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We report the crystal structures of three matrine derivatives, namely, the salts (1R,2R,9S,17S)-6-oxo-7,13-di­aza­tetra­cyclo­[7.7.1.02,7.013,17]hepta­decan-13-ium (2E)-3-(3,4-di­hydroxy­phen­yl)prop-2-enoate (matrine caffeinate) sesquihydrate, C15H25N2O+·C9H7O4·1.5H2O (Matrine–CA), and the 2-hy­droxy­benzoate (sali­cylate) monohydrate, C15H25N2O+·C7H5O3·H2O (Matrine–SA), as well as the 1.75-hydrate form, (1R,2R,9S,17S)-7,13-di­aza­tetra­cyclo­[7.7.1.02,7.013,17]hep­ta­decan-6-one 1.75-hydrate, C15H24N2O·1.75H2O (Matrine–H). Each derivative exhibited a consistent mol­ecular conformation for the matrine core, which is notably distinct from that of the anhydrous form. Notably, both salts crystallized in the ortho­rhom­bic space group P212121, with an asymmetric unit featuring one cation and one anion. Within the two salt structures, inter­molecular proton transfer between matrine and the acid is observed, culminating in the formation of a matrine cation protonated at the tertiary amine N site. The Matrine–CA crystal packing is manifested as a three-dimensional (3D) network arising from one-dimensional (1D) supra­molecular helical chains, stabilized by N—H...O and O—H...O hy­dro­gen bonds. In the case of Matrine–SA, the matrine cation is inter­connected via hy­dro­gen bonds with salicylate anions and water mol­ecules, also forming a 1D helical motif. The structure of the hydrate form, Matrine–H, is reported again with the disordered solvent mol­ecules accurately located. To further elucidate the structural attributes, Hirshfeld surface analysis and fingerprint plots are employed, offering a nuanced perspective on the inter­molecular contacts and inter­actions within these crystalline forms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624008064/op3032sup1.cif
Contains datablocks matrine-ca, matrine-sa, matrine-h, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624008064/op3032matrine-casup2.hkl
Contains datablock matrine-ca

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624008064/op3032matrine-sasup3.hkl
Contains datablock matrine-sa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624008064/op3032matrine-hsup4.hkl
Contains datablock matrine-h

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624008064/op3032matrine-casup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624008064/op3032matrine-sasup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624008064/op3032matrine-hsup7.cml
Supplementary material

CCDC references: 2362540; 2362541; 2362542

Computing details top

(1R,2R,9S,17S)-6-Oxo-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-13-ium (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate sesquihydrate (matrine-ca) top
Crystal data top
C15H25N2O+·C9H7O4·1.5H2ODx = 1.312 Mg m3
Mr = 455.54Ga Kα radiation, λ = 1.34139 Å
Orthorhombic, P212121Cell parameters from 9998 reflections
a = 8.1508 (4) Åθ = 3.8–60.5°
b = 11.0066 (5) ŵ = 0.50 mm1
c = 25.7084 (12) ÅT = 170 K
V = 2306.37 (19) Å3Block, colourless
Z = 40.05 × 0.04 × 0.03 mm
F(000) = 980
Data collection top
Bruker D8 Venture
diffractometer
4863 reflections with I > 2σ(I)
ω and φ scansRint = 0.059
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 60.7°, θmin = 3.8°
Tmin = 0.699, Tmax = 0.752h = 1010
43143 measured reflectionsk = 1414
5269 independent reflectionsl = 3333
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0585P)2 + 0.1825P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.17 e Å3
5269 reflectionsΔρmin = 0.26 e Å3
316 parametersAbsolute structure: Flack x determined using 1970 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
6 restraintsAbsolute structure parameter: 0.07 (7)
Primary atom site location: dual
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.

Refinement. Single-crystal X-ray diffraction (SCXRD) data were collected on a Bruker D8 Venture diffractometer (Bruker, Ettlingen, Germany) with Ga Kα (λ = 1.34139 Å) radiation. Using OLEX2, the crystal structure was solved using intrinsic phasing methods (SHELXT) and refined with full-matrix least-squares methods with anisotropic thermal parameters for all non-H atoms on F2 using the SHELXL package. Crystal data, data collection and structure refinement details are summarized in Table 1 and hydrogen bonding parameters detailed in Tables 2–4.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.5438 (3)0.53361 (16)0.49236 (6)0.0520 (5)
N10.53019 (19)0.92335 (13)0.34514 (6)0.0235 (3)
H10.4381450.8633960.3467190.028*
C10.4718 (3)1.04146 (18)0.36834 (9)0.0344 (5)
H1A0.3796721.0738180.3474340.041*
H1B0.5620111.1016970.3675180.041*
N20.5827 (2)0.63595 (15)0.41774 (6)0.0270 (4)
C20.4164 (3)1.0225 (2)0.42375 (9)0.0397 (5)
H2A0.3225130.9654680.4243270.048*
H2B0.3791831.1008760.4385150.048*
C30.5556 (3)0.9716 (2)0.45698 (9)0.0395 (5)
H3A0.5137070.9536590.4922980.047*
H3B0.6430871.0335120.4602470.047*
C40.6281 (3)0.8558 (2)0.43348 (8)0.0309 (4)
H40.7317780.8376760.4527710.037*
C50.6738 (2)0.87313 (17)0.37614 (7)0.0250 (4)
H50.7646460.9340340.3744960.030*
C60.5756 (3)0.94248 (18)0.28915 (8)0.0302 (4)
H6A0.6627691.0048710.2868060.036*
H6B0.4787810.9725560.2697870.036*
C70.6356 (3)0.82540 (19)0.26464 (7)0.0295 (4)
H7A0.6690020.8410910.2282240.035*
H7B0.5453890.7652220.2642020.035*
C80.7805 (2)0.77397 (18)0.29480 (7)0.0275 (4)
H8A0.8744990.8306420.2921710.033*
H8B0.8139620.6955660.2791870.033*
C90.7374 (2)0.75436 (17)0.35245 (7)0.0242 (4)
H90.8424130.7348120.3707130.029*
C100.6217 (2)0.64554 (17)0.36138 (7)0.0229 (4)
H100.5172280.6612280.3421280.028*
C110.5140 (3)0.74717 (19)0.44099 (8)0.0317 (4)
H11A0.4958060.7338550.4786350.038*
H11B0.4064930.7649980.4247760.038*
C120.5834 (3)0.5327 (2)0.44574 (8)0.0328 (5)
C130.6315 (3)0.4153 (2)0.42007 (9)0.0377 (5)
H13A0.5643760.3486700.4347730.045*
H13B0.7478640.3978250.4281220.045*
C140.6092 (3)0.41761 (18)0.36135 (8)0.0309 (4)
H14A0.6559630.3430910.3456940.037*
H14B0.4910320.4213400.3525460.037*
C150.6965 (2)0.52851 (18)0.34053 (8)0.0287 (4)
H15A0.6902210.5285960.3020700.034*
H15B0.8137400.5248290.3504780.034*
O20.11594 (18)0.14923 (12)0.32599 (5)0.0266 (3)
O30.0428 (2)0.07081 (13)0.42002 (6)0.0364 (4)
H30.016 (4)0.055 (3)0.4504 (6)0.055*
O40.20784 (19)0.75778 (12)0.25842 (5)0.0313 (3)
O50.25683 (17)0.77954 (12)0.34258 (5)0.0268 (3)
C160.0296 (2)0.33722 (15)0.34039 (7)0.0200 (3)
H160.0050980.3642770.3061760.024*
C170.0248 (2)0.22420 (16)0.35669 (7)0.0203 (3)
C180.0132 (2)0.18249 (16)0.40686 (7)0.0233 (4)
C190.1048 (2)0.25604 (17)0.44005 (7)0.0255 (4)
H190.1309570.2284490.4740740.031*
C200.1583 (2)0.36992 (17)0.42352 (7)0.0228 (4)
H200.2211940.4192100.4463920.027*
C210.1209 (2)0.41239 (15)0.37391 (7)0.0200 (3)
C220.1730 (2)0.53495 (16)0.35921 (7)0.0206 (3)
H220.2285720.5803540.3852420.025*
C230.1516 (2)0.59053 (16)0.31343 (7)0.0210 (4)
H230.0983840.5481200.2860220.025*
C240.2090 (2)0.71695 (16)0.30435 (7)0.0208 (4)
O60.1538 (2)0.01337 (14)0.28106 (7)0.0414 (4)
H20.140 (4)0.183 (3)0.2974 (7)0.062*
H6C0.159 (4)0.0640 (13)0.2867 (12)0.062*
H6D0.075 (3)0.030 (3)0.3032 (10)0.062*
O70.5728 (6)0.7344 (4)0.56539 (16)0.0626 (11)0.5
H7C0.611 (10)0.743 (7)0.5976 (13)0.094*0.5
H7D0.570 (12)0.663 (4)0.550 (3)0.094*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0879 (14)0.0412 (9)0.0267 (8)0.0028 (9)0.0087 (9)0.0119 (7)
N10.0244 (7)0.0178 (7)0.0282 (8)0.0029 (6)0.0021 (6)0.0008 (6)
C10.0350 (10)0.0192 (9)0.0490 (12)0.0007 (8)0.0026 (9)0.0057 (9)
N20.0350 (9)0.0245 (8)0.0213 (7)0.0049 (7)0.0029 (6)0.0041 (6)
C20.0413 (12)0.0279 (10)0.0497 (13)0.0023 (9)0.0032 (10)0.0133 (10)
C30.0469 (13)0.0370 (11)0.0346 (11)0.0029 (10)0.0003 (10)0.0141 (9)
C40.0347 (10)0.0341 (10)0.0239 (9)0.0013 (9)0.0058 (8)0.0046 (8)
C50.0223 (8)0.0257 (9)0.0269 (9)0.0026 (7)0.0052 (7)0.0021 (7)
C60.0291 (10)0.0296 (10)0.0319 (10)0.0049 (8)0.0018 (8)0.0098 (8)
C70.0314 (10)0.0354 (10)0.0215 (9)0.0073 (8)0.0017 (8)0.0038 (8)
C80.0255 (9)0.0302 (10)0.0269 (10)0.0022 (8)0.0050 (8)0.0022 (8)
C90.0210 (8)0.0283 (9)0.0234 (9)0.0017 (7)0.0016 (7)0.0005 (7)
C100.0242 (8)0.0247 (9)0.0199 (8)0.0038 (7)0.0001 (7)0.0024 (7)
C110.0420 (11)0.0313 (10)0.0216 (8)0.0046 (9)0.0049 (8)0.0014 (8)
C120.0373 (11)0.0328 (10)0.0284 (10)0.0008 (9)0.0009 (8)0.0083 (8)
C130.0442 (12)0.0271 (10)0.0418 (12)0.0051 (9)0.0012 (10)0.0096 (9)
C140.0303 (10)0.0245 (9)0.0379 (11)0.0027 (8)0.0028 (9)0.0002 (8)
C150.0292 (9)0.0249 (9)0.0319 (10)0.0031 (8)0.0052 (8)0.0015 (8)
O20.0328 (7)0.0199 (6)0.0271 (7)0.0060 (6)0.0074 (5)0.0001 (5)
O30.0473 (9)0.0275 (7)0.0345 (7)0.0141 (7)0.0135 (7)0.0122 (6)
O40.0403 (8)0.0267 (7)0.0270 (7)0.0099 (6)0.0092 (6)0.0077 (6)
O50.0289 (6)0.0219 (6)0.0295 (7)0.0073 (5)0.0004 (5)0.0042 (5)
C160.0214 (8)0.0201 (8)0.0184 (8)0.0010 (7)0.0012 (7)0.0010 (6)
C170.0205 (8)0.0184 (8)0.0220 (8)0.0004 (7)0.0015 (7)0.0033 (6)
C180.0259 (9)0.0173 (8)0.0266 (9)0.0008 (7)0.0007 (7)0.0033 (7)
C190.0291 (9)0.0267 (9)0.0206 (8)0.0015 (8)0.0038 (7)0.0028 (7)
C200.0250 (9)0.0222 (8)0.0212 (8)0.0015 (7)0.0020 (7)0.0026 (7)
C210.0202 (8)0.0175 (8)0.0223 (8)0.0004 (7)0.0014 (7)0.0009 (7)
C220.0200 (8)0.0184 (8)0.0235 (8)0.0014 (6)0.0012 (7)0.0024 (7)
C230.0225 (8)0.0190 (8)0.0215 (8)0.0022 (7)0.0020 (7)0.0033 (7)
C240.0163 (7)0.0180 (8)0.0281 (9)0.0008 (6)0.0029 (7)0.0011 (7)
O60.0502 (10)0.0262 (7)0.0478 (9)0.0091 (7)0.0063 (8)0.0064 (7)
O70.066 (3)0.067 (3)0.055 (2)0.013 (2)0.016 (2)0.013 (2)
Geometric parameters (Å, º) top
O1—C121.241 (3)C11—H11A0.9900
N1—H11.0000C11—H11B0.9900
N1—C11.507 (2)C12—C131.503 (3)
N1—C51.520 (2)C13—H13A0.9900
N1—C61.501 (2)C13—H13B0.9900
C1—H1A0.9900C13—C141.521 (3)
C1—H1B0.9900C14—H14A0.9900
C1—C21.509 (3)C14—H14B0.9900
N2—C101.487 (2)C14—C151.511 (3)
N2—C111.473 (3)C15—H15A0.9900
N2—C121.345 (3)C15—H15B0.9900
C2—H2A0.9900O2—C171.362 (2)
C2—H2B0.9900O2—H20.850 (13)
C2—C31.527 (4)O3—H30.831 (13)
C3—H3A0.9900O3—C181.354 (2)
C3—H3B0.9900O4—C241.263 (2)
C3—C41.529 (3)O5—C241.262 (2)
C4—H41.0000C16—H160.9500
C4—C51.532 (3)C16—C171.386 (2)
C4—C111.526 (3)C16—C211.407 (2)
C5—H51.0000C17—C181.404 (2)
C5—C91.533 (3)C18—C191.393 (3)
C6—H6A0.9900C19—H190.9500
C6—H6B0.9900C19—C201.394 (3)
C6—C71.516 (3)C20—H200.9500
C7—H7A0.9900C20—C211.392 (2)
C7—H7B0.9900C21—C221.464 (2)
C7—C81.522 (3)C22—H220.9500
C8—H8A0.9900C22—C231.338 (2)
C8—H8B0.9900C23—H230.9500
C8—C91.539 (3)C23—C241.486 (2)
C9—H91.0000O6—H6C0.865 (13)
C9—C101.541 (3)O6—H6D0.879 (13)
C10—H101.0000O7—H7C0.890 (14)
C10—C151.523 (3)O7—H7D0.881 (14)
C1—N1—H1108.4N2—C10—H10108.2
C1—N1—C5110.43 (15)N2—C10—C15111.63 (15)
C5—N1—H1108.4C9—C10—H10108.2
C6—N1—H1108.4C15—C10—C9111.10 (15)
C6—N1—C1109.65 (15)C15—C10—H10108.2
C6—N1—C5111.35 (15)N2—C11—C4111.57 (17)
N1—C1—H1A109.6N2—C11—H11A109.3
N1—C1—H1B109.6N2—C11—H11B109.3
N1—C1—C2110.41 (17)C4—C11—H11A109.3
H1A—C1—H1B108.1C4—C11—H11B109.3
C2—C1—H1A109.6H11A—C11—H11B108.0
C2—C1—H1B109.6O1—C12—N2120.6 (2)
C11—N2—C10114.68 (14)O1—C12—C13119.92 (19)
C12—N2—C10125.48 (17)N2—C12—C13119.50 (17)
C12—N2—C11119.11 (16)C12—C13—H13A109.0
C1—C2—H2A109.5C12—C13—H13B109.0
C1—C2—H2B109.5C12—C13—C14112.99 (17)
C1—C2—C3110.9 (2)H13A—C13—H13B107.8
H2A—C2—H2B108.1C14—C13—H13A109.0
C3—C2—H2A109.5C14—C13—H13B109.0
C3—C2—H2B109.5C13—C14—H14A110.1
C2—C3—H3A109.2C13—C14—H14B110.1
C2—C3—H3B109.2H14A—C14—H14B108.4
C2—C3—C4111.84 (17)C15—C14—C13107.98 (17)
H3A—C3—H3B107.9C15—C14—H14A110.1
C4—C3—H3A109.2C15—C14—H14B110.1
C4—C3—H3B109.2C10—C15—H15A109.3
C3—C4—H4107.2C10—C15—H15B109.3
C3—C4—C5111.70 (18)C14—C15—C10111.71 (16)
C5—C4—H4107.2C14—C15—H15A109.3
C11—C4—C3111.57 (18)C14—C15—H15B109.3
C11—C4—H4107.2H15A—C15—H15B107.9
C11—C4—C5111.55 (16)C17—O2—H2111 (2)
N1—C5—C4111.27 (16)C18—O3—H3110 (2)
N1—C5—H5107.7C17—C16—H16119.6
N1—C5—C9111.24 (14)C17—C16—C21120.79 (16)
C4—C5—H5107.7C21—C16—H16119.6
C4—C5—C9110.98 (16)O2—C17—C16122.90 (16)
C9—C5—H5107.7O2—C17—C18117.04 (15)
N1—C6—H6A109.4C16—C17—C18120.06 (16)
N1—C6—H6B109.4O3—C18—C17116.88 (16)
N1—C6—C7111.04 (15)O3—C18—C19123.71 (17)
H6A—C6—H6B108.0C19—C18—C17119.40 (16)
C7—C6—H6A109.4C18—C19—H19119.9
C7—C6—H6B109.4C18—C19—C20120.23 (17)
C6—C7—H7A109.5C20—C19—H19119.9
C6—C7—H7B109.5C19—C20—H20119.6
C6—C7—C8110.79 (16)C21—C20—C19120.84 (17)
H7A—C7—H7B108.1C21—C20—H20119.6
C8—C7—H7A109.5C16—C21—C22122.49 (16)
C8—C7—H7B109.5C20—C21—C16118.66 (16)
C7—C8—H8A109.3C20—C21—C22118.82 (16)
C7—C8—H8B109.3C21—C22—H22116.2
C7—C8—C9111.44 (15)C23—C22—C21127.62 (16)
H8A—C8—H8B108.0C23—C22—H22116.2
C9—C8—H8A109.3C22—C23—H23119.2
C9—C8—H8B109.3C22—C23—C24121.68 (16)
C5—C9—C8109.91 (16)C24—C23—H23119.2
C5—C9—H9106.7O4—C24—C23118.52 (16)
C5—C9—C10113.37 (15)O5—C24—O4122.41 (17)
C8—C9—H9106.7O5—C24—C23119.07 (16)
C8—C9—C10113.11 (15)H6C—O6—H6D98 (3)
C10—C9—H9106.7H7C—O7—H7D122 (8)
N2—C10—C9109.32 (15)
O1—C12—C13—C14156.6 (2)C10—N2—C11—C456.8 (2)
N1—C1—C2—C358.8 (2)C10—N2—C12—O1177.6 (2)
N1—C5—C9—C854.9 (2)C10—N2—C12—C131.9 (3)
N1—C5—C9—C1072.74 (19)C11—N2—C10—C955.1 (2)
N1—C6—C7—C856.9 (2)C11—N2—C10—C15178.40 (16)
C1—N1—C5—C456.9 (2)C11—N2—C12—O18.0 (3)
C1—N1—C5—C9178.75 (15)C11—N2—C12—C13171.6 (2)
C1—N1—C6—C7179.75 (16)C11—C4—C5—N173.2 (2)
C1—C2—C3—C454.3 (2)C11—C4—C5—C951.3 (2)
N2—C10—C15—C1442.2 (2)C12—N2—C10—C9134.8 (2)
N2—C12—C13—C1422.9 (3)C12—N2—C10—C1511.5 (3)
C2—C3—C4—C551.2 (3)C12—N2—C11—C4132.40 (19)
C2—C3—C4—C1174.5 (2)C12—C13—C14—C1552.2 (2)
C3—C4—C5—N152.5 (2)C13—C14—C15—C1062.9 (2)
C3—C4—C5—C9176.91 (17)O2—C17—C18—O30.7 (3)
C3—C4—C11—N2179.23 (16)O2—C17—C18—C19179.43 (17)
C4—C5—C9—C8179.40 (15)O3—C18—C19—C20179.83 (19)
C4—C5—C9—C1051.7 (2)C16—C17—C18—O3179.44 (17)
C5—N1—C1—C260.2 (2)C16—C17—C18—C190.4 (3)
C5—N1—C6—C757.2 (2)C16—C21—C22—C233.5 (3)
C5—C4—C11—N253.5 (2)C17—C16—C21—C201.3 (3)
C5—C9—C10—N252.3 (2)C17—C16—C21—C22176.61 (16)
C5—C9—C10—C15175.90 (15)C17—C18—C19—C200.0 (3)
C6—N1—C1—C2176.75 (17)C18—C19—C20—C210.3 (3)
C6—N1—C5—C4179.01 (15)C19—C20—C21—C160.9 (3)
C6—N1—C5—C956.69 (19)C19—C20—C21—C22177.09 (17)
C6—C7—C8—C956.1 (2)C20—C21—C22—C23178.56 (18)
C7—C8—C9—C555.0 (2)C21—C16—C17—O2178.77 (16)
C7—C8—C9—C1072.8 (2)C21—C16—C17—C181.1 (3)
C8—C9—C10—N2178.26 (15)C21—C22—C23—C24178.90 (16)
C8—C9—C10—C1558.1 (2)C22—C23—C24—O4169.44 (18)
C9—C10—C15—C14164.55 (16)C22—C23—C24—O510.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O51.001.752.734 (2)169
O3—H3···O1i0.83 (1)1.83 (2)2.626 (2)160 (3)
O2—H2···O4ii0.85 (1)1.74 (1)2.5879 (19)174 (3)
O6—H6C···O4iii0.87 (1)2.13 (2)2.906 (2)149 (3)
O6—H6D···O20.88 (1)2.12 (2)2.899 (2)148 (3)
O7—H7C···O5iv0.89 (1)1.96 (3)2.806 (4)158 (8)
O7—H7D···O10.88 (1)2.06 (3)2.910 (5)161 (8)
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x, y1/2, z+1/2; (iii) x, y1, z; (iv) x+1/2, y+3/2, z+1.
(1R,2R,9S,17S)-6-Oxo-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-13-ium 2-hydroxybenzoate monohydrate (matrine-sa) top
Crystal data top
C15H25N2O+·C7H5O3·H2ODx = 1.294 Mg m3
Mr = 404.49Ga Kα radiation, λ = 1.34139 Å
Orthorhombic, P212121Cell parameters from 9983 reflections
a = 9.2999 (4) Åθ = 3.7–60.7°
b = 12.7329 (5) ŵ = 0.47 mm1
c = 17.5349 (8) ÅT = 170 K
V = 2076.39 (15) Å3Block, colourless
Z = 40.09 × 0.07 × 0.06 mm
F(000) = 872
Data collection top
Bruker D8 Venture
diffractometer
4568 reflections with I > 2σ(I)
ω and φ scansRint = 0.038
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 60.8°, θmin = 3.7°
Tmin = 0.704, Tmax = 0.752h = 1212
33326 measured reflectionsk = 1616
4679 independent reflectionsl = 2222
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031 w = 1/[σ2(Fo2) + (0.0405P)2 + 0.2725P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.17 e Å3
4679 reflectionsΔρmin = 0.19 e Å3
266 parametersAbsolute structure: Flack x determined using 1920 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.04 (4)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.78504 (13)0.83322 (8)0.79102 (7)0.0378 (3)
O20.42780 (16)0.37680 (11)0.42017 (7)0.0486 (3)
H20.4981890.3592800.4473680.073*
O30.61198 (13)0.39053 (9)0.52537 (7)0.0370 (3)
O40.59618 (11)0.51857 (9)0.61152 (6)0.0330 (2)
O50.63164 (13)1.02448 (11)0.77714 (7)0.0417 (3)
H5A0.5723431.0234390.8154930.063*
H5B0.6819520.9672850.7821060.063*
N10.84031 (13)0.42023 (9)0.66386 (7)0.0242 (2)
H10.7515220.4616160.6523810.029*
N20.76049 (12)0.65766 (9)0.77737 (6)0.0227 (2)
C10.93159 (17)0.41605 (12)0.59299 (8)0.0299 (3)
H1A0.8795080.3778430.5523100.036*
H1B1.0218730.3776890.6038900.036*
C20.96626 (17)0.52600 (13)0.56625 (8)0.0314 (3)
H2A0.8760410.5631380.5531680.038*
H2B1.0264190.5224310.5197430.038*
C31.04610 (17)0.58705 (13)0.62809 (9)0.0330 (3)
H3A1.0584030.6607590.6113500.040*
H3B1.1429610.5562450.6350400.040*
C40.96595 (15)0.58541 (11)0.70476 (8)0.0261 (3)
H41.0344850.6114600.7444270.031*
C50.92096 (15)0.47438 (11)0.72809 (8)0.0249 (3)
H51.0105100.4331860.7381590.030*
C60.7968 (2)0.31069 (11)0.68560 (9)0.0350 (3)
H6A0.8839730.2674870.6936050.042*
H6B0.7409290.2789350.6434230.042*
C70.7068 (2)0.31005 (12)0.75768 (10)0.0380 (4)
H7A0.6837790.2367140.7719400.046*
H7B0.6151910.3475560.7483730.046*
C80.7879 (2)0.36310 (12)0.82286 (9)0.0351 (3)
H8A0.8748460.3216230.8352120.042*
H8B0.7259790.3647880.8687850.042*
C90.83204 (15)0.47536 (11)0.80185 (8)0.0250 (3)
H90.8975360.5004100.8432590.030*
C100.70531 (15)0.55288 (10)0.79893 (7)0.0218 (2)
H100.6371520.5289160.7584000.026*
C110.83793 (15)0.65995 (11)0.70437 (8)0.0249 (3)
H11A0.8719640.7322990.6942890.030*
H11B0.7714320.6398690.6627630.030*
C120.73395 (15)0.74889 (11)0.81362 (8)0.0272 (3)
C130.63792 (19)0.74690 (13)0.88284 (10)0.0355 (3)
H13A0.5810270.8125750.8845010.043*
H13B0.6984000.7444720.9292690.043*
C140.53621 (17)0.65391 (12)0.88326 (9)0.0307 (3)
H14A0.4814260.6521440.9316510.037*
H14B0.4670490.6597520.8405480.037*
C150.62470 (17)0.55474 (12)0.87496 (8)0.0278 (3)
H15A0.5606230.4928040.8781440.033*
H15B0.6946940.5503990.9173840.033*
C160.38377 (17)0.47386 (14)0.44007 (8)0.0352 (3)
C170.27822 (19)0.52336 (19)0.39600 (9)0.0466 (5)
H170.2381620.4880630.3532600.056*
C180.2324 (2)0.62246 (19)0.41420 (11)0.0501 (5)
H180.1605800.6551420.3838520.060*
C190.2893 (2)0.67601 (16)0.47634 (12)0.0463 (4)
H190.2567640.7446860.4886170.056*
C200.39450 (19)0.62748 (13)0.52024 (9)0.0358 (3)
H200.4337630.6636550.5627990.043*
C210.44349 (16)0.52690 (13)0.50307 (8)0.0293 (3)
C220.55864 (15)0.47501 (12)0.54960 (8)0.0279 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0386 (6)0.0233 (5)0.0516 (7)0.0050 (4)0.0145 (5)0.0070 (5)
O20.0569 (8)0.0531 (8)0.0358 (6)0.0184 (6)0.0005 (6)0.0132 (6)
O30.0369 (6)0.0372 (6)0.0367 (6)0.0018 (5)0.0031 (5)0.0040 (5)
O40.0288 (5)0.0440 (6)0.0260 (5)0.0014 (5)0.0042 (4)0.0041 (4)
O50.0391 (6)0.0493 (7)0.0367 (6)0.0085 (6)0.0071 (5)0.0098 (5)
N10.0278 (6)0.0217 (5)0.0230 (5)0.0014 (4)0.0010 (5)0.0040 (4)
N20.0251 (5)0.0213 (5)0.0216 (5)0.0004 (4)0.0017 (4)0.0015 (4)
C10.0318 (7)0.0318 (7)0.0260 (7)0.0022 (6)0.0032 (6)0.0088 (5)
C20.0321 (7)0.0365 (7)0.0257 (6)0.0035 (6)0.0060 (6)0.0061 (6)
C30.0268 (7)0.0390 (8)0.0331 (7)0.0067 (6)0.0076 (6)0.0099 (6)
C40.0218 (6)0.0305 (7)0.0259 (6)0.0026 (5)0.0001 (5)0.0067 (5)
C50.0244 (6)0.0267 (6)0.0237 (6)0.0053 (5)0.0043 (5)0.0048 (5)
C60.0507 (9)0.0200 (6)0.0341 (8)0.0005 (6)0.0018 (7)0.0035 (5)
C70.0569 (10)0.0217 (6)0.0352 (8)0.0046 (7)0.0041 (8)0.0017 (6)
C80.0520 (9)0.0248 (7)0.0286 (7)0.0084 (7)0.0007 (7)0.0051 (5)
C90.0294 (6)0.0248 (6)0.0208 (6)0.0059 (5)0.0042 (5)0.0006 (5)
C100.0243 (6)0.0205 (5)0.0205 (6)0.0006 (5)0.0012 (5)0.0002 (4)
C110.0288 (6)0.0225 (6)0.0236 (6)0.0018 (5)0.0034 (5)0.0011 (5)
C120.0238 (6)0.0251 (6)0.0326 (7)0.0013 (5)0.0014 (5)0.0049 (6)
C130.0397 (8)0.0312 (7)0.0356 (8)0.0004 (7)0.0112 (7)0.0106 (6)
C140.0291 (7)0.0342 (7)0.0287 (7)0.0020 (6)0.0072 (6)0.0005 (6)
C150.0304 (7)0.0295 (6)0.0233 (6)0.0007 (6)0.0026 (5)0.0014 (5)
C160.0340 (7)0.0491 (9)0.0224 (6)0.0189 (7)0.0026 (6)0.0011 (6)
C170.0383 (9)0.0761 (13)0.0254 (7)0.0255 (9)0.0070 (7)0.0102 (8)
C180.0362 (9)0.0725 (13)0.0415 (9)0.0119 (9)0.0087 (7)0.0262 (9)
C190.0418 (9)0.0493 (10)0.0479 (10)0.0006 (8)0.0019 (8)0.0152 (8)
C200.0357 (8)0.0404 (8)0.0314 (7)0.0056 (7)0.0030 (6)0.0032 (6)
C210.0277 (6)0.0388 (8)0.0212 (6)0.0101 (6)0.0008 (5)0.0026 (5)
C220.0255 (6)0.0350 (7)0.0231 (6)0.0086 (6)0.0032 (5)0.0006 (6)
Geometric parameters (Å, º) top
O1—C121.2392 (19)C7—H7B0.9900
O2—H20.8400C7—C81.527 (2)
O2—C161.348 (2)C8—H8A0.9900
O3—C221.2584 (19)C8—H8B0.9900
O4—C221.2683 (18)C8—C91.532 (2)
O5—H5A0.8698C9—H91.0000
O5—H5B0.8701C9—C101.5381 (18)
N1—H11.0000C10—H101.0000
N1—C11.5060 (18)C10—C151.5297 (18)
N1—C51.5186 (17)C11—H11A0.9900
N1—C61.5016 (18)C11—H11B0.9900
N2—C101.4787 (17)C12—C131.507 (2)
N2—C111.4689 (17)C13—H13A0.9900
N2—C121.3470 (18)C13—H13B0.9900
C1—H1A0.9900C13—C141.516 (2)
C1—H1B0.9900C14—H14A0.9900
C1—C21.511 (2)C14—H14B0.9900
C2—H2A0.9900C14—C151.514 (2)
C2—H2B0.9900C15—H15A0.9900
C2—C31.527 (2)C15—H15B0.9900
C3—H3A0.9900C16—C171.399 (3)
C3—H3B0.9900C16—C211.409 (2)
C3—C41.537 (2)C17—H170.9500
C4—H41.0000C17—C181.370 (3)
C4—C51.530 (2)C18—H180.9500
C4—C111.5226 (19)C18—C191.390 (3)
C5—H51.0000C19—H190.9500
C5—C91.5352 (18)C19—C201.390 (3)
C6—H6A0.9900C20—H200.9500
C6—H6B0.9900C20—C211.392 (2)
C6—C71.516 (2)C21—C221.500 (2)
C7—H7A0.9900
C16—O2—H2109.5C5—C9—C10112.95 (11)
H5A—O5—H5B104.5C8—C9—C5109.84 (12)
C1—N1—H1108.5C8—C9—H9106.6
C1—N1—C5110.46 (11)C8—C9—C10113.65 (12)
C5—N1—H1108.5C10—C9—H9106.6
C6—N1—H1108.5N2—C10—C9108.76 (11)
C6—N1—C1109.19 (11)N2—C10—H10108.3
C6—N1—C5111.51 (11)N2—C10—C15112.27 (11)
C11—N2—C10114.26 (10)C9—C10—H10108.3
C12—N2—C10126.43 (11)C15—C10—C9110.88 (11)
C12—N2—C11118.94 (12)C15—C10—H10108.3
N1—C1—H1A109.6N2—C11—C4111.54 (11)
N1—C1—H1B109.6N2—C11—H11A109.3
N1—C1—C2110.09 (11)N2—C11—H11B109.3
H1A—C1—H1B108.2C4—C11—H11A109.3
C2—C1—H1A109.6C4—C11—H11B109.3
C2—C1—H1B109.6H11A—C11—H11B108.0
C1—C2—H2A109.5O1—C12—N2121.74 (13)
C1—C2—H2B109.5O1—C12—C13119.95 (13)
C1—C2—C3110.79 (13)N2—C12—C13118.30 (13)
H2A—C2—H2B108.1C12—C13—H13A109.0
C3—C2—H2A109.5C12—C13—H13B109.0
C3—C2—H2B109.5C12—C13—C14112.76 (12)
C2—C3—H3A109.2H13A—C13—H13B107.8
C2—C3—H3B109.2C14—C13—H13A109.0
C2—C3—C4112.23 (12)C14—C13—H13B109.0
H3A—C3—H3B107.9C13—C14—H14A110.1
C4—C3—H3A109.2C13—C14—H14B110.1
C4—C3—H3B109.2H14A—C14—H14B108.4
C3—C4—H4107.1C15—C14—C13108.17 (13)
C5—C4—C3112.27 (12)C15—C14—H14A110.1
C5—C4—H4107.1C15—C14—H14B110.1
C11—C4—C3111.52 (12)C10—C15—H15A109.4
C11—C4—H4107.1C10—C15—H15B109.4
C11—C4—C5111.30 (11)C14—C15—C10111.28 (11)
N1—C5—C4110.87 (11)C14—C15—H15A109.4
N1—C5—H5107.7C14—C15—H15B109.4
N1—C5—C9111.25 (11)H15A—C15—H15B108.0
C4—C5—H5107.7O2—C16—C17118.89 (16)
C4—C5—C9111.41 (11)O2—C16—C21121.51 (16)
C9—C5—H5107.7C17—C16—C21119.59 (18)
N1—C6—H6A109.3C16—C17—H17119.8
N1—C6—H6B109.3C18—C17—C16120.30 (17)
N1—C6—C7111.44 (11)C18—C17—H17119.8
H6A—C6—H6B108.0C17—C18—H18119.5
C7—C6—H6A109.3C17—C18—C19121.08 (17)
C7—C6—H6B109.3C19—C18—H18119.5
C6—C7—H7A109.6C18—C19—H19120.5
C6—C7—H7B109.6C20—C19—C18118.9 (2)
C6—C7—C8110.43 (16)C20—C19—H19120.5
H7A—C7—H7B108.1C19—C20—H20119.3
C8—C7—H7A109.6C19—C20—C21121.31 (16)
C8—C7—H7B109.6C21—C20—H20119.3
C7—C8—H8A109.3C16—C21—C22119.80 (16)
C7—C8—H8B109.3C20—C21—C16118.78 (15)
C7—C8—C9111.41 (12)C20—C21—C22121.42 (13)
H8A—C8—H8B108.0O3—C22—O4123.67 (15)
C9—C8—H8A109.3O3—C22—C21118.32 (13)
C9—C8—H8B109.3O4—C22—C21118.01 (14)
C5—C9—H9106.6
O1—C12—C13—C14155.09 (15)C7—C8—C9—C1071.83 (17)
O2—C16—C17—C18179.23 (15)C8—C9—C10—N2179.36 (11)
O2—C16—C21—C20179.33 (14)C8—C9—C10—C1556.72 (15)
O2—C16—C21—C220.1 (2)C9—C10—C15—C14160.17 (12)
N1—C1—C2—C359.02 (16)C10—N2—C11—C458.51 (14)
N1—C5—C9—C855.17 (15)C10—N2—C12—O1179.83 (13)
N1—C5—C9—C1072.85 (14)C10—N2—C12—C130.6 (2)
N1—C6—C7—C856.48 (19)C11—N2—C10—C957.32 (14)
N2—C10—C15—C1438.29 (16)C11—N2—C10—C15179.59 (11)
N2—C12—C13—C1424.2 (2)C11—N2—C12—O17.2 (2)
C1—N1—C5—C457.78 (14)C11—N2—C12—C13172.08 (13)
C1—N1—C5—C9177.64 (10)C11—C4—C5—N174.28 (14)
C1—N1—C6—C7178.91 (14)C11—C4—C5—C950.21 (15)
C1—C2—C3—C452.93 (18)C12—N2—C10—C9129.75 (14)
C2—C3—C4—C549.45 (18)C12—N2—C10—C156.66 (19)
C2—C3—C4—C1176.23 (16)C12—N2—C11—C4127.99 (13)
C3—C4—C5—N151.53 (15)C12—C13—C14—C1554.72 (17)
C3—C4—C5—C9176.02 (11)C13—C14—C15—C1062.32 (16)
C3—C4—C11—N2179.46 (11)C16—C17—C18—C190.1 (3)
C4—C5—C9—C8179.45 (12)C16—C21—C22—O38.9 (2)
C4—C5—C9—C1051.42 (15)C16—C21—C22—O4170.70 (13)
C5—N1—C1—C261.78 (15)C17—C16—C21—C200.6 (2)
C5—N1—C6—C756.56 (18)C17—C16—C21—C22178.83 (13)
C5—C4—C11—N253.23 (15)C17—C18—C19—C200.1 (3)
C5—C9—C10—N253.35 (14)C18—C19—C20—C210.0 (3)
C5—C9—C10—C15177.27 (11)C19—C20—C21—C160.4 (2)
C6—N1—C1—C2175.24 (13)C19—C20—C21—C22179.03 (15)
C6—N1—C5—C4179.39 (11)C20—C21—C22—O3170.51 (14)
C6—N1—C5—C956.03 (15)C20—C21—C22—O49.9 (2)
C6—C7—C8—C956.54 (18)C21—C16—C17—C180.4 (2)
C7—C8—C9—C555.81 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.841.772.5233 (19)147
O5—H5A···O4i0.872.022.8820 (16)169
O5—H5B···O10.871.962.8329 (17)176
N1—H1···O41.001.772.7505 (17)167
Symmetry code: (i) x+1, y+1/2, z+3/2.
(1R,2R,9S,17S)-7,13-Diazatetracyclo[7.7.1.0{2,7}.0{13,17}]heptadecan-6-one 1.75-hydrate (matrine-h) top
Crystal data top
C15H24N2O·1.75H2ODx = 1.231 Mg m3
Mr = 279.89Ga Kα radiation, λ = 1.34139 Å
Tetragonal, P43212Cell parameters from 9770 reflections
a = 11.7364 (3) Åθ = 3.7–60.5°
c = 21.9295 (9) ŵ = 0.43 mm1
V = 3020.6 (2) Å3T = 170 K
Z = 8Block, colourless
F(000) = 12280.09 × 0.08 × 0.06 mm
Data collection top
Bruker D8 Venture
diffractometer
3335 reflections with I > 2σ(I)
ω and φ scansRint = 0.042
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 60.8°, θmin = 3.7°
Tmin = 0.698, Tmax = 0.752h = 1515
49632 measured reflectionsk = 1415
3473 independent reflectionsl = 2828
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.5768P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.35 e Å3
3473 reflectionsΔρmin = 0.23 e Å3
192 parametersAbsolute structure: Flack x determined using 1323 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute structure parameter: 0.01 (6)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.63861 (10)0.70536 (11)0.64097 (5)0.0310 (3)
O20.25063 (14)0.96006 (12)0.53692 (7)0.0412 (3)
H2C0.2145140.9051730.5578560.062*
H2D0.2874330.9187590.5092710.062*
O30.1771 (4)1.1412 (5)0.4712 (2)0.0987 (17)0.5
H3C0.1050701.1627010.4652200.148*0.5
H3D0.1864601.0881100.4982700.148*0.5
O40.3131 (5)1.3131 (5)0.5000000.117 (3)0.5
H4A0.2893501.3503000.4681210.176*0.25
H4B0.2532011.2808490.5156500.176*0.25
N10.35870 (12)0.84195 (12)0.44148 (6)0.0254 (3)
N20.49194 (11)0.71006 (11)0.57406 (5)0.0208 (3)
C10.40419 (16)0.94079 (16)0.40753 (8)0.0336 (4)
H1A0.3445351.0001630.4045300.040*
H1B0.4244110.9167640.3656340.040*
C20.50831 (17)0.99034 (16)0.43835 (8)0.0342 (4)
H2A0.4872521.0194450.4791950.041*
H2B0.5377231.0549760.4139850.041*
C30.60086 (15)0.89975 (16)0.44473 (8)0.0305 (4)
H3A0.6303560.8797020.4038180.037*
H3B0.6648460.9309470.4689480.037*
C40.55521 (13)0.79272 (14)0.47577 (7)0.0234 (3)
H40.6140070.7317030.4709970.028*
C50.44555 (14)0.75018 (14)0.44537 (6)0.0238 (3)
H50.4646080.7253120.4029690.029*
C60.25572 (16)0.80021 (18)0.40986 (8)0.0355 (4)
H6A0.2761420.7771100.3678440.043*
H6B0.1993620.8627660.4070920.043*
C70.20234 (16)0.69976 (17)0.44275 (9)0.0358 (4)
H7A0.1352450.6723750.4196510.043*
H7B0.1763920.7237710.4837400.043*
C80.28963 (16)0.60356 (16)0.44880 (9)0.0337 (4)
H8A0.3087760.5737020.4078390.040*
H8B0.2564550.5405190.4729750.040*
C90.39828 (13)0.64686 (14)0.48012 (7)0.0244 (3)
H90.4563340.5848300.4766260.029*
C100.38189 (13)0.67060 (13)0.54886 (7)0.0222 (3)
H100.3254630.7339220.5532220.027*
C110.53762 (13)0.81170 (13)0.54397 (7)0.0227 (3)
H11A0.6113110.8323460.5629500.027*
H11B0.4843560.8761020.5500800.027*
C120.54387 (13)0.66987 (13)0.62436 (7)0.0223 (3)
C130.48330 (15)0.58008 (15)0.66176 (8)0.0294 (4)
H13A0.4979520.5943920.7055540.035*
H13B0.5151190.5043080.6515760.035*
C140.35597 (15)0.57851 (15)0.65091 (8)0.0314 (4)
H14A0.3212110.6498500.6662140.038*
H14B0.3209370.5135580.6727820.038*
C150.33563 (15)0.56709 (15)0.58279 (8)0.0307 (4)
H15A0.2529040.5596860.5748980.037*
H15B0.3736190.4973510.5675670.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0276 (6)0.0382 (7)0.0273 (5)0.0056 (5)0.0083 (5)0.0061 (5)
O20.0506 (9)0.0319 (7)0.0412 (7)0.0041 (6)0.0191 (6)0.0013 (6)
O30.065 (3)0.125 (4)0.107 (3)0.045 (3)0.030 (2)0.076 (3)
O40.139 (5)0.139 (5)0.073 (4)0.069 (6)0.030 (4)0.030 (4)
N10.0248 (7)0.0290 (7)0.0223 (6)0.0074 (5)0.0017 (5)0.0026 (5)
N20.0197 (6)0.0219 (6)0.0210 (5)0.0021 (4)0.0012 (5)0.0022 (5)
C10.0375 (9)0.0371 (10)0.0262 (8)0.0103 (7)0.0024 (7)0.0100 (7)
C20.0415 (10)0.0296 (9)0.0316 (8)0.0019 (8)0.0068 (7)0.0094 (7)
C30.0286 (8)0.0355 (9)0.0272 (8)0.0009 (7)0.0060 (6)0.0070 (7)
C40.0205 (7)0.0272 (8)0.0223 (7)0.0039 (6)0.0018 (6)0.0024 (6)
C50.0243 (8)0.0277 (8)0.0194 (6)0.0073 (6)0.0001 (6)0.0026 (6)
C60.0304 (9)0.0446 (10)0.0313 (8)0.0097 (8)0.0107 (7)0.0027 (8)
C70.0248 (8)0.0411 (10)0.0415 (9)0.0034 (8)0.0130 (7)0.0070 (8)
C80.0310 (9)0.0329 (9)0.0371 (9)0.0015 (7)0.0112 (7)0.0086 (7)
C90.0222 (7)0.0234 (7)0.0276 (7)0.0035 (6)0.0044 (6)0.0045 (6)
C100.0177 (7)0.0219 (7)0.0271 (7)0.0004 (5)0.0025 (6)0.0002 (6)
C110.0233 (7)0.0236 (7)0.0212 (7)0.0041 (6)0.0012 (5)0.0025 (6)
C120.0226 (7)0.0247 (7)0.0195 (6)0.0016 (6)0.0007 (6)0.0004 (6)
C130.0300 (8)0.0317 (8)0.0265 (7)0.0000 (7)0.0022 (6)0.0083 (7)
C140.0271 (8)0.0311 (9)0.0360 (9)0.0039 (7)0.0078 (7)0.0076 (7)
C150.0261 (8)0.0280 (8)0.0382 (9)0.0071 (6)0.0002 (7)0.0042 (7)
Geometric parameters (Å, º) top
O1—C121.242 (2)C5—H51.0000
O2—H2C0.90 (3)C5—C91.536 (2)
O2—H2D0.8882C6—H6A0.9900
O3—H3C0.892 (4)C6—H6B0.9900
O3—H3D0.868 (4)C6—C71.517 (3)
O4—H4A0.8701 (10)C7—H7A0.9900
O4—H4Ai0.8700 (10)C7—H7B0.9900
O4—H4B0.869 (7)C7—C81.530 (3)
O4—H4Bi0.869 (7)C8—H8A0.9900
N1—C11.478 (2)C8—H8B0.9900
N1—C51.485 (2)C8—C91.535 (2)
N1—C61.477 (2)C9—H91.0000
N2—C101.4793 (19)C9—C101.545 (2)
N2—C111.4648 (19)C10—H101.0000
N2—C121.3456 (19)C10—C151.525 (2)
C1—H1A0.9900C11—H11A0.9900
C1—H1B0.9900C11—H11B0.9900
C1—C21.513 (3)C12—C131.513 (2)
C2—H2A0.9900C13—H13A0.9900
C2—H2B0.9900C13—H13B0.9900
C2—C31.526 (3)C13—C141.513 (2)
C3—H3A0.9900C14—H14A0.9900
C3—H3B0.9900C14—H14B0.9900
C3—C41.526 (2)C14—C151.519 (3)
C4—H41.0000C15—H15A0.9900
C4—C51.533 (2)C15—H15B0.9900
C4—C111.526 (2)
H2C—O2—H2D100.8C6—C7—H7B109.7
H3C—O3—H3D115.1 (5)C6—C7—C8109.76 (16)
H4A—O4—H4Ai165.2 (10)H7A—C7—H7B108.2
H4Ai—O4—H4Bi106.1 (5)C8—C7—H7A109.7
H4A—O4—H4Bi87.1 (4)C8—C7—H7B109.7
H4A—O4—H4B106.1 (5)C7—C8—H8A109.5
H4B—O4—H4Ai87.1 (4)C7—C8—H8B109.5
H4B—O4—H4Bi56.7 (5)C7—C8—C9110.53 (14)
C1—N1—C5110.50 (13)H8A—C8—H8B108.1
C6—N1—C1108.64 (13)C9—C8—H8A109.5
C6—N1—C5110.37 (14)C9—C8—H8B109.5
C11—N2—C10113.97 (11)C5—C9—H9106.9
C12—N2—C10126.29 (13)C5—C9—C10112.74 (13)
C12—N2—C11119.28 (13)C8—C9—C5109.85 (14)
N1—C1—H1A109.3C8—C9—H9106.9
N1—C1—H1B109.3C8—C9—C10113.13 (14)
N1—C1—C2111.63 (14)C10—C9—H9106.9
H1A—C1—H1B108.0N2—C10—C9108.19 (12)
C2—C1—H1A109.3N2—C10—H10108.0
C2—C1—H1B109.3N2—C10—C15112.22 (13)
C1—C2—H2A109.6C9—C10—H10108.0
C1—C2—H2B109.6C15—C10—C9112.14 (13)
C1—C2—C3110.37 (15)C15—C10—H10108.0
H2A—C2—H2B108.1N2—C11—C4111.85 (13)
C3—C2—H2A109.6N2—C11—H11A109.2
C3—C2—H2B109.6N2—C11—H11B109.2
C2—C3—H3A109.4C4—C11—H11A109.2
C2—C3—H3B109.4C4—C11—H11B109.2
H3A—C3—H3B108.0H11A—C11—H11B107.9
C4—C3—C2111.38 (14)O1—C12—N2121.90 (14)
C4—C3—H3A109.4O1—C12—C13119.69 (14)
C4—C3—H3B109.4N2—C12—C13118.41 (14)
C3—C4—H4107.5C12—C13—H13A109.0
C3—C4—C5111.64 (13)C12—C13—H13B109.0
C3—C4—C11111.38 (13)C12—C13—C14112.78 (14)
C5—C4—H4107.5H13A—C13—H13B107.8
C11—C4—H4107.5C14—C13—H13A109.0
C11—C4—C5111.10 (12)C14—C13—H13B109.0
N1—C5—C4111.41 (13)C13—C14—H14A110.1
N1—C5—H5108.2C13—C14—H14B110.1
N1—C5—C9110.69 (13)C13—C14—C15108.12 (14)
C4—C5—H5108.2H14A—C14—H14B108.4
C4—C5—C9110.16 (12)C15—C14—H14A110.1
C9—C5—H5108.2C15—C14—H14B110.1
N1—C6—H6A109.2C10—C15—H15A109.5
N1—C6—H6B109.2C10—C15—H15B109.5
N1—C6—C7111.87 (14)C14—C15—C10110.72 (14)
H6A—C6—H6B107.9C14—C15—H15A109.5
C7—C6—H6A109.2C14—C15—H15B109.5
C7—C6—H6B109.2H15A—C15—H15B108.1
C6—C7—H7A109.7
O1—C12—C13—C14157.96 (15)C6—N1—C1—C2178.41 (14)
N1—C1—C2—C357.83 (18)C6—N1—C5—C4177.75 (12)
N1—C5—C9—C857.27 (16)C6—N1—C5—C959.31 (16)
N1—C5—C9—C1069.89 (16)C6—C7—C8—C955.0 (2)
N1—C6—C7—C857.47 (19)C7—C8—C9—C555.19 (19)
N2—C10—C15—C1439.71 (19)C7—C8—C9—C1071.76 (19)
N2—C12—C13—C1421.2 (2)C8—C9—C10—N2179.23 (13)
C1—N1—C5—C457.57 (16)C8—C9—C10—C1554.94 (18)
C1—N1—C5—C9179.49 (12)C9—C10—C15—C14161.74 (14)
C1—N1—C6—C7178.87 (15)C10—N2—C11—C458.37 (16)
C1—C2—C3—C452.81 (19)C10—N2—C12—O1177.29 (14)
C2—C3—C4—C550.99 (18)C10—N2—C12—C133.6 (2)
C2—C3—C4—C1173.86 (18)C11—N2—C10—C957.60 (16)
C3—C4—C5—N153.37 (17)C11—N2—C10—C15178.16 (13)
C3—C4—C5—C9176.61 (13)C11—N2—C12—O111.0 (2)
C3—C4—C11—N2179.02 (13)C11—N2—C12—C13168.13 (14)
C4—C5—C9—C8179.07 (13)C11—C4—C5—N171.63 (16)
C4—C5—C9—C1053.77 (16)C11—C4—C5—C951.61 (16)
C5—N1—C1—C260.38 (18)C12—N2—C10—C9130.31 (15)
C5—N1—C6—C759.84 (18)C12—N2—C10—C156.1 (2)
C5—C4—C11—N253.87 (16)C12—N2—C11—C4128.94 (14)
C5—C9—C10—N255.36 (16)C12—C13—C14—C1553.73 (19)
C5—C9—C10—C15179.65 (13)C13—C14—C15—C1063.65 (18)
Symmetry code: (i) y1, x+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2C···O1ii0.90 (3)1.93 (3)2.8282 (19)175 (3)
O2—H2D···N10.891.932.8125 (19)173
O3—H3C···O2i0.892 (4)1.9909 (14)2.858 (4)163.8 (4)
O3—H3D···O20.868 (4)1.8826 (15)2.710 (4)158.8 (3)
O4—H4B···O3i0.869 (7)1.815 (6)2.648 (9)160.2 (3)
Symmetry codes: (i) y1, x+1, z+1; (ii) x1/2, y+3/2, z+5/4.
Selected torsion angles (°) of matrine between the C and D rings top
Torsion angleMatrin–CAMatrin–SAMatrin–H232234521772012177196
O1—C12—N2—C11-7.9 (3)-7.2 (2)-11.0 (2)-12.6 (5)8.1 (3)18.7 (4)
C14—C15—C10—C9165.56 (16)160.17 (12)161.73 (13)172.2 (3)68.2 (2)76.3 (3)
 

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