Experimental charge-density study of paracetamol – multipole refinement in the presence of a disordered methyl group

A high-resolution single-crystal X-ray study of paracetamol has been performed at 85 K. Different approaches to modeling the experimental electron density (ED) were tested for the dynamically disordered portions of the molecule in order to check to what extent it is possible to obtain a proper ED distribution in the ordered part. Models were examined in which the methyl-group ED was built from pseudoatoms taken from the University at Buffalo Pseudoatom Databank or the Invariom database, with multipole parameters for the remaining atoms being obtained from free refinement. The κ′ restricted multipolar model (KRMM) and free κ′ refinements were compared; restriction of the κ′ parameters was essential in order to obtain values of the electrostatic interaction energy consistent with the results of theoretical single-point periodic calculations. After simultaneous use of KRMM refinement and the databases to model the methyl group, the bond critical point properties and interaction electrostatic energy values were found to be closer to those obtained from theory. Additionally, some discrepancies in the ED distribution and dipole moment among transferred aspherical atom model refinements utilizing both theoretical databases and parameters from theoretical periodic calculations are shown. Including the influence of the crystal field in the periodic calculations increases the ED in the hydroxyl and amide groups, thus leading to higher values of the electrostatic interaction energy, changes in the electrostatic potential values mapped on the isodensity surface and changes in the shape of the anisotropic displacement parameters with respect to results found for both database models.

Computing details

For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT. Program(s) used to solve structure: SHELXL97 (Sheldrick, 1997) for TAAM_IM, TAAM_THEOR, TAAM_UB, IAM. For all compounds, program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).

Figures

(TAAM_IM)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	109 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.02	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.02	(Δ/σ)max < 0.001
S = 2.45	Δρmax = 0.30 e Å^−3
6706 reflections	Δρmin = −0.21 e Å^−3

Special details

Refinement. Refinement was performed on F with the program XDLSM against high resolution data. Positions and anisotropic ADPs of non hydrogen atoms and isotropic ADPs of hydrogen atoms were refined within transfered aspherical atom model (TAAM) refinement with pseudoatoms parameters from the invariom database used. Hydrogen atom positions were obtained by elongating the bond length along the vector of the atom they are attached to and their refined positions from the independent atom model to the theoretical positions. The following dummy atoms were used: DUM1 - 0.158 0.2633 0.4447 DUM2 - 0.0694 0.2369 0.4598

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16381 (2)	0.076275 (17)	0.277645 (14)	0.015
O(2)	−0.35322 (2)	0.506298 (19)	0.691483 (14)	0.016
N(1)	−0.05178 (2)	0.449184 (17)	0.660611 (14)	0.011
C(1)	−0.08801 (2)	0.357579 (18)	0.561863 (15)	0.01
C(2)	−0.25816 (2)	0.357373 (19)	0.485126 (15)	0.011
C(3)	−0.28052 (2)	0.26287 (2)	0.390101 (16)	0.012
C(4)	−0.13376 (2)	0.168897 (19)	0.370452 (15)	0.011
C(5)	0.03795 (3)	0.17147 (2)	0.445652 (17)	0.013
C(6)	0.06005 (2)	0.26526 (2)	0.540650 (16)	0.012
C(7)	−0.17857 (2)	0.514741 (19)	0.719619 (15)	0.011
C(8)	−0.09276 (3)	0.60218 (2)	0.823959 (18)	0.016
H(1)	−0.372829	0.430511	0.499162	0.0283 (11)
H(2)	−0.414024	0.263329	0.331915	0.0271 (11)
H(3)	0.153441	0.099334	0.43123	0.0310 (12)
H(4)	0.192186	0.266857	0.600111	0.0317 (12)
H(5)	−0.045942	0.038222	0.257816	0.0280 (12)
H(6)	0.086645	0.460604	0.694003	0.0256 (11)
H(7)	−0.107912	0.7181	0.803533	0.0502 (17)
H(8)	0.057851	0.577427	0.85028	0.062 (2)
H(9)	−0.173846	0.5799	0.895681	0.0512 (18)
DUM1	−0.158	0.2633	0.4447	0
DUM2	−0.0694	0.2369	0.4598	0

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01040 (5)	0.01803 (6)	0.01489 (6)	0.00055 (4)	−0.00018 (4)	−0.00533 (4)
O(2)	0.00961 (5)	0.02358 (7)	0.01506 (6)	0.00208 (4)	0.00349 (4)	−0.00134 (5)
N(1)	0.00891 (5)	0.01266 (5)	0.01085 (5)	0.00050 (4)	0.00135 (4)	−0.00115 (4)
C(1)	0.00817 (5)	0.01088 (5)	0.00973 (5)	0.00100 (4)	0.00089 (4)	0.00009 (4)
C(2)	0.00856 (5)	0.01314 (6)	0.01142 (6)	0.00199 (4)	0.00030 (4)	−0.00043 (5)
C(3)	0.00861 (5)	0.01432 (6)	0.01169 (6)	0.00152 (4)	−0.00027 (4)	−0.00107 (5)
C(4)	0.00878 (5)	0.01250 (6)	0.01101 (6)	0.00059 (4)	0.00033 (4)	−0.00112 (4)
C(5)	0.00942 (6)	0.01519 (6)	0.01368 (6)	0.00320 (4)	−0.00081 (5)	−0.00328 (5)
C(6)	0.00915 (5)	0.01489 (6)	0.01252 (6)	0.00292 (4)	−0.00098 (4)	−0.00263 (5)
C(7)	0.01060 (5)	0.01240 (6)	0.01089 (6)	0.00077 (4)	0.00271 (4)	−0.00033 (5)
C(8)	0.01720 (7)	0.01669 (7)	0.01512 (7)	−0.00108 (5)	0.00410 (6)	−0.00445 (5)

Geometric parameters (Å, º)

O(1)—C(4)	1.3631 (2)	C(3)—C(4)	1.3923 (2)
O(1)—H(5)	0.9607 (1)	C(3)—H(2)	1.0823 (2)
O(2)—C(7)	1.2365 (2)	C(4)—C(5)	1.3943 (2)
N(1)—C(1)	1.4133 (2)	C(5)—C(6)	1.3879 (3)
N(1)—C(7)	1.3423 (2)	C(5)—H(3)	1.0823 (2)
N(1)—H(6)	1.0079 (2)	C(6)—H(4)	1.0823 (2)
C(1)—C(2)	1.3945 (2)	C(7)—C(8)	1.5063 (3)
C(1)—C(6)	1.3951 (2)	C(8)—H(7)	1.0914 (2)
C(2)—C(3)	1.3922 (2)	C(8)—H(8)	1.0914 (2)
C(2)—H(1)	1.0823 (2)	C(8)—H(9)	1.0914 (2)
C(4)—O(1)—H(5)	111.605 (14)	C(4)—C(5)—C(6)	119.911 (16)
C(1)—N(1)—C(7)	128.183 (15)	C(4)—C(5)—H(3)	120.346 (16)
C(1)—N(1)—H(6)	115.503 (14)	C(6)—C(5)—H(3)	119.734 (16)
C(7)—N(1)—H(6)	116.156 (15)	C(1)—C(6)—C(5)	120.674 (16)
N(1)—C(1)—C(2)	124.096 (15)	C(1)—C(6)—H(4)	118.952 (16)
N(1)—C(1)—C(6)	116.493 (15)	C(5)—C(6)—H(4)	120.369 (16)
C(2)—C(1)—C(6)	119.392 (16)	O(2)—C(7)—N(1)	123.495 (17)
C(1)—C(2)—C(3)	119.890 (15)	O(2)—C(7)—C(8)	121.513 (17)
C(1)—C(2)—H(1)	120.210 (16)	N(1)—C(7)—C(8)	114.990 (15)
C(3)—C(2)—H(1)	119.900 (15)	C(7)—C(8)—H(7)	109.169 (18)
C(2)—C(3)—C(4)	120.549 (15)	C(7)—C(8)—H(8)	112.559 (17)
C(2)—C(3)—H(2)	118.934 (16)	C(7)—C(8)—H(9)	108.297 (17)
C(4)—C(3)—H(2)	120.517 (16)	H(7)—C(8)—H(8)	109.040 (18)
O(1)—C(4)—C(3)	118.396 (15)	H(7)—C(8)—H(9)	107.512 (17)
O(1)—C(4)—C(5)	122.049 (16)	H(8)—C(8)—H(9)	110.133 (19)
C(3)—C(4)—C(5)	119.555 (16)

(TAAM_THEOR)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	67 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.018	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.018	(Δ/σ)max < 0.001
S = 2.22	Δρmax = 0.24 e Å^−3
6706 reflections	Δρmin = −0.20 e Å^−3

Special details

Refinement. Refinement was performed on F with the program XDLSM against high resolution data. Positions and anisotropic ADPs of non hydrogen atoms were refined within transfered aspherical atom model (TAAM) refinement with pseudoatoms parameters from the theoretical periodic calculations used. Hydrogen atom positions were taken from 80 K neutron diffraction data (Wilson, 1997), except the H7, H8, H9 atom positions. This were obtained by elongating the bond length to 1.091 A.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.163828 (18)	0.076277 (16)	−0.722341 (12)	0.015
O(2)	−0.353079 (19)	0.506293 (17)	−0.308490 (13)	0.016
N(1)	−0.051790 (19)	0.449130 (16)	−0.339441 (12)	0.011
C(1)	−0.08802 (2)	0.357582 (16)	−0.438146 (13)	0.010
C(2)	−0.25814 (2)	0.357372 (18)	−0.514883 (14)	0.011
C(3)	−0.28049 (2)	0.262865 (18)	−0.609885 (14)	0.012
C(4)	−0.13375 (2)	0.168902 (17)	−0.629542 (14)	0.011
C(5)	0.03794 (2)	0.171479 (19)	−0.554358 (15)	0.013
C(6)	0.06005 (2)	0.265265 (18)	−0.459367 (15)	0.013
C(7)	−0.17853 (2)	0.514787 (17)	−0.280336 (14)	0.011
C(8)	−0.09274 (3)	0.60217 (2)	−0.176042 (17)	0.016
H(1)	−0.3745	0.4295	−0.501	0.028
H(2)	−0.4106	0.2643	−0.6694	0.031
H(3)	0.1516	0.0988	−0.569	0.032
H(4)	0.1892	0.2646	−0.4015	0.031
H(5)	−0.0438	0.0379	−0.7435	0.026
H(6)	0.0882	0.4585	−0.3054	0.028
H(7)	−0.177174	0.587082	−0.104805	0.037
H(8)	0.058605	0.577445	−0.153064	0.038
H(9)	−0.104153	0.717672	−0.198503	0.038

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01019 (4)	0.01819 (5)	0.01496 (5)	0.00065 (4)	−0.00025 (4)	−0.00535 (4)
O(2)	0.01005 (4)	0.02327 (6)	0.01470 (5)	0.00205 (4)	0.00353 (4)	−0.00130 (4)
N(1)	0.00880 (4)	0.01273 (5)	0.01097 (5)	0.00056 (3)	0.00139 (3)	−0.00117 (4)
C(1)	0.00829 (5)	0.01095 (5)	0.00981 (5)	0.00088 (4)	0.00098 (4)	0.00029 (4)
C(2)	0.00863 (5)	0.01323 (5)	0.01153 (5)	0.00201 (4)	0.00035 (4)	−0.00041 (4)
C(3)	0.00875 (5)	0.01438 (6)	0.01173 (5)	0.00142 (4)	−0.00023 (4)	−0.00096 (4)
C(4)	0.00895 (5)	0.01254 (5)	0.01103 (5)	0.00052 (4)	0.00041 (4)	−0.00103 (4)
C(5)	0.00964 (5)	0.01517 (6)	0.01375 (6)	0.00311 (4)	−0.00069 (4)	−0.00316 (4)
C(6)	0.00924 (5)	0.01500 (6)	0.01260 (6)	0.00292 (4)	−0.00098 (4)	−0.00260 (4)
C(7)	0.01034 (5)	0.01251 (5)	0.01132 (5)	0.00087 (4)	0.00279 (4)	0.00003 (4)
C(8)	0.01734 (7)	0.01679 (7)	0.01527 (6)	−0.00107 (5)	0.00415 (5)	−0.00446 (5)
H(1)	0.019896	0.033928	0.029873	0.012322	0.00102	−0.006
H(2)	0.017879	0.044741	0.027643	0.007036	−0.007724	−0.008856
H(3)	0.022443	0.036371	0.035067	0.014387	−0.001873	−0.012308
H(4)	0.018413	0.042682	0.029905	0.008791	−0.008879	−0.011359
H(5)	0.018782	0.031821	0.028553	0.003628	0.002377	−0.009856
H(6)	0.015038	0.037498	0.029209	0.000258	−0.000677	−0.010966
H(7)	0.037933	0.050554	0.026026	−0.009017	0.01562	−0.007783
H(8)	0.021525	0.050832	0.039604	0.005464	−0.001589	−0.015658
H(9)	0.053331	0.022368	0.037228	−0.000745	0.003544	−0.002732

Geometric parameters (Å, º)

O(1)—C(4)	1.3631 (2)	C(3)—C(4)	1.3922 (2)
O(1)—H(5)	0.9812 (1)	C(3)—H(2)	1.0715 (2)
O(2)—C(7)	1.2359 (2)	C(4)—C(5)	1.3941 (2)
N(1)—C(1)	1.4126 (2)	C(5)—C(6)	1.3878 (2)
N(1)—C(7)	1.3431 (2)	C(5)—H(3)	1.0760 (2)
N(1)—H(6)	1.0182 (1)	C(6)—H(4)	1.0562 (2)
C(1)—C(2)	1.3944 (2)	C(7)—C(8)	1.5055 (2)
C(1)—C(6)	1.3951 (2)	C(8)—H(7)	1.0916 (2)
C(2)—C(3)	1.3920 (2)	C(8)—H(8)	1.0914 (2)
C(2)—H(1)	1.0854 (2)	C(8)—H(9)	1.0913 (2)
C(4)—O(1)—H(5)	111.938 (12)	C(4)—C(5)—C(6)	119.911 (15)
C(1)—N(1)—C(7)	128.230 (14)	C(4)—C(5)—H(3)	119.834 (15)
C(1)—N(1)—H(6)	114.951 (13)	C(6)—C(5)—H(3)	120.238 (14)
C(7)—N(1)—H(6)	116.580 (14)	C(1)—C(6)—C(5)	120.675 (14)
N(1)—C(1)—C(2)	124.107 (14)	C(1)—C(6)—H(4)	119.821 (15)
N(1)—C(1)—C(6)	116.490 (13)	C(5)—C(6)—H(4)	119.486 (15)
C(2)—C(1)—C(6)	119.386 (14)	O(2)—C(7)—N(1)	123.415 (16)
C(1)—C(2)—C(3)	119.892 (14)	O(2)—C(7)—C(8)	121.547 (15)
C(1)—C(2)—H(1)	120.735 (15)	N(1)—C(7)—C(8)	115.036 (14)
C(3)—C(2)—H(1)	119.371 (14)	C(7)—C(8)—H(7)	109.624 (15)
C(2)—C(3)—C(4)	120.556 (14)	C(7)—C(8)—H(8)	111.027 (15)
C(2)—C(3)—H(2)	119.632 (14)	C(7)—C(8)—H(9)	108.507 (16)
C(4)—C(3)—H(2)	119.798 (15)	H(7)—C(8)—H(8)	114.231 (18)
O(1)—C(4)—C(3)	118.395 (14)	H(7)—C(8)—H(9)	105.830 (16)
O(1)—C(4)—C(5)	122.052 (14)	H(8)—C(8)—H(9)	107.326 (16)
C(3)—C(4)—C(5)	119.553 (14)

(TAAM_UB)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	0 parameters
Least-squares matrix: full	538976288 restraints
R[F^2 > 2σ(F^2)] = 0.016	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.019	(Δ/σ)max < 0.001
S = 3.27	Δρmax = 0.21 e Å^−3
2021 reflections	Δρmin = −0.10 e Å^−3

Special details

Refinement. Refinement was performed on F with the program XDLSM against high resolution data. Positions and anisotropic ADPs of non hydrogen atoms and isotropic ADPs of hydrogen atoms were refined within transfered aspherical atom model (TAAM) refinement with pseudoatoms parameters from the UBDB database used. Hydrogen atom positions were obtained by elongating the bond length along the vector of the atom they are attached to and their refined positions from the independent atom model to the standard neutron positions positions. The following dummy atoms were used: DUM0 - 0.1335 0.4361 0.6408 DUM1 - 0.1104 0.2639 0.4656

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

	x	y	z	Uiso*/Ueq
O(1)	−0.163752	0.07629	0.277669	0.015
O(2)	−0.353025	0.506297	0.691509	0.016
N(1)	−0.051776	0.449148	0.660577	0.011
C(1)	−0.08802	0.357581	0.561857	0.01
C(2)	−0.258184	0.357378	0.485103	0.011
C(3)	−0.28053	0.262887	0.390114	0.012
C(4)	−0.133751	0.168901	0.370455	0.011
C(5)	0.037965	0.171478	0.445656	0.013
C(6)	0.060065	0.265238	0.540637	0.013
C(7)	−0.17849	0.514798	0.719682	0.011
C(8)	−0.092757	0.602173	0.823954	0.016
H(1)	−0.373729	0.429634	0.499452	0.0278 (11)
H(2)	−0.41389	0.264059	0.331666	0.0287 (11)
H(3)	0.153602	0.099994	0.430063	0.0302 (11)
H(4)	0.1934	0.267022	0.599096	0.0319 (12)
H(5)	−0.044377	0.03763	0.259678	0.0274 (11)
H(6)	0.086702	0.459506	0.69455	0.0230 (10)
H(7)	−0.108353	0.714507	0.80377	0.0535 (17)
H(8)	0.053807	0.579577	0.849385	0.0592 (18)
H(9)	−0.173332	0.58425	0.893261	0.0508 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01035 (5)	0.01809 (6)	0.01488 (5)	0.00047 (4)	−0.00028 (4)	−0.00530 (4)
O(2)	0.00997 (4)	0.02330 (6)	0.01475 (5)	0.00211 (4)	0.00357 (4)	−0.00141 (4)
N(1)	0.00898 (4)	0.01268 (5)	0.01095 (5)	0.00056 (3)	0.00141 (4)	−0.00108 (4)
C(1)	0.00835 (5)	0.01099 (5)	0.00987 (5)	0.00092 (4)	0.00098 (4)	0.00027 (4)
C(2)	0.00866 (5)	0.01331 (6)	0.01154 (6)	0.00198 (4)	0.00028 (4)	−0.00041 (4)
C(3)	0.00877 (5)	0.01443 (6)	0.01184 (6)	0.00148 (4)	−0.00021 (4)	−0.00101 (4)
C(4)	0.00897 (5)	0.01260 (5)	0.01113 (5)	0.00053 (4)	0.00042 (4)	−0.00095 (4)
C(5)	0.00961 (5)	0.01529 (6)	0.01381 (6)	0.00314 (4)	−0.00076 (4)	−0.00322 (5)
C(6)	0.00928 (5)	0.01503 (6)	0.01270 (6)	0.00296 (4)	−0.00095 (4)	−0.00262 (5)
C(7)	0.01035 (5)	0.01258 (5)	0.01142 (5)	0.00088 (4)	0.00280 (4)	0.00014 (4)
C(8)	0.01739 (7)	0.01684 (7)	0.01527 (7)	−0.00107 (5)	0.00415 (5)	−0.00445 (5)

Geometric parameters (Å, º)

O(1)—C(4)	1.3629 (2)	C(3)—C(4)	1.3925 (2)
O(1)—H(5)	0.9650 (1)	C(3)—H(2)	1.0830 (2)
O(2)—C(7)	1.2358 (2)	C(4)—C(5)	1.3943 (2)
N(1)—C(1)	1.4129 (2)	C(5)—C(6)	1.3876 (2)
N(1)—C(7)	1.3430 (2)	C(5)—H(3)	1.0830 (2)
N(1)—H(6)	1.0090 (1)	C(6)—H(4)	1.0830 (2)
C(1)—C(2)	1.3947 (2)	C(7)—C(8)	1.5052 (2)
C(1)—C(6)	1.3953 (2)	C(8)—H(7)	1.0590 (2)
C(2)—C(3)	1.3918 (2)	C(8)—H(8)	1.0590 (2)
C(2)—H(1)	1.0830 (2)	C(8)—H(9)	1.0590 (2)
C(4)—O(1)—H(5)	110.669 (13)	C(4)—C(5)—C(6)	119.913 (15)
C(1)—N(1)—C(7)	128.232 (14)	C(4)—C(5)—H(3)	119.962 (15)
C(1)—N(1)—H(6)	115.450 (13)	C(6)—C(5)—H(3)	120.125 (15)
C(7)—N(1)—H(6)	116.109 (14)	C(1)—C(6)—C(5)	120.675 (15)
N(1)—C(1)—C(2)	124.107 (14)	C(1)—C(6)—H(4)	119.461 (15)
N(1)—C(1)—C(6)	116.489 (14)	C(5)—C(6)—H(4)	119.864 (15)
C(2)—C(1)—C(6)	119.387 (15)	O(2)—C(7)—N(1)	123.400 (16)
C(1)—C(2)—C(3)	119.890 (14)	O(2)—C(7)—C(8)	121.547 (16)
C(1)—C(2)—H(1)	120.366 (15)	N(1)—C(7)—C(8)	115.051 (14)
C(3)—C(2)—H(1)	119.742 (14)	C(7)—C(8)—H(7)	108.842 (17)
C(2)—C(3)—C(4)	120.554 (14)	C(7)—C(8)—H(8)	112.957 (16)
C(2)—C(3)—H(2)	118.805 (15)	C(7)—C(8)—H(9)	108.967 (16)
C(4)—C(3)—H(2)	120.641 (15)	H(7)—C(8)—H(8)	108.672 (17)
O(1)—C(4)—C(3)	118.412 (14)	H(7)—C(8)—H(9)	105.517 (17)
O(1)—C(4)—C(5)	122.035 (15)	H(8)—C(8)—H(9)	111.587 (18)
C(3)—C(4)—C(5)	119.552 (15)

(M_UBkrmm)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	364 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.017	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.017	(Δ/σ)max < 0.001
S = 2.07	Δρmax = 0.29 e Å^−3
6706 reflections	Δρmin = −0.22 e Å^−3

Special details

Refinement. KRMM Multipolar refinement was performed on F with the program XDLSM against high resolution data, except four atoms: C8, H7, H8, H9. Hydrogen atom positions were taken from 80 K neutron diffraction data (Wilson, 1997), except the H7, H8, H9 atom positions. This were obtained by elongating the bond length along the vector of the atom they are attached to and their neutron positions. Anisotropic ADPs for hydrogen atoms were generated by the SHADE program. Pseudoatoms paramiters for the C8, H7, H8, H9 atoms were taken from the UBDB database.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16391 (4)	0.07618 (3)	−0.72231 (2)	0.015
O(2)	−0.35322 (4)	0.50644 (4)	−0.30854 (3)	0.016
N(1)	−0.05184 (3)	0.44908 (2)	−0.339478 (17)	0.011
C(1)	−0.08803 (2)	0.357586 (17)	−0.438135 (14)	0.01
C(2)	−0.25816 (2)	0.357375 (19)	−0.514880 (15)	0.011
C(3)	−0.28044 (2)	0.26286 (2)	−0.609907 (16)	0.012
C(4)	−0.13374 (2)	0.168900 (18)	−0.629551 (15)	0.011
C(5)	0.03795 (3)	0.17148 (2)	−0.554348 (16)	0.013
C(6)	0.06004 (2)	0.26528 (2)	−0.459357 (16)	0.012
C(7)	−0.17856 (2)	0.514821 (17)	−0.280342 (14)	0.011
C(8)	−0.09279	0.602135	−0.17606	0.016
H(1)	−0.3745	0.4295	−0.501	0.028
H(2)	−0.4106	0.2643	−0.6694	0.031
H(3)	0.1516	0.0988	−0.569	0.032
H(4)	0.1892	0.2646	−0.4015	0.031
H(5)	−0.0438	0.0379	−0.7435	0.026
H(6)	0.0882	0.4585	−0.3054	0.028
H(7)	−0.17468	0.58757	−0.10693	0.038
H(8)	0.05413	0.57829	−0.15374	0.038
H(9)	−0.10382	0.71426	−0.19783	0.039

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01031 (8)	0.01806 (9)	0.01484 (9)	0.00077 (6)	0.00008 (7)	−0.00574 (8)
O(2)	0.00981 (8)	0.02333 (11)	0.01475 (9)	0.00190 (7)	0.00359 (7)	−0.00136 (9)
N(1)	0.00872 (6)	0.01274 (6)	0.01091 (6)	0.00052 (4)	0.00146 (5)	−0.00151 (5)
C(1)	0.00826 (5)	0.01090 (5)	0.00968 (5)	0.00088 (4)	0.00097 (4)	0.00022 (4)
C(2)	0.00860 (6)	0.01313 (6)	0.01143 (6)	0.00205 (4)	0.00028 (5)	−0.00051 (5)
C(3)	0.00870 (5)	0.01426 (6)	0.01168 (6)	0.00147 (4)	−0.00028 (5)	−0.00099 (5)
C(4)	0.00894 (5)	0.01240 (6)	0.01098 (6)	0.00055 (4)	0.00042 (4)	−0.00107 (5)
C(5)	0.00960 (6)	0.01508 (7)	0.01368 (7)	0.00314 (5)	−0.00072 (5)	−0.00321 (5)
C(6)	0.00923 (6)	0.01487 (6)	0.01252 (6)	0.00291 (5)	−0.00101 (5)	−0.00266 (5)
C(7)	0.01025 (6)	0.01246 (5)	0.01129 (6)	0.00083 (4)	0.00276 (4)	−0.00001 (4)
C(8)	0.01744	0.017021	0.015253	−0.001085	0.004072	−0.004505
H(1)	0.019896	0.033928	0.029873	0.012322	0.00102	−0.006
H(2)	0.017879	0.044741	0.027643	0.007036	−0.007724	−0.008856
H(3)	0.022443	0.036371	0.035067	0.014387	−0.001873	−0.012308
H(4)	0.018413	0.042682	0.029905	0.008791	−0.008879	−0.011359
H(5)	0.018782	0.031821	0.028553	0.003628	0.002377	−0.009856
H(6)	0.015038	0.037498	0.029209	0.000258	−0.000677	−0.010966
H(7)	0.0384	0.0515	0.026653	−0.009049	0.01588	−0.007924
H(8)	0.02209	0.050884	0.039922	0.005281	−0.001232	−0.01538
H(9)	0.054321	0.023014	0.037554	−0.000395	0.003514	−0.002648

Geometric parameters (Å, º)

O(1)—C(4)	1.3633 (3)	C(3)—C(4)	1.3918 (2)
O(1)—H(5)	0.9815 (3)	C(3)—H(2)	1.0716 (2)
O(2)—C(7)	1.2367 (3)	C(4)—C(5)	1.3942 (2)
N(1)—C(1)	1.4119 (2)	C(5)—C(6)	1.3879 (2)
N(1)—C(7)	1.3436 (2)	C(5)—H(3)	1.0759 (2)
N(1)—H(6)	1.0187 (2)	C(6)—H(4)	1.0563 (2)
C(1)—C(2)	1.3945 (2)	C(7)—C(8)	1.5051 (2)
C(1)—C(6)	1.3950 (2)	C(8)—H(7)	1.0590
C(2)—C(3)	1.3923 (2)	C(8)—H(8)	1.0592
C(2)—H(1)	1.0853 (2)	C(8)—H(9)	1.0593
C(4)—O(1)—H(5)	111.89 (2)	C(4)—C(5)—C(6)	119.908 (16)
C(1)—N(1)—C(7)	128.260 (17)	C(4)—C(5)—H(3)	119.823 (17)
C(1)—N(1)—H(6)	114.974 (16)	C(6)—C(5)—H(3)	120.253 (16)
C(7)—N(1)—H(6)	116.530 (18)	C(1)—C(6)—C(5)	120.683 (16)
N(1)—C(1)—C(2)	124.105 (15)	C(1)—C(6)—H(4)	119.832 (16)
N(1)—C(1)—C(6)	116.494 (15)	C(5)—C(6)—H(4)	119.467 (16)
C(2)—C(1)—C(6)	119.384 (16)	O(2)—C(7)—N(1)	123.41 (2)
C(1)—C(2)—C(3)	119.877 (16)	O(2)—C(7)—C(8)	121.533 (19)
C(1)—C(2)—H(1)	120.733 (16)	N(1)—C(7)—C(8)	115.056 (14)
C(3)—C(2)—H(1)	119.388 (15)	C(7)—C(8)—H(7)	109.664 (6)
C(2)—C(3)—C(4)	120.573 (16)	C(7)—C(8)—H(8)	111.091 (6)
C(2)—C(3)—H(2)	119.595 (16)	C(7)—C(8)—H(9)	108.515 (6)
C(4)—C(3)—H(2)	119.819 (16)	H(7)—C(8)—H(8)	114.2385
O(1)—C(4)—C(3)	118.386 (18)	H(7)—C(8)—H(9)	105.7921
O(1)—C(4)—C(5)	122.065 (18)	H(8)—C(8)—H(9)	107.2357
C(3)—C(4)—C(5)	119.548 (16)

(M_IMkrmm)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	364 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.017	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.016	(Δ/σ)max < 0.001
S = 2.05	Δρmax = 0.27 e Å^−3
6706 reflections	Δρmin = −0.20 e Å^−3

Special details

Refinement. KRMM Multipolar refinement was performed on F with the program XDLSM against high resolution data, except four atoms: C8, H7, H8, H9. Hydrogen atom positions were taken from 80 K neutron diffraction data (Wilson, 1997), except the H7, H8, H9 atom positions. This were obtained by elongating the bond length along the vector of the atom they are attached to and their neutron positions. Anisotropic ADPs for hydrogen atoms were generated by the SHADE program. Pseudoatoms paramiters for the C8, H7, H8, H9 atoms were taken from the invariom database.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16390 (4)	0.07618 (3)	−0.72232 (2)	0.014
O(2)	−0.35323 (4)	0.50644 (4)	−0.30854 (3)	0.016
N(1)	−0.05182 (3)	0.44909 (2)	−0.339480 (17)	0.011
C(1)	−0.08803 (2)	0.357580 (17)	−0.438134 (14)	0.009
C(2)	−0.25817 (2)	0.357381 (19)	−0.514879 (15)	0.011
C(3)	−0.28045 (2)	0.26286 (2)	−0.609912 (16)	0.011
C(4)	−0.13373 (2)	0.168900 (18)	−0.629551 (15)	0.011
C(5)	0.03795 (3)	0.17147 (2)	−0.554350 (17)	0.013
C(6)	0.06003 (3)	0.26527 (2)	−0.459355 (16)	0.012
C(7)	−0.17856 (2)	0.514835 (18)	−0.280335 (15)	0.011
C(8)	−0.092683	0.602303	−0.176031	0.016
H(1)	−0.3745	0.4295	−0.501	0.028
H(2)	−0.4106	0.2643	−0.6694	0.031
H(3)	0.1516	0.0988	−0.569	0.032
H(4)	0.1892	0.2646	−0.4015	0.031
H(5)	−0.0438	0.0379	−0.7435	0.026
H(6)	0.0882	0.4585	−0.3054	0.028
H(7)	−0.177138	0.587087	−0.104835	0.037
H(8)	0.058636	0.577432	−0.153052	0.038
H(9)	−0.10417	0.717814	−0.198529	0.038

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01013 (8)	0.01790 (10)	0.01464 (9)	0.00077 (7)	0.00005 (7)	−0.00572 (8)
O(2)	0.00964 (8)	0.02314 (11)	0.01455 (9)	0.00191 (7)	0.00355 (7)	−0.00135 (9)
N(1)	0.00848 (6)	0.01256 (6)	0.01068 (6)	0.00054 (5)	0.00144 (5)	−0.00151 (5)
C(1)	0.00798 (5)	0.01067 (5)	0.00940 (6)	0.00088 (4)	0.00091 (4)	0.00020 (4)
C(2)	0.00833 (6)	0.01283 (6)	0.01118 (6)	0.00204 (4)	0.00024 (5)	−0.00050 (5)
C(3)	0.00845 (6)	0.01397 (6)	0.01140 (6)	0.00147 (5)	−0.00031 (5)	−0.00099 (5)
C(4)	0.00867 (6)	0.01215 (6)	0.01070 (6)	0.00054 (4)	0.00039 (4)	−0.00109 (5)
C(5)	0.00931 (6)	0.01484 (7)	0.01338 (7)	0.00313 (5)	−0.00076 (5)	−0.00322 (5)
C(6)	0.00897 (6)	0.01458 (7)	0.01223 (6)	0.00291 (5)	−0.00103 (5)	−0.00264 (5)
C(7)	0.00994 (6)	0.01226 (6)	0.01103 (6)	0.00083 (4)	0.00273 (4)	0.00003 (5)
C(8)	0.017008	0.015956	0.014662	−0.001121	0.004059	−0.004444
H(1)	0.019896	0.033928	0.029873	0.012322	0.00102	−0.006
H(2)	0.017879	0.044741	0.027643	0.007036	−0.007724	−0.008856
H(3)	0.022443	0.036371	0.035067	0.014387	−0.001873	−0.012308
H(4)	0.018413	0.042682	0.029905	0.008791	−0.008879	−0.011359
H(5)	0.018782	0.031821	0.028553	0.003628	0.002377	−0.009856
H(6)	0.015038	0.037498	0.029209	0.000258	−0.000677	−0.010966
H(7)	0.037933	0.050554	0.026026	−0.009017	0.01562	−0.007783
H(8)	0.021525	0.050832	0.039604	0.005464	−0.001589	−0.015658
H(9)	0.053331	0.022368	0.037228	−0.000745	0.003544	−0.002732

Geometric parameters (Å, º)

O(1)—C(4)	1.3634 (3)	C(3)—C(4)	1.3920 (2)
O(1)—H(5)	0.9813 (3)	C(3)—H(2)	1.0715 (2)
O(2)—C(7)	1.2368 (3)	C(4)—C(5)	1.3941 (2)
N(1)—C(1)	1.4120 (2)	C(5)—C(6)	1.3880 (3)
N(1)—C(7)	1.3438 (2)	C(5)—H(3)	1.0759 (2)
N(1)—H(6)	1.0185 (2)	C(6)—H(4)	1.0563 (2)
C(1)—C(2)	1.3945 (2)	C(7)—C(8)	1.5062 (2)
C(1)—C(6)	1.3950 (2)	C(8)—H(7)	1.0914
C(2)—C(3)	1.3924 (2)	C(8)—H(8)	1.0914
C(2)—H(1)	1.0852 (2)	C(8)—H(9)	1.0915
C(4)—O(1)—H(5)	111.88 (2)	C(4)—C(5)—C(6)	119.904 (17)
C(1)—N(1)—C(7)	128.252 (17)	C(4)—C(5)—H(3)	119.826 (17)
C(1)—N(1)—H(6)	114.979 (17)	C(6)—C(5)—H(3)	120.252 (17)
C(7)—N(1)—H(6)	116.531 (18)	C(1)—C(6)—C(5)	120.685 (16)
N(1)—C(1)—C(2)	124.104 (16)	C(1)—C(6)—H(4)	119.831 (17)
N(1)—C(1)—C(6)	116.490 (16)	C(5)—C(6)—H(4)	119.466 (17)
C(2)—C(1)—C(6)	119.388 (16)	O(2)—C(7)—N(1)	123.40 (2)
C(1)—C(2)—C(3)	119.872 (16)	O(2)—C(7)—C(8)	121.549 (19)
C(1)—C(2)—H(1)	120.736 (16)	N(1)—C(7)—C(8)	115.045 (14)
C(3)—C(2)—H(1)	119.389 (16)	C(7)—C(8)—H(7)	109.543 (6)
C(2)—C(3)—C(4)	120.570 (16)	C(7)—C(8)—H(8)	110.989 (6)
C(2)—C(3)—H(2)	119.596 (16)	C(7)—C(8)—H(9)	108.500 (6)
C(4)—C(3)—H(2)	119.820 (17)	H(7)—C(8)—H(8)	114.2119
O(1)—C(4)—C(3)	118.382 (18)	H(7)—C(8)—H(9)	105.8858
O(1)—C(4)—C(5)	122.064 (18)	H(8)—C(8)—H(9)	107.4246
C(3)—C(4)—C(5)	119.552 (16)

(M_UB)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	364 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.017	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.017	(Δ/σ)max < 0.001
S = 2.07	Δρmax = 0.27 e Å^−3
6706 reflections	Δρmin = −0.15 e Å^−3

Special details

Refinement. Multipolar refinement was performed on F with the program XDLSM against high resolution data, except four atoms: C8, H7, H8, H9. Hydrogen atom positions were taken from 80 K neutron diffraction data (Wilson, 1997), except the H7, H8, H9 atom positions. This were obtained by elongating the bond length along the vector of the atom they are attached to and their neutron positions. Anisotropic ADPs for hydrogen atoms were generated by the SHADE program. Pseudoatoms paramiters for the C8, H7, H8, H9 atoms were taken from the UBDB database.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16401 (3)	0.07616 (3)	−0.72238 (2)	0.014
O(2)	−0.35332 (3)	0.50638 (3)	−0.30856 (2)	0.016
N(1)	−0.05184 (3)	0.44909 (2)	−0.339474 (17)	0.011
C(1)	−0.08804 (2)	0.357585 (18)	−0.438134 (15)	0.009
C(2)	−0.25816 (2)	0.35737 (2)	−0.514884 (16)	0.011
C(3)	−0.28044 (2)	0.26286 (2)	−0.609901 (16)	0.011
C(4)	−0.13375 (2)	0.168903 (19)	−0.629545 (15)	0.011
C(5)	0.03794 (3)	0.17149 (2)	−0.554346 (17)	0.013
C(6)	0.06003 (3)	0.26527 (2)	−0.459365 (17)	0.012
C(7)	−0.17855 (2)	0.514823 (18)	−0.280347 (14)	0.011
C(8)	−0.09268	0.60231	−0.17602	0.016
H(1)	−0.3745	0.4295	−0.501	0.028
H(2)	−0.4106	0.2643	−0.6694	0.031
H(3)	0.1516	0.0988	−0.569	0.032
H(4)	0.1892	0.2646	−0.4015	0.031
H(5)	−0.0438	0.0379	−0.7435	0.026
H(6)	0.0882	0.4585	−0.3054	0.028
H(7)	−0.17468	0.58757	−0.10693	0.038
H(8)	0.05413	0.57829	−0.15374	0.038
H(9)	−0.10382	0.71426	−0.19783	0.039

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01008 (7)	0.01796 (8)	0.01469 (8)	0.00077 (5)	0.00005 (6)	−0.00585 (7)
O(2)	0.00959 (7)	0.02308 (9)	0.01461 (8)	0.00192 (6)	0.00349 (6)	−0.00111 (8)
N(1)	0.00845 (6)	0.01261 (6)	0.01069 (6)	0.00051 (5)	0.00144 (5)	−0.00152 (5)
C(1)	0.00796 (5)	0.01069 (6)	0.00943 (6)	0.00089 (4)	0.00089 (4)	0.00017 (5)
C(2)	0.00830 (6)	0.01284 (6)	0.01121 (6)	0.00207 (4)	0.00023 (5)	−0.00052 (5)
C(3)	0.00847 (6)	0.01398 (6)	0.01137 (6)	0.00150 (5)	−0.00033 (5)	−0.00098 (5)
C(4)	0.00866 (6)	0.01216 (6)	0.01070 (6)	0.00058 (4)	0.00039 (5)	−0.00111 (5)
C(5)	0.00931 (6)	0.01485 (7)	0.01339 (7)	0.00316 (5)	−0.00077 (5)	−0.00322 (6)
C(6)	0.00897 (6)	0.01459 (7)	0.01223 (6)	0.00294 (5)	−0.00102 (5)	−0.00264 (5)
C(7)	0.00996 (6)	0.01224 (6)	0.01101 (6)	0.00083 (4)	0.00271 (4)	0.00003 (5)
C(8)	0.01705	0.01597	0.01466	−0.00114	0.00405	−0.00446
H(1)	0.019896	0.033928	0.029873	0.012322	0.00102	−0.006
H(2)	0.017879	0.044741	0.027643	0.007036	−0.007724	−0.008856
H(3)	0.022443	0.036371	0.035067	0.014387	−0.001873	−0.012308
H(4)	0.018413	0.042682	0.029905	0.008791	−0.008879	−0.011359
H(5)	0.018782	0.031821	0.028553	0.003628	0.002377	−0.009856
H(6)	0.015038	0.037498	0.029209	0.000258	−0.000677	−0.010966
H(7)	0.0384	0.0515	0.026653	−0.009049	0.01588	−0.007924
H(8)	0.02209	0.050884	0.039922	0.005281	−0.001232	−0.01538
H(9)	0.054321	0.023014	0.037554	−0.000395	0.003514	−0.002648

Geometric parameters (Å, º)

O(1)—C(4)	1.3641 (3)	C(3)—C(4)	1.3919 (2)
O(1)—H(5)	0.9818 (2)	C(3)—H(2)	1.0716 (2)
O(2)—C(7)	1.2374 (3)	C(4)—C(5)	1.3941 (2)
N(1)—C(1)	1.4120 (3)	C(5)—C(6)	1.3877 (3)
N(1)—C(7)	1.3434 (2)	C(5)—H(3)	1.0760 (2)
N(1)—H(6)	1.0187 (2)	C(6)—H(4)	1.0564 (2)
C(1)—C(2)	1.3944 (2)	C(7)—C(8)	1.5065 (2)
C(1)—C(6)	1.3951 (2)	C(8)—H(7)	1.0593
C(2)—C(3)	1.3922 (2)	C(8)—H(8)	1.0587
C(2)—H(1)	1.0853 (2)	C(8)—H(9)	1.0578
C(4)—O(1)—H(5)	111.81 (2)	C(4)—C(5)—C(6)	119.910 (17)
C(1)—N(1)—C(7)	128.257 (17)	C(4)—C(5)—H(3)	119.820 (17)
C(1)—N(1)—H(6)	114.969 (17)	C(6)—C(5)—H(3)	120.252 (17)
C(7)—N(1)—H(6)	116.537 (18)	C(1)—C(6)—C(5)	120.685 (17)
N(1)—C(1)—C(2)	124.109 (16)	C(1)—C(6)—H(4)	119.823 (17)
N(1)—C(1)—C(6)	116.496 (16)	C(5)—C(6)—H(4)	119.473 (17)
C(2)—C(1)—C(6)	119.377 (16)	O(2)—C(7)—N(1)	123.40 (2)
C(1)—C(2)—C(3)	119.881 (16)	O(2)—C(7)—C(8)	121.546 (17)
C(1)—C(2)—H(1)	120.727 (17)	N(1)—C(7)—C(8)	115.052 (14)
C(3)—C(2)—H(1)	119.389 (16)	C(7)—C(8)—H(7)	109.548 (6)
C(2)—C(3)—C(4)	120.572 (16)	C(7)—C(8)—H(8)	111.011 (6)
C(2)—C(3)—H(2)	119.601 (17)	C(7)—C(8)—H(9)	108.497 (6)
C(4)—C(3)—H(2)	119.813 (17)	H(7)—C(8)—H(8)	114.2493
O(1)—C(4)—C(3)	118.359 (17)	H(7)—C(8)—H(9)	105.8704
O(1)—C(4)—C(5)	122.094 (18)	H(8)—C(8)—H(9)	107.3736
C(3)—C(4)—C(5)	119.546 (17)

(M_IM)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	364 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.017	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.016	(Δ/σ)max < 0.001
S = 2.05	Δρmax = 0.26 e Å^−3
6706 reflections	Δρmin = −0.20 e Å^−3

Special details

Refinement. Multipolar refinement was performed on F with the program XDLSM against high resolution data, except four atoms: C8, H7, H8, H9. Hydrogen atom positions were taken from 80 K neutron diffraction data (Wilson, 1997), except the H7, H8, H9 atom positions. This were obtained by elongating the bond length along the vector of the atom they are attached to and their neutron positions. Anisotropic ADPs for hydrogen atoms were generated by the SHADE program. Pseudoatoms paramiters for the C8, H7, H8, H9 atoms were taken from the invariom database.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16402 (3)	0.07618 (3)	−0.72239 (2)	0.014
O(2)	−0.35334 (3)	0.50639 (3)	−0.30856 (2)	0.016
N(1)	−0.05183 (3)	0.44910 (2)	−0.339476 (17)	0.011
C(1)	−0.08803 (2)	0.357586 (18)	−0.438130 (15)	0.009
C(2)	−0.25817 (2)	0.357375 (19)	−0.514887 (15)	0.011
C(3)	−0.28044 (2)	0.26287 (2)	−0.609902 (16)	0.011
C(4)	−0.13374 (2)	0.168902 (19)	−0.629552 (15)	0.011
C(5)	0.03795 (3)	0.17149 (2)	−0.554347 (17)	0.013
C(6)	0.06003 (3)	0.26527 (2)	−0.459364 (16)	0.012
C(7)	−0.17855 (2)	0.514834 (17)	−0.280336 (14)	0.011
C(8)	−0.09268	0.60231	−0.17602	0.016
H(1)	−0.3745	0.4295	−0.501	0.028
H(2)	−0.4106	0.2643	−0.6694	0.031
H(3)	0.1516	0.0988	−0.569	0.032
H(4)	0.1892	0.2646	−0.4015	0.031
H(5)	−0.0438	0.0379	−0.7435	0.026
H(6)	0.0882	0.4585	−0.3054	0.028
H(7)	−0.177138	0.587087	−0.104835	0.037
H(8)	0.058636	0.577432	−0.153052	0.038
H(9)	−0.10417	0.717814	−0.198529	0.038

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01008 (7)	0.01796 (8)	0.01467 (8)	0.00079 (5)	0.00006 (6)	−0.00585 (7)
O(2)	0.00957 (7)	0.02306 (9)	0.01462 (8)	0.00192 (6)	0.00351 (6)	−0.00113 (8)
N(1)	0.00845 (6)	0.01259 (6)	0.01069 (6)	0.00052 (5)	0.00143 (5)	−0.00152 (5)
C(1)	0.00795 (5)	0.01070 (6)	0.00942 (6)	0.00089 (4)	0.00087 (4)	0.00019 (5)
C(2)	0.00830 (6)	0.01285 (6)	0.01119 (6)	0.00206 (4)	0.00023 (5)	−0.00051 (5)
C(3)	0.00844 (5)	0.01399 (6)	0.01140 (6)	0.00149 (4)	−0.00031 (5)	−0.00100 (5)
C(4)	0.00865 (6)	0.01215 (6)	0.01072 (6)	0.00057 (4)	0.00040 (5)	−0.00112 (5)
C(5)	0.00930 (6)	0.01486 (7)	0.01337 (7)	0.00315 (5)	−0.00078 (5)	−0.00323 (5)
C(6)	0.00897 (6)	0.01457 (6)	0.01225 (6)	0.00293 (5)	−0.00104 (5)	−0.00265 (5)
C(7)	0.00996 (5)	0.01223 (6)	0.01103 (6)	0.00084 (4)	0.00273 (4)	0.00007 (5)
C(8)	0.01705	0.01597	0.01466	−0.00114	0.00405	−0.00446
H(1)	0.019896	0.033928	0.029873	0.012322	0.00102	−0.006
H(2)	0.017879	0.044741	0.027643	0.007036	−0.007724	−0.008856
H(3)	0.022443	0.036371	0.035067	0.014387	−0.001873	−0.012308
H(4)	0.018413	0.042682	0.029905	0.008791	−0.008879	−0.011359
H(5)	0.018782	0.031821	0.028553	0.003628	0.002377	−0.009856
H(6)	0.015038	0.037498	0.029209	0.000258	−0.000677	−0.010966
H(7)	0.037933	0.050554	0.026026	−0.009017	0.01562	−0.007783
H(8)	0.021525	0.050832	0.039604	0.005464	−0.001589	−0.015658
H(9)	0.053331	0.022368	0.037228	−0.000745	0.003544	−0.002732

Geometric parameters (Å, º)

O(1)—C(4)	1.3641 (3)	C(3)—C(4)	1.3919 (2)
O(1)—H(5)	0.9818 (2)	C(3)—H(2)	1.0717 (2)
O(2)—C(7)	1.2376 (3)	C(4)—C(5)	1.3942 (2)
N(1)—C(1)	1.4120 (2)	C(5)—C(6)	1.3877 (2)
N(1)—C(7)	1.3436 (2)	C(5)—H(3)	1.0760 (2)
N(1)—H(6)	1.0186 (2)	C(6)—H(4)	1.0564 (2)
C(1)—C(2)	1.3946 (2)	C(7)—C(8)	1.5064 (2)
C(1)—C(6)	1.3951 (2)	C(8)—H(7)	1.0913
C(2)—C(3)	1.3922 (2)	C(8)—H(8)	1.0914
C(2)—H(1)	1.0852 (2)	C(8)—H(9)	1.0914
C(4)—O(1)—H(5)	111.80 (2)	C(4)—C(5)—C(6)	119.913 (17)
C(1)—N(1)—C(7)	128.257 (17)	C(4)—C(5)—H(3)	119.817 (17)
C(1)—N(1)—H(6)	114.972 (17)	C(6)—C(5)—H(3)	120.252 (17)
C(7)—N(1)—H(6)	116.534 (18)	C(1)—C(6)—C(5)	120.688 (16)
N(1)—C(1)—C(2)	124.109 (16)	C(1)—C(6)—H(4)	119.820 (17)
N(1)—C(1)—C(6)	116.499 (16)	C(5)—C(6)—H(4)	119.474 (17)
C(2)—C(1)—C(6)	119.375 (16)	O(2)—C(7)—N(1)	123.39 (2)
C(1)—C(2)—C(3)	119.876 (16)	O(2)—C(7)—C(8)	121.556 (17)
C(1)—C(2)—H(1)	120.724 (16)	N(1)—C(7)—C(8)	115.050 (14)
C(3)—C(2)—H(1)	119.397 (16)	C(7)—C(8)—H(7)	109.540 (6)
C(2)—C(3)—C(4)	120.579 (16)	C(7)—C(8)—H(8)	110.979 (6)
C(2)—C(3)—H(2)	119.598 (16)	C(7)—C(8)—H(9)	108.493 (6)
C(4)—C(3)—H(2)	119.809 (17)	H(7)—C(8)—H(8)	114.2204
O(1)—C(4)—C(3)	118.358 (17)	H(7)—C(8)—H(9)	105.8938
O(1)—C(4)—C(5)	122.102 (18)	H(8)—C(8)—H(9)	107.4284
C(3)—C(4)—C(5)	119.540 (17)

(Mkrmm)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	415 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.015	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.015	(Δ/σ)max < 0.001
S = 1.86	Δρmax = 0.14 e Å^−3
6706 reflections	Δρmin = −0.14 e Å^−3

Special details

Refinement. KRMM Multipolar refinement was performed on F with the program XDLSM against high resolution data. Hydrogen atom positions were taken from 80 K neutron diffraction data (Wilson, 1997), except the H7, H8, H9 atom positions. This were obtained by elongating the bond length along the vector of the atom they are attached to and their neutron positions. Anisotropic ADPs for hydrogen atoms were generated by the SHADE program.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16391 (3)	0.07617 (3)	−0.72231 (2)	0.014
O(2)	−0.35321 (4)	0.50644 (3)	−0.30854 (2)	0.016
N(1)	−0.05183 (2)	0.449094 (19)	−0.339484 (16)	0.011
C(1)	−0.08803 (2)	0.357584 (16)	−0.438136 (13)	0.009
C(2)	−0.25816 (2)	0.357376 (18)	−0.514883 (14)	0.011
C(3)	−0.28045 (2)	0.262862 (18)	−0.609911 (15)	0.012
C(4)	−0.13374 (2)	0.168903 (17)	−0.629551 (14)	0.011
C(5)	0.03795 (2)	0.171477 (19)	−0.554346 (15)	0.013
C(6)	0.06004 (2)	0.265278 (19)	−0.459362 (15)	0.012
C(7)	−0.17854 (2)	0.514817 (17)	−0.280339 (14)	0.011
C(8)	−0.09275 (3)	0.60224 (2)	−0.176068 (18)	0.016
H(1)	−0.3745	0.4295	−0.501	0.028
H(2)	−0.4106	0.2643	−0.6694	0.031
H(3)	0.1516	0.0988	−0.569	0.032
H(4)	0.1892	0.2646	−0.4015	0.031
H(5)	−0.0438	0.0379	−0.7435	0.026
H(6)	0.0882	0.4585	−0.3054	0.028
H(7)	−0.17468	0.58757	−0.10693	0.038
H(8)	0.05413	0.57829	−0.15374	0.038
H(9)	−0.10382	0.71426	−0.19783	0.039

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01019 (7)	0.01799 (9)	0.01472 (9)	0.00077 (6)	0.00006 (6)	−0.00572 (7)
O(2)	0.00972 (7)	0.02324 (10)	0.01459 (9)	0.00189 (7)	0.00354 (6)	−0.00134 (8)
N(1)	0.00861 (5)	0.01265 (6)	0.01077 (6)	0.00053 (4)	0.00146 (4)	−0.00150 (5)
C(1)	0.00812 (5)	0.01078 (5)	0.00952 (5)	0.00089 (4)	0.00095 (4)	0.00020 (4)
C(2)	0.00847 (5)	0.01296 (6)	0.01129 (6)	0.00204 (4)	0.00027 (4)	−0.00052 (5)
C(3)	0.00858 (5)	0.01410 (6)	0.01151 (6)	0.00148 (4)	−0.00029 (4)	−0.00098 (5)
C(4)	0.00880 (5)	0.01225 (6)	0.01084 (6)	0.00056 (4)	0.00040 (4)	−0.00109 (4)
C(5)	0.00947 (6)	0.01493 (6)	0.01352 (6)	0.00315 (4)	−0.00072 (5)	−0.00320 (5)
C(6)	0.00909 (5)	0.01475 (6)	0.01234 (6)	0.00291 (4)	−0.00102 (4)	−0.00264 (5)
C(7)	0.01013 (5)	0.01229 (5)	0.01114 (6)	0.00085 (4)	0.00276 (4)	0.00000 (4)
C(8)	0.01737 (7)	0.01637 (7)	0.01496 (7)	−0.00114 (5)	0.00415 (6)	−0.00444 (6)
H(1)	0.019896	0.033928	0.029873	0.012322	0.00102	−0.006
H(2)	0.017879	0.044741	0.027643	0.007036	−0.007724	−0.008856
H(3)	0.022443	0.036371	0.035067	0.014387	−0.001873	−0.012308
H(4)	0.018413	0.042682	0.029905	0.008791	−0.008879	−0.011359
H(5)	0.018782	0.031821	0.028553	0.003628	0.002377	−0.009856
H(6)	0.015038	0.037498	0.029209	0.000258	−0.000677	−0.010966
H(7)	0.0384	0.0515	0.026653	−0.009049	0.01588	−0.007924
H(8)	0.02209	0.050884	0.039922	0.005281	−0.001232	−0.01538
H(9)	0.054321	0.023014	0.037554	−0.000395	0.003514	−0.002648

Geometric parameters (Å, º)

O(1)—C(4)	1.3634 (3)	C(3)—C(4)	1.3919 (2)
O(1)—H(5)	0.9814 (2)	C(3)—H(2)	1.0716 (2)
O(2)—C(7)	1.2367 (3)	C(4)—C(5)	1.3942 (2)
N(1)—C(1)	1.4119 (2)	C(5)—C(6)	1.3878 (2)
N(1)—C(7)	1.3435 (2)	C(5)—H(3)	1.0759 (2)
N(1)—H(6)	1.0186 (2)	C(6)—H(4)	1.0563 (2)
C(1)—C(2)	1.3944 (2)	C(7)—C(8)	1.5056 (2)
C(1)—C(6)	1.3951 (2)	C(8)—H(7)	1.0594 (2)
C(2)—C(3)	1.3923 (2)	C(8)—H(8)	1.0591 (2)
C(2)—H(1)	1.0853 (2)	C(8)—H(9)	1.0583 (2)
C(4)—O(1)—H(5)	111.88 (2)	C(4)—C(5)—C(6)	119.909 (15)
C(1)—N(1)—C(7)	128.258 (16)	C(4)—C(5)—H(3)	119.821 (16)
C(1)—N(1)—H(6)	114.976 (15)	C(6)—C(5)—H(3)	120.252 (15)
C(7)—N(1)—H(6)	116.528 (17)	C(1)—C(6)—C(5)	120.681 (15)
N(1)—C(1)—C(2)	124.106 (14)	C(1)—C(6)—H(4)	119.829 (15)
N(1)—C(1)—C(6)	116.492 (14)	C(5)—C(6)—H(4)	119.472 (15)
C(2)—C(1)—C(6)	119.384 (15)	O(2)—C(7)—N(1)	123.41 (2)
C(1)—C(2)—C(3)	119.879 (15)	O(2)—C(7)—C(8)	121.53 (2)
C(1)—C(2)—H(1)	120.731 (15)	N(1)—C(7)—C(8)	115.063 (15)
C(3)—C(2)—H(1)	119.387 (14)	C(7)—C(8)—H(7)	109.608 (17)
C(2)—C(3)—C(4)	120.568 (15)	C(7)—C(8)—H(8)	111.049 (16)
C(2)—C(3)—H(2)	119.599 (15)	C(7)—C(8)—H(9)	108.536 (17)
C(4)—C(3)—H(2)	119.819 (15)	H(7)—C(8)—H(8)	114.21 (2)
O(1)—C(4)—C(3)	118.385 (16)	H(7)—C(8)—H(9)	105.834 (18)
O(1)—C(4)—C(5)	122.064 (17)	H(8)—C(8)—H(9)	107.309 (18)
C(3)—C(4)—C(5)	119.549 (15)

(M)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	415 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.015	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.015	(Δ/σ)max < 0.001
S = 1.86	Δρmax = 0.13 e Å^−3
6706 reflections	Δρmin = −0.12 e Å^−3

Special details

Refinement. Multipolar refinement was performed on F with the program XDLSM against high resolution data. Hydrogen atom positions were taken from 80 K neutron diffraction data (Wilson, 1997), except the H7, H8, H9 atom positions. This were obtained by elongating the bond length along the vector of the atom they are attached to and their neutron positions. Anisotropic ADPs for hydrogen atoms were generated by the SHADE program.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16402 (3)	0.07618 (2)	−0.722379 (19)	0.014
O(2)	−0.35333 (3)	0.50640 (3)	−0.308567 (19)	0.016
N(1)	−0.05183 (2)	0.449101 (18)	−0.339479 (15)	0.011
C(1)	−0.08804 (2)	0.357595 (17)	−0.438129 (14)	0.009
C(2)	−0.25816 (2)	0.357365 (18)	−0.514892 (14)	0.011
C(3)	−0.28044 (2)	0.262864 (18)	−0.609899 (14)	0.012
C(4)	−0.13375 (2)	0.168902 (17)	−0.629551 (14)	0.011
C(5)	0.03794 (2)	0.171493 (19)	−0.554343 (15)	0.013
C(6)	0.06004 (2)	0.265268 (18)	−0.459372 (15)	0.012
C(7)	−0.17849 (2)	0.514825 (18)	−0.280331 (14)	0.011
C(8)	−0.09275 (3)	0.60222 (2)	−0.176047 (16)	0.016
H(1)	−0.3745	0.4295	−0.501	0.028
H(2)	−0.4106	0.2643	−0.6694	0.031
H(3)	0.1516	0.0988	−0.569	0.032
H(4)	0.1892	0.2646	−0.4015	0.031
H(5)	−0.0438	0.0379	−0.7435	0.026
H(6)	0.0882	0.4585	−0.3054	0.028
H(7)	−0.174634	0.587538	−0.106946	0.037
H(8)	0.054143	0.578171	−0.153734	0.038
H(9)	−0.103829	0.714385	−0.197861	0.038

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01013 (6)	0.01803 (8)	0.01473 (7)	0.00080 (5)	0.00006 (5)	−0.00585 (6)
O(2)	0.00967 (6)	0.02314 (9)	0.01462 (7)	0.00190 (6)	0.00349 (5)	−0.00114 (7)
N(1)	0.00856 (5)	0.01266 (6)	0.01076 (6)	0.00053 (4)	0.00144 (4)	−0.00151 (4)
C(1)	0.00806 (5)	0.01079 (5)	0.00953 (6)	0.00092 (4)	0.00091 (4)	0.00017 (4)
C(2)	0.00842 (5)	0.01296 (6)	0.01130 (6)	0.00206 (4)	0.00026 (4)	−0.00052 (5)
C(3)	0.00855 (5)	0.01410 (6)	0.01149 (6)	0.00150 (4)	−0.00030 (4)	−0.00099 (5)
C(4)	0.00878 (5)	0.01222 (6)	0.01085 (6)	0.00059 (4)	0.00040 (4)	−0.00111 (4)
C(5)	0.00945 (6)	0.01492 (6)	0.01349 (6)	0.00317 (4)	−0.00075 (5)	−0.00321 (5)
C(6)	0.00907 (5)	0.01471 (6)	0.01235 (6)	0.00294 (4)	−0.00101 (4)	−0.00264 (5)
C(7)	0.01005 (6)	0.01233 (6)	0.01116 (6)	0.00085 (4)	0.00274 (4)	−0.00007 (5)
C(8)	0.01731 (7)	0.01637 (7)	0.01491 (7)	−0.00112 (5)	0.00412 (5)	−0.00442 (5)
H(1)	0.019896	0.033928	0.029873	0.012322	0.00102	−0.006
H(2)	0.017879	0.044741	0.027643	0.007036	−0.007724	−0.008856
H(3)	0.022443	0.036371	0.035067	0.014387	−0.001873	−0.012308
H(4)	0.018413	0.042682	0.029905	0.008791	−0.008879	−0.011359
H(5)	0.018782	0.031821	0.028553	0.003628	0.002377	−0.009856
H(6)	0.015038	0.037498	0.029209	0.000258	−0.000677	−0.010966
H(7)	0.037933	0.050554	0.026026	−0.009017	0.01562	−0.007783
H(8)	0.021525	0.050832	0.039604	0.005464	−0.001589	−0.015658
H(9)	0.053331	0.022368	0.037228	−0.000745	0.003544	−0.002732

Geometric parameters (Å, º)

O(1)—C(4)	1.3640 (2)	C(3)—C(4)	1.3918 (2)
O(1)—H(5)	0.9819 (2)	C(3)—H(2)	1.0717 (2)
O(2)—C(7)	1.2379 (3)	C(4)—C(5)	1.3942 (2)
N(1)—C(1)	1.4119 (2)	C(5)—C(6)	1.3876 (2)
N(1)—C(7)	1.3433 (2)	C(5)—H(3)	1.0761 (2)
N(1)—H(6)	1.0186 (2)	C(6)—H(4)	1.0563 (2)
C(1)—C(2)	1.3945 (2)	C(7)—C(8)	1.5054 (2)
C(1)—C(6)	1.3953 (2)	C(8)—H(7)	1.0588 (2)
C(2)—C(3)	1.3920 (2)	C(8)—H(8)	1.0594 (2)
C(2)—H(1)	1.0853 (2)	C(8)—H(9)	1.0597 (2)
C(4)—O(1)—H(5)	111.807 (18)	C(4)—C(5)—C(6)	119.920 (15)
C(1)—N(1)—C(7)	128.265 (16)	C(4)—C(5)—H(3)	119.813 (16)
C(1)—N(1)—H(6)	114.975 (15)	C(6)—C(5)—H(3)	120.250 (15)
C(7)—N(1)—H(6)	116.522 (16)	C(1)—C(6)—C(5)	120.683 (15)
N(1)—C(1)—C(2)	124.120 (15)	C(1)—C(6)—H(4)	119.814 (16)
N(1)—C(1)—C(6)	116.496 (14)	C(5)—C(6)—H(4)	119.484 (15)
C(2)—C(1)—C(6)	119.365 (15)	O(2)—C(7)—N(1)	123.385 (19)
C(1)—C(2)—C(3)	119.886 (15)	O(2)—C(7)—C(8)	121.530 (18)
C(1)—C(2)—H(1)	120.713 (15)	N(1)—C(7)—C(8)	115.083 (15)
C(3)—C(2)—H(1)	119.399 (14)	C(7)—C(8)—H(7)	109.618 (15)
C(2)—C(3)—C(4)	120.580 (15)	C(7)—C(8)—H(8)	111.002 (15)
C(2)—C(3)—H(2)	119.598 (15)	C(7)—C(8)—H(9)	108.514 (16)
C(4)—C(3)—H(2)	119.808 (15)	H(7)—C(8)—H(8)	114.207 (17)
O(1)—C(4)—C(3)	118.360 (16)	H(7)—C(8)—H(9)	105.856 (15)
O(1)—C(4)—C(5)	122.103 (16)	H(8)—C(8)—H(9)	107.352 (16)
C(3)—C(4)—C(5)	119.537 (15)

(X-ray)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F	408 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.016	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.015	(Δ/σ)max < 0.001
S = 1.93	Δρmax = 0.14 e Å^−3
6706 reflections	Δρmin = −0.13 e Å^−3

Special details

Refinement. Multipolar refinement was performed on F with the program XDLSM against high resolution data. Hydrogen atom positions were taken from 80 K neutron diffraction data (Wilson, 1997), except the H7, H8, H9 atom positions. This were obtained by elongating the bond length along the vector of the atom they are attached to and their neutron positions.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16403 (3)	0.07616 (2)	0.277579 (17)	0.014
O(2)	−0.35339 (3)	0.50639 (3)	0.691419 (18)	0.015
N(1)	−0.05180 (2)	0.449110 (18)	0.660530 (15)	0.01
C(1)	−0.08804 (2)	0.357603 (18)	0.561879 (15)	0.009
C(2)	−0.25817 (2)	0.357389 (18)	0.485112 (14)	0.011
C(3)	−0.28046 (2)	0.262864 (19)	0.390093 (15)	0.011
C(4)	−0.13375 (2)	0.168881 (19)	0.370437 (15)	0.01
C(5)	0.03798 (2)	0.171491 (19)	0.445665 (16)	0.013
C(6)	0.06007 (2)	0.265269 (19)	0.540645 (15)	0.012
C(7)	−0.17848 (3)	0.514833 (19)	0.719666 (16)	0.011
C(8)	−0.09271 (3)	0.60224 (2)	0.823984 (16)	0.016
H(1)	−0.371699	0.431607	0.499404	0.026228
H(2)	−0.414245	0.263555	0.332046	0.026004
H(3)	0.154325	0.10002	0.431333	0.028745
H(4)	0.19207	0.267292	0.600344	0.032903
H(5)	−0.046407	0.038489	0.256071	0.037562
H(6)	0.08683	0.460953	0.693686	0.025268
H(7)	−0.108077	0.714889	0.804972	0.044645
H(8)	0.054212	0.579318	0.847486	0.048969
H(9)	−0.170045	0.579273	0.893944	0.040001

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01002 (6)	0.01782 (7)	0.01449 (7)	0.00077 (5)	−0.00001 (5)	−0.00584 (6)
O(2)	0.00949 (6)	0.02297 (8)	0.01451 (7)	0.00190 (5)	0.00346 (5)	−0.00105 (7)
N(1)	0.00842 (5)	0.01247 (5)	0.01056 (5)	0.00056 (4)	0.00144 (4)	−0.00150 (5)
C(1)	0.00784 (5)	0.01058 (5)	0.00934 (6)	0.00095 (4)	0.00088 (4)	0.00015 (5)
C(2)	0.00819 (5)	0.01277 (6)	0.01105 (6)	0.00201 (4)	0.00021 (4)	−0.00052 (5)
C(3)	0.00835 (5)	0.01389 (6)	0.01127 (6)	0.00152 (4)	−0.00029 (4)	−0.00099 (5)
C(4)	0.00854 (5)	0.01200 (6)	0.01066 (6)	0.00061 (4)	0.00036 (4)	−0.00114 (5)
C(5)	0.00926 (5)	0.01469 (6)	0.01324 (6)	0.00314 (4)	−0.00081 (5)	−0.00318 (5)
C(6)	0.00889 (5)	0.01447 (6)	0.01212 (6)	0.00296 (4)	−0.00096 (4)	−0.00264 (5)
C(7)	0.00981 (6)	0.01214 (6)	0.01095 (6)	0.00085 (4)	0.00269 (5)	−0.00012 (5)
C(8)	0.01710 (7)	0.01620 (7)	0.01463 (6)	−0.00116 (5)	0.00407 (5)	−0.00452 (5)

Geometric parameters (Å, º)

O(1)—C(4)	1.3642 (2)	C(3)—C(4)	1.3921 (2)
O(1)—H(5)	0.9650 (2)	C(3)—H(2)	1.0830 (2)
O(2)—C(7)	1.2385 (2)	C(4)—C(5)	1.3945 (2)
N(1)—C(1)	1.4119 (2)	C(5)—C(6)	1.3877 (2)
N(1)—C(7)	1.3433 (2)	C(5)—H(3)	1.0830 (2)
N(1)—H(6)	1.0090 (2)	C(6)—H(4)	1.0830 (2)
C(1)—C(2)	1.3946 (2)	C(7)—C(8)	1.5058 (2)
C(1)—C(6)	1.3955 (2)	C(8)—H(7)	1.0590 (2)
C(2)—C(3)	1.3923 (2)	C(8)—H(8)	1.0590 (2)
C(2)—H(1)	1.0830 (2)	C(8)—H(9)	1.0590 (2)
C(4)—O(1)—H(5)	112.263 (18)	C(4)—C(5)—C(6)	119.926 (16)
C(1)—N(1)—C(7)	128.253 (16)	C(4)—C(5)—H(3)	120.640 (16)
C(1)—N(1)—H(6)	115.504 (15)	C(6)—C(5)—H(3)	119.431 (15)
C(7)—N(1)—H(6)	116.107 (16)	C(1)—C(6)—C(5)	120.678 (16)
N(1)—C(1)—C(2)	124.123 (15)	C(1)—C(6)—H(4)	118.694 (16)
N(1)—C(1)—C(6)	116.483 (15)	C(5)—C(6)—H(4)	120.624 (15)
C(2)—C(1)—C(6)	119.376 (16)	O(2)—C(7)—N(1)	123.386 (19)
C(1)—C(2)—C(3)	119.883 (15)	O(2)—C(7)—C(8)	121.535 (18)
C(1)—C(2)—H(1)	119.697 (16)	N(1)—C(7)—C(8)	115.077 (16)
C(3)—C(2)—H(1)	120.418 (15)	C(7)—C(8)—H(7)	109.534 (16)
C(2)—C(3)—C(4)	120.580 (15)	C(7)—C(8)—H(8)	111.934 (15)
C(2)—C(3)—H(2)	118.736 (15)	C(7)—C(8)—H(9)	108.267 (15)
C(4)—C(3)—H(2)	120.684 (16)	H(7)—C(8)—H(8)	108.436 (16)
O(1)—C(4)—C(3)	118.357 (16)	H(7)—C(8)—H(9)	107.689 (16)
O(1)—C(4)—C(5)	122.113 (17)	H(8)—C(8)—H(9)	110.887 (17)
C(3)—C(4)—C(5)	119.529 (16)

(IAM)

Crystal data

?	Z = ?
Mr = ?	F(000) = 320
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 7.077 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.173 (2) Å	µ = 0.10 mm^−1
c = 11.574 (4) Å	T = 85 K
β = 97.90 (2)°	, colourless
V = 744.2 (4) Å^3	0.15 × 0.1 × 0.1 mm

Data collection

CCD area detector diffractometer	8661 independent reflections
Radiation source: TXS rotating anode	6967 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.022
ω scans	θmax = 52.4°, θmin = 2.8°
Absorption correction: multi-scan Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.	h = −14→15
Tmin = 0.921, Tmax = 1	k = −20→19
46012 measured reflections	l = −25→19

Refinement

Refinement on F^2	127 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.031	w2 = q/[s^2(Fo^2) + (0.06 P)^2 + 0.39 P + 0.00 + 0.00 sin(th)] where P = (0.0000 Fo^2 + 1.0000 Fc^2) q = 1.0
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 4.97	Δρmax = 0.63 e Å^−3
6706 reflections	Δρmin = −0.21 e Å^−3

Special details

Refinement. Refinement was performed on F with the program XDLSM against high resolution data. Positions and anisotropic ADPs of non hydrogen atoms and positions and isotropic ADPs of hydrogen atoms were refined. weighting shame from the SHELX program used.

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

	x	y	z	Uiso*/Ueq
O(1)	−0.16417 (4)	0.07622 (4)	0.27756 (3)	0.016
O(2)	−0.35340 (4)	0.50625 (4)	0.69140 (3)	0.018
N(1)	−0.05187 (4)	0.44914 (3)	0.66054 (3)	0.012
C(1)	−0.08803 (4)	0.35756 (4)	0.56185 (3)	0.011
C(3)	−0.28040 (5)	0.26292 (4)	0.39014 (3)	0.013
C(2)	−0.25816 (5)	0.35732 (4)	0.48509 (3)	0.013
C(4)	−0.13376 (5)	0.16893 (4)	0.37049 (3)	0.012
C(6)	0.06000 (5)	0.26520 (4)	0.54062 (3)	0.014
C(5)	0.03794 (5)	0.17151 (4)	0.44568 (3)	0.015
C(7)	−0.17861 (5)	0.51484 (4)	0.71969 (3)	0.013
C(8)	−0.09267 (6)	0.60219 (5)	0.82396 (4)	0.018
H(1)	−0.3560 (15)	0.4236 (12)	0.4991 (10)	0.007995
H(2)	−0.4017 (15)	0.2653 (12)	0.3364 (10)	0.006156
H(6)	0.0714 (15)	0.4593 (12)	0.6896 (9)	0.004315
H(4)	0.1760 (17)	0.2644 (13)	0.5952 (10)	0.010803
H(3)	0.1416 (14)	0.1068 (11)	0.4319 (9)	0.002923
H(5)	−0.0536 (17)	0.0418 (13)	0.2590 (10)	0.010598
H(9)	−0.1641 (16)	0.5854 (13)	0.8875 (10)	0.010267
H(8)	0.0379 (19)	0.5793 (15)	0.8451 (12)	0.021464
H(7)	−0.1062 (17)	0.7052 (14)	0.8080 (11)	0.015399

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01040 (9)	0.01872 (11)	0.01508 (10)	0.00083 (8)	−0.00002 (7)	−0.00632 (8)
O(2)	0.00975 (9)	0.02367 (13)	0.01530 (10)	0.00194 (8)	0.00340 (7)	−0.00065 (9)
N(1)	0.00882 (8)	0.01312 (10)	0.01111 (9)	0.00055 (7)	0.00137 (7)	−0.00147 (7)
C(1)	0.00861 (9)	0.01100 (10)	0.00989 (9)	0.00076 (7)	0.00111 (7)	0.00047 (8)
C(3)	0.00898 (10)	0.01444 (11)	0.01187 (11)	0.00130 (8)	−0.00009 (8)	−0.00061 (9)
C(2)	0.00891 (9)	0.01334 (11)	0.01165 (10)	0.00194 (8)	0.00052 (8)	−0.00015 (8)
C(4)	0.00929 (9)	0.01257 (11)	0.01114 (10)	0.00023 (8)	0.00055 (7)	−0.00091 (8)
C(6)	0.00952 (10)	0.01496 (12)	0.01279 (11)	0.00281 (8)	−0.00085 (8)	−0.00230 (9)
C(5)	0.00984 (10)	0.01525 (12)	0.01393 (11)	0.00300 (9)	−0.00059 (8)	−0.00284 (9)
C(7)	0.01083 (10)	0.01239 (10)	0.01142 (10)	0.00090 (8)	0.00291 (8)	0.00043 (8)
C(8)	0.01749 (14)	0.01713 (14)	0.01533 (13)	−0.00119 (11)	0.00402 (10)	−0.00454 (11)

Geometric parameters (Å, º)

O(1)—C(4)	1.3665 (4)	C(3)—H(2)	0.990 (11)
O(1)—H(5)	0.898 (12)	C(2)—H(1)	0.953 (11)
O(2)—C(7)	1.2392 (5)	C(4)—C(5)	1.3954 (5)
N(1)—C(1)	1.4142 (4)	C(6)—C(5)	1.3885 (5)
N(1)—C(7)	1.3451 (4)	C(6)—H(4)	0.965 (12)
N(1)—H(6)	0.897 (11)	C(5)—H(3)	0.975 (10)
C(1)—C(2)	1.3957 (4)	C(7)—C(8)	1.5071 (5)
C(1)—C(6)	1.3974 (5)	C(8)—H(9)	0.961 (12)
C(3)—C(2)	1.3926 (5)	C(8)—H(8)	0.948 (13)
C(3)—C(4)	1.3940 (5)	C(8)—H(7)	0.967 (13)
C(4)—O(1)—H(5)	111.1 (7)	C(1)—C(6)—C(5)	120.72 (3)
C(1)—N(1)—C(7)	128.26 (3)	C(1)—C(6)—H(4)	118.8 (7)
C(1)—N(1)—H(6)	115.1 (7)	C(5)—C(6)—H(4)	120.5 (7)
C(7)—N(1)—H(6)	116.5 (7)	C(4)—C(5)—C(6)	119.87 (3)
N(1)—C(1)—C(2)	124.05 (3)	C(4)—C(5)—H(3)	120.0 (6)
N(1)—C(1)—C(6)	116.55 (3)	C(6)—C(5)—H(3)	120.1 (6)
C(2)—C(1)—C(6)	119.38 (3)	O(2)—C(7)—N(1)	123.34 (3)
C(2)—C(3)—C(4)	120.62 (3)	O(2)—C(7)—C(8)	121.66 (3)
C(2)—C(3)—H(2)	118.5 (6)	N(1)—C(7)—C(8)	115.00 (3)
C(4)—C(3)—H(2)	120.9 (6)	C(7)—C(8)—H(9)	109.2 (7)
C(1)—C(2)—C(3)	119.84 (3)	C(7)—C(8)—H(8)	111.2 (8)
C(1)—C(2)—H(1)	118.4 (7)	C(7)—C(8)—H(7)	110.5 (7)
C(3)—C(2)—H(1)	121.8 (7)	H(9)—C(8)—H(8)	111.4 (11)
O(1)—C(4)—C(3)	118.36 (3)	H(9)—C(8)—H(7)	104.8 (10)
O(1)—C(4)—C(5)	122.10 (3)	H(8)—C(8)—H(7)	109.5 (11)
C(3)—C(4)—C(5)	119.54 (3)