Supra­molecular architectures of N-acetyl-L-proline monohydrate and N-benzyl-L-proline

The title compounds, N-acetyl-L-proline monohydrate, C₇H₁₁NO₃·H₂O, (I), and N-benzyl-L-proline, C₁₂H₁₅NO₂, (II), crystallize in the monoclinic space group P2₁ with Z′ = 1 and Z′ = 2, respectively. The conformation of C^γ with respect to the carb­oxy­lic acid group in (I) is C^γ-exo or UP pucker, with the pyrrolidine ring twisted, while in (II), it is C^γ-endo or DOWN, with the pyrrolidine ring assuming an envelope conformation. The crystal packing inter­actions in (I) are composed of two substructures, one characterized by an R₆⁶(24) motif through O—H...O hydrogen bonds and the other by an R₄⁴(23) ring through C—H...O inter­actions. In (II), the crystal packing inter­actions consist of N—H...O and C—H...O hydrogen bonds. Proline (Pro) exists in its neutral form in (I) and is zwitterionic in (II). This difference in the ionization states of Pro is manifested through the absence of N—H...O and presence of O—H...O inter­actions in (I), and the presence of N—H...O and absence of O—H...O hydrogen bonds in (II). While C—H...O inter­actions are present in both (I) and (II), the geometry of the synthons formed by them and their mode of participation in inter­molecular inter­actions is different. Though the title compounds differ significantly in terms of modifications in the Pro skeleton, the differences in their supra­molecular structures may also be viewed as a result of the mol­ecular recognition facilitated by the presence of a solvent water mol­ecule in (I) and the zwitterionic state of the amino acid in (II).

Computing details

For both compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(prl021) N-Acetyl-L-proline monohydrate

Crystal data

C7H11NO3·H2O	F(000) = 188
Mr = 175.18	Dx = 1.367 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3028 reflections
a = 6.2876 (3) Å	θ = 3.2–32.6°
b = 10.7132 (5) Å	µ = 0.11 mm^−1
c = 6.7764 (3) Å	T = 100 K
β = 111.143 (1)°	Block, colourless
V = 425.73 (3) Å^3	0.33 × 0.29 × 0.20 mm
Z = 2

Data collection

Bruker Kappa APEXII area-detector diffractometer	1605 independent reflections
Radiation source: fine-focus sealed tube	1577 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 32.6°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −7→9
Tmin = 0.964, Tmax = 0.978	k = −16→15
10935 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.0228P] where P = (Fo^2 + 2Fc^2)/3
1605 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.34 e Å^−3
2 restraints	Δρmin = −0.34 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1W	0.25777 (12)	0.10499 (7)	0.38337 (11)	0.01809 (14)
O1	0.16647 (12)	0.30996 (6)	0.17278 (11)	0.01696 (13)
H1	0.2142	0.2516	0.2606	0.025*
O2	0.38606 (12)	0.42695 (7)	0.44520 (10)	0.01787 (14)
O3	−0.05574 (12)	0.58499 (7)	0.32887 (12)	0.01871 (14)
N1	0.20972 (13)	0.64355 (7)	0.19803 (12)	0.01394 (14)
C1	0.25938 (14)	0.41643 (8)	0.26143 (13)	0.01349 (15)
C2	0.20118 (14)	0.52137 (8)	0.10077 (13)	0.01355 (14)
H2A	0.0470	0.5072	−0.0098	0.016*
C3	0.38220 (17)	0.53084 (9)	−0.00327 (15)	0.01792 (16)
H3A	0.5336	0.5034	0.0952	0.022*
H3B	0.3387	0.4800	−0.1339	0.022*
C4	0.38250 (18)	0.67017 (10)	−0.05307 (14)	0.02064 (18)
H4A	0.5281	0.6951	−0.0668	0.025*
H4B	0.2552	0.6914	−0.1856	0.025*
C5	0.35274 (16)	0.73344 (9)	0.13729 (14)	0.01673 (16)
H5A	0.5015	0.7458	0.2534	0.020*
H5B	0.2752	0.8151	0.0978	0.020*
C6	0.07107 (14)	0.66836 (8)	0.30458 (13)	0.01427 (15)
C7	0.07690 (17)	0.79800 (9)	0.39021 (15)	0.01805 (16)
H7A	−0.0239	0.8026	0.4716	0.027*
H7B	0.0253	0.8575	0.2726	0.027*
H7C	0.2331	0.8186	0.4823	0.027*
H1W1	0.198 (3)	0.095 (2)	0.467 (3)	0.034 (5)*
H2W1	0.373 (3)	0.0642 (19)	0.427 (3)	0.027 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1W	0.0204 (3)	0.0162 (3)	0.0203 (3)	0.0031 (2)	0.0105 (2)	0.0035 (2)
O1	0.0205 (3)	0.0125 (3)	0.0177 (3)	−0.0015 (2)	0.0068 (2)	−0.0003 (2)
O2	0.0188 (3)	0.0167 (3)	0.0165 (3)	−0.0013 (2)	0.0043 (2)	0.0018 (2)
O3	0.0187 (3)	0.0184 (3)	0.0229 (3)	−0.0033 (2)	0.0121 (2)	−0.0015 (2)
N1	0.0150 (3)	0.0125 (3)	0.0159 (3)	−0.0013 (2)	0.0074 (2)	0.0007 (2)
C1	0.0128 (3)	0.0129 (3)	0.0167 (3)	0.0001 (3)	0.0077 (3)	0.0007 (3)
C2	0.0146 (3)	0.0132 (3)	0.0140 (3)	−0.0008 (3)	0.0067 (3)	0.0000 (3)
C3	0.0202 (4)	0.0191 (4)	0.0188 (4)	−0.0007 (3)	0.0122 (3)	0.0003 (3)
C4	0.0238 (4)	0.0228 (4)	0.0195 (3)	−0.0023 (3)	0.0128 (3)	0.0037 (3)
C5	0.0172 (3)	0.0156 (4)	0.0194 (3)	−0.0024 (3)	0.0090 (3)	0.0028 (3)
C6	0.0141 (3)	0.0148 (3)	0.0144 (3)	0.0008 (3)	0.0057 (2)	0.0008 (3)
C7	0.0227 (4)	0.0138 (3)	0.0192 (3)	0.0003 (3)	0.0095 (3)	−0.0003 (3)

Geometric parameters (Å, º)

O1W—H1W1	0.797 (17)	C3—C4	1.5305 (15)
O1W—H2W1	0.804 (17)	C3—H3A	0.9900
O1—C1	1.3230 (10)	C3—H3B	0.9900
O1—H1	0.8400	C4—C5	1.5272 (14)
O2—C1	1.2175 (10)	C4—H4A	0.9900
O3—C6	1.2470 (11)	C4—H4B	0.9900
N1—C6	1.3439 (11)	C5—H5A	0.9900
N1—C2	1.4578 (11)	C5—H5B	0.9900
N1—C5	1.4739 (12)	C6—C7	1.5006 (13)
C1—C2	1.5151 (12)	C7—H7A	0.9800
C2—C3	1.5433 (13)	C7—H7B	0.9800
C2—H2A	1.0000	C7—H7C	0.9800
H1W1—O1W—H2W1	105 (2)	C5—C4—H4A	111.0
C1—O1—H1	109.5	C3—C4—H4A	111.0
C6—N1—C2	119.68 (7)	C5—C4—H4B	111.0
C6—N1—C5	126.88 (8)	C3—C4—H4B	111.0
C2—N1—C5	112.78 (7)	H4A—C4—H4B	109.0
O2—C1—O1	124.26 (8)	N1—C5—C4	102.64 (8)
O2—C1—C2	124.45 (8)	N1—C5—H5A	111.2
O1—C1—C2	111.15 (7)	C4—C5—H5A	111.2
N1—C2—C1	112.42 (7)	N1—C5—H5B	111.2
N1—C2—C3	103.56 (7)	C4—C5—H5B	111.2
C1—C2—C3	110.50 (7)	H5A—C5—H5B	109.2
N1—C2—H2A	110.1	O3—C6—N1	119.93 (8)
C1—C2—H2A	110.1	O3—C6—C7	122.64 (8)
C3—C2—H2A	110.1	N1—C6—C7	117.43 (8)
C4—C3—C2	102.98 (8)	C6—C7—H7A	109.5
C4—C3—H3A	111.2	C6—C7—H7B	109.5
C2—C3—H3A	111.2	H7A—C7—H7B	109.5
C4—C3—H3B	111.2	C6—C7—H7C	109.5
C2—C3—H3B	111.2	H7A—C7—H7C	109.5
H3A—C3—H3B	109.1	H7B—C7—H7C	109.5
C5—C4—C3	103.67 (7)
C6—N1—C2—C1	−60.72 (10)	C2—N1—C6—O3	3.61 (12)
C5—N1—C2—C1	127.95 (8)	C5—N1—C6—O3	173.60 (8)
C6—N1—C2—C3	179.99 (7)	C2—N1—C6—C7	−176.38 (7)
C5—N1—C2—C3	8.66 (9)	C5—N1—C6—C7	−6.39 (12)
O2—C1—C2—N1	−29.25 (12)	O1—C1—C2—N1	154.81 (7)
O1—C1—C2—N1	154.81 (7)	O2—C1—C2—N1	−29.25 (12)
O2—C1—C2—C3	85.91 (10)	N1—C2—C3—C4	−28.62 (9)
O1—C1—C2—C3	−90.03 (9)	C2—C3—C4—C5	38.11 (9)
N1—C2—C3—C4	−28.62 (9)	C3—C4—C5—N1	−32.47 (9)
C1—C2—C3—C4	−149.23 (8)	C4—C5—N1—C2	14.93 (9)
C2—C3—C4—C5	38.11 (9)	C5—N1—C2—C3	8.66 (9)
C6—N1—C5—C4	−155.65 (8)	C2—N1—C6—O3	3.61 (12)
C2—N1—C5—C4	14.93 (9)	C2—N1—C6—C7	−176.38 (7)
C3—C4—C5—N1	−32.47 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3^i	0.80 (2)	1.90 (2)	2.6923 (10)	175 (3)
O1W—H2W1···O2^ii	0.80 (2)	2.07 (2)	2.8507 (10)	166 (2)
O1—H1···O1W	0.84	1.75	2.5684 (10)	163
C4—H4A···O1^iii	0.99	2.59	3.5501 (12)	163
C7—H7C···O2^iv	0.98	2.54	3.4406 (12)	152

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

(prl017) N-Benzyl-L-proline

Crystal data

C12H15NO2	F(000) = 440
Mr = 205.25	Dx = 1.302 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8043 reflections
a = 8.7552 (7) Å	θ = 2.9–35.1°
b = 10.6254 (8) Å	µ = 0.09 mm^−1
c = 11.2816 (8) Å	T = 100 K
β = 93.737 (2)°	Block, colourless
V = 1047.27 (14) Å^3	0.49 × 0.35 × 0.24 mm
Z = 4

Data collection

Bruker Kappa APEXII area-detector diffractometer	4800 independent reflections
Radiation source: fine-focus sealed tube	4436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 35.1°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −14→14
Tmin = 0.958, Tmax = 0.979	k = −15→17
18099 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.0405P] where P = (Fo^2 + 2Fc^2)/3
4800 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.35 e Å^−3
1 restraint	Δρmin = −0.22 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1A	0.61856 (12)	0.32428 (9)	−0.10200 (7)	0.02301 (18)
O2A	0.59164 (11)	0.26347 (8)	0.08645 (7)	0.02138 (16)
N1A	0.51397 (10)	0.48296 (9)	0.16407 (7)	0.01368 (14)
H1A	0.5191	0.4008	0.1924	0.016*
C1A	0.59243 (12)	0.34259 (10)	0.00415 (9)	0.01488 (16)
C2A	0.55915 (11)	0.48054 (10)	0.03700 (8)	0.01252 (15)
H2A	0.4748	0.5154	−0.0174	0.015*
C3A	0.70109 (12)	0.56494 (10)	0.03644 (9)	0.01641 (17)
H3A	0.7723	0.5347	−0.0220	0.020*
H3B	0.6722	0.6531	0.0175	0.020*
C4A	0.77286 (13)	0.55390 (12)	0.16281 (10)	0.0201 (2)
H4A	0.8290	0.4736	0.1748	0.024*
H4B	0.8432	0.6249	0.1826	0.024*
C5A	0.63320 (14)	0.55859 (14)	0.23540 (10)	0.0238 (2)
H5A	0.6556	0.5208	0.3148	0.029*
H5B	0.5985	0.6464	0.2454	0.029*
C6A	0.35512 (12)	0.53137 (10)	0.18130 (9)	0.01511 (17)
H6A	0.3402	0.5367	0.2674	0.018*
H6B	0.3447	0.6173	0.1478	0.018*
C7A	0.23322 (12)	0.44849 (10)	0.12285 (9)	0.01500 (17)
C8A	0.17069 (12)	0.47618 (12)	0.00899 (10)	0.01859 (18)
H8A	0.2066	0.5470	−0.0325	0.022*
C9A	0.05565 (13)	0.40030 (14)	−0.04434 (11)	0.0229 (2)
H9A	0.0145	0.4188	−0.1224	0.028*
C10A	0.00116 (14)	0.29755 (13)	0.01659 (12)	0.0243 (2)
H10A	−0.0785	0.2468	−0.0191	0.029*
C11A	0.06378 (14)	0.26948 (13)	0.12990 (12)	0.0234 (2)
H11A	0.0274	0.1988	0.1712	0.028*
C12A	0.17955 (13)	0.34423 (11)	0.18335 (10)	0.01825 (18)
H12A	0.2219	0.3244	0.2608	0.022*
O1B	0.36792 (11)	0.22077 (9)	0.50218 (8)	0.02390 (18)
O2B	0.45376 (11)	0.40134 (9)	0.42551 (7)	0.02149 (16)
N1B	0.52626 (10)	0.50874 (8)	0.63115 (7)	0.01357 (14)
H1B	0.5289	0.5305	0.5515	0.016*
C1B	0.42133 (12)	0.32975 (11)	0.50877 (9)	0.01606 (17)
C2B	0.45124 (11)	0.38057 (9)	0.63626 (8)	0.01327 (16)
H2B	0.5197	0.3214	0.6838	0.016*
C3B	0.30385 (13)	0.40287 (11)	0.69983 (10)	0.01821 (18)
H3D	0.2201	0.3478	0.6671	0.022*
H3C	0.3206	0.3872	0.7862	0.022*
C4B	0.26739 (14)	0.54111 (13)	0.67482 (11)	0.0231 (2)
H4C	0.2194	0.5527	0.5937	0.028*
H4D	0.1986	0.5755	0.7331	0.028*
C5B	0.42344 (15)	0.60231 (11)	0.68773 (10)	0.0212 (2)
H5C	0.4233	0.6842	0.6458	0.025*
H5D	0.4563	0.6157	0.7724	0.025*
C6B	0.68782 (12)	0.51302 (10)	0.68449 (8)	0.01598 (17)
H6C	0.6897	0.4856	0.7684	0.019*
H6D	0.7259	0.6007	0.6830	0.019*
C7B	0.79154 (12)	0.42941 (10)	0.61778 (9)	0.01495 (17)
C8B	0.83437 (13)	0.31084 (11)	0.66143 (10)	0.01866 (18)
H8B	0.8003	0.2832	0.7353	0.022*
C9B	0.92654 (14)	0.23287 (12)	0.59749 (11)	0.0223 (2)
H9B	0.9549	0.1521	0.6275	0.027*
C10B	0.97735 (14)	0.27332 (13)	0.48934 (11)	0.0220 (2)
H10B	1.0402	0.2201	0.4455	0.026*
C11B	0.93589 (13)	0.39185 (12)	0.44573 (10)	0.02041 (19)
H11B	0.9711	0.4198	0.3723	0.024*
C12B	0.84295 (12)	0.46949 (11)	0.50943 (9)	0.01682 (17)
H12B	0.8143	0.5501	0.4791	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0389 (5)	0.0188 (4)	0.0116 (3)	0.0033 (4)	0.0047 (3)	−0.0028 (3)
O2A	0.0343 (4)	0.0135 (3)	0.0168 (3)	−0.0003 (3)	0.0050 (3)	0.0029 (3)
N1A	0.0167 (3)	0.0148 (3)	0.0097 (3)	−0.0013 (3)	0.0025 (2)	−0.0004 (3)
C1A	0.0195 (4)	0.0127 (4)	0.0125 (4)	−0.0009 (3)	0.0018 (3)	−0.0011 (3)
C2A	0.0157 (4)	0.0129 (4)	0.0092 (3)	−0.0003 (3)	0.0023 (3)	0.0004 (3)
C3A	0.0178 (4)	0.0151 (4)	0.0166 (4)	−0.0034 (3)	0.0034 (3)	0.0007 (3)
C4A	0.0184 (4)	0.0236 (5)	0.0180 (4)	−0.0044 (4)	−0.0001 (3)	−0.0037 (4)
C5A	0.0222 (5)	0.0344 (6)	0.0151 (4)	−0.0094 (5)	0.0025 (4)	−0.0094 (4)
C6A	0.0181 (4)	0.0139 (4)	0.0139 (4)	0.0006 (3)	0.0055 (3)	−0.0013 (3)
C7A	0.0151 (4)	0.0148 (4)	0.0157 (4)	0.0010 (3)	0.0047 (3)	0.0000 (3)
C8A	0.0173 (4)	0.0212 (5)	0.0175 (4)	0.0019 (4)	0.0029 (3)	0.0016 (4)
C9A	0.0181 (4)	0.0280 (5)	0.0225 (5)	0.0023 (4)	0.0000 (4)	−0.0024 (4)
C10A	0.0168 (4)	0.0248 (5)	0.0316 (6)	−0.0017 (4)	0.0030 (4)	−0.0058 (5)
C11A	0.0202 (5)	0.0192 (5)	0.0318 (6)	−0.0023 (4)	0.0073 (4)	0.0008 (4)
C12A	0.0192 (4)	0.0161 (4)	0.0201 (4)	−0.0001 (4)	0.0061 (3)	0.0019 (3)
O1B	0.0297 (4)	0.0186 (4)	0.0243 (4)	−0.0069 (3)	0.0089 (3)	−0.0084 (3)
O2B	0.0310 (4)	0.0214 (4)	0.0123 (3)	−0.0027 (3)	0.0025 (3)	−0.0004 (3)
N1B	0.0192 (4)	0.0110 (3)	0.0109 (3)	0.0004 (3)	0.0040 (3)	−0.0006 (3)
C1B	0.0180 (4)	0.0164 (4)	0.0142 (4)	−0.0001 (3)	0.0038 (3)	−0.0035 (3)
C2B	0.0159 (4)	0.0116 (4)	0.0125 (3)	−0.0010 (3)	0.0030 (3)	−0.0008 (3)
C3B	0.0185 (4)	0.0199 (4)	0.0170 (4)	−0.0006 (4)	0.0065 (3)	−0.0012 (4)
C4B	0.0237 (5)	0.0248 (5)	0.0216 (5)	0.0093 (4)	0.0078 (4)	0.0012 (4)
C5B	0.0325 (6)	0.0127 (4)	0.0199 (4)	0.0040 (4)	0.0123 (4)	−0.0012 (3)
C6B	0.0208 (4)	0.0144 (4)	0.0126 (3)	−0.0030 (3)	−0.0001 (3)	−0.0015 (3)
C7B	0.0160 (4)	0.0141 (4)	0.0145 (4)	−0.0022 (3)	−0.0012 (3)	0.0003 (3)
C8B	0.0188 (4)	0.0184 (5)	0.0186 (4)	−0.0004 (4)	−0.0001 (3)	0.0043 (4)
C9B	0.0211 (5)	0.0200 (5)	0.0257 (5)	0.0036 (4)	0.0006 (4)	0.0048 (4)
C10B	0.0194 (5)	0.0223 (5)	0.0244 (5)	0.0040 (4)	0.0022 (4)	0.0001 (4)
C11B	0.0200 (4)	0.0226 (5)	0.0189 (4)	0.0013 (4)	0.0038 (3)	0.0017 (4)
C12B	0.0182 (4)	0.0165 (4)	0.0158 (4)	−0.0016 (4)	0.0010 (3)	0.0018 (3)

Geometric parameters (Å, º)

O1A—C1A	1.2491 (12)	O1B—C1B	1.2493 (14)
O2A—C1A	1.2528 (13)	O2B—C1B	1.2554 (13)
N1A—C6A	1.5072 (14)	N1B—C6B	1.5013 (13)
N1A—C5A	1.5077 (14)	N1B—C5B	1.5104 (14)
N1A—C2A	1.5120 (12)	N1B—C2B	1.5146 (13)
N1A—H1A	0.9300	N1B—H1B	0.9300
C1A—C2A	1.5443 (15)	C1B—C2B	1.5427 (14)
C2A—C3A	1.5329 (14)	C2B—C3B	1.5351 (15)
C2A—H2A	1.0000	C2B—H2B	1.0000
C3A—C4A	1.5246 (15)	C3B—C4B	1.5255 (18)
C3A—H3A	0.9900	C3B—H3D	0.9900
C3A—H3B	0.9900	C3B—H3C	0.9900
C4A—C5A	1.5162 (17)	C4B—C5B	1.5116 (19)
C4A—H4A	0.9900	C4B—H4C	0.9900
C4A—H4B	0.9900	C4B—H4D	0.9900
C5A—H5A	0.9900	C5B—H5C	0.9900
C5A—H5B	0.9900	C5B—H5D	0.9900
C6A—C7A	1.5026 (15)	C6B—C7B	1.5065 (15)
C6A—H6A	0.9900	C6B—H6C	0.9900
C6A—H6B	0.9900	C6B—H6D	0.9900
C7A—C8A	1.3945 (15)	C7B—C8B	1.3950 (16)
C7A—C12A	1.3985 (15)	C7B—C12B	1.3963 (14)
C8A—C9A	1.3955 (17)	C8B—C9B	1.3906 (17)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.391 (2)	C9B—C10B	1.3935 (18)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—C11A	1.3901 (19)	C10B—C11B	1.3917 (18)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.3935 (17)	C11B—C12B	1.3912 (16)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—H12A	0.9500	C12B—H12B	0.9500
C6A—N1A—C5A	111.21 (9)	C6B—N1B—C5B	112.49 (8)
C6A—N1A—C2A	115.38 (7)	C6B—N1B—C2B	114.30 (8)
C5A—N1A—C2A	107.48 (8)	C5B—N1B—C2B	107.69 (8)
C6A—N1A—H1A	107.5	C6B—N1B—H1B	107.3
C5A—N1A—H1A	107.5	C5B—N1B—H1B	107.3
C2A—N1A—H1A	107.5	C2B—N1B—H1B	107.3
O1A—C1A—O2A	128.04 (10)	O1B—C1B—O2B	128.25 (10)
O1A—C1A—C2A	115.29 (9)	O1B—C1B—C2B	114.84 (9)
O2A—C1A—C2A	116.67 (9)	O2B—C1B—C2B	116.91 (10)
N1A—C2A—C3A	104.85 (8)	N1B—C2B—C3B	105.00 (8)
N1A—C2A—C1A	107.99 (8)	N1B—C2B—C1B	109.08 (8)
C3A—C2A—C1A	112.87 (8)	C3B—C2B—C1B	113.13 (8)
N1A—C2A—H2A	110.3	N1B—C2B—H2B	109.8
C3A—C2A—H2A	110.3	C3B—C2B—H2B	109.8
C1A—C2A—H2A	110.3	C1B—C2B—H2B	109.8
C4A—C3A—C2A	103.64 (8)	C4B—C3B—C2B	103.55 (9)
C4A—C3A—H3A	111.0	C4B—C3B—H3D	111.1
C2A—C3A—H3A	111.0	C2B—C3B—H3D	111.1
C4A—C3A—H3B	111.0	C4B—C3B—H3C	111.1
C2A—C3A—H3B	111.0	C2B—C3B—H3C	111.1
H3A—C3A—H3B	109.0	H3D—C3B—H3C	109.0
C5A—C4A—C3A	101.82 (9)	C5B—C4B—C3B	102.68 (9)
C5A—C4A—H4A	111.4	C5B—C4B—H4C	111.2
C3A—C4A—H4A	111.4	C3B—C4B—H4C	111.2
C5A—C4A—H4B	111.4	C5B—C4B—H4D	111.2
C3A—C4A—H4B	111.4	C3B—C4B—H4D	111.2
H4A—C4A—H4B	109.3	H4C—C4B—H4D	109.1
N1A—C5A—C4A	104.41 (8)	N1B—C5B—C4B	103.65 (9)
N1A—C5A—H5A	110.9	N1B—C5B—H5C	111.0
C4A—C5A—H5A	110.9	C4B—C5B—H5C	111.0
N1A—C5A—H5B	110.9	N1B—C5B—H5D	111.0
C4A—C5A—H5B	110.9	C4B—C5B—H5D	111.0
H5A—C5A—H5B	108.9	H5C—C5B—H5D	109.0
C7A—C6A—N1A	112.23 (8)	N1B—C6B—C7B	111.39 (8)
C7A—C6A—H6A	109.2	N1B—C6B—H6C	109.4
N1A—C6A—H6A	109.2	C7B—C6B—H6C	109.4
C7A—C6A—H6B	109.2	N1B—C6B—H6D	109.4
N1A—C6A—H6B	109.2	C7B—C6B—H6D	109.4
H6A—C6A—H6B	107.9	H6C—C6B—H6D	108.0
C8A—C7A—C12A	119.51 (10)	C8B—C7B—C12B	119.33 (10)
C8A—C7A—C6A	120.37 (10)	C8B—C7B—C6B	120.87 (10)
C12A—C7A—C6A	120.11 (9)	C12B—C7B—C6B	119.78 (10)
C7A—C8A—C9A	120.28 (11)	C9B—C8B—C7B	120.44 (10)
C7A—C8A—H8A	119.9	C9B—C8B—H8B	119.8
C9A—C8A—H8A	119.9	C7B—C8B—H8B	119.8
C10A—C9A—C8A	120.10 (11)	C8B—C9B—C10B	119.97 (11)
C10A—C9A—H9A	119.9	C8B—C9B—H9B	120.0
C8A—C9A—H9A	119.9	C10B—C9B—H9B	120.0
C11A—C10A—C9A	119.70 (11)	C11B—C10B—C9B	119.86 (11)
C11A—C10A—H10A	120.2	C11B—C10B—H10B	120.1
C9A—C10A—H10A	120.2	C9B—C10B—H10B	120.1
C10A—C11A—C12A	120.52 (12)	C12B—C11B—C10B	120.13 (11)
C10A—C11A—H11A	119.7	C12B—C11B—H11B	119.9
C12A—C11A—H11A	119.7	C10B—C11B—H11B	119.9
C11A—C12A—C7A	119.89 (11)	C11B—C12B—C7B	120.27 (10)
C11A—C12A—H12A	120.1	C11B—C12B—H12B	119.9
C7A—C12A—H12A	120.1	C7B—C12B—H12B	119.9
C6A—N1A—C2A—C3A	120.72 (9)	C5B—N1B—C2B—C1B	120.39 (9)
C5A—N1A—C2A—C3A	−3.97 (11)	O1B—C1B—C2B—N1B	175.86 (9)
C6A—N1A—C2A—C1A	−118.70 (9)	O2B—C1B—C2B—N1B	−3.78 (13)
C5A—N1A—C2A—C1A	116.61 (10)	O1B—C1B—C2B—C3B	−67.67 (12)
O1A—C1A—C2A—N1A	174.07 (9)	O2B—C1B—C2B—C3B	112.68 (11)
O2A—C1A—C2A—N1A	−6.66 (13)	N1B—C2B—C3B—C4B	25.53 (10)
O1A—C1A—C2A—C3A	−70.50 (12)	C1B—C2B—C3B—C4B	−93.32 (10)
O2A—C1A—C2A—C3A	108.76 (11)	C2B—C3B—C4B—C5B	−40.42 (10)
N1A—C2A—C3A—C4A	28.12 (10)	C6B—N1B—C5B—C4B	−150.76 (9)
C1A—C2A—C3A—C4A	−89.17 (10)	C2B—N1B—C5B—C4B	−23.91 (11)
C2A—C3A—C4A—C5A	−41.36 (11)	C3B—C4B—C5B—N1B	39.58 (11)
C6A—N1A—C5A—C4A	−149.03 (10)	C5B—N1B—C6B—C7B	−173.70 (8)
C2A—N1A—C5A—C4A	−21.85 (12)	C2B—N1B—C6B—C7B	63.07 (10)
C3A—C4A—C5A—N1A	38.89 (12)	N1B—C6B—C7B—C8B	−100.93 (11)
C5A—N1A—C6A—C7A	−173.23 (9)	N1B—C6B—C7B—C12B	77.58 (12)
C2A—N1A—C6A—C7A	64.04 (11)	C12B—C7B—C8B—C9B	−0.40 (16)
N1A—C6A—C7A—C8A	−95.18 (11)	C6B—C7B—C8B—C9B	178.12 (10)
N1A—C6A—C7A—C12A	86.06 (11)	C7B—C8B—C9B—C10B	0.33 (18)
C12A—C7A—C8A—C9A	−0.14 (16)	C8B—C9B—C10B—C11B	0.12 (18)
C6A—C7A—C8A—C9A	−178.91 (10)	C9B—C10B—C11B—C12B	−0.50 (18)
C7A—C8A—C9A—C10A	0.93 (18)	C10B—C11B—C12B—C7B	0.43 (17)
C8A—C9A—C10A—C11A	−1.18 (19)	C8B—C7B—C12B—C11B	0.02 (16)
C9A—C10A—C11A—C12A	0.66 (19)	C6B—C7B—C12B—C11B	−178.52 (10)
C10A—C11A—C12A—C7A	0.12 (18)	C2A—N1A—C6A—C7A	64.04 (11)
C8A—C7A—C12A—C11A	−0.38 (16)	C1A—C2A—N1A—C6A	−118.70 (9)
C6A—C7A—C12A—C11A	178.39 (10)	C2B—N1B—C6B—C7B	63.07 (10)
C6B—N1B—C2B—C3B	124.63 (8)	C1B—C2B—N1B—C6B	−113.83 (9)
C5B—N1B—C2B—C3B	−1.15 (10)	C2A—N1A—C6A—C7A	64.04 (11)
C6B—N1B—C2B—C1B	−113.83 (9)	C2B—N1B—C6B—C7B	63.07 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O1B^i	0.93	2.31	2.8945 (13)	120
N1A—H1A···O2A	0.93	2.02	2.5973 (13)	119
N1B—H1B···O2B	0.93	2.05	2.6259 (12)	118
C2B—H2B···O1A^ii	1.00	2.51	3.2649 (13)	132
C6A—H6A···O2B	0.99	2.45	3.1520 (14)	127
C6A—H6B···O1A^iii	0.99	2.29	3.2506 (14)	164
C5B—H5D···O2A^i	0.99	2.29	3.0796 (14)	136
C6B—H6C···O1A^ii	0.99	2.36	3.2221 (14)	145
C8B—H8B···O1A^ii	0.95	2.54	3.3721 (14)	146
C12B—H12B···O1B^i	0.95	2.43	3.2438 (15)	143

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