4-(2-Benzyl­amino­acet­yl)-1,2,3,4-tetra­hydro­quinoxalin-2-one

Kruszynski, R.; Trzesowska, A.; Czestkowski, W.; Bartczak, T.J.; Mikiciuk-Olasik, E.

doi:10.1107/S1600536806032661

Buy article online - an online subscription or single-article purchase is required to access this article.

4-(2-Benzylaminoacetyl)-1,2,3,4-tetrahydroquinoxalin-2-one

R. Kruszynski, A. Trzesowska, W. Czestkowski, T. J. Bartczak and E. Mikiciuk-Olasik

All interatomic distances of the title compound, C₁₇H₁₇N₃O₂, are normal. The phenyl ring of the benzylaminomethyl substituent is disordered over two positions. The heteroatom ring of the quinoxolinone system shows a half-chair conformation. The molecules are held together by intermolecular N—H

O hydrogen bonds resulting in a chain along the crystallographic c axis. The chains are linked via weak intermolecular C—H

O and C—H

N hydrogen bonds into a three-dimensional hydrogen-bonded network.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032661/bt2171sup1.cif Contains datablocks global, II
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032661/bt2171IIsup2.hkl Contains datablock II

CCDC reference: 620700

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.044
wR factor = 0.155
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  C15    ..  C19     ..       2.98 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C16    ..  C18     ..       2.99 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C19'   ..  C19'    ..       2.98 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT301_ALERT_3_C Main Residue  Disorder .........................      15.00 Perc.

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software; data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 (Version 1.062; Farrugia, 1997) and Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

4-(2-Benzylaminoacetyl)-1,2,3,4-tetrahydroquinoxalin-2-one top

Crystal data top

C₁₇H₁₇N₃O₂	Z = 2
M_r = 295.34	F(000) = 312
Triclinic, P1	D_x = 1.290 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 4.701 (1) Å	Cell parameters from 99 reflections
b = 12.415 (2) Å	θ = 4–50°
c = 14.083 (3) Å	µ = 0.70 mm⁻¹
α = 110.77 (3)°	T = 291 K
β = 93.16 (3)°	Prism, colourless
γ = 96.04 (3)°	0.35 × 0.31 × 0.27 mm
V = 760.5 (3) Å³

Data collection top

Kuma KM-4 diffractometer	2835 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 80.7°, θ_min = 3.4°
ω–2θ scans	h = −5→5
Absorption correction: ψ scan (North et al., 1968)	k = −7→15
T_min = 0.784, T_max = 0.820	l = −17→16
3332 measured reflections	3 standard reflections every 100 reflections
3191 independent reflections	intensity decay: 11.2%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: mixed
wR(F²) = 0.155	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.077P)² + 0.1995P] where P = (F_o² + 2F_c²)/3
3191 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

Experimental. For (I): 1H NMR (DMSO/TMS, p.p.m.): 2.35 (s, 6H, 2CH3), 4.45 (s, 4H, 2CH2), 7.45 (s, 2H, Har), 9.75 (s, 2H, 2NHCO).

For (II): 1H NMR (DMSO/TMS, p.p.m.): 3.21 (broad, 1H, NHCH2), 3.6 (s, 2H) 3.75 (s, 2H, CH2CO), 4.50 (s, 2H, NCH2Ph), 7.25 (m, 9H, Har), 10.00 (broad, 1H, NHCO).

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	Occ. (<1)
N1	0.4465 (3)	0.46485 (11)	0.26107 (9)	0.0411 (3)
O1	0.0468 (3)	0.60225 (11)	0.12859 (9)	0.0595 (4)
O11	0.2272 (3)	0.53381 (10)	0.40433 (9)	0.0605 (4)
N2	0.2493 (3)	0.43696 (11)	0.06757 (10)	0.0469 (3)
H2N	0.1514	0.4216	0.0080	0.056*
N3	0.1126 (3)	0.32776 (11)	0.42530 (9)	0.0444 (3)
H3N	0.0938	0.3986	0.4713	0.053*
C1	0.5428 (3)	0.37455 (13)	0.17962 (11)	0.0392 (3)
C2	0.7312 (4)	0.30156 (15)	0.19305 (12)	0.0472 (4)
H2	0.8084	0.3115	0.2583	0.057*
C3	0.8046 (4)	0.21369 (17)	0.10903 (14)	0.0566 (4)
H3	0.9268	0.1632	0.1183	0.068*
C4	0.6979 (4)	0.20048 (17)	0.01168 (14)	0.0592 (5)
H4	0.7476	0.1411	−0.0444	0.071*
C5	0.5179 (4)	0.27530 (15)	−0.00244 (12)	0.0517 (4)
H5	0.4490	0.2672	−0.0681	0.062*
C6	0.4390 (3)	0.36271 (13)	0.08095 (11)	0.0420 (3)
C7	0.2157 (4)	0.53793 (13)	0.14071 (12)	0.0456 (4)
C8	0.4070 (4)	0.56881 (13)	0.23882 (12)	0.0485 (4)
H8A	0.5924	0.6071	0.2330	0.058*
H8B	0.3214	0.6225	0.2945	0.058*
C11	0.3340 (3)	0.45355 (13)	0.34560 (10)	0.0411 (3)
C12	0.3461 (3)	0.34270 (13)	0.36611 (11)	0.0422 (3)
H12A	0.3291	0.2771	0.3021	0.051*
H12B	0.5289	0.3465	0.4035	0.051*
C13	0.1512 (5)	0.24340 (15)	0.47346 (12)	0.0554 (4)
H13A	0.0177	0.2518	0.5249	0.067*
H13B	0.3445	0.2603	0.5076	0.067*
C14	0.1048 (4)	0.11929 (15)	0.39918 (13)	0.0503 (4)
C17	0.0146 (7)	−0.1107 (2)	0.2654 (2)	0.0886 (8)
H17	−0.0175	−0.1874	0.2201	0.106*
C15'	−0.041 (2)	0.0839 (7)	0.3020 (6)	0.0552 (16)	0.480 (17)
H15'	−0.1176	0.1395	0.2818	0.066*	0.480 (17)
C16'	−0.078 (2)	−0.0291 (7)	0.2348 (7)	0.072 (2)	0.480 (17)
H16'	−0.1655	−0.0486	0.1690	0.086*	0.480 (17)
C18'	0.143 (3)	−0.0844 (7)	0.3605 (9)	0.085 (2)	0.480 (17)
H18'	0.2015	−0.1430	0.3805	0.103*	0.480 (17)
C19'	0.187 (2)	0.0299 (5)	0.4283 (6)	0.0656 (19)	0.480 (17)
H19'	0.2726	0.0471	0.4941	0.079*	0.480 (17)
C15	−0.125 (2)	0.0841 (7)	0.3299 (9)	0.070 (2)	0.520 (17)
H15	−0.2481	0.1365	0.3260	0.085*	0.520 (17)
C16	−0.177 (3)	−0.0309 (8)	0.2637 (9)	0.092 (3)	0.520 (17)
H16	−0.3414	−0.0559	0.2175	0.110*	0.520 (17)
C18	0.249 (2)	−0.0711 (8)	0.3364 (9)	0.093 (2)	0.520 (17)
H18	0.3755	−0.1223	0.3410	0.111*	0.520 (17)
C19	0.302 (2)	0.0446 (5)	0.4016 (7)	0.0728 (18)	0.520 (17)
H19	0.4686	0.0717	0.4466	0.087*	0.520 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0510 (8)	0.0380 (6)	0.0337 (6)	0.0102 (5)	0.0050 (5)	0.0110 (5)
O1	0.0833 (9)	0.0519 (7)	0.0505 (7)	0.0265 (6)	0.0074 (6)	0.0225 (5)
O11	0.0917 (10)	0.0418 (6)	0.0484 (7)	0.0205 (6)	0.0270 (6)	0.0107 (5)
N2	0.0609 (9)	0.0457 (7)	0.0354 (6)	0.0132 (6)	0.0033 (5)	0.0148 (5)
N3	0.0569 (8)	0.0424 (7)	0.0361 (6)	0.0138 (6)	0.0106 (5)	0.0140 (5)
C1	0.0403 (8)	0.0397 (7)	0.0357 (7)	0.0066 (6)	0.0059 (5)	0.0107 (6)
C2	0.0445 (9)	0.0535 (9)	0.0443 (8)	0.0132 (7)	0.0060 (6)	0.0163 (7)
C3	0.0554 (11)	0.0586 (10)	0.0576 (10)	0.0254 (8)	0.0126 (8)	0.0173 (8)
C4	0.0684 (12)	0.0570 (10)	0.0483 (9)	0.0220 (9)	0.0181 (8)	0.0087 (8)
C5	0.0624 (11)	0.0537 (9)	0.0365 (7)	0.0121 (8)	0.0093 (7)	0.0114 (7)
C6	0.0476 (9)	0.0413 (7)	0.0380 (7)	0.0079 (6)	0.0072 (6)	0.0144 (6)
C7	0.0616 (10)	0.0388 (7)	0.0418 (7)	0.0105 (7)	0.0108 (7)	0.0196 (6)
C8	0.0646 (10)	0.0370 (7)	0.0425 (8)	0.0077 (7)	0.0054 (7)	0.0126 (6)
C11	0.0482 (9)	0.0390 (7)	0.0323 (6)	0.0072 (6)	0.0034 (6)	0.0080 (5)
C12	0.0476 (9)	0.0442 (8)	0.0352 (7)	0.0124 (6)	0.0044 (6)	0.0132 (6)
C13	0.0809 (13)	0.0517 (9)	0.0382 (8)	0.0133 (8)	0.0079 (8)	0.0202 (7)
C14	0.0615 (11)	0.0476 (9)	0.0486 (9)	0.0132 (7)	0.0129 (7)	0.0230 (7)
C17	0.116 (2)	0.0470 (11)	0.0933 (19)	0.0091 (12)	0.0246 (16)	0.0120 (11)
C15'	0.071 (5)	0.046 (2)	0.049 (3)	0.013 (3)	0.006 (2)	0.015 (2)
C16'	0.092 (6)	0.049 (3)	0.062 (3)	0.003 (3)	0.015 (3)	0.007 (2)
C18'	0.106 (7)	0.055 (3)	0.115 (6)	0.030 (4)	0.029 (5)	0.047 (3)
C19'	0.076 (5)	0.065 (3)	0.073 (3)	0.025 (3)	0.010 (3)	0.040 (2)
C15	0.071 (5)	0.052 (2)	0.082 (6)	0.013 (3)	0.000 (3)	0.018 (3)
C16	0.095 (6)	0.067 (3)	0.093 (6)	−0.008 (4)	−0.013 (4)	0.013 (4)
C18	0.095 (6)	0.066 (4)	0.128 (6)	0.039 (4)	0.040 (4)	0.035 (4)
C19	0.068 (4)	0.066 (3)	0.090 (4)	0.017 (2)	0.010 (3)	0.031 (3)

Geometric parameters (Å, º) top

N1—C11	1.3743 (19)	C12—H12B	0.9700
N1—C1	1.4247 (18)	C13—C14	1.509 (2)
N1—C8	1.4593 (19)	C13—H13A	0.9700
O1—C7	1.230 (2)	C13—H13B	0.9700
O11—C11	1.2230 (19)	C14—C15	1.337 (10)
N2—C7	1.342 (2)	C14—C19	1.387 (6)
N2—C6	1.399 (2)	C14—C15'	1.394 (9)
N2—H2N	0.8824	C14—C19'	1.395 (5)
N3—C12	1.450 (2)	C17—C16'	1.335 (10)
N3—C13	1.456 (2)	C17—C18'	1.349 (11)
N3—H3N	0.9049	C17—C18	1.369 (11)
C1—C2	1.383 (2)	C17—C16	1.414 (11)
C1—C6	1.399 (2)	C17—H17	0.9300
C2—C3	1.385 (2)	C15'—C16'	1.373 (11)
C2—H2	0.9300	C15'—H15'	0.9300
C3—C4	1.380 (3)	C16'—H16'	0.9300
C3—H3	0.9300	C18'—C19'	1.387 (11)
C4—C5	1.377 (3)	C18'—H18'	0.9300
C4—H4	0.9300	C19'—H19'	0.9300
C5—C6	1.387 (2)	C15—C16	1.388 (12)
C5—H5	0.9300	C15—H15	0.9300
C7—C8	1.510 (2)	C16—H16	0.9300
C8—H8A	0.9700	C18—C19	1.391 (11)
C8—H8B	0.9700	C18—H18	0.9300
C11—C12	1.509 (2)	C19—H19	0.9300
C12—H12A	0.9700

C11—N1—C1	125.98 (12)	H12A—C12—H12B	108.3
C11—N1—C8	118.09 (13)	N3—C13—C14	113.35 (13)
C1—N1—C8	114.39 (12)	N3—C13—H13A	108.9
C7—N2—C6	123.31 (14)	C14—C13—H13A	108.9
C7—N2—H2N	115.6	N3—C13—H13B	108.9
C6—N2—H2N	121.0	C14—C13—H13B	108.9
C12—N3—C13	113.15 (13)	H13A—C13—H13B	107.7
C12—N3—H3N	107.7	C15—C14—C19	121.0 (5)
C13—N3—H3N	112.2	C15'—C14—C19'	115.3 (4)
C2—C1—C6	119.70 (14)	C15—C14—C13	118.9 (4)
C2—C1—N1	124.13 (13)	C19—C14—C13	120.0 (3)
C6—C1—N1	116.17 (13)	C15'—C14—C13	123.8 (4)
C1—C2—C3	119.80 (15)	C19'—C14—C13	120.7 (3)
C1—C2—H2	120.1	C16'—C17—C18'	121.5 (5)
C3—C2—H2	120.1	C18—C17—C16	117.6 (5)
C4—C3—C2	120.51 (16)	C16'—C17—H17	118.1
C4—C3—H3	119.7	C18'—C17—H17	120.4
C2—C3—H3	119.7	C18—C17—H17	121.2
C5—C4—C3	119.98 (16)	C16—C17—H17	121.2
C5—C4—H4	120.0	C16'—C15'—C14	123.0 (8)
C3—C4—H4	120.0	C16'—C15'—H15'	118.5
C4—C5—C6	120.24 (16)	C14—C15'—H15'	118.5
C4—C5—H5	119.9	C17—C16'—C15'	118.9 (8)
C6—C5—H5	119.9	C17—C16'—H16'	120.6
C5—C6—C1	119.70 (15)	C15'—C16'—H16'	120.6
C5—C6—N2	120.69 (14)	C17—C18'—C19'	120.2 (6)
C1—C6—N2	119.58 (14)	C17—C18'—H18'	119.9
O1—C7—N2	122.90 (15)	C19'—C18'—H18'	119.9
O1—C7—C8	122.08 (15)	C18'—C19'—C14	120.8 (6)
N2—C7—C8	115.00 (14)	C18'—C19'—H19'	119.6
N1—C8—C7	110.73 (13)	C14—C19'—H19'	119.6
N1—C8—H8A	109.5	C14—C15—C16	119.7 (8)
C7—C8—H8A	109.5	C14—C15—H15	120.1
N1—C8—H8B	109.5	C16—C15—H15	120.1
C7—C8—H8B	109.5	C15—C16—C17	120.9 (8)
H8A—C8—H8B	108.1	C15—C16—H16	119.5
O11—C11—N1	119.82 (14)	C17—C16—H16	119.5
O11—C11—C12	120.36 (14)	C17—C18—C19	121.0 (7)
N1—C11—C12	119.81 (13)	C17—C18—H18	119.5
N3—C12—C11	109.11 (12)	C19—C18—H18	119.5
N3—C12—H12A	109.9	C14—C19—C18	119.5 (6)
C11—C12—H12A	109.9	C14—C19—H19	120.3
N3—C12—H12B	109.9	C18—C19—H19	120.3
C11—C12—H12B	109.9

C11—N1—C1—C2	−50.3 (2)	N3—C13—C14—C19'	167.4 (6)
C8—N1—C1—C2	144.16 (16)	C15—C14—C15'—C16'	−95.3 (18)
C11—N1—C1—C6	130.61 (16)	C19—C14—C15'—C16'	25.8 (8)
C8—N1—C1—C6	−34.89 (19)	C19'—C14—C15'—C16'	−6.4 (8)
C6—C1—C2—C3	−3.2 (2)	C13—C14—C15'—C16'	179.0 (5)
N1—C1—C2—C3	177.82 (15)	C18'—C17—C16'—C15'	−0.1 (9)
C1—C2—C3—C4	1.9 (3)	C18—C17—C16'—C15'	−30.8 (8)
C2—C3—C4—C5	0.3 (3)	C16—C17—C16'—C15'	73.5 (13)
C3—C4—C5—C6	−1.2 (3)	C14—C15'—C16'—C17	4.3 (10)
C4—C5—C6—C1	−0.1 (3)	C16'—C17—C18'—C19'	−1.4 (10)
C4—C5—C6—N2	−178.06 (16)	C18—C17—C18'—C19'	80.6 (13)
C2—C1—C6—C5	2.2 (2)	C16—C17—C18'—C19'	−29.0 (9)
N1—C1—C6—C5	−178.66 (14)	C17—C18'—C19'—C14	−1.1 (10)
C2—C1—C6—N2	−179.74 (14)	C15—C14—C19'—C18'	30.8 (8)
N1—C1—C6—N2	−0.7 (2)	C19—C14—C19'—C18'	−82.6 (9)
C7—N2—C6—C5	−164.15 (16)	C15'—C14—C19'—C18'	4.7 (8)
C7—N2—C6—C1	17.9 (2)	C13—C14—C19'—C18'	179.5 (5)
C6—N2—C7—O1	−179.41 (15)	C19—C14—C15—C16	4.4 (8)
C6—N2—C7—C8	2.1 (2)	C15'—C14—C15—C16	73.9 (16)
C11—N1—C8—C7	−113.87 (16)	C19'—C14—C15—C16	−28.0 (8)
C1—N1—C8—C7	52.85 (19)	C13—C14—C15—C16	−177.3 (5)
O1—C7—C8—N1	145.30 (16)	C14—C15—C16—C17	−2.7 (11)
N2—C7—C8—N1	−36.2 (2)	C16'—C17—C16—C15	−87.1 (16)
C1—N1—C11—O11	−171.28 (15)	C18'—C17—C16—C15	31.7 (9)
C8—N1—C11—O11	−6.3 (2)	C18—C17—C16—C15	1.7 (10)
C1—N1—C11—C12	9.4 (2)	C16'—C17—C18—C19	27.1 (9)
C8—N1—C11—C12	174.44 (13)	C18'—C17—C18—C19	−85.5 (13)
C13—N3—C12—C11	−163.52 (13)	C16—C17—C18—C19	−2.4 (9)
O11—C11—C12—N3	27.0 (2)	C15—C14—C19—C18	−5.1 (8)
N1—C11—C12—N3	−153.67 (14)	C15'—C14—C19—C18	−29.0 (7)
C12—N3—C13—C14	−73.1 (2)	C19'—C14—C19—C18	76.5 (9)
N3—C13—C14—C15	−45.8 (7)	C13—C14—C19—C18	176.7 (5)
N3—C13—C14—C19	132.5 (6)	C17—C18—C19—C14	4.1 (10)
N3—C13—C14—C15'	−18.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.88	2.00	2.879 (2)	175
N3—H3N···O11	0.90	2.25	2.6804 (18)	109
N3—H3N···O11ⁱⁱ	0.90	2.36	3.056 (2)	134
C2—H2···N3ⁱⁱⁱ	0.93	2.62	3.535 (2)	169
C8—H8B···O11	0.97	2.23	2.682 (2)	107
C17—H17···O1^iv	0.93	2.53	3.422 (3)	161

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

Comparative torsion angles (°) for compound (II) and (IIB). top

Torsion angle	(II)	(IIB)
C8—N1—C11—C12	174.44 (13)	166.0 (5)
N1—C11—C12—N3	-153.67 (14)	-145.6 (5)
C11—C12—N3—C13	-163.52 (13)	65.3 (6)
C12—N3—C13—C14	-73.1 (2)	176.3 (4)
N3—C13—C14—C15	-45.8 (7)	-12.9 (8)
N3—C13—C14—C15"	-18.3 (6)	–

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page