The crystal structures of benzyl­ammonium phenyl­acetate and its hydrate

The crystal packing of benzyl­ammonium phenyl­acetate (1) and its hydrate (2) is governed by hydrogen bonds formed between the ammonium and acetate groups and the water mol­ecule of crystallization (in 2 only). The benzyl moieties for hydro­phobic layers with the aromatic rings adopting edge-to-face arrangements.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.103
• Data-to-parameter ratio = 13.7

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.075
• wR factor = 0.170
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT353_ALERT_3_C Long   N-H (N0.87,N1.01A)  N1       - H12      .       1.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8       ..O1       .       2.63 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.928 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report

Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full           ! Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0052 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     13.505 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.519 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         21 Report

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        72% Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006), CrystalExplorer17 (Turner et al., 2017); software used to prepare material for publication: PLATON (Spek, 2009), RPLUTO (CCDC, 2018).

Benzylammonium phenylacetate (1)

Crystal data

C7H10N^+·C8H7O2^−	F(000) = 1040
Mr = 243.29	Dx = 1.219 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.913 (2) Å	Cell parameters from 4302 reflections
b = 5.9021 (5) Å	θ = 3.5–25.4°
c = 19.0842 (16) Å	µ = 0.08 mm^−1
β = 114.692 (3)°	T = 100 K
V = 2651.9 (4) Å^3	Block, colourless
Z = 8	0.10 × 0.04 × 0.02 mm

Data collection

Bruker D8 Venture TXS diffractometer	2398 independent reflections
Radiation source: rotating anode (TXS), Bruker TXS	1800 reflections with I > 2σ(I)
Focusing mirrors monochromator	Rint = 0.092
Detector resolution: 7.4074 pixels mm^-1	θmax = 25.4°, θmin = 3.3°
mix of phi and ω scans	h = −30→30
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −7→7
Tmin = 0.651, Tmax = 0.971	l = −22→22
14421 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 1.6577P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2398 reflections	Δρmax = 0.17 e Å^−3
175 parameters	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. C-H: constr N-H: refall

Reflections affected by the beamstop or those of higher order and significant higher Fo² than Fc² (caused by X-ray mirror) have been omitted in the refinement.

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

	x	y	z	Uiso*/Ueq
O1	0.28279 (5)	−0.35459 (19)	0.41706 (7)	0.0205 (3)
O2	0.24772 (5)	−0.07061 (19)	0.33362 (7)	0.0214 (3)
N1	0.27388 (7)	0.8748 (3)	0.20667 (9)	0.0204 (4)
H11	0.2496 (9)	0.977 (4)	0.1667 (13)	0.040 (6)*
H12	0.2666 (8)	0.714 (4)	0.1867 (12)	0.035 (6)*
H13	0.2661 (10)	0.883 (4)	0.2511 (14)	0.048 (7)*
C1	0.27013 (7)	−0.1506 (3)	0.40169 (10)	0.0169 (4)
C2	0.28113 (7)	0.0118 (3)	0.46855 (10)	0.0190 (4)
H2A	0.2687	0.1656	0.4476	0.023*
H2B	0.2577	−0.0353	0.4958	0.023*
C3	0.34259 (7)	0.0220 (3)	0.52591 (10)	0.0186 (4)
C4	0.36866 (8)	−0.1595 (3)	0.57485 (10)	0.0223 (4)
H4	0.3476	−0.2937	0.5719	0.027*
C5	0.42493 (8)	−0.1460 (3)	0.62768 (11)	0.0266 (4)
H5	0.4421	−0.2705	0.6608	0.032*
C6	0.45623 (8)	0.0480 (3)	0.63248 (11)	0.0307 (5)
H6	0.4948	0.0573	0.6688	0.037*
C7	0.43098 (8)	0.2279 (3)	0.58411 (12)	0.0321 (5)
H7	0.4523	0.3611	0.5869	0.038*
C8	0.37457 (8)	0.2153 (3)	0.53139 (11)	0.0255 (4)
H8	0.3576	0.3407	0.4986	0.031*
C9	0.33454 (8)	0.9379 (3)	0.22888 (11)	0.0273 (5)
H9A	0.3411	1.0948	0.2491	0.033*
H9B	0.3428	0.9326	0.1828	0.033*
C10	0.37371 (7)	0.7794 (3)	0.28918 (10)	0.0220 (4)
C11	0.38860 (8)	0.8179 (3)	0.36684 (11)	0.0281 (5)
H11A	0.3763	0.9525	0.3826	0.034*
C12	0.42124 (8)	0.6622 (4)	0.42177 (11)	0.0354 (5)
H12A	0.4310	0.6898	0.4748	0.042*
C13	0.43957 (9)	0.4672 (4)	0.39950 (13)	0.0375 (5)
H13A	0.4614	0.3592	0.4371	0.045*
C14	0.42609 (8)	0.4292 (3)	0.32244 (13)	0.0357 (5)
H14	0.4394	0.2962	0.3072	0.043*
C15	0.39330 (8)	0.5841 (3)	0.26732 (12)	0.0296 (5)
H15	0.3841	0.5570	0.2144	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0266 (7)	0.0168 (7)	0.0177 (6)	0.0002 (5)	0.0089 (5)	0.0000 (5)
O2	0.0305 (7)	0.0202 (7)	0.0134 (6)	0.0023 (5)	0.0091 (5)	0.0006 (5)
N1	0.0279 (9)	0.0181 (9)	0.0150 (8)	0.0000 (7)	0.0089 (7)	0.0013 (7)
C1	0.0161 (9)	0.0203 (10)	0.0168 (9)	−0.0024 (7)	0.0093 (7)	−0.0017 (7)
C2	0.0233 (10)	0.0179 (9)	0.0177 (9)	0.0015 (7)	0.0104 (8)	0.0006 (7)
C3	0.0246 (10)	0.0200 (9)	0.0152 (9)	0.0000 (7)	0.0122 (8)	−0.0030 (7)
C4	0.0282 (10)	0.0225 (10)	0.0185 (9)	−0.0023 (8)	0.0119 (8)	−0.0019 (7)
C5	0.0301 (11)	0.0271 (10)	0.0219 (10)	0.0060 (8)	0.0102 (8)	0.0001 (8)
C6	0.0220 (10)	0.0371 (12)	0.0287 (11)	−0.0007 (9)	0.0064 (9)	−0.0081 (9)
C7	0.0290 (11)	0.0275 (11)	0.0393 (12)	−0.0081 (9)	0.0140 (10)	−0.0062 (9)
C8	0.0301 (11)	0.0197 (10)	0.0283 (11)	−0.0014 (8)	0.0138 (9)	−0.0005 (8)
C9	0.0283 (11)	0.0274 (11)	0.0263 (10)	−0.0026 (8)	0.0116 (9)	0.0046 (8)
C10	0.0200 (10)	0.0245 (10)	0.0232 (10)	−0.0038 (7)	0.0105 (8)	0.0019 (8)
C11	0.0233 (10)	0.0377 (12)	0.0260 (11)	−0.0018 (8)	0.0128 (9)	−0.0017 (9)
C12	0.0253 (11)	0.0591 (15)	0.0216 (10)	−0.0011 (10)	0.0097 (9)	0.0073 (10)
C13	0.0219 (11)	0.0422 (13)	0.0402 (13)	0.0006 (9)	0.0051 (10)	0.0176 (10)
C14	0.0222 (11)	0.0292 (11)	0.0481 (14)	0.0001 (8)	0.0073 (10)	−0.0029 (10)
C15	0.0246 (11)	0.0318 (11)	0.0299 (11)	−0.0029 (8)	0.0090 (9)	−0.0037 (9)

Geometric parameters (Å, º)

O1—C1	1.250 (2)	C7—C8	1.388 (3)
O2—C1	1.272 (2)	C7—H7	0.9500
N1—C9	1.494 (2)	C8—H8	0.9500
N1—H11	0.97 (2)	C9—C10	1.501 (3)
N1—H12	1.01 (2)	C9—H9A	0.9900
N1—H13	0.95 (3)	C9—H9B	0.9900
C1—C2	1.525 (2)	C10—C11	1.385 (3)
C2—C3	1.511 (2)	C10—C15	1.392 (3)
C2—H2A	0.9900	C11—C12	1.385 (3)
C2—H2B	0.9900	C11—H11A	0.9500
C3—C8	1.388 (3)	C12—C13	1.378 (3)
C3—C4	1.396 (2)	C12—H12A	0.9500
C4—C5	1.386 (3)	C13—C14	1.381 (3)
C4—H4	0.9500	C13—H13A	0.9500
C5—C6	1.384 (3)	C14—C15	1.385 (3)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.379 (3)	C15—H15	0.9500
C6—H6	0.9500
C9—N1—H11	109.1 (13)	C8—C7—H7	119.8
C9—N1—H12	110.4 (11)	C7—C8—C3	120.88 (18)
H11—N1—H12	109.2 (17)	C7—C8—H8	119.6
C9—N1—H13	109.0 (14)	C3—C8—H8	119.6
H11—N1—H13	111.2 (19)	N1—C9—C10	110.87 (15)
H12—N1—H13	107.9 (17)	N1—C9—H9A	109.5
O1—C1—O2	124.09 (15)	C10—C9—H9A	109.5
O1—C1—C2	118.04 (15)	N1—C9—H9B	109.5
O2—C1—C2	117.86 (15)	C10—C9—H9B	109.5
C3—C2—C1	113.80 (14)	H9A—C9—H9B	108.1
C3—C2—H2A	108.8	C11—C10—C15	118.89 (17)
C1—C2—H2A	108.8	C11—C10—C9	120.98 (17)
C3—C2—H2B	108.8	C15—C10—C9	120.05 (17)
C1—C2—H2B	108.8	C12—C11—C10	120.66 (19)
H2A—C2—H2B	107.7	C12—C11—H11A	119.7
C8—C3—C4	118.27 (17)	C10—C11—H11A	119.7
C8—C3—C2	120.20 (16)	C13—C12—C11	120.06 (19)
C4—C3—C2	121.53 (16)	C13—C12—H12A	120.0
C5—C4—C3	120.69 (17)	C11—C12—H12A	120.0
C5—C4—H4	119.7	C12—C13—C14	119.87 (19)
C3—C4—H4	119.7	C12—C13—H13A	120.1
C6—C5—C4	120.34 (18)	C14—C13—H13A	120.1
C6—C5—H5	119.8	C13—C14—C15	120.2 (2)
C4—C5—H5	119.8	C13—C14—H14	119.9
C7—C6—C5	119.42 (18)	C15—C14—H14	119.9
C7—C6—H6	120.3	C14—C15—C10	120.26 (19)
C5—C6—H6	120.3	C14—C15—H15	119.9
C6—C7—C8	120.39 (18)	C10—C15—H15	119.9
C6—C7—H7	119.8
O1—C1—C2—C3	59.1 (2)	C2—C3—C8—C7	179.60 (17)
O2—C1—C2—C3	−122.12 (17)	N1—C9—C10—C11	−86.5 (2)
C1—C2—C3—C8	110.26 (18)	N1—C9—C10—C15	90.2 (2)
C1—C2—C3—C4	−70.2 (2)	C15—C10—C11—C12	−1.6 (3)
C8—C3—C4—C5	0.3 (2)	C9—C10—C11—C12	175.07 (17)
C2—C3—C4—C5	−179.29 (16)	C10—C11—C12—C13	0.4 (3)
C3—C4—C5—C6	−0.3 (3)	C11—C12—C13—C14	1.0 (3)
C4—C5—C6—C7	−0.1 (3)	C12—C13—C14—C15	−1.3 (3)
C5—C6—C7—C8	0.4 (3)	C13—C14—C15—C10	0.0 (3)
C6—C7—C8—C3	−0.4 (3)	C11—C10—C15—C14	1.4 (3)
C4—C3—C8—C7	0.0 (3)	C9—C10—C15—C14	−175.34 (18)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1^i	0.97 (2)	1.77 (2)	2.7177 (19)	165 (2)
N1—H12···O2^ii	1.01 (2)	1.73 (2)	2.7306 (19)	170.1 (18)
N1—H13···O2^iii	0.95 (3)	1.85 (3)	2.7938 (19)	174 (2)
C2—H2B···O1^iv	0.99	2.40	3.375 (2)	169
C8—H8···O1^iii	0.95	2.63	3.539 (2)	161
C9—H9···Cg1^v	0.95	2.92	3.877 (2)	163

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

Benzylammonium phenylacetate (2)

Crystal data

C7H10N^+·C8H7O2^−·H2O	F(000) = 560
Mr = 261.31	Dx = 1.227 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.8235 (7) Å	Cell parameters from 4619 reflections
b = 7.8766 (7) Å	θ = 2.7–25.0°
c = 26.364 (2) Å	µ = 0.09 mm^−1
β = 93.218 (3)°	T = 100 K
V = 1414.7 (2) Å^3	Block, colourless
Z = 4	0.10 × 0.06 × 0.04 mm

Data collection

Bruker D8 Venture TXS diffractometer	2461 independent reflections
Radiation source: rotating anode (TXS), Bruker TXS	2090 reflections with I > 2σ(I)
Focusing mirrors monochromator	Rint = 0.043
Detector resolution: 7.4074 pixels mm^-1	θmax = 25.0°, θmin = 3.5°
mix of phi and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −9→8
Tmin = 0.814, Tmax = 0.971	l = −31→27
7319 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.075	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.170	w = 1/[σ^2(Fo^2) + 3.8665P] where P = (Fo^2 + 2Fc^2)/3
S = 1.25	(Δ/σ)max < 0.001
2461 reflections	Δρmax = 0.30 e Å^−3
187 parameters	Δρmin = −0.27 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. C-H constr N-H and O-H: refxyz

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

	x	y	z	Uiso*/Ueq
O1	0.2350 (3)	0.5687 (3)	0.47484 (9)	0.0213 (6)
O2	0.4238 (4)	0.7897 (3)	0.45801 (10)	0.0245 (6)
O3	0.2403 (4)	0.0283 (3)	0.51346 (10)	0.0230 (6)
H32	0.296 (6)	−0.048 (6)	0.4981 (15)	0.028*
H31	0.355 (6)	0.089 (5)	0.5279 (15)	0.028*
N1	0.0153 (5)	0.2727 (4)	0.45885 (12)	0.0205 (7)
H11	0.091 (6)	0.364 (5)	0.4595 (14)	0.025*
H12	−0.084 (6)	0.296 (5)	0.4786 (15)	0.025*
H13	0.101 (6)	0.191 (5)	0.4742 (14)	0.025*
C1	0.3709 (5)	0.6394 (4)	0.45153 (13)	0.0174 (7)
C2	0.4705 (5)	0.5289 (5)	0.41280 (13)	0.0213 (8)
H2A	0.5366	0.4332	0.4311	0.026*
H2B	0.3676	0.4802	0.3892	0.026*
C3	0.6199 (5)	0.6182 (4)	0.38174 (13)	0.0190 (8)
C4	0.8017 (5)	0.6658 (4)	0.40418 (14)	0.0210 (8)
H4	0.8333	0.6385	0.4388	0.025*
C5	0.9377 (5)	0.7532 (5)	0.37627 (14)	0.0236 (8)
H5	1.0604	0.7860	0.3921	0.028*
C6	0.8942 (6)	0.7920 (5)	0.32577 (14)	0.0272 (9)
H6	0.9862	0.8522	0.3069	0.033*
C7	0.7154 (6)	0.7424 (5)	0.30294 (14)	0.0280 (9)
H7	0.6851	0.7674	0.2681	0.034*
C8	0.5802 (5)	0.6560 (5)	0.33093 (14)	0.0239 (8)
H8	0.4583	0.6223	0.3149	0.029*
C9	−0.0635 (5)	0.2271 (5)	0.40676 (13)	0.0226 (8)
H9A	−0.1605	0.3136	0.3947	0.027*
H9B	−0.1320	0.1165	0.4080	0.027*
C10	0.0974 (5)	0.2156 (4)	0.36952 (13)	0.0198 (8)
C11	0.0829 (6)	0.3063 (5)	0.32460 (14)	0.0253 (8)
H11A	−0.0272	0.3778	0.3174	0.030*
C12	0.2285 (6)	0.2938 (5)	0.28976 (14)	0.0330 (10)
H12A	0.2175	0.3567	0.2590	0.040*
C13	0.3896 (6)	0.1892 (5)	0.30013 (15)	0.0315 (10)
H13A	0.4887	0.1800	0.2764	0.038*
C14	0.4056 (6)	0.0986 (5)	0.34496 (14)	0.0273 (9)
H14	0.5164	0.0278	0.3521	0.033*
C15	0.2608 (5)	0.1105 (4)	0.37956 (14)	0.0222 (8)
H15	0.2722	0.0472	0.4102	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0211 (13)	0.0190 (13)	0.0243 (13)	−0.0042 (10)	0.0064 (10)	−0.0027 (11)
O2	0.0237 (14)	0.0181 (13)	0.0321 (15)	−0.0035 (11)	0.0068 (10)	−0.0066 (12)
O3	0.0200 (14)	0.0212 (14)	0.0279 (15)	−0.0001 (11)	0.0032 (10)	−0.0061 (12)
N1	0.0205 (16)	0.0160 (16)	0.0254 (17)	−0.0024 (13)	0.0050 (13)	−0.0044 (14)
C1	0.0122 (17)	0.0197 (18)	0.0201 (18)	−0.0014 (14)	−0.0011 (13)	−0.0014 (15)
C2	0.0248 (19)	0.0182 (18)	0.0213 (19)	−0.0018 (15)	0.0051 (14)	−0.0035 (15)
C3	0.0200 (18)	0.0145 (17)	0.0229 (19)	0.0030 (14)	0.0052 (14)	−0.0045 (15)
C4	0.0241 (19)	0.0192 (18)	0.0197 (18)	−0.0003 (15)	0.0020 (14)	−0.0012 (15)
C5	0.0208 (18)	0.0188 (19)	0.031 (2)	0.0001 (15)	0.0034 (15)	−0.0036 (16)
C6	0.029 (2)	0.025 (2)	0.029 (2)	−0.0042 (17)	0.0114 (16)	−0.0020 (17)
C7	0.032 (2)	0.031 (2)	0.0213 (19)	0.0023 (18)	0.0045 (15)	0.0034 (17)
C8	0.0175 (18)	0.030 (2)	0.024 (2)	−0.0029 (16)	0.0018 (14)	−0.0048 (17)
C9	0.0228 (19)	0.0222 (19)	0.0229 (19)	−0.0023 (15)	0.0019 (14)	−0.0030 (16)
C10	0.0242 (19)	0.0157 (17)	0.0195 (18)	−0.0086 (15)	0.0026 (14)	−0.0055 (15)
C11	0.030 (2)	0.025 (2)	0.0211 (19)	−0.0030 (16)	−0.0035 (15)	−0.0024 (16)
C12	0.046 (3)	0.035 (2)	0.0176 (19)	−0.011 (2)	0.0033 (17)	0.0000 (18)
C13	0.029 (2)	0.039 (2)	0.028 (2)	−0.0050 (18)	0.0110 (16)	−0.0072 (19)
C14	0.028 (2)	0.025 (2)	0.029 (2)	−0.0025 (16)	0.0054 (16)	−0.0052 (17)
C15	0.029 (2)	0.0142 (17)	0.0236 (19)	−0.0006 (15)	0.0046 (15)	−0.0017 (15)

Geometric parameters (Å, º)

O1—C1	1.270 (4)	C6—H6	0.9500
O2—C1	1.247 (4)	C7—C8	1.391 (5)
O3—H32	0.83 (4)	C7—H7	0.9500
O3—H31	0.97 (4)	C8—H8	0.9500
N1—C9	1.490 (4)	C9—C10	1.516 (5)
N1—H11	0.89 (4)	C9—H9A	0.9900
N1—H12	0.90 (4)	C9—H9B	0.9900
N1—H13	0.94 (4)	C10—C11	1.382 (5)
C1—C2	1.529 (5)	C10—C15	1.402 (5)
C2—C3	1.516 (5)	C11—C12	1.394 (5)
C2—H2A	0.9900	C11—H11A	0.9500
C2—H2B	0.9900	C12—C13	1.389 (6)
C3—C8	1.384 (5)	C12—H12A	0.9500
C3—C4	1.395 (5)	C13—C14	1.380 (6)
C4—C5	1.398 (5)	C13—H13A	0.9500
C4—H4	0.9500	C14—C15	1.385 (5)
C5—C6	1.382 (5)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.386 (5)
H32—O3—H31	100 (4)	C6—C7—H7	120.0
C9—N1—H11	113 (3)	C8—C7—H7	120.0
C9—N1—H12	110 (2)	C3—C8—C7	121.3 (3)
H11—N1—H12	106 (4)	C3—C8—H8	119.4
C9—N1—H13	114 (2)	C7—C8—H8	119.4
H11—N1—H13	102 (3)	N1—C9—C10	112.0 (3)
H12—N1—H13	111 (3)	N1—C9—H9A	109.2
O2—C1—O1	124.3 (3)	C10—C9—H9A	109.2
O2—C1—C2	119.7 (3)	N1—C9—H9B	109.2
O1—C1—C2	116.0 (3)	C10—C9—H9B	109.2
C3—C2—C1	115.7 (3)	H9A—C9—H9B	107.9
C3—C2—H2A	108.3	C11—C10—C15	119.0 (3)
C1—C2—H2A	108.3	C11—C10—C9	120.3 (3)
C3—C2—H2B	108.3	C15—C10—C9	120.7 (3)
C1—C2—H2B	108.3	C10—C11—C12	120.6 (4)
H2A—C2—H2B	107.4	C10—C11—H11A	119.7
C8—C3—C4	118.3 (3)	C12—C11—H11A	119.7
C8—C3—C2	121.5 (3)	C13—C12—C11	119.9 (4)
C4—C3—C2	120.3 (3)	C13—C12—H12A	120.1
C3—C4—C5	120.7 (3)	C11—C12—H12A	120.1
C3—C4—H4	119.7	C14—C13—C12	119.9 (4)
C5—C4—H4	119.7	C14—C13—H13A	120.0
C6—C5—C4	120.2 (3)	C12—C13—H13A	120.0
C6—C5—H5	119.9	C13—C14—C15	120.3 (4)
C4—C5—H5	119.9	C13—C14—H14	119.9
C5—C6—C7	119.5 (3)	C15—C14—H14	119.9
C5—C6—H6	120.3	C14—C15—C10	120.3 (3)
C7—C6—H6	120.3	C14—C15—H15	119.8
C6—C7—C8	120.1 (3)	C10—C15—H15	119.8
O2—C1—C2—C3	−4.5 (5)	C6—C7—C8—C3	0.2 (6)
O1—C1—C2—C3	174.7 (3)	N1—C9—C10—C11	−126.9 (4)
C1—C2—C3—C8	−107.2 (4)	N1—C9—C10—C15	54.4 (4)
C1—C2—C3—C4	72.2 (4)	C15—C10—C11—C12	0.0 (5)
C8—C3—C4—C5	1.6 (5)	C9—C10—C11—C12	−178.8 (3)
C2—C3—C4—C5	−177.8 (3)	C10—C11—C12—C13	0.1 (6)
C3—C4—C5—C6	−0.7 (5)	C11—C12—C13—C14	−0.3 (6)
C4—C5—C6—C7	−0.5 (6)	C12—C13—C14—C15	0.5 (6)
C5—C6—C7—C8	0.8 (6)	C13—C14—C15—C10	−0.5 (6)
C4—C3—C8—C7	−1.4 (5)	C11—C10—C15—C14	0.2 (5)
C2—C3—C8—C7	178.1 (3)	C9—C10—C15—C14	178.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H32···O2^i	0.83 (4)	1.90 (4)	2.728 (4)	175 (4)
O3—H31···O2^ii	0.97 (4)	1.81 (4)	2.771 (4)	169 (3)
N1—H11···O1	0.89 (4)	1.92 (4)	2.791 (4)	168 (4)
N1—H12···O1^iii	0.90 (4)	1.96 (4)	2.805 (4)	157 (4)
N1—H13···O3	0.94 (4)	1.87 (4)	2.809 (4)	170 (3)
C9—H9B···O3^iv	0.99	2.51	3.196 (4)	126
C15—H15···O2^i	0.95	2.57	3.412 (4)	147

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