(Pyridin-2-yl)methyl 2-oxo-1-[(pyridin-2-yl)meth­yl]-1,2-di­hydro­quinoline-4-carboxyl­ate hemihydrate

In the title compound, C₂₂H₁₇N₃O₃·0.5H₂O, the heterocyclic portion of the di­hydro­quinoline moiety is distinctly nonplanar. Two quinoline­carboxyl­ate mol­ecules are associated through hydrogen bonding to a disordered lattice water mol­ecule. These units stack along the a-axis direction assisted by C—H...O and C—H...N hydrogen bonds, as well as C—H...π(ring) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.047
• wR factor = 0.106
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.157 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O4      is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4A     is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4B     is Constrained at        0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2)..        100 % Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   1.50) in Resd. #          2 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         49 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(Pyridin-2-yl)methyl 2-oxo-1-[(pyridin-2-yl)methyl]-1,2-dihydroquinoline-4-carboxylate hemihydrate

Crystal data

C22H17N3O3·0.5H2O	F(000) = 796
Mr = 380.40	Dx = 1.407 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 4.9634 (1) Å	Cell parameters from 7827 reflections
b = 14.0708 (3) Å	θ = 3.4–72.4°
c = 25.7168 (6) Å	µ = 0.80 mm^−1
β = 90.602 (1)°	T = 150 K
V = 1795.94 (7) Å^3	Plate, colourless
Z = 4	0.16 × 0.10 × 0.01 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3502 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2673 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.052
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.4°, θmin = 3.4°
ω scans	h = −6→5
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −15→17
Tmin = 0.86, Tmax = 0.99	l = −31→30
13518 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: difference Fourier map
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.031P)^2 + 0.9731P] where P = (Fo^2 + 2Fc^2)/3
3502 reflections	(Δ/σ)max < 0.001
330 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The lattice water molecule is disordered about the centre of symmetry at 0,1/2,1/2. The associated hydrogen atoms were included as riding contributions with idealized geometry.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.6090 (3)	0.70283 (11)	0.69423 (5)	0.0385 (4)
O2	0.2853 (3)	0.61435 (10)	0.65746 (5)	0.0306 (3)
O3	0.4227 (3)	0.61004 (11)	0.47233 (5)	0.0378 (4)
N1	0.7442 (3)	0.71558 (11)	0.49832 (6)	0.0268 (3)
N2	−0.0427 (3)	0.46214 (12)	0.74963 (6)	0.0317 (4)
N3	0.5118 (3)	0.84261 (13)	0.42986 (6)	0.0376 (4)
C1	0.8541 (4)	0.77580 (13)	0.53640 (7)	0.0262 (4)
C2	1.0459 (4)	0.84395 (15)	0.52284 (8)	0.0355 (5)
H2	1.108 (5)	0.8472 (18)	0.4868 (10)	0.054 (7)*
C3	1.1542 (4)	0.90375 (16)	0.55987 (9)	0.0399 (5)
H3	1.288 (5)	0.9520 (18)	0.5494 (9)	0.050 (7)*
C4	1.0711 (4)	0.89791 (15)	0.61121 (9)	0.0368 (5)
H4	1.143 (5)	0.9417 (17)	0.6375 (9)	0.046 (7)*
C5	0.8819 (4)	0.83122 (14)	0.62528 (8)	0.0310 (4)
H5	0.833 (5)	0.8278 (16)	0.6618 (9)	0.039 (6)*
C6	0.7705 (4)	0.76796 (13)	0.58865 (7)	0.0244 (4)
C7	0.5721 (4)	0.69590 (13)	0.60066 (7)	0.0242 (4)
C8	0.4610 (4)	0.64377 (14)	0.56205 (7)	0.0285 (4)
H8	0.328 (4)	0.5950 (15)	0.5682 (8)	0.035 (6)*
C9	0.5352 (4)	0.65462 (14)	0.50801 (7)	0.0279 (4)
C10	0.4961 (4)	0.67449 (13)	0.65563 (7)	0.0259 (4)
C11	0.2171 (4)	0.58148 (15)	0.70873 (7)	0.0307 (4)
H11A	0.387 (5)	0.5565 (15)	0.7270 (8)	0.036 (6)*
H11B	0.142 (4)	0.6371 (16)	0.7294 (8)	0.037 (6)*
C12	0.0124 (4)	0.50362 (13)	0.70393 (7)	0.0263 (4)
C13	−0.1113 (4)	0.47750 (14)	0.65748 (7)	0.0302 (4)
H13	−0.060 (5)	0.5114 (17)	0.6247 (9)	0.047 (7)*
C14	−0.3031 (4)	0.40591 (15)	0.65822 (8)	0.0358 (5)
H14	−0.389 (5)	0.3878 (18)	0.6266 (10)	0.057 (8)*
C15	−0.3632 (5)	0.36315 (16)	0.70488 (9)	0.0389 (5)
H15	−0.496 (5)	0.3130 (19)	0.7073 (10)	0.057 (8)*
C16	−0.2284 (4)	0.39295 (15)	0.74904 (8)	0.0361 (5)
H16	−0.259 (5)	0.3606 (17)	0.7842 (9)	0.046 (7)*
C17	0.8454 (4)	0.71720 (16)	0.44491 (7)	0.0313 (4)
H17A	1.045 (5)	0.7265 (16)	0.4468 (8)	0.041 (6)*
H17B	0.804 (4)	0.6514 (16)	0.4298 (8)	0.033 (6)*
C18	0.7117 (4)	0.79080 (13)	0.41056 (7)	0.0252 (4)
C19	0.7988 (4)	0.80085 (14)	0.35978 (7)	0.0304 (4)
H19	0.951 (5)	0.7607 (17)	0.3464 (9)	0.045 (7)*
C20	0.6714 (5)	0.86600 (15)	0.32762 (8)	0.0355 (5)
H20	0.728 (5)	0.8726 (17)	0.2904 (10)	0.050 (7)*
C21	0.4628 (4)	0.92012 (14)	0.34694 (8)	0.0317 (4)
H21	0.365 (5)	0.9702 (17)	0.3254 (9)	0.045 (6)*
C22	0.3924 (4)	0.90607 (17)	0.39807 (8)	0.0387 (5)
H22	0.246 (5)	0.9434 (18)	0.4128 (10)	0.056 (7)*
O4	0.0130 (7)	0.4897 (2)	0.46975 (12)	0.0499 (8)	0.5
H4A	0.1557	0.5180	0.4821	0.060*	0.5
H4B	−0.0416	0.4545	0.4954	0.060*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0519 (9)	0.0436 (9)	0.0201 (7)	−0.0178 (7)	0.0006 (6)	−0.0004 (6)
O2	0.0314 (7)	0.0403 (8)	0.0200 (6)	−0.0096 (6)	0.0027 (5)	0.0058 (5)
O3	0.0441 (9)	0.0476 (9)	0.0217 (7)	−0.0048 (7)	−0.0019 (6)	−0.0015 (6)
N1	0.0263 (8)	0.0349 (9)	0.0194 (7)	0.0016 (6)	0.0035 (6)	0.0056 (6)
N2	0.0383 (10)	0.0337 (9)	0.0232 (8)	−0.0068 (7)	0.0044 (7)	0.0033 (7)
N3	0.0335 (9)	0.0522 (11)	0.0274 (9)	0.0121 (8)	0.0095 (7)	0.0120 (8)
C1	0.0251 (9)	0.0290 (10)	0.0245 (9)	0.0037 (7)	0.0018 (7)	0.0043 (7)
C2	0.0334 (11)	0.0394 (12)	0.0338 (11)	−0.0026 (9)	0.0078 (8)	0.0079 (9)
C3	0.0364 (12)	0.0376 (12)	0.0459 (13)	−0.0099 (9)	0.0035 (9)	0.0098 (10)
C4	0.0395 (12)	0.0330 (11)	0.0378 (11)	−0.0087 (9)	0.0000 (9)	0.0017 (9)
C5	0.0343 (11)	0.0284 (10)	0.0303 (10)	−0.0034 (8)	0.0016 (8)	0.0002 (8)
C6	0.0248 (10)	0.0246 (9)	0.0239 (9)	0.0019 (7)	0.0016 (7)	0.0049 (7)
C7	0.0247 (9)	0.0269 (9)	0.0211 (9)	0.0019 (7)	0.0022 (7)	0.0028 (7)
C8	0.0288 (10)	0.0344 (11)	0.0222 (9)	−0.0031 (8)	0.0012 (7)	0.0041 (8)
C9	0.0311 (10)	0.0319 (10)	0.0208 (9)	0.0011 (8)	−0.0001 (7)	0.0029 (8)
C10	0.0289 (10)	0.0252 (9)	0.0237 (9)	−0.0018 (7)	0.0031 (7)	0.0015 (7)
C11	0.0377 (12)	0.0364 (11)	0.0180 (9)	−0.0070 (9)	0.0058 (8)	0.0039 (8)
C12	0.0294 (10)	0.0286 (10)	0.0210 (9)	0.0011 (7)	0.0055 (7)	0.0010 (7)
C13	0.0332 (11)	0.0330 (11)	0.0245 (10)	−0.0002 (8)	0.0035 (8)	−0.0008 (8)
C14	0.0415 (12)	0.0362 (12)	0.0296 (11)	−0.0047 (9)	−0.0021 (9)	−0.0059 (9)
C15	0.0428 (13)	0.0331 (12)	0.0410 (12)	−0.0107 (9)	0.0045 (9)	−0.0018 (9)
C16	0.0444 (12)	0.0332 (11)	0.0309 (11)	−0.0086 (9)	0.0066 (9)	0.0039 (9)
C17	0.0323 (11)	0.0425 (12)	0.0194 (9)	0.0044 (9)	0.0050 (8)	0.0056 (8)
C18	0.0232 (9)	0.0315 (10)	0.0210 (9)	−0.0044 (7)	0.0011 (7)	0.0027 (7)
C19	0.0357 (11)	0.0334 (11)	0.0224 (9)	−0.0029 (8)	0.0054 (8)	0.0001 (8)
C20	0.0495 (13)	0.0355 (11)	0.0215 (9)	−0.0054 (9)	0.0040 (8)	0.0029 (8)
C21	0.0353 (11)	0.0309 (11)	0.0288 (10)	−0.0049 (8)	−0.0026 (8)	0.0057 (8)
C22	0.0348 (12)	0.0475 (13)	0.0339 (11)	0.0085 (10)	0.0054 (9)	0.0108 (10)
O4	0.050 (2)	0.057 (2)	0.0420 (18)	−0.0207 (16)	−0.0022 (15)	0.0030 (15)

Geometric parameters (Å, º)

O1—C10	1.203 (2)	C11—C12	1.498 (3)
O2—C10	1.347 (2)	C11—H11A	1.02 (2)
O2—C11	1.441 (2)	C11—H11B	1.02 (2)
O3—C9	1.240 (2)	C12—C13	1.387 (3)
N1—C9	1.371 (2)	C13—C14	1.386 (3)
N1—C1	1.401 (2)	C13—H13	1.01 (2)
N1—C17	1.468 (2)	C14—C15	1.378 (3)
N2—C16	1.341 (3)	C14—H14	0.95 (3)
N2—C12	1.343 (2)	C15—C16	1.377 (3)
N3—C18	1.331 (2)	C15—H15	0.97 (3)
N3—C22	1.344 (3)	C16—H16	1.03 (2)
C1—C2	1.398 (3)	C17—C18	1.510 (3)
C1—C6	1.415 (2)	C17—H17A	1.00 (2)
C2—C3	1.376 (3)	C17—H17B	1.02 (2)
C2—H2	0.98 (3)	C18—C19	1.387 (2)
C3—C4	1.390 (3)	C19—C20	1.383 (3)
C3—H3	0.99 (3)	C19—H19	1.01 (2)
C4—C5	1.379 (3)	C20—C21	1.382 (3)
C4—H4	0.98 (2)	C20—H20	1.00 (2)
C5—C6	1.405 (3)	C21—C22	1.378 (3)
C5—H5	0.97 (2)	C21—H21	1.02 (2)
C6—C7	1.449 (2)	C22—H22	0.98 (3)
C7—C8	1.348 (3)	O4—O4^i	1.589 (6)
C7—C10	1.498 (2)	O4—H4A	0.8701
C8—C9	1.450 (2)	O4—H4B	0.8700
C8—H8	0.97 (2)
C10—O2—C11	115.06 (14)	H11A—C11—H11B	109.2 (17)
C9—N1—C1	122.76 (15)	N2—C12—C13	123.09 (18)
C9—N1—C17	116.55 (16)	N2—C12—C11	112.95 (16)
C1—N1—C17	120.67 (16)	C13—C12—C11	123.96 (16)
C16—N2—C12	116.89 (17)	C14—C13—C12	118.61 (18)
C18—N3—C22	117.55 (17)	C14—C13—H13	122.5 (14)
C2—C1—N1	120.11 (17)	C12—C13—H13	118.8 (14)
C2—C1—C6	119.83 (18)	C15—C14—C13	118.95 (19)
N1—C1—C6	120.06 (16)	C15—C14—H14	122.0 (16)
C3—C2—C1	120.60 (19)	C13—C14—H14	119.1 (16)
C3—C2—H2	120.1 (15)	C16—C15—C14	118.5 (2)
C1—C2—H2	119.2 (15)	C16—C15—H15	119.6 (15)
C2—C3—C4	120.2 (2)	C14—C15—H15	121.8 (15)
C2—C3—H3	119.4 (14)	N2—C16—C15	123.93 (19)
C4—C3—H3	120.4 (14)	N2—C16—H16	114.8 (13)
C5—C4—C3	120.0 (2)	C15—C16—H16	121.2 (14)
C5—C4—H4	119.4 (15)	N1—C17—C18	113.91 (16)
C3—C4—H4	120.7 (15)	N1—C17—H17A	107.7 (13)
C4—C5—C6	121.29 (19)	C18—C17—H17A	111.6 (13)
C4—C5—H5	117.7 (14)	N1—C17—H17B	105.7 (12)
C6—C5—H5	121.0 (14)	C18—C17—H17B	108.3 (12)
C5—C6—C1	118.06 (17)	H17A—C17—H17B	109.3 (18)
C5—C6—C7	124.32 (17)	N3—C18—C19	122.41 (18)
C1—C6—C7	117.62 (16)	N3—C18—C17	118.83 (16)
C8—C7—C6	119.84 (17)	C19—C18—C17	118.76 (17)
C8—C7—C10	118.73 (17)	C20—C19—C18	119.05 (19)
C6—C7—C10	121.36 (16)	C20—C19—H19	120.5 (13)
C7—C8—C9	122.87 (18)	C18—C19—H19	120.4 (13)
C7—C8—H8	122.7 (13)	C21—C20—C19	119.32 (18)
C9—C8—H8	114.4 (13)	C21—C20—H20	120.6 (14)
O3—C9—N1	121.20 (17)	C19—C20—H20	120.0 (14)
O3—C9—C8	122.63 (18)	C22—C21—C20	117.54 (19)
N1—C9—C8	116.14 (16)	C22—C21—H21	119.6 (13)
O1—C10—O2	122.33 (16)	C20—C21—H21	122.8 (13)
O1—C10—C7	126.34 (17)	N3—C22—C21	124.1 (2)
O2—C10—C7	111.27 (15)	N3—C22—H22	116.5 (15)
O2—C11—C12	108.95 (15)	C21—C22—H22	119.4 (15)
O2—C11—H11A	109.3 (13)	O4^i—O4—H4A	68.4
C12—C11—H11A	109.9 (12)	O4^i—O4—H4B	48.2
O2—C11—H11B	108.8 (13)	H4A—O4—H4B	104.0
C12—C11—H11B	110.6 (13)
C9—N1—C1—C2	−172.75 (18)	C11—O2—C10—C7	173.42 (16)
C17—N1—C1—C2	5.5 (3)	C8—C7—C10—O1	166.6 (2)
C9—N1—C1—C6	7.1 (3)	C6—C7—C10—O1	−10.5 (3)
C17—N1—C1—C6	−174.69 (17)	C8—C7—C10—O2	−10.8 (2)
N1—C1—C2—C3	179.69 (19)	C6—C7—C10—O2	172.11 (16)
C6—C1—C2—C3	−0.1 (3)	C10—O2—C11—C12	−170.60 (16)
C1—C2—C3—C4	−0.9 (3)	C16—N2—C12—C13	−0.5 (3)
C2—C3—C4—C5	0.8 (3)	C16—N2—C12—C11	178.63 (18)
C3—C4—C5—C6	0.3 (3)	O2—C11—C12—N2	173.67 (16)
C4—C5—C6—C1	−1.3 (3)	O2—C11—C12—C13	−7.2 (3)
C4—C5—C6—C7	179.69 (19)	N2—C12—C13—C14	0.7 (3)
C2—C1—C6—C5	1.2 (3)	C11—C12—C13—C14	−178.30 (19)
N1—C1—C6—C5	−178.64 (17)	C12—C13—C14—C15	−0.2 (3)
C2—C1—C6—C7	−179.73 (17)	C13—C14—C15—C16	−0.4 (3)
N1—C1—C6—C7	0.4 (3)	C12—N2—C16—C15	−0.2 (3)
C5—C6—C7—C8	174.55 (19)	C14—C15—C16—N2	0.7 (4)
C1—C6—C7—C8	−4.5 (3)	C9—N1—C17—C18	91.8 (2)
C5—C6—C7—C10	−8.4 (3)	C1—N1—C17—C18	−86.6 (2)
C1—C6—C7—C10	172.59 (16)	C22—N3—C18—C19	0.4 (3)
C6—C7—C8—C9	1.5 (3)	C22—N3—C18—C17	−178.54 (19)
C10—C7—C8—C9	−175.68 (17)	N1—C17—C18—N3	−3.3 (3)
C1—N1—C9—O3	171.88 (18)	N1—C17—C18—C19	177.71 (18)
C17—N1—C9—O3	−6.4 (3)	N3—C18—C19—C20	−1.0 (3)
C1—N1—C9—C8	−9.9 (3)	C17—C18—C19—C20	177.95 (18)
C17—N1—C9—C8	171.83 (17)	C18—C19—C20—C21	0.7 (3)
C7—C8—C9—O3	−176.17 (19)	C19—C20—C21—C22	0.1 (3)
C7—C8—C9—N1	5.6 (3)	C18—N3—C22—C21	0.5 (3)
C11—O2—C10—O1	−4.1 (3)	C20—C21—C22—N3	−0.8 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N3^ii	0.98 (3)	2.50 (3)	3.344 (3)	145 (2)
O4—H4A···O3	0.87	1.87	2.647 (4)	147
O4—H4B···O3^i	0.87	2.26	2.989 (4)	141
C8—H8···O4^i	0.97 (2)	2.28 (2)	3.113 (4)	143.7 (17)
C13—H13···O4^i	1.00 (2)	2.44 (2)	3.345 (4)	149.3 (19)
C17—H17A···O3^ii	1.00 (2)	2.57 (2)	3.307 (3)	130.4 (16)
C11—H11A···Cg1^ii	1.02 (2)	2.85 (2)	3.673 (2)	137.9 (15)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z.