Crystallographic studies of cinnamamide derivatives as a means of searching for anti­convulsant activity

A cinnamamide (3-phenyl­prop-2-enamide) core is present in many pharmacologically active compounds. We report three new crystal structures of N-sub­stituted cinnamamide derivatives which were screened for anti­convulsant activity, namely (R,S)-(2E)-N-(2-hy­droxy­prop­yl)-3-phenyl­prop-2-enamide, C₁₂H₁₅NO₂, (1), (R,S)-(2E)-N-(1-hy­droxy­butan-2-yl)-3-phenyl­prop-2-enamide, C₁₃H₁₇NO₂, (2), and (2E)-1-(4-hy­droxy­piperidin-1-yl)-3-phenyl­prop-2-en-1-one, C₁₄H₁₇NO₂, (3). Compounds (1) and (2) crystallize in the Pbca space group with one mol­ecule in the asymmetric unit, whereas compound (3) crystallizes in the P2₁/c space group with two mol­ecules in the asymmetric unit. All the crystal structures are stabilized by inter­molecular O—H...O hydrogen bonds and additionally by N—H...O hydrogen bonds in the structures of (1) and (2). The investigated compounds possess fragments that are considered as beneficial for anti­convulsant activity. The conformations of these compounds were analyzed in comparison with the characteristic features of the proposed pharmacophore model of anti­convulsants active in the maximal electroshock test, i.e. a phenyl ring or other hydro­phobic unit, an electron-donor atom and a hydrogen-bond acceptor/donor domain. In the reported series, two calculated distances fitted the reference model, while the third did not. Structure–activity analysis suggests that anti­convulsant properties may be related to the N-atom substituent. It is beneficial to combine an electron-donor atom (e.g. an O atom) with an H atom in the substituent to ensure appropriate inter­actions with the mol­ecular target. We analyzed the inter­molecular inter­actions in order to find an appropriate spatial arrangement of the important features responsible for anti­convulsant activity.

Computing details

For all structures, data collection: COLLECT (Bruker, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(R,S)-(2E)-N-(2-Hydroxypropyl)-3-phenylprop-2-enamide (1)

Crystal data

C12H15NO2	F(000) = 880
Mr = 205.25	Dx = 1.276 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6025 reflections
a = 9.2070 (2) Å	θ = 1.0–27.5°
b = 8.2100 (2) Å	µ = 0.09 mm^−1
c = 28.2700 (7) Å	T = 100 K
V = 2136.91 (9) Å^3	Block, colourless
Z = 8	0.42 × 0.25 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer	2410 independent reflections
Horizonally mounted graphite crystal monochromator	2015 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.042
CCD scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.964, Tmax = 0.999	k = −9→10
11825 measured reflections	l = −33→36

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0404P)^2 + 1.0007P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2410 reflections	Δρmax = 0.30 e Å^−3
145 parameters	Δρmin = −0.19 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.77904 (9)	0.12905 (11)	0.49081 (3)	0.0209 (2)
C3	0.69803 (13)	0.09672 (15)	0.58725 (4)	0.0175 (3)
H3	0.7867	0.0516	0.5761	0.021*
C4	0.66250 (13)	0.06725 (15)	0.63714 (4)	0.0173 (3)
C9	0.53564 (13)	0.12588 (15)	0.65889 (4)	0.0192 (3)
H9	0.471	0.1935	0.6416	0.023*
C1	0.65893 (13)	0.18039 (14)	0.50514 (4)	0.0174 (3)
C10	0.56487 (13)	0.21472 (15)	0.42450 (4)	0.0181 (3)
H10A	0.4654	0.2137	0.4112	0.022*
H10B	0.6101	0.1083	0.4172	0.022*
C12	0.64733 (15)	0.32180 (17)	0.34692 (5)	0.0240 (3)
H12A	0.5463	0.3244	0.336	0.036*
H12B	0.6903	0.2158	0.3393	0.036*
H12C	0.7025	0.4082	0.3311	0.036*
C7	0.59699 (14)	−0.01487 (16)	0.73093 (5)	0.0226 (3)
H7	0.5738	−0.044	0.7626	0.027*
C2	0.61930 (13)	0.17998 (15)	0.55588 (4)	0.0186 (3)
H2	0.5368	0.2397	0.5662	0.022*
C11	0.65171 (13)	0.34823 (15)	0.39992 (4)	0.0184 (3)
H11	0.7548	0.344	0.411	0.022*
C6	0.72354 (15)	−0.07254 (17)	0.71012 (5)	0.0234 (3)
H6	0.7876	−0.1405	0.7276	0.028*
C5	0.75615 (14)	−0.03053 (16)	0.66370 (4)	0.0203 (3)
H5	0.8436	−0.069	0.6498	0.024*
C8	0.50409 (14)	0.08590 (16)	0.70529 (5)	0.0214 (3)
H8	0.4186	0.1274	0.7198	0.026*
N1	0.55491 (12)	0.23163 (13)	0.47557 (4)	0.0186 (2)
O2	0.59293 (10)	0.50511 (11)	0.40982 (3)	0.0224 (2)
H1	0.4757 (19)	0.272 (2)	0.4873 (6)	0.032 (4)*
H2O	0.637 (2)	0.541 (2)	0.4386 (7)	0.059 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0154 (4)	0.0259 (5)	0.0213 (5)	0.0024 (4)	0.0016 (3)	−0.0028 (4)
C3	0.0149 (6)	0.0166 (6)	0.0210 (6)	−0.0022 (5)	0.0015 (5)	−0.0030 (5)
C4	0.0180 (6)	0.0143 (6)	0.0198 (6)	−0.0036 (5)	−0.0015 (5)	−0.0019 (4)
C9	0.0168 (6)	0.0188 (6)	0.0221 (7)	−0.0009 (5)	−0.0025 (5)	−0.0012 (5)
C1	0.0156 (6)	0.0142 (6)	0.0223 (7)	−0.0023 (5)	0.0002 (5)	−0.0012 (5)
C10	0.0165 (6)	0.0192 (6)	0.0186 (6)	−0.0006 (5)	−0.0021 (5)	−0.0012 (5)
C12	0.0262 (7)	0.0269 (7)	0.0190 (7)	−0.0017 (6)	−0.0004 (5)	−0.0002 (5)
C7	0.0267 (7)	0.0223 (7)	0.0187 (6)	−0.0056 (5)	−0.0008 (5)	−0.0006 (5)
C2	0.0157 (6)	0.0184 (6)	0.0217 (7)	0.0005 (5)	0.0024 (5)	−0.0019 (5)
C11	0.0171 (6)	0.0179 (6)	0.0203 (7)	−0.0002 (5)	−0.0013 (5)	−0.0005 (5)
C6	0.0254 (7)	0.0207 (7)	0.0241 (7)	0.0005 (5)	−0.0056 (5)	0.0010 (5)
C5	0.0193 (6)	0.0172 (6)	0.0243 (7)	0.0001 (5)	−0.0015 (5)	−0.0016 (5)
C8	0.0198 (6)	0.0225 (7)	0.0219 (7)	−0.0024 (5)	0.0015 (5)	−0.0036 (5)
N1	0.0146 (5)	0.0217 (5)	0.0196 (6)	0.0008 (4)	0.0021 (4)	0.0000 (4)
O2	0.0242 (5)	0.0180 (5)	0.0250 (5)	0.0018 (4)	−0.0047 (4)	−0.0012 (4)

Geometric parameters (Å, º)

O1—C1	1.2509 (15)	C12—H12A	0.98
C3—C2	1.3338 (18)	C12—H12B	0.98
C3—C4	1.4681 (17)	C12—H12C	0.98
C3—H3	0.95	C7—C6	1.3884 (19)
C4—C5	1.3969 (17)	C7—C8	1.3934 (19)
C4—C9	1.4049 (17)	C7—H7	0.95
C9—C8	1.3831 (18)	C2—H2	0.95
C9—H9	0.95	C11—O2	1.4249 (15)
C1—N1	1.3390 (16)	C11—H11	1
C1—C2	1.4800 (17)	C6—C5	1.3899 (18)
C10—N1	1.4533 (16)	C6—H6	0.95
C10—C11	1.5243 (17)	C5—H5	0.95
C10—H10A	0.99	C8—H8	0.95
C10—H10B	0.99	N1—H1	0.867 (18)
C12—C11	1.5146 (17)	O2—H2O	0.96 (2)
C2—C3—C4	127.02 (12)	C6—C7—H7	120.1
C2—C3—H3	116.5	C8—C7—H7	120.1
C4—C3—H3	116.5	C3—C2—C1	120.77 (11)
C5—C4—C9	118.35 (12)	C3—C2—H2	119.6
C5—C4—C3	118.26 (11)	C1—C2—H2	119.6
C9—C4—C3	123.31 (11)	O2—C11—C12	108.29 (10)
C8—C9—C4	120.55 (12)	O2—C11—C10	111.18 (10)
C8—C9—H9	119.7	C12—C11—C10	109.52 (10)
C4—C9—H9	119.7	O2—C11—H11	109.3
O1—C1—N1	122.41 (12)	C12—C11—H11	109.3
O1—C1—C2	122.08 (11)	C10—C11—H11	109.3
N1—C1—C2	115.43 (11)	C7—C6—C5	119.78 (13)
N1—C10—C11	114.67 (10)	C7—C6—H6	120.1
N1—C10—H10A	108.6	C5—C6—H6	120.1
C11—C10—H10A	108.6	C6—C5—C4	121.11 (12)
N1—C10—H10B	108.6	C6—C5—H5	119.4
C11—C10—H10B	108.6	C4—C5—H5	119.4
H10A—C10—H10B	107.6	C9—C8—C7	120.36 (12)
C11—C12—H12A	109.5	C9—C8—H8	119.8
C11—C12—H12B	109.5	C7—C8—H8	119.8
H12A—C12—H12B	109.5	C1—N1—C10	123.03 (11)
C11—C12—H12C	109.5	C1—N1—H1	118.9 (11)
H12A—C12—H12C	109.5	C10—N1—H1	117.9 (11)
H12B—C12—H12C	109.5	C11—O2—H2O	106.7 (12)
C6—C7—C8	119.81 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1^i	0.96 (2)	1.81 (2)	2.769 (1)	175 (2)
N1—H1···O1^ii	0.86 (2)	2.08 (2)	2.943 (1)	175 (2)
C2—H2···O2^iii	0.95	2.51	3.383 (2)	154

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x−1/2, −y+1/2, −z+1; (iii) −x+1, −y+1, −z+1.

(R,S)-(2E)-N-(1-Hydroxybutan-2-yl)-3-phenylprop-2-enamide (2)

Crystal data

C13H17NO2	F(000) = 944
Mr = 219.27	Dx = 1.204 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2905 reflections
a = 10.6270 (4) Å	θ = 1.0–27.5°
b = 9.2490 (4) Å	µ = 0.08 mm^−1
c = 24.6230 (9) Å	T = 100 K
V = 2420.2 (2) Å^3	Needle, colourless
Z = 8	1.0 × 0.43 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	2719 independent reflections
Horizonally mounted graphite crystal monochromator	2042 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.045
CCD scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −13→13
Tmin = 0.909, Tmax = 0.994	k = −11→11
4834 measured reflections	l = −31→31

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0694P)^2 + 0.7184P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.137	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.30 e Å^−3
2719 reflections	Δρmin = −0.21 e Å^−3
155 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0070 (14)

Special details

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

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

	x	y	z	Uiso*/Ueq
C9	0.71892 (16)	0.1719 (2)	0.72466 (7)	0.0278 (4)
H9	0.7797	0.2169	0.702	0.033*
C8	0.70602 (17)	0.2169 (2)	0.77805 (7)	0.0335 (4)
H8	0.7582	0.2921	0.7916	0.04*
C7	0.61743 (17)	0.1529 (2)	0.81182 (6)	0.0309 (4)
H7	0.6089	0.1838	0.8484	0.037*
C6	0.54178 (16)	0.0439 (2)	0.79170 (7)	0.0304 (4)
H6	0.4803	0.0005	0.8145	0.036*
C5	0.55521 (16)	−0.0028 (2)	0.73816 (6)	0.0261 (4)
H5	0.5036	−0.0789	0.7249	0.031*
C4	0.64381 (14)	0.06129 (19)	0.70382 (6)	0.0210 (4)
C3	0.65472 (14)	0.00831 (19)	0.64778 (6)	0.0203 (4)
H3	0.6164	−0.0823	0.6402	0.024*
C2	0.71274 (13)	0.07371 (18)	0.60623 (6)	0.0192 (4)
H2	0.7533	0.164	0.6118	0.023*
C1	0.71402 (13)	0.00579 (18)	0.55145 (6)	0.0180 (3)
O1	0.67756 (10)	−0.12149 (12)	0.54388 (4)	0.0219 (3)
N1	0.75602 (12)	0.08984 (16)	0.51125 (5)	0.0190 (3)
C10	0.75661 (15)	0.04109 (19)	0.45428 (6)	0.0212 (4)
H10	0.7893	−0.0602	0.4531	0.025*
C12	0.84381 (15)	0.13639 (19)	0.42087 (6)	0.0235 (4)
H12A	0.8185	0.2386	0.4257	0.028*
H12B	0.8334	0.1119	0.382	0.028*
C13	0.98199 (15)	0.1209 (2)	0.43600 (7)	0.0305 (4)
H13A	0.9949	0.1557	0.4732	0.046*
H13B	1.0334	0.1782	0.4109	0.046*
H13C	1.0066	0.019	0.4336	0.046*
C11	0.62235 (14)	0.04163 (19)	0.43154 (6)	0.0220 (4)
H11A	0.6231	0.0062	0.3936	0.026*
H11B	0.5687	−0.0241	0.4533	0.026*
O2	0.57207 (11)	0.18365 (13)	0.43316 (4)	0.0257 (3)
H1	0.7750 (16)	0.178 (2)	0.5181 (7)	0.017 (4)*
H2O	0.488 (2)	0.180 (2)	0.4399 (9)	0.053 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C9	0.0288 (9)	0.0323 (11)	0.0223 (8)	−0.0047 (8)	0.0017 (6)	−0.0020 (7)
C8	0.0400 (10)	0.0357 (11)	0.0250 (9)	−0.0033 (9)	−0.0011 (7)	−0.0090 (8)
C7	0.0392 (9)	0.0353 (11)	0.0182 (8)	0.0101 (8)	0.0001 (7)	−0.0033 (7)
C6	0.0317 (9)	0.0378 (11)	0.0215 (8)	0.0056 (8)	0.0062 (7)	0.0044 (7)
C5	0.0276 (8)	0.0292 (10)	0.0215 (8)	−0.0013 (7)	0.0005 (6)	0.0027 (7)
C4	0.0219 (8)	0.0235 (9)	0.0176 (7)	0.0044 (7)	−0.0014 (6)	−0.0001 (6)
C3	0.0199 (7)	0.0213 (9)	0.0198 (7)	0.0021 (6)	−0.0011 (6)	0.0002 (6)
C2	0.0185 (7)	0.0204 (9)	0.0187 (7)	0.0023 (6)	−0.0023 (5)	−0.0023 (6)
C1	0.0159 (7)	0.0193 (9)	0.0188 (7)	0.0022 (6)	−0.0001 (5)	−0.0008 (6)
O1	0.0236 (6)	0.0187 (6)	0.0236 (6)	−0.0001 (5)	0.0032 (4)	−0.0025 (5)
N1	0.0225 (6)	0.0185 (8)	0.0160 (6)	−0.0029 (6)	0.0001 (5)	−0.0034 (5)
C10	0.0232 (7)	0.0226 (9)	0.0179 (7)	−0.0014 (7)	0.0013 (6)	−0.0034 (6)
C12	0.0252 (8)	0.0235 (9)	0.0216 (7)	−0.0011 (7)	0.0030 (6)	−0.0015 (6)
C13	0.0203 (8)	0.0421 (12)	0.0292 (9)	−0.0020 (8)	0.0028 (6)	0.0006 (8)
C11	0.0221 (7)	0.0250 (10)	0.0190 (7)	−0.0013 (7)	−0.0007 (6)	−0.0029 (6)
O2	0.0233 (6)	0.0266 (7)	0.0273 (6)	0.0008 (5)	0.0002 (5)	0.0026 (5)

Geometric parameters (Å, º)

C9—C8	1.386 (2)	C1—N1	1.335 (2)
C9—C4	1.395 (2)	N1—C10	1.4733 (18)
C9—H9	0.95	N1—H1	0.856 (18)
C8—C7	1.389 (3)	C10—C12	1.521 (2)
C8—H8	0.95	C10—C11	1.533 (2)
C7—C6	1.382 (3)	C10—H10	1
C7—H7	0.95	C12—C13	1.522 (2)
C6—C5	1.395 (2)	C12—H12A	0.99
C6—H6	0.95	C12—H12B	0.99
C5—C4	1.397 (2)	C13—H13A	0.98
C5—H5	0.95	C13—H13B	0.98
C4—C3	1.469 (2)	C13—H13C	0.98
C3—C2	1.339 (2)	C11—O2	1.419 (2)
C3—H3	0.95	C11—H11A	0.99
C2—C1	1.488 (2)	C11—H11B	0.99
C2—H2	0.95	O2—H2O	0.91 (3)
C1—O1	1.253 (2)
C8—C9—C4	120.83 (16)	C1—N1—H1	119.1 (12)
C8—C9—H9	119.6	C10—N1—H1	118.6 (12)
C4—C9—H9	119.6	N1—C10—C12	109.89 (13)
C9—C8—C7	120.46 (17)	N1—C10—C11	110.05 (13)
C9—C8—H8	119.8	C12—C10—C11	111.57 (13)
C7—C8—H8	119.8	N1—C10—H10	108.4
C6—C7—C8	119.41 (15)	C12—C10—H10	108.4
C6—C7—H7	120.3	C11—C10—H10	108.4
C8—C7—H7	120.3	C10—C12—C13	113.65 (14)
C7—C6—C5	120.37 (16)	C10—C12—H12A	108.8
C7—C6—H6	119.8	C13—C12—H12A	108.8
C5—C6—H6	119.8	C10—C12—H12B	108.8
C6—C5—C4	120.62 (16)	C13—C12—H12B	108.8
C6—C5—H5	119.7	H12A—C12—H12B	107.7
C4—C5—H5	119.7	C12—C13—H13A	109.5
C9—C4—C5	118.30 (14)	C12—C13—H13B	109.5
C9—C4—C3	123.01 (14)	H13A—C13—H13B	109.5
C5—C4—C3	118.68 (15)	C12—C13—H13C	109.5
C2—C3—C4	127.11 (16)	H13A—C13—H13C	109.5
C2—C3—H3	116.4	H13B—C13—H13C	109.5
C4—C3—H3	116.4	O2—C11—C10	110.08 (13)
C3—C2—C1	120.40 (15)	O2—C11—H11A	109.6
C3—C2—H2	119.8	C10—C11—H11A	109.6
C1—C2—H2	119.8	O2—C11—H11B	109.6
O1—C1—N1	122.67 (14)	C10—C11—H11B	109.6
O1—C1—C2	121.91 (14)	H11A—C11—H11B	108.2
N1—C1—C2	115.42 (14)	C11—O2—H2O	110.0 (15)
C1—N1—C10	121.93 (14)
C4—C9—C8—C7	−0.3 (3)	C3—C2—C1—O1	−10.2 (2)
C9—C8—C7—C6	−0.1 (3)	C3—C2—C1—N1	169.54 (14)
C8—C7—C6—C5	0.8 (3)	O1—C1—N1—C10	3.1 (2)
C7—C6—C5—C4	−1.0 (3)	C2—C1—N1—C10	−176.62 (13)
C8—C9—C4—C5	0.0 (3)	C1—N1—C10—C12	−162.75 (14)
C8—C9—C4—C3	−179.23 (16)	C1—N1—C10—C11	74.00 (19)
C6—C5—C4—C9	0.6 (2)	N1—C10—C12—C13	66.99 (19)
C6—C5—C4—C3	179.90 (15)	C11—C10—C12—C13	−170.66 (14)
C9—C4—C3—C2	−16.1 (3)	N1—C10—C11—O2	60.87 (16)
C5—C4—C3—C2	164.65 (16)	C12—C10—C11—O2	−61.40 (16)
C4—C3—C2—C1	−179.32 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1^i	0.91 (3)	1.88 (3)	2.773 (2)	165 (2)
N1—H1···O1^ii	0.86 (2)	2.03 (2)	2.876 (2)	173 (2)
C2—H2···O1^ii	0.95	2.70	3.415 (2)	133
C7—H7···O2^iii	0.95	2.45	3.383 (2)	167

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, z; (iii) x, −y+1/2, z+1/2.

(2E)-1-(4-hydroxypiperidin-1-yl)-3-phenylprop-2-en-1-one (3)

Crystal data

C14H17NO2	F(000) = 992
Mr = 231.28	Dx = 1.241 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7280 reflections
a = 14.2940 (7) Å	θ = 1.0–27.5°
b = 11.4480 (6) Å	µ = 0.08 mm^−1
c = 16.1120 (9) Å	T = 100 K
β = 110.158 (3)°	Block, colourless
V = 2475.0 (2) Å^3	0.46 × 0.25 × 0.15 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	3877 reflections with I > 2σ(I)
CCD scans	Rint = 0.047
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	θmax = 27.5°, θmin = 3.0°
Tmin = 0.963, Tmax = 0.988	h = −18→18
15206 measured reflections	k = −14→14
5525 independent reflections	l = −19→20

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.9018P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.25 e Å^−3
5525 reflections	Δρmin = −0.22 e Å^−3
316 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0061 (10)

Special details

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

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

	x	y	z	Uiso*/Ueq
O2A	0.78159 (10)	0.47906 (11)	0.64789 (9)	0.0346 (3)
C12A	0.77634 (12)	0.35948 (15)	0.66984 (11)	0.0267 (4)
H12A	0.7674	0.3573	0.7287	0.032*
C11	0.87211 (12)	0.29399 (15)	0.67953 (11)	0.0281 (4)
H11A	0.8857	0.2982	0.6234	0.034*
H11C	0.9285	0.331	0.7263	0.034*
C10A	0.86327 (12)	0.16753 (16)	0.70311 (11)	0.0295 (4)
H10A	0.9248	0.125	0.7065	0.035*
H10C	0.8555	0.1631	0.7617	0.035*
N1A	0.77721 (10)	0.11278 (12)	0.63643 (9)	0.0263 (3)
C14A	0.68213 (12)	0.17000 (15)	0.62661 (12)	0.0284 (4)
H14A	0.668	0.1628	0.6824	0.034*
H14C	0.6276	0.1311	0.5791	0.034*
C13	0.68658 (12)	0.29807 (15)	0.60410 (11)	0.0269 (4)
H13A	0.6248	0.3374	0.6039	0.032*
H13C	0.6901	0.3048	0.544	0.032*
C1A	0.77952 (12)	0.01756 (15)	0.58768 (11)	0.0261 (4)
O1A	0.70253 (9)	−0.02909 (11)	0.53809 (9)	0.0363 (3)
C2A	0.87930 (12)	−0.02847 (15)	0.59372 (11)	0.0256 (4)
H2A	0.9352	0.0225	0.6099	0.031*
C3A	0.89076 (12)	−0.13971 (15)	0.57677 (11)	0.0255 (4)
H3A	0.8343	−0.189	0.5658	0.031*
C4A	0.98257 (12)	−0.19449 (15)	0.57329 (11)	0.0242 (4)
C9A	1.06720 (12)	−0.12831 (16)	0.57927 (11)	0.0271 (4)
H9A	1.0667	−0.0461	0.5873	0.032*
C8A	1.15151 (12)	−0.18219 (16)	0.57359 (11)	0.0286 (4)
H8A	1.2086	−0.1367	0.5779	0.034*
C7A	1.15337 (12)	−0.30183 (16)	0.56174 (11)	0.0289 (4)
H7A	1.2114	−0.3384	0.5578	0.035*
C6A	1.07010 (12)	−0.36791 (16)	0.55560 (11)	0.0299 (4)
H6A	1.071	−0.45	0.5474	0.036*
C5A	0.98508 (12)	−0.31437 (16)	0.56139 (11)	0.0279 (4)
H5A	0.9283	−0.3603	0.5572	0.033*
O2B	0.89628 (9)	−0.13973 (13)	0.26615 (9)	0.0370 (3)
C12B	0.81214 (12)	−0.20269 (15)	0.27152 (12)	0.0276 (4)
H12B	0.7633	−0.2146	0.2105	0.033*
C11B	0.76169 (13)	−0.13560 (15)	0.32601 (12)	0.0291 (4)
H11D	0.7356	−0.0608	0.2962	0.035*
H11B	0.8113	−0.1175	0.3848	0.035*
C10B	0.67627 (13)	−0.20561 (15)	0.33779 (12)	0.0293 (4)
H10D	0.6483	−0.1626	0.3772	0.035*
H10B	0.6227	−0.2158	0.2798	0.035*
N1B	0.71215 (10)	−0.32033 (12)	0.37605 (9)	0.0249 (3)
C14B	0.75993 (12)	−0.38805 (15)	0.32405 (12)	0.0268 (4)
H14D	0.7104	−0.4054	0.2651	0.032*
H14B	0.7843	−0.4632	0.3541	0.032*
C13B	0.84699 (12)	−0.32056 (16)	0.31314 (12)	0.0276 (4)
H13D	0.8995	−0.3097	0.3716	0.033*
H13B	0.8758	−0.3656	0.2753	0.033*
C1B	0.69647 (11)	−0.36930 (15)	0.44622 (11)	0.0229 (4)
O1B	0.72572 (9)	−0.46994 (10)	0.47088 (8)	0.0293 (3)
C2B	0.64182 (11)	−0.30024 (15)	0.49318 (11)	0.0246 (4)
H2B	0.6424	−0.2173	0.4912	0.03*
C3B	0.59195 (11)	−0.35520 (16)	0.53811 (11)	0.0260 (4)
H3B	0.5935	−0.4382	0.5377	0.031*
C4B	0.53510 (11)	−0.30052 (17)	0.58809 (11)	0.0279 (4)
C9B	0.53074 (12)	−0.18025 (18)	0.59829 (12)	0.0330 (4)
H9B	0.5666	−0.13	0.5731	0.04*
C8B	0.47418 (14)	−0.1332 (2)	0.64507 (13)	0.0421 (5)
H8B	0.4711	−0.051	0.6516	0.051*
C7B	0.42193 (13)	−0.2074 (2)	0.68244 (13)	0.0449 (6)
H7B	0.3836	−0.1754	0.7148	0.054*
C6B	0.42566 (13)	−0.3257 (2)	0.67275 (12)	0.0412 (5)
H6B	0.3897	−0.3757	0.6981	0.049*
C5B	0.48174 (12)	−0.37260 (19)	0.62607 (12)	0.0345 (4)
H5B	0.4841	−0.4549	0.6197	0.041*
H2AO	0.7662 (16)	0.4878 (18)	0.5916 (16)	0.046 (6)*
H2BO	0.8734 (18)	−0.081 (2)	0.2299 (17)	0.063 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2A	0.0422 (7)	0.0287 (7)	0.0278 (7)	−0.0008 (6)	0.0054 (6)	−0.0020 (6)
C12A	0.0277 (9)	0.0300 (10)	0.0225 (9)	0.0023 (7)	0.0088 (7)	0.0002 (7)
C11	0.0222 (8)	0.0378 (10)	0.0229 (9)	−0.0003 (7)	0.0059 (7)	−0.0049 (7)
C10A	0.0228 (8)	0.0374 (10)	0.0259 (9)	0.0056 (8)	0.0054 (7)	−0.0027 (8)
N1A	0.0203 (7)	0.0302 (8)	0.0288 (8)	0.0030 (6)	0.0091 (6)	−0.0001 (6)
C14A	0.0218 (8)	0.0332 (10)	0.0340 (10)	0.0044 (7)	0.0145 (7)	0.0014 (8)
C13	0.0220 (8)	0.0312 (10)	0.0277 (9)	0.0049 (7)	0.0088 (7)	−0.0002 (7)
C1A	0.0242 (8)	0.0247 (9)	0.0316 (9)	0.0011 (7)	0.0125 (7)	0.0037 (7)
O1A	0.0243 (6)	0.0315 (7)	0.0515 (9)	−0.0008 (5)	0.0112 (6)	−0.0070 (6)
C2A	0.0221 (8)	0.0283 (9)	0.0273 (9)	−0.0006 (7)	0.0099 (7)	0.0008 (7)
C3A	0.0205 (8)	0.0285 (10)	0.0271 (9)	−0.0020 (7)	0.0076 (7)	−0.0009 (7)
C4A	0.0213 (8)	0.0297 (10)	0.0197 (8)	0.0025 (7)	0.0048 (7)	−0.0008 (7)
C9A	0.0263 (8)	0.0280 (9)	0.0275 (9)	0.0030 (7)	0.0101 (7)	0.0016 (7)
C8A	0.0245 (8)	0.0370 (11)	0.0261 (9)	0.0014 (7)	0.0110 (7)	0.0040 (7)
C7A	0.0241 (8)	0.0400 (11)	0.0221 (9)	0.0088 (8)	0.0075 (7)	−0.0021 (7)
C6A	0.0272 (9)	0.0310 (10)	0.0263 (9)	0.0050 (7)	0.0028 (7)	−0.0068 (7)
C5A	0.0207 (8)	0.0316 (10)	0.0269 (9)	−0.0007 (7)	0.0024 (7)	−0.0041 (7)
O2B	0.0229 (6)	0.0445 (9)	0.0442 (8)	−0.0004 (6)	0.0125 (6)	0.0159 (7)
C12B	0.0206 (8)	0.0341 (10)	0.0286 (9)	−0.0009 (7)	0.0094 (7)	0.0056 (7)
C11B	0.0287 (9)	0.0293 (10)	0.0294 (9)	0.0024 (7)	0.0103 (7)	0.0062 (7)
C10B	0.0264 (9)	0.0324 (10)	0.0326 (10)	0.0068 (7)	0.0147 (8)	0.0073 (8)
N1B	0.0224 (7)	0.0271 (8)	0.0272 (8)	0.0028 (6)	0.0113 (6)	0.0027 (6)
C14B	0.0274 (9)	0.0283 (9)	0.0269 (9)	0.0018 (7)	0.0121 (7)	0.0012 (7)
C13B	0.0238 (8)	0.0336 (10)	0.0282 (9)	0.0040 (7)	0.0125 (7)	0.0036 (7)
C1B	0.0191 (7)	0.0257 (9)	0.0236 (8)	−0.0048 (7)	0.0068 (7)	−0.0018 (7)
O1B	0.0360 (7)	0.0233 (7)	0.0324 (7)	0.0007 (5)	0.0169 (6)	0.0010 (5)
C2B	0.0205 (8)	0.0261 (9)	0.0263 (9)	−0.0016 (7)	0.0067 (7)	−0.0008 (7)
C3B	0.0195 (8)	0.0331 (10)	0.0242 (9)	−0.0027 (7)	0.0059 (7)	−0.0018 (7)
C4B	0.0157 (8)	0.0451 (11)	0.0212 (9)	−0.0022 (7)	0.0043 (7)	−0.0009 (7)
C9B	0.0236 (9)	0.0461 (12)	0.0299 (10)	0.0067 (8)	0.0102 (8)	0.0029 (8)
C8B	0.0344 (10)	0.0530 (13)	0.0396 (12)	0.0161 (9)	0.0137 (9)	0.0018 (9)
C7B	0.0220 (9)	0.0803 (17)	0.0355 (11)	0.0086 (10)	0.0139 (8)	−0.0028 (11)
C6B	0.0230 (9)	0.0723 (16)	0.0301 (10)	−0.0124 (10)	0.0114 (8)	−0.0064 (10)
C5B	0.0218 (8)	0.0544 (13)	0.0264 (9)	−0.0093 (8)	0.0072 (7)	−0.0061 (8)

Geometric parameters (Å, º)

O2A—C12A	1.422 (2)	O2B—C12B	1.430 (2)
O2A—H2AO	0.86 (2)	O2B—H2BO	0.88 (3)
C12A—C11	1.521 (2)	C12B—C13B	1.513 (2)
C12A—C13	1.525 (2)	C12B—C11B	1.522 (2)
C12A—H12A	1	C12B—H12B	1
C11—C10A	1.513 (3)	C11B—C10B	1.526 (2)
C11—H11A	0.99	C11B—H11D	0.99
C11—H11C	0.99	C11B—H11B	0.99
C10A—N1A	1.466 (2)	C10B—N1B	1.466 (2)
C10A—H10A	0.99	C10B—H10D	0.99
C10A—H10C	0.99	C10B—H10B	0.99
N1A—C1A	1.351 (2)	N1B—C1B	1.348 (2)
N1A—C14A	1.467 (2)	N1B—C14B	1.471 (2)
C14A—C13	1.517 (2)	C14B—C13B	1.526 (2)
C14A—H14A	0.99	C14B—H14D	0.99
C14A—H14C	0.99	C14B—H14B	0.99
C13—H13A	0.99	C13B—H13D	0.99
C13—H13C	0.99	C13B—H13B	0.99
C1A—O1A	1.236 (2)	C1B—O1B	1.243 (2)
C1A—C2A	1.492 (2)	C1B—C2B	1.488 (2)
C2A—C3A	1.324 (2)	C2B—C3B	1.336 (2)
C2A—H2A	0.95	C2B—H2B	0.95
C3A—C4A	1.473 (2)	C3B—C4B	1.467 (2)
C3A—H3A	0.95	C3B—H3B	0.95
C4A—C5A	1.388 (2)	C4B—C9B	1.390 (3)
C4A—C9A	1.402 (2)	C4B—C5B	1.400 (2)
C9A—C8A	1.385 (2)	C9B—C8B	1.390 (3)
C9A—H9A	0.95	C9B—H9B	0.95
C8A—C7A	1.384 (3)	C8B—C7B	1.397 (3)
C8A—H8A	0.95	C8B—H8B	0.95
C7A—C6A	1.385 (2)	C7B—C6B	1.366 (3)
C7A—H7A	0.95	C7B—H7B	0.95
C6A—C5A	1.392 (2)	C6B—C5B	1.383 (3)
C6A—H6A	0.95	C6B—H6B	0.95
C5A—H5A	0.95	C5B—H5B	0.95
C12A—O2A—H2AO	110.9 (14)	C12B—O2B—H2BO	107.4 (16)
O2A—C12A—C11	112.16 (14)	O2B—C12B—C13B	108.72 (13)
O2A—C12A—C13	112.01 (14)	O2B—C12B—C11B	110.86 (14)
C11—C12A—C13	110.86 (14)	C13B—C12B—C11B	110.09 (14)
O2A—C12A—H12A	107.2	O2B—C12B—H12B	109
C11—C12A—H12A	107.2	C13B—C12B—H12B	109
C13—C12A—H12A	107.2	C11B—C12B—H12B	109
C10A—C11—C12A	110.33 (14)	C12B—C11B—C10B	111.42 (15)
C10A—C11—H11A	109.6	C12B—C11B—H11D	109.3
C12A—C11—H11A	109.6	C10B—C11B—H11D	109.3
C10A—C11—H11C	109.6	C12B—C11B—H11B	109.3
C12A—C11—H11C	109.6	C10B—C11B—H11B	109.3
H11A—C11—H11C	108.1	H11D—C11B—H11B	108
N1A—C10A—C11	110.29 (14)	N1B—C10B—C11B	110.11 (13)
N1A—C10A—H10A	109.6	N1B—C10B—H10D	109.6
C11—C10A—H10A	109.6	C11B—C10B—H10D	109.6
N1A—C10A—H10C	109.6	N1B—C10B—H10B	109.6
C11—C10A—H10C	109.6	C11B—C10B—H10B	109.6
H10A—C10A—H10C	108.1	H10D—C10B—H10B	108.2
C1A—N1A—C10A	126.07 (14)	C1B—N1B—C10B	126.15 (14)
C1A—N1A—C14A	120.33 (14)	C1B—N1B—C14B	120.17 (14)
C10A—N1A—C14A	113.59 (14)	C10B—N1B—C14B	113.35 (13)
N1A—C14A—C13	110.10 (13)	N1B—C14B—C13B	110.85 (14)
N1A—C14A—H14A	109.6	N1B—C14B—H14D	109.5
C13—C14A—H14A	109.6	C13B—C14B—H14D	109.5
N1A—C14A—H14C	109.6	N1B—C14B—H14B	109.5
C13—C14A—H14C	109.6	C13B—C14B—H14B	109.5
H14A—C14A—H14C	108.2	H14D—C14B—H14B	108.1
C14A—C13—C12A	111.96 (14)	C12B—C13B—C14B	110.23 (13)
C14A—C13—H13A	109.2	C12B—C13B—H13D	109.6
C12A—C13—H13A	109.2	C14B—C13B—H13D	109.6
C14A—C13—H13C	109.2	C12B—C13B—H13B	109.6
C12A—C13—H13C	109.2	C14B—C13B—H13B	109.6
H13A—C13—H13C	107.9	H13D—C13B—H13B	108.1
O1A—C1A—N1A	121.98 (15)	O1B—C1B—N1B	121.24 (15)
O1A—C1A—C2A	120.51 (16)	O1B—C1B—C2B	120.50 (15)
N1A—C1A—C2A	117.49 (15)	N1B—C1B—C2B	118.26 (15)
C3A—C2A—C1A	120.63 (15)	C3B—C2B—C1B	119.80 (16)
C3A—C2A—H2A	119.7	C3B—C2B—H2B	120.1
C1A—C2A—H2A	119.7	C1B—C2B—H2B	120.1
C2A—C3A—C4A	126.32 (15)	C2B—C3B—C4B	126.63 (17)
C2A—C3A—H3A	116.8	C2B—C3B—H3B	116.7
C4A—C3A—H3A	116.8	C4B—C3B—H3B	116.7
C5A—C4A—C9A	118.75 (15)	C9B—C4B—C5B	118.61 (16)
C5A—C4A—C3A	119.48 (15)	C9B—C4B—C3B	122.90 (15)
C9A—C4A—C3A	121.75 (16)	C5B—C4B—C3B	118.48 (17)
C8A—C9A—C4A	120.31 (17)	C8B—C9B—C4B	120.39 (18)
C8A—C9A—H9A	119.8	C8B—C9B—H9B	119.8
C4A—C9A—H9A	119.8	C4B—C9B—H9B	119.8
C7A—C8A—C9A	120.56 (16)	C9B—C8B—C7B	119.7 (2)
C7A—C8A—H8A	119.7	C9B—C8B—H8B	120.1
C9A—C8A—H8A	119.7	C7B—C8B—H8B	120.1
C8A—C7A—C6A	119.56 (15)	C6B—C7B—C8B	120.36 (18)
C8A—C7A—H7A	120.2	C6B—C7B—H7B	119.8
C6A—C7A—H7A	120.2	C8B—C7B—H7B	119.8
C7A—C6A—C5A	120.21 (17)	C7B—C6B—C5B	120.00 (19)
C7A—C6A—H6A	119.9	C7B—C6B—H6B	120
C5A—C6A—H6A	119.9	C5B—C6B—H6B	120
C4A—C5A—C6A	120.61 (16)	C6B—C5B—C4B	120.9 (2)
C4A—C5A—H5A	119.7	C6B—C5B—H5B	119.5
C6A—C5A—H5A	119.7	C4B—C5B—H5B	119.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2AO···O1B^i	0.86 (2)	1.89 (2)	2.746 (2)	171 (2)
O2B—H2BO···O2A^ii	0.88 (3)	1.90 (3)	2.748 (2)	160 (2)
C10A—H10A···O2B^iii	0.99	2.45	3.314 (2)	146
C2B—H2B···O1A	0.95	2.35	3.237 (2)	156

Symmetry codes: (i) x, y+1, z; (ii) x, −y+1/2, z−1/2; (iii) −x+2, −y, −z+1.