Accurate H-atom parameters for the two polymorphs of L-histi­dine at 5, 105 and 295 K

The crystal structure of the monoclinic polymorph of the primary amino acid L-histi­dine has been determined for the first time by single-crystal neutron diffraction, while that of the orthorhombic polymorph has been reinvestigated with an untwinned crystal, improving the experimental precision and accuracy. For each polymorph, neutron diffraction data were collected at 5, 105 and 295 K. Single-crystal X-ray diffraction experiments were also performed at the same temperatures. The two polymorphs, whose crystal packing is interpreted by intermolecular interaction energies calculated using the Pixel method, show differences in the energy and geometry of the hydrogen bond formed along the c direction. Taking advantage of the X-ray diffraction data collected at 5 K, the precision and accuracy of the new Hirshfeld atom refinement method im­ple­mented in NoSpherA2 were probed choosing various settings of the functionals and basis sets, together with the use of explicit clusters of molecules and enhanced rigid-body restraints for H atoms. Equivalent atomic coordinates and aniso­tropic displacement parameters were com­pared and found to agree well with those obtained from the corresponding neutron structural models.

Computing details

Data collection: MAATEL/ANSTO control program for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02. Cell refinement: LaueG (Piltz, 2011) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; SAINT V8.38A (?, 2016) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Data reduction: argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2011) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; SAINT V8.38A (?, 2016) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Program(s) used to solve structure: from X-ray model at 5 K for HMTN00, HOTN00; from X-ray model at 105 K for HMTN01, HOTN01; from X-ray model at 295 K for HMTN02, HOTN02; ShelXT (Sheldrick, 2015) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Program(s) used to refine structure: XL (Sheldrick, 2008) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; SHELXL (Sheldrick, 2015) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Molecular graphics: Olex2 1.3 (Dolomanov et al., 2009) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; Olex2 (Dolomanov et al., 2009) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; Olex2 (Dolomanov et al., 2009) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23.

2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HMTN00)

Crystal data

C6H9N3O2	F(000) = 92
Mr = 155.16	Dx = 1.464 Mg m^−3
Monoclinic, P21	Neutron radiation, λ = 0.80 Å
a = 5.1651 (2) Å	Cell parameters from 4301 reflections
b = 7.2324 (2) Å	θ = 3.6–30.5°
c = 9.4957 (3) Å	µ = 0.0 mm^−1
β = 97.065 (2)°	T = 5 K
V = 352.03 (2) Å^3	Plate, colourless
Z = 2	0.45 × 0.35 × 0.30 mm

Data collection

KOALA diffractometer	Rint = 0.138
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia	θmax = 71.1°
Laue scans	h = −9→9
16604 measured reflections	k = −13→13
1629 independent reflections	l = −15→15
1267 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max < 0.001
S = 1.21	Δρmax = 1.62 e Å^−3
1629 reflections	Δρmin = −1.99 e Å^−3
181 parameters	Absolute structure: Absolute structure known from synthesis
1 restraint

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.

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

	x	y	z	Uiso*/Ueq
O2	0.3153 (3)	0.4532 (3)	1.0159 (2)	0.0075 (4)
O1	0.7418 (3)	0.4476 (3)	1.0990 (3)	0.0089 (4)
N1	0.8766 (2)	0.63531 (16)	0.87289 (15)	0.0071 (3)
H1A	0.9462 (7)	0.6394 (6)	0.7740 (5)	0.0197 (8)
H1B	1.0169 (7)	0.5658 (5)	0.9425 (5)	0.0218 (9)
H1C	0.8500 (8)	0.7702 (5)	0.9113 (5)	0.0201 (8)
N3	0.7208 (2)	0.44435 (18)	0.38771 (17)	0.0079 (3)
H3	0.6899 (7)	0.4374 (6)	0.2770 (5)	0.0203 (8)
N2	0.9220 (2)	0.51526 (17)	0.60102 (15)	0.0074 (3)
C1	0.5534 (3)	0.4757 (2)	1.0048 (2)	0.0052 (3)
C4	0.6990 (3)	0.4138 (2)	0.6167 (2)	0.0069 (4)
C6	0.5721 (3)	0.3694 (2)	0.4843 (2)	0.0069 (3)
H6	0.3963 (8)	0.2908 (6)	0.4535 (6)	0.0232 (9)
C2	0.6204 (3)	0.5360 (2)	0.8578 (2)	0.0056 (3)
H2	0.4702 (6)	0.6330 (6)	0.8096 (5)	0.0189 (8)
C5	0.9266 (3)	0.5300 (3)	0.4619 (2)	0.0076 (3)
H5	1.0729 (8)	0.6031 (6)	0.4118 (6)	0.0244 (10)
C3	0.6302 (3)	0.3659 (2)	0.7616 (2)	0.0066 (3)
H3A	0.7723 (8)	0.2667 (6)	0.8134 (5)	0.0214 (9)
H3B	0.4375 (8)	0.2981 (6)	0.7524 (6)	0.0248 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0047 (6)	0.0086 (8)	0.0093 (13)	0.0003 (6)	0.0014 (6)	0.0016 (7)
O1	0.0054 (6)	0.0104 (8)	0.0104 (12)	0.0007 (6)	−0.0010 (6)	0.0013 (8)
N1	0.0066 (4)	0.0055 (5)	0.0093 (8)	−0.0006 (3)	0.0011 (4)	−0.0005 (4)
H1A	0.0160 (13)	0.0258 (19)	0.018 (3)	−0.0037 (13)	0.0057 (14)	−0.0005 (17)
H1B	0.0184 (14)	0.0194 (19)	0.026 (3)	0.0011 (12)	−0.0021 (15)	0.0066 (16)
H1C	0.0250 (16)	0.0116 (16)	0.023 (3)	−0.0007 (12)	0.0018 (16)	−0.0034 (14)
N3	0.0074 (4)	0.0089 (5)	0.0074 (9)	−0.0005 (4)	0.0004 (4)	0.0003 (4)
H3	0.0240 (15)	0.026 (2)	0.010 (3)	−0.0033 (15)	−0.0010 (14)	−0.0005 (15)
N2	0.0059 (4)	0.0085 (5)	0.0078 (8)	−0.0015 (4)	0.0002 (4)	−0.0007 (5)
C1	0.0060 (5)	0.0053 (7)	0.0046 (11)	0.0002 (5)	0.0015 (5)	0.0002 (5)
C4	0.0055 (5)	0.0069 (7)	0.0080 (11)	−0.0010 (5)	−0.0003 (5)	0.0001 (6)
C6	0.0067 (5)	0.0079 (7)	0.0061 (11)	−0.0017 (5)	0.0009 (6)	−0.0007 (6)
H6	0.0176 (15)	0.031 (2)	0.020 (3)	−0.0109 (14)	−0.0014 (15)	−0.0011 (17)
C2	0.0053 (5)	0.0054 (7)	0.0060 (10)	0.0002 (5)	0.0002 (5)	0.0012 (6)
H2	0.0144 (12)	0.0192 (17)	0.022 (3)	0.0052 (12)	−0.0012 (14)	0.0029 (15)
C5	0.0070 (5)	0.0084 (7)	0.0079 (11)	−0.0015 (5)	0.0025 (6)	−0.0002 (6)
H5	0.0215 (15)	0.028 (2)	0.026 (3)	−0.0107 (14)	0.0098 (16)	0.0017 (17)
C3	0.0086 (5)	0.0060 (7)	0.0053 (10)	−0.0023 (5)	0.0016 (6)	−0.0005 (6)
H3A	0.0301 (18)	0.0166 (18)	0.017 (3)	0.0072 (14)	0.0012 (16)	−0.0004 (14)
H3B	0.0210 (16)	0.025 (2)	0.029 (3)	−0.0139 (14)	0.0057 (17)	−0.0048 (17)

Geometric parameters (Å, º)

O2—C1	1.258 (2)	N2—C5	1.329 (2)
O1—C1	1.255 (3)	C1—C2	1.542 (3)
N1—H1A	1.046 (5)	C4—C6	1.382 (3)
N1—H1B	1.047 (4)	C4—C3	1.503 (3)
N1—H1C	1.056 (4)	C2—H2	1.103 (4)
N1—C2	1.4970 (19)	C2—C3	1.537 (2)
N3—H3	1.045 (5)	C6—H6	1.081 (5)
N3—C6	1.378 (2)	C3—H3A	1.098 (5)
N3—C5	1.351 (2)	C3—H3B	1.103 (4)
N2—C4	1.3891 (19)	C5—H5	1.080 (5)
C4—N2—C5	105.40 (14)	C3—C2—H2	109.6 (3)
O1—C1—C2	116.78 (16)	C4—C3—H3A	109.9 (3)
N1—C2—C3	110.34 (13)	N2—C5—H5	125.2 (3)
N2—C4—C3	120.82 (15)	C4—C6—H6	131.1 (3)
N2—C5—N3	111.87 (15)	O1—C1—O2	126.9 (2)
C2—N1—H1A	109.0 (3)	N1—C2—C1	110.08 (14)
C5—N3—H3	124.0 (2)	C2—C3—C4	112.85 (13)
C1—C2—H2	109.3 (3)	C3—C4—C6	129.79 (14)
C2—C3—H3B	107.9 (3)	C2—N1—H1C	109.0 (2)
N3—C6—H6	123.1 (3)	N1—C2—H2	107.6 (2)
C5—N3—C6	107.49 (15)	C2—C3—H3A	109.0 (3)
O2—C1—C2	116.30 (16)	C4—C3—H3B	110.0 (3)
C1—C2—C3	109.83 (12)	N3—C5—H5	122.9 (3)
N2—C4—C6	109.39 (15)	H1B—N1—H1C	109.6 (3)
N3—C6—C4	105.86 (14)	H1A—N1—H1C	110.9 (4)
C2—N1—H1B	111.4 (2)	H1A—N1—H1B	107.0 (3)
C6—N3—H3	128.5 (2)	H3A—C3—H3B	107.0 (3)
C5—N2—C4—C3	178.96 (15)	O1—C1—C2—N1	−27.5 (2)
C6—N3—C5—N2	0.2 (2)	O2—C1—C2—C3	−83.19 (19)
O1—C1—C2—C3	94.23 (19)	C2—C3—C4—N2	53.59 (19)
N1—C2—C3—C4	−57.55 (18)	C3—C4—C6—N3	−178.75 (14)
C2—C3—C4—C6	−127.54 (17)	H1A—N1—C2—H2	−78.0 (4)
H1A—N1—C2—C1	162.9 (3)	H1B—N1—C2—H2	164.2 (4)
H1B—N1—C2—C1	45.1 (3)	H1C—N1—C2—H2	43.2 (4)
H1C—N1—C2—C1	−75.9 (3)	H3—N3—C5—N2	−178.7 (3)
C4—N2—C5—H5	178.8 (3)	H3—N3—C6—C4	178.6 (3)
H3—N3—C5—H5	2.4 (5)	O2—C1—C2—H2	37.1 (3)
H3—N3—C6—H6	−0.2 (5)	N1—C2—C3—H3A	64.9 (3)
C5—N2—C4—C6	−0.12 (17)	C1—C2—C3—H3B	59.2 (3)
C5—N3—C6—C4	−0.23 (17)	H2—C2—C3—H3B	−61.0 (4)
O2—C1—C2—N1	155.13 (16)	H3B—C3—C4—N2	174.2 (3)
C1—C2—C3—C4	−179.07 (13)	C3—C4—C6—H6	−0.1 (4)
N2—C4—C6—N3	0.22 (16)	N1—C2—C3—H3B	−179.3 (3)
H1A—N1—C2—C3	41.5 (3)	H2—C2—C3—C4	60.8 (3)
H1B—N1—C2—C3	−76.3 (3)	H3A—C3—C4—N2	−68.3 (3)
H1C—N1—C2—C3	162.7 (3)	H3B—C3—C4—C6	−7.0 (3)
C6—N3—C5—H5	−178.7 (3)	C1—C2—C3—H3A	−56.7 (3)
C5—N3—C6—H6	−179.0 (3)	H2—C2—C3—H3A	−176.8 (3)
O1—C1—C2—H2	−145.5 (3)	H3A—C3—C4—C6	110.6 (3)
C4—N2—C5—N3	0.0 (2)	N2—C4—C6—H6	178.8 (3)

2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HMTN01)

Crystal data

C6H9N3O2	F(000) = 92
Mr = 155.16	Dx = 1.455 Mg m^−3
Monoclinic, P21	Neutron radiation, λ = 0.80 Å
a = 5.1656 (2) Å	Cell parameters from 2706 reflections
b = 7.2761 (3) Å	θ = 3.5–30.4°
c = 9.4978 (3) Å	µ = 0.0 mm^−1
β = 97.316 (3)°	T = 105 K
V = 354.07 (2) Å^3	Plate, colourless
Z = 2	0.45 × 0.35 × 0.30 mm

Data collection

KOALA diffractometer	Rint = 0.149
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia	θmax = 70.9°
Laue scans	h = −8→8
12588 measured reflections	k = −12→12
1359 independent reflections	l = −14→14
939 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.071	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 1.12 e Å^−3
1292 reflections	Δρmin = −1.18 e Å^−3
181 parameters	Absolute structure: Absolute structure known from synthesis
1 restraint

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.

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

	x	y	z	Uiso*/Ueq
O2	0.3144 (4)	0.4517 (4)	1.0143 (3)	0.0139 (5)
O1	0.7401 (4)	0.4458 (4)	1.0988 (3)	0.0147 (5)
N1	0.8736 (2)	0.63497 (19)	0.87368 (17)	0.0098 (3)
H1A	0.9437 (8)	0.6399 (7)	0.7747 (5)	0.0230 (9)
H1B	1.0151 (8)	0.5663 (6)	0.9429 (6)	0.0251 (10)
H1C	0.8476 (8)	0.7676 (6)	0.9129 (5)	0.0235 (10)
N3	0.7209 (2)	0.4445 (2)	0.38776 (19)	0.0131 (3)
H3	0.6915 (8)	0.4363 (7)	0.2760 (6)	0.0245 (10)
N2	0.9212 (2)	0.5163 (2)	0.60161 (18)	0.0132 (3)
C1	0.5529 (3)	0.4744 (2)	1.0041 (2)	0.0088 (4)
C4	0.6986 (3)	0.4149 (3)	0.6164 (2)	0.0108 (4)
C6	0.5727 (3)	0.3695 (3)	0.4839 (2)	0.0125 (4)
H6	0.3972 (9)	0.2917 (7)	0.4537 (6)	0.0306 (11)
C2	0.6190 (3)	0.5354 (3)	0.8574 (2)	0.0089 (4)
H2	0.4688 (7)	0.6316 (7)	0.8087 (5)	0.0225 (9)
C5	0.9261 (3)	0.5314 (3)	0.4625 (2)	0.0128 (4)
H5	1.0719 (9)	0.6041 (7)	0.4124 (6)	0.0327 (12)
C3	0.6304 (4)	0.3662 (3)	0.7604 (2)	0.0116 (4)
H3A	0.7735 (10)	0.2668 (7)	0.8138 (6)	0.0288 (11)
H3B	0.4390 (10)	0.2999 (7)	0.7520 (6)	0.0309 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0100 (7)	0.0187 (12)	0.0132 (16)	−0.0002 (9)	0.0022 (8)	0.0025 (10)
O1	0.0139 (8)	0.0213 (11)	0.0092 (14)	−0.0004 (9)	0.0025 (8)	0.0036 (10)
N1	0.0111 (5)	0.0108 (7)	0.0074 (10)	−0.0014 (4)	0.0012 (5)	0.0003 (5)
H1A	0.0250 (16)	0.033 (2)	0.012 (3)	−0.0058 (17)	0.0078 (17)	−0.001 (2)
H1B	0.0232 (17)	0.026 (2)	0.024 (3)	−0.0007 (15)	−0.0052 (18)	0.0060 (18)
H1C	0.0269 (18)	0.018 (2)	0.025 (3)	−0.0013 (15)	0.0016 (18)	−0.0078 (17)
N3	0.0169 (5)	0.0152 (7)	0.0075 (11)	0.0006 (5)	0.0030 (6)	0.0013 (5)
H3	0.0302 (17)	0.032 (2)	0.011 (3)	−0.0014 (19)	0.0007 (17)	−0.0032 (19)
N2	0.0134 (5)	0.0165 (7)	0.0097 (10)	−0.0030 (5)	0.0016 (5)	−0.0004 (6)
C1	0.0093 (6)	0.0101 (9)	0.0072 (13)	0.0012 (6)	0.0022 (7)	0.0015 (6)
C4	0.0125 (7)	0.0113 (10)	0.0091 (14)	−0.0005 (6)	0.0025 (7)	0.0004 (7)
C6	0.0132 (7)	0.0130 (9)	0.0113 (14)	−0.0017 (7)	0.0009 (7)	−0.0024 (8)
H6	0.0273 (19)	0.039 (3)	0.024 (3)	−0.0147 (18)	−0.0010 (19)	−0.006 (2)
C2	0.0102 (6)	0.0098 (8)	0.0067 (11)	−0.0001 (6)	0.0005 (6)	0.0017 (7)
H2	0.0233 (15)	0.024 (2)	0.020 (3)	0.0064 (16)	0.0005 (17)	0.0056 (18)
C5	0.0154 (7)	0.0150 (9)	0.0083 (13)	−0.0011 (7)	0.0032 (8)	0.0021 (8)
H5	0.033 (2)	0.045 (3)	0.021 (3)	−0.013 (2)	0.009 (2)	0.004 (2)
C3	0.0169 (7)	0.0101 (9)	0.0082 (13)	−0.0026 (7)	0.0026 (8)	−0.0010 (8)
H3A	0.045 (2)	0.019 (2)	0.023 (3)	0.0102 (18)	0.008 (2)	0.0049 (18)
H3B	0.035 (2)	0.036 (3)	0.024 (3)	−0.0228 (19)	0.011 (2)	−0.008 (2)

Geometric parameters (Å, º)

O1—C1	1.251 (3)	C1—C2	1.542 (3)
N2—C5	1.329 (3)	N1—H1A	1.050 (5)
C2—C3	1.543 (3)	C2—H2	1.102 (5)
O2—C1	1.259 (3)	C6—H6	1.076 (5)
N3—C5	1.355 (2)	N1—H1B	1.046 (5)
C3—C4	1.498 (3)	C3—H3A	1.110 (6)
N1—C2	1.492 (2)	N1—H1C	1.049 (5)
N3—C6	1.377 (2)	C3—H3B	1.094 (6)
C4—C6	1.381 (3)	N3—H3	1.055 (6)
N2—C4	1.388 (2)	C5—H5	1.079 (5)
C4—N2—C5	105.39 (15)	C3—C2—H2	109.5 (3)
O1—C1—C2	117.24 (17)	C4—C3—H3A	110.6 (3)
N1—C2—C3	110.43 (14)	N2—C5—H5	125.6 (3)
N2—C4—C3	120.82 (17)	C4—C6—H6	130.7 (3)
N2—C5—N3	111.69 (15)	O1—C1—O2	126.7 (2)
C2—N1—H1A	108.9 (3)	N1—C2—C1	109.87 (14)
C5—N3—H3	123.8 (3)	C2—C3—C4	112.81 (17)
C1—C2—H2	109.7 (3)	C3—C4—C6	129.59 (17)
C2—C3—H3B	107.0 (3)	C2—N1—H1C	109.4 (3)
N3—C6—H6	123.5 (3)	N1—C2—H2	107.4 (3)
C5—N3—C6	107.55 (16)	C2—C3—H3A	108.7 (3)
O2—C1—C2	116.04 (19)	C4—C3—H3B	110.7 (3)
C1—C2—C3	109.85 (16)	N3—C5—H5	122.8 (3)
N2—C4—C6	109.57 (16)	H1A—N1—H1B	106.6 (4)
N3—C6—C4	105.81 (15)	H3A—C3—H3B	106.8 (4)
C2—N1—H1B	111.7 (3)	H1A—N1—H1C	111.1 (4)
C6—N3—H3	128.6 (3)	H1B—N1—H1C	109.1 (4)
C5—N2—C4—C3	178.71 (18)	O1—C1—C2—N1	−27.8 (3)
C6—N3—C5—N2	0.4 (2)	O2—C1—C2—C3	−83.5 (2)
O1—C1—C2—C3	93.9 (2)	C2—C3—C4—N2	53.8 (2)
N1—C2—C3—C4	−57.6 (2)	C3—C4—C6—N3	−178.28 (19)
C2—C3—C4—C6	−128.1 (2)	H1A—N1—C2—H2	−77.9 (4)
H1A—N1—C2—C1	162.9 (3)	H1B—N1—C2—H2	164.7 (4)
H1B—N1—C2—C1	45.4 (4)	H1C—N1—C2—H2	43.8 (4)
H1C—N1—C2—C1	−75.5 (3)	H3—N3—C5—N2	−178.0 (3)
C4—N2—C5—H5	179.0 (4)	H3—N3—C6—C4	178.1 (4)
H3—N3—C5—H5	2.6 (5)	O2—C1—C2—H2	37.0 (4)
H3—N3—C6—H6	−1.4 (6)	N1—C2—C3—H3A	65.4 (4)
C5—N2—C4—C6	0.3 (2)	C1—C2—C3—H3B	59.1 (4)
C5—N3—C6—C4	−0.2 (2)	H2—C2—C3—H3B	−61.5 (4)
O2—C1—C2—N1	154.83 (19)	H3B—C3—C4—N2	173.7 (3)
C1—C2—C3—C4	−178.98 (14)	C3—C4—C6—H6	1.2 (5)
N2—C4—C6—N3	−0.1 (2)	N1—C2—C3—H3B	−179.6 (3)
H1A—N1—C2—C3	41.5 (3)	H2—C2—C3—C4	60.5 (3)
H1B—N1—C2—C3	−75.9 (4)	H3A—C3—C4—N2	−68.1 (4)
H1C—N1—C2—C3	163.2 (3)	H3B—C3—C4—C6	−8.2 (4)
C6—N3—C5—H5	−179.0 (4)	C1—C2—C3—H3A	−56.0 (3)
C5—N3—C6—H6	−179.7 (4)	H2—C2—C3—H3A	−176.5 (4)
O1—C1—C2—H2	−145.7 (3)	H3A—C3—C4—C6	109.9 (4)
C4—N2—C5—N3	−0.5 (2)	N2—C4—C6—H6	179.4 (4)

2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HMTN02)

Crystal data

C6H9N3O2	F(000) = 92
Mr = 155.16	Dx = 1.428 Mg m^−3
Monoclinic, P21	Neutron radiation, λ = 0.80 Å
a = 5.1854 (8) Å	Cell parameters from 2412 reflections
b = 7.3998 (10) Å	θ = 3.5–30.2°
c = 9.4976 (12) Å	µ = 0.0 mm^−1
β = 98.182 (10)°	T = 295 K
V = 360.72 (9) Å^3	Plate, colourless
Z = 2	0.45 × 0.35 × 0.30 mm

Data collection

KOALA diffractometer	Rint = 0.134
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia	θmax = 71.1°
Laue scans	h = −8→8
20381 measured reflections	k = −12→12
1354 independent reflections	l = −14→14
914 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.075	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.77 e Å^−3
1354 reflections	Δρmin = −1.00 e Å^−3
181 parameters	Absolute structure: Absolute structure known from synthesis
1 restraint

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.

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

	x	y	z	Uiso*/Ueq
O2	0.3140 (4)	0.4452 (4)	1.0099 (3)	0.0370 (6)
O1	0.7363 (4)	0.4425 (5)	1.0976 (3)	0.0390 (6)
N1	0.8685 (2)	0.63321 (18)	0.87612 (15)	0.0248 (3)
H1A	0.9374 (7)	0.6423 (7)	0.7783 (5)	0.0418 (9)
H1B	1.0086 (8)	0.5653 (6)	0.9439 (5)	0.0440 (10)
H1C	0.8387 (9)	0.7618 (6)	0.9167 (5)	0.0427 (10)
N3	0.7224 (3)	0.4469 (2)	0.38768 (18)	0.0328 (3)
H3	0.6923 (9)	0.4379 (7)	0.2775 (5)	0.0466 (10)
N2	0.9193 (3)	0.5192 (2)	0.60256 (16)	0.0327 (3)
C1	0.5499 (3)	0.4701 (2)	1.0022 (2)	0.0235 (4)
C4	0.7008 (3)	0.4168 (2)	0.6159 (2)	0.0259 (4)
C6	0.5766 (4)	0.3713 (3)	0.4831 (2)	0.0313 (4)
H6	0.4032 (11)	0.2932 (9)	0.4506 (6)	0.0630 (14)
C2	0.6168 (3)	0.5329 (2)	0.85666 (19)	0.0216 (3)
H2	0.4651 (7)	0.6251 (6)	0.8071 (5)	0.0412 (9)
C5	0.9234 (4)	0.5343 (3)	0.4633 (2)	0.0338 (5)
H5	1.0673 (11)	0.6101 (9)	0.4149 (6)	0.0662 (16)
C3	0.6338 (4)	0.3682 (3)	0.7597 (2)	0.0300 (4)
H3A	0.7794 (12)	0.2737 (7)	0.8139 (6)	0.0565 (14)
H3B	0.4455 (12)	0.2979 (8)	0.7484 (6)	0.0641 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0277 (8)	0.0461 (13)	0.0394 (17)	0.0012 (10)	0.0122 (9)	0.0168 (12)
O1	0.0322 (10)	0.0660 (15)	0.0190 (14)	0.0030 (12)	0.0038 (9)	0.0093 (12)
N1	0.0275 (6)	0.0273 (7)	0.0202 (9)	−0.0043 (5)	0.0053 (6)	−0.0020 (5)
H1A	0.0407 (17)	0.052 (2)	0.035 (3)	−0.0099 (18)	0.0123 (18)	0.004 (2)
H1B	0.041 (2)	0.052 (3)	0.037 (3)	−0.0032 (17)	−0.0010 (19)	0.0026 (19)
H1C	0.053 (2)	0.034 (2)	0.040 (3)	−0.0062 (17)	0.0053 (19)	−0.0093 (17)
N3	0.0431 (7)	0.0371 (7)	0.0190 (10)	0.0009 (6)	0.0077 (6)	0.0008 (6)
H3	0.059 (2)	0.053 (3)	0.027 (3)	0.003 (2)	0.0039 (19)	−0.002 (2)
N2	0.0377 (6)	0.0410 (8)	0.0205 (9)	−0.0086 (6)	0.0077 (6)	−0.0009 (6)
C1	0.0254 (6)	0.0284 (9)	0.0180 (11)	0.0026 (7)	0.0070 (6)	0.0033 (6)
C4	0.0331 (8)	0.0263 (10)	0.0193 (12)	−0.0032 (7)	0.0076 (7)	−0.0015 (7)
C6	0.0375 (10)	0.0364 (10)	0.0196 (13)	−0.0054 (8)	0.0030 (8)	−0.0030 (8)
H6	0.063 (3)	0.079 (4)	0.046 (4)	−0.030 (3)	0.004 (2)	−0.010 (3)
C2	0.0247 (6)	0.0244 (8)	0.0164 (10)	−0.0006 (7)	0.0052 (6)	0.0026 (7)
H2	0.0376 (17)	0.044 (2)	0.042 (3)	0.0065 (17)	0.0062 (17)	0.0107 (19)
C5	0.0404 (9)	0.0402 (10)	0.0236 (13)	−0.0048 (9)	0.0135 (9)	0.0006 (9)
H5	0.070 (3)	0.091 (4)	0.043 (3)	−0.028 (3)	0.026 (3)	0.006 (3)
C3	0.0460 (10)	0.0249 (9)	0.0204 (12)	−0.0072 (8)	0.0090 (9)	−0.0008 (7)
H3A	0.096 (4)	0.040 (2)	0.036 (3)	0.019 (2)	0.018 (3)	0.0076 (19)
H3B	0.082 (3)	0.073 (3)	0.041 (3)	−0.049 (3)	0.021 (3)	−0.013 (2)

Geometric parameters (Å, º)

O1—C1	1.244 (3)	C3—H3A	1.102 (6)
N2—C5	1.331 (2)	N1—C2	1.4899 (19)
C2—C3	1.538 (3)	N3—C6	1.379 (3)
N1—H1A	1.044 (5)	C4—C6	1.374 (3)
C2—H2	1.096 (4)	N1—H1C	1.046 (5)
C6—H6	1.077 (6)	C3—H3B	1.098 (7)
O2—C1	1.249 (3)	N2—C4	1.384 (2)
N3—C5	1.344 (3)	C1—C2	1.544 (3)
C3—C4	1.500 (3)	N3—H3	1.038 (5)
N1—H1B	1.030 (5)	C5—H5	1.086 (6)
C4—N2—C5	105.43 (16)	C3—C2—H2	109.6 (3)
O1—C1—C2	116.82 (17)	C4—C3—H3A	110.2 (3)
N1—C2—C3	110.20 (14)	N2—C5—H5	125.0 (4)
N2—C4—C3	120.89 (16)	C4—C6—H6	131.2 (4)
N2—C5—N3	111.70 (18)	O1—C1—O2	126.8 (2)
C2—N1—H1A	109.1 (3)	N1—C2—C1	110.08 (14)
C5—N3—H3	124.3 (3)	C2—C3—C4	113.31 (16)
C1—C2—H2	109.5 (3)	C3—C4—C6	129.64 (16)
C2—C3—H3B	107.9 (3)	C2—N1—H1C	109.0 (3)
N3—C6—H6	122.9 (3)	N1—C2—H2	107.8 (2)
C5—N3—C6	107.46 (16)	C2—C3—H3A	108.5 (3)
O2—C1—C2	116.32 (19)	C4—C3—H3B	110.0 (3)
C1—C2—C3	109.69 (13)	N3—C5—H5	123.3 (3)
N2—C4—C6	109.46 (16)	H1A—N1—H1B	106.7 (4)
N3—C6—C4	105.95 (17)	H3A—C3—H3B	106.6 (5)
C2—N1—H1B	111.2 (3)	H1A—N1—H1C	110.9 (4)
C6—N3—H3	128.2 (3)	H1B—N1—H1C	110.0 (4)
C5—N2—C4—C3	178.91 (17)	O1—C1—C2—N1	−28.1 (3)
C6—N3—C5—N2	0.5 (2)	O2—C1—C2—C3	−83.8 (2)
O1—C1—C2—C3	93.4 (2)	C2—C3—C4—N2	53.9 (2)
N1—C2—C3—C4	−58.10 (19)	C3—C4—C6—N3	−178.46 (17)
C2—C3—C4—C6	−127.7 (2)	H1A—N1—C2—H2	−76.7 (4)
H1A—N1—C2—C1	163.9 (3)	H1B—N1—C2—H2	165.9 (4)
H1B—N1—C2—C1	46.6 (3)	H1C—N1—C2—H2	44.5 (4)
H1C—N1—C2—C1	−74.9 (3)	H3—N3—C5—N2	−177.8 (4)
C4—N2—C5—H5	178.2 (5)	H3—N3—C6—C4	177.9 (4)
H3—N3—C5—H5	3.5 (6)	O2—C1—C2—H2	36.5 (3)
H3—N3—C6—H6	−1.7 (6)	N1—C2—C3—H3A	64.6 (4)
C5—N2—C4—C6	0.2 (2)	C1—C2—C3—H3B	58.4 (4)
C5—N3—C6—C4	−0.4 (2)	H2—C2—C3—H3B	−61.8 (4)
O2—C1—C2—N1	154.78 (19)	H3B—C3—C4—N2	174.8 (4)
C1—C2—C3—C4	−179.46 (14)	C3—C4—C6—H6	1.1 (6)
N2—C4—C6—N3	0.2 (2)	N1—C2—C3—H3B	179.8 (3)
H1A—N1—C2—C3	42.8 (3)	H2—C2—C3—C4	60.4 (3)
H1B—N1—C2—C3	−74.6 (3)	H3A—C3—C4—N2	−67.9 (4)
H1C—N1—C2—C3	164.0 (3)	H3B—C3—C4—C6	−6.7 (4)
C6—N3—C5—H5	−178.1 (4)	C1—C2—C3—H3A	−56.7 (4)
C5—N3—C6—H6	−180.0 (5)	H2—C2—C3—H3A	−176.9 (4)
O1—C1—C2—H2	−146.4 (3)	H3A—C3—C4—C6	110.5 (4)
C4—N2—C5—N3	−0.4 (2)	N2—C4—C6—H6	179.7 (5)

2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HOTN00)

Crystal data

C6H9N3O2	Dx = 1.476 Mg m^−3
Mr = 155.16	Neutron radiation, λ = 0.80 Å
Orthorhombic, P212121	Cell parameters from 7499 reflections
a = 5.1498 (2) Å	θ = 3.0–36.3°
b = 7.1902 (2) Å	µ = 0.0 mm^−1
c = 18.8503 (6) Å	T = 5 K
V = 697.99 (4) Å^3	Needle, colourless
Z = 4	0.35 × 0.30 × 0.15 mm
F(000) = 184

Data collection

KOALA diffractometer	Rint = 0.188
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia	θmax = 71.2°
Laue scans	h = −8→8
33762 measured reflections	k = −12→11
1375 independent reflections	l = −28→28
1133 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.069	(Δ/σ)max < 0.001
S = 1.15	Δρmax = 1.49 e Å^−3
1375 reflections	Δρmin = −1.34 e Å^−3
181 parameters	Absolute structure: Absolute structure known from synthesis
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
O2	0.3252 (3)	0.4947 (3)	0.23962 (11)	0.0082 (4)
O1	0.7328 (3)	0.4917 (3)	0.19749 (13)	0.0081 (4)
N1	0.9182 (2)	0.31158 (16)	0.31208 (8)	0.0076 (3)
N3	0.86952 (19)	0.50364 (16)	0.55338 (8)	0.0074 (2)
N2	1.0322 (2)	0.43916 (15)	0.44681 (8)	0.0076 (2)
C4	0.8030 (3)	0.5395 (2)	0.43874 (10)	0.0064 (3)
C1	0.5658 (3)	0.4701 (2)	0.24520 (9)	0.0062 (3)
C2	0.6666 (3)	0.4137 (2)	0.31917 (10)	0.0050 (3)
C6	0.7008 (3)	0.5791 (2)	0.50449 (10)	0.0065 (3)
C5	1.0628 (3)	0.4205 (2)	0.51652 (10)	0.0076 (3)
C3	0.7027 (3)	0.5874 (2)	0.36619 (10)	0.0073 (3)
H1B	1.0426 (7)	0.3791 (5)	0.2769 (2)	0.0194 (8)
H1C	0.8794 (7)	0.1770 (5)	0.2951 (2)	0.0205 (9)
H1A	1.0122 (6)	0.3102 (6)	0.3610 (2)	0.0177 (8)
H3	0.8478 (6)	0.5046 (6)	0.6090 (2)	0.0193 (8)
H2	0.5255 (6)	0.3176 (5)	0.3444 (2)	0.0169 (7)
H6	0.5285 (7)	0.6556 (6)	0.5201 (3)	0.0247 (9)
H5	1.2224 (7)	0.3478 (6)	0.5415 (2)	0.0240 (9)
H3A	0.8371 (8)	0.6849 (5)	0.3397 (2)	0.0234 (9)
H3B	0.5139 (7)	0.6563 (6)	0.3713 (3)	0.0236 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0045 (7)	0.0086 (8)	0.0114 (12)	−0.0006 (6)	−0.0006 (6)	0.0015 (8)
O1	0.0049 (6)	0.0116 (8)	0.0077 (12)	0.0000 (6)	0.0007 (5)	0.0005 (7)
N1	0.0069 (4)	0.0063 (5)	0.0096 (8)	0.0011 (4)	−0.0004 (4)	−0.0009 (4)
N3	0.0071 (4)	0.0087 (5)	0.0063 (8)	0.0001 (4)	−0.0001 (4)	−0.0012 (5)
N2	0.0063 (4)	0.0078 (5)	0.0087 (7)	0.0018 (3)	0.0003 (4)	−0.0011 (5)
C4	0.0065 (5)	0.0066 (6)	0.0062 (10)	0.0005 (5)	−0.0005 (5)	−0.0010 (6)
C1	0.0053 (6)	0.0053 (6)	0.0079 (10)	−0.0001 (5)	−0.0001 (5)	0.0005 (6)
C2	0.0042 (6)	0.0055 (6)	0.0053 (10)	0.0006 (5)	−0.0002 (5)	−0.0007 (6)
C6	0.0057 (6)	0.0078 (6)	0.0060 (10)	0.0015 (5)	−0.0009 (5)	−0.0009 (6)
C5	0.0067 (6)	0.0085 (7)	0.0078 (10)	0.0018 (6)	0.0000 (6)	0.0002 (6)
C3	0.0082 (6)	0.0050 (6)	0.0086 (10)	0.0018 (5)	−0.0015 (6)	−0.0006 (6)
H1B	0.0186 (16)	0.0177 (15)	0.022 (3)	0.0008 (13)	0.0044 (15)	0.0019 (14)
H1C	0.0211 (15)	0.0122 (15)	0.028 (3)	0.0009 (12)	−0.0011 (14)	−0.0077 (15)
H1A	0.0156 (15)	0.0229 (17)	0.015 (2)	0.0030 (12)	−0.0028 (13)	0.0002 (16)
H3	0.0202 (15)	0.0236 (16)	0.014 (2)	0.0019 (14)	−0.0009 (13)	0.0000 (16)
H2	0.0145 (14)	0.0191 (15)	0.017 (2)	−0.0031 (12)	0.0006 (13)	0.0011 (15)
H6	0.0178 (16)	0.0281 (19)	0.028 (3)	0.0095 (14)	0.0026 (15)	−0.0035 (18)
H5	0.0201 (16)	0.030 (2)	0.022 (3)	0.0099 (14)	−0.0060 (15)	0.0042 (17)
H3A	0.0277 (18)	0.0184 (16)	0.024 (3)	−0.0071 (15)	−0.0020 (16)	0.0056 (16)
H3B	0.0175 (16)	0.030 (2)	0.023 (3)	0.0119 (13)	−0.0027 (15)	−0.0028 (17)

Geometric parameters (Å, º)

O1—C1	1.254 (3)	C3—H3A	1.105 (4)
N2—C5	1.330 (2)	N1—C2	1.4953 (19)
C2—C3	1.543 (2)	N3—C6	1.378 (2)
N1—H1A	1.042 (4)	C4—C6	1.376 (3)
C2—H2	1.110 (4)	N1—H1C	1.039 (4)
C6—H6	1.085 (4)	C3—H3B	1.096 (4)
O2—C1	1.256 (2)	N2—C4	1.3917 (18)
N3—C5	1.353 (2)	C1—C2	1.542 (2)
C3—C4	1.502 (3)	N3—H3	1.054 (4)
N1—H1B	1.042 (4)	C5—H5	1.082 (4)
C4—N2—C5	105.11 (13)	C3—C2—H2	109.7 (2)
O1—C1—C2	116.75 (15)	C4—C3—H3A	110.0 (2)
N1—C2—C3	110.15 (12)	N2—C5—H5	124.7 (2)
N2—C4—C3	120.67 (15)	C4—C6—H6	131.5 (3)
N2—C5—N3	112.06 (13)	O1—C1—O2	126.80 (19)
C2—N1—H1A	109.2 (2)	N1—C2—C1	109.88 (14)
C5—N3—H3	126.3 (2)	C2—C3—C4	112.27 (13)
C1—C2—H2	109.3 (2)	C3—C4—C6	129.87 (14)
C2—C3—H3B	108.0 (3)	C2—N1—H1C	108.6 (2)
N3—C6—H6	122.3 (3)	N1—C2—H2	107.5 (2)
C5—N3—C6	107.12 (15)	C2—C3—H3A	109.3 (2)
O2—C1—C2	116.41 (16)	C4—C3—H3B	109.2 (3)
C1—C2—C3	110.31 (12)	N3—C5—H5	123.3 (3)
N2—C4—C6	109.46 (15)	H1A—N1—H1B	106.4 (3)
N3—C6—C4	106.24 (13)	H3A—C3—H3B	108.0 (3)
C2—N1—H1B	111.2 (2)	H1A—N1—H1C	110.7 (3)
C6—N3—H3	126.6 (2)	H1B—N1—H1C	110.9 (3)
C5—N2—C4—C3	−179.65 (13)	O1—C1—C2—N1	−26.6 (2)
C6—N3—C5—N2	0.80 (16)	O2—C1—C2—C3	−83.06 (19)
O1—C1—C2—C3	94.99 (19)	C2—C3—C4—N2	55.75 (18)
N1—C2—C3—C4	−58.05 (18)	C3—C4—C6—N3	−179.92 (15)
C2—C3—C4—C6	−123.87 (17)	H1A—N1—C2—H2	−78.5 (3)
H1A—N1—C2—C1	162.7 (3)	H1B—N1—C2—H2	164.4 (3)
H1B—N1—C2—C1	45.6 (3)	H1C—N1—C2—H2	42.3 (3)
H1C—N1—C2—C1	−76.6 (3)	H3—N3—C5—N2	178.1 (3)
C4—N2—C5—H5	179.5 (3)	H3—N3—C6—C4	−178.0 (3)
H3—N3—C5—H5	−1.9 (4)	O2—C1—C2—H2	37.6 (3)
H3—N3—C6—H6	3.4 (4)	N1—C2—C3—H3A	64.2 (3)
C5—N2—C4—C6	0.05 (16)	C1—C2—C3—H3B	60.0 (3)
C5—N3—C6—C4	−0.72 (16)	H2—C2—C3—H3B	−60.5 (4)
O2—C1—C2—N1	155.31 (16)	H3B—C3—C4—N2	175.6 (3)
C1—C2—C3—C4	−179.52 (13)	C3—C4—C6—H6	−1.5 (4)
N2—C4—C6—N3	0.42 (16)	N1—C2—C3—H3B	−178.5 (3)
H1A—N1—C2—C3	40.9 (3)	H2—C2—C3—C4	60.0 (3)
H1B—N1—C2—C3	−76.1 (3)	H3A—C3—C4—N2	−66.1 (3)
H1C—N1—C2—C3	161.7 (3)	H3B—C3—C4—C6	−4.1 (3)
C6—N3—C5—H5	−179.2 (3)	C1—C2—C3—H3A	−57.2 (3)
C5—N3—C6—H6	−179.3 (3)	H2—C2—C3—H3A	−177.7 (3)
O1—C1—C2—H2	−144.3 (3)	H3A—C3—C4—C6	114.3 (3)
C4—N2—C5—N3	−0.53 (16)	N2—C4—C6—H6	178.8 (3)

2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HOTN01)

Crystal data

C6H9N3O2	Dx = 1.470 Mg m^−3
Mr = 155.16	Neutron radiation, λ = 0.80 Å
Orthorhombic, P212121	Cell parameters from 6123 reflections
a = 5.1521 (10) Å	θ = 3.0–36.0°
b = 7.2228 (2) Å	µ = 0.0 mm^−1
c = 18.8440 (6) Å	T = 105 K
V = 701.23 (14) Å^3	Needle, colourless
Z = 4	0.35 × 0.30 × 0.15 mm
F(000) = 184

Data collection

KOALA diffractometer	Rint = 0.214
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia	θmax = 71.2°
Laue scans	h = −8→8
32598 measured reflections	k = −12→11
1361 independent reflections	l = −28→28
1061 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.074	(Δ/σ)max < 0.001
S = 1.15	Δρmax = 1.27 e Å^−3
1361 reflections	Δρmin = −1.10 e Å^−3
181 parameters	Absolute structure: Absolute structure known from synthesis
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
O2	0.3242 (4)	0.4979 (3)	0.24007 (13)	0.0147 (5)
O1	0.7306 (4)	0.4942 (3)	0.19789 (14)	0.0151 (5)
N1	0.9167 (2)	0.31345 (17)	0.31167 (9)	0.0114 (3)
H1B	1.0391 (8)	0.3799 (6)	0.2768 (3)	0.0239 (9)
H1C	0.8786 (8)	0.1799 (5)	0.2943 (3)	0.0253 (10)
H1A	1.0097 (7)	0.3110 (6)	0.3610 (3)	0.0239 (9)
N3	0.8707 (2)	0.50253 (18)	0.55332 (9)	0.0127 (3)
H3	0.8483 (7)	0.5046 (6)	0.6092 (2)	0.0248 (9)
N2	1.0323 (2)	0.43948 (18)	0.44686 (9)	0.0130 (3)
C4	0.8041 (3)	0.5392 (2)	0.43910 (11)	0.0110 (4)
C1	0.5648 (3)	0.4728 (2)	0.24541 (10)	0.0108 (4)
C2	0.6660 (3)	0.4161 (2)	0.31938 (11)	0.0088 (4)
H2	0.5255 (7)	0.3212 (6)	0.3440 (2)	0.0222 (9)
C6	0.7018 (4)	0.5786 (3)	0.50489 (11)	0.0120 (4)
H6	0.5312 (8)	0.6534 (7)	0.5202 (3)	0.0322 (11)
C5	1.0634 (3)	0.4201 (3)	0.51659 (12)	0.0136 (4)
H5	1.2222 (8)	0.3459 (7)	0.5419 (3)	0.0317 (11)
C3	0.7043 (4)	0.5885 (2)	0.36664 (12)	0.0129 (4)
H3A	0.8376 (10)	0.6834 (6)	0.3400 (3)	0.0310 (11)
H3B	0.5166 (8)	0.6576 (7)	0.3708 (3)	0.0328 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0112 (9)	0.0174 (10)	0.0156 (14)	0.0003 (8)	−0.0018 (7)	0.0040 (10)
O1	0.0096 (8)	0.0235 (10)	0.0122 (14)	−0.0012 (8)	0.0006 (7)	0.0021 (9)
N1	0.0103 (5)	0.0124 (6)	0.0115 (9)	0.0022 (4)	−0.0003 (5)	−0.0003 (5)
H1B	0.0246 (19)	0.0253 (19)	0.022 (3)	0.0030 (15)	0.0085 (17)	0.0031 (16)
H1C	0.0304 (19)	0.0159 (17)	0.029 (3)	0.0028 (14)	−0.0022 (17)	−0.0046 (17)
H1A	0.0211 (18)	0.031 (2)	0.019 (3)	0.0051 (14)	−0.0030 (16)	0.0010 (19)
N3	0.0149 (5)	0.0152 (6)	0.0079 (9)	0.0004 (5)	0.0006 (4)	−0.0009 (6)
H3	0.0282 (18)	0.034 (2)	0.012 (3)	−0.0018 (18)	−0.0025 (15)	0.0039 (19)
N2	0.0135 (5)	0.0151 (6)	0.0105 (8)	0.0033 (4)	0.0000 (5)	−0.0012 (6)
C4	0.0117 (6)	0.0100 (7)	0.0114 (12)	0.0012 (6)	0.0002 (7)	0.0002 (7)
C1	0.0088 (7)	0.0111 (7)	0.0126 (12)	−0.0007 (7)	−0.0019 (6)	0.0000 (7)
C2	0.0087 (7)	0.0081 (7)	0.0096 (11)	0.0009 (6)	0.0003 (6)	0.0013 (7)
H2	0.0216 (17)	0.0230 (18)	0.022 (3)	−0.0048 (15)	0.0016 (16)	0.0035 (17)
C6	0.0111 (7)	0.0150 (8)	0.0098 (12)	0.0017 (7)	0.0004 (6)	−0.0028 (7)
H6	0.0252 (19)	0.042 (3)	0.030 (3)	0.0156 (18)	0.0021 (19)	−0.008 (2)
C5	0.0133 (7)	0.0162 (8)	0.0112 (12)	0.0041 (7)	−0.0033 (7)	0.0002 (8)
H5	0.0270 (19)	0.039 (2)	0.029 (3)	0.0138 (17)	−0.0068 (19)	0.006 (2)
C3	0.0155 (8)	0.0099 (8)	0.0133 (12)	0.0019 (7)	−0.0034 (7)	−0.0007 (8)
H3A	0.041 (2)	0.0249 (19)	0.027 (3)	−0.0104 (19)	−0.003 (2)	0.0066 (19)
H3B	0.027 (2)	0.038 (2)	0.033 (3)	0.0193 (17)	−0.009 (2)	−0.008 (2)

Geometric parameters (Å, º)

O1—C1	1.247 (3)	C3—H3A	1.093 (5)
N2—C5	1.331 (3)	N1—C2	1.4964 (19)
C2—C3	1.544 (2)	N3—C6	1.376 (3)
N1—H1A	1.046 (6)	C4—C6	1.377 (3)
C2—H2	1.100 (4)	N1—H1C	1.037 (4)
C6—H6	1.071 (5)	C3—H3B	1.091 (5)
O2—C1	1.257 (3)	N2—C4	1.3865 (19)
N3—C5	1.349 (2)	C1—C2	1.544 (3)
C3—C4	1.502 (3)	N3—H3	1.059 (4)
N1—H1B	1.030 (5)	C5—H5	1.088 (5)
C4—N2—C5	105.12 (15)	C3—C2—H2	110.1 (3)
O1—C1—C2	116.74 (17)	C4—C3—H3A	110.6 (3)
N1—C2—C3	110.21 (14)	N2—C5—H5	125.1 (3)
N2—C4—C3	120.62 (17)	C4—C6—H6	131.4 (4)
N2—C5—N3	111.81 (15)	O1—C1—O2	126.9 (2)
C2—N1—H1A	108.5 (3)	N1—C2—C1	109.59 (15)
C5—N3—H3	126.6 (3)	C2—C3—C4	112.15 (13)
C1—C2—H2	108.9 (2)	C3—C4—C6	129.69 (16)
C2—C3—H3B	107.3 (3)	C2—N1—H1C	109.2 (2)
N3—C6—H6	122.8 (4)	N1—C2—H2	107.5 (2)
C5—N3—C6	107.55 (17)	C2—C3—H3A	108.8 (3)
O2—C1—C2	116.34 (18)	C4—C3—H3B	110.3 (3)
C1—C2—C3	110.50 (13)	N3—C5—H5	123.1 (3)
N2—C4—C6	109.69 (17)	H1A—N1—H1B	107.1 (4)
N3—C6—C4	105.82 (17)	H3A—C3—H3B	107.7 (4)
C2—N1—H1B	111.1 (3)	H1A—N1—H1C	110.6 (4)
C6—N3—H3	125.8 (2)	H1B—N1—H1C	110.4 (4)
C5—N2—C4—C3	−179.96 (15)	O1—C1—C2—N1	−26.9 (2)
C6—N3—C5—N2	0.7 (2)	O2—C1—C2—C3	−83.2 (2)
O1—C1—C2—C3	94.7 (2)	C2—C3—C4—N2	56.3 (2)
N1—C2—C3—C4	−58.4 (2)	C3—C4—C6—N3	−179.61 (15)
C2—C3—C4—C6	−123.8 (2)	H1A—N1—C2—H2	−78.6 (4)
H1A—N1—C2—C1	163.2 (3)	H1B—N1—C2—H2	163.9 (4)
H1B—N1—C2—C1	45.7 (3)	H1C—N1—C2—H2	42.0 (4)
H1C—N1—C2—C1	−76.2 (4)	H3—N3—C5—N2	178.6 (3)
C4—N2—C5—H5	178.8 (4)	H3—N3—C6—C4	−178.5 (3)
H3—N3—C5—H5	−0.7 (5)	O2—C1—C2—H2	37.9 (3)
H3—N3—C6—H6	2.5 (5)	N1—C2—C3—H3A	64.2 (3)
C5—N2—C4—C6	0.15 (19)	C1—C2—C3—H3B	59.1 (4)
C5—N3—C6—C4	−0.6 (2)	H2—C2—C3—H3B	−61.3 (4)
O2—C1—C2—N1	155.17 (16)	H3B—C3—C4—N2	175.8 (3)
C1—C2—C3—C4	−179.71 (14)	C3—C4—C6—H6	−0.7 (5)
N2—C4—C6—N3	0.3 (2)	N1—C2—C3—H3B	−179.7 (3)
H1A—N1—C2—C3	41.4 (3)	H2—C2—C3—C4	60.0 (3)
H1B—N1—C2—C3	−76.1 (4)	H3A—C3—C4—N2	−65.2 (3)
H1C—N1—C2—C3	162.0 (4)	H3B—C3—C4—C6	−4.3 (4)
C6—N3—C5—H5	−178.6 (4)	C1—C2—C3—H3A	−57.1 (3)
C5—N3—C6—H6	−179.6 (4)	H2—C2—C3—H3A	−177.5 (4)
O1—C1—C2—H2	−144.2 (3)	H3A—C3—C4—C6	114.6 (3)
C4—N2—C5—N3	−0.53 (19)	N2—C4—C6—H6	179.2 (4)

2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HOTN02)

Crystal data

C6H9N3O2	Dx = 1.442 Mg m^−3
Mr = 155.16	Neutron radiation, λ = 0.80 Å
Orthorhombic, P212121	Cell parameters from 4787 reflections
a = 5.1690 (3) Å	θ = 3.0–32.3°
b = 7.3430 (5) Å	µ = 0.0 mm^−1
c = 18.8317 (13) Å	T = 295 K
V = 714.78 (8) Å^3	Needle, colourless
Z = 4	0.35 × 0.30 × 0.15 mm
F(000) = 184

Data collection

KOALA diffractometer	Rint = 0.237
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia	θmax = 70.9°
Laue scans	h = −7→7
32190 measured reflections	k = −11→11
1104 independent reflections	l = −26→26
781 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.078	(Δ/σ)max < 0.001
S = 1.19	Δρmax = 0.67 e Å^−3
1104 reflections	Δρmin = −0.65 e Å^−3
181 parameters	Absolute structure: Absolute structure known from synthesis
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
O2	0.3241 (6)	0.5093 (4)	0.24197 (18)	0.0374 (8)
O1	0.7255 (6)	0.5056 (5)	0.1988 (2)	0.0399 (8)
N1	0.9129 (4)	0.3213 (2)	0.31058 (13)	0.0274 (4)
H1B	1.0310 (11)	0.3850 (8)	0.2762 (4)	0.0461 (14)
H1C	0.8690 (11)	0.1909 (8)	0.2926 (3)	0.0450 (14)
H1A	1.0058 (9)	0.3154 (8)	0.3593 (3)	0.0406 (13)
N3	0.8748 (3)	0.4997 (3)	0.55358 (12)	0.0322 (4)
H3	0.8527 (11)	0.4994 (8)	0.6087 (4)	0.0483 (14)
N2	1.0323 (3)	0.4398 (2)	0.44699 (11)	0.0334 (5)
C4	0.8077 (5)	0.5400 (3)	0.43942 (14)	0.0265 (5)
C1	0.5626 (5)	0.4821 (3)	0.24611 (13)	0.0258 (6)
C2	0.6649 (4)	0.4240 (3)	0.31964 (13)	0.0229 (5)
H2	0.5241 (9)	0.3313 (8)	0.3445 (3)	0.0407 (13)
C6	0.7065 (5)	0.5766 (4)	0.50536 (15)	0.0329 (7)
H6	0.5344 (12)	0.6503 (10)	0.5214 (4)	0.0586 (17)
C5	1.0649 (5)	0.4188 (4)	0.51627 (16)	0.0341 (6)
H5	1.2206 (13)	0.3431 (10)	0.5413 (4)	0.0606 (18)
C3	0.7079 (6)	0.5905 (3)	0.36726 (15)	0.0311 (6)
H3A	0.8392 (15)	0.6853 (9)	0.3410 (4)	0.0595 (19)
H3B	0.5253 (13)	0.6609 (9)	0.3727 (4)	0.0627 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0230 (14)	0.0439 (19)	0.045 (2)	0.0002 (13)	−0.0064 (12)	0.0150 (16)
O1	0.0304 (14)	0.063 (2)	0.027 (2)	−0.0015 (14)	−0.0001 (11)	0.0094 (16)
N1	0.0278 (9)	0.0278 (9)	0.0266 (14)	0.0061 (7)	−0.0012 (9)	−0.0019 (9)
H1B	0.044 (3)	0.051 (3)	0.044 (4)	0.011 (3)	0.005 (3)	0.001 (3)
H1C	0.052 (3)	0.037 (3)	0.046 (4)	0.004 (2)	−0.006 (3)	−0.006 (3)
H1A	0.033 (3)	0.055 (3)	0.034 (4)	0.013 (2)	0.001 (2)	0.001 (3)
N3	0.0383 (10)	0.0378 (10)	0.0205 (13)	−0.0013 (8)	−0.0002 (7)	−0.0017 (9)
H3	0.060 (4)	0.055 (3)	0.030 (4)	−0.003 (3)	−0.005 (3)	0.001 (3)
N2	0.0315 (9)	0.0418 (11)	0.0270 (13)	0.0077 (7)	−0.0007 (8)	0.0010 (9)
C4	0.0328 (11)	0.0250 (12)	0.0217 (16)	0.0009 (9)	−0.0026 (10)	−0.0027 (11)
C1	0.0235 (11)	0.0296 (12)	0.0242 (17)	0.0007 (10)	−0.0013 (9)	0.0027 (11)
C2	0.0244 (11)	0.0242 (11)	0.0202 (15)	0.0011 (9)	0.0020 (9)	0.0028 (9)
H2	0.031 (2)	0.053 (3)	0.039 (4)	−0.011 (2)	0.005 (2)	0.007 (3)
C6	0.0330 (13)	0.0395 (15)	0.0262 (18)	0.0055 (12)	0.0022 (11)	−0.0054 (12)
H6	0.050 (3)	0.075 (4)	0.051 (4)	0.026 (3)	0.007 (3)	−0.007 (3)
C5	0.0343 (13)	0.0453 (16)	0.0226 (17)	0.0068 (13)	−0.0041 (12)	0.0002 (13)
H5	0.058 (4)	0.077 (4)	0.047 (5)	0.022 (3)	−0.019 (3)	0.006 (3)
C3	0.0452 (15)	0.0224 (12)	0.0257 (18)	0.0073 (11)	−0.0072 (12)	−0.0015 (11)
H3A	0.093 (5)	0.047 (3)	0.038 (4)	−0.022 (4)	−0.010 (4)	0.010 (3)
H3B	0.069 (5)	0.065 (4)	0.054 (5)	0.028 (3)	−0.008 (4)	−0.017 (3)

Geometric parameters (Å, º)

O1—C1	1.238 (4)	C3—H3A	1.091 (8)
N2—C5	1.325 (4)	N1—C2	1.497 (3)
C2—C3	1.532 (3)	N3—C6	1.379 (3)
N1—H1A	1.037 (6)	C4—C6	1.374 (4)
C2—H2	1.101 (6)	N1—H1C	1.041 (6)
C6—H6	1.084 (7)	C3—H3B	1.081 (7)
O2—C1	1.251 (4)	N2—C4	1.382 (3)
N3—C5	1.346 (3)	C1—C2	1.542 (3)
C3—C4	1.500 (4)	N3—H3	1.044 (8)
N1—H1B	1.005 (7)	C5—H5	1.086 (8)
C4—N2—C5	105.7 (2)	C3—C2—H2	109.9 (4)
O1—C1—C2	116.8 (3)	C4—C3—H3A	110.8 (5)
N1—C2—C3	110.15 (19)	N2—C5—H5	125.6 (5)
N2—C4—C3	120.9 (2)	C4—C6—H6	131.4 (5)
N2—C5—N3	111.7 (2)	O1—C1—O2	127.1 (3)
C2—N1—H1A	108.5 (3)	N1—C2—C1	109.3 (2)
C5—N3—H3	126.7 (4)	C2—C3—C4	112.51 (19)
C1—C2—H2	109.0 (3)	C3—C4—C6	129.8 (2)
C2—C3—H3B	108.1 (4)	C2—N1—H1C	108.3 (4)
N3—C6—H6	122.6 (5)	N1—C2—H2	107.6 (3)
C5—N3—C6	107.3 (2)	C2—C3—H3A	109.5 (4)
O2—C1—C2	116.0 (2)	C4—C3—H3B	109.4 (5)
C1—C2—C3	110.76 (19)	N3—C5—H5	122.7 (5)
N2—C4—C6	109.3 (2)	H1A—N1—H1B	108.0 (5)
N3—C6—C4	106.0 (2)	H3A—C3—H3B	106.3 (6)
C2—N1—H1B	111.0 (4)	H1A—N1—H1C	110.5 (5)
C6—N3—H3	125.9 (4)	H1B—N1—H1C	110.6 (5)
C5—N2—C4—C3	−179.9 (2)	O1—C1—C2—N1	−28.0 (3)
C6—N3—C5—N2	0.6 (3)	O2—C1—C2—C3	−83.0 (3)
O1—C1—C2—C3	93.5 (3)	C2—C3—C4—N2	56.3 (3)
N1—C2—C3—C4	−58.9 (3)	C3—C4—C6—N3	−179.9 (2)
C2—C3—C4—C6	−122.8 (3)	H1A—N1—C2—H2	−77.7 (5)
H1A—N1—C2—C1	164.0 (4)	H1B—N1—C2—H2	163.8 (6)
H1B—N1—C2—C1	45.5 (5)	H1C—N1—C2—H2	42.3 (5)
H1C—N1—C2—C1	−76.0 (4)	H3—N3—C5—N2	177.9 (4)
C4—N2—C5—H5	178.2 (5)	H3—N3—C6—C4	−178.2 (5)
H3—N3—C5—H5	−0.5 (7)	O2—C1—C2—H2	38.1 (4)
H3—N3—C6—H6	2.4 (7)	N1—C2—C3—H3A	64.7 (5)
C5—N2—C4—C6	−0.5 (3)	C1—C2—C3—H3B	59.1 (5)
C5—N3—C6—C4	−0.9 (3)	H2—C2—C3—H3B	−61.4 (6)
O2—C1—C2—N1	155.5 (2)	H3B—C3—C4—N2	176.5 (4)
C1—C2—C3—C4	−180.0 (2)	C3—C4—C6—H6	−0.6 (7)
N2—C4—C6—N3	0.9 (3)	N1—C2—C3—H3B	−179.9 (5)
H1A—N1—C2—C3	42.1 (4)	H2—C2—C3—C4	59.5 (4)
H1B—N1—C2—C3	−76.4 (5)	H3A—C3—C4—N2	−66.6 (5)
H1C—N1—C2—C3	162.1 (4)	H3B—C3—C4—C6	−2.7 (5)
C6—N3—C5—H5	−177.7 (5)	C1—C2—C3—H3A	−56.3 (5)
C5—N3—C6—H6	179.7 (5)	H2—C2—C3—H3A	−176.9 (5)
O1—C1—C2—H2	−145.4 (4)	H3A—C3—C4—C6	114.2 (5)
C4—N2—C5—N3	−0.1 (3)	N2—C4—C6—H6	−179.8 (6)

(HMTX18)

Crystal data

C6H9N3O2	F(000) = 164.036
Mr = 155.16	Dx = 1.464 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.1651 (2) Å	Cell parameters from 4301 reflections
b = 7.2324 (2) Å	θ = 3.6–30.5°
c = 9.4957 (3) Å	µ = 0.11 mm^−1
β = 97.065 (2)°	T = 5 K
V = 352.03 (2) Å^3	Plate, colourless
Z = 2	0.2 × 0.2 × 0.1 mm

Data collection

Bruker APEX-II CCD diffractometer	2138 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics	2087 reflections with I ≥ 2u(I)
Multilayer optics monochromator	Rint = 0.025
φ scans	θmax = 30.5°, θmin = 3.6°
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10	h = −7→7
Tmin = 0.687, Tmax = 0.746	k = −10→10
11118 measured reflections	l = −13→13

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.017	w = 1/[σ^2(Fo^2) + (0.0081P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.029	(Δ/σ)max = 0.001
S = 1.28	Δρmax = 0.12 e Å^−3
2138 reflections	Δρmin = −0.10 e Å^−3
181 parameters	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
100 restraints	Absolute structure parameter: 0.4 (9)

Special details

Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-02-14_18-53-41

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

	x	y	z	Uiso*/Ueq
O2	0.31533 (7)	0.45284 (5)	1.01583 (3)	0.00805 (8)
O1	0.74155 (7)	0.44673 (6)	1.09914 (3)	0.00847 (8)
N1	0.87626 (10)	0.63462 (6)	0.87300 (4)	0.00670 (9)
H1A	0.9395 (16)	0.6386 (12)	0.7759 (8)	0.0180 (19)
H1B	1.0107 (16)	0.5691 (12)	0.9411 (8)	0.016 (2)
H1C	0.8493 (17)	0.7655 (12)	0.9094 (9)	0.019 (2)
N3	0.72055 (9)	0.44327 (7)	0.38766 (4)	0.00739 (9)
H3	0.6885 (14)	0.4347 (13)	0.2818 (7)	0.0134 (19)
N2	0.92189 (9)	0.51432 (6)	0.60095 (4)	0.00714 (10)
C1	0.55412 (11)	0.47508 (7)	1.00470 (5)	0.00581 (10)
C4	0.69853 (11)	0.41306 (7)	0.61655 (5)	0.00627 (11)
C6	0.57237 (11)	0.36816 (8)	0.48466 (5)	0.00733 (11)
H6	0.3961 (15)	0.2918 (12)	0.4530 (7)	0.022 (2)
C2	0.62067 (10)	0.53564 (7)	0.85771 (5)	0.00583 (10)
H2	0.4708 (13)	0.6313 (10)	0.8108 (6)	0.0117 (17)
C5	0.92631 (11)	0.52932 (8)	0.46208 (5)	0.00783 (11)
H5	1.0721 (15)	0.6038 (11)	0.4133 (7)	0.026 (2)
C3	0.62991 (12)	0.36483 (7)	0.76129 (5)	0.00731 (11)
H3A	0.7703 (15)	0.2692 (11)	0.8163 (8)	0.0230 (19)
H3B	0.4355 (15)	0.3026 (11)	0.7513 (7)	0.0201 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.00614 (19)	0.00906 (18)	0.00920 (14)	−0.00018 (17)	0.00196 (13)	0.00264 (14)
O1	0.0071 (2)	0.01195 (18)	0.00635 (14)	−0.00011 (18)	0.00069 (12)	0.00161 (14)
N1	0.0071 (2)	0.0060 (2)	0.00698 (18)	−0.00118 (19)	0.00082 (17)	−0.00020 (16)
H1A	0.022 (5)	0.021 (5)	0.012 (2)	0.006 (3)	0.0058 (14)	0.0043 (16)
H1B	0.015 (4)	0.016 (4)	0.015 (3)	0.001 (2)	−0.0047 (18)	0.0038 (18)
H1C	0.022 (5)	0.012 (3)	0.023 (4)	0.0021 (17)	0.005 (3)	−0.0029 (15)
N3	0.0087 (2)	0.0079 (2)	0.00553 (16)	−0.00014 (19)	0.00092 (14)	−0.00005 (16)
H3	0.016 (4)	0.015 (5)	0.009 (2)	−0.002 (3)	0.0011 (12)	−0.0015 (13)
N2	0.0070 (2)	0.0078 (2)	0.00656 (17)	−0.00197 (18)	0.00065 (15)	−0.00049 (15)
C1	0.0063 (3)	0.0053 (3)	0.00605 (18)	0.0003 (2)	0.00129 (17)	0.00000 (17)
C4	0.0073 (3)	0.0064 (3)	0.00533 (19)	−0.0005 (2)	0.00162 (17)	0.00000 (16)
C6	0.0079 (3)	0.0076 (3)	0.0063 (2)	−0.0012 (2)	0.00037 (18)	−0.00089 (18)
H6	0.017 (3)	0.027 (5)	0.021 (4)	−0.0114 (19)	−0.0002 (19)	−0.001 (3)
C2	0.0060 (3)	0.0064 (2)	0.00523 (19)	0.0002 (2)	0.00109 (17)	0.00051 (18)
H2	0.010 (4)	0.002 (3)	0.022 (4)	−0.0009 (17)	−0.002 (2)	0.004 (2)
C5	0.0082 (3)	0.0081 (2)	0.0075 (2)	−0.0008 (2)	0.00207 (18)	0.00025 (18)
H5	0.028 (4)	0.034 (6)	0.018 (4)	−0.016 (2)	0.0074 (18)	0.004 (2)
C3	0.0096 (3)	0.0061 (2)	0.0064 (2)	−0.0014 (2)	0.00139 (18)	−0.00036 (17)
H3A	0.028 (4)	0.014 (4)	0.025 (4)	0.0066 (18)	−0.005 (2)	0.001 (2)
H3B	0.016 (3)	0.020 (4)	0.024 (4)	−0.0069 (15)	0.0021 (17)	−0.002 (3)

Geometric parameters (Å, º)

O2—C1	1.2611 (6)	N2—C5	1.3261 (6)
O1—C1	1.2530 (6)	C1—C2	1.5415 (7)
N1—H1A	1.016 (7)	C4—C6	1.3776 (6)
N1—H1B	1.007 (8)	C4—C3	1.5020 (7)
N1—H1C	1.023 (9)	C6—H6	1.076 (7)
N1—C2	1.4930 (7)	C2—H2	1.091 (7)
N3—H3	1.000 (6)	C2—C3	1.5419 (7)
N3—C6	1.3794 (7)	C5—H5	1.076 (7)
N3—C5	1.3533 (7)	C3—H3A	1.088 (7)
N2—C4	1.3897 (7)	C3—H3B	1.094 (8)
H1B—N1—H1A	108.8 (6)	H6—C6—N3	122.4 (4)
H1C—N1—H1A	110.6 (7)	H6—C6—C4	131.6 (4)
H1C—N1—H1B	109.3 (6)	C1—C2—N1	109.95 (4)
C2—N1—H1A	107.7 (5)	H2—C2—N1	108.1 (4)
C2—N1—H1B	111.6 (5)	H2—C2—C1	108.9 (4)
C2—N1—H1C	108.7 (5)	C3—C2—N1	110.51 (4)
C6—N3—H3	127.6 (4)	C3—C2—C1	109.67 (4)
C5—N3—H3	125.1 (4)	C3—C2—H2	109.7 (3)
C5—N3—C6	107.28 (4)	N2—C5—N3	111.91 (5)
C5—N2—C4	105.37 (4)	H5—C5—N3	123.5 (4)
O1—C1—O2	126.63 (5)	H5—C5—N2	124.6 (4)
C2—C1—O2	116.20 (4)	C2—C3—C4	112.66 (4)
C2—C1—O1	117.12 (5)	H3A—C3—C4	111.6 (4)
C6—C4—N2	109.48 (4)	H3A—C3—C2	107.0 (4)
C3—C4—N2	120.82 (4)	H3B—C3—C4	109.5 (4)
C3—C4—C6	129.69 (5)	H3B—C3—C2	106.6 (4)
C4—C6—N3	105.96 (5)	H3B—C3—H3A	109.3 (6)
C5—N2—C4—C3	178.91 (5)	O1—C1—C2—N1	−27.41 (6)
C6—N3—C5—N2	0.25 (7)	O2—C1—C2—C3	−83.27 (6)
O1—C1—C2—C3	94.30 (6)	C2—C3—C4—N2	53.66 (7)
N1—C2—C3—C4	−57.64 (6)	C3—C4—C6—N3	−178.61 (5)
C2—C3—C4—C6	−127.97 (6)	H1A—N1—C2—H2	−77.8 (6)
H1A—N1—C2—C1	163.5 (5)	H1B—N1—C2—H2	162.8 (6)
H1B—N1—C2—C1	44.1 (5)	H1C—N1—C2—H2	42.2 (6)
H1C—N1—C2—C1	−76.5 (5)	H3—N3—C5—N2	−178.3 (6)
C4—N2—C5—H5	178.1 (5)	H3—N3—C6—C4	178.4 (6)
H3—N3—C5—H5	3.3 (8)	O2—C1—C2—H2	36.8 (4)
H3—N3—C6—H6	−1.6 (8)	N1—C2—C3—H3A	65.4 (4)
C5—N2—C4—C6	0.24 (6)	C1—C2—C3—H3B	60.9 (4)
C5—N3—C6—C4	−0.09 (7)	H2—C2—C3—H3B	−58.7 (5)
O2—C1—C2—N1	155.03 (4)	H3B—C3—C4—N2	172.1 (4)
C1—C2—C3—C4	−179.00 (5)	C3—C4—C6—H6	1.4 (6)
N2—C4—C6—N3	−0.09 (6)	N1—C2—C3—H3B	−177.8 (4)
H1A—N1—C2—C3	42.3 (5)	H2—C2—C3—C4	61.4 (4)
H1B—N1—C2—C3	−77.1 (5)	H3A—C3—C4—N2	−66.7 (4)
H1C—N1—C2—C3	162.3 (5)	H3B—C3—C4—C6	−9.5 (4)
C6—N3—C5—H5	−178.2 (5)	C1—C2—C3—H3A	−56.0 (4)
C5—N3—C6—H6	179.9 (5)	H2—C2—C3—H3A	−175.6 (6)
O1—C1—C2—H2	−145.6 (4)	H3A—C3—C4—C6	111.7 (5)
C4—N2—C5—N3	−0.31 (6)	N2—C4—C6—H6	179.9 (6)

(HMTX19)

Crystal data

C6H9N3O2	F(000) = 164.036
Mr = 155.16	Dx = 1.455 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.1656 (2) Å	Cell parameters from 2706 reflections
b = 7.2761 (3) Å	θ = 3.5–30.4°
c = 9.4978 (3) Å	µ = 0.11 mm^−1
β = 97.316 (3)°	T = 105 K
V = 354.07 (2) Å^3	Plate, colourless
Z = 2	0.2 × 0.2 × 0.1 mm

Data collection

Bruker APEX-II CCD diffractometer	2148 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics	2032 reflections with I ≥ 2u(I)
Multilayer optics monochromator	Rint = 0.033
φ scans	θmax = 30.5°, θmin = 3.5°
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10	h = −7→7
Tmin = 0.650, Tmax = 0.746	k = −10→10
11193 measured reflections	l = −13→13

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0076P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.032	(Δ/σ)max = 0.0001
S = 1.18	Δρmax = 0.15 e Å^−3
2148 reflections	Δρmin = −0.12 e Å^−3
181 parameters	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
100 restraints	Absolute structure parameter: 0.3 (11)

Special details

Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-02-14_21-31-35

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

	x	y	z	Uiso*/Ueq
O2	0.31462 (8)	0.45104 (7)	1.01449 (4)	0.01453 (10)
O1	0.73996 (8)	0.44614 (8)	1.09888 (4)	0.01520 (11)
N1	0.87419 (11)	0.63417 (8)	0.87357 (6)	0.01094 (12)
H1A	0.9415 (19)	0.6410 (15)	0.7770 (10)	0.027 (3)
H1B	1.0108 (19)	0.5709 (14)	0.9431 (9)	0.023 (2)
H1C	0.8448 (18)	0.7607 (15)	0.9100 (10)	0.022 (2)
N3	0.72092 (10)	0.44401 (10)	0.38769 (5)	0.01304 (12)
H3	0.6849 (15)	0.4344 (15)	0.2827 (8)	0.021 (2)
N2	0.92139 (11)	0.51550 (8)	0.60132 (5)	0.01285 (13)
C1	0.55305 (12)	0.47409 (9)	1.00405 (6)	0.00975 (14)
C4	0.69926 (12)	0.41379 (9)	0.61629 (6)	0.01066 (15)
C6	0.57349 (13)	0.36888 (10)	0.48424 (6)	0.01262 (14)
H6	0.3984 (17)	0.2938 (14)	0.4523 (8)	0.032 (3)
C2	0.61967 (12)	0.53500 (10)	0.85723 (6)	0.00947 (13)
H2	0.4685 (14)	0.6303 (12)	0.8112 (7)	0.019 (2)
C5	0.92565 (13)	0.53046 (10)	0.46240 (6)	0.01370 (14)
H5	1.0726 (17)	0.6058 (13)	0.4133 (8)	0.035 (3)
C3	0.63061 (14)	0.36558 (10)	0.76089 (6)	0.01275 (14)
H3A	0.7714 (17)	0.2688 (12)	0.8157 (9)	0.027 (2)
H3B	0.4403 (17)	0.3002 (13)	0.7510 (9)	0.030 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0113 (2)	0.0168 (3)	0.01614 (19)	0.0001 (2)	0.00433 (16)	0.0054 (2)
O1	0.0128 (2)	0.0240 (3)	0.00897 (17)	−0.0002 (2)	0.00203 (16)	0.0036 (2)
N1	0.0123 (3)	0.0110 (4)	0.0096 (2)	−0.0018 (3)	0.0015 (2)	−0.0007 (2)
H1A	0.037 (6)	0.025 (6)	0.021 (3)	0.010 (4)	0.0118 (19)	0.007 (2)
H1B	0.017 (5)	0.021 (6)	0.028 (4)	−0.002 (3)	−0.007 (2)	0.008 (2)
H1C	0.025 (6)	0.014 (4)	0.026 (5)	0.000 (2)	0.005 (3)	−0.004 (2)
N3	0.0166 (3)	0.0145 (3)	0.0082 (2)	0.0005 (3)	0.00208 (18)	−0.0005 (2)
H3	0.026 (5)	0.028 (6)	0.009 (3)	−0.002 (4)	0.0024 (16)	0.0003 (17)
N2	0.0140 (3)	0.0145 (3)	0.0101 (2)	−0.0036 (2)	0.00176 (19)	−0.0010 (2)
C1	0.0108 (3)	0.0097 (4)	0.0091 (2)	0.0004 (3)	0.0030 (2)	0.0003 (2)
C4	0.0139 (3)	0.0101 (4)	0.0083 (2)	−0.0012 (3)	0.0028 (2)	−0.0002 (2)
C6	0.0144 (3)	0.0135 (4)	0.0099 (3)	−0.0014 (3)	0.0012 (2)	−0.0015 (2)
H6	0.026 (4)	0.043 (6)	0.027 (5)	−0.017 (3)	−0.002 (2)	−0.004 (3)
C2	0.0102 (3)	0.0108 (4)	0.0077 (2)	0.0000 (3)	0.0022 (2)	0.0008 (2)
H2	0.019 (4)	0.008 (4)	0.028 (5)	0.005 (2)	−0.005 (3)	0.007 (3)
C5	0.0155 (3)	0.0155 (4)	0.0108 (3)	−0.0008 (3)	0.0043 (2)	0.0010 (3)
H5	0.038 (5)	0.043 (7)	0.028 (5)	−0.016 (3)	0.014 (2)	0.005 (3)
C3	0.0186 (4)	0.0103 (4)	0.0099 (3)	−0.0034 (3)	0.0038 (2)	−0.0003 (2)
H3A	0.042 (5)	0.019 (5)	0.019 (5)	0.008 (2)	−0.002 (3)	−0.002 (3)
H3B	0.027 (4)	0.031 (5)	0.032 (5)	−0.014 (2)	0.007 (2)	−0.003 (3)

Geometric parameters (Å, º)

O2—C1	1.2594 (7)	N2—C5	1.3270 (7)
O1—C1	1.2503 (7)	C1—C2	1.5432 (8)
N1—H1A	1.022 (9)	C4—C6	1.3763 (8)
N1—H1B	1.014 (9)	C4—C3	1.5030 (8)
N1—H1C	1.002 (11)	C6—H6	1.067 (8)
N1—C2	1.4904 (8)	C2—H2	1.093 (8)
N3—H3	0.994 (7)	C2—C3	1.5405 (9)
N3—C6	1.3775 (8)	C5—H5	1.089 (8)
N3—C5	1.3515 (9)	C3—H3A	1.095 (8)
N2—C4	1.3878 (8)	C3—H3B	1.085 (9)
H1B—N1—H1A	108.5 (8)	H6—C6—N3	122.3 (5)
H1C—N1—H1A	110.4 (8)	H6—C6—C4	131.7 (5)
H1C—N1—H1B	108.4 (7)	C1—C2—N1	109.89 (5)
C2—N1—H1A	109.1 (6)	H2—C2—N1	108.1 (5)
C2—N1—H1B	112.3 (6)	H2—C2—C1	108.3 (4)
C2—N1—H1C	108.1 (5)	C3—C2—N1	110.53 (5)
C6—N3—H3	126.3 (5)	C3—C2—C1	109.64 (6)
C5—N3—H3	126.4 (5)	C3—C2—H2	110.4 (4)
C5—N3—C6	107.29 (5)	N2—C5—N3	111.89 (6)
C5—N2—C4	105.32 (5)	H5—C5—N3	123.5 (4)
O1—C1—O2	126.50 (5)	H5—C5—N2	124.6 (4)
C2—C1—O2	116.25 (5)	C2—C3—C4	112.75 (6)
C2—C1—O1	117.20 (5)	H3A—C3—C4	111.4 (5)
C6—C4—N2	109.50 (5)	H3A—C3—C2	107.7 (4)
C3—C4—N2	120.82 (5)	H3B—C3—C4	109.8 (4)
C3—C4—C6	129.67 (6)	H3B—C3—C2	107.5 (5)
C4—C6—N3	105.99 (6)	H3B—C3—H3A	107.4 (7)
C5—N2—C4—C3	179.01 (6)	O1—C1—C2—N1	−27.52 (8)
C6—N3—C5—N2	0.32 (8)	O2—C1—C2—C3	−83.32 (7)
O1—C1—C2—C3	94.16 (7)	C2—C3—C4—N2	53.53 (8)
N1—C2—C3—C4	−57.73 (7)	C3—C4—C6—N3	−178.69 (7)
C2—C3—C4—C6	−127.85 (7)	H1A—N1—C2—H2	−78.2 (7)
H1A—N1—C2—C1	163.8 (6)	H1B—N1—C2—H2	161.4 (7)
H1B—N1—C2—C1	43.5 (6)	H1C—N1—C2—H2	41.9 (7)
H1C—N1—C2—C1	−76.1 (6)	H3—N3—C5—N2	−178.7 (7)
C4—N2—C5—H5	178.3 (6)	H3—N3—C6—C4	178.8 (7)
H3—N3—C5—H5	2.7 (9)	O2—C1—C2—H2	37.2 (5)
H3—N3—C6—H6	−1.6 (10)	N1—C2—C3—H3A	65.6 (5)
C5—N2—C4—C6	0.14 (8)	C1—C2—C3—H3B	59.8 (5)
C5—N3—C6—C4	−0.22 (8)	H2—C2—C3—H3B	−59.5 (6)
O2—C1—C2—N1	155.01 (6)	H3B—C3—C4—N2	173.4 (5)
C1—C2—C3—C4	−179.02 (5)	C3—C4—C6—H6	1.8 (7)
N2—C4—C6—N3	0.06 (7)	N1—C2—C3—H3B	−179.0 (5)
H1A—N1—C2—C3	42.7 (6)	H2—C2—C3—C4	61.8 (4)
H1B—N1—C2—C3	−77.7 (6)	H3A—C3—C4—N2	−67.7 (5)
H1C—N1—C2—C3	162.8 (6)	H3B—C3—C4—C6	−8.0 (5)
C6—N3—C5—H5	−178.3 (6)	C1—C2—C3—H3A	−55.7 (5)
C5—N3—C6—H6	179.4 (6)	H2—C2—C3—H3A	−174.9 (6)
O1—C1—C2—H2	−145.4 (4)	H3A—C3—C4—C6	110.9 (5)
C4—N2—C5—N3	−0.28 (8)	N2—C4—C6—H6	−179.5 (7)

(HMTX20)

Crystal data

C6H9N3O2	F(000) = 164.037
Mr = 155.16	Dx = 1.428 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.1854 (8) Å	Cell parameters from 2412 reflections
b = 7.3998 (10) Å	θ = 3.5–30.2°
c = 9.4976 (12) Å	µ = 0.11 mm^−1
β = 98.182 (10)°	T = 295 K
V = 360.72 (9) Å^3	Plate, colourless
Z = 2	0.2 × 0.2 × 0.1 mm

Data collection

Bruker APEX-II CCD diffractometer	1806 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics	1683 reflections with I ≥ 2u(I)
Multilayer optics monochromator	Rint = 0.024
φ scans	θmax = 30.6°, θmin = 3.5°
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10	h = −6→5
Tmin = 0.689, Tmax = 0.746	k = −10→10
11356 measured reflections	l = −13→13

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0158P)^2 + 0.0067P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.049	(Δ/σ)max = 0.001
S = 1.35	Δρmax = 0.10 e Å^−3
1806 reflections	Δρmin = −0.10 e Å^−3
181 parameters	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
1 restraint	Absolute structure parameter: 1.0 (15)

Special details

Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fragment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-02-15_01-00-11

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

	x	y	z	Uiso*/Ueq
O2	0.31397 (17)	0.44525 (12)	1.01027 (8)	0.0366 (2)
O1	0.73608 (15)	0.44348 (13)	1.09800 (7)	0.0393 (2)
N1	0.8687 (2)	0.63339 (13)	0.87608 (10)	0.0249 (2)
H1A	0.934 (3)	0.642 (2)	0.7802 (17)	0.041 (4)
H1B	0.997 (3)	0.568 (2)	0.9444 (18)	0.047 (5)
H1C	0.837 (3)	0.755 (2)	0.9137 (17)	0.043 (5)
N3	0.72208 (19)	0.44672 (15)	0.38771 (8)	0.0321 (2)
H3	0.690 (3)	0.429 (3)	0.2813 (15)	0.052 (5)
N2	0.9189 (2)	0.51988 (13)	0.60207 (8)	0.0317 (2)
C1	0.5502 (2)	0.47060 (14)	1.00185 (9)	0.0237 (2)
C4	0.7011 (2)	0.41693 (13)	0.61567 (9)	0.0257 (3)
C6	0.5775 (3)	0.37123 (15)	0.48334 (10)	0.0314 (3)
H6	0.406 (3)	0.292 (3)	0.4481 (15)	0.065 (5)
C2	0.6172 (2)	0.53295 (14)	0.85629 (9)	0.0215 (2)
H2	0.465 (2)	0.6270 (19)	0.8093 (12)	0.032 (4)
C5	0.9232 (3)	0.53403 (17)	0.46361 (10)	0.0338 (3)
H5	1.071 (4)	0.608 (3)	0.4137 (14)	0.066 (5)
C3	0.6341 (3)	0.36806 (14)	0.75968 (10)	0.0298 (3)
H3A	0.774 (4)	0.275 (2)	0.8164 (17)	0.069 (6)
H3B	0.447 (4)	0.298 (3)	0.7443 (17)	0.075 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0264 (5)	0.0449 (5)	0.0406 (4)	0.0005 (4)	0.0121 (3)	0.0173 (4)
O1	0.0312 (5)	0.0676 (5)	0.0193 (3)	0.0019 (5)	0.0046 (3)	0.0101 (4)
N1	0.0284 (6)	0.0258 (5)	0.0208 (4)	−0.0035 (4)	0.0045 (4)	−0.0011 (4)
H1A	0.040 (13)	0.053 (12)	0.034 (9)	−0.006 (9)	0.016 (8)	0.011 (9)
H1B	0.031 (12)	0.045 (11)	0.060 (11)	−0.007 (9)	−0.017 (9)	0.014 (9)
H1C	0.054 (13)	0.031 (10)	0.048 (11)	0.021 (9)	0.017 (9)	−0.009 (8)
N3	0.0415 (6)	0.0374 (5)	0.0179 (3)	0.0017 (5)	0.0061 (3)	0.0004 (4)
H3	0.094 (14)	0.046 (11)	0.017 (7)	0.015 (12)	0.008 (8)	0.013 (8)
N2	0.0340 (6)	0.0397 (5)	0.0222 (4)	−0.0090 (4)	0.0063 (4)	−0.0016 (4)
C1	0.0257 (7)	0.0271 (5)	0.0192 (4)	0.0027 (4)	0.0069 (4)	0.0027 (3)
C4	0.0348 (7)	0.0253 (5)	0.0178 (4)	−0.0035 (4)	0.0067 (4)	−0.0015 (3)
C6	0.0399 (9)	0.0337 (6)	0.0205 (4)	−0.0049 (5)	0.0040 (5)	−0.0044 (4)
H6	0.073 (13)	0.080 (13)	0.037 (10)	−0.032 (11)	−0.011 (8)	−0.008 (9)
C2	0.0233 (6)	0.0246 (4)	0.0169 (4)	−0.0001 (4)	0.0043 (4)	0.0026 (3)
H2	0.024 (8)	0.028 (8)	0.043 (8)	0.006 (6)	−0.002 (6)	0.024 (7)
C5	0.0388 (9)	0.0416 (6)	0.0235 (5)	−0.0042 (6)	0.0129 (5)	0.0023 (4)
H5	0.078 (14)	0.090 (16)	0.036 (9)	−0.008 (12)	0.028 (8)	−0.006 (10)
C3	0.0463 (9)	0.0243 (5)	0.0200 (4)	−0.0084 (5)	0.0088 (4)	−0.0014 (4)
H3A	0.127 (19)	0.041 (11)	0.041 (10)	0.026 (12)	0.020 (11)	0.015 (8)
H3B	0.080 (16)	0.098 (15)	0.048 (11)	−0.066 (13)	0.015 (9)	−0.011 (11)

Geometric parameters (Å, º)

O2—C1	1.2529 (14)	N2—C5	1.3224 (13)
O1—C1	1.2461 (12)	C1—C2	1.5433 (13)
N1—H1A	1.018 (16)	C4—C6	1.3695 (13)
N1—H1B	0.988 (16)	C4—C3	1.5026 (13)
N1—H1C	0.988 (16)	C6—H6	1.076 (16)
N1—C2	1.4896 (14)	C2—H2	1.098 (12)
N3—H3	1.010 (14)	C2—C3	1.5366 (14)
N3—C6	1.3759 (15)	C5—H5	1.103 (18)
N3—C5	1.3455 (16)	C3—H3A	1.089 (17)
N2—C4	1.3833 (14)	C3—H3B	1.090 (17)
H1B—N1—H1A	110.0 (14)	H6—C6—N3	121.2 (8)
H1C—N1—H1A	110.9 (14)	H6—C6—C4	132.7 (8)
H1C—N1—H1B	109.8 (13)	C1—C2—N1	109.93 (8)
C2—N1—H1A	108.4 (9)	H2—C2—N1	107.5 (7)
C2—N1—H1B	109.5 (10)	H2—C2—C1	108.3 (7)
C2—N1—H1C	108.1 (10)	C3—C2—N1	110.38 (9)
C6—N3—H3	125.5 (11)	C3—C2—C1	109.68 (8)
C5—N3—H3	127.1 (11)	C3—C2—H2	111.0 (7)
C5—N3—C6	107.15 (9)	N2—C5—N3	111.92 (11)
C5—N2—C4	105.42 (9)	H5—C5—N3	122.8 (8)
O1—C1—O2	126.19 (10)	H5—C5—N2	125.3 (8)
C2—C1—O2	116.66 (8)	C2—C3—C4	113.12 (8)
C2—C1—O1	117.08 (11)	H3A—C3—C4	112.2 (10)
C6—C4—N2	109.39 (9)	H3A—C3—C2	107.4 (9)
C3—C4—N2	121.02 (9)	H3B—C3—C4	108.0 (8)
C3—C4—C6	129.58 (11)	H3B—C3—C2	109.3 (11)
C4—C6—N3	106.12 (11)	H3B—C3—H3A	106.5 (17)
C5—N2—C4—C3	178.65 (10)	O1—C1—C2—N1	−27.95 (13)
C6—N3—C5—N2	0.12 (15)	O2—C1—C2—C3	−83.69 (12)
O1—C1—C2—C3	93.59 (12)	C2—C3—C4—N2	53.66 (15)
N1—C2—C3—C4	−58.25 (13)	C3—C4—C6—N3	−178.44 (11)
C2—C3—C4—C6	−127.85 (13)	H1A—N1—C2—H2	−78.1 (11)
H1A—N1—C2—C1	164.3 (9)	H1B—N1—C2—H2	162.1 (12)
H1B—N1—C2—C1	44.4 (10)	H1C—N1—C2—H2	42.4 (12)
H1C—N1—C2—C1	−75.2 (10)	H3—N3—C5—N2	−174.7 (15)
C4—N2—C5—H5	179.8 (14)	H3—N3—C6—C4	174.7 (14)
H3—N3—C5—H5	6 (2)	O2—C1—C2—H2	37.6 (7)
H3—N3—C6—H6	−4.2 (19)	N1—C2—C3—H3A	66.2 (11)
C5—N2—C4—C6	−0.12 (13)	C1—C2—C3—H3B	60.1 (10)
C5—N3—C6—C4	−0.19 (14)	H2—C2—C3—H3B	−59.5 (12)
O2—C1—C2—N1	154.78 (9)	H3B—C3—C4—N2	174.9 (12)
C1—C2—C3—C4	−179.51 (10)	C3—C4—C6—H6	0.3 (15)
N2—C4—C6—N3	0.19 (13)	N1—C2—C3—H3B	−178.7 (10)
H1A—N1—C2—C3	43.2 (9)	H2—C2—C3—C4	60.9 (7)
H1B—N1—C2—C3	−76.7 (10)	H3A—C3—C4—N2	−68.0 (10)
H1C—N1—C2—C3	163.7 (10)	H3B—C3—C4—C6	−6.6 (12)
C6—N3—C5—H5	−179.7 (13)	C1—C2—C3—H3A	−55.1 (11)
C5—N3—C6—H6	−179.1 (13)	H2—C2—C3—H3A	−174.7 (12)
O1—C1—C2—H2	−145.1 (7)	H3A—C3—C4—C6	110.5 (10)
C4—N2—C5—N3	0.00 (14)	N2—C4—C6—H6	179.0 (15)

(HOTX21)

Crystal data

C6H9N3O2	Dx = 1.477 Mg m^−3
Mr = 155.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 7499 reflections
a = 5.1498 (2) Å	θ = 3.0–36.3°
b = 7.1902 (2) Å	µ = 0.11 mm^−1
c = 18.8503 (6) Å	T = 5 K
V = 697.99 (4) Å^3	Needle, colourless
Z = 4	0.2 × 0.1 × 0.1 mm
F(000) = 328.072

Data collection

Bruker APEX-II CCD diffractometer	2928 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics	2768 reflections with I ≥ 2u(I)
Multilayer optics monochromator	Rint = 0.027
φ scans	θmax = 36.3°, θmin = 3.0°
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10	h = −8→8
Tmin = 0.682, Tmax = 0.747	k = −10→10
13716 measured reflections	l = −28→28

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.019	w = 1/[σ^2(Fo^2) + (0.010P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.032	(Δ/σ)max = 0.0001
S = 1.13	Δρmax = 0.17 e Å^−3
2928 reflections	Δρmin = −0.13 e Å^−3
181 parameters	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
99 restraints	Absolute structure parameter: 0.1 (7)

Special details

Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-01-25_20-30-15

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

	x	y	z	Uiso*/Ueq
O2	0.32523 (5)	0.49519 (5)	0.239747 (17)	0.00711 (7)
O1	0.73277 (5)	0.49178 (6)	0.197479 (17)	0.00746 (7)
N1	0.91743 (7)	0.31183 (6)	0.31202 (2)	0.00606 (7)
N3	0.86938 (6)	0.50331 (6)	0.55327 (2)	0.00651 (7)
N2	1.03202 (6)	0.43924 (6)	0.44704 (2)	0.00638 (7)
C4	0.80291 (7)	0.53935 (6)	0.43875 (2)	0.00539 (8)
C1	0.56621 (7)	0.47000 (7)	0.24536 (2)	0.00510 (8)
C2	0.66640 (7)	0.41387 (7)	0.31927 (2)	0.00504 (8)
C6	0.70071 (8)	0.57917 (7)	0.50444 (2)	0.00626 (8)
C5	1.06292 (8)	0.42054 (7)	0.51647 (2)	0.00661 (8)
C3	0.70255 (8)	0.58731 (7)	0.36630 (2)	0.00640 (8)
H1B	1.0360 (14)	0.3760 (12)	0.2769 (4)	0.0172 (19)
H1C	0.8753 (15)	0.1814 (12)	0.2959 (4)	0.0205 (19)
H1A	1.0081 (14)	0.3117 (11)	0.3601 (4)	0.0172 (19)
H3	0.8465 (14)	0.5059 (12)	0.6068 (4)	0.0173 (19)
H2	0.5256 (12)	0.3202 (10)	0.3429 (4)	0.0172 (17)
H6	0.5315 (13)	0.6553 (10)	0.5190 (4)	0.0217 (18)
H5	1.2182 (12)	0.3487 (10)	0.5412 (3)	0.0208 (18)
H3A	0.8308 (14)	0.6852 (11)	0.3389 (4)	0.0203 (18)
H3B	0.5223 (14)	0.6553 (10)	0.3706 (4)	0.0243 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.00482 (10)	0.00938 (18)	0.00712 (15)	0.00064 (13)	−0.00049 (10)	0.00189 (12)
O1	0.00583 (10)	0.01196 (18)	0.00459 (15)	−0.00016 (12)	0.00017 (10)	0.00142 (12)
N1	0.00558 (13)	0.0068 (2)	0.00580 (19)	0.00100 (14)	−0.00005 (13)	−0.00024 (14)
N3	0.00740 (12)	0.0082 (2)	0.00394 (18)	0.00061 (14)	0.00015 (11)	0.00013 (14)
N2	0.00622 (11)	0.0083 (2)	0.00463 (19)	0.00177 (12)	−0.00029 (12)	−0.00033 (13)
C4	0.00607 (12)	0.0060 (2)	0.0041 (2)	0.00091 (14)	−0.00079 (13)	−0.00002 (14)
C1	0.00472 (13)	0.0058 (2)	0.0047 (2)	0.00020 (14)	−0.00039 (14)	−0.00005 (14)
C2	0.00474 (13)	0.0061 (2)	0.0043 (2)	0.00002 (15)	−0.00034 (13)	0.00045 (15)
C6	0.00628 (14)	0.0077 (2)	0.0048 (2)	0.00128 (15)	0.00000 (13)	−0.00053 (15)
C5	0.00626 (14)	0.0082 (2)	0.0054 (2)	0.00135 (16)	−0.00092 (14)	0.00041 (15)
C3	0.00775 (14)	0.0061 (2)	0.0053 (2)	0.00107 (16)	−0.00100 (14)	−0.00034 (15)
H1B	0.006 (3)	0.021 (5)	0.024 (4)	0.009 (2)	0.007 (2)	0.012 (2)
H1C	0.027 (4)	0.013 (3)	0.022 (4)	−0.0043 (19)	−0.003 (3)	−0.0055 (19)
H1A	0.015 (4)	0.020 (5)	0.016 (3)	−0.003 (3)	−0.0060 (17)	0.0018 (19)
H3	0.033 (4)	0.015 (5)	0.004 (3)	0.011 (4)	−0.0007 (16)	0.0018 (17)
H2	0.014 (3)	0.011 (4)	0.027 (4)	−0.002 (2)	−0.002 (2)	0.007 (2)
H6	0.018 (3)	0.025 (5)	0.022 (4)	0.008 (2)	0.005 (2)	0.002 (3)
H5	0.019 (3)	0.027 (5)	0.017 (4)	0.008 (2)	−0.002 (2)	0.004 (2)
H3A	0.023 (3)	0.022 (4)	0.016 (4)	−0.007 (2)	0.000 (2)	0.001 (2)
H3B	0.022 (3)	0.021 (4)	0.030 (5)	0.0085 (18)	−0.002 (2)	0.000 (3)

Geometric parameters (Å, º)

O2—C1	1.2586 (5)	N2—C5	1.3252 (6)
O1—C1	1.2550 (5)	C4—C6	1.3755 (6)
N1—H1B	1.012 (8)	C4—C3	1.5005 (6)
N1—H1A	1.019 (8)	C1—C2	1.5395 (6)
N1—H1C	1.010 (9)	C2—H2	1.085 (7)
N1—C2	1.4927 (5)	C2—C3	1.5413 (7)
N3—H3	1.017 (8)	C6—H6	1.065 (7)
N3—C6	1.3782 (6)	C5—H5	1.060 (6)
N3—C5	1.3524 (6)	C3—H3B	1.052 (7)
N2—C4	1.3909 (5)	C3—H3A	1.095 (7)
H1A—N1—H1B	107.8 (6)	H2—C2—N1	108.1 (4)
H1C—N1—H1B	110.8 (7)	H2—C2—C1	108.0 (4)
H1C—N1—H1A	111.5 (7)	C3—C2—N1	110.23 (3)
C2—N1—H1B	111.0 (4)	C3—C2—C1	110.42 (4)
C2—N1—H1A	108.4 (4)	C3—C2—H2	110.3 (4)
C2—N1—H1C	107.3 (5)	C4—C6—N3	106.12 (4)
C6—N3—H3	125.7 (4)	H6—C6—N3	123.2 (4)
C5—N3—H3	127.1 (4)	H6—C6—C4	130.7 (4)
C5—N3—C6	107.22 (4)	N2—C5—N3	111.93 (4)
C5—N2—C4	105.39 (4)	H5—C5—N3	123.0 (4)
C6—C4—N2	109.34 (4)	H5—C5—N2	125.1 (4)
C3—C4—N2	120.89 (4)	C2—C3—C4	112.28 (4)
C3—C4—C6	129.77 (4)	H3B—C3—C4	109.9 (4)
O1—C1—O2	126.55 (4)	H3B—C3—C2	108.3 (4)
C2—C1—O2	116.38 (4)	H3A—C3—C4	111.7 (4)
C2—C1—O1	117.03 (3)	H3A—C3—C2	108.7 (4)
C1—C2—N1	109.65 (4)	H3A—C3—H3B	105.6 (6)
C5—N2—C4—C3	−179.69 (4)	O1—C1—C2—N1	−26.72 (6)
C6—N3—C5—N2	0.58 (5)	O2—C1—C2—C3	−82.89 (5)
O1—C1—C2—C3	94.92 (5)	C2—C3—C4—N2	55.80 (5)
N1—C2—C3—C4	−58.08 (4)	C3—C4—C6—N3	−179.98 (7)
C2—C3—C4—C6	−123.97 (5)	H1A—N1—C2—H2	−79.9 (6)
H1A—N1—C2—C1	162.5 (5)	H1B—N1—C2—H2	161.9 (6)
H1B—N1—C2—C1	44.3 (5)	H1C—N1—C2—H2	40.5 (6)
H1C—N1—C2—C1	−77.1 (5)	H3—N3—C5—N2	178.4 (6)
C4—N2—C5—H5	179.0 (5)	H3—N3—C6—C4	−178.4 (6)
H3—N3—C5—H5	−1.0 (7)	O2—C1—C2—H2	37.8 (4)
H3—N3—C6—H6	3.3 (7)	N1—C2—C3—H3A	66.0 (4)
C5—N2—C4—C6	0.12 (5)	C1—C2—C3—H3B	59.1 (4)
C5—N3—C6—C4	−0.47 (5)	H2—C2—C3—H3B	−60.3 (6)
O2—C1—C2—N1	155.47 (4)	H3B—C3—C4—N2	176.4 (4)
C1—C2—C3—C4	−179.38 (3)	C3—C4—C6—H6	−1.8 (5)
N2—C4—C6—N3	0.22 (5)	N1—C2—C3—H3B	−179.6 (4)
H1A—N1—C2—C3	40.7 (5)	H2—C2—C3—C4	61.2 (4)
H1B—N1—C2—C3	−77.5 (5)	H3A—C3—C4—N2	−66.7 (4)
H1C—N1—C2—C3	161.2 (5)	H3B—C3—C4—C6	−3.4 (4)
C6—N3—C5—H5	−178.8 (4)	C1—C2—C3—H3A	−55.3 (4)
C5—N3—C6—H6	−178.8 (5)	H2—C2—C3—H3A	−174.6 (6)
O1—C1—C2—H2	−144.4 (4)	H3A—C3—C4—C6	113.6 (4)
C4—N2—C5—N3	−0.43 (5)	N2—C4—C6—H6	178.4 (5)

(HOTX22)

Crystal data

C6H9N3O2	Dx = 1.470 Mg m^−3
Mr = 155.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 6123 reflections
a = 5.1521 (1) Å	θ = 3.0–36.0°
b = 7.2228 (2) Å	µ = 0.11 mm^−1
c = 18.8440 (6) Å	T = 105 K
V = 701.23 (3) Å^3	Needle, colourless
Z = 4	0.2 × 0.1 × 0.1 mm
F(000) = 328.072

Data collection

Bruker APEX-II CCD diffractometer	2942 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics	2706 reflections with I ≥ 2u(I)
Multilayer optics monochromator	Rint = 0.030
φ scans	θmax = 36.3°, θmin = 3.0°
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10	h = −8→8
Tmin = 0.687, Tmax = 0.747	k = −10→10
13793 measured reflections	l = −28→28

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.023	w = 1/[σ^2(Fo^2) + (0.0119P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.038	(Δ/σ)max = 0.0001
S = 1.12	Δρmax = 0.17 e Å^−3
2942 reflections	Δρmin = −0.15 e Å^−3
181 parameters	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
99 restraints	Absolute structure parameter: 0.4 (8)

Special details

Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-01-23_23-40-43

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

	x	y	z	Uiso*/Ueq
O2	0.32475 (6)	0.49818 (6)	0.240209 (19)	0.01318 (8)
O1	0.73091 (6)	0.49455 (7)	0.197629 (19)	0.01394 (8)
N1	0.91616 (8)	0.31391 (7)	0.31181 (3)	0.00998 (9)
H1B	1.0343 (15)	0.3750 (13)	0.2770 (4)	0.020 (2)
H1A	1.0073 (14)	0.3128 (12)	0.3597 (5)	0.0157 (19)
H1C	0.8725 (17)	0.1843 (14)	0.2953 (5)	0.023 (2)
N3	0.87041 (7)	0.50257 (7)	0.55335 (3)	0.01189 (9)
H3	0.8494 (16)	0.5062 (13)	0.6068 (5)	0.026 (2)
N2	1.03224 (8)	0.43944 (7)	0.44706 (2)	0.01190 (9)
C4	0.80387 (9)	0.53942 (7)	0.43892 (3)	0.00996 (9)
C1	0.56511 (8)	0.47258 (8)	0.24558 (3)	0.00925 (9)
C2	0.66615 (8)	0.41601 (8)	0.31935 (3)	0.00865 (9)
H2	0.5257 (14)	0.3232 (11)	0.3427 (4)	0.0220 (19)
C6	0.70210 (9)	0.57890 (9)	0.50460 (3)	0.01133 (10)
H6	0.5334 (15)	0.6551 (11)	0.5199 (4)	0.028 (2)
C5	1.06326 (10)	0.41995 (8)	0.51647 (3)	0.01233 (10)
H5	1.2175 (15)	0.3476 (12)	0.5415 (4)	0.031 (2)
C3	0.70372 (10)	0.58790 (9)	0.36650 (3)	0.01170 (10)
H3B	0.5230 (16)	0.6543 (11)	0.3711 (4)	0.028 (2)
H3A	0.8329 (16)	0.6849 (12)	0.3400 (4)	0.027 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.00938 (12)	0.0168 (2)	0.01336 (19)	0.00099 (16)	−0.00125 (12)	0.00446 (16)
O1	0.01111 (13)	0.0235 (2)	0.00724 (18)	−0.00111 (15)	−0.00005 (12)	0.00319 (16)
N1	0.01021 (15)	0.0109 (3)	0.0088 (2)	0.00160 (17)	0.00013 (15)	−0.00024 (16)
H1B	0.009 (4)	0.028 (5)	0.022 (4)	0.007 (2)	0.003 (2)	0.013 (2)
H1A	0.013 (4)	0.018 (5)	0.016 (3)	0.000 (3)	−0.0041 (17)	0.0022 (19)
H1C	0.030 (5)	0.015 (4)	0.025 (5)	−0.004 (2)	−0.002 (3)	−0.007 (2)
N3	0.01415 (15)	0.0143 (2)	0.0072 (2)	−0.00054 (17)	0.00018 (14)	−0.00025 (17)
H3	0.045 (5)	0.025 (6)	0.007 (3)	0.012 (4)	0.0035 (17)	0.0044 (17)
N2	0.01215 (15)	0.0153 (3)	0.0083 (2)	0.00333 (16)	−0.00046 (15)	−0.00037 (16)
C4	0.01187 (15)	0.0103 (3)	0.0077 (2)	0.00147 (17)	−0.00122 (16)	−0.00048 (17)
C1	0.00919 (16)	0.0107 (3)	0.0079 (2)	−0.00063 (18)	−0.00100 (16)	0.00048 (17)
C2	0.00877 (16)	0.0101 (3)	0.0071 (2)	−0.00003 (18)	−0.00033 (16)	0.00073 (17)
H2	0.016 (3)	0.014 (4)	0.036 (5)	0.001 (2)	0.001 (3)	0.008 (3)
C6	0.01237 (17)	0.0129 (3)	0.0087 (2)	0.00133 (19)	0.00016 (17)	−0.00168 (18)
H6	0.024 (3)	0.031 (5)	0.027 (5)	0.009 (2)	0.005 (2)	−0.003 (3)
C5	0.01257 (18)	0.0156 (3)	0.0088 (3)	0.0011 (2)	−0.00196 (18)	0.00093 (19)
H5	0.029 (4)	0.040 (6)	0.026 (4)	0.014 (2)	−0.004 (2)	0.003 (3)
C3	0.01547 (19)	0.0104 (3)	0.0093 (3)	0.0027 (2)	−0.00243 (18)	−0.00081 (19)
H3B	0.029 (3)	0.023 (5)	0.033 (5)	0.0109 (19)	−0.005 (2)	−0.002 (3)
H3A	0.034 (4)	0.022 (4)	0.025 (4)	−0.007 (2)	0.004 (3)	0.001 (2)

Geometric parameters (Å, º)

O2—C1	1.2562 (5)	N2—C5	1.3253 (7)
O1—C1	1.2535 (6)	C4—C6	1.3739 (7)
N1—H1B	0.997 (8)	C4—C3	1.5005 (7)
N1—H1A	1.018 (8)	C1—C2	1.5396 (7)
N1—H1C	1.012 (9)	C2—H2	1.080 (8)
N1—C2	1.4910 (6)	C2—C3	1.5389 (8)
N3—H3	1.013 (9)	C6—H6	1.069 (7)
N3—C6	1.3784 (7)	C5—H5	1.061 (7)
N3—C5	1.3513 (7)	C3—H3B	1.051 (8)
N2—C4	1.3890 (6)	C3—H3A	1.088 (8)
H1A—N1—H1B	107.7 (7)	H2—C2—N1	108.1 (4)
H1C—N1—H1B	110.0 (7)	H2—C2—C1	107.8 (4)
H1C—N1—H1A	111.6 (7)	C3—C2—N1	110.20 (4)
C2—N1—H1B	111.8 (5)	C3—C2—C1	110.47 (5)
C2—N1—H1A	108.5 (5)	C3—C2—H2	110.5 (5)
C2—N1—H1C	107.2 (5)	C4—C6—N3	106.09 (4)
C6—N3—H3	125.8 (5)	H6—C6—N3	122.5 (5)
C5—N3—H3	127.0 (5)	H6—C6—C4	131.4 (5)
C5—N3—C6	107.25 (5)	N2—C5—N3	111.84 (5)
C5—N2—C4	105.44 (4)	H5—C5—N3	122.7 (4)
C6—C4—N2	109.38 (4)	H5—C5—N2	125.5 (4)
C3—C4—N2	120.86 (4)	C2—C3—C4	112.34 (5)
C3—C4—C6	129.76 (5)	H3B—C3—C4	109.6 (4)
O1—C1—O2	126.52 (5)	H3B—C3—C2	107.7 (4)
C2—C1—O2	116.43 (4)	H3A—C3—C4	110.9 (4)
C2—C1—O1	117.00 (4)	H3A—C3—C2	109.4 (4)
C1—C2—N1	109.71 (4)	H3A—C3—H3B	106.6 (6)
C5—N2—C4—C3	−179.64 (5)	O1—C1—C2—N1	−26.91 (7)
C6—N3—C5—N2	0.65 (7)	O2—C1—C2—C3	−82.89 (6)
O1—C1—C2—C3	94.78 (6)	C2—C3—C4—N2	55.98 (6)
N1—C2—C3—C4	−58.22 (6)	C3—C4—C6—N3	−180.00 (7)
C2—C3—C4—C6	−123.88 (6)	H1A—N1—C2—H2	−80.0 (7)
H1A—N1—C2—C1	162.6 (5)	H1B—N1—C2—H2	161.2 (7)
H1B—N1—C2—C1	43.9 (5)	H1C—N1—C2—H2	40.6 (7)
H1C—N1—C2—C1	−76.7 (6)	H3—N3—C5—N2	179.4 (6)
C4—N2—C5—H5	178.7 (6)	H3—N3—C6—C4	−179.3 (6)
H3—N3—C5—H5	0.1 (8)	O2—C1—C2—H2	37.9 (4)
H3—N3—C6—H6	2.4 (8)	N1—C2—C3—H3A	65.4 (5)
C5—N2—C4—C6	0.25 (6)	C1—C2—C3—H3B	59.5 (4)
C5—N3—C6—C4	−0.46 (6)	H2—C2—C3—H3B	−59.7 (6)
O2—C1—C2—N1	155.42 (5)	H3B—C3—C4—N2	175.7 (5)
C1—C2—C3—C4	−179.63 (4)	C3—C4—C6—H6	−1.8 (6)
N2—C4—C6—N3	0.13 (6)	N1—C2—C3—H3B	−179.1 (4)
H1A—N1—C2—C3	40.8 (5)	H2—C2—C3—C4	61.2 (4)
H1B—N1—C2—C3	−77.9 (5)	H3A—C3—C4—N2	−66.8 (5)
H1C—N1—C2—C3	161.4 (6)	H3B—C3—C4—C6	−4.1 (5)
C6—N3—C5—H5	−178.7 (5)	C1—C2—C3—H3A	−56.0 (5)
C5—N3—C6—H6	−178.8 (5)	H2—C2—C3—H3A	−175.2 (6)
O1—C1—C2—H2	−144.4 (4)	H3A—C3—C4—C6	113.4 (5)
C4—N2—C5—N3	−0.56 (6)	N2—C4—C6—H6	178.3 (6)

(HOTX23)

Crystal data

C6H9N3O2	Dx = 1.442 Mg m^−3
Mr = 155.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4787 reflections
a = 5.1690 (3) Å	θ = 3.0–32.3°
b = 7.3430 (5) Å	µ = 0.11 mm^−1
c = 18.8317 (13) Å	T = 295 K
V = 714.78 (8) Å^3	Needle, colourless
Z = 4	0.2 × 0.1 × 0.1 mm
F(000) = 328.073

Data collection

Bruker APEX-II CCD diffractometer	3008 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics	2569 reflections with I ≥ 2u(I)
Multilayer optics monochromator	Rint = 0.033
φ scans	θmax = 36.3°, θmin = 3.0°
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10	h = −8→8
Tmin = 0.648, Tmax = 0.747	k = −11→11
14091 measured reflections	l = −28→28

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0206P)^2 + 0.0062P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.054	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.16 e Å^−3
3008 reflections	Δρmin = −0.17 e Å^−3
181 parameters	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraints	Absolute structure parameter: 0.1 (11)

Special details

Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-01-19_19-23-38

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

	x	y	z	Uiso*/Ueq
O2	0.32399 (8)	0.50882 (8)	0.24194 (3)	0.03363 (13)
O1	0.72486 (9)	0.50473 (10)	0.19836 (3)	0.03629 (14)
N1	0.91181 (11)	0.32105 (9)	0.31064 (3)	0.02296 (11)
H1B	1.031 (2)	0.3861 (17)	0.2767 (6)	0.043 (3)
H1C	0.867 (2)	0.1949 (15)	0.2945 (6)	0.037 (3)
H1A	1.0053 (18)	0.3154 (16)	0.3575 (6)	0.032 (2)
N3	0.87440 (11)	0.49977 (9)	0.55355 (3)	0.02985 (13)
H3	0.852 (3)	0.5006 (17)	0.6066 (7)	0.049 (3)
N2	1.03303 (11)	0.43961 (9)	0.44716 (3)	0.02938 (13)
C4	0.80827 (12)	0.54010 (9)	0.43947 (3)	0.02360 (12)
C1	0.56258 (10)	0.48232 (9)	0.24645 (3)	0.02192 (12)
C2	0.66536 (10)	0.42348 (9)	0.31972 (3)	0.01979 (11)
H2	0.5262 (18)	0.3325 (13)	0.3427 (6)	0.036 (2)
C6	0.70825 (14)	0.57763 (11)	0.50522 (4)	0.02829 (14)
H6	0.546 (2)	0.6534 (18)	0.5216 (6)	0.061 (4)
C5	1.06397 (14)	0.41825 (12)	0.51634 (4)	0.03111 (15)
H5	1.213 (2)	0.3449 (19)	0.5411 (5)	0.062 (4)
C3	0.70836 (15)	0.59061 (11)	0.36742 (4)	0.02776 (14)
H3A	0.835 (3)	0.6820 (17)	0.3409 (6)	0.052 (3)
H3B	0.526 (2)	0.6577 (17)	0.3719 (6)	0.063 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.02204 (18)	0.0425 (3)	0.0363 (3)	0.0018 (2)	−0.00462 (18)	0.0138 (2)
O1	0.02826 (19)	0.0626 (4)	0.0180 (2)	−0.0029 (2)	−0.00110 (17)	0.0095 (2)
N1	0.0238 (2)	0.0253 (3)	0.0198 (3)	0.0040 (2)	−0.0001 (2)	−0.0005 (2)
H1B	0.032 (6)	0.053 (9)	0.043 (8)	0.008 (6)	0.018 (5)	0.025 (6)
H1C	0.044 (6)	0.014 (6)	0.052 (7)	0.003 (5)	0.000 (6)	−0.016 (6)
H1A	0.026 (5)	0.048 (7)	0.022 (6)	0.010 (5)	−0.001 (4)	0.003 (5)
N3	0.0367 (2)	0.0362 (4)	0.0167 (3)	−0.0030 (3)	−0.0005 (2)	−0.0013 (2)
H3	0.078 (9)	0.042 (9)	0.027 (7)	−0.008 (9)	0.000 (6)	0.003 (6)
N2	0.0302 (2)	0.0383 (3)	0.0196 (3)	0.0079 (2)	−0.0014 (2)	−0.0004 (2)
C4	0.0286 (2)	0.0247 (3)	0.0174 (3)	0.0025 (2)	−0.0027 (2)	−0.0020 (2)
C1	0.0212 (2)	0.0259 (3)	0.0187 (3)	−0.0020 (2)	−0.0036 (2)	0.0028 (2)
C2	0.0206 (2)	0.0226 (3)	0.0162 (3)	0.0004 (2)	−0.00109 (19)	0.0021 (2)
H2	0.032 (5)	0.021 (5)	0.054 (7)	−0.011 (5)	−0.002 (5)	0.013 (5)
C6	0.0306 (3)	0.0329 (4)	0.0214 (3)	0.0028 (3)	0.0008 (2)	−0.0057 (3)
H6	0.055 (7)	0.072 (9)	0.057 (8)	0.022 (7)	0.010 (6)	−0.020 (7)
C5	0.0324 (3)	0.0401 (4)	0.0208 (3)	0.0042 (3)	−0.0057 (3)	0.0021 (3)
H5	0.056 (6)	0.096 (10)	0.035 (7)	0.030 (7)	−0.001 (6)	0.016 (7)
C3	0.0385 (3)	0.0239 (4)	0.0209 (3)	0.0073 (3)	−0.0050 (3)	−0.0014 (3)
H3A	0.079 (8)	0.041 (7)	0.035 (6)	−0.018 (8)	−0.006 (6)	0.007 (6)
H3B	0.066 (8)	0.072 (9)	0.051 (8)	0.049 (7)	−0.022 (6)	−0.016 (7)

Geometric parameters (Å, º)

O1—C1	1.2453 (8)	C3—H3A	1.062 (14)
N2—C5	1.3219 (9)	N1—C2	1.4892 (8)
C2—C3	1.5370 (10)	N3—C6	1.3758 (10)
N1—H1A	1.007 (11)	C4—C6	1.3698 (10)
C2—H2	1.073 (10)	N1—H1C	1.002 (11)
C6—H6	1.053 (11)	C3—H3B	1.067 (11)
O2—C1	1.2514 (7)	N2—C4	1.3839 (9)
N3—C5	1.3452 (10)	C1—C2	1.5404 (8)
C3—C4	1.4984 (10)	N3—H3	1.006 (13)
N1—H1B	1.008 (11)	C5—H5	1.049 (11)
C4—N2—C5	105.54 (6)	C2—N1—H1B	110.9 (7)
O1—C1—C2	117.14 (5)	H1A—N1—H1C	109.8 (9)
N1—C2—C3	110.28 (5)	C6—N3—H3	125.6 (8)
N2—C4—C3	121.07 (6)	C3—C2—H2	111.0 (6)
N2—C5—N3	111.87 (7)	C4—C3—H3A	111.7 (7)
C2—N1—H1A	109.3 (6)	N2—C5—H5	126.0 (5)
H1A—N1—H1B	106.4 (9)	C4—C6—H6	132.2 (6)
C5—N3—H3	127.2 (8)	O1—C1—O2	126.44 (6)
C1—C2—H2	107.7 (6)	N1—C2—C1	109.50 (5)
C2—C3—H3B	106.7 (6)	C2—C3—C4	112.42 (6)
H3A—C3—H3B	106.9 (10)	C3—C4—C6	129.69 (6)
N3—C6—H6	121.5 (6)	C2—N1—H1C	107.7 (6)
C5—N3—C6	107.16 (6)	H1B—N1—H1C	112.8 (9)
O2—C1—C2	116.38 (5)	N1—C2—H2	107.8 (5)
C1—C2—C3	110.45 (5)	C2—C3—H3A	108.6 (6)
N2—C4—C6	109.24 (6)	C4—C3—H3B	110.3 (6)
N3—C6—C4	106.19 (6)	N3—C5—H5	122.1 (5)
C5—N2—C4—C3	−179.52 (7)	O1—C1—C2—N1	−27.33 (8)
C6—N3—C5—N2	0.61 (9)	O2—C1—C2—C3	−83.35 (7)
O1—C1—C2—C3	94.31 (7)	C2—C3—C4—N2	56.24 (8)
N1—C2—C3—C4	−58.88 (7)	C3—C4—C6—N3	179.83 (7)
C2—C3—C4—C6	−123.32 (8)	H1A—N1—C2—H2	−79.9 (9)
H1A—N1—C2—C1	163.2 (7)	H1B—N1—C2—H2	163.2 (9)
H1B—N1—C2—C1	46.3 (7)	H1C—N1—C2—H2	39.4 (9)
H1C—N1—C2—C1	−77.6 (7)	H3—N3—C5—N2	178.4 (10)
C4—N2—C5—H5	178.1 (9)	H3—N3—C6—C4	−178.3 (9)
H3—N3—C5—H5	−0.2 (13)	O2—C1—C2—H2	38.1 (6)
H3—N3—C6—H6	4.0 (12)	N1—C2—C3—H3A	65.2 (8)
C5—N2—C4—C6	0.12 (8)	C1—C2—C3—H3B	58.9 (7)
C5—N3—C6—C4	−0.49 (8)	H2—C2—C3—H3B	−60.6 (9)
O2—C1—C2—N1	155.01 (6)	H3B—C3—C4—N2	175.2 (7)
C1—C2—C3—C4	179.94 (5)	C3—C4—C6—H6	−2.9 (9)
N2—C4—C6—N3	0.23 (8)	N1—C2—C3—H3B	−179.9 (7)
H1A—N1—C2—C3	41.5 (7)	H2—C2—C3—C4	60.5 (6)
H1B—N1—C2—C3	−75.5 (7)	H3A—C3—C4—N2	−66.1 (8)
H1C—N1—C2—C3	160.7 (7)	H3B—C3—C4—C6	−4.4 (7)
C6—N3—C5—H5	−178.0 (8)	C1—C2—C3—H3A	−56.0 (8)
C5—N3—C6—H6	−178.1 (8)	H2—C2—C3—H3A	−175.4 (10)
O1—C1—C2—H2	−144.3 (6)	H3A—C3—C4—C6	114.3 (8)
C4—N2—C5—N3	−0.45 (9)	N2—C4—C6—H6	177.5 (9)