8-[N-(tert-Butoxy­carbonyl)-l-glycyl]­quinolin-8-amine

Shao, Y.; Tu, C.; Zhang, J.; Guo, Z.

doi:10.1107/S160053680300607X

8-[N-(tert-Butoxycarbonyl)-L-glycyl]quinolin-8-amine

The title compound, C₁₆H₁₉N₃O₃, has two crystallographically independent molecules in the asymmetric unit. There are two intermolecular (N—H

O) and two intramolecular hydrogen bonds (N—H

N) in the crystal structure. The crystal packing is stabilized by π–π-stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300607X/na6217sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680300607X/na6217Isup2.hkl Contains datablock I

CCDC reference: 209974

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.178
Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



PLAT_725  Alert A D-H     Calc     0.85990, Rep     0.78(3), Dev.      0.08 Ang.
                     N2A  -H2AA    1.555   1.555

PLAT_728  Alert A D-H..A  Calc      109.56, Rep      113(2), Dev.      3.44 Deg.
                     N2A  -H2AA -N1A     1.555   1.555   1.555


 2 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

Aminoquinoline-based ligands possess a strong fluorescent property which could be used as a potential probe for zinc ion detection (Jiang et al., 2002). Moreover, some novel quinoline carboxamide ligands and their copper complexes as well as platinum complexes with pyridine carboxamide ligand (Zhang, Liu et al., 2002) showed potent cytotoxicity against human leukaemia, murine leukaemia, human hepatoma and human lung adenocarcinoma cell lines (Zhang et al., 2003). Compound (I) and its Cu^II complex have been synthesized and reported previously. In this work, we report the crystral structure of (I).

The X-ray crystallographic study shows that the bond lengths and angles are within the normal ranges. The N2A—C10A and N2A—C8A bond distances in (I) are comparable with those in N-(8-quinolyl)pyridine-2-Carboxamide [1.357 (2) and 1.401 (2) Å; Zhang et al., 2001] and N-(8-quinolyl)pyridine-3-carboxamide [1.349 (3) and 1.405 (3) Å; Zhang, Tu et al., 2002] and the C—C and C═O ond lengths are similar to those reported in [N-(8-quinolyl)-L-alanine-N'-BOC-carboxamide]copper(II) (Zhang et al., 2003). The torsion angle C12A—N3A—C11A—C10A is 77.7 (3)° and N2A—C10A—C11A—N3A is −137.2 (2)°. There are two intermolecular hydrogen bonds (N3A—H3AA···O1B and N3B—H3BA···O1A) and two intramolecular hydrogen bonds (N2B—H2BA···N1B and N2A—H2AA···N1A) in the crystal.

The crystal packing of the compound (I) is shown in Fig. 2. There is a π–π-stacking interaction between the adjacent molecules packed in the opposite direction. The distance between the two adjacent quinoline rings is 3.524 (3) Å and the angle between the two planes is 2.1°. This interaction keeps the quinoline planes in a face-to-face fashion giving origin to alternating hydrophilic and hydrophobic layers.

Experimental top

The title compound was obtained by the reaction of one molar equivalent 8-aminoquinoline and N-(tert-butoxycarbonyl)glycine in THF at 258 K for 1 h (Zhang et al., 2003). Single crystals suitable for X-ray diffraction were recrystallized from THF and ethanol.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing of the crystal.

8-[N-(tert-Butoxycarbonyl)-L-glycyl]quinolin-8-amine top

Crystal data top

C₁₆H₁₉N₃O₃	Z = 4
M_r = 301.34	F(000) = 640
Triclinic, P1	D_x = 1.298 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.430 (2) Å	Cell parameters from 5698 reflections
b = 12.240 (2) Å	θ = 1.7–25.0°
c = 12.960 (3) Å	µ = 0.09 mm⁻¹
α = 65.33 (3)°	T = 293 K
β = 80.60 (3)°	Block, brown
γ = 69.44 (3)°	0.40 × 0.30 × 0.30 mm
V = 1542.4 (7) Å³

Data collection top

Siemens P4 diffractometer	3476 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
2θ/ω scans	h = 0→13
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = −13→14
T_min = 0.968, T_max = 0.973	l = −15→15
5698 measured reflections	3 standard reflections every 97 reflections
5401 independent reflections	intensity decay: 7.1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1	w = 1/[σ²(F_o²) + (0.1P)² + 0.4212P] where P = (F_o² + 2F_c²)/3
5401 reflections	(Δ/σ)_max < 0.001
397 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₉N₃O₃	γ = 69.44 (3)°
M_r = 301.34	V = 1542.4 (7) Å³
Triclinic, P1	Z = 4
a = 11.430 (2) Å	Mo Kα radiation
b = 12.240 (2) Å	µ = 0.09 mm⁻¹
c = 12.960 (3) Å	T = 293 K
α = 65.33 (3)°	0.40 × 0.30 × 0.30 mm
β = 80.60 (3)°

Data collection top

Siemens P4 diffractometer	3476 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	R_int = 0.023
T_min = 0.968, T_max = 0.973	3 standard reflections every 97 reflections
5698 measured reflections	intensity decay: 7.1%
5401 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1	Δρ_max = 0.20 e Å⁻³
5401 reflections	Δρ_min = −0.32 e Å⁻³
397 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

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

	x	y	z	U_iso*/U_eq
O1A	0.36052 (18)	0.2795 (2)	0.06456 (16)	0.0591 (5)
O2A	0.1324 (2)	0.61749 (19)	−0.06096 (15)	0.0628 (6)
O3A	0.22243 (16)	0.67086 (16)	0.04713 (14)	0.0463 (4)
N1A	0.0626 (2)	0.2917 (2)	−0.17444 (17)	0.0472 (5)
N2A	0.20043 (19)	0.2887 (2)	−0.02537 (18)	0.0459 (5)
H2AA	0.1203	0.3164	−0.0295	0.055*
N3A	0.1911 (2)	0.48488 (19)	0.11670 (17)	0.0472 (5)
H3AA	0.2218	0.4732	0.1782	0.057*
C1A	−0.0064 (3)	0.2960 (3)	−0.2491 (2)	0.0549 (7)
H1AB	−0.0914	0.3398	−0.2497	0.066*
C2A	0.0399 (3)	0.2392 (3)	−0.3272 (2)	0.0561 (7)
H2AB	−0.0134	0.2452	−0.3777	0.067*
C3A	0.1634 (3)	0.1754 (3)	−0.3288 (2)	0.0546 (7)
H3AB	0.1957	0.1373	−0.3807	0.065*
C4A	0.2427 (2)	0.1669 (2)	−0.2512 (2)	0.0454 (6)
C5A	0.3719 (3)	0.1022 (3)	−0.2457 (2)	0.0555 (7)
H5AA	0.4095	0.0624	−0.2956	0.067*
C6A	0.4416 (3)	0.0977 (3)	−0.1682 (3)	0.0583 (8)
H6AA	0.5267	0.0533	−0.1647	0.070*
C7A	0.3883 (2)	0.1587 (2)	−0.0927 (2)	0.0519 (7)
H7AA	0.4385	0.1551	−0.0409	0.062*
C8A	0.2635 (2)	0.2230 (2)	−0.0951 (2)	0.0414 (6)
C9A	0.1869 (2)	0.2280 (2)	−0.17500 (19)	0.0394 (6)
C10A	0.2488 (2)	0.3142 (2)	0.0477 (2)	0.0419 (6)
C11A	0.1538 (2)	0.3866 (2)	0.1114 (2)	0.0446 (6)
H11A	0.0740	0.4242	0.0741	0.054*
H11B	0.1429	0.3282	0.1879	0.054*
C12A	0.1783 (2)	0.5940 (2)	0.0269 (2)	0.0412 (6)
C13A	0.2193 (2)	0.7969 (2)	−0.0400 (2)	0.0473 (6)
C14A	0.2676 (4)	0.8516 (3)	0.0228 (3)	0.0849 (11)
H14A	0.2110	0.8608	0.0842	0.127*
H14B	0.2741	0.9330	−0.0283	0.127*
H14C	0.3485	0.7958	0.0524	0.127*
C15A	0.3061 (4)	0.7822 (4)	−0.1376 (3)	0.0932 (13)
H15A	0.2744	0.7466	−0.1761	0.140*
H15B	0.3876	0.7271	−0.1092	0.140*
H15C	0.3116	0.8637	−0.1897	0.140*
C16A	0.0882 (3)	0.8761 (3)	−0.0770 (3)	0.0820 (11)
H16A	0.0364	0.8815	−0.0120	0.123*
H16B	0.0568	0.8380	−0.1132	0.123*
H16C	0.0872	0.9596	−0.1295	0.123*
O1B	0.24428 (19)	0.3865 (2)	0.35994 (16)	0.0647 (6)
O2B	0.3242 (2)	0.0671 (2)	0.47763 (17)	0.0705 (6)
O3B	0.30002 (18)	0.06023 (19)	0.30994 (16)	0.0577 (5)
N1B	0.5007 (2)	0.3764 (2)	0.63094 (18)	0.0489 (5)
N2B	0.3786 (2)	0.3532 (2)	0.48825 (17)	0.0468 (5)
H2BA	0.4550	0.3139	0.5090	0.056*
N3B	0.4049 (2)	0.1789 (2)	0.31330 (18)	0.0502 (6)
H3BA	0.4192	0.1938	0.2422	0.060*
C1B	0.5631 (3)	0.3822 (3)	0.7043 (2)	0.0576 (7)
H1BB	0.6494	0.3442	0.7065	0.069*
C2B	0.5073 (3)	0.4422 (3)	0.7790 (2)	0.0618 (8)
H2BB	0.5554	0.4426	0.8302	0.074*
C3B	0.3825 (3)	0.4998 (3)	0.7760 (2)	0.0579 (8)
H3BB	0.3439	0.5387	0.8264	0.070*
C4B	0.3105 (3)	0.5011 (2)	0.6965 (2)	0.0462 (6)
C5B	0.1801 (3)	0.5606 (3)	0.6856 (2)	0.0566 (7)
H5BA	0.1364	0.6037	0.7316	0.068*
C6B	0.1187 (3)	0.5548 (3)	0.6081 (2)	0.0575 (7)
H6BA	0.0330	0.5952	0.6011	0.069*
C7B	0.1809 (3)	0.4892 (3)	0.5376 (2)	0.0506 (7)
H7BA	0.1365	0.4870	0.4849	0.061*
C8B	0.3071 (2)	0.4287 (2)	0.5472 (2)	0.0423 (6)
C9B	0.3752 (2)	0.4354 (2)	0.62616 (19)	0.0413 (6)
C10B	0.3465 (2)	0.3325 (2)	0.4042 (2)	0.0453 (6)
C11B	0.4502 (3)	0.2383 (3)	0.3666 (2)	0.0516 (7)
H11C	0.5055	0.2816	0.3136	0.062*
H11D	0.4986	0.1733	0.4321	0.062*
C12B	0.3403 (3)	0.1002 (3)	0.3762 (2)	0.0486 (6)
C13B	0.2032 (3)	−0.0028 (3)	0.3500 (3)	0.0586 (8)
C14B	0.2455 (4)	−0.1258 (3)	0.4523 (3)	0.0852 (11)
H14D	0.2516	−0.1079	0.5163	0.128*
H14E	0.3257	−0.1771	0.4361	0.128*
H14F	0.1859	−0.1705	0.4695	0.128*
C15B	0.0849 (3)	0.0882 (3)	0.3736 (3)	0.0878 (11)
H15D	0.0613	0.1642	0.3063	0.132*
H15E	0.0982	0.1085	0.4338	0.132*
H15F	0.0195	0.0501	0.3956	0.132*
C16B	0.1912 (3)	−0.0287 (4)	0.2487 (3)	0.0846 (11)
H16D	0.1642	0.0500	0.1845	0.127*
H16E	0.1311	−0.0727	0.2658	0.127*
H16F	0.2708	−0.0800	0.2313	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0459 (11)	0.0837 (14)	0.0583 (12)	−0.0205 (10)	−0.0068 (9)	−0.0357 (11)
O2A	0.0923 (15)	0.0659 (13)	0.0415 (10)	−0.0410 (12)	−0.0180 (10)	−0.0123 (9)
O3A	0.0499 (10)	0.0469 (10)	0.0496 (10)	−0.0191 (8)	−0.0089 (8)	−0.0199 (8)
N1A	0.0454 (13)	0.0544 (13)	0.0446 (12)	−0.0149 (10)	−0.0030 (10)	−0.0219 (10)
N2A	0.0399 (12)	0.0507 (12)	0.0529 (13)	−0.0115 (10)	−0.0066 (10)	−0.0258 (11)
N3A	0.0605 (14)	0.0456 (12)	0.0412 (12)	−0.0187 (11)	−0.0148 (10)	−0.0157 (10)
C1A	0.0513 (16)	0.0695 (19)	0.0485 (15)	−0.0220 (14)	−0.0042 (13)	−0.0238 (14)
C2A	0.069 (2)	0.0662 (18)	0.0435 (15)	−0.0305 (16)	−0.0059 (13)	−0.0214 (14)
C3A	0.078 (2)	0.0550 (17)	0.0417 (14)	−0.0306 (16)	0.0058 (14)	−0.0242 (13)
C4A	0.0561 (16)	0.0404 (14)	0.0422 (14)	−0.0222 (13)	0.0084 (12)	−0.0162 (11)
C5A	0.0604 (18)	0.0489 (16)	0.0574 (17)	−0.0179 (14)	0.0145 (14)	−0.0262 (14)
C6A	0.0424 (16)	0.0500 (16)	0.076 (2)	−0.0099 (13)	0.0083 (14)	−0.0253 (15)
C7A	0.0449 (16)	0.0488 (15)	0.0604 (17)	−0.0153 (13)	−0.0043 (13)	−0.0182 (13)
C8A	0.0445 (14)	0.0377 (13)	0.0428 (13)	−0.0150 (11)	−0.0005 (11)	−0.0148 (11)
C9A	0.0444 (14)	0.0351 (12)	0.0381 (13)	−0.0162 (11)	0.0021 (11)	−0.0117 (10)
C10A	0.0464 (16)	0.0411 (13)	0.0397 (13)	−0.0177 (12)	−0.0057 (11)	−0.0121 (11)
C11A	0.0471 (15)	0.0451 (14)	0.0446 (14)	−0.0196 (12)	−0.0026 (11)	−0.0154 (12)
C12A	0.0434 (14)	0.0472 (14)	0.0401 (14)	−0.0177 (12)	−0.0019 (11)	−0.0204 (12)
C13A	0.0540 (16)	0.0434 (14)	0.0492 (15)	−0.0200 (12)	−0.0010 (12)	−0.0186 (12)
C14A	0.126 (3)	0.064 (2)	0.083 (2)	−0.048 (2)	−0.026 (2)	−0.0226 (18)
C15A	0.121 (3)	0.083 (2)	0.094 (3)	−0.061 (2)	0.053 (2)	−0.049 (2)
C16A	0.074 (2)	0.0571 (19)	0.092 (3)	−0.0179 (17)	−0.0158 (19)	−0.0058 (18)
O1B	0.0612 (13)	0.0783 (14)	0.0557 (12)	−0.0013 (11)	−0.0214 (10)	−0.0366 (11)
O2B	0.0931 (17)	0.0811 (15)	0.0479 (12)	−0.0375 (13)	0.0087 (11)	−0.0304 (11)
O3B	0.0583 (12)	0.0779 (13)	0.0625 (12)	−0.0378 (10)	0.0153 (9)	−0.0441 (11)
N1B	0.0536 (14)	0.0473 (13)	0.0485 (12)	−0.0175 (11)	−0.0090 (10)	−0.0169 (10)
N2B	0.0458 (12)	0.0511 (13)	0.0464 (12)	−0.0089 (10)	−0.0095 (10)	−0.0237 (10)
N3B	0.0577 (14)	0.0634 (14)	0.0433 (12)	−0.0259 (12)	0.0042 (10)	−0.0302 (11)
C1B	0.0610 (18)	0.0588 (17)	0.0597 (17)	−0.0241 (15)	−0.0130 (14)	−0.0209 (14)
C2B	0.082 (2)	0.0606 (18)	0.0574 (17)	−0.0323 (17)	−0.0183 (16)	−0.0227 (15)
C3B	0.086 (2)	0.0547 (17)	0.0471 (15)	−0.0302 (16)	−0.0003 (15)	−0.0271 (13)
C4B	0.0612 (17)	0.0408 (14)	0.0403 (13)	−0.0209 (13)	0.0007 (12)	−0.0158 (12)
C5B	0.0672 (19)	0.0533 (17)	0.0501 (16)	−0.0147 (14)	0.0049 (14)	−0.0267 (14)
C6B	0.0533 (17)	0.0562 (17)	0.0563 (17)	−0.0111 (14)	0.0002 (13)	−0.0212 (14)
C7B	0.0546 (17)	0.0529 (16)	0.0441 (14)	−0.0148 (13)	−0.0079 (12)	−0.0179 (13)
C8B	0.0523 (16)	0.0398 (13)	0.0354 (13)	−0.0149 (12)	−0.0022 (11)	−0.0146 (11)
C9B	0.0542 (16)	0.0360 (13)	0.0356 (12)	−0.0201 (12)	−0.0036 (11)	−0.0101 (11)
C10B	0.0535 (16)	0.0487 (15)	0.0384 (13)	−0.0183 (13)	−0.0043 (12)	−0.0184 (12)
C11B	0.0531 (16)	0.0585 (17)	0.0550 (16)	−0.0189 (13)	−0.0056 (13)	−0.0307 (14)
C12B	0.0517 (16)	0.0555 (16)	0.0481 (16)	−0.0157 (13)	0.0040 (12)	−0.0319 (13)
C13B	0.0501 (17)	0.0582 (17)	0.0715 (19)	−0.0251 (14)	0.0051 (14)	−0.0246 (15)
C14B	0.079 (2)	0.064 (2)	0.107 (3)	−0.0287 (18)	−0.014 (2)	−0.020 (2)
C15B	0.060 (2)	0.074 (2)	0.113 (3)	−0.0196 (18)	0.020 (2)	−0.030 (2)
C16B	0.077 (2)	0.103 (3)	0.105 (3)	−0.050 (2)	−0.005 (2)	−0.050 (2)

Geometric parameters (Å, º) top

O1A—C10A	1.221 (3)	O1B—C10B	1.221 (3)
O2A—C12A	1.213 (3)	O2B—C12B	1.206 (3)
O3A—C12A	1.338 (3)	O3B—C12B	1.351 (3)
O3A—C13A	1.475 (3)	O3B—C13B	1.472 (3)
N1A—C1A	1.319 (3)	N1B—C1B	1.316 (3)
N1A—C9A	1.360 (3)	N1B—C9B	1.359 (3)
N2A—C10A	1.356 (3)	N2B—C10B	1.346 (3)
N2A—C8A	1.403 (3)	N2B—C8B	1.400 (3)
N2A—H2AA	0.8600	N2B—H2BA	0.8600
N3A—C12A	1.334 (3)	N3B—C12B	1.336 (3)
N3A—C11A	1.439 (3)	N3B—C11B	1.441 (3)
N3A—H3AA	0.8600	N3B—H3BA	0.8600
C1A—C2A	1.393 (4)	C1B—C2B	1.395 (4)
C1A—H1AB	0.9300	C1B—H1BB	0.9300
C2A—C3A	1.354 (4)	C2B—C3B	1.350 (4)
C2A—H2AB	0.9300	C2B—H2BB	0.9300
C3A—C4A	1.411 (4)	C3B—C4B	1.413 (4)
C3A—H3AB	0.9300	C3B—H3BB	0.9300
C4A—C5A	1.407 (4)	C4B—C5B	1.411 (4)
C4A—C9A	1.420 (3)	C4B—C9B	1.414 (4)
C5A—C6A	1.354 (4)	C5B—C6B	1.353 (4)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.408 (4)	C6B—C7B	1.408 (4)
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C7A—C8A	1.364 (4)	C7B—C8B	1.369 (4)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.431 (3)	C8B—C9B	1.427 (3)
C10A—C11A	1.513 (4)	C10B—C11B	1.514 (4)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C13A—C16A	1.498 (4)	C13B—C15B	1.502 (4)
C13A—C15A	1.506 (4)	C13B—C16B	1.510 (4)
C13A—C14A	1.510 (4)	C13B—C14B	1.514 (5)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600

C12A—O3A—C13A	121.4 (2)	C12B—O3B—C13B	121.6 (2)
C1A—N1A—C9A	117.3 (2)	C1B—N1B—C9B	117.7 (2)
C10A—N2A—C8A	128.7 (2)	C10B—N2B—C8B	130.1 (2)
C10A—N2A—H2AA	115.6	C10B—N2B—H2BA	114.9
C8A—N2A—H2AA	115.6	C8B—N2B—H2BA	114.9
C12A—N3A—C11A	120.5 (2)	C12B—N3B—C11B	118.8 (2)
C12A—N3A—H3AA	119.8	C12B—N3B—H3BA	120.6
C11A—N3A—H3AA	119.8	C11B—N3B—H3BA	120.6
N1A—C1A—C2A	124.2 (3)	N1B—C1B—C2B	123.7 (3)
N1A—C1A—H1AB	117.9	N1B—C1B—H1BB	118.1
C2A—C1A—H1AB	117.9	C2B—C1B—H1BB	118.1
C3A—C2A—C1A	119.3 (3)	C3B—C2B—C1B	119.1 (3)
C3A—C2A—H2AB	120.4	C3B—C2B—H2BB	120.4
C1A—C2A—H2AB	120.4	C1B—C2B—H2BB	120.4
C2A—C3A—C4A	119.5 (3)	C2B—C3B—C4B	120.1 (3)
C2A—C3A—H3AB	120.2	C2B—C3B—H3BB	120.0
C4A—C3A—H3AB	120.2	C4B—C3B—H3BB	120.0
C5A—C4A—C3A	123.8 (3)	C5B—C4B—C9B	119.2 (2)
C5A—C4A—C9A	119.2 (2)	C5B—C4B—C3B	124.2 (3)
C3A—C4A—C9A	117.1 (2)	C9B—C4B—C3B	116.5 (3)
C6A—C5A—C4A	120.2 (3)	C6B—C5B—C4B	119.9 (3)
C6A—C5A—H5AA	119.9	C6B—C5B—H5BA	120.0
C4A—C5A—H5AA	119.9	C4B—C5B—H5BA	120.0
C5A—C6A—C7A	121.5 (3)	C5B—C6B—C7B	121.9 (3)
C5A—C6A—H6AA	119.2	C5B—C6B—H6BA	119.1
C7A—C6A—H6AA	119.2	C7B—C6B—H6BA	119.1
C8A—C7A—C6A	120.3 (3)	C8B—C7B—C6B	119.7 (2)
C8A—C7A—H7AA	119.8	C8B—C7B—H7BA	120.1
C6A—C7A—H7AA	119.8	C6B—C7B—H7BA	120.1
C7A—C8A—N2A	125.5 (2)	C7B—C8B—N2B	125.5 (2)
C7A—C8A—C9A	119.5 (2)	C7B—C8B—C9B	119.8 (2)
N2A—C8A—C9A	115.0 (2)	N2B—C8B—C9B	114.6 (2)
N1A—C9A—C4A	122.6 (2)	N1B—C9B—C4B	122.8 (2)
N1A—C9A—C8A	118.1 (2)	N1B—C9B—C8B	117.9 (2)
C4A—C9A—C8A	119.2 (2)	C4B—C9B—C8B	119.3 (2)
O1A—C10A—N2A	123.6 (2)	O1B—C10B—N2B	123.5 (2)
O1A—C10A—C11A	121.1 (2)	O1B—C10B—C11B	122.6 (2)
N2A—C10A—C11A	115.3 (2)	N2B—C10B—C11B	113.9 (2)
N3A—C11A—C10A	112.1 (2)	N3B—C11B—C10B	113.1 (2)
N3A—C11A—H11A	109.2	N3B—C11B—H11C	109.0
C10A—C11A—H11A	109.2	C10B—C11B—H11C	109.0
N3A—C11A—H11B	109.2	N3B—C11B—H11D	109.0
C10A—C11A—H11B	109.2	C10B—C11B—H11D	109.0
H11A—C11A—H11B	107.9	H11C—C11B—H11D	107.8
O2A—C12A—N3A	122.9 (2)	O2B—C12B—N3B	124.6 (3)
O2A—C12A—O3A	125.7 (2)	O2B—C12B—O3B	125.5 (3)
N3A—C12A—O3A	111.5 (2)	N3B—C12B—O3B	109.9 (2)
O3A—C13A—C16A	110.7 (2)	O3B—C13B—C15B	108.5 (2)
O3A—C13A—C15A	109.8 (2)	O3B—C13B—C16B	101.8 (2)
C16A—C13A—C15A	112.6 (3)	C15B—C13B—C16B	111.7 (3)
O3A—C13A—C14A	102.6 (2)	O3B—C13B—C14B	111.5 (2)
C16A—C13A—C14A	110.2 (3)	C15B—C13B—C14B	112.4 (3)
C15A—C13A—C14A	110.6 (3)	C16B—C13B—C14B	110.4 (3)
C13A—C14A—H14A	109.5	C13B—C14B—H14D	109.5
C13A—C14A—H14B	109.5	C13B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C13A—C14A—H14C	109.5	C13B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C13A—C15A—H15A	109.5	C13B—C15B—H15D	109.5
C13A—C15A—H15B	109.5	C13B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C13A—C15A—H15C	109.5	C13B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C13A—C16A—H16A	109.5	C13B—C16B—H16D	109.5
C13A—C16A—H16B	109.5	C13B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C13A—C16A—H16C	109.5	C13B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5

C9A—N1A—C1A—C2A	0.4 (4)	C9B—N1B—C1B—C2B	1.8 (4)
N1A—C1A—C2A—C3A	−0.3 (4)	N1B—C1B—C2B—C3B	−1.1 (4)
C1A—C2A—C3A—C4A	0.3 (4)	C1B—C2B—C3B—C4B	−1.3 (4)
C2A—C3A—C4A—C5A	179.7 (3)	C2B—C3B—C4B—C5B	−178.9 (3)
C2A—C3A—C4A—C9A	−0.4 (4)	C2B—C3B—C4B—C9B	2.6 (4)
C3A—C4A—C5A—C6A	−179.6 (2)	C9B—C4B—C5B—C6B	−0.3 (4)
C9A—C4A—C5A—C6A	0.5 (4)	C3B—C4B—C5B—C6B	−178.8 (3)
C4A—C5A—C6A—C7A	−1.1 (4)	C4B—C5B—C6B—C7B	0.8 (4)
C5A—C6A—C7A—C8A	0.8 (4)	C5B—C6B—C7B—C8B	0.2 (4)
C6A—C7A—C8A—N2A	−179.1 (2)	C6B—C7B—C8B—N2B	175.3 (2)
C6A—C7A—C8A—C9A	0.1 (4)	C6B—C7B—C8B—C9B	−1.7 (4)
C10A—N2A—C8A—C7A	8.0 (4)	C10B—N2B—C8B—C7B	7.3 (4)
C10A—N2A—C8A—C9A	−171.2 (2)	C10B—N2B—C8B—C9B	−175.6 (2)
C1A—N1A—C9A—C4A	−0.5 (4)	C1B—N1B—C9B—C4B	−0.3 (4)
C1A—N1A—C9A—C8A	179.6 (2)	C1B—N1B—C9B—C8B	−179.7 (2)
C5A—C4A—C9A—N1A	−179.5 (2)	C5B—C4B—C9B—N1B	179.6 (2)
C3A—C4A—C9A—N1A	0.5 (3)	C3B—C4B—C9B—N1B	−1.8 (4)
C5A—C4A—C9A—C8A	0.4 (3)	C5B—C4B—C9B—C8B	−1.1 (4)
C3A—C4A—C9A—C8A	−179.5 (2)	C3B—C4B—C9B—C8B	177.5 (2)
C7A—C8A—C9A—N1A	179.3 (2)	C7B—C8B—C9B—N1B	−178.5 (2)
N2A—C8A—C9A—N1A	−1.5 (3)	N2B—C8B—C9B—N1B	4.1 (3)
C7A—C8A—C9A—C4A	−0.6 (3)	C7B—C8B—C9B—C4B	2.1 (4)
N2A—C8A—C9A—C4A	178.6 (2)	N2B—C8B—C9B—C4B	−175.2 (2)
C8A—N2A—C10A—O1A	−1.2 (4)	C8B—N2B—C10B—O1B	4.6 (4)
C8A—N2A—C10A—C11A	−179.5 (2)	C8B—N2B—C10B—C11B	−177.1 (2)
C12A—N3A—C11A—C10A	77.7 (3)	C12B—N3B—C11B—C10B	−67.4 (3)
O1A—C10A—C11A—N3A	44.5 (3)	O1B—C10B—C11B—N3B	−25.1 (4)
N2A—C10A—C11A—N3A	−137.2 (2)	N2B—C10B—C11B—N3B	156.5 (2)
C11A—N3A—C12A—O2A	2.2 (4)	C11B—N3B—C12B—O2B	−5.8 (4)
C11A—N3A—C12A—O3A	−177.6 (2)	C11B—N3B—C12B—O3B	176.4 (2)
C13A—O3A—C12A—O2A	−0.2 (4)	C13B—O3B—C12B—O2B	16.6 (4)
C13A—O3A—C12A—N3A	179.6 (2)	C13B—O3B—C12B—N3B	−165.7 (2)
C12A—O3A—C13A—C16A	58.0 (3)	C12B—O3B—C13B—C15B	62.2 (3)
C12A—O3A—C13A—C15A	−66.8 (3)	C12B—O3B—C13B—C16B	−179.9 (3)
C12A—O3A—C13A—C14A	175.5 (2)	C12B—O3B—C13B—C14B	−62.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AA···N1A	0.78 (3)	2.26 (3)	2.669 (3)	113 (2)
N3A—H3AA···O1B	0.86	2.16	2.949 (3)	153
N2B—H2BA···N1B	0.86	2.22	2.647 (3)	111
N3B—H3BA···O1A	0.86	2.20	2.991 (3)	153

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉N₃O₃
M_r	301.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.430 (2), 12.240 (2), 12.960 (3)
α, β, γ (°)	65.33 (3), 80.60 (3), 69.44 (3)
V (Å³)	1542.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.30 × 0.30

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	Empirical (using intensity measurements) (North et al., 1968)
T_min, T_max	0.968, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	5698, 5401, 3476
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.178, 1
No. of reflections	5401
No. of parameters	397
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.32

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

O1A—C10A	1.221 (3)	O1B—C10B	1.221 (3)
O2A—C12A	1.213 (3)	O2B—C12B	1.206 (3)
O3A—C12A	1.338 (3)	O3B—C12B	1.351 (3)
O3A—C13A	1.475 (3)	O3B—C13B	1.472 (3)
N1A—C1A	1.319 (3)	N1B—C1B	1.316 (3)
N1A—C9A	1.360 (3)	N1B—C9B	1.359 (3)
N2A—C10A	1.356 (3)	N2B—C10B	1.346 (3)
N2A—C8A	1.403 (3)	N2B—C8B	1.400 (3)
N3A—C12A	1.334 (3)	N3B—C12B	1.336 (3)
N3A—C11A	1.439 (3)	N3B—C11B	1.441 (3)

C12A—O3A—C13A	121.4 (2)	C12B—O3B—C13B	121.6 (2)
C10A—N2A—C8A	128.7 (2)	C10B—N2B—C8B	130.1 (2)
C12A—N3A—C11A	120.5 (2)	C12B—N3B—C11B	118.8 (2)
N2A—C8A—C9A	115.0 (2)	N2B—C8B—C9B	114.6 (2)
O1A—C10A—N2A	123.6 (2)	O1B—C10B—N2B	123.5 (2)
O1A—C10A—C11A	121.1 (2)	O1B—C10B—C11B	122.6 (2)
N2A—C10A—C11A	115.3 (2)	N2B—C10B—C11B	113.9 (2)
N3A—C11A—C10A	112.1 (2)	N3B—C11B—C10B	113.1 (2)
O2A—C12A—N3A	122.9 (2)	O2B—C12B—N3B	124.6 (3)
O2A—C12A—O3A	125.7 (2)	O2B—C12B—O3B	125.5 (3)
N3A—C12A—O3A	111.5 (2)	N3B—C12B—O3B	109.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AA···N1A	0.78 (3)	2.26 (3)	2.669 (3)	113 (2)
N3A—H3AA···O1B	0.86	2.16	2.949 (3)	153
N2B—H2BA···N1B	0.86	2.22	2.647 (3)	111
N3B—H3BA···O1A	0.86	2.20	2.991 (3)	153

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8-[N-(tert-Butoxy­carbonyl)-L-glycyl]­quinolin-8-amine

Supporting information

Key indicators

checkCIF results

8-[N-(tert-Butoxycarbonyl)-L-glycyl]quinolin-8-amine