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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205252062100740X/um5050sup1.cif
Contains datablocks HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02, HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTN00sup2.hkl
Contains datablock HMTN00

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTN01sup3.hkl
Contains datablock HMTN01

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTN02sup4.hkl
Contains datablock HMTN02

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTN00sup5.hkl
Contains datablock HOTN00

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTN01sup6.hkl
Contains datablock HOTN01

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTN02sup7.hkl
Contains datablock HOTN02

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTX18sup8.hkl
Contains datablock HMTX18

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTX19sup9.hkl
Contains datablock HMTX19

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTX20sup10.hkl
Contains datablock HMTX20

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTX21sup11.hkl
Contains datablock HOTX21

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTX22sup12.hkl
Contains datablock HOTX22

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTX23sup13.hkl
Contains datablock HOTX23

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S205252062100740X/um5050sup14.pdf
Additional tables and figures

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205252062100740X/um5050sup15.cml
Supplementary material

CCDC references: 2097452; 2097453; 2097454; 2097455; 2097456; 2097457; 2097458; 2097459; 2097460; 2097461; 2097462; 2097463

Computing details top

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) top
Crystal data top
C6H9N3O2F(000) = 92
Mr = 155.16Dx = 1.464 Mg m3
Monoclinic, P21Neutron radiation, λ = 0.80 Å
a = 5.1651 (2) ÅCell parameters from 4301 reflections
b = 7.2324 (2) Åθ = 3.6–30.5°
c = 9.4957 (3) ŵ = 0.0 mm1
β = 97.065 (2)°T = 5 K
V = 352.03 (2) Å3Plate, colourless
Z = 20.45 × 0.35 × 0.30 mm
Data collection top
KOALA
diffractometer
Rint = 0.138
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australiaθmax = 71.1°
Laue scansh = 99
16604 measured reflectionsk = 1313
1629 independent reflectionsl = 1515
1267 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.060 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082(Δ/σ)max < 0.001
S = 1.21Δρmax = 1.62 e Å3
1629 reflectionsΔρmin = 1.99 e Å3
181 parametersAbsolute structure: Absolute structure known from synthesis
1 restraint
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.3153 (3)0.4532 (3)1.0159 (2)0.0075 (4)
O10.7418 (3)0.4476 (3)1.0990 (3)0.0089 (4)
N10.8766 (2)0.63531 (16)0.87289 (15)0.0071 (3)
H1A0.9462 (7)0.6394 (6)0.7740 (5)0.0197 (8)
H1B1.0169 (7)0.5658 (5)0.9425 (5)0.0218 (9)
H1C0.8500 (8)0.7702 (5)0.9113 (5)0.0201 (8)
N30.7208 (2)0.44435 (18)0.38771 (17)0.0079 (3)
H30.6899 (7)0.4374 (6)0.2770 (5)0.0203 (8)
N20.9220 (2)0.51526 (17)0.60102 (15)0.0074 (3)
C10.5534 (3)0.4757 (2)1.0048 (2)0.0052 (3)
C40.6990 (3)0.4138 (2)0.6167 (2)0.0069 (4)
C60.5721 (3)0.3694 (2)0.4843 (2)0.0069 (3)
H60.3963 (8)0.2908 (6)0.4535 (6)0.0232 (9)
C20.6204 (3)0.5360 (2)0.8578 (2)0.0056 (3)
H20.4702 (6)0.6330 (6)0.8096 (5)0.0189 (8)
C50.9266 (3)0.5300 (3)0.4619 (2)0.0076 (3)
H51.0729 (8)0.6031 (6)0.4118 (6)0.0244 (10)
C30.6302 (3)0.3659 (2)0.7616 (2)0.0066 (3)
H3A0.7723 (8)0.2667 (6)0.8134 (5)0.0214 (9)
H3B0.4375 (8)0.2981 (6)0.7524 (6)0.0248 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0047 (6)0.0086 (8)0.0093 (13)0.0003 (6)0.0014 (6)0.0016 (7)
O10.0054 (6)0.0104 (8)0.0104 (12)0.0007 (6)0.0010 (6)0.0013 (8)
N10.0066 (4)0.0055 (5)0.0093 (8)0.0006 (3)0.0011 (4)0.0005 (4)
H1A0.0160 (13)0.0258 (19)0.018 (3)0.0037 (13)0.0057 (14)0.0005 (17)
H1B0.0184 (14)0.0194 (19)0.026 (3)0.0011 (12)0.0021 (15)0.0066 (16)
H1C0.0250 (16)0.0116 (16)0.023 (3)0.0007 (12)0.0018 (16)0.0034 (14)
N30.0074 (4)0.0089 (5)0.0074 (9)0.0005 (4)0.0004 (4)0.0003 (4)
H30.0240 (15)0.026 (2)0.010 (3)0.0033 (15)0.0010 (14)0.0005 (15)
N20.0059 (4)0.0085 (5)0.0078 (8)0.0015 (4)0.0002 (4)0.0007 (5)
C10.0060 (5)0.0053 (7)0.0046 (11)0.0002 (5)0.0015 (5)0.0002 (5)
C40.0055 (5)0.0069 (7)0.0080 (11)0.0010 (5)0.0003 (5)0.0001 (6)
C60.0067 (5)0.0079 (7)0.0061 (11)0.0017 (5)0.0009 (6)0.0007 (6)
H60.0176 (15)0.031 (2)0.020 (3)0.0109 (14)0.0014 (15)0.0011 (17)
C20.0053 (5)0.0054 (7)0.0060 (10)0.0002 (5)0.0002 (5)0.0012 (6)
H20.0144 (12)0.0192 (17)0.022 (3)0.0052 (12)0.0012 (14)0.0029 (15)
C50.0070 (5)0.0084 (7)0.0079 (11)0.0015 (5)0.0025 (6)0.0002 (6)
H50.0215 (15)0.028 (2)0.026 (3)0.0107 (14)0.0098 (16)0.0017 (17)
C30.0086 (5)0.0060 (7)0.0053 (10)0.0023 (5)0.0016 (6)0.0005 (6)
H3A0.0301 (18)0.0166 (18)0.017 (3)0.0072 (14)0.0012 (16)0.0004 (14)
H3B0.0210 (16)0.025 (2)0.029 (3)0.0139 (14)0.0057 (17)0.0048 (17)
Geometric parameters (Å, º) top
O2—C11.258 (2)N2—C51.329 (2)
O1—C11.255 (3)C1—C21.542 (3)
N1—H1A1.046 (5)C4—C61.382 (3)
N1—H1B1.047 (4)C4—C31.503 (3)
N1—H1C1.056 (4)C2—H21.103 (4)
N1—C21.4970 (19)C2—C31.537 (2)
N3—H31.045 (5)C6—H61.081 (5)
N3—C61.378 (2)C3—H3A1.098 (5)
N3—C51.351 (2)C3—H3B1.103 (4)
N2—C41.3891 (19)C5—H51.080 (5)
C4—N2—C5105.40 (14)C3—C2—H2109.6 (3)
O1—C1—C2116.78 (16)C4—C3—H3A109.9 (3)
N1—C2—C3110.34 (13)N2—C5—H5125.2 (3)
N2—C4—C3120.82 (15)C4—C6—H6131.1 (3)
N2—C5—N3111.87 (15)O1—C1—O2126.9 (2)
C2—N1—H1A109.0 (3)N1—C2—C1110.08 (14)
C5—N3—H3124.0 (2)C2—C3—C4112.85 (13)
C1—C2—H2109.3 (3)C3—C4—C6129.79 (14)
C2—C3—H3B107.9 (3)C2—N1—H1C109.0 (2)
N3—C6—H6123.1 (3)N1—C2—H2107.6 (2)
C5—N3—C6107.49 (15)C2—C3—H3A109.0 (3)
O2—C1—C2116.30 (16)C4—C3—H3B110.0 (3)
C1—C2—C3109.83 (12)N3—C5—H5122.9 (3)
N2—C4—C6109.39 (15)H1B—N1—H1C109.6 (3)
N3—C6—C4105.86 (14)H1A—N1—H1C110.9 (4)
C2—N1—H1B111.4 (2)H1A—N1—H1B107.0 (3)
C6—N3—H3128.5 (2)H3A—C3—H3B107.0 (3)
C5—N2—C4—C3178.96 (15)O1—C1—C2—N127.5 (2)
C6—N3—C5—N20.2 (2)O2—C1—C2—C383.19 (19)
O1—C1—C2—C394.23 (19)C2—C3—C4—N253.59 (19)
N1—C2—C3—C457.55 (18)C3—C4—C6—N3178.75 (14)
C2—C3—C4—C6127.54 (17)H1A—N1—C2—H278.0 (4)
H1A—N1—C2—C1162.9 (3)H1B—N1—C2—H2164.2 (4)
H1B—N1—C2—C145.1 (3)H1C—N1—C2—H243.2 (4)
H1C—N1—C2—C175.9 (3)H3—N3—C5—N2178.7 (3)
C4—N2—C5—H5178.8 (3)H3—N3—C6—C4178.6 (3)
H3—N3—C5—H52.4 (5)O2—C1—C2—H237.1 (3)
H3—N3—C6—H60.2 (5)N1—C2—C3—H3A64.9 (3)
C5—N2—C4—C60.12 (17)C1—C2—C3—H3B59.2 (3)
C5—N3—C6—C40.23 (17)H2—C2—C3—H3B61.0 (4)
O2—C1—C2—N1155.13 (16)H3B—C3—C4—N2174.2 (3)
C1—C2—C3—C4179.07 (13)C3—C4—C6—H60.1 (4)
N2—C4—C6—N30.22 (16)N1—C2—C3—H3B179.3 (3)
H1A—N1—C2—C341.5 (3)H2—C2—C3—C460.8 (3)
H1B—N1—C2—C376.3 (3)H3A—C3—C4—N268.3 (3)
H1C—N1—C2—C3162.7 (3)H3B—C3—C4—C67.0 (3)
C6—N3—C5—H5178.7 (3)C1—C2—C3—H3A56.7 (3)
C5—N3—C6—H6179.0 (3)H2—C2—C3—H3A176.8 (3)
O1—C1—C2—H2145.5 (3)H3A—C3—C4—C6110.6 (3)
C4—N2—C5—N30.0 (2)N2—C4—C6—H6178.8 (3)
2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HMTN01) top
Crystal data top
C6H9N3O2F(000) = 92
Mr = 155.16Dx = 1.455 Mg m3
Monoclinic, P21Neutron radiation, λ = 0.80 Å
a = 5.1656 (2) ÅCell parameters from 2706 reflections
b = 7.2761 (3) Åθ = 3.5–30.4°
c = 9.4978 (3) ŵ = 0.0 mm1
β = 97.316 (3)°T = 105 K
V = 354.07 (2) Å3Plate, colourless
Z = 20.45 × 0.35 × 0.30 mm
Data collection top
KOALA
diffractometer
Rint = 0.149
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australiaθmax = 70.9°
Laue scansh = 88
12588 measured reflectionsk = 1212
1359 independent reflectionsl = 1414
939 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.071(Δ/σ)max < 0.001
S = 1.00Δρmax = 1.12 e Å3
1292 reflectionsΔρmin = 1.18 e Å3
181 parametersAbsolute structure: Absolute structure known from synthesis
1 restraint
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.3144 (4)0.4517 (4)1.0143 (3)0.0139 (5)
O10.7401 (4)0.4458 (4)1.0988 (3)0.0147 (5)
N10.8736 (2)0.63497 (19)0.87368 (17)0.0098 (3)
H1A0.9437 (8)0.6399 (7)0.7747 (5)0.0230 (9)
H1B1.0151 (8)0.5663 (6)0.9429 (6)0.0251 (10)
H1C0.8476 (8)0.7676 (6)0.9129 (5)0.0235 (10)
N30.7209 (2)0.4445 (2)0.38776 (19)0.0131 (3)
H30.6915 (8)0.4363 (7)0.2760 (6)0.0245 (10)
N20.9212 (2)0.5163 (2)0.60161 (18)0.0132 (3)
C10.5529 (3)0.4744 (2)1.0041 (2)0.0088 (4)
C40.6986 (3)0.4149 (3)0.6164 (2)0.0108 (4)
C60.5727 (3)0.3695 (3)0.4839 (2)0.0125 (4)
H60.3972 (9)0.2917 (7)0.4537 (6)0.0306 (11)
C20.6190 (3)0.5354 (3)0.8574 (2)0.0089 (4)
H20.4688 (7)0.6316 (7)0.8087 (5)0.0225 (9)
C50.9261 (3)0.5314 (3)0.4625 (2)0.0128 (4)
H51.0719 (9)0.6041 (7)0.4124 (6)0.0327 (12)
C30.6304 (4)0.3662 (3)0.7604 (2)0.0116 (4)
H3A0.7735 (10)0.2668 (7)0.8138 (6)0.0288 (11)
H3B0.4390 (10)0.2999 (7)0.7520 (6)0.0309 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0100 (7)0.0187 (12)0.0132 (16)0.0002 (9)0.0022 (8)0.0025 (10)
O10.0139 (8)0.0213 (11)0.0092 (14)0.0004 (9)0.0025 (8)0.0036 (10)
N10.0111 (5)0.0108 (7)0.0074 (10)0.0014 (4)0.0012 (5)0.0003 (5)
H1A0.0250 (16)0.033 (2)0.012 (3)0.0058 (17)0.0078 (17)0.001 (2)
H1B0.0232 (17)0.026 (2)0.024 (3)0.0007 (15)0.0052 (18)0.0060 (18)
H1C0.0269 (18)0.018 (2)0.025 (3)0.0013 (15)0.0016 (18)0.0078 (17)
N30.0169 (5)0.0152 (7)0.0075 (11)0.0006 (5)0.0030 (6)0.0013 (5)
H30.0302 (17)0.032 (2)0.011 (3)0.0014 (19)0.0007 (17)0.0032 (19)
N20.0134 (5)0.0165 (7)0.0097 (10)0.0030 (5)0.0016 (5)0.0004 (6)
C10.0093 (6)0.0101 (9)0.0072 (13)0.0012 (6)0.0022 (7)0.0015 (6)
C40.0125 (7)0.0113 (10)0.0091 (14)0.0005 (6)0.0025 (7)0.0004 (7)
C60.0132 (7)0.0130 (9)0.0113 (14)0.0017 (7)0.0009 (7)0.0024 (8)
H60.0273 (19)0.039 (3)0.024 (3)0.0147 (18)0.0010 (19)0.006 (2)
C20.0102 (6)0.0098 (8)0.0067 (11)0.0001 (6)0.0005 (6)0.0017 (7)
H20.0233 (15)0.024 (2)0.020 (3)0.0064 (16)0.0005 (17)0.0056 (18)
C50.0154 (7)0.0150 (9)0.0083 (13)0.0011 (7)0.0032 (8)0.0021 (8)
H50.033 (2)0.045 (3)0.021 (3)0.013 (2)0.009 (2)0.004 (2)
C30.0169 (7)0.0101 (9)0.0082 (13)0.0026 (7)0.0026 (8)0.0010 (8)
H3A0.045 (2)0.019 (2)0.023 (3)0.0102 (18)0.008 (2)0.0049 (18)
H3B0.035 (2)0.036 (3)0.024 (3)0.0228 (19)0.011 (2)0.008 (2)
Geometric parameters (Å, º) top
O1—C11.251 (3)C1—C21.542 (3)
N2—C51.329 (3)N1—H1A1.050 (5)
C2—C31.543 (3)C2—H21.102 (5)
O2—C11.259 (3)C6—H61.076 (5)
N3—C51.355 (2)N1—H1B1.046 (5)
C3—C41.498 (3)C3—H3A1.110 (6)
N1—C21.492 (2)N1—H1C1.049 (5)
N3—C61.377 (2)C3—H3B1.094 (6)
C4—C61.381 (3)N3—H31.055 (6)
N2—C41.388 (2)C5—H51.079 (5)
C4—N2—C5105.39 (15)C3—C2—H2109.5 (3)
O1—C1—C2117.24 (17)C4—C3—H3A110.6 (3)
N1—C2—C3110.43 (14)N2—C5—H5125.6 (3)
N2—C4—C3120.82 (17)C4—C6—H6130.7 (3)
N2—C5—N3111.69 (15)O1—C1—O2126.7 (2)
C2—N1—H1A108.9 (3)N1—C2—C1109.87 (14)
C5—N3—H3123.8 (3)C2—C3—C4112.81 (17)
C1—C2—H2109.7 (3)C3—C4—C6129.59 (17)
C2—C3—H3B107.0 (3)C2—N1—H1C109.4 (3)
N3—C6—H6123.5 (3)N1—C2—H2107.4 (3)
C5—N3—C6107.55 (16)C2—C3—H3A108.7 (3)
O2—C1—C2116.04 (19)C4—C3—H3B110.7 (3)
C1—C2—C3109.85 (16)N3—C5—H5122.8 (3)
N2—C4—C6109.57 (16)H1A—N1—H1B106.6 (4)
N3—C6—C4105.81 (15)H3A—C3—H3B106.8 (4)
C2—N1—H1B111.7 (3)H1A—N1—H1C111.1 (4)
C6—N3—H3128.6 (3)H1B—N1—H1C109.1 (4)
C5—N2—C4—C3178.71 (18)O1—C1—C2—N127.8 (3)
C6—N3—C5—N20.4 (2)O2—C1—C2—C383.5 (2)
O1—C1—C2—C393.9 (2)C2—C3—C4—N253.8 (2)
N1—C2—C3—C457.6 (2)C3—C4—C6—N3178.28 (19)
C2—C3—C4—C6128.1 (2)H1A—N1—C2—H277.9 (4)
H1A—N1—C2—C1162.9 (3)H1B—N1—C2—H2164.7 (4)
H1B—N1—C2—C145.4 (4)H1C—N1—C2—H243.8 (4)
H1C—N1—C2—C175.5 (3)H3—N3—C5—N2178.0 (3)
C4—N2—C5—H5179.0 (4)H3—N3—C6—C4178.1 (4)
H3—N3—C5—H52.6 (5)O2—C1—C2—H237.0 (4)
H3—N3—C6—H61.4 (6)N1—C2—C3—H3A65.4 (4)
C5—N2—C4—C60.3 (2)C1—C2—C3—H3B59.1 (4)
C5—N3—C6—C40.2 (2)H2—C2—C3—H3B61.5 (4)
O2—C1—C2—N1154.83 (19)H3B—C3—C4—N2173.7 (3)
C1—C2—C3—C4178.98 (14)C3—C4—C6—H61.2 (5)
N2—C4—C6—N30.1 (2)N1—C2—C3—H3B179.6 (3)
H1A—N1—C2—C341.5 (3)H2—C2—C3—C460.5 (3)
H1B—N1—C2—C375.9 (4)H3A—C3—C4—N268.1 (4)
H1C—N1—C2—C3163.2 (3)H3B—C3—C4—C68.2 (4)
C6—N3—C5—H5179.0 (4)C1—C2—C3—H3A56.0 (3)
C5—N3—C6—H6179.7 (4)H2—C2—C3—H3A176.5 (4)
O1—C1—C2—H2145.7 (3)H3A—C3—C4—C6109.9 (4)
C4—N2—C5—N30.5 (2)N2—C4—C6—H6179.4 (4)
2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HMTN02) top
Crystal data top
C6H9N3O2F(000) = 92
Mr = 155.16Dx = 1.428 Mg m3
Monoclinic, P21Neutron radiation, λ = 0.80 Å
a = 5.1854 (8) ÅCell parameters from 2412 reflections
b = 7.3998 (10) Åθ = 3.5–30.2°
c = 9.4976 (12) ŵ = 0.0 mm1
β = 98.182 (10)°T = 295 K
V = 360.72 (9) Å3Plate, colourless
Z = 20.45 × 0.35 × 0.30 mm
Data collection top
KOALA
diffractometer
Rint = 0.134
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australiaθmax = 71.1°
Laue scansh = 88
20381 measured reflectionsk = 1212
1354 independent reflectionsl = 1414
914 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.075(Δ/σ)max < 0.001
S = 1.11Δρmax = 0.77 e Å3
1354 reflectionsΔρmin = 1.00 e Å3
181 parametersAbsolute structure: Absolute structure known from synthesis
1 restraint
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.3140 (4)0.4452 (4)1.0099 (3)0.0370 (6)
O10.7363 (4)0.4425 (5)1.0976 (3)0.0390 (6)
N10.8685 (2)0.63321 (18)0.87612 (15)0.0248 (3)
H1A0.9374 (7)0.6423 (7)0.7783 (5)0.0418 (9)
H1B1.0086 (8)0.5653 (6)0.9439 (5)0.0440 (10)
H1C0.8387 (9)0.7618 (6)0.9167 (5)0.0427 (10)
N30.7224 (3)0.4469 (2)0.38768 (18)0.0328 (3)
H30.6923 (9)0.4379 (7)0.2775 (5)0.0466 (10)
N20.9193 (3)0.5192 (2)0.60256 (16)0.0327 (3)
C10.5499 (3)0.4701 (2)1.0022 (2)0.0235 (4)
C40.7008 (3)0.4168 (2)0.6159 (2)0.0259 (4)
C60.5766 (4)0.3713 (3)0.4831 (2)0.0313 (4)
H60.4032 (11)0.2932 (9)0.4506 (6)0.0630 (14)
C20.6168 (3)0.5329 (2)0.85666 (19)0.0216 (3)
H20.4651 (7)0.6251 (6)0.8071 (5)0.0412 (9)
C50.9234 (4)0.5343 (3)0.4633 (2)0.0338 (5)
H51.0673 (11)0.6101 (9)0.4149 (6)0.0662 (16)
C30.6338 (4)0.3682 (3)0.7597 (2)0.0300 (4)
H3A0.7794 (12)0.2737 (7)0.8139 (6)0.0565 (14)
H3B0.4455 (12)0.2979 (8)0.7484 (6)0.0641 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0277 (8)0.0461 (13)0.0394 (17)0.0012 (10)0.0122 (9)0.0168 (12)
O10.0322 (10)0.0660 (15)0.0190 (14)0.0030 (12)0.0038 (9)0.0093 (12)
N10.0275 (6)0.0273 (7)0.0202 (9)0.0043 (5)0.0053 (6)0.0020 (5)
H1A0.0407 (17)0.052 (2)0.035 (3)0.0099 (18)0.0123 (18)0.004 (2)
H1B0.041 (2)0.052 (3)0.037 (3)0.0032 (17)0.0010 (19)0.0026 (19)
H1C0.053 (2)0.034 (2)0.040 (3)0.0062 (17)0.0053 (19)0.0093 (17)
N30.0431 (7)0.0371 (7)0.0190 (10)0.0009 (6)0.0077 (6)0.0008 (6)
H30.059 (2)0.053 (3)0.027 (3)0.003 (2)0.0039 (19)0.002 (2)
N20.0377 (6)0.0410 (8)0.0205 (9)0.0086 (6)0.0077 (6)0.0009 (6)
C10.0254 (6)0.0284 (9)0.0180 (11)0.0026 (7)0.0070 (6)0.0033 (6)
C40.0331 (8)0.0263 (10)0.0193 (12)0.0032 (7)0.0076 (7)0.0015 (7)
C60.0375 (10)0.0364 (10)0.0196 (13)0.0054 (8)0.0030 (8)0.0030 (8)
H60.063 (3)0.079 (4)0.046 (4)0.030 (3)0.004 (2)0.010 (3)
C20.0247 (6)0.0244 (8)0.0164 (10)0.0006 (7)0.0052 (6)0.0026 (7)
H20.0376 (17)0.044 (2)0.042 (3)0.0065 (17)0.0062 (17)0.0107 (19)
C50.0404 (9)0.0402 (10)0.0236 (13)0.0048 (9)0.0135 (9)0.0006 (9)
H50.070 (3)0.091 (4)0.043 (3)0.028 (3)0.026 (3)0.006 (3)
C30.0460 (10)0.0249 (9)0.0204 (12)0.0072 (8)0.0090 (9)0.0008 (7)
H3A0.096 (4)0.040 (2)0.036 (3)0.019 (2)0.018 (3)0.0076 (19)
H3B0.082 (3)0.073 (3)0.041 (3)0.049 (3)0.021 (3)0.013 (2)
Geometric parameters (Å, º) top
O1—C11.244 (3)C3—H3A1.102 (6)
N2—C51.331 (2)N1—C21.4899 (19)
C2—C31.538 (3)N3—C61.379 (3)
N1—H1A1.044 (5)C4—C61.374 (3)
C2—H21.096 (4)N1—H1C1.046 (5)
C6—H61.077 (6)C3—H3B1.098 (7)
O2—C11.249 (3)N2—C41.384 (2)
N3—C51.344 (3)C1—C21.544 (3)
C3—C41.500 (3)N3—H31.038 (5)
N1—H1B1.030 (5)C5—H51.086 (6)
C4—N2—C5105.43 (16)C3—C2—H2109.6 (3)
O1—C1—C2116.82 (17)C4—C3—H3A110.2 (3)
N1—C2—C3110.20 (14)N2—C5—H5125.0 (4)
N2—C4—C3120.89 (16)C4—C6—H6131.2 (4)
N2—C5—N3111.70 (18)O1—C1—O2126.8 (2)
C2—N1—H1A109.1 (3)N1—C2—C1110.08 (14)
C5—N3—H3124.3 (3)C2—C3—C4113.31 (16)
C1—C2—H2109.5 (3)C3—C4—C6129.64 (16)
C2—C3—H3B107.9 (3)C2—N1—H1C109.0 (3)
N3—C6—H6122.9 (3)N1—C2—H2107.8 (2)
C5—N3—C6107.46 (16)C2—C3—H3A108.5 (3)
O2—C1—C2116.32 (19)C4—C3—H3B110.0 (3)
C1—C2—C3109.69 (13)N3—C5—H5123.3 (3)
N2—C4—C6109.46 (16)H1A—N1—H1B106.7 (4)
N3—C6—C4105.95 (17)H3A—C3—H3B106.6 (5)
C2—N1—H1B111.2 (3)H1A—N1—H1C110.9 (4)
C6—N3—H3128.2 (3)H1B—N1—H1C110.0 (4)
C5—N2—C4—C3178.91 (17)O1—C1—C2—N128.1 (3)
C6—N3—C5—N20.5 (2)O2—C1—C2—C383.8 (2)
O1—C1—C2—C393.4 (2)C2—C3—C4—N253.9 (2)
N1—C2—C3—C458.10 (19)C3—C4—C6—N3178.46 (17)
C2—C3—C4—C6127.7 (2)H1A—N1—C2—H276.7 (4)
H1A—N1—C2—C1163.9 (3)H1B—N1—C2—H2165.9 (4)
H1B—N1—C2—C146.6 (3)H1C—N1—C2—H244.5 (4)
H1C—N1—C2—C174.9 (3)H3—N3—C5—N2177.8 (4)
C4—N2—C5—H5178.2 (5)H3—N3—C6—C4177.9 (4)
H3—N3—C5—H53.5 (6)O2—C1—C2—H236.5 (3)
H3—N3—C6—H61.7 (6)N1—C2—C3—H3A64.6 (4)
C5—N2—C4—C60.2 (2)C1—C2—C3—H3B58.4 (4)
C5—N3—C6—C40.4 (2)H2—C2—C3—H3B61.8 (4)
O2—C1—C2—N1154.78 (19)H3B—C3—C4—N2174.8 (4)
C1—C2—C3—C4179.46 (14)C3—C4—C6—H61.1 (6)
N2—C4—C6—N30.2 (2)N1—C2—C3—H3B179.8 (3)
H1A—N1—C2—C342.8 (3)H2—C2—C3—C460.4 (3)
H1B—N1—C2—C374.6 (3)H3A—C3—C4—N267.9 (4)
H1C—N1—C2—C3164.0 (3)H3B—C3—C4—C66.7 (4)
C6—N3—C5—H5178.1 (4)C1—C2—C3—H3A56.7 (4)
C5—N3—C6—H6180.0 (5)H2—C2—C3—H3A176.9 (4)
O1—C1—C2—H2146.4 (3)H3A—C3—C4—C6110.5 (4)
C4—N2—C5—N30.4 (2)N2—C4—C6—H6179.7 (5)
2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HOTN00) top
Crystal data top
C6H9N3O2Dx = 1.476 Mg m3
Mr = 155.16Neutron radiation, λ = 0.80 Å
Orthorhombic, P212121Cell parameters from 7499 reflections
a = 5.1498 (2) Åθ = 3.0–36.3°
b = 7.1902 (2) ŵ = 0.0 mm1
c = 18.8503 (6) ÅT = 5 K
V = 697.99 (4) Å3Needle, colourless
Z = 40.35 × 0.30 × 0.15 mm
F(000) = 184
Data collection top
KOALA
diffractometer
Rint = 0.188
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australiaθmax = 71.2°
Laue scansh = 88
33762 measured reflectionsk = 1211
1375 independent reflectionsl = 2828
1133 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069(Δ/σ)max < 0.001
S = 1.15Δρmax = 1.49 e Å3
1375 reflectionsΔρmin = 1.34 e Å3
181 parametersAbsolute structure: Absolute structure known from synthesis
0 restraints
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.3252 (3)0.4947 (3)0.23962 (11)0.0082 (4)
O10.7328 (3)0.4917 (3)0.19749 (13)0.0081 (4)
N10.9182 (2)0.31158 (16)0.31208 (8)0.0076 (3)
N30.86952 (19)0.50364 (16)0.55338 (8)0.0074 (2)
N21.0322 (2)0.43916 (15)0.44681 (8)0.0076 (2)
C40.8030 (3)0.5395 (2)0.43874 (10)0.0064 (3)
C10.5658 (3)0.4701 (2)0.24520 (9)0.0062 (3)
C20.6666 (3)0.4137 (2)0.31917 (10)0.0050 (3)
C60.7008 (3)0.5791 (2)0.50449 (10)0.0065 (3)
C51.0628 (3)0.4205 (2)0.51652 (10)0.0076 (3)
C30.7027 (3)0.5874 (2)0.36619 (10)0.0073 (3)
H1B1.0426 (7)0.3791 (5)0.2769 (2)0.0194 (8)
H1C0.8794 (7)0.1770 (5)0.2951 (2)0.0205 (9)
H1A1.0122 (6)0.3102 (6)0.3610 (2)0.0177 (8)
H30.8478 (6)0.5046 (6)0.6090 (2)0.0193 (8)
H20.5255 (6)0.3176 (5)0.3444 (2)0.0169 (7)
H60.5285 (7)0.6556 (6)0.5201 (3)0.0247 (9)
H51.2224 (7)0.3478 (6)0.5415 (2)0.0240 (9)
H3A0.8371 (8)0.6849 (5)0.3397 (2)0.0234 (9)
H3B0.5139 (7)0.6563 (6)0.3713 (3)0.0236 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0045 (7)0.0086 (8)0.0114 (12)0.0006 (6)0.0006 (6)0.0015 (8)
O10.0049 (6)0.0116 (8)0.0077 (12)0.0000 (6)0.0007 (5)0.0005 (7)
N10.0069 (4)0.0063 (5)0.0096 (8)0.0011 (4)0.0004 (4)0.0009 (4)
N30.0071 (4)0.0087 (5)0.0063 (8)0.0001 (4)0.0001 (4)0.0012 (5)
N20.0063 (4)0.0078 (5)0.0087 (7)0.0018 (3)0.0003 (4)0.0011 (5)
C40.0065 (5)0.0066 (6)0.0062 (10)0.0005 (5)0.0005 (5)0.0010 (6)
C10.0053 (6)0.0053 (6)0.0079 (10)0.0001 (5)0.0001 (5)0.0005 (6)
C20.0042 (6)0.0055 (6)0.0053 (10)0.0006 (5)0.0002 (5)0.0007 (6)
C60.0057 (6)0.0078 (6)0.0060 (10)0.0015 (5)0.0009 (5)0.0009 (6)
C50.0067 (6)0.0085 (7)0.0078 (10)0.0018 (6)0.0000 (6)0.0002 (6)
C30.0082 (6)0.0050 (6)0.0086 (10)0.0018 (5)0.0015 (6)0.0006 (6)
H1B0.0186 (16)0.0177 (15)0.022 (3)0.0008 (13)0.0044 (15)0.0019 (14)
H1C0.0211 (15)0.0122 (15)0.028 (3)0.0009 (12)0.0011 (14)0.0077 (15)
H1A0.0156 (15)0.0229 (17)0.015 (2)0.0030 (12)0.0028 (13)0.0002 (16)
H30.0202 (15)0.0236 (16)0.014 (2)0.0019 (14)0.0009 (13)0.0000 (16)
H20.0145 (14)0.0191 (15)0.017 (2)0.0031 (12)0.0006 (13)0.0011 (15)
H60.0178 (16)0.0281 (19)0.028 (3)0.0095 (14)0.0026 (15)0.0035 (18)
H50.0201 (16)0.030 (2)0.022 (3)0.0099 (14)0.0060 (15)0.0042 (17)
H3A0.0277 (18)0.0184 (16)0.024 (3)0.0071 (15)0.0020 (16)0.0056 (16)
H3B0.0175 (16)0.030 (2)0.023 (3)0.0119 (13)0.0027 (15)0.0028 (17)
Geometric parameters (Å, º) top
O1—C11.254 (3)C3—H3A1.105 (4)
N2—C51.330 (2)N1—C21.4953 (19)
C2—C31.543 (2)N3—C61.378 (2)
N1—H1A1.042 (4)C4—C61.376 (3)
C2—H21.110 (4)N1—H1C1.039 (4)
C6—H61.085 (4)C3—H3B1.096 (4)
O2—C11.256 (2)N2—C41.3917 (18)
N3—C51.353 (2)C1—C21.542 (2)
C3—C41.502 (3)N3—H31.054 (4)
N1—H1B1.042 (4)C5—H51.082 (4)
C4—N2—C5105.11 (13)C3—C2—H2109.7 (2)
O1—C1—C2116.75 (15)C4—C3—H3A110.0 (2)
N1—C2—C3110.15 (12)N2—C5—H5124.7 (2)
N2—C4—C3120.67 (15)C4—C6—H6131.5 (3)
N2—C5—N3112.06 (13)O1—C1—O2126.80 (19)
C2—N1—H1A109.2 (2)N1—C2—C1109.88 (14)
C5—N3—H3126.3 (2)C2—C3—C4112.27 (13)
C1—C2—H2109.3 (2)C3—C4—C6129.87 (14)
C2—C3—H3B108.0 (3)C2—N1—H1C108.6 (2)
N3—C6—H6122.3 (3)N1—C2—H2107.5 (2)
C5—N3—C6107.12 (15)C2—C3—H3A109.3 (2)
O2—C1—C2116.41 (16)C4—C3—H3B109.2 (3)
C1—C2—C3110.31 (12)N3—C5—H5123.3 (3)
N2—C4—C6109.46 (15)H1A—N1—H1B106.4 (3)
N3—C6—C4106.24 (13)H3A—C3—H3B108.0 (3)
C2—N1—H1B111.2 (2)H1A—N1—H1C110.7 (3)
C6—N3—H3126.6 (2)H1B—N1—H1C110.9 (3)
C5—N2—C4—C3179.65 (13)O1—C1—C2—N126.6 (2)
C6—N3—C5—N20.80 (16)O2—C1—C2—C383.06 (19)
O1—C1—C2—C394.99 (19)C2—C3—C4—N255.75 (18)
N1—C2—C3—C458.05 (18)C3—C4—C6—N3179.92 (15)
C2—C3—C4—C6123.87 (17)H1A—N1—C2—H278.5 (3)
H1A—N1—C2—C1162.7 (3)H1B—N1—C2—H2164.4 (3)
H1B—N1—C2—C145.6 (3)H1C—N1—C2—H242.3 (3)
H1C—N1—C2—C176.6 (3)H3—N3—C5—N2178.1 (3)
C4—N2—C5—H5179.5 (3)H3—N3—C6—C4178.0 (3)
H3—N3—C5—H51.9 (4)O2—C1—C2—H237.6 (3)
H3—N3—C6—H63.4 (4)N1—C2—C3—H3A64.2 (3)
C5—N2—C4—C60.05 (16)C1—C2—C3—H3B60.0 (3)
C5—N3—C6—C40.72 (16)H2—C2—C3—H3B60.5 (4)
O2—C1—C2—N1155.31 (16)H3B—C3—C4—N2175.6 (3)
C1—C2—C3—C4179.52 (13)C3—C4—C6—H61.5 (4)
N2—C4—C6—N30.42 (16)N1—C2—C3—H3B178.5 (3)
H1A—N1—C2—C340.9 (3)H2—C2—C3—C460.0 (3)
H1B—N1—C2—C376.1 (3)H3A—C3—C4—N266.1 (3)
H1C—N1—C2—C3161.7 (3)H3B—C3—C4—C64.1 (3)
C6—N3—C5—H5179.2 (3)C1—C2—C3—H3A57.2 (3)
C5—N3—C6—H6179.3 (3)H2—C2—C3—H3A177.7 (3)
O1—C1—C2—H2144.3 (3)H3A—C3—C4—C6114.3 (3)
C4—N2—C5—N30.53 (16)N2—C4—C6—H6178.8 (3)
2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HOTN01) top
Crystal data top
C6H9N3O2Dx = 1.470 Mg m3
Mr = 155.16Neutron radiation, λ = 0.80 Å
Orthorhombic, P212121Cell parameters from 6123 reflections
a = 5.1521 (10) Åθ = 3.0–36.0°
b = 7.2228 (2) ŵ = 0.0 mm1
c = 18.8440 (6) ÅT = 105 K
V = 701.23 (14) Å3Needle, colourless
Z = 40.35 × 0.30 × 0.15 mm
F(000) = 184
Data collection top
KOALA
diffractometer
Rint = 0.214
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australiaθmax = 71.2°
Laue scansh = 88
32598 measured reflectionsk = 1211
1361 independent reflectionsl = 2828
1061 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max < 0.001
S = 1.15Δρmax = 1.27 e Å3
1361 reflectionsΔρmin = 1.10 e Å3
181 parametersAbsolute structure: Absolute structure known from synthesis
0 restraints
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.3242 (4)0.4979 (3)0.24007 (13)0.0147 (5)
O10.7306 (4)0.4942 (3)0.19789 (14)0.0151 (5)
N10.9167 (2)0.31345 (17)0.31167 (9)0.0114 (3)
H1B1.0391 (8)0.3799 (6)0.2768 (3)0.0239 (9)
H1C0.8786 (8)0.1799 (5)0.2943 (3)0.0253 (10)
H1A1.0097 (7)0.3110 (6)0.3610 (3)0.0239 (9)
N30.8707 (2)0.50253 (18)0.55332 (9)0.0127 (3)
H30.8483 (7)0.5046 (6)0.6092 (2)0.0248 (9)
N21.0323 (2)0.43948 (18)0.44686 (9)0.0130 (3)
C40.8041 (3)0.5392 (2)0.43910 (11)0.0110 (4)
C10.5648 (3)0.4728 (2)0.24541 (10)0.0108 (4)
C20.6660 (3)0.4161 (2)0.31938 (11)0.0088 (4)
H20.5255 (7)0.3212 (6)0.3440 (2)0.0222 (9)
C60.7018 (4)0.5786 (3)0.50489 (11)0.0120 (4)
H60.5312 (8)0.6534 (7)0.5202 (3)0.0322 (11)
C51.0634 (3)0.4201 (3)0.51659 (12)0.0136 (4)
H51.2222 (8)0.3459 (7)0.5419 (3)0.0317 (11)
C30.7043 (4)0.5885 (2)0.36664 (12)0.0129 (4)
H3A0.8376 (10)0.6834 (6)0.3400 (3)0.0310 (11)
H3B0.5166 (8)0.6576 (7)0.3708 (3)0.0328 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0112 (9)0.0174 (10)0.0156 (14)0.0003 (8)0.0018 (7)0.0040 (10)
O10.0096 (8)0.0235 (10)0.0122 (14)0.0012 (8)0.0006 (7)0.0021 (9)
N10.0103 (5)0.0124 (6)0.0115 (9)0.0022 (4)0.0003 (5)0.0003 (5)
H1B0.0246 (19)0.0253 (19)0.022 (3)0.0030 (15)0.0085 (17)0.0031 (16)
H1C0.0304 (19)0.0159 (17)0.029 (3)0.0028 (14)0.0022 (17)0.0046 (17)
H1A0.0211 (18)0.031 (2)0.019 (3)0.0051 (14)0.0030 (16)0.0010 (19)
N30.0149 (5)0.0152 (6)0.0079 (9)0.0004 (5)0.0006 (4)0.0009 (6)
H30.0282 (18)0.034 (2)0.012 (3)0.0018 (18)0.0025 (15)0.0039 (19)
N20.0135 (5)0.0151 (6)0.0105 (8)0.0033 (4)0.0000 (5)0.0012 (6)
C40.0117 (6)0.0100 (7)0.0114 (12)0.0012 (6)0.0002 (7)0.0002 (7)
C10.0088 (7)0.0111 (7)0.0126 (12)0.0007 (7)0.0019 (6)0.0000 (7)
C20.0087 (7)0.0081 (7)0.0096 (11)0.0009 (6)0.0003 (6)0.0013 (7)
H20.0216 (17)0.0230 (18)0.022 (3)0.0048 (15)0.0016 (16)0.0035 (17)
C60.0111 (7)0.0150 (8)0.0098 (12)0.0017 (7)0.0004 (6)0.0028 (7)
H60.0252 (19)0.042 (3)0.030 (3)0.0156 (18)0.0021 (19)0.008 (2)
C50.0133 (7)0.0162 (8)0.0112 (12)0.0041 (7)0.0033 (7)0.0002 (8)
H50.0270 (19)0.039 (2)0.029 (3)0.0138 (17)0.0068 (19)0.006 (2)
C30.0155 (8)0.0099 (8)0.0133 (12)0.0019 (7)0.0034 (7)0.0007 (8)
H3A0.041 (2)0.0249 (19)0.027 (3)0.0104 (19)0.003 (2)0.0066 (19)
H3B0.027 (2)0.038 (2)0.033 (3)0.0193 (17)0.009 (2)0.008 (2)
Geometric parameters (Å, º) top
O1—C11.247 (3)C3—H3A1.093 (5)
N2—C51.331 (3)N1—C21.4964 (19)
C2—C31.544 (2)N3—C61.376 (3)
N1—H1A1.046 (6)C4—C61.377 (3)
C2—H21.100 (4)N1—H1C1.037 (4)
C6—H61.071 (5)C3—H3B1.091 (5)
O2—C11.257 (3)N2—C41.3865 (19)
N3—C51.349 (2)C1—C21.544 (3)
C3—C41.502 (3)N3—H31.059 (4)
N1—H1B1.030 (5)C5—H51.088 (5)
C4—N2—C5105.12 (15)C3—C2—H2110.1 (3)
O1—C1—C2116.74 (17)C4—C3—H3A110.6 (3)
N1—C2—C3110.21 (14)N2—C5—H5125.1 (3)
N2—C4—C3120.62 (17)C4—C6—H6131.4 (4)
N2—C5—N3111.81 (15)O1—C1—O2126.9 (2)
C2—N1—H1A108.5 (3)N1—C2—C1109.59 (15)
C5—N3—H3126.6 (3)C2—C3—C4112.15 (13)
C1—C2—H2108.9 (2)C3—C4—C6129.69 (16)
C2—C3—H3B107.3 (3)C2—N1—H1C109.2 (2)
N3—C6—H6122.8 (4)N1—C2—H2107.5 (2)
C5—N3—C6107.55 (17)C2—C3—H3A108.8 (3)
O2—C1—C2116.34 (18)C4—C3—H3B110.3 (3)
C1—C2—C3110.50 (13)N3—C5—H5123.1 (3)
N2—C4—C6109.69 (17)H1A—N1—H1B107.1 (4)
N3—C6—C4105.82 (17)H3A—C3—H3B107.7 (4)
C2—N1—H1B111.1 (3)H1A—N1—H1C110.6 (4)
C6—N3—H3125.8 (2)H1B—N1—H1C110.4 (4)
C5—N2—C4—C3179.96 (15)O1—C1—C2—N126.9 (2)
C6—N3—C5—N20.7 (2)O2—C1—C2—C383.2 (2)
O1—C1—C2—C394.7 (2)C2—C3—C4—N256.3 (2)
N1—C2—C3—C458.4 (2)C3—C4—C6—N3179.61 (15)
C2—C3—C4—C6123.8 (2)H1A—N1—C2—H278.6 (4)
H1A—N1—C2—C1163.2 (3)H1B—N1—C2—H2163.9 (4)
H1B—N1—C2—C145.7 (3)H1C—N1—C2—H242.0 (4)
H1C—N1—C2—C176.2 (4)H3—N3—C5—N2178.6 (3)
C4—N2—C5—H5178.8 (4)H3—N3—C6—C4178.5 (3)
H3—N3—C5—H50.7 (5)O2—C1—C2—H237.9 (3)
H3—N3—C6—H62.5 (5)N1—C2—C3—H3A64.2 (3)
C5—N2—C4—C60.15 (19)C1—C2—C3—H3B59.1 (4)
C5—N3—C6—C40.6 (2)H2—C2—C3—H3B61.3 (4)
O2—C1—C2—N1155.17 (16)H3B—C3—C4—N2175.8 (3)
C1—C2—C3—C4179.71 (14)C3—C4—C6—H60.7 (5)
N2—C4—C6—N30.3 (2)N1—C2—C3—H3B179.7 (3)
H1A—N1—C2—C341.4 (3)H2—C2—C3—C460.0 (3)
H1B—N1—C2—C376.1 (4)H3A—C3—C4—N265.2 (3)
H1C—N1—C2—C3162.0 (4)H3B—C3—C4—C64.3 (4)
C6—N3—C5—H5178.6 (4)C1—C2—C3—H3A57.1 (3)
C5—N3—C6—H6179.6 (4)H2—C2—C3—H3A177.5 (4)
O1—C1—C2—H2144.2 (3)H3A—C3—C4—C6114.6 (3)
C4—N2—C5—N30.53 (19)N2—C4—C6—H6179.2 (4)
2-Amino-3-(1H-imidazol-4-yl)propanoic acid (HOTN02) top
Crystal data top
C6H9N3O2Dx = 1.442 Mg m3
Mr = 155.16Neutron radiation, λ = 0.80 Å
Orthorhombic, P212121Cell parameters from 4787 reflections
a = 5.1690 (3) Åθ = 3.0–32.3°
b = 7.3430 (5) ŵ = 0.0 mm1
c = 18.8317 (13) ÅT = 295 K
V = 714.78 (8) Å3Needle, colourless
Z = 40.35 × 0.30 × 0.15 mm
F(000) = 184
Data collection top
KOALA
diffractometer
Rint = 0.237
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australiaθmax = 70.9°
Laue scansh = 77
32190 measured reflectionsk = 1111
1104 independent reflectionsl = 2626
781 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max < 0.001
S = 1.19Δρmax = 0.67 e Å3
1104 reflectionsΔρmin = 0.65 e Å3
181 parametersAbsolute structure: Absolute structure known from synthesis
0 restraints
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.3241 (6)0.5093 (4)0.24197 (18)0.0374 (8)
O10.7255 (6)0.5056 (5)0.1988 (2)0.0399 (8)
N10.9129 (4)0.3213 (2)0.31058 (13)0.0274 (4)
H1B1.0310 (11)0.3850 (8)0.2762 (4)0.0461 (14)
H1C0.8690 (11)0.1909 (8)0.2926 (3)0.0450 (14)
H1A1.0058 (9)0.3154 (8)0.3593 (3)0.0406 (13)
N30.8748 (3)0.4997 (3)0.55358 (12)0.0322 (4)
H30.8527 (11)0.4994 (8)0.6087 (4)0.0483 (14)
N21.0323 (3)0.4398 (2)0.44699 (11)0.0334 (5)
C40.8077 (5)0.5400 (3)0.43942 (14)0.0265 (5)
C10.5626 (5)0.4821 (3)0.24611 (13)0.0258 (6)
C20.6649 (4)0.4240 (3)0.31964 (13)0.0229 (5)
H20.5241 (9)0.3313 (8)0.3445 (3)0.0407 (13)
C60.7065 (5)0.5766 (4)0.50536 (15)0.0329 (7)
H60.5344 (12)0.6503 (10)0.5214 (4)0.0586 (17)
C51.0649 (5)0.4188 (4)0.51627 (16)0.0341 (6)
H51.2206 (13)0.3431 (10)0.5413 (4)0.0606 (18)
C30.7079 (6)0.5905 (3)0.36726 (15)0.0311 (6)
H3A0.8392 (15)0.6853 (9)0.3410 (4)0.0595 (19)
H3B0.5253 (13)0.6609 (9)0.3727 (4)0.0627 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0230 (14)0.0439 (19)0.045 (2)0.0002 (13)0.0064 (12)0.0150 (16)
O10.0304 (14)0.063 (2)0.027 (2)0.0015 (14)0.0001 (11)0.0094 (16)
N10.0278 (9)0.0278 (9)0.0266 (14)0.0061 (7)0.0012 (9)0.0019 (9)
H1B0.044 (3)0.051 (3)0.044 (4)0.011 (3)0.005 (3)0.001 (3)
H1C0.052 (3)0.037 (3)0.046 (4)0.004 (2)0.006 (3)0.006 (3)
H1A0.033 (3)0.055 (3)0.034 (4)0.013 (2)0.001 (2)0.001 (3)
N30.0383 (10)0.0378 (10)0.0205 (13)0.0013 (8)0.0002 (7)0.0017 (9)
H30.060 (4)0.055 (3)0.030 (4)0.003 (3)0.005 (3)0.001 (3)
N20.0315 (9)0.0418 (11)0.0270 (13)0.0077 (7)0.0007 (8)0.0010 (9)
C40.0328 (11)0.0250 (12)0.0217 (16)0.0009 (9)0.0026 (10)0.0027 (11)
C10.0235 (11)0.0296 (12)0.0242 (17)0.0007 (10)0.0013 (9)0.0027 (11)
C20.0244 (11)0.0242 (11)0.0202 (15)0.0011 (9)0.0020 (9)0.0028 (9)
H20.031 (2)0.053 (3)0.039 (4)0.011 (2)0.005 (2)0.007 (3)
C60.0330 (13)0.0395 (15)0.0262 (18)0.0055 (12)0.0022 (11)0.0054 (12)
H60.050 (3)0.075 (4)0.051 (4)0.026 (3)0.007 (3)0.007 (3)
C50.0343 (13)0.0453 (16)0.0226 (17)0.0068 (13)0.0041 (12)0.0002 (13)
H50.058 (4)0.077 (4)0.047 (5)0.022 (3)0.019 (3)0.006 (3)
C30.0452 (15)0.0224 (12)0.0257 (18)0.0073 (11)0.0072 (12)0.0015 (11)
H3A0.093 (5)0.047 (3)0.038 (4)0.022 (4)0.010 (4)0.010 (3)
H3B0.069 (5)0.065 (4)0.054 (5)0.028 (3)0.008 (4)0.017 (3)
Geometric parameters (Å, º) top
O1—C11.238 (4)C3—H3A1.091 (8)
N2—C51.325 (4)N1—C21.497 (3)
C2—C31.532 (3)N3—C61.379 (3)
N1—H1A1.037 (6)C4—C61.374 (4)
C2—H21.101 (6)N1—H1C1.041 (6)
C6—H61.084 (7)C3—H3B1.081 (7)
O2—C11.251 (4)N2—C41.382 (3)
N3—C51.346 (3)C1—C21.542 (3)
C3—C41.500 (4)N3—H31.044 (8)
N1—H1B1.005 (7)C5—H51.086 (8)
C4—N2—C5105.7 (2)C3—C2—H2109.9 (4)
O1—C1—C2116.8 (3)C4—C3—H3A110.8 (5)
N1—C2—C3110.15 (19)N2—C5—H5125.6 (5)
N2—C4—C3120.9 (2)C4—C6—H6131.4 (5)
N2—C5—N3111.7 (2)O1—C1—O2127.1 (3)
C2—N1—H1A108.5 (3)N1—C2—C1109.3 (2)
C5—N3—H3126.7 (4)C2—C3—C4112.51 (19)
C1—C2—H2109.0 (3)C3—C4—C6129.8 (2)
C2—C3—H3B108.1 (4)C2—N1—H1C108.3 (4)
N3—C6—H6122.6 (5)N1—C2—H2107.6 (3)
C5—N3—C6107.3 (2)C2—C3—H3A109.5 (4)
O2—C1—C2116.0 (2)C4—C3—H3B109.4 (5)
C1—C2—C3110.76 (19)N3—C5—H5122.7 (5)
N2—C4—C6109.3 (2)H1A—N1—H1B108.0 (5)
N3—C6—C4106.0 (2)H3A—C3—H3B106.3 (6)
C2—N1—H1B111.0 (4)H1A—N1—H1C110.5 (5)
C6—N3—H3125.9 (4)H1B—N1—H1C110.6 (5)
C5—N2—C4—C3179.9 (2)O1—C1—C2—N128.0 (3)
C6—N3—C5—N20.6 (3)O2—C1—C2—C383.0 (3)
O1—C1—C2—C393.5 (3)C2—C3—C4—N256.3 (3)
N1—C2—C3—C458.9 (3)C3—C4—C6—N3179.9 (2)
C2—C3—C4—C6122.8 (3)H1A—N1—C2—H277.7 (5)
H1A—N1—C2—C1164.0 (4)H1B—N1—C2—H2163.8 (6)
H1B—N1—C2—C145.5 (5)H1C—N1—C2—H242.3 (5)
H1C—N1—C2—C176.0 (4)H3—N3—C5—N2177.9 (4)
C4—N2—C5—H5178.2 (5)H3—N3—C6—C4178.2 (5)
H3—N3—C5—H50.5 (7)O2—C1—C2—H238.1 (4)
H3—N3—C6—H62.4 (7)N1—C2—C3—H3A64.7 (5)
C5—N2—C4—C60.5 (3)C1—C2—C3—H3B59.1 (5)
C5—N3—C6—C40.9 (3)H2—C2—C3—H3B61.4 (6)
O2—C1—C2—N1155.5 (2)H3B—C3—C4—N2176.5 (4)
C1—C2—C3—C4180.0 (2)C3—C4—C6—H60.6 (7)
N2—C4—C6—N30.9 (3)N1—C2—C3—H3B179.9 (5)
H1A—N1—C2—C342.1 (4)H2—C2—C3—C459.5 (4)
H1B—N1—C2—C376.4 (5)H3A—C3—C4—N266.6 (5)
H1C—N1—C2—C3162.1 (4)H3B—C3—C4—C62.7 (5)
C6—N3—C5—H5177.7 (5)C1—C2—C3—H3A56.3 (5)
C5—N3—C6—H6179.7 (5)H2—C2—C3—H3A176.9 (5)
O1—C1—C2—H2145.4 (4)H3A—C3—C4—C6114.2 (5)
C4—N2—C5—N30.1 (3)N2—C4—C6—H6179.8 (6)
(HMTX18) top
Crystal data top
C6H9N3O2F(000) = 164.036
Mr = 155.16Dx = 1.464 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 5.1651 (2) ÅCell parameters from 4301 reflections
b = 7.2324 (2) Åθ = 3.6–30.5°
c = 9.4957 (3) ŵ = 0.11 mm1
β = 97.065 (2)°T = 5 K
V = 352.03 (2) Å3Plate, colourless
Z = 20.2 × 0.2 × 0.1 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2138 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics2087 reflections with I 2u(I)
Multilayer optics monochromatorRint = 0.025
φ scansθmax = 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 = 77
Tmin = 0.687, Tmax = 0.746k = 1010
11118 measured reflectionsl = 1313
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.017 w = 1/[σ2(Fo2) + (0.0081P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.029(Δ/σ)max = 0.001
S = 1.28Δρmax = 0.12 e Å3
2138 reflectionsΔρmin = 0.10 e Å3
181 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
100 restraintsAbsolute structure parameter: 0.4 (9)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O20.31533 (7)0.45284 (5)1.01583 (3)0.00805 (8)
O10.74155 (7)0.44673 (6)1.09914 (3)0.00847 (8)
N10.87626 (10)0.63462 (6)0.87300 (4)0.00670 (9)
H1A0.9395 (16)0.6386 (12)0.7759 (8)0.0180 (19)
H1B1.0107 (16)0.5691 (12)0.9411 (8)0.016 (2)
H1C0.8493 (17)0.7655 (12)0.9094 (9)0.019 (2)
N30.72055 (9)0.44327 (7)0.38766 (4)0.00739 (9)
H30.6885 (14)0.4347 (13)0.2818 (7)0.0134 (19)
N20.92189 (9)0.51432 (6)0.60095 (4)0.00714 (10)
C10.55412 (11)0.47508 (7)1.00470 (5)0.00581 (10)
C40.69853 (11)0.41306 (7)0.61655 (5)0.00627 (11)
C60.57237 (11)0.36816 (8)0.48466 (5)0.00733 (11)
H60.3961 (15)0.2918 (12)0.4530 (7)0.022 (2)
C20.62067 (10)0.53564 (7)0.85771 (5)0.00583 (10)
H20.4708 (13)0.6313 (10)0.8108 (6)0.0117 (17)
C50.92631 (11)0.52932 (8)0.46208 (5)0.00783 (11)
H51.0721 (15)0.6038 (11)0.4133 (7)0.026 (2)
C30.62991 (12)0.36483 (7)0.76129 (5)0.00731 (11)
H3A0.7703 (15)0.2692 (11)0.8163 (8)0.0230 (19)
H3B0.4355 (15)0.3026 (11)0.7513 (7)0.0201 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.00614 (19)0.00906 (18)0.00920 (14)0.00018 (17)0.00196 (13)0.00264 (14)
O10.0071 (2)0.01195 (18)0.00635 (14)0.00011 (18)0.00069 (12)0.00161 (14)
N10.0071 (2)0.0060 (2)0.00698 (18)0.00118 (19)0.00082 (17)0.00020 (16)
H1A0.022 (5)0.021 (5)0.012 (2)0.006 (3)0.0058 (14)0.0043 (16)
H1B0.015 (4)0.016 (4)0.015 (3)0.001 (2)0.0047 (18)0.0038 (18)
H1C0.022 (5)0.012 (3)0.023 (4)0.0021 (17)0.005 (3)0.0029 (15)
N30.0087 (2)0.0079 (2)0.00553 (16)0.00014 (19)0.00092 (14)0.00005 (16)
H30.016 (4)0.015 (5)0.009 (2)0.002 (3)0.0011 (12)0.0015 (13)
N20.0070 (2)0.0078 (2)0.00656 (17)0.00197 (18)0.00065 (15)0.00049 (15)
C10.0063 (3)0.0053 (3)0.00605 (18)0.0003 (2)0.00129 (17)0.00000 (17)
C40.0073 (3)0.0064 (3)0.00533 (19)0.0005 (2)0.00162 (17)0.00000 (16)
C60.0079 (3)0.0076 (3)0.0063 (2)0.0012 (2)0.00037 (18)0.00089 (18)
H60.017 (3)0.027 (5)0.021 (4)0.0114 (19)0.0002 (19)0.001 (3)
C20.0060 (3)0.0064 (2)0.00523 (19)0.0002 (2)0.00109 (17)0.00051 (18)
H20.010 (4)0.002 (3)0.022 (4)0.0009 (17)0.002 (2)0.004 (2)
C50.0082 (3)0.0081 (2)0.0075 (2)0.0008 (2)0.00207 (18)0.00025 (18)
H50.028 (4)0.034 (6)0.018 (4)0.016 (2)0.0074 (18)0.004 (2)
C30.0096 (3)0.0061 (2)0.0064 (2)0.0014 (2)0.00139 (18)0.00036 (17)
H3A0.028 (4)0.014 (4)0.025 (4)0.0066 (18)0.005 (2)0.001 (2)
H3B0.016 (3)0.020 (4)0.024 (4)0.0069 (15)0.0021 (17)0.002 (3)
Geometric parameters (Å, º) top
O2—C11.2611 (6)N2—C51.3261 (6)
O1—C11.2530 (6)C1—C21.5415 (7)
N1—H1A1.016 (7)C4—C61.3776 (6)
N1—H1B1.007 (8)C4—C31.5020 (7)
N1—H1C1.023 (9)C6—H61.076 (7)
N1—C21.4930 (7)C2—H21.091 (7)
N3—H31.000 (6)C2—C31.5419 (7)
N3—C61.3794 (7)C5—H51.076 (7)
N3—C51.3533 (7)C3—H3A1.088 (7)
N2—C41.3897 (7)C3—H3B1.094 (8)
H1B—N1—H1A108.8 (6)H6—C6—N3122.4 (4)
H1C—N1—H1A110.6 (7)H6—C6—C4131.6 (4)
H1C—N1—H1B109.3 (6)C1—C2—N1109.95 (4)
C2—N1—H1A107.7 (5)H2—C2—N1108.1 (4)
C2—N1—H1B111.6 (5)H2—C2—C1108.9 (4)
C2—N1—H1C108.7 (5)C3—C2—N1110.51 (4)
C6—N3—H3127.6 (4)C3—C2—C1109.67 (4)
C5—N3—H3125.1 (4)C3—C2—H2109.7 (3)
C5—N3—C6107.28 (4)N2—C5—N3111.91 (5)
C5—N2—C4105.37 (4)H5—C5—N3123.5 (4)
O1—C1—O2126.63 (5)H5—C5—N2124.6 (4)
C2—C1—O2116.20 (4)C2—C3—C4112.66 (4)
C2—C1—O1117.12 (5)H3A—C3—C4111.6 (4)
C6—C4—N2109.48 (4)H3A—C3—C2107.0 (4)
C3—C4—N2120.82 (4)H3B—C3—C4109.5 (4)
C3—C4—C6129.69 (5)H3B—C3—C2106.6 (4)
C4—C6—N3105.96 (5)H3B—C3—H3A109.3 (6)
C5—N2—C4—C3178.91 (5)O1—C1—C2—N127.41 (6)
C6—N3—C5—N20.25 (7)O2—C1—C2—C383.27 (6)
O1—C1—C2—C394.30 (6)C2—C3—C4—N253.66 (7)
N1—C2—C3—C457.64 (6)C3—C4—C6—N3178.61 (5)
C2—C3—C4—C6127.97 (6)H1A—N1—C2—H277.8 (6)
H1A—N1—C2—C1163.5 (5)H1B—N1—C2—H2162.8 (6)
H1B—N1—C2—C144.1 (5)H1C—N1—C2—H242.2 (6)
H1C—N1—C2—C176.5 (5)H3—N3—C5—N2178.3 (6)
C4—N2—C5—H5178.1 (5)H3—N3—C6—C4178.4 (6)
H3—N3—C5—H53.3 (8)O2—C1—C2—H236.8 (4)
H3—N3—C6—H61.6 (8)N1—C2—C3—H3A65.4 (4)
C5—N2—C4—C60.24 (6)C1—C2—C3—H3B60.9 (4)
C5—N3—C6—C40.09 (7)H2—C2—C3—H3B58.7 (5)
O2—C1—C2—N1155.03 (4)H3B—C3—C4—N2172.1 (4)
C1—C2—C3—C4179.00 (5)C3—C4—C6—H61.4 (6)
N2—C4—C6—N30.09 (6)N1—C2—C3—H3B177.8 (4)
H1A—N1—C2—C342.3 (5)H2—C2—C3—C461.4 (4)
H1B—N1—C2—C377.1 (5)H3A—C3—C4—N266.7 (4)
H1C—N1—C2—C3162.3 (5)H3B—C3—C4—C69.5 (4)
C6—N3—C5—H5178.2 (5)C1—C2—C3—H3A56.0 (4)
C5—N3—C6—H6179.9 (5)H2—C2—C3—H3A175.6 (6)
O1—C1—C2—H2145.6 (4)H3A—C3—C4—C6111.7 (5)
C4—N2—C5—N30.31 (6)N2—C4—C6—H6179.9 (6)
(HMTX19) top
Crystal data top
C6H9N3O2F(000) = 164.036
Mr = 155.16Dx = 1.455 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 5.1656 (2) ÅCell parameters from 2706 reflections
b = 7.2761 (3) Åθ = 3.5–30.4°
c = 9.4978 (3) ŵ = 0.11 mm1
β = 97.316 (3)°T = 105 K
V = 354.07 (2) Å3Plate, colourless
Z = 20.2 × 0.2 × 0.1 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2148 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics2032 reflections with I 2u(I)
Multilayer optics monochromatorRint = 0.033
φ scansθmax = 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 = 77
Tmin = 0.650, Tmax = 0.746k = 1010
11193 measured reflectionsl = 1313
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.022 w = 1/[σ2(Fo2) + (0.0076P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.032(Δ/σ)max = 0.0001
S = 1.18Δρmax = 0.15 e Å3
2148 reflectionsΔρmin = 0.12 e Å3
181 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
100 restraintsAbsolute structure parameter: 0.3 (11)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O20.31462 (8)0.45104 (7)1.01449 (4)0.01453 (10)
O10.73996 (8)0.44614 (8)1.09888 (4)0.01520 (11)
N10.87419 (11)0.63417 (8)0.87357 (6)0.01094 (12)
H1A0.9415 (19)0.6410 (15)0.7770 (10)0.027 (3)
H1B1.0108 (19)0.5709 (14)0.9431 (9)0.023 (2)
H1C0.8448 (18)0.7607 (15)0.9100 (10)0.022 (2)
N30.72092 (10)0.44401 (10)0.38769 (5)0.01304 (12)
H30.6849 (15)0.4344 (15)0.2827 (8)0.021 (2)
N20.92139 (11)0.51550 (8)0.60132 (5)0.01285 (13)
C10.55305 (12)0.47409 (9)1.00405 (6)0.00975 (14)
C40.69926 (12)0.41379 (9)0.61629 (6)0.01066 (15)
C60.57349 (13)0.36888 (10)0.48424 (6)0.01262 (14)
H60.3984 (17)0.2938 (14)0.4523 (8)0.032 (3)
C20.61967 (12)0.53500 (10)0.85723 (6)0.00947 (13)
H20.4685 (14)0.6303 (12)0.8112 (7)0.019 (2)
C50.92565 (13)0.53046 (10)0.46240 (6)0.01370 (14)
H51.0726 (17)0.6058 (13)0.4133 (8)0.035 (3)
C30.63061 (14)0.36558 (10)0.76089 (6)0.01275 (14)
H3A0.7714 (17)0.2688 (12)0.8157 (9)0.027 (2)
H3B0.4403 (17)0.3002 (13)0.7510 (9)0.030 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0113 (2)0.0168 (3)0.01614 (19)0.0001 (2)0.00433 (16)0.0054 (2)
O10.0128 (2)0.0240 (3)0.00897 (17)0.0002 (2)0.00203 (16)0.0036 (2)
N10.0123 (3)0.0110 (4)0.0096 (2)0.0018 (3)0.0015 (2)0.0007 (2)
H1A0.037 (6)0.025 (6)0.021 (3)0.010 (4)0.0118 (19)0.007 (2)
H1B0.017 (5)0.021 (6)0.028 (4)0.002 (3)0.007 (2)0.008 (2)
H1C0.025 (6)0.014 (4)0.026 (5)0.000 (2)0.005 (3)0.004 (2)
N30.0166 (3)0.0145 (3)0.0082 (2)0.0005 (3)0.00208 (18)0.0005 (2)
H30.026 (5)0.028 (6)0.009 (3)0.002 (4)0.0024 (16)0.0003 (17)
N20.0140 (3)0.0145 (3)0.0101 (2)0.0036 (2)0.00176 (19)0.0010 (2)
C10.0108 (3)0.0097 (4)0.0091 (2)0.0004 (3)0.0030 (2)0.0003 (2)
C40.0139 (3)0.0101 (4)0.0083 (2)0.0012 (3)0.0028 (2)0.0002 (2)
C60.0144 (3)0.0135 (4)0.0099 (3)0.0014 (3)0.0012 (2)0.0015 (2)
H60.026 (4)0.043 (6)0.027 (5)0.017 (3)0.002 (2)0.004 (3)
C20.0102 (3)0.0108 (4)0.0077 (2)0.0000 (3)0.0022 (2)0.0008 (2)
H20.019 (4)0.008 (4)0.028 (5)0.005 (2)0.005 (3)0.007 (3)
C50.0155 (3)0.0155 (4)0.0108 (3)0.0008 (3)0.0043 (2)0.0010 (3)
H50.038 (5)0.043 (7)0.028 (5)0.016 (3)0.014 (2)0.005 (3)
C30.0186 (4)0.0103 (4)0.0099 (3)0.0034 (3)0.0038 (2)0.0003 (2)
H3A0.042 (5)0.019 (5)0.019 (5)0.008 (2)0.002 (3)0.002 (3)
H3B0.027 (4)0.031 (5)0.032 (5)0.014 (2)0.007 (2)0.003 (3)
Geometric parameters (Å, º) top
O2—C11.2594 (7)N2—C51.3270 (7)
O1—C11.2503 (7)C1—C21.5432 (8)
N1—H1A1.022 (9)C4—C61.3763 (8)
N1—H1B1.014 (9)C4—C31.5030 (8)
N1—H1C1.002 (11)C6—H61.067 (8)
N1—C21.4904 (8)C2—H21.093 (8)
N3—H30.994 (7)C2—C31.5405 (9)
N3—C61.3775 (8)C5—H51.089 (8)
N3—C51.3515 (9)C3—H3A1.095 (8)
N2—C41.3878 (8)C3—H3B1.085 (9)
H1B—N1—H1A108.5 (8)H6—C6—N3122.3 (5)
H1C—N1—H1A110.4 (8)H6—C6—C4131.7 (5)
H1C—N1—H1B108.4 (7)C1—C2—N1109.89 (5)
C2—N1—H1A109.1 (6)H2—C2—N1108.1 (5)
C2—N1—H1B112.3 (6)H2—C2—C1108.3 (4)
C2—N1—H1C108.1 (5)C3—C2—N1110.53 (5)
C6—N3—H3126.3 (5)C3—C2—C1109.64 (6)
C5—N3—H3126.4 (5)C3—C2—H2110.4 (4)
C5—N3—C6107.29 (5)N2—C5—N3111.89 (6)
C5—N2—C4105.32 (5)H5—C5—N3123.5 (4)
O1—C1—O2126.50 (5)H5—C5—N2124.6 (4)
C2—C1—O2116.25 (5)C2—C3—C4112.75 (6)
C2—C1—O1117.20 (5)H3A—C3—C4111.4 (5)
C6—C4—N2109.50 (5)H3A—C3—C2107.7 (4)
C3—C4—N2120.82 (5)H3B—C3—C4109.8 (4)
C3—C4—C6129.67 (6)H3B—C3—C2107.5 (5)
C4—C6—N3105.99 (6)H3B—C3—H3A107.4 (7)
C5—N2—C4—C3179.01 (6)O1—C1—C2—N127.52 (8)
C6—N3—C5—N20.32 (8)O2—C1—C2—C383.32 (7)
O1—C1—C2—C394.16 (7)C2—C3—C4—N253.53 (8)
N1—C2—C3—C457.73 (7)C3—C4—C6—N3178.69 (7)
C2—C3—C4—C6127.85 (7)H1A—N1—C2—H278.2 (7)
H1A—N1—C2—C1163.8 (6)H1B—N1—C2—H2161.4 (7)
H1B—N1—C2—C143.5 (6)H1C—N1—C2—H241.9 (7)
H1C—N1—C2—C176.1 (6)H3—N3—C5—N2178.7 (7)
C4—N2—C5—H5178.3 (6)H3—N3—C6—C4178.8 (7)
H3—N3—C5—H52.7 (9)O2—C1—C2—H237.2 (5)
H3—N3—C6—H61.6 (10)N1—C2—C3—H3A65.6 (5)
C5—N2—C4—C60.14 (8)C1—C2—C3—H3B59.8 (5)
C5—N3—C6—C40.22 (8)H2—C2—C3—H3B59.5 (6)
O2—C1—C2—N1155.01 (6)H3B—C3—C4—N2173.4 (5)
C1—C2—C3—C4179.02 (5)C3—C4—C6—H61.8 (7)
N2—C4—C6—N30.06 (7)N1—C2—C3—H3B179.0 (5)
H1A—N1—C2—C342.7 (6)H2—C2—C3—C461.8 (4)
H1B—N1—C2—C377.7 (6)H3A—C3—C4—N267.7 (5)
H1C—N1—C2—C3162.8 (6)H3B—C3—C4—C68.0 (5)
C6—N3—C5—H5178.3 (6)C1—C2—C3—H3A55.7 (5)
C5—N3—C6—H6179.4 (6)H2—C2—C3—H3A174.9 (6)
O1—C1—C2—H2145.4 (4)H3A—C3—C4—C6110.9 (5)
C4—N2—C5—N30.28 (8)N2—C4—C6—H6179.5 (7)
(HMTX20) top
Crystal data top
C6H9N3O2F(000) = 164.037
Mr = 155.16Dx = 1.428 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 5.1854 (8) ÅCell parameters from 2412 reflections
b = 7.3998 (10) Åθ = 3.5–30.2°
c = 9.4976 (12) ŵ = 0.11 mm1
β = 98.182 (10)°T = 295 K
V = 360.72 (9) Å3Plate, colourless
Z = 20.2 × 0.2 × 0.1 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1806 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics1683 reflections with I 2u(I)
Multilayer optics monochromatorRint = 0.024
φ scansθmax = 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 = 65
Tmin = 0.689, Tmax = 0.746k = 1010
11356 measured reflectionsl = 1313
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025 w = 1/[σ2(Fo2) + (0.0158P)2 + 0.0067P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.049(Δ/σ)max = 0.001
S = 1.35Δρmax = 0.10 e Å3
1806 reflectionsΔρmin = 0.10 e Å3
181 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
1 restraintAbsolute structure parameter: 1.0 (15)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O20.31397 (17)0.44525 (12)1.01027 (8)0.0366 (2)
O10.73608 (15)0.44348 (13)1.09800 (7)0.0393 (2)
N10.8687 (2)0.63339 (13)0.87608 (10)0.0249 (2)
H1A0.934 (3)0.642 (2)0.7802 (17)0.041 (4)
H1B0.997 (3)0.568 (2)0.9444 (18)0.047 (5)
H1C0.837 (3)0.755 (2)0.9137 (17)0.043 (5)
N30.72208 (19)0.44672 (15)0.38771 (8)0.0321 (2)
H30.690 (3)0.429 (3)0.2813 (15)0.052 (5)
N20.9189 (2)0.51988 (13)0.60207 (8)0.0317 (2)
C10.5502 (2)0.47060 (14)1.00185 (9)0.0237 (2)
C40.7011 (2)0.41693 (13)0.61567 (9)0.0257 (3)
C60.5775 (3)0.37123 (15)0.48334 (10)0.0314 (3)
H60.406 (3)0.292 (3)0.4481 (15)0.065 (5)
C20.6172 (2)0.53295 (14)0.85629 (9)0.0215 (2)
H20.465 (2)0.6270 (19)0.8093 (12)0.032 (4)
C50.9232 (3)0.53403 (17)0.46361 (10)0.0338 (3)
H51.071 (4)0.608 (3)0.4137 (14)0.066 (5)
C30.6341 (3)0.36806 (14)0.75968 (10)0.0298 (3)
H3A0.774 (4)0.275 (2)0.8164 (17)0.069 (6)
H3B0.447 (4)0.298 (3)0.7443 (17)0.075 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0264 (5)0.0449 (5)0.0406 (4)0.0005 (4)0.0121 (3)0.0173 (4)
O10.0312 (5)0.0676 (5)0.0193 (3)0.0019 (5)0.0046 (3)0.0101 (4)
N10.0284 (6)0.0258 (5)0.0208 (4)0.0035 (4)0.0045 (4)0.0011 (4)
H1A0.040 (13)0.053 (12)0.034 (9)0.006 (9)0.016 (8)0.011 (9)
H1B0.031 (12)0.045 (11)0.060 (11)0.007 (9)0.017 (9)0.014 (9)
H1C0.054 (13)0.031 (10)0.048 (11)0.021 (9)0.017 (9)0.009 (8)
N30.0415 (6)0.0374 (5)0.0179 (3)0.0017 (5)0.0061 (3)0.0004 (4)
H30.094 (14)0.046 (11)0.017 (7)0.015 (12)0.008 (8)0.013 (8)
N20.0340 (6)0.0397 (5)0.0222 (4)0.0090 (4)0.0063 (4)0.0016 (4)
C10.0257 (7)0.0271 (5)0.0192 (4)0.0027 (4)0.0069 (4)0.0027 (3)
C40.0348 (7)0.0253 (5)0.0178 (4)0.0035 (4)0.0067 (4)0.0015 (3)
C60.0399 (9)0.0337 (6)0.0205 (4)0.0049 (5)0.0040 (5)0.0044 (4)
H60.073 (13)0.080 (13)0.037 (10)0.032 (11)0.011 (8)0.008 (9)
C20.0233 (6)0.0246 (4)0.0169 (4)0.0001 (4)0.0043 (4)0.0026 (3)
H20.024 (8)0.028 (8)0.043 (8)0.006 (6)0.002 (6)0.024 (7)
C50.0388 (9)0.0416 (6)0.0235 (5)0.0042 (6)0.0129 (5)0.0023 (4)
H50.078 (14)0.090 (16)0.036 (9)0.008 (12)0.028 (8)0.006 (10)
C30.0463 (9)0.0243 (5)0.0200 (4)0.0084 (5)0.0088 (4)0.0014 (4)
H3A0.127 (19)0.041 (11)0.041 (10)0.026 (12)0.020 (11)0.015 (8)
H3B0.080 (16)0.098 (15)0.048 (11)0.066 (13)0.015 (9)0.011 (11)
Geometric parameters (Å, º) top
O2—C11.2529 (14)N2—C51.3224 (13)
O1—C11.2461 (12)C1—C21.5433 (13)
N1—H1A1.018 (16)C4—C61.3695 (13)
N1—H1B0.988 (16)C4—C31.5026 (13)
N1—H1C0.988 (16)C6—H61.076 (16)
N1—C21.4896 (14)C2—H21.098 (12)
N3—H31.010 (14)C2—C31.5366 (14)
N3—C61.3759 (15)C5—H51.103 (18)
N3—C51.3455 (16)C3—H3A1.089 (17)
N2—C41.3833 (14)C3—H3B1.090 (17)
H1B—N1—H1A110.0 (14)H6—C6—N3121.2 (8)
H1C—N1—H1A110.9 (14)H6—C6—C4132.7 (8)
H1C—N1—H1B109.8 (13)C1—C2—N1109.93 (8)
C2—N1—H1A108.4 (9)H2—C2—N1107.5 (7)
C2—N1—H1B109.5 (10)H2—C2—C1108.3 (7)
C2—N1—H1C108.1 (10)C3—C2—N1110.38 (9)
C6—N3—H3125.5 (11)C3—C2—C1109.68 (8)
C5—N3—H3127.1 (11)C3—C2—H2111.0 (7)
C5—N3—C6107.15 (9)N2—C5—N3111.92 (11)
C5—N2—C4105.42 (9)H5—C5—N3122.8 (8)
O1—C1—O2126.19 (10)H5—C5—N2125.3 (8)
C2—C1—O2116.66 (8)C2—C3—C4113.12 (8)
C2—C1—O1117.08 (11)H3A—C3—C4112.2 (10)
C6—C4—N2109.39 (9)H3A—C3—C2107.4 (9)
C3—C4—N2121.02 (9)H3B—C3—C4108.0 (8)
C3—C4—C6129.58 (11)H3B—C3—C2109.3 (11)
C4—C6—N3106.12 (11)H3B—C3—H3A106.5 (17)
C5—N2—C4—C3178.65 (10)O1—C1—C2—N127.95 (13)
C6—N3—C5—N20.12 (15)O2—C1—C2—C383.69 (12)
O1—C1—C2—C393.59 (12)C2—C3—C4—N253.66 (15)
N1—C2—C3—C458.25 (13)C3—C4—C6—N3178.44 (11)
C2—C3—C4—C6127.85 (13)H1A—N1—C2—H278.1 (11)
H1A—N1—C2—C1164.3 (9)H1B—N1—C2—H2162.1 (12)
H1B—N1—C2—C144.4 (10)H1C—N1—C2—H242.4 (12)
H1C—N1—C2—C175.2 (10)H3—N3—C5—N2174.7 (15)
C4—N2—C5—H5179.8 (14)H3—N3—C6—C4174.7 (14)
H3—N3—C5—H56 (2)O2—C1—C2—H237.6 (7)
H3—N3—C6—H64.2 (19)N1—C2—C3—H3A66.2 (11)
C5—N2—C4—C60.12 (13)C1—C2—C3—H3B60.1 (10)
C5—N3—C6—C40.19 (14)H2—C2—C3—H3B59.5 (12)
O2—C1—C2—N1154.78 (9)H3B—C3—C4—N2174.9 (12)
C1—C2—C3—C4179.51 (10)C3—C4—C6—H60.3 (15)
N2—C4—C6—N30.19 (13)N1—C2—C3—H3B178.7 (10)
H1A—N1—C2—C343.2 (9)H2—C2—C3—C460.9 (7)
H1B—N1—C2—C376.7 (10)H3A—C3—C4—N268.0 (10)
H1C—N1—C2—C3163.7 (10)H3B—C3—C4—C66.6 (12)
C6—N3—C5—H5179.7 (13)C1—C2—C3—H3A55.1 (11)
C5—N3—C6—H6179.1 (13)H2—C2—C3—H3A174.7 (12)
O1—C1—C2—H2145.1 (7)H3A—C3—C4—C6110.5 (10)
C4—N2—C5—N30.00 (14)N2—C4—C6—H6179.0 (15)
(HOTX21) top
Crystal data top
C6H9N3O2Dx = 1.477 Mg m3
Mr = 155.16Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 7499 reflections
a = 5.1498 (2) Åθ = 3.0–36.3°
b = 7.1902 (2) ŵ = 0.11 mm1
c = 18.8503 (6) ÅT = 5 K
V = 697.99 (4) Å3Needle, colourless
Z = 40.2 × 0.1 × 0.1 mm
F(000) = 328.072
Data collection top
Bruker APEX-II CCD
diffractometer
2928 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics2768 reflections with I 2u(I)
Multilayer optics monochromatorRint = 0.027
φ scansθmax = 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 = 88
Tmin = 0.682, Tmax = 0.747k = 1010
13716 measured reflectionsl = 2828
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.019 w = 1/[σ2(Fo2) + (0.010P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.032(Δ/σ)max = 0.0001
S = 1.13Δρmax = 0.17 e Å3
2928 reflectionsΔρmin = 0.13 e Å3
181 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
99 restraintsAbsolute structure parameter: 0.1 (7)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O20.32523 (5)0.49519 (5)0.239747 (17)0.00711 (7)
O10.73277 (5)0.49178 (6)0.197479 (17)0.00746 (7)
N10.91743 (7)0.31183 (6)0.31202 (2)0.00606 (7)
N30.86938 (6)0.50331 (6)0.55327 (2)0.00651 (7)
N21.03202 (6)0.43924 (6)0.44704 (2)0.00638 (7)
C40.80291 (7)0.53935 (6)0.43875 (2)0.00539 (8)
C10.56621 (7)0.47000 (7)0.24536 (2)0.00510 (8)
C20.66640 (7)0.41387 (7)0.31927 (2)0.00504 (8)
C60.70071 (8)0.57917 (7)0.50444 (2)0.00626 (8)
C51.06292 (8)0.42054 (7)0.51647 (2)0.00661 (8)
C30.70255 (8)0.58731 (7)0.36630 (2)0.00640 (8)
H1B1.0360 (14)0.3760 (12)0.2769 (4)0.0172 (19)
H1C0.8753 (15)0.1814 (12)0.2959 (4)0.0205 (19)
H1A1.0081 (14)0.3117 (11)0.3601 (4)0.0172 (19)
H30.8465 (14)0.5059 (12)0.6068 (4)0.0173 (19)
H20.5256 (12)0.3202 (10)0.3429 (4)0.0172 (17)
H60.5315 (13)0.6553 (10)0.5190 (4)0.0217 (18)
H51.2182 (12)0.3487 (10)0.5412 (3)0.0208 (18)
H3A0.8308 (14)0.6852 (11)0.3389 (4)0.0203 (18)
H3B0.5223 (14)0.6553 (10)0.3706 (4)0.0243 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.00482 (10)0.00938 (18)0.00712 (15)0.00064 (13)0.00049 (10)0.00189 (12)
O10.00583 (10)0.01196 (18)0.00459 (15)0.00016 (12)0.00017 (10)0.00142 (12)
N10.00558 (13)0.0068 (2)0.00580 (19)0.00100 (14)0.00005 (13)0.00024 (14)
N30.00740 (12)0.0082 (2)0.00394 (18)0.00061 (14)0.00015 (11)0.00013 (14)
N20.00622 (11)0.0083 (2)0.00463 (19)0.00177 (12)0.00029 (12)0.00033 (13)
C40.00607 (12)0.0060 (2)0.0041 (2)0.00091 (14)0.00079 (13)0.00002 (14)
C10.00472 (13)0.0058 (2)0.0047 (2)0.00020 (14)0.00039 (14)0.00005 (14)
C20.00474 (13)0.0061 (2)0.0043 (2)0.00002 (15)0.00034 (13)0.00045 (15)
C60.00628 (14)0.0077 (2)0.0048 (2)0.00128 (15)0.00000 (13)0.00053 (15)
C50.00626 (14)0.0082 (2)0.0054 (2)0.00135 (16)0.00092 (14)0.00041 (15)
C30.00775 (14)0.0061 (2)0.0053 (2)0.00107 (16)0.00100 (14)0.00034 (15)
H1B0.006 (3)0.021 (5)0.024 (4)0.009 (2)0.007 (2)0.012 (2)
H1C0.027 (4)0.013 (3)0.022 (4)0.0043 (19)0.003 (3)0.0055 (19)
H1A0.015 (4)0.020 (5)0.016 (3)0.003 (3)0.0060 (17)0.0018 (19)
H30.033 (4)0.015 (5)0.004 (3)0.011 (4)0.0007 (16)0.0018 (17)
H20.014 (3)0.011 (4)0.027 (4)0.002 (2)0.002 (2)0.007 (2)
H60.018 (3)0.025 (5)0.022 (4)0.008 (2)0.005 (2)0.002 (3)
H50.019 (3)0.027 (5)0.017 (4)0.008 (2)0.002 (2)0.004 (2)
H3A0.023 (3)0.022 (4)0.016 (4)0.007 (2)0.000 (2)0.001 (2)
H3B0.022 (3)0.021 (4)0.030 (5)0.0085 (18)0.002 (2)0.000 (3)
Geometric parameters (Å, º) top
O2—C11.2586 (5)N2—C51.3252 (6)
O1—C11.2550 (5)C4—C61.3755 (6)
N1—H1B1.012 (8)C4—C31.5005 (6)
N1—H1A1.019 (8)C1—C21.5395 (6)
N1—H1C1.010 (9)C2—H21.085 (7)
N1—C21.4927 (5)C2—C31.5413 (7)
N3—H31.017 (8)C6—H61.065 (7)
N3—C61.3782 (6)C5—H51.060 (6)
N3—C51.3524 (6)C3—H3B1.052 (7)
N2—C41.3909 (5)C3—H3A1.095 (7)
H1A—N1—H1B107.8 (6)H2—C2—N1108.1 (4)
H1C—N1—H1B110.8 (7)H2—C2—C1108.0 (4)
H1C—N1—H1A111.5 (7)C3—C2—N1110.23 (3)
C2—N1—H1B111.0 (4)C3—C2—C1110.42 (4)
C2—N1—H1A108.4 (4)C3—C2—H2110.3 (4)
C2—N1—H1C107.3 (5)C4—C6—N3106.12 (4)
C6—N3—H3125.7 (4)H6—C6—N3123.2 (4)
C5—N3—H3127.1 (4)H6—C6—C4130.7 (4)
C5—N3—C6107.22 (4)N2—C5—N3111.93 (4)
C5—N2—C4105.39 (4)H5—C5—N3123.0 (4)
C6—C4—N2109.34 (4)H5—C5—N2125.1 (4)
C3—C4—N2120.89 (4)C2—C3—C4112.28 (4)
C3—C4—C6129.77 (4)H3B—C3—C4109.9 (4)
O1—C1—O2126.55 (4)H3B—C3—C2108.3 (4)
C2—C1—O2116.38 (4)H3A—C3—C4111.7 (4)
C2—C1—O1117.03 (3)H3A—C3—C2108.7 (4)
C1—C2—N1109.65 (4)H3A—C3—H3B105.6 (6)
C5—N2—C4—C3179.69 (4)O1—C1—C2—N126.72 (6)
C6—N3—C5—N20.58 (5)O2—C1—C2—C382.89 (5)
O1—C1—C2—C394.92 (5)C2—C3—C4—N255.80 (5)
N1—C2—C3—C458.08 (4)C3—C4—C6—N3179.98 (7)
C2—C3—C4—C6123.97 (5)H1A—N1—C2—H279.9 (6)
H1A—N1—C2—C1162.5 (5)H1B—N1—C2—H2161.9 (6)
H1B—N1—C2—C144.3 (5)H1C—N1—C2—H240.5 (6)
H1C—N1—C2—C177.1 (5)H3—N3—C5—N2178.4 (6)
C4—N2—C5—H5179.0 (5)H3—N3—C6—C4178.4 (6)
H3—N3—C5—H51.0 (7)O2—C1—C2—H237.8 (4)
H3—N3—C6—H63.3 (7)N1—C2—C3—H3A66.0 (4)
C5—N2—C4—C60.12 (5)C1—C2—C3—H3B59.1 (4)
C5—N3—C6—C40.47 (5)H2—C2—C3—H3B60.3 (6)
O2—C1—C2—N1155.47 (4)H3B—C3—C4—N2176.4 (4)
C1—C2—C3—C4179.38 (3)C3—C4—C6—H61.8 (5)
N2—C4—C6—N30.22 (5)N1—C2—C3—H3B179.6 (4)
H1A—N1—C2—C340.7 (5)H2—C2—C3—C461.2 (4)
H1B—N1—C2—C377.5 (5)H3A—C3—C4—N266.7 (4)
H1C—N1—C2—C3161.2 (5)H3B—C3—C4—C63.4 (4)
C6—N3—C5—H5178.8 (4)C1—C2—C3—H3A55.3 (4)
C5—N3—C6—H6178.8 (5)H2—C2—C3—H3A174.6 (6)
O1—C1—C2—H2144.4 (4)H3A—C3—C4—C6113.6 (4)
C4—N2—C5—N30.43 (5)N2—C4—C6—H6178.4 (5)
(HOTX22) top
Crystal data top
C6H9N3O2Dx = 1.470 Mg m3
Mr = 155.16Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 6123 reflections
a = 5.1521 (1) Åθ = 3.0–36.0°
b = 7.2228 (2) ŵ = 0.11 mm1
c = 18.8440 (6) ÅT = 105 K
V = 701.23 (3) Å3Needle, colourless
Z = 40.2 × 0.1 × 0.1 mm
F(000) = 328.072
Data collection top
Bruker APEX-II CCD
diffractometer
2942 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics2706 reflections with I 2u(I)
Multilayer optics monochromatorRint = 0.030
φ scansθmax = 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 = 88
Tmin = 0.687, Tmax = 0.747k = 1010
13793 measured reflectionsl = 2828
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.023 w = 1/[σ2(Fo2) + (0.0119P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.038(Δ/σ)max = 0.0001
S = 1.12Δρmax = 0.17 e Å3
2942 reflectionsΔρmin = 0.15 e Å3
181 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
99 restraintsAbsolute structure parameter: 0.4 (8)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O20.32475 (6)0.49818 (6)0.240209 (19)0.01318 (8)
O10.73091 (6)0.49455 (7)0.197629 (19)0.01394 (8)
N10.91616 (8)0.31391 (7)0.31181 (3)0.00998 (9)
H1B1.0343 (15)0.3750 (13)0.2770 (4)0.020 (2)
H1A1.0073 (14)0.3128 (12)0.3597 (5)0.0157 (19)
H1C0.8725 (17)0.1843 (14)0.2953 (5)0.023 (2)
N30.87041 (7)0.50257 (7)0.55335 (3)0.01189 (9)
H30.8494 (16)0.5062 (13)0.6068 (5)0.026 (2)
N21.03224 (8)0.43944 (7)0.44706 (2)0.01190 (9)
C40.80387 (9)0.53942 (7)0.43892 (3)0.00996 (9)
C10.56511 (8)0.47258 (8)0.24558 (3)0.00925 (9)
C20.66615 (8)0.41601 (8)0.31935 (3)0.00865 (9)
H20.5257 (14)0.3232 (11)0.3427 (4)0.0220 (19)
C60.70210 (9)0.57890 (9)0.50460 (3)0.01133 (10)
H60.5334 (15)0.6551 (11)0.5199 (4)0.028 (2)
C51.06326 (10)0.41995 (8)0.51647 (3)0.01233 (10)
H51.2175 (15)0.3476 (12)0.5415 (4)0.031 (2)
C30.70372 (10)0.58790 (9)0.36650 (3)0.01170 (10)
H3B0.5230 (16)0.6543 (11)0.3711 (4)0.028 (2)
H3A0.8329 (16)0.6849 (12)0.3400 (4)0.027 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.00938 (12)0.0168 (2)0.01336 (19)0.00099 (16)0.00125 (12)0.00446 (16)
O10.01111 (13)0.0235 (2)0.00724 (18)0.00111 (15)0.00005 (12)0.00319 (16)
N10.01021 (15)0.0109 (3)0.0088 (2)0.00160 (17)0.00013 (15)0.00024 (16)
H1B0.009 (4)0.028 (5)0.022 (4)0.007 (2)0.003 (2)0.013 (2)
H1A0.013 (4)0.018 (5)0.016 (3)0.000 (3)0.0041 (17)0.0022 (19)
H1C0.030 (5)0.015 (4)0.025 (5)0.004 (2)0.002 (3)0.007 (2)
N30.01415 (15)0.0143 (2)0.0072 (2)0.00054 (17)0.00018 (14)0.00025 (17)
H30.045 (5)0.025 (6)0.007 (3)0.012 (4)0.0035 (17)0.0044 (17)
N20.01215 (15)0.0153 (3)0.0083 (2)0.00333 (16)0.00046 (15)0.00037 (16)
C40.01187 (15)0.0103 (3)0.0077 (2)0.00147 (17)0.00122 (16)0.00048 (17)
C10.00919 (16)0.0107 (3)0.0079 (2)0.00063 (18)0.00100 (16)0.00048 (17)
C20.00877 (16)0.0101 (3)0.0071 (2)0.00003 (18)0.00033 (16)0.00073 (17)
H20.016 (3)0.014 (4)0.036 (5)0.001 (2)0.001 (3)0.008 (3)
C60.01237 (17)0.0129 (3)0.0087 (2)0.00133 (19)0.00016 (17)0.00168 (18)
H60.024 (3)0.031 (5)0.027 (5)0.009 (2)0.005 (2)0.003 (3)
C50.01257 (18)0.0156 (3)0.0088 (3)0.0011 (2)0.00196 (18)0.00093 (19)
H50.029 (4)0.040 (6)0.026 (4)0.014 (2)0.004 (2)0.003 (3)
C30.01547 (19)0.0104 (3)0.0093 (3)0.0027 (2)0.00243 (18)0.00081 (19)
H3B0.029 (3)0.023 (5)0.033 (5)0.0109 (19)0.005 (2)0.002 (3)
H3A0.034 (4)0.022 (4)0.025 (4)0.007 (2)0.004 (3)0.001 (2)
Geometric parameters (Å, º) top
O2—C11.2562 (5)N2—C51.3253 (7)
O1—C11.2535 (6)C4—C61.3739 (7)
N1—H1B0.997 (8)C4—C31.5005 (7)
N1—H1A1.018 (8)C1—C21.5396 (7)
N1—H1C1.012 (9)C2—H21.080 (8)
N1—C21.4910 (6)C2—C31.5389 (8)
N3—H31.013 (9)C6—H61.069 (7)
N3—C61.3784 (7)C5—H51.061 (7)
N3—C51.3513 (7)C3—H3B1.051 (8)
N2—C41.3890 (6)C3—H3A1.088 (8)
H1A—N1—H1B107.7 (7)H2—C2—N1108.1 (4)
H1C—N1—H1B110.0 (7)H2—C2—C1107.8 (4)
H1C—N1—H1A111.6 (7)C3—C2—N1110.20 (4)
C2—N1—H1B111.8 (5)C3—C2—C1110.47 (5)
C2—N1—H1A108.5 (5)C3—C2—H2110.5 (5)
C2—N1—H1C107.2 (5)C4—C6—N3106.09 (4)
C6—N3—H3125.8 (5)H6—C6—N3122.5 (5)
C5—N3—H3127.0 (5)H6—C6—C4131.4 (5)
C5—N3—C6107.25 (5)N2—C5—N3111.84 (5)
C5—N2—C4105.44 (4)H5—C5—N3122.7 (4)
C6—C4—N2109.38 (4)H5—C5—N2125.5 (4)
C3—C4—N2120.86 (4)C2—C3—C4112.34 (5)
C3—C4—C6129.76 (5)H3B—C3—C4109.6 (4)
O1—C1—O2126.52 (5)H3B—C3—C2107.7 (4)
C2—C1—O2116.43 (4)H3A—C3—C4110.9 (4)
C2—C1—O1117.00 (4)H3A—C3—C2109.4 (4)
C1—C2—N1109.71 (4)H3A—C3—H3B106.6 (6)
C5—N2—C4—C3179.64 (5)O1—C1—C2—N126.91 (7)
C6—N3—C5—N20.65 (7)O2—C1—C2—C382.89 (6)
O1—C1—C2—C394.78 (6)C2—C3—C4—N255.98 (6)
N1—C2—C3—C458.22 (6)C3—C4—C6—N3180.00 (7)
C2—C3—C4—C6123.88 (6)H1A—N1—C2—H280.0 (7)
H1A—N1—C2—C1162.6 (5)H1B—N1—C2—H2161.2 (7)
H1B—N1—C2—C143.9 (5)H1C—N1—C2—H240.6 (7)
H1C—N1—C2—C176.7 (6)H3—N3—C5—N2179.4 (6)
C4—N2—C5—H5178.7 (6)H3—N3—C6—C4179.3 (6)
H3—N3—C5—H50.1 (8)O2—C1—C2—H237.9 (4)
H3—N3—C6—H62.4 (8)N1—C2—C3—H3A65.4 (5)
C5—N2—C4—C60.25 (6)C1—C2—C3—H3B59.5 (4)
C5—N3—C6—C40.46 (6)H2—C2—C3—H3B59.7 (6)
O2—C1—C2—N1155.42 (5)H3B—C3—C4—N2175.7 (5)
C1—C2—C3—C4179.63 (4)C3—C4—C6—H61.8 (6)
N2—C4—C6—N30.13 (6)N1—C2—C3—H3B179.1 (4)
H1A—N1—C2—C340.8 (5)H2—C2—C3—C461.2 (4)
H1B—N1—C2—C377.9 (5)H3A—C3—C4—N266.8 (5)
H1C—N1—C2—C3161.4 (6)H3B—C3—C4—C64.1 (5)
C6—N3—C5—H5178.7 (5)C1—C2—C3—H3A56.0 (5)
C5—N3—C6—H6178.8 (5)H2—C2—C3—H3A175.2 (6)
O1—C1—C2—H2144.4 (4)H3A—C3—C4—C6113.4 (5)
C4—N2—C5—N30.56 (6)N2—C4—C6—H6178.3 (6)
(HOTX23) top
Crystal data top
C6H9N3O2Dx = 1.442 Mg m3
Mr = 155.16Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4787 reflections
a = 5.1690 (3) Åθ = 3.0–32.3°
b = 7.3430 (5) ŵ = 0.11 mm1
c = 18.8317 (13) ÅT = 295 K
V = 714.78 (8) Å3Needle, colourless
Z = 40.2 × 0.1 × 0.1 mm
F(000) = 328.073
Data collection top
Bruker APEX-II CCD
diffractometer
3008 independent reflections
Radiation source: rotating anode, Bruker TXS with Helios Optics2569 reflections with I 2u(I)
Multilayer optics monochromatorRint = 0.033
φ scansθmax = 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 = 88
Tmin = 0.648, Tmax = 0.747k = 1111
14091 measured reflectionsl = 2828
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.0206P)2 + 0.0062P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.054(Δ/σ)max = 0.001
S = 1.11Δρmax = 0.16 e Å3
3008 reflectionsΔρmin = 0.17 e Å3
181 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraintsAbsolute structure parameter: 0.1 (11)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O20.32399 (8)0.50882 (8)0.24194 (3)0.03363 (13)
O10.72486 (9)0.50473 (10)0.19836 (3)0.03629 (14)
N10.91181 (11)0.32105 (9)0.31064 (3)0.02296 (11)
H1B1.031 (2)0.3861 (17)0.2767 (6)0.043 (3)
H1C0.867 (2)0.1949 (15)0.2945 (6)0.037 (3)
H1A1.0053 (18)0.3154 (16)0.3575 (6)0.032 (2)
N30.87440 (11)0.49977 (9)0.55355 (3)0.02985 (13)
H30.852 (3)0.5006 (17)0.6066 (7)0.049 (3)
N21.03303 (11)0.43961 (9)0.44716 (3)0.02938 (13)
C40.80827 (12)0.54010 (9)0.43947 (3)0.02360 (12)
C10.56258 (10)0.48232 (9)0.24645 (3)0.02192 (12)
C20.66536 (10)0.42348 (9)0.31972 (3)0.01979 (11)
H20.5262 (18)0.3325 (13)0.3427 (6)0.036 (2)
C60.70825 (14)0.57763 (11)0.50522 (4)0.02829 (14)
H60.546 (2)0.6534 (18)0.5216 (6)0.061 (4)
C51.06397 (14)0.41825 (12)0.51634 (4)0.03111 (15)
H51.213 (2)0.3449 (19)0.5411 (5)0.062 (4)
C30.70836 (15)0.59061 (11)0.36742 (4)0.02776 (14)
H3A0.835 (3)0.6820 (17)0.3409 (6)0.052 (3)
H3B0.526 (2)0.6577 (17)0.3719 (6)0.063 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.02204 (18)0.0425 (3)0.0363 (3)0.0018 (2)0.00462 (18)0.0138 (2)
O10.02826 (19)0.0626 (4)0.0180 (2)0.0029 (2)0.00110 (17)0.0095 (2)
N10.0238 (2)0.0253 (3)0.0198 (3)0.0040 (2)0.0001 (2)0.0005 (2)
H1B0.032 (6)0.053 (9)0.043 (8)0.008 (6)0.018 (5)0.025 (6)
H1C0.044 (6)0.014 (6)0.052 (7)0.003 (5)0.000 (6)0.016 (6)
H1A0.026 (5)0.048 (7)0.022 (6)0.010 (5)0.001 (4)0.003 (5)
N30.0367 (2)0.0362 (4)0.0167 (3)0.0030 (3)0.0005 (2)0.0013 (2)
H30.078 (9)0.042 (9)0.027 (7)0.008 (9)0.000 (6)0.003 (6)
N20.0302 (2)0.0383 (3)0.0196 (3)0.0079 (2)0.0014 (2)0.0004 (2)
C40.0286 (2)0.0247 (3)0.0174 (3)0.0025 (2)0.0027 (2)0.0020 (2)
C10.0212 (2)0.0259 (3)0.0187 (3)0.0020 (2)0.0036 (2)0.0028 (2)
C20.0206 (2)0.0226 (3)0.0162 (3)0.0004 (2)0.00109 (19)0.0021 (2)
H20.032 (5)0.021 (5)0.054 (7)0.011 (5)0.002 (5)0.013 (5)
C60.0306 (3)0.0329 (4)0.0214 (3)0.0028 (3)0.0008 (2)0.0057 (3)
H60.055 (7)0.072 (9)0.057 (8)0.022 (7)0.010 (6)0.020 (7)
C50.0324 (3)0.0401 (4)0.0208 (3)0.0042 (3)0.0057 (3)0.0021 (3)
H50.056 (6)0.096 (10)0.035 (7)0.030 (7)0.001 (6)0.016 (7)
C30.0385 (3)0.0239 (4)0.0209 (3)0.0073 (3)0.0050 (3)0.0014 (3)
H3A0.079 (8)0.041 (7)0.035 (6)0.018 (8)0.006 (6)0.007 (6)
H3B0.066 (8)0.072 (9)0.051 (8)0.049 (7)0.022 (6)0.016 (7)
Geometric parameters (Å, º) top
O1—C11.2453 (8)C3—H3A1.062 (14)
N2—C51.3219 (9)N1—C21.4892 (8)
C2—C31.5370 (10)N3—C61.3758 (10)
N1—H1A1.007 (11)C4—C61.3698 (10)
C2—H21.073 (10)N1—H1C1.002 (11)
C6—H61.053 (11)C3—H3B1.067 (11)
O2—C11.2514 (7)N2—C41.3839 (9)
N3—C51.3452 (10)C1—C21.5404 (8)
C3—C41.4984 (10)N3—H31.006 (13)
N1—H1B1.008 (11)C5—H51.049 (11)
C4—N2—C5105.54 (6)C2—N1—H1B110.9 (7)
O1—C1—C2117.14 (5)H1A—N1—H1C109.8 (9)
N1—C2—C3110.28 (5)C6—N3—H3125.6 (8)
N2—C4—C3121.07 (6)C3—C2—H2111.0 (6)
N2—C5—N3111.87 (7)C4—C3—H3A111.7 (7)
C2—N1—H1A109.3 (6)N2—C5—H5126.0 (5)
H1A—N1—H1B106.4 (9)C4—C6—H6132.2 (6)
C5—N3—H3127.2 (8)O1—C1—O2126.44 (6)
C1—C2—H2107.7 (6)N1—C2—C1109.50 (5)
C2—C3—H3B106.7 (6)C2—C3—C4112.42 (6)
H3A—C3—H3B106.9 (10)C3—C4—C6129.69 (6)
N3—C6—H6121.5 (6)C2—N1—H1C107.7 (6)
C5—N3—C6107.16 (6)H1B—N1—H1C112.8 (9)
O2—C1—C2116.38 (5)N1—C2—H2107.8 (5)
C1—C2—C3110.45 (5)C2—C3—H3A108.6 (6)
N2—C4—C6109.24 (6)C4—C3—H3B110.3 (6)
N3—C6—C4106.19 (6)N3—C5—H5122.1 (5)
C5—N2—C4—C3179.52 (7)O1—C1—C2—N127.33 (8)
C6—N3—C5—N20.61 (9)O2—C1—C2—C383.35 (7)
O1—C1—C2—C394.31 (7)C2—C3—C4—N256.24 (8)
N1—C2—C3—C458.88 (7)C3—C4—C6—N3179.83 (7)
C2—C3—C4—C6123.32 (8)H1A—N1—C2—H279.9 (9)
H1A—N1—C2—C1163.2 (7)H1B—N1—C2—H2163.2 (9)
H1B—N1—C2—C146.3 (7)H1C—N1—C2—H239.4 (9)
H1C—N1—C2—C177.6 (7)H3—N3—C5—N2178.4 (10)
C4—N2—C5—H5178.1 (9)H3—N3—C6—C4178.3 (9)
H3—N3—C5—H50.2 (13)O2—C1—C2—H238.1 (6)
H3—N3—C6—H64.0 (12)N1—C2—C3—H3A65.2 (8)
C5—N2—C4—C60.12 (8)C1—C2—C3—H3B58.9 (7)
C5—N3—C6—C40.49 (8)H2—C2—C3—H3B60.6 (9)
O2—C1—C2—N1155.01 (6)H3B—C3—C4—N2175.2 (7)
C1—C2—C3—C4179.94 (5)C3—C4—C6—H62.9 (9)
N2—C4—C6—N30.23 (8)N1—C2—C3—H3B179.9 (7)
H1A—N1—C2—C341.5 (7)H2—C2—C3—C460.5 (6)
H1B—N1—C2—C375.5 (7)H3A—C3—C4—N266.1 (8)
H1C—N1—C2—C3160.7 (7)H3B—C3—C4—C64.4 (7)
C6—N3—C5—H5178.0 (8)C1—C2—C3—H3A56.0 (8)
C5—N3—C6—H6178.1 (8)H2—C2—C3—H3A175.4 (10)
O1—C1—C2—H2144.3 (6)H3A—C3—C4—C6114.3 (8)
C4—N2—C5—N30.45 (9)N2—C4—C6—H6177.5 (9)
 

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