A large anisotropic plasticity of l-leucinium hydrogen maleate preserved at cryogenic temperatures

Arkhipov, S.G.; Losev, E.A.; Nguyen, T.T.; Rychkov, D.A.; Boldyreva, E.V.

doi:10.1107/S2052520619000441

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A large anisotropic plasticity of L-leucinium hydrogen maleate preserved at cryogenic temperatures

S. G. Arkhipov, E. A. Losev, T. T. Nguyen, D. A. Rychkov and E. V. Boldyreva

L-Leucinium hydrogen maleate crystals are very plastic at ambient conditions. Here it is shown that this plasticity is preserved at least down to 77 K. The structural changes in the temperature range 293–100 K were followed in order to rationalize the large anisotropic plasticity in this compound. To the best of our knowledge, this is the first reported example of an organic compound remaining so plastic at cryogenic conditions.

Keywords: plastic crystals; low temperature; hydrogen bonds; intermolecular interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619000441/xk5052sup1.cif Contains datablocks l_leu_mal_100, l_leu_mal_125, l_leu_mal_150, l_leu_mal_175, l_leu_mal_200, l_leu_mal_225, l_leu_mal_250, l_leu_mal_275, l_leu_mal_293
	Moving Picture Experts Group (MP4) video file https://doi.org/10.1107/S2052520619000441/xk5052sup21.mp4 Video S1 of crystal of l-leucinium hydrogen maleate in liquid nitrogen
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_100sup2.hkl Contains datablock l_leu_mal_100
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_125sup3.hkl Contains datablock l_leu_mal_125
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_150sup4.hkl Contains datablock l_leu_mal_150
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_175sup5.hkl Contains datablock l_leu_mal_175
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_200sup6.hkl Contains datablock l_leu_mal_200
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_225sup7.hkl Contains datablock l_leu_mal_225
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_250sup8.hkl Contains datablock l_leu_mal_250
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_275sup9.hkl Contains datablock l_leu_mal_275
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_293sup10.hkl Contains datablock l_leu_mal_293
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619000441/xk5052sup11.pdf Tables S1 to S14, Figs S1 to S5
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520619000441/xk5052l_leu_mal_100sup12.cml Supplementary material

CCDC references: 1889556; 1889557; 1889558; 1889559; 1889560; 1889561; 1889562; 1889563; 1889564

Computing details top

For all structures, data collection: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018); cell refinement: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018); data reduction: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018). Program(s) used to solve structure: olex2.solve (Bourhis et al., 2015) for l_leu_mal_100, l_leu_mal_200, l_leu_mal_225, l_leu_mal_250, l_leu_mal_275, l_leu_mal_293. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

L-Leucinium hydrogen maleate (l_leu_mal_100) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.296 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.2256 (7) Å	Cell parameters from 5690 reflections
b = 5.67647 (16) Å	θ = 2.2–29.3°
c = 32.0621 (7) Å	µ = 0.11 mm⁻¹
β = 100.170 (3)°	T = 100 K
V = 3802.35 (18) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7531 independent reflections
Radiation source: fine-focus sealed X-ray tube	5508 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.899, T_max = 1.000	k = −7→6
22408 measured reflections	l = −40→40

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0494P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
7531 reflections	Δρ_max = 0.23 e Å⁻³
475 parameters	Δρ_min = −0.26 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O51	0.49686 (11)	0.6955 (4)	0.24425 (7)	0.0254 (6)
O21	0.70213 (11)	0.5542 (4)	0.50288 (7)	0.0219 (5)
O31	0.61047 (11)	0.5802 (4)	0.41752 (7)	0.0247 (6)
O42	0.28306 (11)	0.5409 (4)	0.64721 (7)	0.0214 (5)
O61	0.53003 (11)	0.4030 (4)	0.28801 (7)	0.0234 (6)
H61	0.548357	0.385748	0.313267	0.035*
O52	0.35676 (11)	0.3455 (4)	0.77694 (7)	0.0272 (6)
O22	0.51309 (11)	0.4441 (5)	0.85132 (7)	0.0233 (5)
N2	0.51390 (12)	0.1448 (5)	0.78936 (8)	0.0197 (6)
H2A	0.495372	0.248433	0.769212	0.024*
H2B	0.488544	0.127420	0.809271	0.024*
H2C	0.518790	0.002967	0.777111	0.024*
O12	0.61352 (11)	0.5691 (5)	0.85256 (8)	0.0294 (6)
H12	0.603407	0.671309	0.869142	0.044*
O53	0.41465 (11)	0.1476 (4)	−0.06639 (7)	0.0243 (6)
O33	0.41128 (11)	−0.0588 (4)	0.10602 (7)	0.0253 (5)
O62	0.32965 (11)	0.5809 (4)	0.72216 (7)	0.0234 (6)
H62	0.311250	0.570707	0.696781	0.035*
O63	0.42716 (13)	−0.1618 (4)	−0.02459 (7)	0.0295 (6)
H63	0.429233	−0.191694	0.001280	0.044*
N3	0.92004 (12)	0.0953 (5)	0.89672 (8)	0.0190 (6)
H3A	0.953599	0.090888	0.882567	0.023*
H3B	0.913965	−0.050388	0.907184	0.023*
H3C	0.928548	0.200054	0.918473	0.023*
O13	0.82956 (11)	0.4701 (5)	0.81685 (7)	0.0290 (6)
H13	0.841614	0.584319	0.803562	0.044*
O32	0.25674 (11)	0.2532 (4)	0.60058 (7)	0.0259 (6)
O11	0.64261 (12)	0.2496 (5)	0.47317 (7)	0.0267 (6)
H11	0.631562	0.345190	0.453223	0.040*
O41	0.57843 (11)	0.3510 (4)	0.36181 (7)	0.0223 (5)
O23	0.93476 (11)	0.4319 (5)	0.84202 (7)	0.0263 (6)
O43	0.43139 (14)	−0.2507 (4)	0.04990 (7)	0.0352 (7)
C92	0.31488 (16)	0.1601 (6)	0.71278 (11)	0.0234 (8)
H92	0.320044	0.015453	0.727905	0.028*
C21	0.69528 (15)	0.2075 (6)	0.54424 (10)	0.0196 (8)
H21	0.697342	0.037549	0.536380	0.024*
C102	0.33504 (15)	0.3732 (6)	0.73900 (10)	0.0198 (7)
C91	0.54180 (16)	0.8024 (6)	0.31426 (11)	0.0240 (8)
H91	0.534362	0.961637	0.305672	0.029*
N1	0.75841 (13)	0.2843 (5)	0.56795 (8)	0.0202 (6)
H1A	0.789170	0.255545	0.552110	0.024*
H1B	0.767573	0.203151	0.592760	0.024*
H1C	0.757172	0.441261	0.573515	0.024*
C71	0.58665 (15)	0.5552 (6)	0.37953 (10)	0.0206 (8)
C101	0.52191 (16)	0.6244 (6)	0.27979 (10)	0.0213 (8)
C93	0.42255 (15)	0.2225 (6)	0.00653 (10)	0.0204 (8)
H93	0.422637	0.385620	−0.000048	0.024*
C12	0.56428 (16)	0.4295 (6)	0.83989 (9)	0.0194 (7)
C22	0.57824 (15)	0.2368 (6)	0.80999 (10)	0.0189 (7)
H22	0.601469	0.107043	0.827401	0.023*
C83	0.42344 (15)	0.1741 (6)	0.04761 (10)	0.0200 (7)
H83	0.425409	0.307773	0.065613	0.024*
C73	0.42181 (16)	−0.0583 (7)	0.06933 (10)	0.0219 (7)
C72	0.27600 (15)	0.3203 (6)	0.63752 (10)	0.0198 (8)
C81	0.56805 (16)	0.7745 (6)	0.35477 (11)	0.0226 (8)
H81	0.576261	0.916636	0.370415	0.027*
C103	0.42143 (16)	0.0623 (7)	−0.03056 (11)	0.0220 (7)
C13	0.87995 (16)	0.3716 (6)	0.84086 (10)	0.0196 (7)
C82	0.29075 (16)	0.1391 (6)	0.67154 (11)	0.0244 (8)
H82	0.281395	−0.018089	0.662317	0.029*
C11	0.68093 (15)	0.3563 (7)	0.50445 (10)	0.0199 (7)
C32	0.61849 (16)	0.3123 (6)	0.77723 (10)	0.0206 (8)
H32A	0.659559	0.376474	0.792424	0.025*
H32B	0.595847	0.441579	0.760029	0.025*
C43	0.78618 (16)	0.0498 (7)	0.91938 (11)	0.0254 (8)
H43	0.824943	−0.017474	0.937816	0.030*
C41	0.57770 (17)	0.1520 (7)	0.55425 (12)	0.0300 (9)
H41	0.562658	0.232081	0.526494	0.036*
C23	0.86094 (15)	0.1697 (6)	0.86707 (10)	0.0192 (7)
H23	0.845614	0.035235	0.847772	0.023*
C61	0.53198 (19)	0.2163 (9)	0.58419 (14)	0.0441 (11)
H61A	0.545971	0.139600	0.611643	0.066*
H61B	0.488678	0.163192	0.572080	0.066*
H61C	0.531903	0.387563	0.588089	0.066*
C63	0.75083 (19)	−0.1487 (7)	0.89318 (14)	0.0377 (10)
H63A	0.711649	−0.086734	0.875869	0.057*
H63B	0.739733	−0.271474	0.912117	0.057*
H63C	0.778345	−0.215733	0.874666	0.057*
C33	0.80778 (15)	0.2398 (6)	0.89113 (10)	0.0195 (7)
H33A	0.770124	0.290047	0.870232	0.023*
H33B	0.822525	0.378149	0.909026	0.023*
C31	0.64491 (16)	0.2414 (7)	0.57210 (10)	0.0248 (8)
H31A	0.642044	0.411730	0.578134	0.030*
H31B	0.659924	0.161046	0.599453	0.030*
C51	0.5771 (2)	−0.1119 (8)	0.54660 (16)	0.0523 (13)
H51A	0.594628	−0.193136	0.573087	0.078*
H51B	0.603288	−0.148544	0.525138	0.078*
H51C	0.533048	−0.164501	0.536640	0.078*
C53	0.74402 (19)	0.1625 (8)	0.94762 (12)	0.0357 (10)
H53A	0.706504	0.233956	0.929952	0.053*
H53B	0.768381	0.284221	0.965229	0.053*
H53C	0.730035	0.041886	0.965867	0.053*
C62	0.67814 (19)	−0.0663 (8)	0.76997 (13)	0.0400 (10)
H62A	0.718434	0.008795	0.782940	0.060*
H62B	0.686704	−0.186063	0.749673	0.060*
H62C	0.658403	−0.140772	0.792048	0.060*
C42	0.63315 (17)	0.1179 (7)	0.74715 (11)	0.0257 (8)
H42	0.592027	0.038905	0.734661	0.031*
C52	0.6612 (2)	0.2299 (8)	0.71132 (12)	0.0389 (10)
H52A	0.630700	0.344335	0.696380	0.058*
H52B	0.669571	0.107333	0.691482	0.058*
H52C	0.701290	0.310089	0.723039	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.0342 (14)	0.0272 (15)	0.0124 (12)	−0.0021 (12)	−0.0023 (10)	0.0022 (11)
O21	0.0281 (13)	0.0243 (14)	0.0127 (12)	−0.0037 (12)	0.0022 (10)	0.0027 (11)
O31	0.0317 (13)	0.0293 (14)	0.0111 (12)	−0.0027 (12)	−0.0014 (10)	0.0028 (11)
O42	0.0328 (13)	0.0175 (13)	0.0127 (12)	0.0018 (11)	0.0005 (10)	0.0005 (10)
O61	0.0348 (14)	0.0212 (14)	0.0115 (11)	0.0015 (11)	−0.0030 (10)	0.0001 (10)
O52	0.0406 (14)	0.0252 (14)	0.0132 (13)	−0.0033 (12)	−0.0026 (11)	0.0030 (10)
O22	0.0267 (13)	0.0270 (13)	0.0183 (12)	−0.0002 (12)	0.0095 (10)	−0.0020 (11)
N2	0.0237 (14)	0.0210 (16)	0.0143 (14)	−0.0010 (13)	0.0030 (11)	−0.0011 (12)
O12	0.0334 (14)	0.0317 (15)	0.0245 (14)	−0.0084 (13)	0.0084 (11)	−0.0120 (12)
O53	0.0339 (13)	0.0257 (14)	0.0125 (12)	−0.0010 (11)	0.0016 (10)	0.0025 (11)
O33	0.0367 (14)	0.0251 (13)	0.0150 (12)	0.0015 (12)	0.0070 (10)	0.0016 (11)
O62	0.0369 (14)	0.0200 (13)	0.0109 (11)	0.0022 (12)	−0.0025 (10)	0.0008 (10)
O63	0.0549 (16)	0.0226 (14)	0.0098 (12)	0.0032 (13)	0.0023 (12)	0.0007 (10)
N3	0.0251 (15)	0.0208 (16)	0.0118 (13)	0.0006 (13)	0.0051 (11)	−0.0009 (12)
O13	0.0333 (14)	0.0324 (15)	0.0203 (13)	0.0017 (12)	0.0019 (11)	0.0123 (12)
O32	0.0378 (14)	0.0254 (14)	0.0118 (12)	0.0012 (12)	−0.0027 (10)	−0.0021 (11)
O11	0.0365 (14)	0.0272 (14)	0.0130 (12)	−0.0061 (12)	−0.0047 (11)	0.0033 (11)
O41	0.0309 (13)	0.0184 (12)	0.0164 (12)	0.0001 (11)	0.0012 (10)	0.0015 (10)
O23	0.0290 (14)	0.0295 (14)	0.0213 (13)	−0.0012 (12)	0.0070 (10)	0.0054 (12)
O43	0.0702 (19)	0.0181 (14)	0.0171 (13)	0.0066 (14)	0.0074 (13)	0.0000 (11)
C92	0.036 (2)	0.0148 (18)	0.0192 (18)	0.0026 (16)	0.0048 (16)	0.0037 (15)
C21	0.0233 (18)	0.0191 (18)	0.0161 (17)	0.0022 (15)	0.0025 (14)	0.0007 (14)
C102	0.0247 (17)	0.0188 (19)	0.0165 (18)	0.0008 (15)	0.0054 (14)	−0.0004 (15)
C91	0.033 (2)	0.0159 (19)	0.0199 (18)	0.0015 (16)	−0.0024 (15)	0.0001 (15)
N1	0.0287 (15)	0.0225 (16)	0.0087 (13)	0.0046 (13)	0.0015 (11)	0.0034 (12)
C71	0.0216 (17)	0.0217 (19)	0.0178 (18)	0.0011 (16)	0.0016 (14)	0.0013 (16)
C101	0.0275 (18)	0.020 (2)	0.0164 (18)	−0.0011 (15)	0.0030 (15)	0.0022 (15)
C93	0.0265 (18)	0.0153 (18)	0.0185 (18)	0.0017 (15)	0.0015 (14)	−0.0011 (14)
C12	0.0297 (19)	0.0187 (18)	0.0093 (15)	−0.0033 (16)	0.0024 (14)	0.0039 (14)
C22	0.0221 (17)	0.0206 (18)	0.0136 (16)	−0.0010 (15)	0.0021 (13)	−0.0009 (14)
C83	0.0256 (18)	0.0180 (18)	0.0164 (17)	0.0010 (15)	0.0042 (14)	−0.0027 (15)
C73	0.0297 (19)	0.0194 (18)	0.0153 (17)	0.0006 (17)	0.0004 (14)	0.0003 (15)
C72	0.0241 (18)	0.024 (2)	0.0114 (17)	0.0035 (16)	0.0028 (14)	0.0004 (14)
C81	0.0308 (19)	0.0168 (18)	0.0190 (18)	−0.0004 (16)	0.0010 (15)	−0.0035 (15)
C103	0.0242 (18)	0.0220 (19)	0.0188 (18)	0.0022 (16)	0.0010 (14)	0.0003 (16)
C13	0.0254 (19)	0.0203 (19)	0.0138 (17)	0.0009 (16)	0.0053 (14)	−0.0025 (14)
C82	0.034 (2)	0.0193 (19)	0.0186 (18)	−0.0010 (16)	0.0020 (15)	−0.0006 (15)
C11	0.0219 (17)	0.028 (2)	0.0114 (16)	−0.0007 (16)	0.0064 (14)	−0.0006 (15)
C32	0.0229 (17)	0.026 (2)	0.0134 (17)	0.0011 (15)	0.0031 (14)	0.0007 (14)
C43	0.0232 (18)	0.030 (2)	0.0228 (18)	0.0011 (17)	0.0043 (15)	0.0078 (17)
C41	0.0266 (19)	0.037 (2)	0.027 (2)	0.0043 (18)	0.0071 (16)	0.0108 (18)
C23	0.0244 (17)	0.0211 (18)	0.0115 (16)	0.0007 (15)	0.0017 (13)	−0.0011 (14)
C61	0.035 (2)	0.050 (3)	0.052 (3)	0.005 (2)	0.021 (2)	0.011 (2)
C63	0.037 (2)	0.029 (2)	0.052 (3)	−0.0073 (19)	0.019 (2)	0.002 (2)
C33	0.0233 (17)	0.0213 (18)	0.0130 (16)	−0.0012 (15)	0.0006 (14)	−0.0007 (15)
C31	0.032 (2)	0.026 (2)	0.0169 (17)	0.0015 (17)	0.0052 (15)	0.0046 (16)
C51	0.037 (2)	0.046 (3)	0.076 (3)	−0.010 (2)	0.015 (2)	−0.014 (3)
C53	0.039 (2)	0.045 (3)	0.026 (2)	−0.002 (2)	0.0151 (17)	0.0007 (19)
C62	0.053 (3)	0.028 (2)	0.045 (2)	0.006 (2)	0.027 (2)	−0.002 (2)
C42	0.0277 (19)	0.031 (2)	0.0204 (18)	−0.0071 (17)	0.0091 (15)	−0.0064 (16)
C52	0.047 (2)	0.051 (3)	0.023 (2)	0.004 (2)	0.0160 (18)	0.003 (2)

Geometric parameters (Å, º) top

O51—C101	1.237 (4)	C93—C103	1.494 (5)
O21—C11	1.214 (4)	C12—C22	1.518 (5)
O31—C71	1.241 (4)	C22—H22	1.0000
O42—C72	1.293 (4)	C22—C32	1.528 (5)
O61—H61	0.8400	C83—H83	0.9500
O61—C101	1.289 (4)	C83—C73	1.495 (5)
O52—C102	1.233 (4)	C72—C82	1.492 (5)
O22—C12	1.209 (4)	C81—H81	0.9500
N2—H2A	0.9100	C13—C23	1.517 (5)
N2—H2B	0.9100	C82—H82	0.9500
N2—H2C	0.9100	C32—H32A	0.9900
N2—C22	1.502 (4)	C32—H32B	0.9900
O12—H12	0.8400	C32—C42	1.533 (5)
O12—C12	1.317 (4)	C43—H43	1.0000
O53—C103	1.231 (4)	C43—C63	1.522 (5)
O33—C73	1.236 (4)	C43—C33	1.530 (5)
O62—H62	0.8400	C43—C53	1.522 (5)
O62—C102	1.293 (4)	C41—H41	1.0000
O63—H63	0.8400	C41—C61	1.525 (5)
O63—C103	1.289 (4)	C41—C31	1.527 (5)
N3—H3A	0.9100	C41—C51	1.518 (6)
N3—H3B	0.9100	C23—H23	1.0000
N3—H3C	0.9100	C23—C33	1.528 (5)
N3—C23	1.495 (4)	C61—H61A	0.9800
O13—H13	0.8400	C61—H61B	0.9800
O13—C13	1.326 (4)	C61—H61C	0.9800
O32—C72	1.242 (4)	C63—H63A	0.9800
O11—H11	0.8400	C63—H63B	0.9800
O11—C11	1.322 (4)	C63—H63C	0.9800
O41—C71	1.289 (4)	C33—H33A	0.9900
O23—C13	1.207 (4)	C33—H33B	0.9900
O43—C73	1.291 (4)	C31—H31A	0.9900
C92—H92	0.9500	C31—H31B	0.9900
C92—C102	1.492 (5)	C51—H51A	0.9800
C92—C82	1.336 (5)	C51—H51B	0.9800
C21—H21	1.0000	C51—H51C	0.9800
C21—N1	1.484 (4)	C53—H53A	0.9800
C21—C11	1.515 (5)	C53—H53B	0.9800
C21—C31	1.521 (5)	C53—H53C	0.9800
C91—H91	0.9500	C62—H62A	0.9800
C91—C101	1.502 (5)	C62—H62B	0.9800
C91—C81	1.329 (5)	C62—H62C	0.9800
N1—H1A	0.9100	C62—C42	1.515 (5)
N1—H1B	0.9100	C42—H42	1.0000
N1—H1C	0.9100	C42—C52	1.523 (5)
C71—C81	1.491 (5)	C52—H52A	0.9800
C93—H93	0.9500	C52—H52B	0.9800
C93—C83	1.342 (4)	C52—H52C	0.9800

C101—O61—H61	109.5	O11—C11—C21	112.9 (3)
H2A—N2—H2B	109.5	C22—C32—H32A	108.4
H2A—N2—H2C	109.5	C22—C32—H32B	108.4
H2B—N2—H2C	109.5	C22—C32—C42	115.5 (3)
C22—N2—H2A	109.5	H32A—C32—H32B	107.5
C22—N2—H2B	109.5	C42—C32—H32A	108.4
C22—N2—H2C	109.5	C42—C32—H32B	108.4
C12—O12—H12	109.5	C63—C43—H43	108.5
C102—O62—H62	109.5	C63—C43—C33	111.4 (3)
C103—O63—H63	109.5	C33—C43—H43	108.5
H3A—N3—H3B	109.5	C53—C43—H43	108.5
H3A—N3—H3C	109.5	C53—C43—C63	110.8 (3)
H3B—N3—H3C	109.5	C53—C43—C33	109.0 (3)
C23—N3—H3A	109.5	C61—C41—H41	108.2
C23—N3—H3B	109.5	C61—C41—C31	109.9 (3)
C23—N3—H3C	109.5	C31—C41—H41	108.2
C13—O13—H13	109.5	C51—C41—H41	108.2
C11—O11—H11	109.5	C51—C41—C61	110.5 (4)
C102—C92—H92	114.7	C51—C41—C31	111.7 (3)
C82—C92—H92	114.7	N3—C23—C13	106.9 (3)
C82—C92—C102	130.6 (3)	N3—C23—H23	108.8
N1—C21—H21	109.7	N3—C23—C33	111.4 (2)
N1—C21—C11	107.2 (3)	C13—C23—H23	108.8
N1—C21—C31	109.1 (3)	C13—C23—C33	112.0 (3)
C11—C21—H21	109.7	C33—C23—H23	108.8
C11—C21—C31	111.5 (3)	C41—C61—H61A	109.5
C31—C21—H21	109.7	C41—C61—H61B	109.5
O52—C102—O62	121.2 (3)	C41—C61—H61C	109.5
O52—C102—C92	118.2 (3)	H61A—C61—H61B	109.5
O62—C102—C92	120.6 (3)	H61A—C61—H61C	109.5
C101—C91—H91	114.6	H61B—C61—H61C	109.5
C81—C91—H91	114.6	C43—C63—H63A	109.5
C81—C91—C101	130.8 (3)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—H33A	108.3
H1B—N1—H1C	109.5	C43—C33—H33B	108.3
O31—C71—O41	122.3 (3)	C23—C33—C43	116.1 (3)
O31—C71—C81	116.8 (3)	C23—C33—H33A	108.3
O41—C71—C81	120.9 (3)	C23—C33—H33B	108.3
O51—C101—O61	121.8 (3)	H33A—C33—H33B	107.4
O51—C101—C91	118.5 (3)	C21—C31—C41	116.4 (3)
O61—C101—C91	119.7 (3)	C21—C31—H31A	108.2
C83—C93—H93	114.7	C21—C31—H31B	108.2
C83—C93—C103	130.7 (3)	C41—C31—H31A	108.2
C103—C93—H93	114.7	C41—C31—H31B	108.2
O22—C12—O12	124.9 (3)	H31A—C31—H31B	107.3
O22—C12—C22	121.8 (3)	C41—C51—H51A	109.5
O12—C12—C22	113.3 (3)	C41—C51—H51B	109.5
N2—C22—C12	105.4 (3)	C41—C51—H51C	109.5
N2—C22—H22	108.1	H51A—C51—H51B	109.5
N2—C22—C32	111.7 (3)	H51A—C51—H51C	109.5
C12—C22—H22	108.1	H51B—C51—H51C	109.5
C12—C22—C32	115.3 (3)	C43—C53—H53A	109.5
C32—C22—H22	108.1	C43—C53—H53B	109.5
C93—C83—H83	115.1	C43—C53—H53C	109.5
C93—C83—C73	129.8 (3)	H53A—C53—H53B	109.5
C73—C83—H83	115.1	H53A—C53—H53C	109.5
O33—C73—O43	121.9 (3)	H53B—C53—H53C	109.5
O33—C73—C83	117.9 (3)	H62A—C62—H62B	109.5
O43—C73—C83	120.2 (3)	H62A—C62—H62C	109.5
O42—C72—C82	119.4 (3)	H62B—C62—H62C	109.5
O32—C72—O42	122.1 (3)	C42—C62—H62A	109.5
O32—C72—C82	118.5 (3)	C42—C62—H62B	109.5
C91—C81—C71	130.2 (3)	C42—C62—H62C	109.5
C91—C81—H81	114.9	C32—C42—H42	108.4
C71—C81—H81	114.9	C62—C42—C32	111.9 (3)
O53—C103—O63	121.3 (3)	C62—C42—H42	108.4
O53—C103—C93	119.1 (3)	C62—C42—C52	110.8 (3)
O63—C103—C93	119.6 (3)	C52—C42—C32	108.9 (3)
O13—C13—C23	112.0 (3)	C52—C42—H42	108.4
O23—C13—O13	124.9 (3)	C42—C52—H52A	109.5
O23—C13—C23	123.1 (3)	C42—C52—H52B	109.5
C92—C82—C72	131.0 (3)	C42—C52—H52C	109.5
C92—C82—H82	114.5	H52A—C52—H52B	109.5
C72—C82—H82	114.5	H52A—C52—H52C	109.5
O21—C11—O11	125.1 (3)	H52B—C52—H52C	109.5
O21—C11—C21	122.0 (3)

O31—C71—C81—C91	−179.8 (4)	C93—C83—C73—O43	13.2 (5)
O42—C72—C82—C92	−4.4 (6)	C12—C22—C32—C42	179.6 (3)
O22—C12—C22—N2	18.3 (4)	C22—C32—C42—C62	−68.6 (4)
O22—C12—C22—C32	142.0 (3)	C22—C32—C42—C52	168.5 (3)
N2—C22—C32—C42	−60.2 (4)	C83—C93—C103—O53	173.2 (3)
O12—C12—C22—N2	−163.8 (3)	C83—C93—C103—O63	−6.4 (6)
O12—C12—C22—C32	−40.1 (4)	C81—C91—C101—O51	178.4 (4)
N3—C23—C33—C43	−59.0 (4)	C81—C91—C101—O61	−0.2 (6)
O13—C13—C23—N3	−172.5 (3)	C103—C93—C83—C73	−1.9 (6)
O13—C13—C23—C33	−50.3 (4)	C13—C23—C33—C43	−178.6 (3)
O32—C72—C82—C92	176.1 (4)	C82—C92—C102—O52	−179.3 (4)
O41—C71—C81—C91	0.6 (6)	C82—C92—C102—O62	0.8 (6)
O23—C13—C23—N3	7.8 (4)	C11—C21—C31—C41	66.8 (4)
O23—C13—C23—C33	130.0 (3)	C61—C41—C31—C21	−175.5 (3)
C102—C92—C82—C72	0.4 (7)	C63—C43—C33—C23	−69.2 (4)
N1—C21—C11—O21	−28.1 (4)	C31—C21—C11—O21	91.3 (4)
N1—C21—C11—O11	153.4 (3)	C31—C21—C11—O11	−87.3 (4)
N1—C21—C31—C41	−175.0 (3)	C51—C41—C31—C21	61.5 (4)
C101—C91—C81—C71	0.1 (7)	C53—C43—C33—C23	168.2 (3)
C93—C83—C73—O33	−166.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.84	1.59	2.425 (3)	176
N2—H2A···O61ⁱ	0.91	2.02	2.890 (3)	160
N2—H2B···O23ⁱⁱ	0.91	2.02	2.852 (4)	152
N2—H2C···O51ⁱⁱⁱ	0.91	1.88	2.763 (4)	162
O12—H12···O33^iv	0.84	1.78	2.598 (4)	164
O62—H62···O42	0.84	1.61	2.442 (3)	174
O63—H63···O43	0.84	1.59	2.427 (3)	179
N3—H3A···O22^v	0.91	1.93	2.788 (4)	156
N3—H3B···O53^vi	0.91	1.91	2.814 (4)	171
N3—H3C···O63^vii	0.91	1.99	2.856 (4)	158
O13—H13···O52^viii	0.84	1.77	2.602 (4)	172
O11—H11···O31	0.84	1.76	2.596 (3)	171
N1—H1A···O21^ix	0.91	2.14	2.870 (4)	137
N1—H1A···O31^ix	0.91	2.40	2.974 (4)	121
N1—H1B···O42^v	0.91	1.95	2.859 (3)	176
N1—H1C···O32^viii	0.91	1.97	2.863 (4)	165

Symmetry codes: (i) −x+1, y, −z+1; (ii) x−1/2, y−1/2, z; (iii) −x+1, y−1, −z+1; (iv) −x+1, y+1, −z+1; (v) x+1/2, y−1/2, z; (vi) x+1/2, y−1/2, z+1; (vii) x+1/2, y+1/2, z+1; (viii) x+1/2, y+1/2, z; (ix) −x+3/2, y−1/2, −z+1.

L-Leucinium hydrogen maleate (l_leu_mal_125) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.294 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.2633 (8) Å	Cell parameters from 5415 reflections
b = 5.67322 (19) Å	θ = 2.0–29.3°
c = 32.0530 (8) Å	µ = 0.11 mm⁻¹
β = 100.076 (3)°	T = 125 K
V = 3807.0 (2) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7553 independent reflections
Radiation source: fine-focus sealed X-ray tube	5218 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.834, T_max = 1.000	k = −7→6
22550 measured reflections	l = −40→40

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0519P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
7553 reflections	Δρ_max = 0.21 e Å⁻³
475 parameters	Δρ_min = −0.28 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O51	0.49762 (12)	0.6970 (5)	0.24462 (8)	0.0291 (7)
O21	0.70219 (12)	0.5540 (5)	0.50294 (7)	0.0248 (6)
O31	0.61080 (12)	0.5816 (5)	0.41762 (8)	0.0287 (7)
O42	0.28249 (12)	0.5402 (5)	0.64718 (7)	0.0241 (6)
O61	0.53039 (13)	0.4049 (4)	0.28823 (8)	0.0268 (6)
H61	0.546182	0.386414	0.313929	0.040*
O52	0.35595 (13)	0.3448 (5)	0.77685 (8)	0.0314 (7)
O22	0.51261 (12)	0.4457 (5)	0.85104 (8)	0.0266 (6)
N2	0.51304 (14)	0.1460 (5)	0.78920 (9)	0.0212 (7)
H2A	0.494927	0.248692	0.768777	0.025*
H2B	0.487510	0.131163	0.809065	0.025*
H2C	0.517733	0.002875	0.777300	0.025*
O12	0.61273 (12)	0.5689 (5)	0.85252 (9)	0.0334 (7)
H12	0.601753	0.677017	0.867647	0.050*
O53	0.41468 (12)	0.1490 (5)	−0.06625 (8)	0.0270 (6)
O33	0.41188 (12)	−0.0589 (5)	0.10615 (8)	0.0290 (6)
O62	0.32897 (13)	0.5801 (5)	0.72209 (8)	0.0269 (6)
H62	0.311506	0.570293	0.696533	0.040*
O63	0.42707 (15)	−0.1606 (5)	−0.02448 (8)	0.0347 (7)
H63	0.428991	−0.190296	0.001384	0.052*
N3	0.91955 (13)	0.0957 (5)	0.89669 (9)	0.0207 (7)
H3A	0.953138	0.092360	0.882576	0.025*
H3B	0.913544	−0.050457	0.906992	0.025*
H3C	0.927821	0.199971	0.918538	0.025*
O13	0.82921 (13)	0.4695 (5)	0.81679 (8)	0.0342 (7)
H13	0.840983	0.585668	0.803846	0.051*
O32	0.25619 (13)	0.2526 (5)	0.60071 (8)	0.0295 (7)
O11	0.64264 (13)	0.2507 (5)	0.47312 (8)	0.0308 (7)
H11	0.629207	0.349724	0.454170	0.046*
O41	0.57870 (12)	0.3521 (5)	0.36200 (8)	0.0250 (6)
O23	0.93406 (12)	0.4332 (5)	0.84193 (8)	0.0307 (7)
O43	0.43117 (16)	−0.2499 (5)	0.04981 (8)	0.0412 (8)
C92	0.31446 (18)	0.1594 (7)	0.71270 (12)	0.0264 (9)
H92	0.319857	0.014855	0.727880	0.032*
C21	0.69494 (16)	0.2071 (7)	0.54409 (11)	0.0210 (8)
H21	0.696967	0.037071	0.536184	0.025*
C102	0.33423 (18)	0.3729 (7)	0.73864 (11)	0.0240 (9)
C91	0.54253 (19)	0.8032 (7)	0.31441 (12)	0.0266 (9)
H91	0.535269	0.962347	0.305671	0.032*
N1	0.75782 (14)	0.2832 (5)	0.56790 (9)	0.0221 (7)
H1A	0.788670	0.253369	0.552193	0.027*
H1B	0.766630	0.202463	0.592774	0.027*
H1C	0.756732	0.440407	0.573352	0.027*
C71	0.58701 (17)	0.5566 (7)	0.37955 (11)	0.0230 (9)
C101	0.52277 (18)	0.6254 (7)	0.28019 (11)	0.0235 (9)
C93	0.42251 (17)	0.2231 (7)	0.00655 (11)	0.0229 (9)
H93	0.422571	0.386387	−0.000018	0.027*
C12	0.56371 (17)	0.4300 (7)	0.83968 (10)	0.0205 (8)
C22	0.57714 (17)	0.2369 (7)	0.80971 (11)	0.0205 (8)
H22	0.600156	0.106720	0.827076	0.025*
C83	0.42353 (17)	0.1740 (7)	0.04770 (11)	0.0229 (9)
H83	0.425747	0.307550	0.065778	0.028*
C73	0.42172 (18)	−0.0582 (7)	0.06933 (11)	0.0249 (9)
C72	0.27529 (17)	0.3202 (7)	0.63752 (11)	0.0233 (9)
C81	0.56854 (18)	0.7765 (7)	0.35501 (11)	0.0259 (9)
H81	0.576527	0.918741	0.370679	0.031*
C103	0.42129 (17)	0.0626 (7)	−0.03052 (12)	0.0239 (8)
C13	0.87958 (19)	0.3723 (7)	0.84086 (11)	0.0232 (9)
C82	0.29030 (19)	0.1381 (7)	0.67143 (11)	0.0271 (9)
H82	0.281173	−0.019254	0.662159	0.033*
C11	0.68122 (17)	0.3560 (7)	0.50441 (11)	0.0226 (8)
C32	0.61768 (18)	0.3129 (7)	0.77719 (11)	0.0236 (9)
H32A	0.595454	0.443472	0.760137	0.028*
H32B	0.658737	0.375542	0.792541	0.028*
C43	0.78609 (18)	0.0502 (8)	0.91940 (12)	0.0292 (9)
H43	0.824797	−0.017313	0.937716	0.035*
C41	0.57786 (19)	0.1516 (8)	0.55430 (13)	0.0338 (10)
H41	0.562994	0.231654	0.526532	0.041*
C23	0.86059 (17)	0.1703 (7)	0.86702 (11)	0.0213 (8)
H23	0.845376	0.035851	0.847688	0.026*
C61	0.5321 (2)	0.2169 (10)	0.58414 (16)	0.0528 (14)
H61A	0.544974	0.135873	0.611293	0.079*
H61B	0.488628	0.169010	0.571527	0.079*
H61C	0.533250	0.387672	0.588768	0.079*
C63	0.7506 (2)	−0.1479 (8)	0.89325 (16)	0.0445 (12)
H63A	0.712580	−0.084287	0.875068	0.067*
H63B	0.737836	−0.267259	0.912232	0.067*
H63C	0.778701	−0.219993	0.875618	0.067*
C33	0.80751 (17)	0.2396 (7)	0.89117 (11)	0.0221 (8)
H33A	0.822123	0.378143	0.909035	0.027*
H33B	0.769892	0.289486	0.870309	0.027*
C31	0.64443 (17)	0.2410 (8)	0.57207 (11)	0.0277 (9)
H31A	0.659383	0.160788	0.599439	0.033*
H31B	0.641470	0.411460	0.578078	0.033*
C51	0.5770 (2)	−0.1129 (9)	0.54660 (19)	0.0603 (15)
H51A	0.594929	−0.194282	0.572968	0.091*
H51B	0.602576	−0.149638	0.524811	0.091*
H51C	0.532889	−0.165165	0.537058	0.091*
C53	0.7442 (2)	0.1629 (9)	0.94778 (14)	0.0432 (12)
H53A	0.706585	0.233515	0.930229	0.065*
H53B	0.768533	0.285332	0.965196	0.065*
H53C	0.730602	0.042345	0.966210	0.065*
C62	0.6772 (2)	−0.0650 (9)	0.76988 (15)	0.0464 (12)
H62A	0.717387	0.010261	0.782744	0.070*
H62B	0.685643	−0.184774	0.749543	0.070*
H62C	0.657586	−0.139613	0.792037	0.070*
C42	0.63195 (19)	0.1200 (8)	0.74708 (12)	0.0305 (10)
H42	0.590875	0.041010	0.734696	0.037*
C52	0.6603 (2)	0.2304 (10)	0.71104 (13)	0.0463 (12)
H52A	0.629492	0.341011	0.695362	0.069*
H52B	0.669974	0.106253	0.691865	0.069*
H52C	0.699651	0.314808	0.722777	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.0406 (16)	0.0295 (17)	0.0143 (13)	0.0004 (14)	−0.0030 (12)	0.0033 (12)
O21	0.0324 (15)	0.0266 (15)	0.0141 (13)	−0.0046 (13)	0.0007 (11)	0.0030 (12)
O31	0.0376 (15)	0.0333 (16)	0.0126 (13)	−0.0038 (14)	−0.0030 (11)	0.0038 (12)
O42	0.0383 (15)	0.0183 (14)	0.0139 (13)	0.0028 (12)	0.0000 (11)	0.0009 (11)
O61	0.0418 (16)	0.0220 (16)	0.0133 (13)	0.0010 (13)	−0.0044 (12)	0.0004 (11)
O52	0.0483 (17)	0.0286 (15)	0.0139 (14)	−0.0017 (14)	−0.0036 (12)	0.0035 (12)
O22	0.0293 (15)	0.0301 (15)	0.0219 (14)	−0.0006 (13)	0.0087 (12)	−0.0054 (13)
N2	0.0282 (17)	0.0217 (17)	0.0138 (15)	−0.0004 (14)	0.0037 (13)	−0.0019 (13)
O12	0.0364 (16)	0.0370 (17)	0.0282 (16)	−0.0100 (15)	0.0098 (12)	−0.0140 (14)
O53	0.0383 (15)	0.0293 (16)	0.0119 (13)	0.0000 (13)	0.0006 (11)	0.0030 (12)
O33	0.0432 (16)	0.0290 (15)	0.0153 (13)	0.0028 (14)	0.0067 (12)	0.0023 (13)
O62	0.0449 (17)	0.0212 (14)	0.0118 (13)	0.0020 (13)	−0.0025 (12)	−0.0002 (11)
O63	0.067 (2)	0.0239 (16)	0.0111 (13)	0.0057 (15)	0.0015 (14)	0.0001 (12)
N3	0.0267 (16)	0.0215 (17)	0.0150 (15)	0.0005 (14)	0.0063 (13)	−0.0005 (13)
O13	0.0389 (16)	0.0376 (18)	0.0244 (15)	0.0018 (14)	0.0008 (13)	0.0148 (14)
O32	0.0455 (17)	0.0272 (15)	0.0126 (13)	0.0007 (14)	−0.0041 (12)	−0.0017 (12)
O11	0.0431 (17)	0.0313 (16)	0.0136 (13)	−0.0072 (14)	−0.0071 (12)	0.0044 (12)
O41	0.0359 (15)	0.0199 (14)	0.0172 (13)	0.0007 (13)	−0.0012 (11)	0.0020 (11)
O23	0.0334 (16)	0.0352 (17)	0.0244 (14)	−0.0007 (15)	0.0080 (12)	0.0077 (14)
O43	0.086 (2)	0.0184 (15)	0.0191 (15)	0.0080 (17)	0.0087 (15)	0.0013 (13)
C92	0.043 (2)	0.017 (2)	0.018 (2)	0.0042 (18)	0.0036 (17)	0.0050 (16)
C21	0.024 (2)	0.024 (2)	0.0137 (18)	0.0015 (17)	−0.0001 (15)	0.0028 (16)
C102	0.032 (2)	0.022 (2)	0.018 (2)	0.0018 (18)	0.0047 (17)	0.0006 (17)
C91	0.040 (2)	0.016 (2)	0.020 (2)	0.0030 (18)	−0.0032 (17)	0.0031 (16)
N1	0.0314 (18)	0.0244 (18)	0.0090 (14)	0.0027 (15)	−0.0005 (13)	0.0039 (13)
C71	0.025 (2)	0.026 (2)	0.0166 (19)	−0.0001 (18)	0.0010 (16)	0.0011 (18)
C101	0.029 (2)	0.023 (2)	0.018 (2)	0.0001 (17)	0.0007 (16)	0.0013 (17)
C93	0.033 (2)	0.017 (2)	0.0179 (19)	0.0019 (18)	0.0011 (16)	0.0008 (16)
C12	0.029 (2)	0.021 (2)	0.0115 (17)	−0.0005 (18)	0.0018 (16)	0.0014 (16)
C22	0.0242 (19)	0.023 (2)	0.0143 (17)	−0.0008 (17)	0.0033 (15)	−0.0001 (16)
C83	0.029 (2)	0.020 (2)	0.0190 (19)	0.0006 (17)	0.0015 (16)	−0.0034 (16)
C73	0.034 (2)	0.023 (2)	0.0169 (19)	0.0008 (19)	0.0018 (16)	0.0017 (17)
C72	0.028 (2)	0.027 (2)	0.014 (2)	0.0024 (18)	0.0011 (16)	0.0010 (16)
C81	0.038 (2)	0.019 (2)	0.0177 (19)	−0.0014 (18)	−0.0011 (17)	−0.0013 (16)
C103	0.026 (2)	0.023 (2)	0.020 (2)	0.0012 (18)	−0.0001 (16)	−0.0006 (18)
C13	0.032 (2)	0.025 (2)	0.0134 (18)	0.0020 (19)	0.0055 (16)	−0.0015 (16)
C82	0.043 (2)	0.019 (2)	0.018 (2)	−0.0014 (19)	0.0022 (18)	0.0014 (17)
C11	0.025 (2)	0.029 (2)	0.0136 (18)	0.0009 (19)	0.0045 (16)	0.0014 (17)
C32	0.027 (2)	0.028 (2)	0.0164 (19)	0.0008 (17)	0.0045 (16)	0.0008 (16)
C43	0.026 (2)	0.035 (2)	0.027 (2)	0.0009 (19)	0.0068 (17)	0.008 (2)
C41	0.029 (2)	0.042 (3)	0.031 (2)	0.004 (2)	0.0073 (18)	0.011 (2)
C23	0.0268 (19)	0.022 (2)	0.0140 (18)	−0.0002 (17)	−0.0002 (15)	−0.0007 (16)
C61	0.042 (3)	0.062 (4)	0.060 (3)	0.005 (3)	0.024 (2)	0.016 (3)
C63	0.044 (3)	0.030 (2)	0.064 (3)	−0.008 (2)	0.023 (2)	0.002 (2)
C33	0.027 (2)	0.025 (2)	0.0139 (18)	−0.0031 (18)	0.0016 (15)	−0.0019 (16)
C31	0.034 (2)	0.030 (2)	0.020 (2)	0.0044 (19)	0.0070 (17)	0.0041 (18)
C51	0.040 (3)	0.052 (4)	0.090 (4)	−0.014 (3)	0.015 (3)	−0.014 (3)
C53	0.044 (3)	0.058 (3)	0.032 (2)	−0.002 (2)	0.018 (2)	0.001 (2)
C62	0.062 (3)	0.033 (3)	0.053 (3)	0.005 (3)	0.032 (2)	−0.003 (2)
C42	0.034 (2)	0.036 (3)	0.024 (2)	−0.009 (2)	0.0126 (17)	−0.0101 (19)
C52	0.053 (3)	0.064 (3)	0.026 (2)	0.004 (3)	0.020 (2)	0.000 (2)

Geometric parameters (Å, º) top

O51—C101	1.240 (4)	C93—C103	1.494 (5)
O21—C11	1.212 (4)	C12—C22	1.517 (5)
O31—C71	1.245 (4)	C22—H22	1.0000
O42—C72	1.289 (5)	C22—C32	1.526 (5)
O61—H61	0.8400	C83—H83	0.9500
O61—C101	1.282 (5)	C83—C73	1.492 (5)
O52—C102	1.241 (4)	C72—C82	1.493 (5)
O22—C12	1.208 (4)	C81—H81	0.9500
N2—H2A	0.9100	C13—C23	1.516 (5)
N2—H2B	0.9100	C82—H82	0.9500
N2—H2C	0.9100	C32—H32A	0.9900
N2—C22	1.497 (4)	C32—H32B	0.9900
O12—H12	0.8400	C32—C42	1.524 (5)
O12—C12	1.314 (4)	C43—H43	1.0000
O53—C103	1.231 (4)	C43—C63	1.521 (6)
O33—C73	1.234 (4)	C43—C33	1.524 (5)
O62—H62	0.8400	C43—C53	1.520 (6)
O62—C102	1.286 (5)	C41—H41	1.0000
O63—H63	0.8400	C41—C61	1.525 (6)
O63—C103	1.283 (5)	C41—C31	1.518 (5)
N3—H3A	0.9100	C41—C51	1.520 (7)
N3—H3B	0.9100	C23—H23	1.0000
N3—H3C	0.9100	C23—C33	1.528 (5)
N3—C23	1.496 (4)	C61—H61A	0.9800
O13—H13	0.8400	C61—H61B	0.9800
O13—C13	1.326 (4)	C61—H61C	0.9800
O32—C72	1.239 (4)	C63—H63A	0.9800
O11—H11	0.8400	C63—H63B	0.9800
O11—C11	1.322 (4)	C63—H63C	0.9800
O41—C71	1.288 (5)	C33—H33A	0.9900
O23—C13	1.203 (4)	C33—H33B	0.9900
O43—C73	1.288 (5)	C31—H31A	0.9900
C92—H92	0.9500	C31—H31B	0.9900
C92—C102	1.488 (6)	C51—H51A	0.9800
C92—C82	1.338 (5)	C51—H51B	0.9800
C21—H21	1.0000	C51—H51C	0.9800
C21—N1	1.483 (4)	C53—H53A	0.9800
C21—C11	1.512 (5)	C53—H53B	0.9800
C21—C31	1.527 (5)	C53—H53C	0.9800
C91—H91	0.9500	C62—H62A	0.9800
C91—C101	1.495 (5)	C62—H62B	0.9800
C91—C81	1.331 (5)	C62—H62C	0.9800
N1—H1A	0.9100	C62—C42	1.521 (6)
N1—H1B	0.9100	C42—H42	1.0000
N1—H1C	0.9100	C42—C52	1.528 (6)
C71—C81	1.491 (5)	C52—H52A	0.9800
C93—H93	0.9500	C52—H52B	0.9800
C93—C83	1.345 (5)	C52—H52C	0.9800

C101—O61—H61	109.5	O11—C11—C21	112.8 (3)
H2A—N2—H2B	109.5	C22—C32—H32A	108.4
H2A—N2—H2C	109.5	C22—C32—H32B	108.4
H2B—N2—H2C	109.5	H32A—C32—H32B	107.5
C22—N2—H2A	109.5	C42—C32—C22	115.4 (3)
C22—N2—H2B	109.5	C42—C32—H32A	108.4
C22—N2—H2C	109.5	C42—C32—H32B	108.4
C12—O12—H12	109.5	C63—C43—H43	108.5
C102—O62—H62	109.5	C63—C43—C33	111.4 (3)
C103—O63—H63	109.5	C33—C43—H43	108.5
H3A—N3—H3B	109.5	C53—C43—H43	108.5
H3A—N3—H3C	109.5	C53—C43—C63	110.8 (4)
H3B—N3—H3C	109.5	C53—C43—C33	109.0 (4)
C23—N3—H3A	109.5	C61—C41—H41	108.1
C23—N3—H3B	109.5	C31—C41—H41	108.1
C23—N3—H3C	109.5	C31—C41—C61	109.8 (4)
C13—O13—H13	109.5	C31—C41—C51	112.0 (4)
C11—O11—H11	109.5	C51—C41—H41	108.1
C102—C92—H92	114.8	C51—C41—C61	110.5 (4)
C82—C92—H92	114.8	N3—C23—C13	106.9 (3)
C82—C92—C102	130.4 (4)	N3—C23—H23	108.8
N1—C21—H21	109.7	N3—C23—C33	111.2 (3)
N1—C21—C11	107.1 (3)	C13—C23—H23	108.8
N1—C21—C31	108.9 (3)	C13—C23—C33	112.2 (3)
C11—C21—H21	109.7	C33—C23—H23	108.8
C11—C21—C31	111.8 (3)	C41—C61—H61A	109.5
C31—C21—H21	109.7	C41—C61—H61B	109.5
O52—C102—O62	121.0 (4)	C41—C61—H61C	109.5
O52—C102—C92	117.8 (4)	H61A—C61—H61B	109.5
O62—C102—C92	121.2 (3)	H61A—C61—H61C	109.5
C101—C91—H91	114.5	H61B—C61—H61C	109.5
C81—C91—H91	114.5	C43—C63—H63A	109.5
C81—C91—C101	131.0 (4)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—C23	116.3 (3)
H1B—N1—H1C	109.5	C43—C33—H33A	108.2
O31—C71—O41	122.2 (4)	C43—C33—H33B	108.2
O31—C71—C81	116.5 (4)	C23—C33—H33A	108.2
O41—C71—C81	121.3 (3)	C23—C33—H33B	108.2
O51—C101—O61	121.6 (3)	H33A—C33—H33B	107.4
O51—C101—C91	118.3 (3)	C21—C31—H31A	108.2
O61—C101—C91	120.1 (3)	C21—C31—H31B	108.2
C83—C93—H93	114.8	C41—C31—C21	116.3 (3)
C83—C93—C103	130.5 (4)	C41—C31—H31A	108.2
C103—C93—H93	114.8	C41—C31—H31B	108.2
O22—C12—O12	124.6 (3)	H31A—C31—H31B	107.4
O22—C12—C22	121.5 (3)	C41—C51—H51A	109.5
O12—C12—C22	113.9 (3)	C41—C51—H51B	109.5
N2—C22—C12	105.6 (3)	C41—C51—H51C	109.5
N2—C22—H22	108.0	H51A—C51—H51B	109.5
N2—C22—C32	112.1 (3)	H51A—C51—H51C	109.5
C12—C22—H22	108.0	H51B—C51—H51C	109.5
C12—C22—C32	114.8 (3)	C43—C53—H53A	109.5
C32—C22—H22	108.0	C43—C53—H53B	109.5
C93—C83—H83	115.1	C43—C53—H53C	109.5
C93—C83—C73	129.9 (4)	H53A—C53—H53B	109.5
C73—C83—H83	115.1	H53A—C53—H53C	109.5
O33—C73—O43	121.9 (4)	H53B—C53—H53C	109.5
O33—C73—C83	118.0 (4)	H62A—C62—H62B	109.5
O43—C73—C83	120.1 (3)	H62A—C62—H62C	109.5
O42—C72—C82	119.6 (3)	H62B—C62—H62C	109.5
O32—C72—O42	122.2 (3)	C42—C62—H62A	109.5
O32—C72—C82	118.2 (3)	C42—C62—H62B	109.5
C91—C81—C71	129.6 (4)	C42—C62—H62C	109.5
C91—C81—H81	115.2	C32—C42—H42	108.4
C71—C81—H81	115.2	C32—C42—C52	109.4 (4)
O53—C103—O63	121.7 (4)	C62—C42—C32	111.7 (3)
O53—C103—C93	118.7 (4)	C62—C42—H42	108.4
O63—C103—C93	119.6 (3)	C62—C42—C52	110.3 (4)
O13—C13—C23	111.7 (3)	C52—C42—H42	108.4
O23—C13—O13	125.0 (4)	C42—C52—H52A	109.5
O23—C13—C23	123.3 (3)	C42—C52—H52B	109.5
C92—C82—C72	130.8 (4)	C42—C52—H52C	109.5
C92—C82—H82	114.6	H52A—C52—H52B	109.5
C72—C82—H82	114.6	H52A—C52—H52C	109.5
O21—C11—O11	125.0 (3)	H52B—C52—H52C	109.5
O21—C11—C21	122.1 (3)

O31—C71—C81—C91	179.9 (4)	C93—C83—C73—O43	13.5 (6)
O42—C72—C82—C92	−3.9 (7)	C12—C22—C32—C42	179.6 (3)
O22—C12—C22—N2	18.0 (5)	C22—C32—C42—C62	−69.3 (4)
O22—C12—C22—C32	142.1 (3)	C22—C32—C42—C52	168.3 (3)
N2—C22—C32—C42	−59.9 (4)	C83—C93—C103—O53	173.5 (4)
O12—C12—C22—N2	−164.0 (3)	C83—C93—C103—O63	−6.4 (6)
O12—C12—C22—C32	−39.9 (4)	C81—C91—C101—O51	178.0 (4)
N3—C23—C33—C43	−58.8 (4)	C81—C91—C101—O61	−0.2 (7)
O13—C13—C23—N3	−172.8 (3)	C103—C93—C83—C73	−2.2 (7)
O13—C13—C23—C33	−50.7 (4)	C13—C23—C33—C43	−178.5 (3)
O32—C72—C82—C92	176.1 (4)	C82—C92—C102—O52	−179.5 (4)
O41—C71—C81—C91	0.0 (7)	C82—C92—C102—O62	0.6 (7)
O23—C13—C23—N3	7.8 (5)	C11—C21—C31—C41	67.1 (4)
O23—C13—C23—C33	130.0 (4)	C61—C41—C31—C21	−175.2 (4)
C102—C92—C82—C72	0.3 (8)	C63—C43—C33—C23	−69.5 (4)
N1—C21—C11—O21	−28.6 (5)	C31—C21—C11—O21	90.7 (4)
N1—C21—C11—O11	154.0 (3)	C31—C21—C11—O11	−86.8 (4)
N1—C21—C31—C41	−174.7 (3)	C51—C41—C31—C21	61.5 (5)
C101—C91—C81—C71	0.6 (8)	C53—C43—C33—C23	167.9 (3)
C93—C83—C73—O33	−167.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.84	1.59	2.426 (3)	178
N2—H2A···O61ⁱ	0.91	2.02	2.893 (4)	161
N2—H2B···O23ⁱⁱ	0.91	2.02	2.851 (4)	151
N2—H2C···O51ⁱⁱⁱ	0.91	1.88	2.762 (4)	163
O12—H12···O33^iv	0.84	1.77	2.595 (4)	168
O62—H62···O42	0.84	1.60	2.442 (3)	176
O63—H63···O43	0.84	1.58	2.421 (4)	179
N3—H3A···O22^v	0.91	1.94	2.792 (4)	155
N3—H3B···O53^vi	0.91	1.91	2.809 (4)	171
N3—H3C···O63^vii	0.91	1.99	2.860 (4)	159
O13—H13···O52^viii	0.84	1.76	2.598 (4)	173
O11—H11···O31	0.84	1.76	2.594 (4)	172
N1—H1A···O21^ix	0.91	2.14	2.872 (4)	137
N1—H1A···O31^ix	0.91	2.39	2.979 (4)	122
N1—H1B···O42^v	0.91	1.95	2.858 (4)	177
N1—H1C···O32^viii	0.91	1.98	2.866 (4)	165

L-Leucinium hydrogen maleate (l_leu_mal_150) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.288 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.3300 (7) Å	Cell parameters from 5339 reflections
b = 5.67423 (16) Å	θ = 2.0–29.3°
c = 32.0776 (7) Å	µ = 0.11 mm⁻¹
β = 99.937 (3)°	T = 150 K
V = 3824.14 (18) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7593 independent reflections
Radiation source: fine-focus sealed X-ray tube	5342 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.915, T_max = 1.000	k = −7→6
22679 measured reflections	l = −40→40

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0506P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
7593 reflections	Δρ_max = 0.21 e Å⁻³
475 parameters	Δρ_min = −0.30 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O51	0.49869 (13)	0.6974 (5)	0.24492 (8)	0.0356 (7)
O21	0.70242 (12)	0.5528 (5)	0.50289 (7)	0.0305 (6)
O31	0.61135 (12)	0.5813 (5)	0.41772 (8)	0.0344 (7)
O42	0.28175 (12)	0.5389 (5)	0.64725 (7)	0.0297 (6)
O61	0.53104 (13)	0.4053 (5)	0.28851 (8)	0.0326 (6)
H61	0.547409	0.387260	0.314064	0.049*
O52	0.35520 (13)	0.3439 (5)	0.77658 (8)	0.0385 (7)
O22	0.51186 (12)	0.4461 (5)	0.85087 (8)	0.0334 (6)
N2	0.51220 (13)	0.1466 (5)	0.78889 (9)	0.0267 (7)
H2A	0.494515	0.248977	0.768341	0.032*
H2B	0.486514	0.133447	0.808666	0.032*
H2C	0.516727	0.002898	0.777187	0.032*
O12	0.61174 (13)	0.5676 (6)	0.85229 (9)	0.0409 (7)
H12	0.602036	0.667436	0.869428	0.061*
O53	0.41472 (12)	0.1488 (5)	−0.06607 (8)	0.0332 (6)
O33	0.41236 (13)	−0.0593 (5)	0.10627 (8)	0.0349 (6)
O62	0.32807 (13)	0.5786 (5)	0.72196 (8)	0.0323 (6)
H62	0.310267	0.568377	0.696540	0.048*
O63	0.42672 (16)	−0.1610 (5)	−0.02447 (8)	0.0428 (8)
H63	0.428782	−0.191114	0.001367	0.064*
N3	0.91915 (13)	0.0966 (6)	0.89659 (9)	0.0265 (7)
H3A	0.952405	0.090170	0.882267	0.032*
H3B	0.913015	−0.048127	0.907446	0.032*
H3C	0.927850	0.202953	0.918042	0.032*
O13	0.82887 (13)	0.4684 (6)	0.81675 (9)	0.0410 (7)
H13	0.840733	0.582276	0.803296	0.062*
O32	0.25575 (13)	0.2510 (5)	0.60075 (8)	0.0361 (7)
O11	0.64240 (13)	0.2507 (5)	0.47328 (8)	0.0374 (7)
H11	0.631615	0.347150	0.453465	0.056*
O41	0.57912 (12)	0.3526 (5)	0.36221 (8)	0.0306 (6)
O23	0.93343 (12)	0.4334 (5)	0.84186 (8)	0.0375 (7)
O43	0.43112 (17)	−0.2504 (5)	0.04985 (9)	0.0505 (9)
C92	0.31355 (19)	0.1583 (7)	0.71258 (12)	0.0325 (9)
H92	0.318475	0.013838	0.727748	0.039*
C21	0.69461 (16)	0.2055 (7)	0.54406 (11)	0.0266 (8)
H21	0.696542	0.035630	0.536103	0.032*
C102	0.33358 (18)	0.3709 (7)	0.73869 (11)	0.0285 (9)
C91	0.54327 (19)	0.8038 (7)	0.31476 (12)	0.0327 (9)
H91	0.536044	0.963248	0.306238	0.039*
N1	0.75741 (14)	0.2816 (6)	0.56782 (9)	0.0280 (7)
H1A	0.788261	0.249010	0.552304	0.034*
H1B	0.765803	0.202914	0.592892	0.034*
H1C	0.756616	0.439301	0.572827	0.034*
C71	0.58751 (17)	0.5568 (7)	0.37985 (11)	0.0283 (9)
C101	0.52333 (18)	0.6271 (7)	0.28037 (11)	0.0289 (9)
C93	0.42234 (17)	0.2225 (7)	0.00669 (11)	0.0284 (9)
H93	0.422248	0.385723	0.000117	0.034*
C12	0.56272 (18)	0.4302 (7)	0.83943 (11)	0.0267 (8)
C22	0.57630 (16)	0.2368 (7)	0.80948 (11)	0.0251 (8)
H22	0.599127	0.106361	0.826797	0.030*
C83	0.42345 (17)	0.1741 (7)	0.04778 (11)	0.0279 (8)
H83	0.425537	0.307741	0.065798	0.033*
C73	0.42189 (18)	−0.0586 (7)	0.06942 (11)	0.0293 (8)
C72	0.27484 (18)	0.3188 (7)	0.63747 (11)	0.0281 (9)
C81	0.56943 (18)	0.7757 (7)	0.35531 (12)	0.0318 (9)
H81	0.577799	0.917857	0.370938	0.038*
C103	0.42122 (18)	0.0629 (7)	−0.03036 (12)	0.0300 (9)
C13	0.87911 (18)	0.3713 (7)	0.84080 (11)	0.0281 (9)
C82	0.28984 (19)	0.1364 (7)	0.67147 (11)	0.0329 (9)
H82	0.280998	−0.021055	0.662235	0.040*
C11	0.68094 (17)	0.3554 (7)	0.50444 (11)	0.0271 (8)
C32	0.61662 (18)	0.3125 (7)	0.77687 (11)	0.0286 (9)
H32A	0.594294	0.442282	0.759757	0.034*
H32B	0.657411	0.376296	0.792121	0.034*
C43	0.78579 (19)	0.0494 (8)	0.91935 (13)	0.0371 (10)
H43	0.824274	−0.019422	0.937492	0.044*
C41	0.57764 (19)	0.1513 (8)	0.55432 (14)	0.0410 (11)
H41	0.562869	0.231600	0.526613	0.049*
C23	0.86042 (17)	0.1699 (7)	0.86712 (10)	0.0257 (8)
H23	0.845311	0.034961	0.847943	0.031*
C61	0.5317 (2)	0.2147 (11)	0.58409 (17)	0.0632 (15)
H61A	0.544333	0.132620	0.611109	0.095*
H61B	0.488474	0.167079	0.571334	0.095*
H61C	0.532764	0.385307	0.588957	0.095*
C63	0.7501 (2)	−0.1474 (8)	0.89310 (17)	0.0568 (14)
H63A	0.712198	−0.082658	0.875139	0.085*
H63B	0.737308	−0.267207	0.911973	0.085*
H63C	0.777881	−0.219196	0.875269	0.085*
C33	0.80752 (17)	0.2397 (7)	0.89125 (11)	0.0277 (8)
H33A	0.770172	0.290569	0.870437	0.033*
H33B	0.822194	0.377664	0.909200	0.033*
C31	0.64419 (17)	0.2399 (8)	0.57198 (12)	0.0319 (9)
H31A	0.658972	0.159636	0.599305	0.038*
H31B	0.641382	0.410387	0.577989	0.038*
C51	0.5771 (2)	−0.1140 (10)	0.5465 (2)	0.0739 (18)
H51A	0.594772	−0.195629	0.572822	0.111*
H51B	0.603018	−0.149964	0.524834	0.111*
H51C	0.533319	−0.166836	0.536737	0.111*
C53	0.7444 (2)	0.1619 (10)	0.94795 (14)	0.0539 (13)
H53A	0.707060	0.234431	0.930586	0.081*
H53B	0.768909	0.282883	0.965514	0.081*
H53C	0.730502	0.041020	0.966181	0.081*
C62	0.6763 (2)	−0.0630 (9)	0.76957 (16)	0.0599 (14)
H62A	0.715454	0.014284	0.783565	0.090*
H62B	0.686715	−0.178245	0.749046	0.090*
H62C	0.656069	−0.143509	0.790787	0.090*
C42	0.63128 (19)	0.1198 (8)	0.74692 (13)	0.0376 (10)
H42	0.590496	0.039771	0.734642	0.045*
C52	0.6592 (2)	0.2302 (10)	0.71088 (14)	0.0567 (13)
H52A	0.628704	0.342957	0.695677	0.085*
H52B	0.667995	0.106545	0.691362	0.085*
H52C	0.698835	0.312226	0.722419	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.0503 (17)	0.0341 (17)	0.0191 (14)	−0.0004 (14)	−0.0033 (12)	0.0034 (12)
O21	0.0405 (15)	0.0313 (15)	0.0185 (13)	−0.0058 (14)	0.0017 (11)	0.0034 (12)
O31	0.0448 (15)	0.0381 (16)	0.0174 (13)	−0.0022 (14)	−0.0029 (11)	0.0041 (12)
O42	0.0453 (15)	0.0231 (14)	0.0189 (13)	0.0029 (12)	0.0007 (12)	0.0020 (11)
O61	0.0494 (16)	0.0271 (16)	0.0180 (13)	0.0004 (13)	−0.0030 (12)	0.0010 (11)
O52	0.0591 (18)	0.0349 (16)	0.0178 (14)	−0.0030 (15)	−0.0041 (13)	0.0047 (12)
O22	0.0384 (15)	0.0369 (16)	0.0269 (14)	0.0009 (14)	0.0112 (12)	−0.0049 (13)
N2	0.0354 (17)	0.0267 (17)	0.0185 (15)	−0.0024 (15)	0.0062 (13)	−0.0026 (13)
O12	0.0452 (16)	0.0442 (18)	0.0350 (17)	−0.0117 (15)	0.0114 (13)	−0.0169 (15)
O53	0.0466 (15)	0.0350 (16)	0.0173 (13)	−0.0003 (13)	0.0033 (11)	0.0032 (12)
O33	0.0529 (17)	0.0335 (15)	0.0190 (14)	0.0031 (15)	0.0082 (12)	0.0033 (13)
O62	0.0520 (17)	0.0254 (14)	0.0167 (13)	0.0012 (13)	−0.0022 (12)	0.0003 (11)
O63	0.079 (2)	0.0292 (17)	0.0177 (14)	0.0051 (16)	0.0016 (15)	−0.0006 (12)
N3	0.0338 (16)	0.0271 (18)	0.0195 (15)	0.0011 (14)	0.0069 (13)	−0.0007 (13)
O13	0.0443 (16)	0.0464 (19)	0.0309 (16)	0.0020 (15)	0.0026 (13)	0.0182 (14)
O32	0.0554 (17)	0.0311 (15)	0.0182 (14)	0.0011 (14)	−0.0039 (12)	−0.0020 (12)
O11	0.0482 (17)	0.0377 (16)	0.0212 (14)	−0.0100 (14)	−0.0081 (12)	0.0061 (13)
O41	0.0438 (15)	0.0238 (14)	0.0227 (14)	−0.0008 (13)	0.0012 (12)	0.0036 (11)
O23	0.0395 (16)	0.0432 (17)	0.0317 (15)	−0.0023 (15)	0.0120 (12)	0.0089 (14)
O43	0.104 (3)	0.0233 (16)	0.0248 (15)	0.0088 (17)	0.0131 (16)	0.0023 (13)
C92	0.051 (2)	0.021 (2)	0.025 (2)	0.0036 (19)	0.0044 (18)	0.0050 (16)
C21	0.032 (2)	0.028 (2)	0.0194 (18)	0.0025 (17)	0.0029 (15)	0.0030 (16)
C102	0.040 (2)	0.026 (2)	0.019 (2)	−0.0001 (18)	0.0050 (17)	0.0011 (16)
C91	0.050 (2)	0.020 (2)	0.026 (2)	0.0023 (18)	−0.0004 (18)	0.0033 (16)
N1	0.0378 (18)	0.0308 (18)	0.0144 (15)	0.0058 (15)	0.0017 (13)	0.0047 (13)
C71	0.032 (2)	0.030 (2)	0.023 (2)	0.0007 (18)	0.0022 (16)	0.0011 (18)
C101	0.037 (2)	0.025 (2)	0.023 (2)	−0.0015 (18)	0.0005 (16)	0.0036 (16)
C93	0.038 (2)	0.023 (2)	0.024 (2)	0.0030 (18)	0.0034 (16)	0.0004 (16)
C12	0.037 (2)	0.027 (2)	0.0163 (18)	−0.0030 (18)	0.0039 (16)	0.0006 (16)
C22	0.0297 (19)	0.027 (2)	0.0180 (17)	−0.0021 (17)	0.0032 (15)	−0.0011 (16)
C83	0.038 (2)	0.0226 (19)	0.0230 (19)	0.0005 (17)	0.0054 (16)	−0.0036 (16)
C73	0.042 (2)	0.025 (2)	0.0192 (19)	0.0008 (19)	0.0021 (16)	−0.0010 (17)
C72	0.037 (2)	0.029 (2)	0.018 (2)	0.0015 (18)	0.0049 (16)	0.0008 (16)
C81	0.045 (2)	0.024 (2)	0.024 (2)	0.0002 (18)	0.0005 (17)	−0.0030 (16)
C103	0.037 (2)	0.029 (2)	0.024 (2)	0.0012 (19)	0.0040 (16)	−0.0005 (17)
C13	0.036 (2)	0.029 (2)	0.0195 (19)	0.0001 (19)	0.0058 (16)	−0.0020 (17)
C82	0.052 (2)	0.023 (2)	0.022 (2)	−0.0014 (19)	0.0029 (18)	0.0007 (17)
C11	0.030 (2)	0.035 (2)	0.0167 (18)	−0.0012 (18)	0.0051 (15)	−0.0003 (17)
C32	0.034 (2)	0.030 (2)	0.023 (2)	−0.0004 (17)	0.0081 (16)	−0.0007 (16)
C43	0.032 (2)	0.045 (3)	0.035 (2)	0.000 (2)	0.0087 (17)	0.013 (2)
C41	0.037 (2)	0.049 (3)	0.039 (2)	0.006 (2)	0.0107 (19)	0.012 (2)
C23	0.0334 (19)	0.028 (2)	0.0150 (17)	0.0010 (17)	0.0022 (15)	−0.0016 (16)
C61	0.049 (3)	0.074 (4)	0.074 (4)	0.006 (3)	0.030 (3)	0.016 (3)
C63	0.053 (3)	0.036 (3)	0.088 (4)	−0.009 (2)	0.030 (3)	0.002 (3)
C33	0.032 (2)	0.030 (2)	0.0215 (19)	−0.0015 (17)	0.0031 (15)	0.0004 (17)
C31	0.037 (2)	0.034 (2)	0.026 (2)	0.0033 (19)	0.0091 (17)	0.0045 (18)
C51	0.053 (3)	0.058 (4)	0.114 (5)	−0.015 (3)	0.022 (3)	−0.015 (4)
C53	0.057 (3)	0.070 (4)	0.041 (3)	−0.005 (3)	0.025 (2)	0.001 (3)
C62	0.078 (3)	0.041 (3)	0.071 (3)	0.008 (3)	0.044 (3)	−0.004 (3)
C42	0.040 (2)	0.044 (3)	0.032 (2)	−0.007 (2)	0.0146 (18)	−0.011 (2)
C52	0.065 (3)	0.076 (4)	0.034 (3)	0.004 (3)	0.024 (2)	0.001 (3)

Geometric parameters (Å, º) top

O51—C101	1.234 (4)	C93—C103	1.491 (5)
O21—C11	1.214 (4)	C12—C22	1.519 (5)
O31—C71	1.241 (4)	C22—H22	1.0000
O42—C72	1.290 (5)	C22—C32	1.526 (5)
O61—H61	0.8400	C83—H83	0.9500
O61—C101	1.290 (5)	C83—C73	1.495 (5)
O52—C102	1.233 (4)	C72—C82	1.498 (5)
O22—C12	1.207 (4)	C81—H81	0.9500
N2—H2A	0.9100	C13—C23	1.515 (5)
N2—H2B	0.9100	C82—H82	0.9500
N2—H2C	0.9100	C32—H32A	0.9900
N2—C22	1.502 (4)	C32—H32B	0.9900
O12—H12	0.8400	C32—C42	1.523 (5)
O12—C12	1.312 (4)	C43—H43	1.0000
O53—C103	1.231 (4)	C43—C63	1.521 (6)
O33—C73	1.233 (4)	C43—C33	1.529 (6)
O62—H62	0.8400	C43—C53	1.519 (6)
O62—C102	1.292 (5)	C41—H41	1.0000
O63—H63	0.8400	C41—C61	1.525 (6)
O63—C103	1.287 (5)	C41—C31	1.520 (5)
N3—H3A	0.9100	C41—C51	1.526 (7)
N3—H3B	0.9100	C23—H23	1.0000
N3—H3C	0.9100	C23—C33	1.527 (5)
N3—C23	1.492 (4)	C61—H61A	0.9800
O13—H13	0.8400	C61—H61B	0.9800
O13—C13	1.327 (4)	C61—H61C	0.9800
O32—C72	1.239 (4)	C63—H63A	0.9800
O11—H11	0.8400	C63—H63B	0.9800
O11—C11	1.321 (4)	C63—H63C	0.9800
O41—C71	1.288 (5)	C33—H33A	0.9900
O23—C13	1.206 (4)	C33—H33B	0.9900
O43—C73	1.288 (5)	C31—H31A	0.9900
C92—H92	0.9500	C31—H31B	0.9900
C92—C102	1.488 (5)	C51—H51A	0.9800
C92—C82	1.334 (5)	C51—H51B	0.9800
C21—H21	1.0000	C51—H51C	0.9800
C21—N1	1.486 (4)	C53—H53A	0.9800
C21—C11	1.515 (5)	C53—H53B	0.9800
C21—C31	1.526 (5)	C53—H53C	0.9800
C91—H91	0.9500	C62—H62A	0.9800
C91—C101	1.497 (5)	C62—H62B	0.9800
C91—C81	1.333 (5)	C62—H62C	0.9800
N1—H1A	0.9100	C62—C42	1.512 (6)
N1—H1B	0.9100	C42—H42	1.0000
N1—H1C	0.9100	C42—C52	1.523 (6)
C71—C81	1.486 (5)	C52—H52A	0.9800
C93—H93	0.9500	C52—H52B	0.9800
C93—C83	1.343 (5)	C52—H52C	0.9800

C101—O61—H61	109.5	O11—C11—C21	112.8 (3)
H2A—N2—H2B	109.5	C22—C32—H32A	108.4
H2A—N2—H2C	109.5	C22—C32—H32B	108.4
H2B—N2—H2C	109.5	H32A—C32—H32B	107.5
C22—N2—H2A	109.5	C42—C32—C22	115.6 (3)
C22—N2—H2B	109.5	C42—C32—H32A	108.4
C22—N2—H2C	109.5	C42—C32—H32B	108.4
C12—O12—H12	109.5	C63—C43—H43	108.5
C102—O62—H62	109.5	C63—C43—C33	111.4 (4)
C103—O63—H63	109.5	C33—C43—H43	108.5
H3A—N3—H3B	109.5	C53—C43—H43	108.5
H3A—N3—H3C	109.5	C53—C43—C63	110.8 (4)
H3B—N3—H3C	109.5	C53—C43—C33	109.0 (4)
C23—N3—H3A	109.5	C61—C41—H41	108.1
C23—N3—H3B	109.5	C61—C41—C51	110.4 (4)
C23—N3—H3C	109.5	C31—C41—H41	108.1
C13—O13—H13	109.5	C31—C41—C61	110.4 (4)
C11—O11—H11	109.5	C31—C41—C51	111.5 (4)
C102—C92—H92	114.5	C51—C41—H41	108.1
C82—C92—H92	114.5	N3—C23—C13	106.9 (3)
C82—C92—C102	130.9 (4)	N3—C23—H23	108.8
N1—C21—H21	109.7	N3—C23—C33	111.4 (3)
N1—C21—C11	107.1 (3)	C13—C23—H23	108.8
N1—C21—C31	109.0 (3)	C13—C23—C33	112.0 (3)
C11—C21—H21	109.7	C33—C23—H23	108.8
C11—C21—C31	111.6 (3)	C41—C61—H61A	109.5
C31—C21—H21	109.7	C41—C61—H61B	109.5
O52—C102—O62	120.9 (4)	C41—C61—H61C	109.5
O52—C102—C92	118.5 (4)	H61A—C61—H61B	109.5
O62—C102—C92	120.6 (3)	H61A—C61—H61C	109.5
C101—C91—H91	114.5	H61B—C61—H61C	109.5
C81—C91—H91	114.5	C43—C63—H63A	109.5
C81—C91—C101	131.0 (4)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—H33A	108.2
H1B—N1—H1C	109.5	C43—C33—H33B	108.2
O31—C71—O41	122.2 (4)	C23—C33—C43	116.2 (3)
O31—C71—C81	116.8 (4)	C23—C33—H33A	108.2
O41—C71—C81	121.0 (3)	C23—C33—H33B	108.2
O51—C101—O61	121.4 (3)	H33A—C33—H33B	107.4
O51—C101—C91	119.0 (3)	C21—C31—H31A	108.2
O61—C101—C91	119.6 (3)	C21—C31—H31B	108.2
C83—C93—H93	114.6	C41—C31—C21	116.5 (3)
C83—C93—C103	130.8 (4)	C41—C31—H31A	108.2
C103—C93—H93	114.6	C41—C31—H31B	108.2
O22—C12—O12	124.7 (4)	H31A—C31—H31B	107.3
O22—C12—C22	121.7 (3)	C41—C51—H51A	109.5
O12—C12—C22	113.5 (3)	C41—C51—H51B	109.5
N2—C22—C12	105.4 (3)	C41—C51—H51C	109.5
N2—C22—H22	108.1	H51A—C51—H51B	109.5
N2—C22—C32	111.9 (3)	H51A—C51—H51C	109.5
C12—C22—H22	108.1	H51B—C51—H51C	109.5
C12—C22—C32	114.9 (3)	C43—C53—H53A	109.5
C32—C22—H22	108.1	C43—C53—H53B	109.5
C93—C83—H83	115.2	C43—C53—H53C	109.5
C93—C83—C73	129.7 (4)	H53A—C53—H53B	109.5
C73—C83—H83	115.2	H53A—C53—H53C	109.5
O33—C73—O43	121.9 (4)	H53B—C53—H53C	109.5
O33—C73—C83	117.9 (3)	H62A—C62—H62B	109.5
O43—C73—C83	120.1 (3)	H62A—C62—H62C	109.5
O42—C72—C82	119.4 (3)	H62B—C62—H62C	109.5
O32—C72—O42	122.5 (3)	C42—C62—H62A	109.5
O32—C72—C82	118.1 (3)	C42—C62—H62B	109.5
C91—C81—C71	130.0 (4)	C42—C62—H62C	109.5
C91—C81—H81	115.0	C32—C42—H42	108.4
C71—C81—H81	115.0	C32—C42—C52	109.5 (4)
O53—C103—O63	121.4 (4)	C62—C42—C32	111.8 (4)
O53—C103—C93	119.0 (4)	C62—C42—H42	108.4
O63—C103—C93	119.6 (3)	C62—C42—C52	110.3 (4)
O13—C13—C23	111.9 (3)	C52—C42—H42	108.4
O23—C13—O13	124.8 (4)	C42—C52—H52A	109.5
O23—C13—C23	123.3 (3)	C42—C52—H52B	109.5
C92—C82—C72	130.7 (4)	C42—C52—H52C	109.5
C92—C82—H82	114.6	H52A—C52—H52B	109.5
C72—C82—H82	114.6	H52A—C52—H52C	109.5
O21—C11—O11	125.0 (3)	H52B—C52—H52C	109.5
O21—C11—C21	122.2 (3)

O31—C71—C81—C91	−180.0 (4)	C93—C83—C73—O43	13.1 (6)
O42—C72—C82—C92	−3.9 (7)	C12—C22—C32—C42	179.3 (3)
O22—C12—C22—N2	18.4 (5)	C22—C32—C42—C62	−69.3 (4)
O22—C12—C22—C32	142.0 (4)	C22—C32—C42—C52	168.1 (3)
N2—C22—C32—C42	−60.5 (4)	C83—C93—C103—O53	173.8 (4)
O12—C12—C22—N2	−164.1 (3)	C83—C93—C103—O63	−5.9 (6)
O12—C12—C22—C32	−40.4 (4)	C81—C91—C101—O51	178.6 (4)
N3—C23—C33—C43	−59.5 (4)	C81—C91—C101—O61	0.0 (7)
O13—C13—C23—N3	−172.8 (3)	C103—C93—C83—C73	−2.1 (7)
O13—C13—C23—C33	−50.5 (4)	C13—C23—C33—C43	−179.1 (3)
O32—C72—C82—C92	176.5 (4)	C82—C92—C102—O52	−179.0 (4)
O41—C71—C81—C91	0.6 (7)	C82—C92—C102—O62	1.4 (7)
O23—C13—C23—N3	7.4 (5)	C11—C21—C31—C41	67.2 (4)
O23—C13—C23—C33	129.6 (4)	C61—C41—C31—C21	−175.6 (4)
C102—C92—C82—C72	−0.4 (8)	C63—C43—C33—C23	−69.7 (4)
N1—C21—C11—O21	−27.8 (5)	C31—C21—C11—O21	91.4 (4)
N1—C21—C11—O11	154.2 (3)	C31—C21—C11—O11	−86.7 (4)
N1—C21—C31—C41	−174.8 (3)	C51—C41—C31—C21	61.2 (5)
C101—C91—C81—C71	0.0 (8)	C53—C43—C33—C23	167.7 (3)
C93—C83—C73—O33	−167.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.84	1.59	2.428 (3)	179
N2—H2A···O61ⁱ	0.91	2.02	2.895 (4)	162
N2—H2B···O23ⁱⁱ	0.91	2.03	2.856 (4)	150
N2—H2C···O51ⁱⁱⁱ	0.91	1.88	2.764 (4)	163
O12—H12···O33^iv	0.84	1.79	2.598 (4)	162
O62—H62···O42	0.84	1.60	2.440 (3)	175
O63—H63···O43	0.84	1.58	2.423 (4)	179
N3—H3A···O22^v	0.91	1.93	2.791 (4)	157
N3—H3B···O53^vi	0.91	1.92	2.817 (4)	171
N3—H3C···O63^vii	0.91	2.00	2.861 (4)	157
O13—H13···O52^viii	0.84	1.77	2.601 (4)	171
O11—H11···O31	0.84	1.76	2.593 (4)	172
N1—H1A···O21^ix	0.91	2.13	2.870 (4)	138
N1—H1A···O31^ix	0.91	2.39	2.982 (4)	123
N1—H1B···O42^v	0.91	1.95	2.863 (4)	178
N1—H1C···O32^viii	0.91	1.98	2.868 (4)	163

L-Leucinium hydrogen maleate (l_leu_mal_175) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.285 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.3889 (8) Å	Cell parameters from 5053 reflections
b = 5.67352 (19) Å	θ = 2.0–29.2°
c = 32.0754 (8) Å	µ = 0.11 mm⁻¹
β = 99.818 (3)°	T = 175 K
V = 3835.4 (2) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7614 independent reflections
Radiation source: fine-focus sealed X-ray tube	5110 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.665, T_max = 1.000	k = −7→6
22830 measured reflections	l = −40→40

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0463P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
7614 reflections	Δρ_max = 0.21 e Å⁻³
475 parameters	Δρ_min = −0.28 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O51	0.49959 (15)	0.6993 (6)	0.24534 (9)	0.0433 (8)
O21	0.70265 (14)	0.5516 (6)	0.50300 (9)	0.0369 (7)
O31	0.61174 (15)	0.5825 (6)	0.41787 (9)	0.0417 (8)
O42	0.28097 (15)	0.5372 (5)	0.64725 (9)	0.0357 (7)
O61	0.53161 (16)	0.4065 (5)	0.28886 (9)	0.0390 (8)
H61	0.546351	0.388160	0.314648	0.059*
O52	0.35440 (16)	0.3426 (6)	0.77647 (10)	0.0464 (9)
O22	0.51108 (14)	0.4477 (6)	0.85065 (9)	0.0398 (8)
N2	0.51127 (16)	0.1486 (7)	0.78862 (11)	0.0326 (8)
H2A	0.494023	0.250858	0.767967	0.039*
H2B	0.485400	0.136646	0.808292	0.039*
H2C	0.515657	0.004385	0.777036	0.039*
O12	0.61098 (15)	0.5668 (7)	0.85221 (11)	0.0490 (9)
H12	0.601186	0.668290	0.869054	0.073*
O53	0.41467 (15)	0.1497 (6)	−0.06588 (9)	0.0410 (8)
O33	0.41297 (15)	−0.0595 (6)	0.10643 (9)	0.0436 (8)
O62	0.32731 (16)	0.5774 (5)	0.72185 (9)	0.0390 (8)
H62	0.311436	0.567135	0.696090	0.058*
O63	0.42677 (19)	−0.1603 (6)	−0.02440 (10)	0.0502 (9)
H63	0.426982	−0.190608	0.001263	0.075*
N3	0.91902 (16)	0.0977 (7)	0.89667 (11)	0.0326 (8)
H3A	0.952273	0.091563	0.882384	0.039*
H3B	0.912962	−0.047076	0.907542	0.039*
H3C	0.927501	0.204232	0.918094	0.039*
O13	0.82866 (15)	0.4676 (7)	0.81674 (11)	0.0491 (9)
H13	0.840585	0.577067	0.802297	0.074*
O32	0.25534 (16)	0.2496 (6)	0.60077 (9)	0.0438 (8)
O11	0.64239 (16)	0.2514 (6)	0.47335 (10)	0.0458 (9)
H11	0.630457	0.349482	0.454011	0.069*
O41	0.57962 (15)	0.3536 (6)	0.36237 (10)	0.0381 (8)
O23	0.93264 (15)	0.4347 (7)	0.84172 (10)	0.0456 (8)
O43	0.4310 (2)	−0.2499 (6)	0.04982 (10)	0.0609 (11)
C92	0.3129 (2)	0.1568 (8)	0.71253 (14)	0.0402 (12)
H92	0.317940	0.012513	0.727755	0.048*
C21	0.6941 (2)	0.2050 (8)	0.54405 (13)	0.0330 (10)
H21	0.696004	0.035272	0.535971	0.040*
C102	0.3327 (2)	0.3695 (8)	0.73837 (14)	0.0360 (11)
C91	0.5440 (2)	0.8056 (8)	0.31492 (14)	0.0411 (12)
H91	0.537004	0.965080	0.306325	0.049*
N1	0.75669 (16)	0.2799 (7)	0.56788 (10)	0.0328 (9)
H1A	0.787361	0.250838	0.552076	0.039*
H1B	0.765337	0.197819	0.592572	0.039*
H1C	0.755688	0.436793	0.573602	0.039*
C71	0.5879 (2)	0.5577 (9)	0.37996 (14)	0.0341 (10)
C101	0.5239 (2)	0.6278 (8)	0.28075 (14)	0.0362 (11)
C93	0.4222 (2)	0.2225 (8)	0.00682 (13)	0.0352 (11)
H93	0.421937	0.385855	0.000306	0.042*
C12	0.5618 (2)	0.4301 (8)	0.83926 (13)	0.0327 (10)
C22	0.57510 (19)	0.2374 (8)	0.80931 (13)	0.0298 (9)
H22	0.597653	0.106348	0.826532	0.036*
C83	0.4235 (2)	0.1736 (8)	0.04798 (14)	0.0356 (11)
H83	0.425818	0.307038	0.066072	0.043*
C73	0.4219 (2)	−0.0593 (9)	0.06947 (14)	0.0368 (11)
C72	0.2745 (2)	0.3166 (8)	0.63749 (14)	0.0342 (11)
C81	0.5700 (2)	0.7768 (8)	0.35546 (15)	0.0400 (12)
H81	0.578465	0.918735	0.371113	0.048*
C103	0.4211 (2)	0.0633 (9)	−0.03041 (14)	0.0370 (11)
C13	0.8788 (2)	0.3710 (8)	0.84067 (13)	0.0345 (10)
C82	0.2893 (2)	0.1348 (8)	0.67147 (14)	0.0400 (12)
H82	0.280404	−0.022686	0.662283	0.048*
C11	0.6811 (2)	0.3557 (9)	0.50450 (13)	0.0333 (10)
C32	0.6153 (2)	0.3126 (8)	0.77669 (14)	0.0354 (11)
H32A	0.593060	0.442198	0.759561	0.043*
H32B	0.655916	0.376712	0.791915	0.043*
C43	0.7858 (2)	0.0491 (10)	0.91924 (16)	0.0446 (12)
H43	0.824112	−0.020821	0.937189	0.054*
C41	0.5777 (2)	0.1488 (10)	0.55415 (17)	0.0500 (14)
H41	0.563127	0.229109	0.526450	0.060*
C23	0.8606 (2)	0.1702 (8)	0.86715 (13)	0.0322 (10)
H23	0.845759	0.034739	0.848059	0.039*
C61	0.5319 (3)	0.2141 (14)	0.5841 (2)	0.077 (2)
H61A	0.544895	0.134305	0.611311	0.115*
H61B	0.488881	0.164811	0.571691	0.115*
H61C	0.532750	0.385083	0.588529	0.115*
C63	0.7497 (3)	−0.1469 (10)	0.8929 (2)	0.0680 (18)
H63A	0.712490	−0.080326	0.874627	0.102*
H63B	0.735830	−0.264620	0.911798	0.102*
H63C	0.777420	−0.221827	0.875475	0.102*
C33	0.8073 (2)	0.2386 (8)	0.89139 (13)	0.0341 (10)
H33A	0.821708	0.376544	0.909391	0.041*
H33B	0.770135	0.289136	0.870576	0.041*
C31	0.6438 (2)	0.2387 (9)	0.57201 (14)	0.0393 (11)
H31A	0.658436	0.158287	0.599324	0.047*
H31B	0.640704	0.409032	0.578033	0.047*
C51	0.5771 (3)	−0.1149 (13)	0.5464 (3)	0.088 (2)
H51A	0.594911	−0.196374	0.572702	0.132*
H51B	0.602643	−0.151083	0.524598	0.132*
H51C	0.533361	−0.167633	0.536931	0.132*
C53	0.7448 (3)	0.1625 (13)	0.94809 (18)	0.0657 (17)
H53A	0.707751	0.236549	0.930894	0.099*
H53B	0.769596	0.282256	0.965722	0.099*
H53C	0.730712	0.041602	0.966256	0.099*
C62	0.6753 (3)	−0.0627 (11)	0.7693 (2)	0.0710 (18)
H62A	0.714872	0.013905	0.782402	0.106*
H62B	0.684561	−0.180625	0.748811	0.106*
H62C	0.655747	−0.140011	0.791133	0.106*
C42	0.6302 (2)	0.1205 (9)	0.74672 (16)	0.0450 (13)
H42	0.589650	0.040016	0.734460	0.054*
C52	0.6580 (3)	0.2309 (13)	0.71064 (17)	0.0687 (18)
H52A	0.627790	0.344904	0.695689	0.103*
H52B	0.666301	0.107361	0.690926	0.103*
H52C	0.697774	0.311333	0.722072	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.060 (2)	0.042 (2)	0.0237 (17)	−0.0028 (17)	−0.0046 (15)	0.0035 (15)
O21	0.0489 (18)	0.0360 (18)	0.0244 (16)	−0.0043 (16)	0.0023 (14)	0.0046 (15)
O31	0.0545 (19)	0.046 (2)	0.0213 (16)	−0.0026 (18)	−0.0031 (14)	0.0039 (15)
O42	0.0546 (19)	0.0287 (17)	0.0223 (16)	0.0035 (15)	0.0022 (14)	0.0013 (13)
O61	0.060 (2)	0.0308 (18)	0.0224 (16)	−0.0003 (16)	−0.0026 (15)	0.0005 (14)
O52	0.070 (2)	0.0410 (19)	0.0242 (17)	−0.0030 (18)	−0.0042 (16)	0.0052 (15)
O22	0.0460 (19)	0.0427 (19)	0.0335 (18)	0.0000 (17)	0.0146 (15)	−0.0062 (16)
N2	0.042 (2)	0.033 (2)	0.0242 (19)	−0.0014 (17)	0.0074 (16)	−0.0027 (16)
O12	0.054 (2)	0.052 (2)	0.043 (2)	−0.0142 (19)	0.0147 (16)	−0.0202 (18)
O53	0.056 (2)	0.042 (2)	0.0233 (17)	−0.0021 (16)	0.0021 (14)	0.0045 (15)
O33	0.065 (2)	0.0429 (19)	0.0235 (17)	0.0040 (19)	0.0085 (15)	0.0042 (16)
O62	0.062 (2)	0.0297 (17)	0.0218 (16)	0.0018 (16)	−0.0015 (15)	0.0004 (14)
O63	0.094 (3)	0.0336 (19)	0.0209 (17)	0.0052 (19)	0.0028 (18)	−0.0006 (15)
N3	0.039 (2)	0.037 (2)	0.0226 (18)	0.0059 (18)	0.0065 (15)	0.0006 (16)
O13	0.055 (2)	0.053 (2)	0.036 (2)	0.0027 (18)	0.0010 (16)	0.0190 (17)
O32	0.066 (2)	0.0398 (19)	0.0215 (16)	−0.0004 (18)	−0.0039 (15)	−0.0034 (15)
O11	0.059 (2)	0.045 (2)	0.0283 (18)	−0.0113 (18)	−0.0082 (16)	0.0060 (16)
O41	0.0532 (19)	0.0298 (16)	0.0290 (17)	−0.0004 (15)	0.0008 (14)	0.0046 (14)
O23	0.048 (2)	0.050 (2)	0.041 (2)	−0.0012 (18)	0.0138 (16)	0.0118 (18)
O43	0.128 (3)	0.0270 (18)	0.0282 (18)	0.010 (2)	0.016 (2)	0.0000 (16)
C92	0.065 (3)	0.025 (2)	0.030 (3)	0.004 (2)	0.006 (2)	0.007 (2)
C21	0.039 (2)	0.035 (3)	0.023 (2)	−0.001 (2)	0.0004 (18)	0.002 (2)
C102	0.053 (3)	0.032 (2)	0.023 (2)	0.001 (2)	0.005 (2)	0.003 (2)
C91	0.061 (3)	0.027 (3)	0.031 (3)	0.003 (2)	−0.006 (2)	0.002 (2)
N1	0.044 (2)	0.034 (2)	0.0191 (18)	0.0030 (18)	0.0018 (15)	0.0042 (16)
C71	0.040 (2)	0.034 (2)	0.027 (2)	0.000 (2)	0.0029 (19)	0.001 (2)
C101	0.046 (3)	0.033 (3)	0.028 (3)	−0.001 (2)	0.002 (2)	0.001 (2)
C93	0.051 (3)	0.029 (2)	0.025 (2)	0.004 (2)	0.004 (2)	0.002 (2)
C12	0.044 (3)	0.033 (2)	0.020 (2)	−0.003 (2)	0.0029 (19)	0.001 (2)
C22	0.036 (2)	0.032 (2)	0.021 (2)	−0.003 (2)	0.0052 (17)	−0.0025 (19)
C83	0.049 (3)	0.029 (2)	0.029 (2)	0.001 (2)	0.005 (2)	−0.003 (2)
C73	0.053 (3)	0.032 (2)	0.024 (2)	0.001 (2)	0.002 (2)	−0.002 (2)
C72	0.045 (3)	0.031 (3)	0.027 (2)	0.006 (2)	0.005 (2)	0.0005 (19)
C81	0.060 (3)	0.027 (2)	0.030 (2)	−0.001 (2)	−0.001 (2)	0.002 (2)
C103	0.045 (3)	0.036 (3)	0.028 (2)	0.002 (2)	0.002 (2)	0.000 (2)
C13	0.048 (3)	0.035 (3)	0.021 (2)	0.001 (2)	0.008 (2)	0.001 (2)
C82	0.061 (3)	0.028 (2)	0.029 (2)	0.001 (2)	0.002 (2)	−0.001 (2)
C11	0.039 (2)	0.040 (3)	0.021 (2)	−0.001 (2)	0.0038 (18)	0.001 (2)
C32	0.040 (2)	0.040 (3)	0.027 (2)	−0.002 (2)	0.0086 (19)	−0.001 (2)
C43	0.039 (3)	0.052 (3)	0.044 (3)	0.001 (2)	0.009 (2)	0.014 (3)
C41	0.043 (3)	0.062 (4)	0.046 (3)	0.006 (3)	0.012 (2)	0.016 (3)
C23	0.042 (2)	0.034 (2)	0.021 (2)	0.002 (2)	0.0045 (18)	0.0003 (19)
C61	0.057 (4)	0.090 (5)	0.091 (5)	0.010 (4)	0.037 (3)	0.021 (4)
C63	0.067 (4)	0.039 (3)	0.106 (5)	−0.010 (3)	0.039 (4)	0.001 (4)
C33	0.040 (2)	0.036 (2)	0.026 (2)	−0.003 (2)	0.0041 (19)	−0.002 (2)
C31	0.047 (3)	0.046 (3)	0.027 (2)	0.005 (2)	0.012 (2)	0.005 (2)
C51	0.065 (4)	0.069 (5)	0.131 (7)	−0.016 (4)	0.020 (4)	−0.015 (5)
C53	0.063 (3)	0.087 (5)	0.053 (4)	−0.001 (3)	0.030 (3)	0.001 (3)
C62	0.094 (4)	0.046 (3)	0.086 (5)	0.012 (4)	0.052 (4)	−0.002 (4)
C42	0.049 (3)	0.049 (3)	0.041 (3)	−0.010 (3)	0.018 (2)	−0.013 (2)
C52	0.082 (4)	0.092 (5)	0.040 (3)	0.009 (4)	0.032 (3)	0.007 (3)

Geometric parameters (Å, º) top

O51—C101	1.234 (5)	C93—C103	1.494 (6)
O21—C11	1.207 (5)	C12—C22	1.514 (6)
O31—C71	1.243 (5)	C22—H22	1.0000
O42—C72	1.292 (5)	C22—C32	1.525 (6)
O61—H61	0.8400	C83—H83	0.9500
O61—C101	1.287 (5)	C83—C73	1.493 (6)
O52—C102	1.240 (5)	C72—C82	1.495 (6)
O22—C12	1.206 (5)	C81—H81	0.9500
N2—H2A	0.9100	C13—C23	1.511 (6)
N2—H2B	0.9100	C82—H82	0.9500
N2—H2C	0.9100	C32—H32A	0.9900
N2—C22	1.500 (5)	C32—H32B	0.9900
O12—H12	0.8400	C32—C42	1.523 (6)
O12—C12	1.316 (5)	C43—H43	1.0000
O53—C103	1.225 (5)	C43—C63	1.524 (8)
O33—C73	1.233 (5)	C43—C33	1.519 (7)
O62—H62	0.8400	C43—C53	1.522 (7)
O62—C102	1.290 (5)	C41—H41	1.0000
O63—H63	0.8400	C41—C61	1.530 (8)
O63—C103	1.286 (6)	C41—C31	1.519 (7)
N3—H3A	0.9100	C41—C51	1.516 (9)
N3—H3B	0.9100	C23—H23	1.0000
N3—H3C	0.9100	C23—C33	1.534 (6)
N3—C23	1.492 (5)	C61—H61A	0.9800
O13—H13	0.8400	C61—H61B	0.9800
O13—C13	1.326 (5)	C61—H61C	0.9800
O32—C72	1.239 (5)	C63—H63A	0.9800
O11—H11	0.8400	C63—H63B	0.9800
O11—C11	1.324 (5)	C63—H63C	0.9800
O41—C71	1.287 (5)	C33—H33A	0.9900
O23—C13	1.202 (5)	C33—H33B	0.9900
O43—C73	1.283 (6)	C31—H31A	0.9900
C92—H92	0.9500	C31—H31B	0.9900
C92—C102	1.484 (7)	C51—H51A	0.9800
C92—C82	1.334 (6)	C51—H51B	0.9800
C21—H21	1.0000	C51—H51C	0.9800
C21—N1	1.485 (5)	C53—H53A	0.9800
C21—C11	1.516 (6)	C53—H53B	0.9800
C21—C31	1.527 (6)	C53—H53C	0.9800
C91—H91	0.9500	C62—H62A	0.9800
C91—C101	1.498 (6)	C62—H62B	0.9800
C91—C81	1.335 (6)	C62—H62C	0.9800
N1—H1A	0.9100	C62—C42	1.515 (8)
N1—H1B	0.9100	C42—H42	1.0000
N1—H1C	0.9100	C42—C52	1.523 (7)
C71—C81	1.485 (6)	C52—H52A	0.9800
C93—H93	0.9500	C52—H52B	0.9800
C93—C83	1.345 (6)	C52—H52C	0.9800

C101—O61—H61	109.5	O11—C11—C21	112.4 (4)
H2A—N2—H2B	109.5	C22—C32—H32A	108.3
H2A—N2—H2C	109.5	C22—C32—H32B	108.3
H2B—N2—H2C	109.5	H32A—C32—H32B	107.4
C22—N2—H2A	109.5	C42—C32—C22	115.9 (4)
C22—N2—H2B	109.5	C42—C32—H32A	108.3
C22—N2—H2C	109.5	C42—C32—H32B	108.3
C12—O12—H12	109.5	C63—C43—H43	108.5
C102—O62—H62	109.5	C33—C43—H43	108.5
C103—O63—H63	109.5	C33—C43—C63	111.5 (4)
H3A—N3—H3B	109.5	C33—C43—C53	108.8 (5)
H3A—N3—H3C	109.5	C53—C43—H43	108.5
H3B—N3—H3C	109.5	C53—C43—C63	110.8 (5)
C23—N3—H3A	109.5	C61—C41—H41	108.1
C23—N3—H3B	109.5	C31—C41—H41	108.1
C23—N3—H3C	109.5	C31—C41—C61	109.6 (5)
C13—O13—H13	109.5	C51—C41—H41	108.1
C11—O11—H11	109.5	C51—C41—C61	110.7 (6)
C102—C92—H92	114.7	C51—C41—C31	112.0 (5)
C82—C92—H92	114.7	N3—C23—C13	107.2 (4)
C82—C92—C102	130.7 (4)	N3—C23—H23	108.7
N1—C21—H21	109.6	N3—C23—C33	111.2 (3)
N1—C21—C11	106.9 (4)	C13—C23—H23	108.7
N1—C21—C31	109.0 (3)	C13—C23—C33	112.3 (4)
C11—C21—H21	109.6	C33—C23—H23	108.7
C11—C21—C31	112.0 (4)	C41—C61—H61A	109.5
C31—C21—H21	109.6	C41—C61—H61B	109.5
O52—C102—O62	120.6 (4)	C41—C61—H61C	109.5
O52—C102—C92	118.3 (4)	H61A—C61—H61B	109.5
O62—C102—C92	121.1 (4)	H61A—C61—H61C	109.5
C101—C91—H91	114.7	H61B—C61—H61C	109.5
C81—C91—H91	114.7	C43—C63—H63A	109.5
C81—C91—C101	130.6 (4)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—C23	116.4 (4)
H1B—N1—H1C	109.5	C43—C33—H33A	108.2
O31—C71—O41	122.2 (4)	C43—C33—H33B	108.2
O31—C71—C81	116.7 (4)	C23—C33—H33A	108.2
O41—C71—C81	121.1 (4)	C23—C33—H33B	108.2
O51—C101—O61	121.7 (4)	H33A—C33—H33B	107.3
O51—C101—C91	118.4 (4)	C21—C31—H31A	108.3
O61—C101—C91	119.9 (4)	C21—C31—H31B	108.3
C83—C93—H93	114.5	C41—C31—C21	116.1 (4)
C83—C93—C103	130.9 (4)	C41—C31—H31A	108.3
C103—C93—H93	114.5	C41—C31—H31B	108.3
O22—C12—O12	124.5 (4)	H31A—C31—H31B	107.4
O22—C12—C22	121.9 (4)	C41—C51—H51A	109.5
O12—C12—C22	113.5 (4)	C41—C51—H51B	109.5
N2—C22—C12	105.6 (3)	C41—C51—H51C	109.5
N2—C22—H22	108.2	H51A—C51—H51B	109.5
N2—C22—C32	111.6 (3)	H51A—C51—H51C	109.5
C12—C22—H22	108.2	H51B—C51—H51C	109.5
C12—C22—C32	115.0 (4)	C43—C53—H53A	109.5
C32—C22—H22	108.2	C43—C53—H53B	109.5
C93—C83—H83	115.2	C43—C53—H53C	109.5
C93—C83—C73	129.6 (4)	H53A—C53—H53B	109.5
C73—C83—H83	115.2	H53A—C53—H53C	109.5
O33—C73—O43	122.2 (5)	H53B—C53—H53C	109.5
O33—C73—C83	117.7 (4)	H62A—C62—H62B	109.5
O43—C73—C83	120.1 (4)	H62A—C62—H62C	109.5
O42—C72—C82	119.4 (4)	H62B—C62—H62C	109.5
O32—C72—O42	122.1 (4)	C42—C62—H62A	109.5
O32—C72—C82	118.4 (4)	C42—C62—H62B	109.5
C91—C81—C71	130.2 (4)	C42—C62—H62C	109.5
C91—C81—H81	114.9	C32—C42—H42	108.3
C71—C81—H81	114.9	C32—C42—C52	109.6 (5)
O53—C103—O63	121.8 (4)	C62—C42—C32	112.0 (4)
O53—C103—C93	119.0 (4)	C62—C42—H42	108.3
O63—C103—C93	119.2 (4)	C62—C42—C52	110.2 (5)
O13—C13—C23	112.1 (4)	C52—C42—H42	108.3
O23—C13—O13	124.6 (4)	C42—C52—H52A	109.5
O23—C13—C23	123.3 (4)	C42—C52—H52B	109.5
C92—C82—C72	130.8 (4)	C42—C52—H52C	109.5
C92—C82—H82	114.6	H52A—C52—H52B	109.5
C72—C82—H82	114.6	H52A—C52—H52C	109.5
O21—C11—O11	125.1 (4)	H52B—C52—H52C	109.5
O21—C11—C21	122.4 (4)

O31—C71—C81—C91	−180.0 (5)	C93—C83—C73—O43	13.2 (8)
O42—C72—C82—C92	−4.5 (8)	C12—C22—C32—C42	179.0 (4)
O22—C12—C22—N2	18.2 (6)	C22—C32—C42—C62	−69.3 (5)
O22—C12—C22—C32	141.6 (4)	C22—C32—C42—C52	168.0 (4)
N2—C22—C32—C42	−60.8 (5)	C83—C93—C103—O53	174.0 (5)
O12—C12—C22—N2	−164.0 (4)	C83—C93—C103—O63	−5.9 (8)
O12—C12—C22—C32	−40.5 (5)	C81—C91—C101—O51	178.8 (5)
N3—C23—C33—C43	−59.5 (5)	C81—C91—C101—O61	−0.5 (9)
O13—C13—C23—N3	−172.5 (4)	C103—C93—C83—C73	−2.5 (8)
O13—C13—C23—C33	−50.0 (5)	C13—C23—C33—C43	−179.6 (4)
O32—C72—C82—C92	176.6 (5)	C82—C92—C102—O52	−179.0 (5)
O41—C71—C81—C91	0.7 (9)	C82—C92—C102—O62	1.3 (9)
O23—C13—C23—N3	7.0 (6)	C11—C21—C31—C41	67.6 (5)
O23—C13—C23—C33	129.5 (5)	C61—C41—C31—C21	−175.2 (5)
C102—C92—C82—C72	−0.2 (10)	C63—C43—C33—C23	−70.5 (5)
N1—C21—C11—O21	−27.9 (6)	C31—C21—C11—O21	91.4 (5)
N1—C21—C11—O11	154.5 (4)	C31—C21—C11—O11	−86.2 (5)
N1—C21—C31—C41	−174.4 (4)	C51—C41—C31—C21	61.5 (7)
C101—C91—C81—C71	0.3 (10)	C53—C43—C33—C23	167.0 (4)
C93—C83—C73—O33	−168.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.84	1.59	2.425 (4)	176
N2—H2A···O61ⁱ	0.91	2.02	2.895 (4)	162
N2—H2B···O23ⁱⁱ	0.91	2.04	2.860 (5)	150
N2—H2C···O51ⁱⁱⁱ	0.91	1.88	2.766 (5)	164
O12—H12···O33^iv	0.84	1.78	2.598 (5)	163
O62—H62···O42	0.84	1.60	2.440 (4)	178
O63—H63···O43	0.84	1.58	2.421 (5)	177
N3—H3A···O22^v	0.91	1.93	2.788 (5)	157
N3—H3B···O53^vi	0.91	1.92	2.819 (5)	171
N3—H3C···O63^vii	0.91	2.00	2.860 (5)	157
O13—H13···O52^viii	0.84	1.77	2.596 (5)	168
O11—H11···O31	0.84	1.76	2.594 (4)	172
N1—H1A···O21^ix	0.91	2.14	2.877 (5)	138
N1—H1A···O31^ix	0.91	2.41	2.991 (5)	122
N1—H1B···O42^v	0.91	1.95	2.863 (4)	176
N1—H1C···O32^viii	0.91	1.98	2.868 (5)	166

L-Leucinium hydrogen maleate (l_leu_mal_200) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.280 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.4563 (9) Å	Cell parameters from 4785 reflections
b = 5.67251 (19) Å	θ = 2.1–29.4°
c = 32.0779 (8) Å	µ = 0.11 mm⁻¹
β = 99.653 (3)°	T = 200 K
V = 3849.0 (2) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7634 independent reflections
Radiation source: fine-focus sealed X-ray tube	4962 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.619, T_max = 1.000	k = −7→6
22918 measured reflections	l = −40→40

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0494P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
7634 reflections	Δρ_max = 0.22 e Å⁻³
475 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint

Special details top

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

	x	y	z	U_iso*/U_eq
O51	0.50070 (16)	0.7011 (6)	0.24581 (9)	0.0482 (9)
O21	0.70295 (14)	0.5512 (6)	0.50303 (9)	0.0409 (8)
O31	0.61248 (15)	0.5830 (6)	0.41794 (9)	0.0474 (9)
O42	0.28029 (15)	0.5360 (6)	0.64730 (9)	0.0406 (8)
O61	0.53213 (16)	0.4077 (5)	0.28918 (9)	0.0435 (8)
H61	0.546326	0.388773	0.314999	0.065*
O52	0.35374 (17)	0.3417 (6)	0.77632 (10)	0.0533 (9)
O22	0.51033 (15)	0.4492 (6)	0.85034 (10)	0.0454 (8)
N2	0.51034 (16)	0.1497 (7)	0.78847 (11)	0.0361 (9)
H2A	0.492890	0.252547	0.768028	0.043*
H2B	0.484732	0.136189	0.808268	0.043*
H2C	0.514842	0.006163	0.776672	0.043*
O12	0.60979 (16)	0.5660 (7)	0.85196 (11)	0.0561 (10)
H12	0.600421	0.664945	0.869396	0.084*
O53	0.41468 (16)	0.1504 (6)	−0.06571 (9)	0.0471 (8)
O33	0.41350 (16)	−0.0596 (6)	0.10663 (9)	0.0483 (8)
O62	0.32635 (17)	0.5759 (6)	0.72173 (9)	0.0447 (8)
H62	0.308167	0.566022	0.696481	0.067*
O63	0.4263 (2)	−0.1592 (6)	−0.02430 (10)	0.0592 (11)
H63	0.428168	−0.189300	0.001519	0.089*
N3	0.91862 (16)	0.0986 (7)	0.89658 (11)	0.0368 (9)
H3A	0.951646	0.093227	0.882129	0.044*
H3B	0.912820	−0.046361	0.907461	0.044*
H3C	0.927052	0.205156	0.917988	0.044*
O13	0.82834 (16)	0.4657 (7)	0.81659 (11)	0.0550 (9)
H13	0.839954	0.578082	0.802657	0.082*
O32	0.25484 (16)	0.2475 (6)	0.60096 (9)	0.0506 (9)
O11	0.64239 (17)	0.2518 (7)	0.47347 (10)	0.0516 (9)
H11	0.630723	0.350461	0.454212	0.077*
O41	0.57998 (15)	0.3543 (6)	0.36258 (10)	0.0417 (8)
O23	0.93192 (16)	0.4361 (7)	0.84169 (10)	0.0516 (9)
O43	0.4308 (2)	−0.2498 (6)	0.04989 (10)	0.0689 (12)
C92	0.3123 (2)	0.1556 (9)	0.71253 (14)	0.0454 (12)
H92	0.317314	0.011156	0.727708	0.055*
C21	0.6937 (2)	0.2029 (9)	0.54401 (13)	0.0362 (10)
H21	0.695539	0.032992	0.535969	0.043*
C102	0.3320 (2)	0.3685 (8)	0.73830 (14)	0.0387 (11)
C91	0.5450 (2)	0.8059 (8)	0.31528 (14)	0.0451 (12)
H91	0.538397	0.965513	0.306716	0.054*
N1	0.75604 (16)	0.2783 (7)	0.56800 (10)	0.0366 (9)
H1A	0.786764	0.250043	0.552228	0.044*
H1B	0.764572	0.195904	0.592637	0.044*
H1C	0.754874	0.435156	0.573797	0.044*
C71	0.5886 (2)	0.5581 (9)	0.38003 (13)	0.0368 (10)
C101	0.5250 (2)	0.6292 (8)	0.28116 (14)	0.0406 (11)
C93	0.4223 (2)	0.2226 (9)	0.00708 (13)	0.0401 (11)
H93	0.422193	0.386034	0.000577	0.048*
C12	0.5607 (2)	0.4301 (8)	0.83906 (13)	0.0375 (10)
C22	0.57378 (19)	0.2390 (8)	0.80895 (13)	0.0326 (9)
H22	0.596165	0.107679	0.826098	0.039*
C83	0.4235 (2)	0.1742 (8)	0.04805 (14)	0.0403 (11)
H83	0.425807	0.307680	0.066130	0.048*
C73	0.4218 (2)	−0.0589 (9)	0.06955 (14)	0.0409 (11)
C72	0.2737 (2)	0.3157 (8)	0.63756 (14)	0.0379 (11)
C81	0.5708 (2)	0.7768 (9)	0.35580 (15)	0.0448 (12)
H81	0.578895	0.918551	0.371542	0.054*
C103	0.4211 (2)	0.0638 (9)	−0.03012 (14)	0.0401 (11)
C13	0.8784 (2)	0.3712 (9)	0.84072 (13)	0.0386 (11)
C82	0.2887 (2)	0.1344 (8)	0.67143 (14)	0.0455 (12)
H82	0.280009	−0.023161	0.662208	0.055*
C11	0.6811 (2)	0.3544 (9)	0.50451 (13)	0.0368 (10)
C32	0.6141 (2)	0.3127 (8)	0.77624 (14)	0.0409 (11)
H32A	0.592056	0.442321	0.759082	0.049*
H32B	0.654507	0.376853	0.791450	0.049*
C43	0.7854 (2)	0.0473 (10)	0.91903 (17)	0.0514 (13)
H43	0.823495	−0.023445	0.936877	0.062*
C41	0.5778 (2)	0.1484 (11)	0.55426 (18)	0.0568 (15)
H41	0.563313	0.228947	0.526605	0.068*
C23	0.8600 (2)	0.1706 (8)	0.86723 (13)	0.0363 (10)
H23	0.845186	0.035010	0.848201	0.044*
C61	0.5317 (3)	0.2138 (15)	0.5842 (2)	0.089 (2)
H61A	0.545778	0.141238	0.611863	0.134*
H61B	0.489345	0.156415	0.572413	0.134*
H61C	0.530669	0.385530	0.587289	0.134*
C63	0.7494 (3)	−0.1478 (11)	0.8928 (2)	0.080 (2)
H63A	0.712272	−0.080894	0.874660	0.120*
H63B	0.735642	−0.265921	0.911645	0.120*
H63C	0.776915	−0.222447	0.875175	0.120*
C33	0.8072 (2)	0.2390 (9)	0.89165 (14)	0.0384 (11)
H33A	0.821902	0.375210	0.909986	0.046*
H33B	0.770291	0.292010	0.871042	0.046*
C31	0.6436 (2)	0.2380 (10)	0.57181 (14)	0.0454 (12)
H31A	0.658098	0.158694	0.599205	0.054*
H31B	0.640595	0.408676	0.577604	0.054*
C51	0.5771 (3)	−0.1151 (13)	0.5463 (3)	0.100 (3)
H51A	0.596810	−0.196881	0.572044	0.150*
H51B	0.600731	−0.149807	0.523362	0.150*
H51C	0.533341	−0.168929	0.538227	0.150*
C53	0.7448 (3)	0.1603 (14)	0.94806 (19)	0.078 (2)
H53A	0.708277	0.237379	0.931015	0.117*
H53B	0.769826	0.277581	0.966045	0.117*
H53C	0.730086	0.038716	0.965832	0.117*
C62	0.6740 (3)	−0.0608 (11)	0.7688 (2)	0.082 (2)
H62A	0.712832	0.016923	0.782672	0.123*
H62B	0.684419	−0.175968	0.748270	0.123*
H62C	0.653998	−0.141636	0.790132	0.123*
C42	0.6292 (2)	0.1213 (10)	0.74637 (16)	0.0509 (14)
H42	0.588822	0.040486	0.734093	0.061*
C52	0.6568 (3)	0.2328 (14)	0.71050 (18)	0.079 (2)
H52A	0.626828	0.348235	0.695882	0.119*
H52B	0.664718	0.110181	0.690511	0.119*
H52C	0.696573	0.311858	0.721937	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.066 (2)	0.046 (2)	0.0279 (17)	−0.0026 (18)	−0.0041 (15)	0.0027 (16)
O21	0.0531 (19)	0.0402 (19)	0.0276 (16)	−0.0057 (17)	0.0011 (14)	0.0048 (15)
O31	0.063 (2)	0.051 (2)	0.0243 (16)	−0.0042 (19)	−0.0040 (15)	0.0059 (16)
O42	0.062 (2)	0.0328 (17)	0.0250 (16)	0.0030 (16)	0.0013 (14)	0.0014 (14)
O61	0.066 (2)	0.0335 (19)	0.0263 (16)	−0.0007 (17)	−0.0046 (15)	−0.0001 (14)
O52	0.083 (2)	0.046 (2)	0.0256 (17)	−0.0041 (19)	−0.0053 (16)	0.0046 (15)
O22	0.051 (2)	0.051 (2)	0.0384 (18)	0.0002 (18)	0.0169 (15)	−0.0089 (17)
N2	0.044 (2)	0.037 (2)	0.0267 (19)	−0.0025 (18)	0.0061 (16)	−0.0022 (17)
O12	0.061 (2)	0.061 (2)	0.049 (2)	−0.017 (2)	0.0155 (17)	−0.024 (2)
O53	0.064 (2)	0.050 (2)	0.0257 (17)	−0.0008 (18)	0.0022 (14)	0.0043 (15)
O33	0.074 (2)	0.0442 (19)	0.0283 (17)	0.0075 (19)	0.0118 (16)	0.0055 (16)
O62	0.073 (2)	0.0319 (17)	0.0246 (16)	0.0032 (17)	−0.0037 (16)	0.0001 (14)
O63	0.110 (3)	0.038 (2)	0.0257 (18)	0.010 (2)	0.002 (2)	−0.0013 (15)
N3	0.046 (2)	0.040 (2)	0.0251 (19)	0.0011 (19)	0.0075 (16)	−0.0002 (17)
O13	0.061 (2)	0.060 (2)	0.041 (2)	0.003 (2)	0.0010 (17)	0.0204 (18)
O32	0.074 (2)	0.048 (2)	0.0258 (17)	0.0003 (19)	−0.0048 (15)	−0.0042 (16)
O11	0.066 (2)	0.052 (2)	0.0299 (18)	−0.0157 (19)	−0.0117 (16)	0.0067 (16)
O41	0.060 (2)	0.0312 (16)	0.0319 (17)	0.0009 (16)	0.0009 (15)	0.0040 (14)
O23	0.055 (2)	0.058 (2)	0.044 (2)	−0.002 (2)	0.0157 (16)	0.0122 (19)
O43	0.146 (4)	0.0307 (19)	0.0312 (19)	0.013 (2)	0.018 (2)	0.0018 (16)
C92	0.073 (3)	0.030 (2)	0.031 (3)	0.006 (2)	0.006 (2)	0.004 (2)
C21	0.042 (2)	0.040 (3)	0.026 (2)	−0.002 (2)	0.0016 (18)	0.003 (2)
C102	0.053 (3)	0.034 (2)	0.029 (2)	−0.002 (2)	0.006 (2)	0.004 (2)
C91	0.067 (3)	0.031 (3)	0.032 (3)	0.000 (2)	−0.008 (2)	0.002 (2)
N1	0.049 (2)	0.038 (2)	0.0217 (18)	0.0030 (18)	0.0011 (16)	0.0053 (16)
C71	0.045 (3)	0.039 (3)	0.026 (2)	0.003 (2)	0.0030 (19)	0.005 (2)
C101	0.052 (3)	0.036 (3)	0.032 (3)	−0.001 (2)	0.001 (2)	0.003 (2)
C93	0.055 (3)	0.034 (2)	0.030 (2)	0.003 (2)	0.003 (2)	0.000 (2)
C12	0.052 (3)	0.034 (2)	0.026 (2)	−0.007 (2)	0.006 (2)	0.000 (2)
C22	0.040 (2)	0.034 (2)	0.024 (2)	−0.002 (2)	0.0040 (18)	−0.0018 (19)
C83	0.055 (3)	0.030 (2)	0.035 (3)	−0.001 (2)	0.006 (2)	−0.004 (2)
C73	0.056 (3)	0.036 (2)	0.029 (2)	0.000 (2)	0.001 (2)	0.002 (2)
C72	0.050 (3)	0.035 (3)	0.027 (2)	0.004 (2)	0.003 (2)	0.0001 (19)
C81	0.066 (3)	0.029 (2)	0.035 (3)	−0.003 (2)	−0.003 (2)	0.000 (2)
C103	0.049 (3)	0.037 (3)	0.033 (3)	0.005 (2)	0.004 (2)	0.000 (2)
C13	0.050 (3)	0.043 (3)	0.024 (2)	−0.001 (2)	0.010 (2)	0.003 (2)
C82	0.073 (3)	0.029 (2)	0.031 (3)	0.000 (2)	0.002 (2)	−0.001 (2)
C11	0.042 (2)	0.043 (3)	0.025 (2)	0.002 (2)	0.0063 (19)	−0.001 (2)
C32	0.042 (3)	0.049 (3)	0.033 (3)	−0.001 (2)	0.009 (2)	0.001 (2)
C43	0.045 (3)	0.061 (3)	0.051 (3)	0.008 (3)	0.017 (2)	0.018 (3)
C41	0.048 (3)	0.073 (4)	0.051 (3)	0.009 (3)	0.015 (2)	0.017 (3)
C23	0.046 (2)	0.038 (3)	0.023 (2)	−0.002 (2)	0.0019 (18)	−0.001 (2)
C61	0.064 (4)	0.107 (6)	0.106 (6)	0.009 (4)	0.043 (4)	0.021 (5)
C63	0.075 (4)	0.049 (3)	0.125 (6)	−0.013 (3)	0.044 (4)	−0.002 (4)
C33	0.042 (2)	0.042 (3)	0.030 (2)	0.000 (2)	0.0044 (19)	0.000 (2)
C31	0.053 (3)	0.055 (3)	0.030 (2)	0.007 (3)	0.014 (2)	0.009 (2)
C51	0.068 (4)	0.075 (5)	0.159 (8)	−0.021 (4)	0.026 (5)	−0.013 (5)
C53	0.074 (4)	0.104 (6)	0.063 (4)	−0.006 (4)	0.035 (3)	0.004 (4)
C62	0.110 (5)	0.051 (4)	0.102 (5)	0.010 (4)	0.064 (4)	0.001 (4)
C42	0.057 (3)	0.056 (3)	0.044 (3)	−0.011 (3)	0.022 (2)	−0.016 (3)
C52	0.093 (4)	0.111 (6)	0.042 (3)	0.008 (4)	0.035 (3)	0.004 (4)

Geometric parameters (Å, º) top

O51—C101	1.235 (5)	C93—C103	1.492 (6)
O21—C11	1.215 (5)	C12—C22	1.509 (6)
O31—C71	1.246 (5)	C22—H22	1.0000
O42—C72	1.290 (5)	C22—C32	1.526 (6)
O61—H61	0.8400	C83—H83	0.9500
O61—C101	1.287 (6)	C83—C73	1.495 (7)
O52—C102	1.240 (5)	C72—C82	1.491 (6)
O22—C12	1.202 (5)	C81—H81	0.9500
N2—H2A	0.9100	C13—C23	1.513 (6)
N2—H2B	0.9100	C82—H82	0.9500
N2—H2C	0.9100	C32—H32A	0.9900
N2—C22	1.497 (5)	C32—H32B	0.9900
O12—H12	0.8400	C32—C42	1.518 (7)
O12—C12	1.314 (5)	C43—H43	1.0000
O53—C103	1.229 (5)	C43—C63	1.521 (8)
O33—C73	1.232 (5)	C43—C33	1.520 (7)
O62—H62	0.8400	C43—C53	1.520 (8)
O62—C102	1.288 (6)	C41—H41	1.0000
O63—H63	0.8400	C41—C61	1.533 (8)
O63—C103	1.281 (6)	C41—C31	1.517 (7)
N3—H3A	0.9100	C41—C51	1.516 (10)
N3—H3B	0.9100	C23—H23	1.0000
N3—H3C	0.9100	C23—C33	1.530 (6)
N3—C23	1.496 (5)	C61—H61A	0.9800
O13—H13	0.8400	C61—H61B	0.9800
O13—C13	1.328 (5)	C61—H61C	0.9800
O32—C72	1.238 (5)	C63—H63A	0.9800
O11—H11	0.8400	C63—H63B	0.9800
O11—C11	1.320 (5)	C63—H63C	0.9800
O41—C71	1.285 (6)	C33—H33A	0.9900
O23—C13	1.200 (5)	C33—H33B	0.9900
O43—C73	1.284 (6)	C31—H31A	0.9900
C92—H92	0.9500	C31—H31B	0.9900
C92—C102	1.484 (7)	C51—H51A	0.9800
C92—C82	1.336 (6)	C51—H51B	0.9800
C21—H21	1.0000	C51—H51C	0.9800
C21—N1	1.490 (5)	C53—H53A	0.9800
C21—C11	1.518 (6)	C53—H53B	0.9800
C21—C31	1.521 (6)	C53—H53C	0.9800
C91—H91	0.9500	C62—H62A	0.9800
C91—C101	1.493 (6)	C62—H62B	0.9800
C91—C81	1.335 (6)	C62—H62C	0.9800
N1—H1A	0.9100	C62—C42	1.511 (8)
N1—H1B	0.9100	C42—H42	1.0000
N1—H1C	0.9100	C42—C52	1.517 (8)
C71—C81	1.480 (6)	C52—H52A	0.9800
C93—H93	0.9500	C52—H52B	0.9800
C93—C83	1.339 (6)	C52—H52C	0.9800

C101—O61—H61	109.5	O11—C11—C21	112.4 (4)
H2A—N2—H2B	109.5	C22—C32—H32A	108.2
H2A—N2—H2C	109.5	C22—C32—H32B	108.2
H2B—N2—H2C	109.5	H32A—C32—H32B	107.4
C22—N2—H2A	109.5	C42—C32—C22	116.3 (4)
C22—N2—H2B	109.5	C42—C32—H32A	108.2
C22—N2—H2C	109.5	C42—C32—H32B	108.2
C12—O12—H12	109.5	C63—C43—H43	108.4
C102—O62—H62	109.5	C33—C43—H43	108.4
C103—O63—H63	109.5	C33—C43—C63	112.2 (5)
H3A—N3—H3B	109.5	C53—C43—H43	108.4
H3A—N3—H3C	109.5	C53—C43—C63	110.8 (5)
H3B—N3—H3C	109.5	C53—C43—C33	108.4 (5)
C23—N3—H3A	109.5	C61—C41—H41	107.9
C23—N3—H3B	109.5	C31—C41—H41	107.9
C23—N3—H3C	109.5	C31—C41—C61	110.1 (5)
C13—O13—H13	109.5	C51—C41—H41	107.9
C11—O11—H11	109.5	C51—C41—C61	110.8 (6)
C102—C92—H92	114.8	C51—C41—C31	112.0 (5)
C82—C92—H92	114.8	N3—C23—C13	106.7 (4)
C82—C92—C102	130.4 (5)	N3—C23—H23	108.7
N1—C21—H21	109.9	N3—C23—C33	111.3 (3)
N1—C21—C11	106.7 (4)	C13—C23—H23	108.7
N1—C21—C31	108.8 (3)	C13—C23—C33	112.5 (4)
C11—C21—H21	109.9	C33—C23—H23	108.7
C11—C21—C31	111.8 (4)	C41—C61—H61A	109.5
C31—C21—H21	109.9	C41—C61—H61B	109.5
O52—C102—O62	120.8 (4)	C41—C61—H61C	109.5
O52—C102—C92	118.2 (4)	H61A—C61—H61B	109.5
O62—C102—C92	121.0 (4)	H61A—C61—H61C	109.5
C101—C91—H91	114.6	H61B—C61—H61C	109.5
C81—C91—H91	114.6	C43—C63—H63A	109.5
C81—C91—C101	130.7 (4)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—C23	116.1 (4)
H1B—N1—H1C	109.5	C43—C33—H33A	108.3
O31—C71—O41	122.2 (4)	C43—C33—H33B	108.3
O31—C71—C81	116.5 (4)	C23—C33—H33A	108.3
O41—C71—C81	121.3 (4)	C23—C33—H33B	108.3
O51—C101—O61	121.6 (4)	H33A—C33—H33B	107.4
O51—C101—C91	118.5 (4)	C21—C31—H31A	108.2
O61—C101—C91	119.9 (4)	C21—C31—H31B	108.2
C83—C93—H93	114.5	C41—C31—C21	116.4 (4)
C83—C93—C103	131.0 (4)	C41—C31—H31A	108.2
C103—C93—H93	114.5	C41—C31—H31B	108.2
O22—C12—O12	124.5 (4)	H31A—C31—H31B	107.3
O22—C12—C22	122.0 (4)	C41—C51—H51A	109.5
O12—C12—C22	113.5 (4)	C41—C51—H51B	109.5
N2—C22—C12	105.8 (4)	C41—C51—H51C	109.5
N2—C22—H22	107.9	H51A—C51—H51B	109.5
N2—C22—C32	111.7 (3)	H51A—C51—H51C	109.5
C12—C22—H22	107.9	H51B—C51—H51C	109.5
C12—C22—C32	115.5 (4)	C43—C53—H53A	109.5
C32—C22—H22	107.9	C43—C53—H53B	109.5
C93—C83—H83	115.2	C43—C53—H53C	109.5
C93—C83—C73	129.5 (4)	H53A—C53—H53B	109.5
C73—C83—H83	115.2	H53A—C53—H53C	109.5
O33—C73—O43	122.0 (5)	H53B—C53—H53C	109.5
O33—C73—C83	117.8 (4)	H62A—C62—H62B	109.5
O43—C73—C83	120.2 (4)	H62A—C62—H62C	109.5
O42—C72—C82	119.3 (4)	H62B—C62—H62C	109.5
O32—C72—O42	122.5 (4)	C42—C62—H62A	109.5
O32—C72—C82	118.2 (4)	C42—C62—H62B	109.5
C91—C81—C71	130.1 (4)	C42—C62—H62C	109.5
C91—C81—H81	115.0	C32—C42—H42	108.3
C71—C81—H81	115.0	C62—C42—C32	112.0 (5)
O53—C103—O63	121.6 (5)	C62—C42—H42	108.3
O53—C103—C93	119.1 (4)	C62—C42—C52	110.4 (5)
O63—C103—C93	119.4 (4)	C52—C42—C32	109.4 (5)
O13—C13—C23	111.6 (4)	C52—C42—H42	108.3
O23—C13—O13	124.6 (4)	C42—C52—H52A	109.5
O23—C13—C23	123.8 (4)	C42—C52—H52B	109.5
C92—C82—C72	131.0 (5)	C42—C52—H52C	109.5
C92—C82—H82	114.5	H52A—C52—H52B	109.5
C72—C82—H82	114.5	H52A—C52—H52C	109.5
O21—C11—O11	125.0 (4)	H52B—C52—H52C	109.5
O21—C11—C21	122.5 (4)

O31—C71—C81—C91	179.5 (5)	C93—C83—C73—O43	13.2 (8)
O42—C72—C82—C92	−4.1 (9)	C12—C22—C32—C42	178.5 (4)
O22—C12—C22—N2	17.2 (6)	C22—C32—C42—C62	−69.5 (6)
O22—C12—C22—C32	141.3 (4)	C22—C32—C42—C52	167.9 (4)
N2—C22—C32—C42	−60.6 (5)	C83—C93—C103—O53	173.9 (5)
O12—C12—C22—N2	−164.3 (4)	C83—C93—C103—O63	−5.6 (8)
O12—C12—C22—C32	−40.2 (6)	C81—C91—C101—O51	178.4 (6)
N3—C23—C33—C43	−60.6 (5)	C81—C91—C101—O61	−0.4 (9)
O13—C13—C23—N3	−173.3 (4)	C103—C93—C83—C73	−2.4 (9)
O13—C13—C23—C33	−50.9 (5)	C13—C23—C33—C43	179.7 (4)
O32—C72—C82—C92	176.4 (5)	C82—C92—C102—O52	−178.8 (5)
O41—C71—C81—C91	−0.1 (9)	C82—C92—C102—O62	1.5 (9)
O23—C13—C23—N3	6.5 (6)	C11—C21—C31—C41	68.2 (6)
O23—C13—C23—C33	128.8 (5)	C61—C41—C31—C21	−175.5 (5)
C102—C92—C82—C72	−0.4 (10)	C63—C43—C33—C23	−70.1 (5)
N1—C21—C11—O21	−27.4 (6)	C31—C21—C11—O21	91.4 (5)
N1—C21—C11—O11	155.2 (4)	C31—C21—C11—O11	−86.1 (5)
N1—C21—C31—C41	−174.3 (4)	C51—C41—C31—C21	60.6 (7)
C101—C91—C81—C71	0.9 (10)	C53—C43—C33—C23	167.2 (4)
C93—C83—C73—O33	−168.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.84	1.59	2.425 (4)	174
N2—H2A···O61ⁱ	0.91	2.02	2.901 (4)	161
N2—H2B···O23ⁱⁱ	0.91	2.03	2.860 (5)	151
N2—H2C···O51ⁱⁱⁱ	0.91	1.88	2.766 (5)	163
O12—H12···O33^iv	0.84	1.79	2.598 (5)	161
O62—H62···O42	0.84	1.60	2.437 (4)	174
O63—H63···O43	0.84	1.58	2.421 (5)	179
N3—H3A···O22^v	0.91	1.93	2.787 (5)	156
N3—H3B···O53^vi	0.91	1.92	2.823 (5)	171
N3—H3C···O63^vii	0.91	2.01	2.867 (5)	157
O13—H13···O52^viii	0.84	1.77	2.598 (5)	170
O11—H11···O31	0.84	1.76	2.594 (4)	173
N1—H1A···O21^ix	0.91	2.14	2.881 (5)	138
N1—H1A···O31^ix	0.91	2.41	2.994 (5)	122
N1—H1B···O42^v	0.91	1.95	2.861 (4)	176
N1—H1C···O32^viii	0.91	1.97	2.865 (5)	166

L-Leucinium hydrogen maleate (l_leu_mal_225) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.276 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.5229 (9) Å	Cell parameters from 4556 reflections
b = 5.6692 (2) Å	θ = 1.9–28.9°
c = 32.0754 (9) Å	µ = 0.11 mm⁻¹
β = 99.486 (4)°	T = 225 K
V = 3860.3 (2) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7652 independent reflections
Radiation source: fine-focus sealed X-ray tube	4758 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.874, T_max = 1.000	k = −7→6
22927 measured reflections	l = −40→40

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.143	w = 1/[σ²(F_o²) + (0.0473P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
7652 reflections	Δρ_max = 0.19 e Å⁻³
475 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint

Special details top

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

	x	y	z	U_iso*/U_eq
O51	0.50188 (17)	0.7017 (7)	0.24628 (10)	0.0548 (10)
O21	0.70328 (15)	0.5500 (6)	0.50318 (10)	0.0463 (8)
O31	0.61307 (16)	0.5842 (7)	0.41807 (10)	0.0524 (9)
O42	0.27944 (16)	0.5347 (6)	0.64738 (10)	0.0458 (9)
O61	0.53281 (17)	0.4085 (6)	0.28955 (10)	0.0493 (9)
H61	0.547478	0.389721	0.314933	0.074*
O52	0.35263 (19)	0.3399 (7)	0.77610 (11)	0.0607 (11)
O22	0.50932 (16)	0.4513 (7)	0.85008 (10)	0.0517 (9)
N2	0.50907 (17)	0.1517 (7)	0.78827 (11)	0.0408 (9)
H2A	0.491416	0.255661	0.768630	0.049*
H2B	0.484364	0.135216	0.808155	0.049*
H2C	0.513280	0.011258	0.775952	0.049*
O12	0.60884 (17)	0.5648 (8)	0.85165 (12)	0.0630 (11)
H12	0.600513	0.657940	0.869915	0.095*
O53	0.41487 (17)	0.1512 (6)	−0.06532 (10)	0.0514 (9)
O33	0.41418 (17)	−0.0604 (7)	0.10697 (10)	0.0561 (10)
O62	0.32552 (18)	0.5743 (6)	0.72164 (10)	0.0500 (9)
H62	0.308295	0.564651	0.696571	0.075*
O63	0.4263 (2)	−0.1588 (6)	−0.02423 (11)	0.0663 (12)
H63	0.424296	−0.190451	0.000779	0.099*
N3	0.91828 (17)	0.0992 (7)	0.89676 (11)	0.0402 (9)
H3A	0.950812	0.091003	0.882424	0.048*
H3B	0.912214	−0.042916	0.907932	0.048*
H3C	0.926838	0.206330	0.917617	0.048*
O13	0.82808 (17)	0.4637 (8)	0.81655 (12)	0.0630 (11)
H13	0.839194	0.572528	0.802097	0.095*
O32	0.25410 (18)	0.2455 (7)	0.60115 (10)	0.0560 (10)
O11	0.64244 (18)	0.2528 (7)	0.47367 (10)	0.0572 (10)
H11	0.632990	0.348288	0.454028	0.086*
O41	0.58036 (17)	0.3557 (6)	0.36286 (10)	0.0477 (9)
O23	0.93140 (17)	0.4379 (7)	0.84176 (11)	0.0576 (10)
O43	0.4306 (2)	−0.2496 (7)	0.04993 (12)	0.0788 (14)
C92	0.3114 (3)	0.1542 (9)	0.71242 (15)	0.0483 (13)
H92	0.316429	0.010923	0.727351	0.058*
C21	0.6933 (2)	0.2033 (9)	0.54398 (13)	0.0401 (11)
H21	0.695053	0.035205	0.535910	0.048*
C102	0.3309 (2)	0.3660 (9)	0.73819 (15)	0.0440 (12)
C91	0.5459 (3)	0.8076 (8)	0.31566 (15)	0.0500 (14)
H91	0.539206	0.965628	0.307244	0.060*
N1	0.75529 (17)	0.2772 (7)	0.56780 (11)	0.0418 (10)
H1A	0.785556	0.247629	0.552210	0.050*
H1B	0.763433	0.196086	0.592215	0.050*
H1C	0.754463	0.432580	0.573417	0.050*
C71	0.5893 (2)	0.5600 (9)	0.38044 (15)	0.0432 (12)
C101	0.5258 (2)	0.6308 (9)	0.28155 (15)	0.0440 (12)
C93	0.4222 (2)	0.2231 (9)	0.00727 (14)	0.0433 (12)
H93	0.422099	0.384938	0.000878	0.052*
C12	0.5596 (2)	0.4315 (9)	0.83868 (14)	0.0417 (11)
C22	0.5727 (2)	0.2399 (9)	0.80841 (13)	0.0361 (10)
H22	0.594681	0.109472	0.825308	0.043*
C83	0.4235 (2)	0.1739 (9)	0.04832 (15)	0.0430 (12)
H83	0.425301	0.305883	0.066210	0.052*
C73	0.4225 (2)	−0.0581 (10)	0.06969 (15)	0.0469 (12)
C72	0.2732 (2)	0.3141 (9)	0.63771 (15)	0.0441 (12)
C81	0.5717 (2)	0.7782 (9)	0.35605 (15)	0.0486 (13)
H81	0.579972	0.918756	0.371518	0.058*
C103	0.4209 (2)	0.0642 (9)	−0.02992 (15)	0.0441 (12)
C13	0.8785 (3)	0.3718 (9)	0.84065 (14)	0.0442 (12)
C82	0.2879 (3)	0.1334 (9)	0.67166 (15)	0.0515 (14)
H82	0.279024	−0.022449	0.662615	0.062*
C11	0.6812 (2)	0.3542 (10)	0.50467 (14)	0.0422 (11)
C32	0.6127 (2)	0.3135 (9)	0.77588 (15)	0.0446 (12)
H32A	0.590863	0.441434	0.758837	0.053*
H32B	0.652444	0.377606	0.790873	0.053*
C43	0.7851 (3)	0.0464 (12)	0.91895 (18)	0.0608 (16)
H43	0.822612	−0.025281	0.936389	0.073*
C41	0.5779 (2)	0.1471 (12)	0.5543 (2)	0.0634 (16)
H41	0.563766	0.226756	0.526912	0.076*
C23	0.8601 (2)	0.1708 (9)	0.86736 (14)	0.0396 (11)
H23	0.845895	0.036167	0.848542	0.048*
C61	0.5319 (3)	0.2129 (17)	0.5840 (2)	0.101 (3)
H61A	0.544524	0.135842	0.611084	0.152*
H61B	0.489798	0.162080	0.571784	0.152*
H61C	0.532200	0.382523	0.588012	0.152*
C63	0.7491 (3)	−0.1463 (12)	0.8923 (3)	0.096 (3)
H63A	0.713810	−0.077188	0.873525	0.144*
H63B	0.733556	−0.260465	0.910617	0.144*
H63C	0.776817	−0.224357	0.875674	0.144*
C33	0.8072 (2)	0.2368 (9)	0.89163 (14)	0.0430 (12)
H33A	0.821240	0.372189	0.909740	0.052*
H33B	0.770874	0.288589	0.871118	0.052*
C31	0.6431 (2)	0.2368 (11)	0.57168 (15)	0.0501 (13)
H31A	0.657459	0.158044	0.598750	0.060*
H31B	0.640028	0.405726	0.577507	0.060*
C51	0.5769 (3)	−0.1158 (14)	0.5463 (3)	0.111 (3)
H51A	0.597490	−0.196796	0.571461	0.167*
H51B	0.598965	−0.150091	0.522945	0.167*
H51C	0.533627	−0.169245	0.539328	0.167*
C53	0.7452 (3)	0.1605 (16)	0.9483 (2)	0.091 (2)
H53A	0.709460	0.239445	0.931678	0.136*
H53B	0.770365	0.274603	0.966258	0.136*
H53C	0.730216	0.040141	0.965741	0.136*
C62	0.6728 (3)	−0.0583 (13)	0.7685 (2)	0.096 (2)
H62A	0.711018	0.019635	0.781930	0.144*
H62B	0.683021	−0.172281	0.748096	0.144*
H62C	0.653369	−0.138565	0.789740	0.144*
C42	0.6278 (3)	0.1222 (11)	0.74626 (17)	0.0594 (16)
H42	0.588104	0.041218	0.734255	0.071*
C52	0.6555 (3)	0.2330 (16)	0.7101 (2)	0.093 (2)
H52A	0.626467	0.350076	0.696037	0.139*
H52B	0.662315	0.111606	0.690033	0.139*
H52C	0.695291	0.307954	0.721213	0.139*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.078 (2)	0.054 (2)	0.0284 (18)	0.000 (2)	−0.0058 (16)	0.0052 (17)
O21	0.060 (2)	0.047 (2)	0.0303 (18)	−0.0090 (18)	0.0007 (15)	0.0055 (16)
O31	0.071 (2)	0.055 (2)	0.0264 (18)	−0.004 (2)	−0.0061 (16)	0.0059 (16)
O42	0.071 (2)	0.0364 (19)	0.0286 (17)	0.0048 (17)	0.0026 (16)	0.0029 (15)
O61	0.075 (2)	0.037 (2)	0.0311 (18)	0.0003 (18)	−0.0056 (17)	−0.0002 (15)
O52	0.094 (3)	0.051 (2)	0.0307 (19)	−0.006 (2)	−0.0082 (18)	0.0053 (17)
O22	0.058 (2)	0.056 (2)	0.044 (2)	−0.0001 (19)	0.0202 (17)	−0.0114 (18)
N2	0.050 (2)	0.042 (2)	0.031 (2)	0.001 (2)	0.0067 (17)	−0.0006 (18)
O12	0.070 (2)	0.068 (3)	0.054 (2)	−0.020 (2)	0.0187 (19)	−0.030 (2)
O53	0.071 (2)	0.055 (2)	0.0277 (18)	−0.0012 (19)	0.0050 (16)	0.0057 (17)
O33	0.086 (3)	0.050 (2)	0.0321 (19)	0.008 (2)	0.0109 (18)	0.0063 (18)
O62	0.081 (3)	0.0372 (19)	0.0274 (18)	0.0033 (19)	−0.0036 (17)	0.0005 (15)
O63	0.126 (4)	0.043 (2)	0.0270 (19)	0.006 (2)	0.004 (2)	−0.0014 (17)
N3	0.051 (2)	0.044 (2)	0.027 (2)	0.002 (2)	0.0093 (17)	−0.0005 (17)
O13	0.072 (2)	0.069 (3)	0.045 (2)	0.000 (2)	0.0021 (19)	0.024 (2)
O32	0.086 (3)	0.047 (2)	0.0299 (18)	0.003 (2)	−0.0061 (17)	−0.0022 (17)
O11	0.077 (2)	0.058 (2)	0.0303 (19)	−0.020 (2)	−0.0109 (18)	0.0064 (18)
O41	0.068 (2)	0.0354 (18)	0.0367 (19)	−0.0010 (17)	−0.0013 (16)	0.0059 (15)
O23	0.059 (2)	0.063 (3)	0.053 (2)	−0.005 (2)	0.0163 (18)	0.015 (2)
O43	0.165 (4)	0.034 (2)	0.038 (2)	0.013 (3)	0.020 (2)	0.0026 (18)
C92	0.078 (4)	0.032 (3)	0.033 (3)	0.004 (3)	0.004 (2)	0.003 (2)
C21	0.048 (3)	0.043 (3)	0.028 (2)	0.002 (2)	0.002 (2)	0.001 (2)
C102	0.060 (3)	0.039 (3)	0.031 (3)	0.005 (3)	0.003 (2)	0.004 (2)
C91	0.077 (4)	0.030 (3)	0.038 (3)	0.003 (3)	−0.008 (3)	0.000 (2)
N1	0.055 (2)	0.043 (2)	0.026 (2)	0.004 (2)	0.0013 (17)	0.0055 (18)
C71	0.054 (3)	0.042 (3)	0.032 (3)	0.001 (3)	0.001 (2)	0.002 (2)
C101	0.058 (3)	0.038 (3)	0.034 (3)	−0.001 (2)	0.000 (2)	0.003 (2)
C93	0.063 (3)	0.035 (3)	0.032 (3)	0.004 (2)	0.006 (2)	0.003 (2)
C12	0.060 (3)	0.040 (3)	0.024 (2)	−0.003 (3)	0.005 (2)	−0.001 (2)
C22	0.044 (2)	0.037 (2)	0.027 (2)	−0.004 (2)	0.0067 (19)	−0.002 (2)
C83	0.062 (3)	0.031 (2)	0.035 (3)	0.001 (2)	0.005 (2)	−0.004 (2)
C73	0.066 (3)	0.040 (3)	0.032 (3)	0.005 (3)	0.001 (2)	0.002 (2)
C72	0.060 (3)	0.040 (3)	0.030 (3)	0.003 (2)	0.002 (2)	0.000 (2)
C81	0.073 (3)	0.032 (3)	0.035 (3)	0.004 (3)	−0.006 (2)	−0.002 (2)
C103	0.058 (3)	0.038 (3)	0.035 (3)	0.001 (3)	0.004 (2)	0.000 (2)
C13	0.063 (3)	0.045 (3)	0.026 (2)	0.000 (3)	0.011 (2)	0.003 (2)
C82	0.082 (4)	0.035 (3)	0.035 (3)	−0.002 (3)	0.003 (3)	−0.002 (2)
C11	0.046 (3)	0.051 (3)	0.028 (2)	0.001 (3)	0.004 (2)	0.003 (2)
C32	0.048 (3)	0.052 (3)	0.036 (3)	−0.001 (2)	0.011 (2)	−0.001 (2)
C43	0.056 (3)	0.072 (4)	0.058 (4)	0.007 (3)	0.019 (3)	0.023 (3)
C41	0.049 (3)	0.077 (4)	0.066 (4)	0.009 (3)	0.013 (3)	0.021 (3)
C23	0.051 (3)	0.040 (3)	0.027 (2)	0.002 (2)	0.004 (2)	0.002 (2)
C61	0.074 (4)	0.127 (7)	0.114 (6)	0.013 (5)	0.049 (4)	0.027 (6)
C63	0.087 (5)	0.058 (4)	0.154 (8)	−0.021 (4)	0.053 (5)	−0.006 (5)
C33	0.049 (3)	0.047 (3)	0.033 (3)	−0.003 (2)	0.006 (2)	0.000 (2)
C31	0.059 (3)	0.057 (3)	0.037 (3)	0.009 (3)	0.015 (2)	0.010 (3)
C51	0.079 (5)	0.083 (6)	0.170 (9)	−0.024 (4)	0.020 (5)	−0.010 (6)
C53	0.083 (4)	0.128 (7)	0.072 (5)	−0.003 (5)	0.041 (4)	0.007 (5)
C62	0.118 (6)	0.062 (4)	0.127 (6)	0.015 (5)	0.075 (5)	0.003 (5)
C42	0.064 (3)	0.067 (4)	0.053 (3)	−0.013 (3)	0.027 (3)	−0.021 (3)
C52	0.104 (5)	0.133 (7)	0.052 (4)	0.009 (5)	0.043 (4)	0.004 (5)

Geometric parameters (Å, º) top

O51—C101	1.231 (5)	C93—C103	1.491 (7)
O21—C11	1.212 (6)	C12—C22	1.514 (7)
O31—C71	1.239 (5)	C22—H22	0.9900
O42—C72	1.290 (6)	C22—C32	1.517 (6)
O61—H61	0.8300	C83—H83	0.9400
O61—C101	1.290 (6)	C83—C73	1.485 (7)
O52—C102	1.237 (5)	C72—C82	1.491 (7)
O22—C12	1.204 (5)	C81—H81	0.9400
N2—H2A	0.9000	C13—C23	1.516 (7)
N2—H2B	0.9000	C82—H82	0.9400
N2—H2C	0.9000	C32—H32A	0.9800
N2—C22	1.500 (5)	C32—H32B	0.9800
O12—H12	0.8300	C32—C42	1.512 (7)
O12—C12	1.312 (6)	C43—H43	0.9900
O53—C103	1.225 (6)	C43—C63	1.520 (9)
O33—C73	1.238 (6)	C43—C33	1.515 (7)
O62—H62	0.8300	C43—C53	1.521 (8)
O62—C102	1.292 (6)	C41—H41	0.9900
O63—H63	0.8300	C41—C61	1.530 (9)
O63—C103	1.280 (6)	C41—C31	1.510 (7)
N3—H3A	0.9000	C41—C51	1.512 (10)
N3—H3B	0.9000	C23—H23	0.9900
N3—H3C	0.9000	C23—C33	1.528 (6)
N3—C23	1.494 (5)	C61—H61A	0.9700
O13—H13	0.8300	C61—H61B	0.9700
O13—C13	1.330 (6)	C61—H61C	0.9700
O32—C72	1.240 (5)	C63—H63A	0.9700
O11—H11	0.8300	C63—H63B	0.9700
O11—C11	1.319 (6)	C63—H63C	0.9700
O41—C71	1.288 (6)	C33—H33A	0.9800
O23—C13	1.194 (6)	C33—H33B	0.9800
O43—C73	1.284 (6)	C31—H31A	0.9800
C92—H92	0.9400	C31—H31B	0.9800
C92—C102	1.479 (7)	C51—H51A	0.9700
C92—C82	1.327 (7)	C51—H51B	0.9700
C21—H21	0.9900	C51—H51C	0.9700
C21—N1	1.485 (6)	C53—H53A	0.9700
C21—C11	1.510 (6)	C53—H53B	0.9700
C21—C31	1.518 (6)	C53—H53C	0.9700
C91—H91	0.9400	C62—H62A	0.9700
C91—C101	1.494 (7)	C62—H62B	0.9700
C91—C81	1.333 (6)	C62—H62C	0.9700
N1—H1A	0.9000	C62—C42	1.505 (9)
N1—H1B	0.9000	C42—H42	0.9900
N1—H1C	0.9000	C42—C52	1.524 (8)
C71—C81	1.480 (7)	C52—H52A	0.9700
C93—H93	0.9400	C52—H52B	0.9700
C93—C83	1.342 (6)	C52—H52C	0.9700

C101—O61—H61	109.5	O11—C11—C21	112.5 (4)
H2A—N2—H2B	109.5	C22—C32—H32A	108.3
H2A—N2—H2C	109.5	C22—C32—H32B	108.3
H2B—N2—H2C	109.5	H32A—C32—H32B	107.4
C22—N2—H2A	109.5	C42—C32—C22	116.1 (4)
C22—N2—H2B	109.5	C42—C32—H32A	108.3
C22—N2—H2C	109.5	C42—C32—H32B	108.3
C12—O12—H12	109.5	C63—C43—H43	108.4
C102—O62—H62	109.5	C63—C43—C53	111.5 (5)
C103—O63—H63	109.5	C33—C43—H43	108.4
H3A—N3—H3B	109.5	C33—C43—C63	111.5 (5)
H3A—N3—H3C	109.5	C33—C43—C53	108.6 (5)
H3B—N3—H3C	109.5	C53—C43—H43	108.4
C23—N3—H3A	109.5	C61—C41—H41	107.8
C23—N3—H3B	109.5	C31—C41—H41	107.8
C23—N3—H3C	109.5	C31—C41—C61	110.2 (6)
C13—O13—H13	109.5	C31—C41—C51	112.4 (5)
C11—O11—H11	109.5	C51—C41—H41	107.8
C102—C92—H92	114.7	C51—C41—C61	110.7 (7)
C82—C92—H92	114.7	N3—C23—C13	107.0 (4)
C82—C92—C102	130.5 (5)	N3—C23—H23	108.5
N1—C21—H21	109.6	N3—C23—C33	111.3 (4)
N1—C21—C11	106.7 (4)	C13—C23—H23	108.5
N1—C21—C31	109.2 (4)	C13—C23—C33	112.9 (4)
C11—C21—H21	109.6	C33—C23—H23	108.5
C11—C21—C31	112.1 (4)	C41—C61—H61A	109.5
C31—C21—H21	109.6	C41—C61—H61B	109.5
O52—C102—O62	120.4 (5)	C41—C61—H61C	109.5
O52—C102—C92	118.6 (5)	H61A—C61—H61B	109.5
O62—C102—C92	121.0 (4)	H61A—C61—H61C	109.5
C101—C91—H91	114.7	H61B—C61—H61C	109.5
C81—C91—H91	114.7	C43—C63—H63A	109.5
C81—C91—C101	130.7 (5)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—C23	116.8 (4)
H1B—N1—H1C	109.5	C43—C33—H33A	108.1
O31—C71—O41	122.3 (5)	C43—C33—H33B	108.1
O31—C71—C81	116.8 (5)	C23—C33—H33A	108.1
O41—C71—C81	120.9 (4)	C23—C33—H33B	108.1
O51—C101—O61	121.3 (4)	H33A—C33—H33B	107.3
O51—C101—C91	118.7 (4)	C21—C31—H31A	108.1
O61—C101—C91	120.0 (4)	C21—C31—H31B	108.1
C83—C93—H93	114.6	C41—C31—C21	116.7 (5)
C83—C93—C103	130.8 (5)	C41—C31—H31A	108.1
C103—C93—H93	114.6	C41—C31—H31B	108.1
O22—C12—O12	124.7 (5)	H31A—C31—H31B	107.3
O22—C12—C22	122.2 (4)	C41—C51—H51A	109.5
O12—C12—C22	113.0 (4)	C41—C51—H51B	109.5
N2—C22—C12	105.2 (4)	C41—C51—H51C	109.5
N2—C22—H22	107.9	H51A—C51—H51B	109.5
N2—C22—C32	112.1 (4)	H51A—C51—H51C	109.5
C12—C22—H22	107.9	H51B—C51—H51C	109.5
C12—C22—C32	115.5 (4)	C43—C53—H53A	109.5
C32—C22—H22	107.9	C43—C53—H53B	109.5
C93—C83—H83	115.2	C43—C53—H53C	109.5
C93—C83—C73	129.6 (5)	H53A—C53—H53B	109.5
C73—C83—H83	115.2	H53A—C53—H53C	109.5
O33—C73—O43	121.4 (5)	H53B—C53—H53C	109.5
O33—C73—C83	118.1 (5)	H62A—C62—H62B	109.5
O43—C73—C83	120.5 (4)	H62A—C62—H62C	109.5
O42—C72—C82	119.3 (4)	H62B—C62—H62C	109.5
O32—C72—O42	122.5 (5)	C42—C62—H62A	109.5
O32—C72—C82	118.2 (5)	C42—C62—H62B	109.5
C91—C81—C71	130.4 (5)	C42—C62—H62C	109.5
C91—C81—H81	114.8	C32—C42—H42	108.4
C71—C81—H81	114.8	C32—C42—C52	109.5 (5)
O53—C103—O63	121.5 (5)	C62—C42—C32	112.2 (5)
O53—C103—C93	118.9 (5)	C62—C42—H42	108.4
O63—C103—C93	119.6 (4)	C62—C42—C52	109.8 (5)
O13—C13—C23	111.1 (4)	C52—C42—H42	108.4
O23—C13—O13	125.2 (5)	C42—C52—H52A	109.5
O23—C13—C23	123.7 (5)	C42—C52—H52B	109.5
C92—C82—C72	131.3 (5)	C42—C52—H52C	109.5
C92—C82—H82	114.4	H52A—C52—H52B	109.5
C72—C82—H82	114.4	H52A—C52—H52C	109.5
O21—C11—O11	124.9 (4)	H52B—C52—H52C	109.5
O21—C11—C21	122.5 (4)

O31—C71—C81—C91	179.7 (6)	C93—C83—C73—O43	11.7 (9)
O42—C72—C82—C92	−4.9 (10)	C12—C22—C32—C42	178.2 (4)
O22—C12—C22—N2	16.9 (6)	C22—C32—C42—C62	−69.9 (6)
O22—C12—C22—C32	141.2 (5)	C22—C32—C42—C52	167.9 (5)
N2—C22—C32—C42	−61.3 (6)	C83—C93—C103—O53	174.4 (5)
O12—C12—C22—N2	−165.0 (4)	C83—C93—C103—O63	−5.9 (9)
O12—C12—C22—C32	−40.8 (6)	C81—C91—C101—O51	178.9 (6)
N3—C23—C33—C43	−60.3 (6)	C81—C91—C101—O61	−0.1 (10)
O13—C13—C23—N3	−173.4 (4)	C103—C93—C83—C73	−1.6 (9)
O13—C13—C23—C33	−50.7 (6)	C13—C23—C33—C43	179.5 (4)
O32—C72—C82—C92	176.5 (6)	C82—C92—C102—O52	−179.0 (6)
O41—C71—C81—C91	0.1 (10)	C82—C92—C102—O62	1.1 (10)
O23—C13—C23—N3	6.0 (7)	C11—C21—C31—C41	68.2 (6)
O23—C13—C23—C33	128.7 (5)	C61—C41—C31—C21	−175.1 (5)
C102—C92—C82—C72	0.1 (11)	C63—C43—C33—C23	−70.8 (6)
N1—C21—C11—O21	−27.4 (6)	C31—C21—C11—O21	92.1 (6)
N1—C21—C11—O11	155.2 (4)	C31—C21—C11—O11	−85.3 (5)
N1—C21—C31—C41	−173.9 (5)	C51—C41—C31—C21	60.9 (8)
C101—C91—C81—C71	0.4 (11)	C53—C43—C33—C23	166.1 (5)
C93—C83—C73—O33	−169.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.83	1.59	2.423 (4)	176
N2—H2A···O61ⁱ	0.90	2.05	2.902 (5)	159
N2—H2B···O23ⁱⁱ	0.90	2.03	2.855 (5)	152
N2—H2C···O51ⁱⁱⁱ	0.90	1.90	2.776 (5)	163
O12—H12···O33^iv	0.83	1.81	2.596 (5)	157
O62—H62···O42	0.83	1.61	2.435 (4)	176
O63—H63···O43	0.83	1.60	2.421 (5)	172
N3—H3A···O22^v	0.90	1.93	2.784 (5)	158
N3—H3B···O53^vi	0.90	1.93	2.822 (5)	170
N3—H3C···O63^vii	0.90	2.02	2.862 (5)	156
O13—H13···O52^viii	0.83	1.78	2.596 (5)	169
O11—H11···O31	0.83	1.77	2.596 (5)	172
N1—H1A···O21^ix	0.90	2.15	2.882 (5)	138
N1—H1A···O31^ix	0.90	2.42	3.001 (5)	123
N1—H1B···O42^v	0.90	1.97	2.870 (5)	177
N1—H1C···O32^viii	0.90	1.98	2.864 (5)	165

L-Leucinium hydrogen maleate (l_leu_mal_250) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.270 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.6021 (9) Å	Cell parameters from 4292 reflections
b = 5.6701 (2) Å	θ = 1.9–25.6°
c = 32.0856 (9) Å	µ = 0.11 mm⁻¹
β = 99.299 (4)°	T = 250 K
V = 3878.4 (2) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7684 independent reflections
Radiation source: fine-focus sealed X-ray tube	4651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.643, T_max = 1.000	k = −7→6
23037 measured reflections	l = −40→40

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0524P)² + 0.2469P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
7684 reflections	Δρ_max = 0.17 e Å⁻³
475 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint

Special details top

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

	x	y	z	U_iso*/U_eq
O51	0.50303 (18)	0.7030 (7)	0.24685 (10)	0.0614 (10)
O21	0.70343 (16)	0.5486 (7)	0.50320 (10)	0.0519 (9)
O31	0.61386 (17)	0.5854 (7)	0.41824 (10)	0.0593 (10)
O42	0.27856 (17)	0.5332 (6)	0.64725 (10)	0.0515 (9)
O61	0.53352 (18)	0.4101 (6)	0.28999 (10)	0.0561 (10)
H61	0.549317	0.391373	0.315119	0.084*
O52	0.3518 (2)	0.3383 (7)	0.77577 (11)	0.0675 (11)
O22	0.50841 (17)	0.4525 (7)	0.84986 (11)	0.0578 (10)
N2	0.50803 (18)	0.1533 (7)	0.78789 (12)	0.0456 (10)
H2A	0.490857	0.256378	0.767999	0.055*
H2B	0.483140	0.139310	0.807704	0.055*
H2C	0.512062	0.011788	0.775908	0.055*
O12	0.60760 (18)	0.5639 (8)	0.85147 (13)	0.0722 (12)
H12	0.598899	0.660547	0.869064	0.108*
O53	0.41473 (18)	0.1514 (7)	−0.06496 (10)	0.0578 (10)
O33	0.41469 (18)	−0.0604 (7)	0.10716 (11)	0.0630 (10)
O62	0.32480 (19)	0.5727 (6)	0.72146 (11)	0.0545 (10)
H62	0.306728	0.563492	0.696637	0.082*
O63	0.4260 (2)	−0.1577 (7)	−0.02400 (11)	0.0745 (13)
H63	0.423944	−0.189100	0.001005	0.112*
N3	0.91816 (18)	0.1008 (8)	0.89682 (12)	0.0464 (10)
H3A	0.950471	0.093186	0.882339	0.056*
H3B	0.912454	−0.041175	0.908142	0.056*
H3C	0.926596	0.208556	0.917568	0.056*
O13	0.82776 (18)	0.4620 (8)	0.81654 (12)	0.0704 (11)
H13	0.838982	0.563707	0.800711	0.106*
O32	0.25363 (19)	0.2437 (7)	0.60131 (11)	0.0630 (11)
O11	0.6424 (2)	0.2529 (8)	0.47380 (11)	0.0650 (11)
H11	0.632204	0.349570	0.454484	0.097*
O41	0.58083 (18)	0.3567 (6)	0.36319 (11)	0.0541 (9)
O23	0.93056 (18)	0.4391 (8)	0.84174 (12)	0.0661 (11)
O43	0.4305 (3)	−0.2492 (7)	0.05015 (12)	0.0884 (16)
C92	0.3106 (3)	0.1526 (9)	0.71241 (15)	0.0540 (14)
H92	0.315077	0.009682	0.727450	0.065*
C21	0.6928 (2)	0.2004 (9)	0.54399 (14)	0.0440 (12)
H21	0.694582	0.032425	0.535854	0.053*
C102	0.3303 (2)	0.3648 (9)	0.73794 (15)	0.0483 (12)
C91	0.5467 (3)	0.8086 (9)	0.31619 (16)	0.0561 (15)
H91	0.539985	0.966689	0.307872	0.067*
N1	0.75458 (18)	0.2757 (7)	0.56788 (11)	0.0468 (10)
H1A	0.784899	0.245851	0.552383	0.056*
H1B	0.762562	0.195424	0.592361	0.056*
H1C	0.753610	0.431232	0.573325	0.056*
C71	0.5898 (2)	0.5601 (10)	0.38063 (15)	0.0473 (12)
C101	0.5266 (2)	0.6323 (9)	0.28206 (16)	0.0508 (13)
C93	0.4221 (2)	0.2233 (9)	0.00751 (14)	0.0491 (12)
H93	0.421895	0.385289	0.001226	0.059*
C12	0.5583 (3)	0.4324 (9)	0.83828 (14)	0.0472 (12)
C22	0.5712 (2)	0.2404 (9)	0.80793 (14)	0.0419 (11)
H22	0.592937	0.109674	0.824793	0.050*
C83	0.4237 (2)	0.1737 (9)	0.04854 (16)	0.0497 (13)
H83	0.425760	0.305586	0.066471	0.060*
C73	0.4227 (3)	−0.0583 (10)	0.06989 (16)	0.0529 (13)
C72	0.2721 (3)	0.3127 (9)	0.63801 (15)	0.0489 (13)
C81	0.5725 (3)	0.7792 (9)	0.35621 (16)	0.0535 (14)
H81	0.581250	0.919648	0.371603	0.064*
C103	0.4207 (2)	0.0663 (10)	−0.02977 (16)	0.0514 (13)
C13	0.8778 (3)	0.3719 (10)	0.84062 (15)	0.0491 (12)
C82	0.2875 (3)	0.1317 (9)	0.67172 (15)	0.0556 (14)
H82	0.279576	−0.024454	0.662540	0.067*
C11	0.6810 (2)	0.3539 (10)	0.50468 (15)	0.0481 (12)
C32	0.6115 (2)	0.3138 (9)	0.77553 (15)	0.0498 (13)
H32A	0.589952	0.441971	0.758511	0.060*
H32B	0.650984	0.377609	0.790622	0.060*
C43	0.7849 (3)	0.0456 (13)	0.9188 (2)	0.0697 (18)
H43	0.822027	−0.028181	0.936060	0.084*
C41	0.5778 (3)	0.1467 (13)	0.5543 (2)	0.0720 (18)
H41	0.563871	0.227060	0.527013	0.086*
C23	0.8598 (2)	0.1708 (9)	0.86754 (15)	0.0455 (12)
H23	0.845732	0.035557	0.848866	0.055*
C61	0.5320 (3)	0.2121 (18)	0.5840 (3)	0.118 (3)
H61A	0.544747	0.136243	0.611164	0.176*
H61B	0.490137	0.159832	0.572007	0.176*
H61C	0.531920	0.381835	0.587838	0.176*
C63	0.7483 (4)	−0.1446 (14)	0.8917 (3)	0.115 (3)
H63A	0.713412	−0.072835	0.873179	0.173*
H63B	0.732403	−0.259089	0.909808	0.173*
H63C	0.775639	−0.222773	0.874879	0.173*
C33	0.8072 (2)	0.2367 (10)	0.89182 (15)	0.0484 (12)
H33A	0.821369	0.371009	0.910123	0.058*
H33B	0.771199	0.289945	0.871430	0.058*
C31	0.6429 (2)	0.2349 (11)	0.57165 (16)	0.0565 (14)
H31A	0.656943	0.155701	0.598672	0.068*
H31B	0.640055	0.403795	0.577525	0.068*
C51	0.5771 (4)	−0.1167 (16)	0.5460 (3)	0.126 (3)
H51A	0.596815	−0.198408	0.571273	0.189*
H51B	0.599895	−0.150098	0.523027	0.189*
H51C	0.534065	−0.170063	0.538486	0.189*
C53	0.7449 (3)	0.1578 (18)	0.9483 (2)	0.104 (3)
H53A	0.709838	0.239875	0.931763	0.156*
H53B	0.770065	0.269047	0.966764	0.156*
H53C	0.729231	0.036189	0.965107	0.156*
C62	0.6715 (4)	−0.0570 (14)	0.7684 (3)	0.109 (3)
H62A	0.708479	0.022237	0.783155	0.163*
H62B	0.683827	−0.166297	0.747932	0.163*
H62C	0.651129	−0.142819	0.788511	0.163*
C42	0.6268 (3)	0.1230 (12)	0.74590 (18)	0.0662 (17)
H42	0.587395	0.041567	0.733967	0.079*
C52	0.6544 (4)	0.2321 (18)	0.7097 (2)	0.107 (3)
H52A	0.624722	0.343143	0.694736	0.161*
H52B	0.663204	0.108932	0.690532	0.161*
H52C	0.693037	0.313737	0.720877	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.086 (3)	0.059 (2)	0.0336 (19)	0.001 (2)	−0.0046 (18)	0.0052 (18)
O21	0.067 (2)	0.053 (2)	0.0337 (18)	−0.010 (2)	0.0008 (16)	0.0055 (17)
O31	0.078 (2)	0.062 (2)	0.0326 (19)	−0.003 (2)	−0.0062 (17)	0.0088 (18)
O42	0.078 (2)	0.039 (2)	0.0347 (18)	0.0062 (18)	0.0005 (17)	0.0025 (16)
O61	0.084 (3)	0.043 (2)	0.0356 (19)	0.001 (2)	−0.0068 (18)	−0.0003 (16)
O52	0.103 (3)	0.058 (2)	0.035 (2)	−0.006 (2)	−0.0072 (19)	0.0050 (18)
O22	0.063 (2)	0.065 (2)	0.049 (2)	0.003 (2)	0.0210 (18)	−0.013 (2)
N2	0.056 (2)	0.047 (2)	0.035 (2)	−0.003 (2)	0.0093 (18)	−0.0019 (19)
O12	0.079 (3)	0.077 (3)	0.063 (3)	−0.023 (3)	0.020 (2)	−0.031 (2)
O53	0.082 (3)	0.060 (2)	0.0300 (18)	−0.001 (2)	0.0038 (17)	0.0082 (17)
O33	0.096 (3)	0.057 (2)	0.037 (2)	0.009 (2)	0.0143 (19)	0.0086 (19)
O62	0.088 (3)	0.0397 (19)	0.0321 (18)	0.004 (2)	−0.0026 (18)	−0.0004 (15)
O63	0.137 (4)	0.048 (2)	0.035 (2)	0.009 (3)	0.005 (2)	−0.0025 (18)
N3	0.056 (2)	0.050 (3)	0.034 (2)	0.004 (2)	0.0108 (18)	0.0024 (19)
O13	0.078 (3)	0.079 (3)	0.051 (2)	0.001 (2)	0.003 (2)	0.027 (2)
O32	0.094 (3)	0.054 (2)	0.0357 (19)	0.004 (2)	−0.0069 (18)	−0.0035 (18)
O11	0.088 (3)	0.065 (3)	0.035 (2)	−0.018 (2)	−0.0121 (19)	0.0087 (19)
O41	0.075 (2)	0.0397 (19)	0.044 (2)	−0.0024 (18)	−0.0014 (17)	0.0052 (17)
O23	0.069 (3)	0.072 (3)	0.060 (2)	−0.006 (2)	0.020 (2)	0.017 (2)
O43	0.186 (5)	0.036 (2)	0.043 (2)	0.011 (3)	0.021 (3)	0.0032 (19)
C92	0.092 (4)	0.035 (3)	0.033 (3)	0.003 (3)	0.005 (3)	0.005 (2)
C21	0.053 (3)	0.046 (3)	0.032 (2)	−0.001 (2)	0.004 (2)	0.004 (2)
C102	0.069 (3)	0.045 (3)	0.030 (3)	0.002 (3)	0.004 (2)	0.004 (2)
C91	0.086 (4)	0.035 (3)	0.041 (3)	0.004 (3)	−0.008 (3)	0.004 (2)
N1	0.065 (3)	0.048 (2)	0.0253 (19)	0.006 (2)	0.0012 (18)	0.0041 (18)
C71	0.060 (3)	0.045 (3)	0.034 (3)	−0.001 (3)	0.000 (2)	0.004 (2)
C101	0.064 (3)	0.044 (3)	0.041 (3)	−0.002 (3)	−0.001 (2)	0.006 (2)
C93	0.071 (3)	0.040 (3)	0.036 (3)	0.004 (3)	0.007 (2)	0.002 (2)
C12	0.064 (3)	0.046 (3)	0.032 (2)	−0.003 (3)	0.007 (2)	−0.004 (2)
C22	0.053 (3)	0.041 (3)	0.032 (2)	−0.003 (2)	0.010 (2)	−0.005 (2)
C83	0.069 (3)	0.036 (3)	0.043 (3)	−0.003 (3)	0.006 (2)	−0.002 (2)
C73	0.075 (4)	0.047 (3)	0.036 (3)	0.004 (3)	0.005 (3)	0.001 (2)
C72	0.068 (3)	0.043 (3)	0.035 (3)	0.001 (3)	0.003 (2)	0.001 (2)
C81	0.080 (4)	0.037 (3)	0.039 (3)	0.003 (3)	−0.003 (3)	0.000 (2)
C103	0.064 (3)	0.045 (3)	0.044 (3)	0.002 (3)	0.004 (2)	0.000 (3)
C13	0.065 (3)	0.049 (3)	0.035 (3)	−0.001 (3)	0.013 (2)	0.002 (2)
C82	0.093 (4)	0.035 (3)	0.037 (3)	0.000 (3)	0.006 (3)	0.003 (2)
C11	0.056 (3)	0.057 (3)	0.032 (3)	−0.001 (3)	0.006 (2)	0.002 (2)
C32	0.053 (3)	0.059 (3)	0.041 (3)	−0.003 (3)	0.018 (2)	−0.002 (3)
C43	0.060 (3)	0.082 (5)	0.071 (4)	0.009 (3)	0.021 (3)	0.028 (4)
C41	0.054 (3)	0.088 (5)	0.077 (4)	0.007 (3)	0.017 (3)	0.020 (4)
C23	0.058 (3)	0.041 (3)	0.038 (3)	−0.002 (2)	0.006 (2)	0.000 (2)
C61	0.081 (5)	0.141 (8)	0.144 (8)	0.017 (5)	0.060 (5)	0.033 (7)
C63	0.102 (6)	0.066 (5)	0.190 (10)	−0.029 (5)	0.064 (6)	−0.011 (6)
C33	0.052 (3)	0.054 (3)	0.040 (3)	0.000 (3)	0.011 (2)	0.000 (2)
C31	0.066 (3)	0.064 (4)	0.043 (3)	0.008 (3)	0.019 (3)	0.007 (3)
C51	0.089 (5)	0.090 (7)	0.201 (10)	−0.024 (5)	0.027 (6)	−0.010 (7)
C53	0.095 (5)	0.144 (8)	0.084 (5)	−0.004 (5)	0.049 (4)	0.011 (5)
C62	0.139 (7)	0.066 (5)	0.142 (7)	0.021 (5)	0.085 (6)	0.001 (5)
C42	0.068 (4)	0.077 (5)	0.059 (4)	−0.019 (3)	0.028 (3)	−0.027 (3)
C52	0.123 (6)	0.151 (8)	0.059 (4)	0.008 (6)	0.052 (4)	0.000 (5)

Geometric parameters (Å, º) top

O51—C101	1.229 (6)	C93—C103	1.487 (7)
O21—C11	1.210 (6)	C12—C22	1.516 (7)
O31—C71	1.243 (5)	C22—H22	0.9900
O42—C72	1.287 (6)	C22—C32	1.517 (6)
O61—H61	0.8300	C83—H83	0.9400
O61—C101	1.289 (6)	C83—C73	1.485 (7)
O52—C102	1.237 (5)	C72—C82	1.489 (7)
O22—C12	1.201 (6)	C81—H81	0.9400
N2—H2A	0.9000	C13—C23	1.519 (7)
N2—H2B	0.9000	C82—H82	0.9400
N2—H2C	0.9000	C32—H32A	0.9800
N2—C22	1.496 (6)	C32—H32B	0.9800
O12—H12	0.8300	C32—C42	1.512 (7)
O12—C12	1.313 (6)	C43—H43	0.9900
O53—C103	1.215 (6)	C43—C63	1.524 (10)
O33—C73	1.235 (6)	C43—C33	1.513 (8)
O62—H62	0.8300	C43—C53	1.521 (9)
O62—C102	1.290 (6)	C41—H41	0.9900
O63—H63	0.8300	C41—C61	1.528 (9)
O63—C103	1.286 (6)	C41—C31	1.511 (8)
N3—H3A	0.9000	C41—C51	1.516 (11)
N3—H3B	0.9000	C23—H23	0.9900
N3—H3C	0.9000	C23—C33	1.523 (7)
N3—C23	1.499 (6)	C61—H61A	0.9700
O13—H13	0.8300	C61—H61B	0.9700
O13—C13	1.326 (6)	C61—H61C	0.9700
O32—C72	1.244 (6)	C63—H63A	0.9700
O11—H11	0.8300	C63—H63B	0.9700
O11—C11	1.318 (6)	C63—H63C	0.9700
O41—C71	1.283 (6)	C33—H33A	0.9800
O23—C13	1.197 (6)	C33—H33B	0.9800
O43—C73	1.279 (7)	C31—H31A	0.9800
C92—H92	0.9400	C31—H31B	0.9800
C92—C102	1.479 (7)	C51—H51A	0.9700
C92—C82	1.325 (7)	C51—H51B	0.9700
C21—H21	0.9900	C51—H51C	0.9700
C21—N1	1.491 (6)	C53—H53A	0.9700
C21—C11	1.519 (7)	C53—H53B	0.9700
C21—C31	1.515 (7)	C53—H53C	0.9700
C91—H91	0.9400	C62—H62A	0.9700
C91—C101	1.494 (7)	C62—H62B	0.9700
C91—C81	1.325 (7)	C62—H62C	0.9700
N1—H1A	0.9000	C62—C42	1.507 (10)
N1—H1B	0.9000	C42—H42	0.9900
N1—H1C	0.9000	C42—C52	1.519 (9)
C71—C81	1.484 (7)	C52—H52A	0.9700
C93—H93	0.9400	C52—H52B	0.9700
C93—C83	1.341 (6)	C52—H52C	0.9700

C101—O61—H61	109.5	O11—C11—C21	112.1 (5)
H2A—N2—H2B	109.5	C22—C32—H32A	108.2
H2A—N2—H2C	109.5	C22—C32—H32B	108.2
H2B—N2—H2C	109.5	H32A—C32—H32B	107.4
C22—N2—H2A	109.5	C42—C32—C22	116.3 (5)
C22—N2—H2B	109.5	C42—C32—H32A	108.2
C22—N2—H2C	109.5	C42—C32—H32B	108.2
C12—O12—H12	109.5	C63—C43—H43	108.6
C102—O62—H62	109.5	C33—C43—H43	108.6
C103—O63—H63	109.5	C33—C43—C63	111.4 (6)
H3A—N3—H3B	109.5	C33—C43—C53	108.8 (6)
H3A—N3—H3C	109.5	C53—C43—H43	108.6
H3B—N3—H3C	109.5	C53—C43—C63	110.8 (6)
C23—N3—H3A	109.5	C61—C41—H41	107.8
C23—N3—H3B	109.5	C31—C41—H41	107.8
C23—N3—H3C	109.5	C31—C41—C61	110.4 (6)
C13—O13—H13	109.5	C31—C41—C51	111.9 (6)
C11—O11—H11	109.5	C51—C41—H41	107.8
C102—C92—H92	114.8	C51—C41—C61	111.0 (7)
C82—C92—H92	114.8	N3—C23—C13	106.7 (4)
C82—C92—C102	130.3 (5)	N3—C23—H23	108.6
N1—C21—H21	109.9	N3—C23—C33	111.4 (4)
N1—C21—C11	106.2 (4)	C13—C23—H23	108.6
N1—C21—C31	108.9 (4)	C13—C23—C33	112.8 (4)
C11—C21—H21	109.9	C33—C23—H23	108.6
C31—C21—H21	109.9	C41—C61—H61A	109.5
C31—C21—C11	111.9 (4)	C41—C61—H61B	109.5
O52—C102—O62	120.6 (5)	C41—C61—H61C	109.5
O52—C102—C92	118.3 (5)	H61A—C61—H61B	109.5
O62—C102—C92	121.2 (4)	H61A—C61—H61C	109.5
C101—C91—H91	114.6	H61B—C61—H61C	109.5
C81—C91—H91	114.6	C43—C63—H63A	109.5
C81—C91—C101	130.8 (5)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—C23	116.7 (5)
H1B—N1—H1C	109.5	C43—C33—H33A	108.1
O31—C71—O41	122.5 (5)	C43—C33—H33B	108.1
O31—C71—C81	116.5 (5)	C23—C33—H33A	108.1
O41—C71—C81	121.0 (4)	C23—C33—H33B	108.1
O51—C101—O61	121.2 (5)	H33A—C33—H33B	107.3
O51—C101—C91	118.9 (5)	C21—C31—H31A	108.1
O61—C101—C91	119.9 (4)	C21—C31—H31B	108.1
C83—C93—H93	114.4	C41—C31—C21	116.7 (5)
C83—C93—C103	131.1 (5)	C41—C31—H31A	108.1
C103—C93—H93	114.4	C41—C31—H31B	108.1
O22—C12—O12	124.6 (5)	H31A—C31—H31B	107.3
O22—C12—C22	122.3 (5)	C41—C51—H51A	109.5
O12—C12—C22	113.0 (4)	C41—C51—H51B	109.5
N2—C22—C12	105.3 (4)	C41—C51—H51C	109.5
N2—C22—H22	107.9	H51A—C51—H51B	109.5
N2—C22—C32	112.4 (4)	H51A—C51—H51C	109.5
C12—C22—H22	107.9	H51B—C51—H51C	109.5
C12—C22—C32	115.4 (4)	C43—C53—H53A	109.5
C32—C22—H22	107.9	C43—C53—H53B	109.5
C93—C83—H83	115.2	C43—C53—H53C	109.5
C93—C83—C73	129.7 (5)	H53A—C53—H53B	109.5
C73—C83—H83	115.2	H53A—C53—H53C	109.5
O33—C73—O43	121.4 (5)	H53B—C53—H53C	109.5
O33—C73—C83	118.0 (5)	H62A—C62—H62B	109.5
O43—C73—C83	120.5 (4)	H62A—C62—H62C	109.5
O42—C72—C82	119.9 (4)	H62B—C62—H62C	109.5
O32—C72—O42	122.0 (5)	C42—C62—H62A	109.5
O32—C72—C82	118.1 (5)	C42—C62—H62B	109.5
C91—C81—C71	130.3 (5)	C42—C62—H62C	109.5
C91—C81—H81	114.8	C32—C42—H42	108.3
C71—C81—H81	114.8	C32—C42—C52	110.0 (6)
O53—C103—O63	121.3 (5)	C62—C42—C32	111.9 (5)
O53—C103—C93	119.6 (5)	C62—C42—H42	108.3
O63—C103—C93	119.1 (5)	C62—C42—C52	109.9 (6)
O13—C13—C23	111.2 (5)	C52—C42—H42	108.3
O23—C13—O13	125.3 (5)	C42—C52—H52A	109.5
O23—C13—C23	123.6 (5)	C42—C52—H52B	109.5
C92—C82—C72	131.2 (5)	C42—C52—H52C	109.5
C92—C82—H82	114.4	H52A—C52—H52B	109.5
C72—C82—H82	114.4	H52A—C52—H52C	109.5
O21—C11—O11	125.1 (5)	H52B—C52—H52C	109.5
O21—C11—C21	122.7 (4)

O31—C71—C81—C91	179.7 (6)	C93—C83—C73—O43	11.8 (9)
O42—C72—C82—C92	−3.0 (10)	C12—C22—C32—C42	178.0 (5)
O22—C12—C22—N2	17.2 (6)	C22—C32—C42—C62	−70.0 (7)
O22—C12—C22—C32	141.7 (5)	C22—C32—C42—C52	167.5 (5)
N2—C22—C32—C42	−61.4 (6)	C83—C93—C103—O53	174.6 (6)
O12—C12—C22—N2	−165.5 (4)	C83—C93—C103—O63	−5.5 (9)
O12—C12—C22—C32	−41.0 (6)	C81—C91—C101—O51	179.4 (6)
N3—C23—C33—C43	−61.4 (6)	C81—C91—C101—O61	0.2 (10)
O13—C13—C23—N3	−173.7 (4)	C103—C93—C83—C73	−2.0 (10)
O13—C13—C23—C33	−51.0 (6)	C13—C23—C33—C43	178.6 (5)
O32—C72—C82—C92	176.5 (6)	C82—C92—C102—O52	−178.5 (6)
O41—C71—C81—C91	0.7 (10)	C82—C92—C102—O62	2.1 (10)
O23—C13—C23—N3	5.7 (7)	C11—C21—C31—C41	68.5 (6)
O23—C13—C23—C33	128.4 (6)	C61—C41—C31—C21	−175.3 (6)
C102—C92—C82—C72	−1.7 (12)	C63—C43—C33—C23	−71.3 (6)
N1—C21—C11—O21	−26.4 (7)	C31—C21—C11—O21	92.3 (6)
N1—C21—C11—O11	155.7 (4)	C31—C21—C11—O11	−85.5 (6)
N1—C21—C31—C41	−174.5 (5)	C51—C41—C31—C21	60.4 (8)
C101—C91—C81—C71	−0.3 (12)	C53—C43—C33—C23	166.3 (5)
C93—C83—C73—O33	−168.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.83	1.59	2.424 (5)	179
N2—H2A···O61ⁱ	0.90	2.05	2.906 (5)	160
N2—H2B···O23ⁱⁱ	0.90	2.04	2.863 (5)	151
N2—H2C···O51ⁱⁱⁱ	0.90	1.90	2.780 (6)	164
O12—H12···O33^iv	0.83	1.80	2.596 (6)	160
O62—H62···O42	0.83	1.61	2.439 (4)	174
O63—H63···O43	0.83	1.60	2.421 (5)	172
N3—H3A···O22^v	0.90	1.93	2.780 (5)	158
N3—H3B···O53^vi	0.90	1.94	2.834 (6)	171
N3—H3C···O63^vii	0.90	2.02	2.867 (5)	155
O13—H13···O52^viii	0.83	1.79	2.599 (6)	163
O11—H11···O31	0.83	1.77	2.599 (5)	172
N1—H1A···O21^ix	0.90	2.15	2.890 (5)	138
N1—H1A···O31^ix	0.90	2.42	3.005 (5)	123
N1—H1B···O42^v	0.90	1.97	2.867 (5)	177
N1—H1C···O32^viii	0.90	1.99	2.863 (6)	165

L-Leucinium hydrogen maleate (l_leu_mal_275) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.266 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.6777 (9) Å	Cell parameters from 4195 reflections
b = 5.66500 (18) Å	θ = 1.9–29.0°
c = 32.0878 (8) Å	µ = 0.11 mm⁻¹
β = 99.115 (3)°	T = 275 K
V = 3890.8 (2) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7709 independent reflections
Radiation source: fine-focus sealed X-ray tube	4553 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.674, T_max = 1.000	k = −7→6
23127 measured reflections	l = −40→40

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.054P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
7709 reflections	Δρ_max = 0.17 e Å⁻³
475 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint

Special details top

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

	x	y	z	U_iso*/U_eq
O51	0.50432 (18)	0.7056 (7)	0.24746 (10)	0.0672 (10)
O21	0.70372 (15)	0.5471 (6)	0.50326 (9)	0.0548 (9)
O31	0.61441 (16)	0.5865 (7)	0.41839 (10)	0.0650 (10)
O42	0.27775 (16)	0.5312 (6)	0.64746 (9)	0.0542 (9)
O61	0.53426 (18)	0.4119 (6)	0.29048 (10)	0.0616 (10)
H61	0.548519	0.393466	0.315502	0.092*
O52	0.35118 (19)	0.3364 (7)	0.77547 (11)	0.0740 (11)
O22	0.50746 (16)	0.4548 (7)	0.84933 (10)	0.0622 (9)
N2	0.50688 (17)	0.1547 (7)	0.78760 (11)	0.0493 (10)
H2A	0.489936	0.258401	0.768288	0.059*
H2B	0.482468	0.139070	0.807273	0.059*
H2C	0.510713	0.015690	0.775338	0.059*
O12	0.60649 (17)	0.5624 (8)	0.85114 (12)	0.0773 (12)
H12	0.598292	0.655770	0.869009	0.116*
O53	0.41501 (17)	0.1528 (7)	−0.06458 (10)	0.0635 (10)
O33	0.41549 (18)	−0.0608 (7)	0.10738 (10)	0.0681 (10)
O62	0.32375 (19)	0.5700 (6)	0.72140 (10)	0.0614 (10)
H62	0.307685	0.560354	0.696544	0.092*
O63	0.4259 (2)	−0.1571 (7)	−0.02387 (11)	0.0825 (13)
H63	0.426859	−0.188198	0.001181	0.124*
N3	0.91794 (16)	0.1025 (7)	0.89674 (11)	0.0493 (10)
H3A	0.950028	0.098423	0.882553	0.059*
H3B	0.912793	−0.039450	0.907587	0.059*
H3C	0.925518	0.207866	0.917491	0.059*
O13	0.82774 (18)	0.4602 (8)	0.81649 (12)	0.0783 (12)
H13	0.838628	0.562106	0.801022	0.118*
O32	0.25307 (18)	0.2417 (7)	0.60168 (10)	0.0677 (10)
O11	0.64254 (19)	0.2529 (7)	0.47374 (10)	0.0698 (11)
H11	0.631937	0.349678	0.454965	0.105*
O41	0.58154 (17)	0.3582 (6)	0.36347 (10)	0.0580 (9)
O23	0.92987 (18)	0.4424 (8)	0.84196 (11)	0.0716 (11)
O43	0.4307 (3)	−0.2482 (7)	0.05032 (12)	0.0983 (16)
C92	0.3099 (3)	0.1515 (9)	0.71227 (15)	0.0596 (14)
H92	0.315099	0.009787	0.727038	0.071*
C21	0.6925 (2)	0.2001 (9)	0.54391 (13)	0.0468 (11)
H21	0.694248	0.033865	0.535736	0.056*
C102	0.3289 (2)	0.3632 (9)	0.73776 (14)	0.0539 (13)
C91	0.5483 (3)	0.8096 (9)	0.31653 (15)	0.0613 (14)
H91	0.542341	0.966202	0.308173	0.074*
N1	0.75377 (17)	0.2736 (7)	0.56780 (11)	0.0497 (10)
H1A	0.783624	0.246527	0.552285	0.060*
H1B	0.761702	0.191409	0.591688	0.060*
H1C	0.752729	0.426825	0.573749	0.060*
C71	0.5905 (2)	0.5614 (10)	0.38096 (14)	0.0521 (12)
C101	0.5279 (2)	0.6329 (9)	0.28245 (15)	0.0527 (12)
C93	0.4221 (2)	0.2231 (9)	0.00787 (14)	0.0538 (12)
H93	0.422072	0.383398	0.001608	0.065*
C12	0.5576 (2)	0.4333 (9)	0.83798 (13)	0.0478 (11)
C22	0.5699 (2)	0.2401 (9)	0.80759 (13)	0.0443 (10)
H22	0.591187	0.110108	0.824153	0.053*
C83	0.4237 (2)	0.1736 (9)	0.04892 (14)	0.0519 (12)
H83	0.425629	0.304138	0.066647	0.062*
C73	0.4228 (2)	−0.0578 (10)	0.07018 (15)	0.0572 (13)
C72	0.2716 (2)	0.3120 (9)	0.63802 (14)	0.0520 (13)
C81	0.5733 (2)	0.7801 (9)	0.35662 (15)	0.0563 (13)
H81	0.581330	0.919197	0.371923	0.068*
C103	0.4204 (2)	0.0652 (10)	−0.02928 (15)	0.0538 (12)
C13	0.8778 (3)	0.3721 (9)	0.84083 (14)	0.0540 (13)
C82	0.2867 (3)	0.1305 (9)	0.67168 (15)	0.0631 (15)
H82	0.278489	−0.024014	0.662662	0.076*
C11	0.6808 (2)	0.3539 (10)	0.50473 (14)	0.0511 (12)
C32	0.6099 (2)	0.3144 (9)	0.77505 (15)	0.0534 (13)
H32A	0.588481	0.440493	0.758128	0.064*
H32B	0.648761	0.378708	0.789844	0.064*
C43	0.7846 (3)	0.0451 (13)	0.9184 (2)	0.0792 (19)
H43	0.821092	−0.029084	0.935364	0.095*
C41	0.5781 (3)	0.1444 (13)	0.5540 (2)	0.0782 (18)
H41	0.564650	0.223347	0.526939	0.094*
C23	0.8600 (2)	0.1705 (9)	0.86753 (13)	0.0478 (11)
H23	0.846477	0.036402	0.849032	0.057*
C61	0.5317 (3)	0.2132 (19)	0.5840 (3)	0.131 (3)
H61A	0.544253	0.140095	0.610970	0.196*
H61B	0.490531	0.160552	0.572210	0.196*
H61C	0.531592	0.381561	0.587294	0.196*
C63	0.7483 (4)	−0.1438 (13)	0.8914 (3)	0.128 (3)
H63A	0.713443	−0.072858	0.873571	0.193*
H63B	0.733362	−0.259529	0.909232	0.193*
H63C	0.775060	−0.218575	0.874186	0.193*
C33	0.8072 (2)	0.2356 (10)	0.89187 (14)	0.0523 (12)
H33A	0.821121	0.367971	0.910143	0.063*
H33B	0.771931	0.289372	0.871695	0.063*
C31	0.6421 (2)	0.2341 (11)	0.57160 (15)	0.0602 (14)
H31A	0.655762	0.156129	0.598390	0.072*
H31B	0.638927	0.401443	0.577324	0.072*
C51	0.5771 (4)	−0.1170 (15)	0.5461 (3)	0.141 (4)
H51A	0.597436	−0.197116	0.570865	0.212*
H51B	0.598521	−0.150900	0.522816	0.212*
H51C	0.534563	−0.170009	0.539538	0.212*
C53	0.7449 (3)	0.1557 (18)	0.9483 (2)	0.117 (3)
H53A	0.710887	0.241126	0.932248	0.176*
H53B	0.770037	0.261912	0.967155	0.176*
H53C	0.728606	0.033885	0.964286	0.176*
C62	0.6698 (4)	−0.0568 (14)	0.7679 (3)	0.124 (3)
H62A	0.707305	0.020472	0.781096	0.186*
H62B	0.680013	−0.169825	0.747733	0.186*
H62C	0.650634	−0.136120	0.788944	0.186*
C42	0.6254 (3)	0.1235 (12)	0.74574 (18)	0.0728 (17)
H42	0.586515	0.042853	0.733932	0.087*
C52	0.6530 (4)	0.2339 (19)	0.7094 (2)	0.120 (3)
H52A	0.623768	0.344251	0.694702	0.180*
H52B	0.661690	0.112373	0.690325	0.180*
H52C	0.691090	0.314678	0.720428	0.180*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.095 (3)	0.062 (2)	0.0391 (19)	0.003 (2)	−0.0071 (17)	0.0073 (18)
O21	0.069 (2)	0.057 (2)	0.0362 (17)	−0.0121 (19)	0.0007 (15)	0.0056 (16)
O31	0.086 (2)	0.068 (2)	0.0354 (18)	−0.004 (2)	−0.0077 (17)	0.0080 (17)
O42	0.082 (2)	0.0418 (19)	0.0356 (17)	0.0051 (18)	0.0014 (16)	0.0028 (15)
O61	0.093 (3)	0.045 (2)	0.0397 (18)	0.003 (2)	−0.0090 (18)	0.0002 (16)
O52	0.114 (3)	0.061 (2)	0.040 (2)	−0.010 (2)	−0.0082 (19)	0.0068 (18)
O22	0.069 (2)	0.068 (2)	0.054 (2)	0.001 (2)	0.0226 (18)	−0.0127 (19)
N2	0.060 (2)	0.051 (2)	0.036 (2)	−0.001 (2)	0.0073 (17)	−0.0008 (19)
O12	0.085 (3)	0.085 (3)	0.065 (3)	−0.025 (2)	0.021 (2)	−0.037 (2)
O53	0.088 (2)	0.068 (2)	0.0330 (18)	0.000 (2)	0.0048 (16)	0.0083 (17)
O33	0.108 (3)	0.059 (2)	0.0383 (19)	0.010 (2)	0.0144 (18)	0.0111 (18)
O62	0.102 (3)	0.043 (2)	0.0352 (18)	0.002 (2)	−0.0018 (18)	0.0014 (15)
O63	0.156 (4)	0.051 (2)	0.039 (2)	0.009 (3)	0.008 (2)	−0.0013 (17)
N3	0.059 (2)	0.055 (3)	0.035 (2)	0.002 (2)	0.0115 (17)	0.0006 (18)
O13	0.091 (3)	0.085 (3)	0.056 (2)	0.001 (2)	0.003 (2)	0.030 (2)
O32	0.101 (3)	0.057 (2)	0.0388 (19)	0.003 (2)	−0.0091 (18)	−0.0025 (17)
O11	0.090 (3)	0.070 (2)	0.041 (2)	−0.021 (2)	−0.0141 (18)	0.0106 (18)
O41	0.081 (2)	0.0420 (18)	0.0463 (19)	−0.0006 (18)	−0.0051 (17)	0.0076 (16)
O23	0.076 (3)	0.081 (3)	0.061 (2)	−0.009 (2)	0.020 (2)	0.019 (2)
O43	0.210 (5)	0.041 (2)	0.045 (2)	0.013 (3)	0.023 (3)	0.0020 (19)
C92	0.097 (4)	0.041 (3)	0.039 (3)	0.002 (3)	0.005 (3)	0.003 (2)
C21	0.055 (3)	0.052 (3)	0.033 (2)	0.001 (2)	0.004 (2)	0.003 (2)
C102	0.078 (3)	0.050 (3)	0.032 (2)	0.005 (3)	0.002 (2)	0.007 (2)
C91	0.096 (4)	0.037 (3)	0.045 (3)	0.001 (3)	−0.007 (3)	0.001 (2)
N1	0.066 (2)	0.053 (2)	0.0295 (19)	0.006 (2)	0.0026 (17)	0.0053 (18)
C71	0.065 (3)	0.052 (3)	0.036 (3)	0.000 (3)	−0.001 (2)	0.004 (2)
C101	0.068 (3)	0.046 (3)	0.041 (3)	0.000 (3)	0.001 (2)	0.004 (2)
C93	0.078 (3)	0.041 (3)	0.041 (3)	0.003 (3)	0.007 (2)	0.001 (2)
C12	0.067 (3)	0.045 (3)	0.031 (2)	−0.001 (3)	0.005 (2)	0.000 (2)
C22	0.056 (3)	0.046 (3)	0.033 (2)	−0.002 (2)	0.0111 (19)	−0.002 (2)
C83	0.077 (3)	0.038 (3)	0.040 (3)	0.002 (2)	0.006 (2)	−0.003 (2)
C73	0.086 (4)	0.049 (3)	0.035 (3)	0.003 (3)	0.005 (2)	0.004 (2)
C72	0.070 (3)	0.051 (3)	0.033 (3)	0.000 (3)	0.003 (2)	0.001 (2)
C81	0.085 (4)	0.036 (3)	0.043 (3)	0.002 (3)	−0.006 (3)	−0.005 (2)
C103	0.069 (3)	0.048 (3)	0.042 (3)	0.001 (3)	0.002 (2)	0.000 (2)
C13	0.074 (4)	0.054 (3)	0.035 (3)	0.000 (3)	0.012 (2)	0.004 (2)
C82	0.105 (4)	0.037 (3)	0.044 (3)	−0.003 (3)	0.003 (3)	0.000 (2)
C11	0.061 (3)	0.059 (3)	0.033 (2)	−0.001 (3)	0.007 (2)	0.004 (2)
C32	0.055 (3)	0.059 (3)	0.048 (3)	−0.003 (3)	0.013 (2)	−0.003 (2)
C43	0.067 (4)	0.092 (5)	0.084 (4)	0.010 (4)	0.027 (3)	0.035 (4)
C41	0.059 (3)	0.092 (5)	0.085 (4)	0.007 (3)	0.018 (3)	0.021 (4)
C23	0.063 (3)	0.048 (3)	0.033 (2)	−0.001 (2)	0.008 (2)	0.001 (2)
C61	0.094 (5)	0.164 (9)	0.150 (8)	0.015 (6)	0.068 (5)	0.027 (7)
C63	0.109 (6)	0.070 (5)	0.224 (10)	−0.025 (5)	0.078 (6)	−0.009 (6)
C33	0.057 (3)	0.060 (3)	0.041 (3)	−0.002 (3)	0.008 (2)	0.001 (2)
C31	0.074 (3)	0.065 (3)	0.046 (3)	0.010 (3)	0.021 (2)	0.010 (3)
C51	0.103 (6)	0.091 (6)	0.231 (11)	−0.025 (5)	0.026 (6)	−0.010 (7)
C53	0.103 (5)	0.168 (9)	0.095 (5)	−0.002 (6)	0.057 (4)	0.017 (6)
C62	0.150 (7)	0.073 (5)	0.173 (8)	0.019 (5)	0.098 (6)	−0.006 (6)
C42	0.076 (4)	0.083 (5)	0.066 (4)	−0.021 (3)	0.033 (3)	−0.030 (3)
C52	0.132 (6)	0.175 (9)	0.066 (4)	0.008 (6)	0.060 (4)	0.004 (5)

Geometric parameters (Å, º) top

O51—C101	1.229 (5)	C93—C103	1.486 (7)
O21—C11	1.206 (6)	C12—C22	1.517 (6)
O31—C71	1.238 (5)	C22—H22	0.9800
O42—C72	1.280 (6)	C22—C32	1.519 (6)
O61—H61	0.8200	C83—H83	0.9300
O61—C101	1.281 (6)	C83—C73	1.479 (7)
O52—C102	1.239 (5)	C72—C82	1.490 (7)
O22—C12	1.205 (5)	C81—H81	0.9300
N2—H2A	0.8900	C13—C23	1.514 (7)
N2—H2B	0.8900	C82—H82	0.9300
N2—H2C	0.8900	C32—H32A	0.9700
N2—C22	1.495 (5)	C32—H32B	0.9700
O12—H12	0.8200	C32—C42	1.505 (7)
O12—C12	1.303 (6)	C43—H43	0.9800
O53—C103	1.225 (6)	C43—C63	1.518 (10)
O33—C73	1.229 (5)	C43—C33	1.505 (8)
O62—H62	0.8200	C43—C53	1.521 (9)
O62—C102	1.282 (6)	C41—H41	0.9800
O63—H63	0.8200	C41—C61	1.546 (9)
O63—C103	1.274 (6)	C41—C31	1.502 (8)
N3—H3A	0.8900	C41—C51	1.502 (11)
N3—H3B	0.8900	C23—H23	0.9800
N3—H3C	0.8900	C23—C33	1.528 (6)
N3—C23	1.494 (5)	C61—H61A	0.9600
O13—H13	0.8200	C61—H61B	0.9600
O13—C13	1.330 (6)	C61—H61C	0.9600
O32—C72	1.237 (5)	C63—H63A	0.9600
O11—H11	0.8200	C63—H63B	0.9600
O11—C11	1.320 (6)	C63—H63C	0.9600
O41—C71	1.282 (6)	C33—H33A	0.9700
O23—C13	1.192 (6)	C33—H33B	0.9700
O43—C73	1.278 (6)	C31—H31A	0.9700
C92—H92	0.9300	C31—H31B	0.9700
C92—C102	1.473 (7)	C51—H51A	0.9600
C92—C82	1.325 (7)	C51—H51B	0.9600
C21—H21	0.9800	C51—H51C	0.9600
C21—N1	1.484 (5)	C53—H53A	0.9600
C21—C11	1.517 (6)	C53—H53B	0.9600
C21—C31	1.526 (6)	C53—H53C	0.9600
C91—H91	0.9300	C62—H62A	0.9600
C91—C101	1.496 (7)	C62—H62B	0.9600
C91—C81	1.325 (6)	C62—H62C	0.9600
N1—H1A	0.8900	C62—C42	1.504 (10)
N1—H1B	0.8900	C42—H42	0.9800
N1—H1C	0.8900	C42—C52	1.527 (9)
C71—C81	1.481 (7)	C52—H52A	0.9600
C93—H93	0.9300	C52—H52B	0.9600
C93—C83	1.342 (6)	C52—H52C	0.9600

C101—O61—H61	109.5	O11—C11—C21	112.2 (4)
H2A—N2—H2B	109.5	C22—C32—H32A	108.3
H2A—N2—H2C	109.5	C22—C32—H32B	108.3
H2B—N2—H2C	109.5	H32A—C32—H32B	107.4
C22—N2—H2A	109.5	C42—C32—C22	116.0 (4)
C22—N2—H2B	109.5	C42—C32—H32A	108.3
C22—N2—H2C	109.5	C42—C32—H32B	108.3
C12—O12—H12	109.5	C63—C43—H43	108.4
C102—O62—H62	109.5	C63—C43—C53	110.9 (6)
C103—O63—H63	109.5	C33—C43—H43	108.4
H3A—N3—H3B	109.5	C33—C43—C63	111.6 (6)
H3A—N3—H3C	109.5	C33—C43—C53	109.2 (6)
H3B—N3—H3C	109.5	C53—C43—H43	108.4
C23—N3—H3A	109.5	C61—C41—H41	107.8
C23—N3—H3B	109.5	C31—C41—H41	107.8
C23—N3—H3C	109.5	C31—C41—C61	109.5 (6)
C13—O13—H13	109.5	C31—C41—C51	112.7 (6)
C11—O11—H11	109.5	C51—C41—H41	107.8
C102—C92—H92	114.8	C51—C41—C61	111.1 (7)
C82—C92—H92	114.8	N3—C23—C13	106.6 (4)
C82—C92—C102	130.4 (5)	N3—C23—H23	108.7
N1—C21—H21	109.8	N3—C23—C33	111.4 (3)
N1—C21—C11	106.6 (4)	C13—C23—H23	108.7
N1—C21—C31	109.2 (4)	C13—C23—C33	112.7 (4)
C11—C21—H21	109.8	C33—C23—H23	108.7
C11—C21—C31	111.7 (4)	C41—C61—H61A	109.5
C31—C21—H21	109.8	C41—C61—H61B	109.5
O52—C102—O62	120.5 (5)	C41—C61—H61C	109.5
O52—C102—C92	118.3 (5)	H61A—C61—H61B	109.5
O62—C102—C92	121.2 (4)	H61A—C61—H61C	109.5
C101—C91—H91	114.6	H61B—C61—H61C	109.5
C81—C91—H91	114.6	C43—C63—H63A	109.5
C81—C91—C101	130.8 (5)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—C23	117.0 (5)
H1B—N1—H1C	109.5	C43—C33—H33A	108.1
O31—C71—O41	122.6 (5)	C43—C33—H33B	108.1
O31—C71—C81	116.6 (5)	C23—C33—H33A	108.1
O41—C71—C81	120.8 (4)	C23—C33—H33B	108.1
O51—C101—O61	121.8 (5)	H33A—C33—H33B	107.3
O51—C101—C91	118.4 (4)	C21—C31—H31A	108.2
O61—C101—C91	119.8 (4)	C21—C31—H31B	108.2
C83—C93—H93	114.5	C41—C31—C21	116.3 (5)
C83—C93—C103	130.9 (5)	C41—C31—H31A	108.2
C103—C93—H93	114.5	C41—C31—H31B	108.2
O22—C12—O12	124.9 (5)	H31A—C31—H31B	107.4
O22—C12—C22	121.8 (4)	C41—C51—H51A	109.5
O12—C12—C22	113.3 (4)	C41—C51—H51B	109.5
N2—C22—C12	105.5 (4)	C41—C51—H51C	109.5
N2—C22—H22	108.0	H51A—C51—H51B	109.5
N2—C22—C32	112.2 (4)	H51A—C51—H51C	109.5
C12—C22—H22	108.0	H51B—C51—H51C	109.5
C12—C22—C32	114.8 (4)	C43—C53—H53A	109.5
C32—C22—H22	108.0	C43—C53—H53B	109.5
C93—C83—H83	115.2	C43—C53—H53C	109.5
C93—C83—C73	129.6 (5)	H53A—C53—H53B	109.5
C73—C83—H83	115.2	H53A—C53—H53C	109.5
O33—C73—O43	121.4 (5)	H53B—C53—H53C	109.5
O33—C73—C83	118.2 (5)	H62A—C62—H62B	109.5
O43—C73—C83	120.4 (4)	H62A—C62—H62C	109.5
O42—C72—C82	119.7 (4)	H62B—C62—H62C	109.5
O32—C72—O42	122.8 (5)	C42—C62—H62A	109.5
O32—C72—C82	117.5 (5)	C42—C62—H62B	109.5
C91—C81—C71	130.4 (5)	C42—C62—H62C	109.5
C91—C81—H81	114.8	C32—C42—H42	108.3
C71—C81—H81	114.8	C32—C42—C52	109.6 (6)
O53—C103—O63	121.3 (5)	C62—C42—C32	112.5 (5)
O53—C103—C93	118.9 (5)	C62—C42—H42	108.3
O63—C103—C93	119.7 (4)	C62—C42—C52	109.8 (6)
O13—C13—C23	111.0 (5)	C52—C42—H42	108.3
O23—C13—O13	125.0 (5)	C42—C52—H52A	109.5
O23—C13—C23	124.1 (5)	C42—C52—H52B	109.5
C92—C82—C72	131.0 (5)	C42—C52—H52C	109.5
C92—C82—H82	114.5	H52A—C52—H52B	109.5
C72—C82—H82	114.5	H52A—C52—H52C	109.5
O21—C11—O11	125.3 (4)	H52B—C52—H52C	109.5
O21—C11—C21	122.5 (4)

O31—C71—C81—C91	178.9 (6)	C93—C83—C73—O43	11.6 (9)
O42—C72—C82—C92	−3.9 (10)	C12—C22—C32—C42	177.3 (5)
O22—C12—C22—N2	16.9 (6)	C22—C32—C42—C62	−69.8 (6)
O22—C12—C22—C32	140.9 (5)	C22—C32—C42—C52	167.8 (5)
N2—C22—C32—C42	−62.3 (6)	C83—C93—C103—O53	175.3 (5)
O12—C12—C22—N2	−165.6 (4)	C83—C93—C103—O63	−6.1 (9)
O12—C12—C22—C32	−41.6 (6)	C81—C91—C101—O51	178.3 (6)
N3—C23—C33—C43	−62.1 (6)	C81—C91—C101—O61	−0.3 (10)
O13—C13—C23—N3	−174.0 (4)	C103—C93—C83—C73	−1.5 (9)
O13—C13—C23—C33	−51.6 (6)	C13—C23—C33—C43	178.2 (5)
O32—C72—C82—C92	176.3 (6)	C82—C92—C102—O52	−178.0 (6)
O41—C71—C81—C91	−0.3 (10)	C82—C92—C102—O62	0.5 (10)
O23—C13—C23—N3	5.4 (7)	C11—C21—C31—C41	68.6 (6)
O23—C13—C23—C33	127.9 (5)	C61—C41—C31—C21	−174.8 (6)
C102—C92—C82—C72	−0.3 (11)	C63—C43—C33—C23	−71.2 (6)
N1—C21—C11—O21	−25.7 (6)	C31—C21—C11—O21	93.5 (6)
N1—C21—C11—O11	155.4 (4)	C31—C21—C11—O11	−85.4 (5)
N1—C21—C31—C41	−173.8 (5)	C51—C41—C31—C21	61.0 (8)
C101—C91—C81—C71	1.2 (11)	C53—C43—C33—C23	165.9 (5)
C93—C83—C73—O33	−169.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.82	1.60	2.422 (4)	176
N2—H2A···O61ⁱ	0.89	2.07	2.914 (5)	158
N2—H2B···O23ⁱⁱ	0.89	2.05	2.863 (5)	152
N2—H2C···O51ⁱⁱⁱ	0.89	1.91	2.777 (5)	164
O12—H12···O33^iv	0.82	1.82	2.599 (5)	158
O62—H62···O42	0.82	1.61	2.434 (4)	178
O63—H63···O43	0.82	1.60	2.422 (5)	179
N3—H3A···O22^v	0.89	1.94	2.778 (5)	156
N3—H3B···O53^vi	0.89	1.96	2.838 (5)	171
N3—H3C···O63^vii	0.89	2.03	2.870 (5)	157
O13—H13···O52^viii	0.82	1.80	2.597 (5)	165
O11—H11···O31	0.82	1.78	2.599 (5)	173
N1—H1A···O21^ix	0.89	2.16	2.891 (5)	139
N1—H1A···O31^ix	0.89	2.44	3.014 (5)	123
N1—H1B···O42^v	0.89	1.99	2.875 (5)	175
N1—H1C···O32^viii	0.89	2.00	2.867 (5)	166

L-Leucinium hydrogen maleate (l_leu_mal_293) top

Crystal data top

C₆H₁₄NO₂⁺·C₄H₃O₄⁻	F(000) = 1584
M_r = 247.24	D_x = 1.261 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.7528 (11) Å	Cell parameters from 4089 reflections
b = 5.6663 (2) Å	θ = 1.9–29.2°
c = 32.0956 (10) Å	µ = 0.10 mm⁻¹
β = 98.955 (4)°	T = 293 K
V = 3907.8 (3) Å³	Needle
Z = 12	4 × 0.12 × 0.06 mm

Data collection top

STOE IPDS 2 diffractometer	7754 independent reflections
Radiation source: fine-focus sealed X-ray tube	4814 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −26→26
T_min = 0.553, T_max = 1.000	k = −7→6
23451 measured reflections	l = −40→40

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0557P)² + 0.5661P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
7754 reflections	Δρ_max = 0.14 e Å⁻³
475 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint

Special details top

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

	x	y	z	U_iso*/U_eq
O51	0.50535 (17)	0.7077 (6)	0.24808 (9)	0.0691 (10)
O21	0.70397 (15)	0.5456 (6)	0.50326 (9)	0.0573 (8)
O31	0.61522 (16)	0.5865 (6)	0.41837 (9)	0.0687 (10)
O42	0.27703 (15)	0.5291 (6)	0.64753 (9)	0.0573 (8)
O61	0.53510 (17)	0.4133 (6)	0.29097 (10)	0.0651 (9)
H61	0.549189	0.395076	0.315978	0.098*
O52	0.35044 (19)	0.3351 (7)	0.77537 (10)	0.0782 (11)
O22	0.50666 (16)	0.4568 (7)	0.84892 (10)	0.0673 (9)
N2	0.50604 (16)	0.1561 (7)	0.78717 (10)	0.0497 (9)
H2A	0.489314	0.259093	0.767724	0.060*
H2B	0.481505	0.141163	0.806772	0.060*
H2C	0.510002	0.016662	0.775088	0.060*
O12	0.60547 (17)	0.5616 (8)	0.85091 (12)	0.0804 (11)
H12	0.596777	0.661551	0.867538	0.121*
O53	0.41502 (16)	0.1536 (6)	−0.06420 (9)	0.0683 (10)
O33	0.41593 (17)	−0.0613 (7)	0.10769 (10)	0.0723 (10)
O62	0.32283 (18)	0.5688 (6)	0.72122 (9)	0.0650 (9)
H62	0.306313	0.558689	0.696514	0.097*
O63	0.4257 (2)	−0.1560 (7)	−0.02369 (10)	0.0898 (13)
H63	0.426652	−0.187738	0.001323	0.135*
N3	0.91743 (16)	0.1033 (7)	0.89676 (10)	0.0530 (9)
H3A	0.948825	0.089238	0.882157	0.064*
H3B	0.911349	−0.033859	0.909005	0.064*
H3C	0.926504	0.213913	0.916445	0.064*
O13	0.82759 (17)	0.4597 (8)	0.81648 (11)	0.0826 (11)
H13	0.838510	0.560027	0.800741	0.124*
O32	0.25223 (18)	0.2403 (6)	0.60170 (9)	0.0714 (10)
O11	0.64245 (18)	0.2533 (7)	0.47396 (10)	0.0747 (11)
H11	0.632696	0.349836	0.455050	0.112*
O41	0.58195 (16)	0.3597 (6)	0.36366 (10)	0.0611 (9)
O23	0.92909 (18)	0.4439 (7)	0.84202 (11)	0.0773 (11)
O43	0.4306 (3)	−0.2474 (7)	0.05052 (11)	0.1063 (17)
C92	0.3091 (3)	0.1500 (9)	0.71221 (14)	0.0623 (13)
H92	0.313909	0.008333	0.726991	0.075*
C21	0.69223 (19)	0.1997 (9)	0.54397 (12)	0.0479 (11)
H21	0.693864	0.033386	0.535817	0.057*
C102	0.3284 (2)	0.3616 (9)	0.73773 (13)	0.0553 (12)
C91	0.5491 (3)	0.8104 (8)	0.31681 (14)	0.0634 (14)
H91	0.543330	0.967160	0.308525	0.076*
N1	0.75303 (16)	0.2713 (7)	0.56779 (10)	0.0514 (9)
H1A	0.782947	0.239898	0.552589	0.062*
H1B	0.760194	0.191760	0.591977	0.062*
H1C	0.752571	0.425311	0.573163	0.062*
C71	0.5913 (2)	0.5622 (9)	0.38116 (13)	0.0533 (11)
C101	0.5285 (2)	0.6349 (9)	0.28288 (14)	0.0549 (12)
C93	0.4222 (2)	0.2229 (9)	0.00818 (13)	0.0569 (12)
H93	0.422124	0.383360	0.002075	0.068*
C12	0.5562 (2)	0.4343 (9)	0.83763 (12)	0.0507 (11)
C22	0.5688 (2)	0.2423 (8)	0.80726 (12)	0.0469 (10)
H22	0.590026	0.112391	0.823804	0.056*
C83	0.4238 (2)	0.1728 (8)	0.04899 (14)	0.0556 (12)
H83	0.425433	0.303496	0.066662	0.067*
C73	0.4234 (2)	−0.0578 (9)	0.07048 (14)	0.0597 (12)
C72	0.2707 (2)	0.3086 (9)	0.63806 (14)	0.0551 (12)
C81	0.5743 (2)	0.7805 (8)	0.35685 (14)	0.0591 (13)
H81	0.582571	0.919478	0.372108	0.071*
C103	0.4204 (2)	0.0676 (10)	−0.02892 (14)	0.0569 (12)
C13	0.8771 (3)	0.3733 (9)	0.84087 (13)	0.0568 (12)
C82	0.2861 (3)	0.1290 (8)	0.67188 (14)	0.0647 (14)
H82	0.278161	−0.025727	0.662983	0.078*
C11	0.6811 (2)	0.3523 (9)	0.50484 (13)	0.0513 (11)
C32	0.6087 (2)	0.3153 (9)	0.77448 (14)	0.0555 (12)
H32A	0.587200	0.440369	0.757417	0.067*
H32B	0.647301	0.380623	0.789097	0.067*
C43	0.7844 (3)	0.0432 (13)	0.9183 (2)	0.0860 (19)
H43	0.820501	−0.032605	0.935136	0.103*
C41	0.5780 (3)	0.1439 (12)	0.5544 (2)	0.0834 (18)
H41	0.564470	0.223911	0.527432	0.100*
C23	0.8598 (2)	0.1713 (8)	0.86775 (12)	0.0501 (11)
H23	0.846419	0.037083	0.849303	0.060*
C61	0.5320 (3)	0.2097 (19)	0.5841 (3)	0.143 (4)
H61A	0.543090	0.128473	0.610435	0.214*
H61B	0.490707	0.164821	0.571522	0.214*
H61C	0.533419	0.376904	0.588916	0.214*
C63	0.7479 (4)	−0.1431 (14)	0.8909 (3)	0.140 (3)
H63A	0.712509	−0.071302	0.874072	0.211*
H63B	0.734101	−0.262623	0.908534	0.211*
H63C	0.774050	−0.213274	0.872817	0.211*
C33	0.8074 (2)	0.2356 (10)	0.89208 (14)	0.0567 (12)
H33A	0.821389	0.366630	0.910613	0.068*
H33B	0.772441	0.291143	0.872015	0.068*
C31	0.6421 (2)	0.2334 (11)	0.57159 (14)	0.0635 (14)
H31A	0.655757	0.155619	0.598352	0.076*
H31B	0.638985	0.400694	0.577303	0.076*
C51	0.5769 (4)	−0.1164 (16)	0.5459 (4)	0.156 (4)
H51A	0.593915	−0.198940	0.571228	0.235*
H51B	0.601387	−0.150233	0.524196	0.235*
H51C	0.534808	−0.166653	0.536933	0.235*
C53	0.7448 (3)	0.1537 (18)	0.9482 (2)	0.128 (3)
H53A	0.710409	0.236004	0.932178	0.193*
H53B	0.769616	0.262754	0.966570	0.193*
H53C	0.729400	0.032305	0.964690	0.193*
C62	0.6692 (4)	−0.0556 (14)	0.7678 (3)	0.132 (3)
H62A	0.705212	0.024075	0.782270	0.198*
H62B	0.681535	−0.163144	0.747492	0.198*
H62C	0.649296	−0.141553	0.787741	0.198*
C42	0.6243 (3)	0.1235 (12)	0.74541 (18)	0.0819 (19)
H42	0.585740	0.041705	0.733759	0.098*
C52	0.6518 (4)	0.2342 (19)	0.7090 (2)	0.131 (3)
H52A	0.622970	0.347316	0.694788	0.196*
H52B	0.659386	0.113250	0.689480	0.196*
H52C	0.690189	0.311730	0.719796	0.196*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51	0.099 (3)	0.065 (2)	0.0380 (17)	0.000 (2)	−0.0088 (16)	0.0087 (16)
O21	0.071 (2)	0.060 (2)	0.0379 (16)	−0.0130 (19)	0.0005 (14)	0.0086 (15)
O31	0.090 (2)	0.072 (2)	0.0375 (17)	−0.007 (2)	−0.0086 (16)	0.0078 (17)
O42	0.088 (2)	0.0441 (19)	0.0372 (15)	0.0084 (17)	0.0001 (15)	0.0040 (14)
O61	0.099 (3)	0.045 (2)	0.0445 (17)	0.0002 (19)	−0.0105 (18)	−0.0001 (15)
O52	0.123 (3)	0.061 (2)	0.0431 (18)	−0.009 (2)	−0.0092 (19)	0.0057 (17)
O22	0.075 (2)	0.075 (2)	0.058 (2)	0.000 (2)	0.0272 (18)	−0.0160 (18)
N2	0.064 (2)	0.051 (2)	0.0349 (17)	−0.0007 (19)	0.0099 (16)	−0.0023 (17)
O12	0.090 (3)	0.085 (3)	0.070 (2)	−0.023 (2)	0.0235 (19)	−0.036 (2)
O53	0.093 (2)	0.074 (2)	0.0365 (17)	−0.001 (2)	0.0059 (16)	0.0077 (17)
O33	0.113 (3)	0.064 (2)	0.0410 (17)	0.011 (2)	0.0151 (18)	0.0093 (17)
O62	0.108 (3)	0.0441 (19)	0.0378 (16)	0.0020 (19)	−0.0036 (17)	0.0016 (15)
O63	0.173 (4)	0.054 (2)	0.0394 (18)	0.011 (3)	0.007 (2)	−0.0044 (17)
N3	0.069 (2)	0.056 (2)	0.0368 (18)	0.002 (2)	0.0143 (17)	−0.0023 (17)
O13	0.093 (3)	0.090 (3)	0.062 (2)	−0.001 (2)	0.002 (2)	0.033 (2)
O32	0.111 (3)	0.057 (2)	0.0387 (17)	0.002 (2)	−0.0087 (17)	−0.0035 (16)
O11	0.098 (3)	0.073 (2)	0.0441 (18)	−0.025 (2)	−0.0155 (18)	0.0124 (18)
O41	0.085 (2)	0.0442 (18)	0.0495 (18)	−0.0022 (17)	−0.0056 (16)	0.0073 (16)
O23	0.081 (3)	0.086 (3)	0.069 (2)	−0.010 (2)	0.023 (2)	0.023 (2)
O43	0.229 (5)	0.042 (2)	0.050 (2)	0.020 (3)	0.027 (3)	0.0039 (18)
C92	0.104 (4)	0.039 (3)	0.043 (3)	0.003 (3)	0.008 (3)	0.002 (2)
C21	0.056 (3)	0.051 (3)	0.036 (2)	0.001 (2)	0.0056 (19)	0.007 (2)
C102	0.078 (3)	0.052 (3)	0.034 (2)	0.005 (3)	0.003 (2)	0.007 (2)
C91	0.098 (4)	0.037 (3)	0.048 (3)	0.002 (3)	−0.010 (3)	0.001 (2)
N1	0.067 (2)	0.055 (2)	0.0309 (17)	0.007 (2)	0.0028 (16)	0.0039 (16)
C71	0.066 (3)	0.054 (3)	0.037 (2)	−0.001 (3)	0.001 (2)	0.004 (2)
C101	0.067 (3)	0.051 (3)	0.044 (3)	0.000 (2)	0.002 (2)	0.006 (2)
C93	0.083 (3)	0.043 (3)	0.044 (2)	0.002 (3)	0.007 (2)	0.000 (2)
C12	0.072 (3)	0.049 (3)	0.031 (2)	−0.004 (3)	0.009 (2)	−0.004 (2)
C22	0.059 (3)	0.049 (3)	0.033 (2)	−0.002 (2)	0.0083 (18)	−0.002 (2)
C83	0.081 (3)	0.041 (3)	0.043 (2)	0.003 (2)	0.006 (2)	−0.003 (2)
C73	0.088 (4)	0.050 (3)	0.038 (2)	0.004 (3)	0.003 (2)	0.006 (2)
C72	0.072 (3)	0.051 (3)	0.041 (2)	0.001 (2)	0.006 (2)	0.001 (2)
C81	0.089 (4)	0.038 (3)	0.046 (2)	−0.001 (2)	−0.006 (2)	−0.003 (2)
C103	0.072 (3)	0.053 (3)	0.045 (3)	0.002 (3)	0.005 (2)	−0.001 (2)
C13	0.079 (3)	0.056 (3)	0.037 (2)	0.000 (3)	0.015 (2)	0.003 (2)
C82	0.107 (4)	0.040 (3)	0.045 (3)	−0.004 (3)	0.004 (3)	0.000 (2)
C11	0.056 (3)	0.065 (3)	0.034 (2)	−0.002 (3)	0.008 (2)	0.005 (2)
C32	0.061 (3)	0.062 (3)	0.047 (2)	−0.003 (2)	0.018 (2)	−0.005 (2)
C43	0.073 (4)	0.098 (5)	0.092 (4)	0.012 (4)	0.029 (3)	0.039 (4)
C41	0.069 (4)	0.094 (5)	0.090 (4)	0.004 (3)	0.020 (3)	0.022 (4)
C23	0.065 (3)	0.052 (3)	0.033 (2)	−0.003 (2)	0.0081 (19)	0.001 (2)
C61	0.101 (5)	0.174 (9)	0.171 (8)	0.017 (6)	0.078 (5)	0.025 (8)
C63	0.131 (6)	0.073 (5)	0.235 (11)	−0.030 (5)	0.084 (7)	−0.010 (6)
C33	0.061 (3)	0.064 (3)	0.045 (2)	−0.003 (3)	0.009 (2)	−0.001 (2)
C31	0.075 (3)	0.075 (4)	0.044 (2)	0.010 (3)	0.021 (2)	0.011 (3)
C51	0.103 (6)	0.104 (7)	0.263 (12)	−0.030 (5)	0.032 (6)	−0.013 (8)
C53	0.112 (5)	0.183 (9)	0.103 (5)	−0.001 (6)	0.057 (4)	0.022 (6)
C62	0.161 (7)	0.074 (5)	0.185 (8)	0.029 (5)	0.106 (6)	0.004 (6)
C42	0.080 (4)	0.100 (5)	0.073 (4)	−0.023 (4)	0.036 (3)	−0.034 (4)
C52	0.141 (6)	0.192 (9)	0.073 (4)	0.004 (7)	0.063 (4)	−0.007 (5)

Geometric parameters (Å, º) top

O51—C101	1.223 (5)	C93—C103	1.477 (6)
O21—C11	1.207 (6)	C12—C22	1.514 (6)
O31—C71	1.234 (5)	C22—H22	0.9800
O42—C72	1.288 (6)	C22—C32	1.521 (6)
O61—H61	0.8200	C83—H83	0.9300
O61—C101	1.286 (6)	C83—C73	1.478 (7)
O52—C102	1.238 (5)	C72—C82	1.488 (6)
O22—C12	1.197 (5)	C81—H81	0.9300
N2—H2A	0.8900	C13—C23	1.516 (7)
N2—H2B	0.8900	C82—H82	0.9300
N2—H2C	0.8900	C32—H32A	0.9700
N2—C22	1.499 (5)	C32—H32B	0.9700
O12—H12	0.8200	C32—C42	1.505 (7)
O12—C12	1.307 (5)	C43—H43	0.9800
O53—C103	1.221 (5)	C43—C63	1.516 (10)
O33—C73	1.231 (5)	C43—C33	1.510 (8)
O62—H62	0.8200	C43—C53	1.520 (9)
O62—C102	1.286 (6)	C41—H41	0.9800
O63—H63	0.8200	C41—C61	1.531 (9)
O63—C103	1.281 (6)	C41—C31	1.506 (8)
N3—H3A	0.8900	C41—C51	1.499 (11)
N3—H3B	0.8900	C23—H23	0.9800
N3—H3C	0.8900	C23—C33	1.523 (6)
N3—C23	1.491 (5)	C61—H61A	0.9600
O13—H13	0.8200	C61—H61B	0.9600
O13—C13	1.323 (6)	C61—H61C	0.9600
O32—C72	1.236 (5)	C63—H63A	0.9600
O11—H11	0.8200	C63—H63B	0.9600
O11—C11	1.321 (5)	C63—H63C	0.9600
O41—C71	1.280 (6)	C33—H33A	0.9700
O23—C13	1.194 (6)	C33—H33B	0.9700
O43—C73	1.273 (6)	C31—H31A	0.9700
C92—H92	0.9300	C31—H31B	0.9700
C92—C102	1.476 (7)	C51—H51A	0.9600
C92—C82	1.318 (6)	C51—H51B	0.9600
C21—H21	0.9800	C51—H51C	0.9600
C21—N1	1.478 (5)	C53—H53A	0.9600
C21—C11	1.513 (6)	C53—H53B	0.9600
C21—C31	1.521 (6)	C53—H53C	0.9600
C91—H91	0.9300	C62—H62A	0.9600
C91—C101	1.491 (6)	C62—H62B	0.9600
C91—C81	1.327 (6)	C62—H62C	0.9600
N1—H1A	0.8900	C62—C42	1.509 (10)
N1—H1B	0.8900	C42—H42	0.9800
N1—H1C	0.8900	C42—C52	1.528 (9)
C71—C81	1.479 (7)	C52—H52A	0.9600
C93—H93	0.9300	C52—H52B	0.9600
C93—C83	1.335 (6)	C52—H52C	0.9600

C101—O61—H61	109.5	O11—C11—C21	112.4 (4)
H2A—N2—H2B	109.5	C22—C32—H32A	108.2
H2A—N2—H2C	109.5	C22—C32—H32B	108.2
H2B—N2—H2C	109.5	H32A—C32—H32B	107.4
C22—N2—H2A	109.5	C42—C32—C22	116.2 (4)
C22—N2—H2B	109.5	C42—C32—H32A	108.2
C22—N2—H2C	109.5	C42—C32—H32B	108.2
C12—O12—H12	109.5	C63—C43—H43	108.5
C102—O62—H62	109.5	C63—C43—C53	110.8 (6)
C103—O63—H63	109.5	C33—C43—H43	108.5
H3A—N3—H3B	109.5	C33—C43—C63	111.6 (5)
H3A—N3—H3C	109.5	C33—C43—C53	108.9 (6)
H3B—N3—H3C	109.5	C53—C43—H43	108.5
C23—N3—H3A	109.5	C61—C41—H41	107.5
C23—N3—H3B	109.5	C31—C41—H41	107.5
C23—N3—H3C	109.5	C31—C41—C61	110.3 (6)
C13—O13—H13	109.5	C51—C41—H41	107.5
C11—O11—H11	109.5	C51—C41—C61	111.0 (7)
C102—C92—H92	114.7	C51—C41—C31	112.6 (6)
C82—C92—H92	114.7	N3—C23—C13	107.0 (4)
C82—C92—C102	130.5 (5)	N3—C23—H23	108.6
N1—C21—H21	109.6	N3—C23—C33	111.4 (3)
N1—C21—C11	106.7 (4)	C13—C23—H23	108.6
N1—C21—C31	109.2 (4)	C13—C23—C33	112.5 (4)
C11—C21—H21	109.6	C33—C23—H23	108.6
C11—C21—C31	112.1 (4)	C41—C61—H61A	109.5
C31—C21—H21	109.6	C41—C61—H61B	109.5
O52—C102—O62	120.7 (4)	C41—C61—H61C	109.5
O52—C102—C92	118.5 (4)	H61A—C61—H61B	109.5
O62—C102—C92	120.8 (4)	H61A—C61—H61C	109.5
C101—C91—H91	114.6	H61B—C61—H61C	109.5
C81—C91—H91	114.6	C43—C63—H63A	109.5
C81—C91—C101	130.8 (4)	C43—C63—H63B	109.5
C21—N1—H1A	109.5	C43—C63—H63C	109.5
C21—N1—H1B	109.5	H63A—C63—H63B	109.5
C21—N1—H1C	109.5	H63A—C63—H63C	109.5
H1A—N1—H1B	109.5	H63B—C63—H63C	109.5
H1A—N1—H1C	109.5	C43—C33—C23	116.9 (5)
H1B—N1—H1C	109.5	C43—C33—H33A	108.1
O31—C71—O41	122.6 (5)	C43—C33—H33B	108.1
O31—C71—C81	116.8 (5)	C23—C33—H33A	108.1
O41—C71—C81	120.6 (4)	C23—C33—H33B	108.1
O51—C101—O61	122.0 (4)	H33A—C33—H33B	107.3
O51—C101—C91	118.4 (4)	C21—C31—H31A	108.1
O61—C101—C91	119.5 (4)	C21—C31—H31B	108.1
C83—C93—H93	114.4	C41—C31—C21	116.8 (4)
C83—C93—C103	131.1 (5)	C41—C31—H31A	108.1
C103—C93—H93	114.4	C41—C31—H31B	108.1
O22—C12—O12	125.0 (4)	H31A—C31—H31B	107.3
O22—C12—C22	122.2 (4)	C41—C51—H51A	109.5
O12—C12—C22	112.7 (4)	C41—C51—H51B	109.5
N2—C22—C12	105.5 (4)	C41—C51—H51C	109.5
N2—C22—H22	108.0	H51A—C51—H51B	109.5
N2—C22—C32	111.7 (3)	H51A—C51—H51C	109.5
C12—C22—H22	108.0	H51B—C51—H51C	109.5
C12—C22—C32	115.5 (4)	C43—C53—H53A	109.5
C32—C22—H22	108.0	C43—C53—H53B	109.5
C93—C83—H83	114.9	C43—C53—H53C	109.5
C93—C83—C73	130.1 (4)	H53A—C53—H53B	109.5
C73—C83—H83	114.9	H53A—C53—H53C	109.5
O33—C73—O43	121.3 (5)	H53B—C53—H53C	109.5
O33—C73—C83	118.6 (5)	H62A—C62—H62B	109.5
O43—C73—C83	120.1 (4)	H62A—C62—H62C	109.5
O42—C72—C82	119.2 (4)	H62B—C62—H62C	109.5
O32—C72—O42	122.2 (4)	C42—C62—H62A	109.5
O32—C72—C82	118.5 (4)	C42—C62—H62B	109.5
C91—C81—C71	130.5 (4)	C42—C62—H62C	109.5
C91—C81—H81	114.7	C32—C42—C62	112.5 (5)
C71—C81—H81	114.7	C32—C42—H42	108.4
O53—C103—O63	120.7 (5)	C32—C42—C52	109.3 (6)
O53—C103—C93	119.8 (5)	C62—C42—H42	108.4
O63—C103—C93	119.6 (4)	C62—C42—C52	109.8 (6)
O13—C13—C23	111.4 (5)	C52—C42—H42	108.4
O23—C13—O13	125.1 (5)	C42—C52—H52A	109.5
O23—C13—C23	123.6 (5)	C42—C52—H52B	109.5
C92—C82—C72	131.5 (5)	C42—C52—H52C	109.5
C92—C82—H82	114.3	H52A—C52—H52B	109.5
C72—C82—H82	114.3	H52A—C52—H52C	109.5
O21—C11—O11	124.9 (4)	H52B—C52—H52C	109.5
O21—C11—C21	122.7 (4)

O31—C71—C81—C91	178.9 (6)	C93—C83—C73—O43	10.5 (9)
O42—C72—C82—C92	−3.6 (9)	C12—C22—C32—C42	177.1 (4)
O22—C12—C22—N2	16.5 (6)	C22—C32—C42—C62	−70.0 (6)
O22—C12—C22—C32	140.4 (5)	C22—C32—C42—C52	167.8 (5)
N2—C22—C32—C42	−62.4 (6)	C83—C93—C103—O53	175.2 (5)
O12—C12—C22—N2	−166.2 (4)	C83—C93—C103—O63	−5.9 (9)
O12—C12—C22—C32	−42.3 (6)	C81—C91—C101—O51	178.7 (6)
N3—C23—C33—C43	−62.7 (6)	C81—C91—C101—O61	−0.7 (9)
O13—C13—C23—N3	−174.6 (4)	C103—C93—C83—C73	−1.1 (9)
O13—C13—C23—C33	−51.9 (5)	C13—C23—C33—C43	177.2 (5)
O32—C72—C82—C92	176.5 (6)	C82—C92—C102—O52	−178.0 (6)
O41—C71—C81—C91	−0.3 (9)	C82—C92—C102—O62	1.4 (10)
O23—C13—C23—N3	5.2 (6)	C11—C21—C31—C41	68.7 (6)
O23—C13—C23—C33	127.9 (5)	C61—C41—C31—C21	−175.2 (6)
C102—C92—C82—C72	−1.0 (11)	C63—C43—C33—C23	−71.4 (6)
N1—C21—C11—O21	−26.2 (6)	C31—C21—C11—O21	93.3 (6)
N1—C21—C11—O11	156.1 (4)	C31—C21—C11—O11	−84.4 (5)
N1—C21—C31—C41	−173.3 (5)	C51—C41—C31—C21	60.1 (8)
C101—C91—C81—C71	1.1 (11)	C53—C43—C33—C23	165.9 (5)
C93—C83—C73—O33	−169.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O61—H61···O41	0.82	1.60	2.415 (4)	176
N2—H2A···O61ⁱ	0.89	2.07	2.918 (4)	159
N2—H2B···O23ⁱⁱ	0.89	2.06	2.875 (5)	152
N2—H2C···O51ⁱⁱⁱ	0.89	1.91	2.776 (5)	164
O12—H12···O33^iv	0.82	1.80	2.596 (5)	163
O62—H62···O42	0.82	1.61	2.430 (4)	177
O63—H63···O43	0.82	1.60	2.424 (5)	178
N3—H3A···O22^v	0.89	1.92	2.782 (5)	162
N3—H3B···O53^vi	0.89	1.96	2.843 (5)	169
N3—H3C···O63^vii	0.89	2.06	2.875 (5)	152
O13—H13···O52^viii	0.82	1.80	2.592 (5)	163
O11—H11···O31	0.82	1.79	2.602 (5)	173
N1—H1A···O21^ix	0.89	2.16	2.894 (5)	139
N1—H1A···O31^ix	0.89	2.43	3.018 (5)	124
N1—H1B···O42^v	0.89	1.99	2.879 (4)	177
N1—H1C···O32^viii	0.89	2.01	2.873 (5)	164

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