/2, -y+1/2, z+1/2-5.05.9
1m_d71A-1Ax-1/2, -y+1/2, z-1/2-5.05.9
Molecule 1B
1m_d161B-1B-x, -y+2, -z+1-24.626.6
1m_d171B-1A-x+1, -y+1, -z+1-23.024.9
1m_d181B-1Ax-1, y, z-7.27.8
1m_d191B-1A-x+1, -y+2, -z+1-6.67.1
1m_d201B-1Ax, y+1, z-5.76.2
Results of DSC analysis top
StructureHeating rate (°C min-1)Melting point, Tonset (°C)Melting point, Tpeak (°C)
Polymorph 1m5199.2199.9
10199.4200.4
Polymorph 1t5202.2203.5
10201.9203.4
 

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