Polymorphic modifications of a 1H-pyrrolo­[3,2,1-ij]quinoline-5-carboxamide possessing strong diuretic properties

Shishkina, S.V.; Levandovskiy, I.A.; Ukrainets, I.V.; Sidorenko, L.V.; Grinevich, L.A.; Yanchuk, I.B.

doi:10.1107/S2053229618016352

Polymorphic modifications of a 1H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide possessing strong diuretic properties

S. V. Shishkina, I. A. Levandovskiy, I. V. Ukrainets, L. V. Sidorenko, L. A. Grinevich and I. B. Yanchuk

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.

Keywords: quinoline-5-carboxamide; diuretic properties; crystal structure; polymorphic modifications; pairwise interaction energies.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618016352/jx3022sup1.cif Contains datablocks 1m, 1t, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618016352/jx30221msup2.hkl Contains datablock 1m
	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

C₁₉H₁₆N₂O₄	F(000) = 1408
M_r = 336.34	D_x = 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	R_int = 0.039
ω–scan	θ_max = 30.0°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	h = −23→23
T_min = 0.936, T_max = 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(F_o²) + (0.075P)² + 0.1828P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
9030 reflections	Δρ_max = 0.43 e Å⁻³
469 parameters	Δρ_min = −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	U_iso*/U_eq
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-1H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide (1t) top

Crystal data top

C₁₉H₁₆N₂O₄	Z = 2
M_r = 336.34	F(000) = 352
Triclinic, P1	D_x = 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	R_int = 0.052
ω–scan	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	h = −8→8
T_min = 0.149, T_max = 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(F_o²) + (0.1293P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
2718 reflections	Δρ_max = 0.39 e Å⁻³
235 parameters	Δρ_min = −0.23 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 top

Solvent	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 top

Parameter	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 top

D—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 (E_int) 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

Dimer	Symmetry operation	E_int (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 (E_int) 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

Dimer	Molecules	Symmetry operation	E_int (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 top

Structure	Heating rate (°C min^-1)	Melting point, T_onset (°C)	Melting point, T_peak (°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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Polymorphic modifications of a 1H-pyrrolo­[3,2,1-ij]quinoline-5-carboxamide possessing strong diuretic properties

Supporting information

Polymorphic modifications of a 1H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide possessing strong diuretic properties