The crystal structure of perdeuterated methanol hemiammoniate (CD₃OD·0.5ND₃) determined from neutron powder diffraction data at 4.2 and 180 K

The crystal structure of perdeuterated methanol hemiammoniate, CD₃OD·0.5ND₃, has been solved from neutron powder diffraction data collected at 4.2 and 180 K. The structure is orthorhombic, space group Pn2₁a (Z = 4), with unit-cell dimensions a = 12.70615 (16), b = 8.84589 (9), c = 4.73876 (4) Å, V = 532.623 (8) ų [ρ_calc = 1149.57 (2) kg m⁻³] at 4.2 K, and a = 12.90413 (16), b = 8.96975 (8), c = 4.79198 (4) Å, V = 554.656 (7) ų [ρ_calc = 1103.90 (1) kg m⁻³] at 180 K. The crystal structure was determined by ab initio methods from the powder data; atomic coordinates and isotropic displacement parameters were subsequently refined by the Rietveld method to R_p ≃ 2% at both temperatures. The crystal structure comprises a three-dimensionally hydrogen-bonded network in which the ND₃ molecules are tetrahedrally coordinated by the hydroxy moieties of the methanol molecule. This connectivity leads to the formation of zigzag chains of ammonia–hydroxy groups extending along the c axis, formed via N—D···O hydrogen bonds; these chains are cross-linked along the a axis through the hydroxy moiety of the second methanol molecule via N—D···O and O—D···O hydrogen bonds. This `bridging' hydroxy group in turn donates an O—D···N hydrogen bond to ammonia in adjacent chains stacked along the b axis. The methyl deuterons in methanol hemiammoniate, unlike those in methanol monoammoniate, do not participate in hydrogen bonding and reveal evidence of orientational disorder at 180 K. The relative volume change on warming from 4.2 to 180 K, ΔV/V, is + 4.14%, which is comparable to, but more nearly isotropic (as determined from the relative change in axial lengths, e.g. Δa/a) than, that observed in deuterated methanol monohydrate, and very similar to what is observed in methanol monoammoniate.

Computing details

(METHANOL_HEMIAMMONIA_phase_1)

Crystal data

CD7NO	c = 7.5847 (3) Å
Mr = 56.11	V = 640.88 (3) Å^3
Orthorhombic, Pbca	Z = 8
a = 11.0386 (4) Å	? radiation, λ = ? Å
b = 7.6547 (3) Å	?; ?; ?, ?; ?; ? × ?; ?; ? mm

Data collection

Refinement

Least-squares matrix: full	4404 data points
Rp = 0.023	Profile function: TOF Profile function number 3 with 21 terms Profile coefficients for exponential pseudovoigt convolution Von Dreele, 1990 (unpublished) #1 (alp ) = 0.1759 #2 (bet-0) = 0.024093 #3 (bet-1) = 0.007850 #4 (sig-0) = 0.0 #5 (sig-1) = 2602.6 #6 (sig-2) = 106.7 #7 (gam-0) = 0.00 #8 (gam-1) = 0.00 #9 (gam-2) = 0.00 #10(gsf ) = 0.00 #11(g1ec ) = 0.00 #12(g2ec ) = 0.00 #13(rstr ) = 0.000 #14(rsta ) = 0.000 #15(rsca ) = 0.000 #16(L11) = 0.000 #17(L22) = 0.000 #18(L33) = 0.000 #19(L12) = 0.000 #20(L13) = 0.000 #21(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0, TOF Profile function number 3 with 21 terms Profile coefficients for exponential pseudovoigt convolution Von Dreele, 1990 (unpublished) #1 (alp ) = 0.1759 #2 (bet-0) = 0.024093 #3 (bet-1) = 0.007850 #4 (sig-0) = 0.0 #5 (sig-1) = 2284.4 #6 (sig-2) = 78.2 #7 (gam-0) = 0.00 #8 (gam-1) = 33.26 #9 (gam-2) = 0.00 #10(gsf ) = 0.00 #11(g1ec ) = 0.00 #12(g2ec ) = 0.00 #13(rstr ) = 0.000 #14(rsta ) = 0.000 #15(rsca ) = 0.000 #16(L11) = 0.000 #17(L22) = 0.000 #18(L33) = 0.000 #19(L12) = 0.000 #20(L13) = 0.000 #21(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rwp = 0.027	5 parameters
Rexp = 0.009	22 restraints
R(F^2) = 0.05592	(Δ/σ)max < 0.001
χ^2 = 54.317	Background function: GSAS Background function number 1 with 15 terms. Shifted Chebyshev function of 1st kind 1: 5.47986 2: -0.604934 3: -9.454000E-02 4: 3.727370E-02 5: -0.254440 6: 0.150723 7: -7.130570E-02 8: -2.600680E-02 9: -6.342830E-0210: -5.013720E-0211: 2.116950E-0212: -6.323090E-03 13: -1.822140E-0214: 2.743080E-0215: -5.135170E-02

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

	x	y	z	Uiso*/Ueq
C	0.26307	0.04606	0.21694	0.01067
O	0.13628	0.01387	0.23358	0.009
D1	0.28569	0.17895	0.25136	0.03333
D2	0.29373	0.01828	0.08409	0.03933
D3	0.31134	−0.04138	0.2996	0.03233
D4	0.09104	0.09952	0.15652	0.01733
N	0.49051	0.74662	1.02666	0.00967
D5	0.54064	0.82819	1.10533	0.02333
D6	0.44258	0.8252	0.94656	0.02267
D7	0.54772	0.6783	0.95125	0.023

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C	0.009	0.007	0.016	0.002	0.002	−0.001
O	0.008	0.006	0.013	0.002	−0.002	0.001
D1	0.02	0.024	0.056	−0.008	0.003	−0.012
D2	0.023	0.077	0.018	−0.004	0.011	−0.005
D3	0.016	0.034	0.047	0.002	−0.006	0.02
D4	0.02	0.019	0.013	0.001	−0.001	0.004
N	0.009	0.011	0.009	0.007	−0.001	0.001
D5	0.026	0.024	0.02	−0.005	−0.003	−0.008
D6	0.027	0.023	0.018	−0.002	−0.005	0.004
D7	0.023	0.018	0.028	0.006	0.0	−0.002

Geometric parameters (Å, º)

C—O	1.4267 (1)	D3—D2	1.7083 (1)
C—D1	1.0795 (1)	D4—C	1.9959 (1)
C—D2	1.0840 (1)	D4—O	1.0104 (1)
C—D3	1.0607 (1)	D4—N^i	1.7460 (1)
C—D4	1.9959 (1)	N—D4^ii	1.7460 (1)
O—C	1.4267 (1)	N—D5	1.0257 (1)
O—D3	2.0406 (1)	N—D6	1.0054 (1)
O—D4	1.0104 (1)	N—D7	0.9997 (1)
D1—C	1.0795 (1)	D5—N	1.0257 (1)
D1—D2	1.7692 (1)	D5—D6	1.6194 (1)
D1—D3	1.7489 (1)	D5—D7	1.6396 (1)
D2—C	1.0840 (1)	D6—N	1.0054 (1)
D2—D1	1.7692 (1)	D6—D5	1.6194 (1)
D2—D3	1.7083 (1)	D6—D7	1.6164 (1)
D3—C	1.0607 (1)	D7—N	0.9997 (1)
D3—O	2.0406 (1)	D7—D5	1.6396 (1)
D3—D1	1.7489 (1)	D7—D6	1.6164 (1)
O—C—D1	111.6090 (2)	D2—C—D3	105.593 (2)
O—C—D2	110.7707 (7)	C—O—D4	108.7611 (16)
O—C—D3	109.3621 (16)	D5—N—D6	105.737 (3)
D1—C—D2	109.7211 (6)	D5—N—D7	108.087 (2)
D1—C—D3	109.604 (2)	D6—N—D7	107.438 (3)

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

(METHANOL_HEMIAMMONIA_phase_2)

Crystal data

C2D11NO2	c = 4.73876 (4) Å
Mr = 92.18	V = 532.62 (1) Å^3
Orthorhombic, Pn21a	Z = 4
a = 12.70615 (16) Å	? radiation, λ = ? Å
b = 8.84589 (9) Å	?; ?; ?, ?; ?; ? × ?; ?; ? mm

Data collection

Refinement

Least-squares matrix: full	4404 data points
Rp = 0.023	Profile function: TOF Profile function number 3 with 21 terms Profile coefficients for exponential pseudovoigt convolution Von Dreele, 1990 (unpublished) #1 (alp ) = 0.1759 #2 (bet-0) = 0.024093 #3 (bet-1) = 0.007850 #4 (sig-0) = 0.0 #5 (sig-1) = 2602.6 #6 (sig-2) = 106.7 #7 (gam-0) = 0.00 #8 (gam-1) = 0.00 #9 (gam-2) = 0.00 #10(gsf ) = 0.00 #11(g1ec ) = 0.00 #12(g2ec ) = 0.00 #13(rstr ) = 0.000 #14(rsta ) = 0.000 #15(rsca ) = 0.000 #16(L11) = 0.000 #17(L22) = 0.000 #18(L33) = 0.000 #19(L12) = 0.000 #20(L13) = 0.000 #21(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0, TOF Profile function number 3 with 21 terms Profile coefficients for exponential pseudovoigt convolution Von Dreele, 1990 (unpublished) #1 (alp ) = 0.1759 #2 (bet-0) = 0.024093 #3 (bet-1) = 0.007850 #4 (sig-0) = 0.0 #5 (sig-1) = 2284.4 #6 (sig-2) = 78.2 #7 (gam-0) = 0.00 #8 (gam-1) = 33.26 #9 (gam-2) = 0.00 #10(gsf ) = 0.00 #11(g1ec ) = 0.00 #12(g2ec ) = 0.00 #13(rstr ) = 0.000 #14(rsta ) = 0.000 #15(rsca ) = 0.000 #16(L11) = 0.000 #17(L22) = 0.000 #18(L33) = 0.000 #19(L12) = 0.000 #20(L13) = 0.000 #21(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rwp = 0.027	5 parameters
Rexp = 0.009	22 restraints
R(F^2) = 0.05592	(Δ/σ)max < 0.001
χ^2 = 54.317	Background function: GSAS Background function number 1 with 15 terms. Shifted Chebyshev function of 1st kind 1: 5.47986 2: -0.604934 3: -9.454000E-02 4: 3.727370E-02 5: -0.254440 6: 0.150723 7: -7.130570E-02 8: -2.600680E-02 9: -6.342830E-0210: -5.013720E-0211: 2.116950E-0212: -6.323090E-03 13: -1.822140E-0214: 2.743080E-0215: -5.135170E-02

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

	x	y	z	Uiso*/Ueq
C1	0.54422	0.2265	0.05788	0.00721*
O1	0.56931	0.22879	0.34733	0.00594*
D1	0.56403	0.33473	−0.04779	0.03087*
D2	0.46046	0.20635	0.02671	0.03741*
D3	0.58601	0.13177	−0.0443	0.02949*
D4	0.58619	0.34168	0.40422	0.01039*
N1	0.61428	0.52341	0.46339	0.00378*
D5	0.65748	0.53838	0.64563	0.0164*
D6	0.55199	0.59727	0.48765	0.01603*
D7	0.65814	0.55554	0.30293	0.01943*
C2	0.18865	0.90166	0.02951	0.00264*
O2	0.23586	1.04731	0.02785	0.00803*
D8	0.10738	0.90055	−0.02161	0.03038*
D9	0.20057	0.84732	0.2342	0.02986*
D10	0.23088	0.8297	−0.1249	0.03082*
D11	0.17797	1.11997	0.0717	0.01393*

Geometric parameters (Å, º)

C1—O1	1.4083 (1)	D5—O2^ii	2.0584 (1)
C1—D1	1.1093 (1)	D6—N1	1.0327 (1)
C1—D2	1.0891 (1)	D6—D5	1.6213 (1)
C1—D3	1.1040 (1)	D6—D7	1.6497 (1)
C1—D4	2.0040 (1)	D7—N1	0.9846 (1)
O1—C1	1.4083 (1)	D7—D5	1.6311 (1)
O1—D2	2.0641 (1)	D7—D6	1.6497 (1)
O1—D3	2.0557 (1)	D7—O2^iii	2.0680 (1)
O1—D4	1.0564 (1)	C2—O2	1.4212 (1)
O1—D11^i	1.7262 (1)	C2—D8	1.0607 (1)
D1—C1	1.1093 (1)	C2—D9	1.0931 (1)
D1—D2	1.7737 (1)	C2—D10	1.1084 (1)
D1—D3	1.8170 (1)	C2—D11	1.9462 (1)
D2—C1	1.0891 (1)	O2—D5^iv	2.0584 (1)
D2—O1	2.0641 (1)	O2—D7^v	2.0680 (1)
D2—D1	1.7737 (1)	O2—C2	1.4212 (1)
D2—D3	1.7588 (1)	O2—D10	2.0575 (1)
D3—C1	1.1040 (1)	O2—D11	0.9987 (1)
D3—O1	2.0557 (1)	D8—C2	1.0607 (1)
D3—D1	1.8170 (1)	D8—D9	1.7587 (1)
D3—D2	1.7588 (1)	D8—D10	1.7592 (1)
D4—C1	2.0040 (1)	D9—C2	1.0931 (1)
D4—O1	1.0564 (1)	D9—D8	1.7587 (1)
D4—N1	1.6704 (1)	D9—D10	1.7517 (1)
N1—D4	1.6704 (1)	D10—C2	1.1084 (1)
N1—D5	1.0319 (1)	D10—O2	2.0575 (1)
N1—D6	1.0327 (1)	D10—D8	1.7592 (1)
N1—D7	0.9846 (1)	D10—D9	1.7517 (1)
D5—N1	1.0319 (1)	D11—O1^vi	1.7262 (1)
D5—D6	1.6213 (1)	D11—C2	1.9462 (1)
D5—D7	1.6311 (1)	D11—O2	0.9987 (1)
O1—C1—D1	112.0788 (3)	D6—N1—D7	109.6988 (5)
O1—C1—D2	110.8322 (1)	O2—C2—D8	114.7102 (3)
O1—C1—D3	109.2208 (4)	O2—C2—D9	110.1865 (3)
D1—C1—D2	107.5670 (1)	O2—C2—D10	108.2157 (6)
D1—C1—D3	110.3599 (6)	D8—C2—D9	109.4762 (1)
D2—C1—D3	106.6337 (5)	D8—C2—D10	108.3779 (5)
C1—O1—D4	107.9420 (2)	D9—C2—D10	105.4401 (6)
D5—N1—D6	103.4933 (5)	C2—O2—D11	105.7498 (8)
D5—N1—D7	107.9495 (8)

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

(METHANOL_HEMIAMMONIA_phase_1_180)

Crystal data

CD7NO	c = 7.6781 (2) Å
Mr = 56.11	V = 666.66 (2) Å^3
Orthorhombic, Pbca	Z = 8
a = 11.2096 (3) Å	? radiation, λ = ? Å
b = 7.7456 (2) Å	?; ?; ?; ?; ?, ?; ?; ?; ?; ? × ?; ?; ?; ?; ? mm

Data collection

Refinement

Least-squares matrix: full	844 data points
Rp = 0.021	Profile function: TOF Profile function number 3 with 21 terms Profile coefficients for exponential pseudovoigt convolution Von Dreele, 1990 (unpublished) #1 (alp ) = 0.1759 #2 (bet-0) = 0.024090 #3 (bet-1) = 0.007850 #4 (sig-0) = 0.0 #5 (sig-1) = 6576.5 #6 (sig-2) = 23.1 #7 (gam-0) = 0.00 #8 (gam-1) = 18.72 #9 (gam-2) = 0.00 #10(gsf ) = 0.00 #11(g1ec ) = 0.00 #12(g2ec ) = 0.00 #13(rstr ) = 0.000 #14(rsta ) = 0.000 #15(rsca ) = 0.000 #16(L11) = 0.000 #17(L22) = 0.000 #18(L33) = 0.000 #19(L12) = 0.000 #20(L13) = 0.000 #21(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0, TOF Profile function number 3 with 21 terms Profile coefficients for exponential pseudovoigt convolution Von Dreele, 1990 (unpublished) #1 (alp ) = 0.1759 #2 (bet-0) = 0.024090 #3 (bet-1) = 0.007850 #4 (sig-0) = 0.0 #5 (sig-1) = 2849.9 #6 (sig-2) = 451.6 #7 (gam-0) = 0.00 #8 (gam-1) = 0.00 #9 (gam-2) = 0.00 #10(gsf ) = 0.00 #11(g1ec ) = 0.00 #12(g2ec ) = 0.00 #13(rstr ) = 0.000 #14(rsta ) = 0.000 #15(rsca ) = 0.000 #16(L11) = 0.000 #17(L22) = 0.000 #18(L33) = 0.000 #19(L12) = 0.000 #20(L13) = 0.000 #21(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rwp = 0.018	95 parameters
Rexp = 0.005	46 restraints
R(F^2) = 0.30927	(Δ/σ)max = 0.08
χ^2 = 57.456	Background function: GSAS Background function number 1 with 5 terms. Shifted Chebyshev function of 1st kind 1: 1.21689 2: -0.177543 3: -4.811630E-02 4: 4.716540E-02 5: -2.750360E-02

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

	x	y	z	Uiso*/Ueq
C	0.25504	0.0505	0.2268	0.05033
O	0.1338	0.01326	0.2297	0.034
D1	0.27587	0.1712	0.271	0.16867
D2	0.2875	0.0443	0.1019	0.17467
D3	0.30029	−0.0336	0.2982	0.138
D4	0.09216	0.098	0.1593	0.04
N	0.49062	0.74732	1.03034	0.03467
D5	0.54152	0.8274	1.1076	0.051
D6	0.44586	0.823	0.9528	0.057
D7	0.54881	0.67774	0.9542	0.05533

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C	0.043	0.054	0.054	−0.002	−0.001	0.005
O	0.037	0.021	0.044	−0.008	0.001	0.01
D1	0.057	0.071	0.378	−0.019	−0.022	−0.089
D2	0.1	0.338	0.086	−0.055	0.03	0.017
D3	0.032	0.13	0.252	0.019	−0.035	0.064
D4	0.036	0.036	0.048	−0.004	0.01	0.003
N	0.033	0.037	0.034	0.021	−0.004	0.005
D5	0.063	0.059	0.031	−0.011	−0.07	−0.02
D6	0.068	0.055	0.048	−0.024	−0.002	−0.006
D7	0.047	0.047	0.072	0.011	0.012	0.003

Geometric parameters (Å, º)

C—O	1.3895 (1)	D3—O	1.9727 (1)
C—D1	1.0216 (1)	D3—D1	1.6232 (1)
C—D2	1.0268 (1)	D3—D2	1.6298 (1)
C—D3	0.9910 (1)	D4—C	1.9333 (1)
C—D4	1.9333 (1)	D4—O	0.9700 (1)
O—C	1.3895 (1)	D4—N^i	1.7830 (1)
O—D1	2.0331 (1)	N—D4^ii	1.7830 (1)
O—D2	1.9973 (1)	N—D5	1.0306 (1)
O—D3	1.9727 (1)	N—D6	0.9746 (1)
O—D4	0.9700 (1)	N—D7	1.0285 (1)
D1—C	1.0216 (1)	D5—N	1.0306 (1)
D1—O	2.0331 (1)	D5—D6	1.6012 (1)
D1—D2	1.6337 (1)	D5—D7	1.6546 (1)
D1—D3	1.6232 (1)	D6—N	0.9746 (1)
D2—C	1.0268 (1)	D6—D5	1.6012 (1)
D2—O	1.9973 (1)	D6—D7	1.6118 (1)
D2—D1	1.6337 (1)	D7—N	1.0285 (1)
D2—D3	1.6298 (1)	D7—D5	1.6546 (1)
D3—C	0.9910 (1)	D7—D6	1.6118 (1)
O—C—D1	114.0910 (1)	D2—C—D3	107.7294 (14)
O—C—D2	110.6005 (6)	C—O—D4	108.7395 (11)
O—C—D3	110.8113 (12)	D5—N—D6	105.941 (2)
D1—C—D2	105.7863 (7)	D5—N—D7	106.9442 (17)
D1—C—D3	107.5033 (18)	D6—N—D7	107.1257 (19)

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

(METHANOL_HEMIAMMONIA_phase_2_180)

Crystal data

C2D11.00NO2	c = 4.79198 (4) Å
Mr = 92.18	V = 554.66 (1) Å^3
Orthorhombic, Pn21a	Z = 4
a = 12.90413 (16) Å	? radiation, λ = ? Å
b = 8.96975 (8) Å	?; ?; ?; ?; ?, ?; ?; ?; ?; ? × ?; ?; ?; ?; ? mm

Data collection

Refinement

Least-squares matrix: full	844 data points
Rp = 0.021	Profile function: TOF Profile function number 3 with 21 terms Profile coefficients for exponential pseudovoigt convolution Von Dreele, 1990 (unpublished) #1 (alp ) = 0.1759 #2 (bet-0) = 0.024090 #3 (bet-1) = 0.007850 #4 (sig-0) = 0.0 #5 (sig-1) = 6576.5 #6 (sig-2) = 23.1 #7 (gam-0) = 0.00 #8 (gam-1) = 18.72 #9 (gam-2) = 0.00 #10(gsf ) = 0.00 #11(g1ec ) = 0.00 #12(g2ec ) = 0.00 #13(rstr ) = 0.000 #14(rsta ) = 0.000 #15(rsca ) = 0.000 #16(L11) = 0.000 #17(L22) = 0.000 #18(L33) = 0.000 #19(L12) = 0.000 #20(L13) = 0.000 #21(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0, TOF Profile function number 3 with 21 terms Profile coefficients for exponential pseudovoigt convolution Von Dreele, 1990 (unpublished) #1 (alp ) = 0.1759 #2 (bet-0) = 0.024090 #3 (bet-1) = 0.007850 #4 (sig-0) = 0.0 #5 (sig-1) = 2849.9 #6 (sig-2) = 451.6 #7 (gam-0) = 0.00 #8 (gam-1) = 0.00 #9 (gam-2) = 0.00 #10(gsf ) = 0.00 #11(g1ec ) = 0.00 #12(g2ec ) = 0.00 #13(rstr ) = 0.000 #14(rsta ) = 0.000 #15(rsca ) = 0.000 #16(L11) = 0.000 #17(L22) = 0.000 #18(L33) = 0.000 #19(L12) = 0.000 #20(L13) = 0.000 #21(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rwp = 0.018	95 parameters
Rexp = 0.005	46 restraints
R(F^2) = 0.30927	(Δ/σ)max = 0.08
χ^2 = 57.456	Background function: GSAS Background function number 1 with 5 terms. Shifted Chebyshev function of 1st kind 1: 1.21689 2: -0.177543 3: -4.811630E-02 4: 4.716540E-02 5: -2.750360E-02

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5449 (2)	0.2238 (3)	0.0534 (5)	0.0488 (10)*
O1	0.5684 (3)	0.2320 (4)	0.3440 (4)	0.0391 (11)*
D1	0.5729 (6)	0.3236 (6)	−0.0472 (9)	0.068 (2)*	0.607 (6)
D2	0.4621 (2)	0.2152 (11)	0.0374 (9)	0.050 (2)*	0.607 (6)
D3	0.5823 (6)	0.1263 (7)	−0.0325 (10)	0.080 (3)*	0.607 (6)
D4	0.5856 (2)	0.3345 (4)	0.3991 (6)	0.0256 (9)*
N1	0.61410 (17)	0.5248 (3)	0.4604 (4)	0.0346 (8)*
D5	0.6593 (2)	0.5300 (5)	0.6305 (5)	0.0524 (12)*
D6	0.55341 (17)	0.5941 (4)	0.4829 (7)	0.0613 (14)*
D7	0.6558 (3)	0.5556 (5)	0.2934 (5)	0.0531 (13)*
C2	0.1840 (2)	0.9041 (3)	0.0101 (6)	0.0712 (16)*
O2	0.2295 (3)	1.0480 (3)	0.0361 (6)	0.0355 (12)*
D8	0.1110 (4)	0.9120 (6)	−0.0899 (18)	0.082 (4)*	0.515 (8)
D9	0.1744 (6)	0.8626 (5)	0.2255 (8)	0.051 (3)*	0.515 (8)
D10	0.2370 (4)	0.8328 (4)	−0.0995 (15)	0.027 (2)*	0.515 (8)
D11	0.1761 (3)	1.1255 (4)	0.0667 (7)	0.0471 (11)*
D1b	0.4955 (8)	0.3167 (8)	0.0012 (9)	0.053 (4)*	0.393 (6)
D2b	0.5058 (9)	0.1194 (7)	0.0148 (10)	0.041 (3)*	0.393 (6)
D3b	0.6167 (3)	0.2290 (15)	−0.0617 (7)	0.046 (3)*	0.393 (6)
D8b	0.1824 (8)	0.8753 (7)	−0.2093 (8)	0.056 (3)*	0.485 (8)
D9b	0.1063 (4)	0.9081 (5)	0.092 (2)	0.070 (4)*	0.485 (8)
D10b	0.2308 (5)	0.8254 (4)	0.125 (2)	0.141 (5)*	0.485 (8)

Geometric parameters (Å, º)

C1—O1	1.427 (2)	O2—D10	2.039 (3)
C1—D1	1.078 (3)	O2—D11	0.990 (3)
C1—D2	1.075 (3)	O2—D8b	2.0372 (18)
C1—D3	1.080 (3)	O2—D9b	2.0424 (18)
C1—D4	2.001 (4)	O2—D10b	2.0408 (18)
C1—D1b	1.0787 (17)	D8—C2	1.060 (3)
C1—D2b	1.0799 (17)	D8—O2	2.047 (4)
C1—D3b	1.0784 (16)	D8—D9	1.7749 (8)
O1—C1	1.427 (2)	D8—D10	1.7752 (8)
O1—D1	2.047 (3)	D8—D8b	1.134 (6)
O1—D2	2.016 (3)	D8—D9b	0.876 (7)
O1—D3	2.046 (3)	D9—C2	1.104 (3)
O1—D4	0.982 (3)	D9—O2	2.023 (3)
O1—D11^i	1.740 (5)	D9—D8	1.7749 (8)
O1—D1b	2.0397 (18)	D9—D10	1.7749 (8)
O1—D2b	2.0398 (18)	D9—D9b	1.160 (7)
O1—D3b	2.0415 (18)	D9—D10b	0.935 (8)
D1—C1	1.078 (3)	D10—C2	1.074 (3)
D1—O1	2.047 (3)	D10—O2	2.039 (3)
D1—D2	1.7752 (8)	D10—D8	1.7752 (8)
D1—D3	1.7746 (8)	D10—D9	1.7749 (8)
D1—D1b	1.026 (7)	D10—D8b	0.958 (7)
D1—D3b	1.022 (7)	D10—D10b	1.079 (7)
D2—C1	1.075 (3)	D11—O1^ii	1.740 (5)
D2—O1	2.016 (3)	D11—C2	2.007 (4)
D2—D1	1.7752 (8)	D11—O2	0.990 (3)
D2—D3	1.7754 (8)	D1b—C1	1.0787 (17)
D2—D1b	1.022 (7)	D1b—O1	2.0397 (18)
D2—D2b	1.034 (7)	D1b—D1	1.026 (7)
D3—C1	1.080 (3)	D1b—D2	1.022 (7)
D3—O1	2.046 (3)	D1b—D2b	1.7760 (18)
D3—D1	1.7746 (8)	D1b—D3b	1.7757 (18)
D3—D2	1.7754 (8)	D2b—C1	1.0799 (17)
D3—D2b	1.014 (7)	D2b—O1	2.0398 (18)
D3—D3b	1.032 (7)	D2b—D2	1.034 (7)
D4—C1	2.001 (4)	D2b—D3	1.014 (7)
D4—O1	0.982 (3)	D2b—D1b	1.7760 (18)
D4—N1	1.770 (4)	D2b—D3b	1.7737 (18)
N1—D4	1.770 (4)	D3b—C1	1.0784 (16)
N1—D5	1.0034 (16)	D3b—O1	2.0415 (18)
N1—D6	1.0061 (16)	D3b—D1	1.022 (7)
N1—D7	1.0035 (16)	D3b—D3	1.032 (7)
D5—N1	1.0034 (16)	D3b—D1b	1.7757 (18)
D5—D6	1.6423 (18)	D3b—D2b	1.7737 (18)
D5—D7	1.6325 (18)	D8b—C2	1.0831 (17)
D6—N1	1.0061 (16)	D8b—O2	2.0372 (18)
D6—D5	1.6423 (18)	D8b—D8	1.134 (6)
D6—D7	1.6404 (18)	D8b—D10	0.958 (7)
D7—N1	1.0035 (16)	D8b—D9b	1.7718 (18)
D7—D5	1.6325 (18)	D8b—D10b	1.7755 (18)
D7—D6	1.6404 (18)	D9b—C2	1.0777 (17)
C2—O2	1.423 (2)	D9b—O2	2.0424 (18)
C2—D8	1.060 (3)	D9b—D8	0.876 (7)
C2—D9	1.104 (3)	D9b—D9	1.160 (7)
C2—D10	1.074 (3)	D9b—D8b	1.7718 (18)
C2—D11	2.007 (4)	D9b—D10b	1.7763 (18)
C2—D8b	1.0831 (17)	D10b—C2	1.0792 (17)
C2—D9b	1.0777 (17)	D10b—O2	2.0408 (18)
C2—D10b	1.0792 (17)	D10b—D9	0.935 (8)
O2—C2	1.423 (2)	D10b—D10	1.079 (7)
O2—D8	2.047 (4)	D10b—D8b	1.7755 (18)
O2—D9	2.023 (3)	D10b—D9b	1.7763 (18)
O1—C1—D1	108.8 (3)	D8—C2—D8b	63.9 (4)
O1—C1—D2	106.5 (3)	D8—C2—D9b	48.4 (4)
O1—C1—D3	108.6 (3)	D8—C2—D10b	140.5 (4)
O1—C1—D1b	108.19 (19)	D9—C2—D10	109.2 (3)
O1—C1—D2b	108.13 (19)	D9—C2—D8b	145.6 (4)
O1—C1—D3b	108.35 (19)	D9—C2—D9b	64.2 (4)
D1—C1—D2	111.1 (3)	D9—C2—D10b	50.7 (4)
D1—C1—D3	110.6 (2)	D10—C2—D8b	52.8 (4)
D1—C1—D1b	56.8 (4)	D10—C2—D9b	142.2 (4)
D1—C1—D2b	143.0 (4)	D10—C2—D10b	60.2 (4)
D1—C1—D3b	56.6 (4)	D8b—C2—D9b	110.2 (2)
D2—C1—D3	111.0 (3)	D8b—C2—D10b	110.4 (2)
D2—C1—D1b	56.7 (4)	D9b—C2—D10b	110.9 (2)
D2—C1—D2b	57.4 (4)	C2—O2—D11	111.3 (3)
D2—C1—D3b	145.1 (3)	C2—D8—D8b	59.1 (2)
D3—C1—D1b	143.2 (4)	C2—D8—D9b	66.9 (3)
D3—C1—D2b	56.0 (4)	D8b—D8—D9b	123.2 (4)
D3—C1—D3b	57.1 (4)	C2—D9—D9b	56.8 (2)
D1b—C1—D2b	110.7 (2)	C2—D9—D10b	63.3 (3)
D1b—C1—D3b	110.8 (2)	D9b—D9—D10b	115.5 (4)
D2b—C1—D3b	110.5 (2)	C2—D10—D8b	64.1 (3)
C1—O1—D4	111.0 (3)	C2—D10—D10b	60.2 (3)
C1—D1—D1b	61.6 (2)	D8b—D10—D10b	121.1 (4)
C1—D1—D3b	61.7 (3)	C1—D1b—D1	61.6 (3)
D1b—D1—D3b	120.2 (4)	C1—D1b—D2	61.5 (3)
C1—D2—D1b	61.9 (2)	D1—D1b—D2	120.1 (4)
C1—D2—D2b	61.6 (2)	C1—D2b—D2	61.1 (2)
D1b—D2—D2b	119.5 (3)	C1—D2b—D3	62.0 (3)
C1—D3—D2b	62.0 (2)	D2—D2b—D3	120.2 (4)
C1—D3—D3b	61.4 (3)	C1—D3b—D1	61.7 (2)
D2b—D3—D3b	120.3 (4)	C1—D3b—D3	61.5 (2)
D5—N1—D6	109.6 (2)	D1—D3b—D3	119.6 (3)
D5—N1—D7	108.9 (2)	C2—D8b—D8	57.1 (2)
D6—N1—D7	109.4 (2)	C2—D8b—D10	63.1 (3)
O2—C2—D8	110.2 (3)	D8—D8b—D10	115.8 (4)
O2—C2—D9	105.7 (3)	C2—D9b—D8	64.8 (3)
O2—C2—D10	108.7 (3)	C2—D9b—D9	59.0 (3)
O2—C2—D8b	108.0 (2)	D8—D9b—D9	120.7 (4)
O2—C2—D9b	108.8 (2)	C2—D10b—D9	66.0 (3)
O2—C2—D10b	108.5 (2)	C2—D10b—D10	59.7 (2)
D8—C2—D9	110.2 (3)	D9—D10b—D10	123.3 (4)
D8—C2—D10	112.6 (3)

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