3-(3,5-Di-tert-butyl-4-hydroxy­phen­yl)propionohydrazide

The structure of the title compound, C₁₇H₂₈N₂O₂, exhibits an elaborate network of N—H...N, N—H...O and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.084
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

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Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10    -   C13     ..       7.54 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C12     ..       5.99 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C16     ..       6.52 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C17     ..       5.89 su
PLAT414_ALERT_2_C Short Intra D-H..H-X       H121   ..  H201    ..       1.94 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H132   ..  H201    ..       1.91 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionohydrazide

Crystal data

C17H28N2O2	F(000) = 640.00
Mr = 292.42	Dx = 1.125 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 12611 reflections
a = 6.1848 (16) Å	θ = 3.3–27.5°
b = 14.685 (5) Å	µ = 0.07 mm^−1
c = 19.097 (5) Å	T = 296 K
β = 95.439 (10)°	Plate, colorless
V = 1726.7 (9) Å^3	0.23 × 0.20 × 0.11 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2380 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.039
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→8
Tmin = 0.934, Tmax = 0.992	k = −19→19
16372 measured reflections	l = −24→24
3890 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0001Fo^2 + 1.09σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.041	(Δ/σ)max < 0.001
wR(F^2) = 0.084	Δρmax = 0.31 e Å^−3
S = 1.00	Δρmin = −0.22 e Å^−3
3890 reflections	Extinction correction: Larson (1970)
191 parameters	Extinction coefficient: 194 (28)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O21	0.05120 (14)	0.17108 (6)	0.11258 (4)	0.0506 (3)
O22	0.96705 (13)	0.34707 (6)	0.46279 (4)	0.0484 (3)
N31	0.68178 (16)	0.44093 (8)	0.46528 (5)	0.0374 (3)
N32	0.75036 (16)	0.48027 (9)	0.53162 (5)	0.0418 (3)
C1	0.34858 (19)	0.31493 (10)	0.28267 (6)	0.0351 (3)
C2	0.38203 (19)	0.34090 (10)	0.21495 (6)	0.0376 (3)
C3	0.2896 (2)	0.29498 (10)	0.15553 (6)	0.0352 (3)
C4	0.1577 (2)	0.22011 (9)	0.16701 (6)	0.0355 (3)
C5	0.12265 (19)	0.18928 (9)	0.23515 (6)	0.0347 (3)
C6	0.2207 (2)	0.23937 (10)	0.29144 (6)	0.0369 (3)
C7	0.45079 (19)	0.36615 (10)	0.34582 (6)	0.0385 (3)
C8	0.67435 (19)	0.32972 (10)	0.37202 (6)	0.0359 (3)
C9	0.78693 (19)	0.37347 (9)	0.43707 (6)	0.0333 (3)
C10	0.3348 (2)	0.32670 (11)	0.08107 (6)	0.0435 (4)
C11	0.4937 (2)	0.40704 (12)	0.08444 (8)	0.0675 (5)
C12	0.1253 (2)	0.35984 (12)	0.03913 (6)	0.0605 (5)
C13	0.4419 (2)	0.24970 (12)	0.04178 (6)	0.0588 (5)
C14	−0.0149 (2)	0.10498 (10)	0.24774 (6)	0.0398 (3)
C15	−0.2522 (2)	0.12080 (11)	0.21913 (8)	0.0528 (4)
C16	0.0775 (2)	0.02047 (11)	0.21376 (8)	0.0536 (4)
C17	−0.0137 (2)	0.08291 (12)	0.32654 (6)	0.0602 (5)
H201	0.0686	0.1893	0.0721	0.061*
H2	0.4748	0.3938	0.2085	0.044*
H6	0.1976	0.2203	0.3393	0.044*
H71	0.3569	0.3610	0.3835	0.046*
H72	0.4646	0.4297	0.3332	0.045*
H81	0.7673	0.3374	0.3343	0.044*
H82	0.6587	0.2654	0.3818	0.043*
H111	0.6274	0.3892	0.1104	0.082*
H112	0.4326	0.4578	0.1074	0.082*
H113	0.5213	0.4243	0.0376	0.082*
H121	0.0237	0.3104	0.0335	0.073*
H122	0.1574	0.3810	−0.0063	0.072*
H123	0.0634	0.4087	0.0640	0.073*
H131	0.4594	0.2687	−0.0054	0.071*
H132	0.3515	0.1965	0.0406	0.072*
H133	0.5815	0.2358	0.0658	0.072*
H151	−0.3059	0.1745	0.2404	0.064*
H152	−0.2613	0.1286	0.1690	0.064*
H153	−0.3379	0.0692	0.2303	0.064*
H161	0.0770	0.0303	0.1640	0.065*
H162	−0.0101	−0.0317	0.2221	0.065*
H163	0.2237	0.0101	0.2338	0.065*
H171	−0.0745	0.1332	0.3502	0.073*
H172	−0.0988	0.0292	0.3324	0.073*
H173	0.1329	0.0727	0.3462	0.073*
H301	0.5498	0.4602	0.4499	0.044*
H302	0.8311	0.4340	0.5585	0.051*
H303	0.8419	0.5262	0.5257	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O21	0.0654 (6)	0.0575 (7)	0.0276 (4)	−0.0215 (5)	−0.0019 (4)	−0.0066 (4)
O22	0.0437 (5)	0.0569 (7)	0.0422 (5)	0.0127 (5)	−0.0094 (4)	−0.0072 (4)
N31	0.0340 (5)	0.0457 (7)	0.0307 (5)	0.0033 (5)	−0.0056 (4)	−0.0111 (5)
N32	0.0406 (6)	0.0494 (8)	0.0337 (5)	0.0014 (5)	−0.0054 (4)	−0.0140 (5)
C1	0.0339 (6)	0.0386 (8)	0.0316 (6)	0.0040 (6)	−0.0036 (5)	−0.0082 (5)
C2	0.0386 (7)	0.0365 (8)	0.0369 (7)	−0.0043 (6)	−0.0006 (5)	−0.0044 (6)
C3	0.0374 (7)	0.0382 (8)	0.0296 (6)	0.0002 (6)	0.0013 (5)	−0.0029 (5)
C4	0.0367 (6)	0.0402 (8)	0.0282 (6)	−0.0007 (6)	−0.0036 (5)	−0.0083 (5)
C5	0.0350 (6)	0.0361 (8)	0.0325 (6)	0.0010 (6)	−0.0003 (5)	−0.0040 (5)
C6	0.0397 (7)	0.0431 (9)	0.0271 (6)	0.0026 (6)	−0.0002 (5)	−0.0028 (5)
C7	0.0412 (7)	0.0402 (9)	0.0329 (6)	0.0003 (6)	−0.0037 (5)	−0.0090 (6)
C8	0.0418 (7)	0.0367 (8)	0.0289 (6)	−0.0016 (6)	0.0014 (5)	−0.0048 (5)
C9	0.0359 (7)	0.0359 (8)	0.0280 (6)	−0.0010 (6)	0.0029 (5)	0.0019 (5)
C10	0.0513 (8)	0.0482 (9)	0.0316 (6)	−0.0048 (7)	0.0066 (5)	−0.0019 (6)
C11	0.0855 (12)	0.0710 (13)	0.0482 (9)	−0.0262 (10)	0.0181 (8)	0.0020 (8)
C12	0.0780 (11)	0.0614 (12)	0.0410 (8)	0.0058 (9)	0.0001 (7)	0.0067 (8)
C13	0.0611 (9)	0.0747 (12)	0.0426 (8)	−0.0013 (9)	0.0152 (7)	−0.0067 (8)
C14	0.0445 (7)	0.0384 (8)	0.0365 (6)	−0.0026 (6)	0.0033 (5)	−0.0031 (6)
C15	0.0440 (8)	0.0534 (10)	0.0616 (9)	−0.0063 (7)	0.0080 (6)	−0.0068 (8)
C16	0.0574 (9)	0.0419 (9)	0.0614 (9)	−0.0003 (7)	0.0049 (7)	−0.0037 (7)
C17	0.0799 (11)	0.0537 (11)	0.0478 (8)	−0.0148 (9)	0.0113 (7)	0.0040 (7)

Geometric parameters (Å, º)

O21—C4	1.3794 (14)	C2—H2	0.980
O22—C9	1.2365 (14)	C6—H6	0.980
N31—N32	1.4202 (14)	C7—H71	0.970
N31—C9	1.3270 (16)	C7—H72	0.970
C1—C2	1.3826 (16)	C8—H81	0.970
C1—C6	1.3821 (19)	C8—H82	0.970
C1—C7	1.5084 (17)	C11—H111	0.960
C2—C3	1.3951 (17)	C11—H112	0.960
C3—C4	1.3987 (19)	C11—H113	0.960
C3—C10	1.5468 (17)	C12—H121	0.960
C4—C5	1.4138 (16)	C12—H122	0.960
C5—C6	1.3930 (16)	C12—H123	0.960
C5—C14	1.5339 (19)	C13—H131	0.960
C7—C8	1.5222 (16)	C13—H132	0.960
C8—C9	1.5089 (16)	C13—H133	0.960
C10—C11	1.533 (2)	C15—H151	0.960
C10—C12	1.5366 (19)	C15—H152	0.960
C10—C13	1.541 (2)	C15—H153	0.960
C14—C15	1.5343 (18)	C16—H161	0.960
C14—C16	1.536 (2)	C16—H162	0.960
C14—C17	1.5387 (19)	C16—H163	0.960
O21—H201	0.835	C17—H171	0.960
N31—H301	0.887	C17—H172	0.960
N32—H302	0.963	C17—H173	0.960
N32—H303	0.894
O21···O22^i	2.8710 (10)	H113···H112^xii	3.302
O21···N32^i	3.2011 (14)	H113···H113^xii	2.647
O22···O21^ii	2.8710 (10)	H113···H121^ix	3.536
O22···N32^iii	3.0756 (15)	H113···H122^xii	3.565
O22···C12^ii	3.4706 (19)	H113···H123^ix	3.351
O22···C13^ii	3.4757 (17)	H121···O22^i	2.684
N31···N31^iv	3.2233 (15)	H121···C9^i	3.509
N31···N32^iv	2.9182 (14)	H121···H111^vii	3.191
N31···C13^v	3.547 (2)	H121···H113^vii	3.536
N32···O21^ii	3.2011 (14)	H121···H131^vii	3.552
N32···O22^iii	3.0756 (15)	H121···H133^vii	3.062
N32···N31^iv	2.9182 (14)	H121···H171^vi	3.594
N32···N32^iv	3.2674 (13)	H122···O22^i	3.580
N32···N32^iii	3.4694 (14)	H122···C17^vi	3.309
N32···C7^iv	3.5585 (17)	H122···H6^vi	3.332
N32···C9^iii	3.5827 (16)	H122···H113^xii	3.565
C7···N32^iv	3.5587 (17)	H122···H123^xiv	3.513
C9···N32^iii	3.5827 (16)	H122···H171^vi	2.978
C9···C13^v	3.554 (2)	H122···H172^vi	3.580
C12···O22^i	3.4706 (19)	H122···H173^vi	2.887
C13···O22^i	3.4754 (17)	H123···C11^vii	3.581
C13···N31^vi	3.547 (2)	H123···C17^xi	3.336
C13···C9^vi	3.554 (2)	H123···H111^vii	2.931
O21···H133^vii	3.106	H123···H113^vii	3.351
O21···H302^i	2.243	H123···H122^xiv	3.513
O21···H303^viii	3.503	H123···H172^xi	2.648
O21···H303^i	3.523	H123···H173^xi	3.256
O22···H6^ix	3.419	H131···O22^i	3.491
O22···H71^ix	2.973	H131···N31^vi	3.440
O22···H121^ii	2.684	H131···C7^vi	3.459
O22···H122^ii	3.580	H131···C8^vi	3.150
O22···H131^ii	3.491	H131···C9^vi	3.177
O22···H132^ii	2.757	H131···H301^vi	3.526
O22···H133^v	3.453	H131···H6^vi	3.244
O22···H302^iii	3.487	H131···H71^vi	2.877
O22···H303^iii	2.204	H131···H82^vi	2.629
N31···H201^ii	3.552	H131···H121^ix	3.552
N31···H301^iv	2.688	H132···O22^i	2.757
N31···H131^v	3.440	H132···N31^vi	3.298
N31···H132^v	3.298	H132···N32^viii	3.495
N31···H133^v	3.321	H132···N32^vi	3.596
N31···H161^x	3.278	H132···H301^viii	3.525
N31···H302^iii	3.594	H132···H301^vi	3.194
N31···H303^iv	3.295	H132···H71^vi	3.120
N31···H303^iii	2.974	H132···H152^ix	3.410
N32···H301^iv	2.112	H132···H302^vi	3.520
N32···H71^iv	2.950	H132···H303^viii	3.000
N32···H72^iv	3.292	H133···O21^ix	3.106
N32···H132^x	3.495	H133···O22^vi	3.453
N32···H132^v	3.596	H133···N31^vi	3.321
N32···H133^v	3.422	H133···N32^vi	3.422
N32···H152^ii	3.079	H133···C9^vi	3.289
N32···H161^ii	3.087	H133···C15^ix	3.452
N32···H201^ii	3.222	H133···H82^vi	3.590
N32···H302^iii	3.478	H133···H121^ix	3.062
N32···H303^iii	2.844	H133···H151^ix	3.461
C1···H151^ix	3.131	H133···H152^ix	2.637
C1···H162^xi	3.071	H133···H201^ix	3.080
C2···H151^ix	3.123	H133···H302^vi	2.943
C2···H153^xi	3.530	H151···C1^vii	3.131
C2···H162^xi	3.281	H151···C2^vii	3.123
C2···H163^x	3.554	H151···C3^vii	3.354
C2···H172^xi	3.352	H151···C4^vii	3.541
C3···H151^ix	3.354	H151···C5^vii	3.533
C4···H151^ix	3.541	H151···C6^vii	3.313
C4···H302^i	3.563	H151···C8^vii	3.405
C5···H151^ix	3.533	H151···H2^vii	3.525
C6···H81^vii	3.322	H151···H81^vii	2.999
C6···H151^ix	3.313	H151···H82^vii	3.040
C7···H131^v	3.459	H151···H133^vii	3.461
C7···H153^xi	3.362	H152···N32^i	3.079
C7···H162^xi	3.270	H152···C13^vii	3.405
C7···H163^x	3.379	H152···H72^xiii	3.178
C7···H303^iv	3.555	H152···H132^vii	3.410
C8···H131^v	3.150	H152···H133^vii	2.637
C8···H151^ix	3.405	H152···H302^i	2.419
C8···H161^x	3.422	H153···C2^xiii	3.530
C8···H162^x	3.520	H153···C7^xiii	3.362
C8···H163^x	3.427	H153···H2^xiii	2.985
C8···H171^ix	3.323	H153···H72^xiii	2.470
C9···H121^ii	3.509	H153···H163^vii	2.854
C9···H131^v	3.177	H153···H302^i	3.536
C9···H133^v	3.289	H161···N31^viii	3.278
C9···H161^x	3.170	H161···N32^i	3.087
C9···H201^ii	3.111	H161···C8^viii	3.422
C9···H303^iii	2.764	H161···C9^viii	3.170
C11···H113^xii	3.397	H161···H301^viii	3.475
C11···H123^ix	3.581	H161···H72^viii	3.192
C11···H172^xi	3.528	H161···H81^viii	2.991
C11···H173^x	3.525	H161···H302^i	2.463
C12···H111^vii	3.509	H161···H303^i	3.009
C12···H172^xi	3.509	H162···C1^xiii	3.071
C13···H71^vi	3.428	H162···C2^xiii	3.281
C13···H82^vi	3.458	H162···C7^xiii	3.270
C13···H152^ix	3.405	H162···C8^viii	3.520
C15···H72^xiii	3.217	H162···H2^xiii	3.456
C15···H133^vii	3.452	H162···H71^xiii	3.214
C15···H302^i	3.258	H162···H72^xiii	2.962
C16···H2^viii	3.543	H162···H81^viii	2.723
C16···H72^viii	3.328	H162···H302^i	3.492
C16···H81^viii	3.026	H163···C2^viii	3.554
C16···H302^i	3.271	H163···C7^viii	3.379
C17···H82^vii	3.578	H163···C8^viii	3.427
C17···H112^xiii	3.507	H163···H2^viii	2.687
C17···H122^v	3.309	H163···H72^viii	2.686
C17···H123^xiii	3.336	H163···H81^viii	2.854
H301···N31^iv	2.688	H163···H111^viii	3.512
H301···N32^iv	2.112	H163···H153^ix	2.854
H301···H301^iv	2.374	H171···C8^vii	3.323
H301···H131^v	3.525	H171···H81^vii	3.160
H301···H132^x	3.525	H171···H82^vii	2.654
H301···H132^v	3.194	H171···H112^xiii	3.541
H301···H161^x	3.475	H171···H121^v	3.594
H301···H302^iv	2.814	H171···H122^v	2.978
H301···H303^iv	2.518	H172···C2^xiii	3.352
H2···C16^x	3.543	H172···C11^xiii	3.528
H2···H151^ix	3.525	H172···C12^xiii	3.509
H2···H153^xi	2.985	H172···H2^xiii	3.104
H2···H162^xi	3.456	H172···H112^xiii	2.671
H2···H163^x	2.687	H172···H122^v	3.580
H2···H172^xi	3.104	H172···H123^xiii	2.648
H6···O22^vii	3.419	H173···C11^viii	3.525
H6···H81^vii	3.162	H173···H111^viii	3.148
H6···H82^vii	3.566	H173···H112^viii	3.225
H6···H122^v	3.332	H173···H122^v	2.887
H6···H131^v	3.244	H173···H123^xiii	3.256
H71···O22^vii	2.973	H201···O22^i	2.188
H71···N32^iv	2.950	H201···N31^i	3.552
H71···C13^v	3.428	H201···N32^i	3.222
H71···H131^v	2.877	H201···C9^i	3.111
H71···H132^v	3.120	H201···H133^vii	3.080
H71···H162^xi	3.214	H201···H302^i	2.330
H71···H302^iv	3.447	H201···H303^viii	3.119
H71···H303^iv	2.768	H201···H303^i	3.540
H72···N32^iv	3.292	H302···O21^ii	2.243
H72···C15^xi	3.217	H302···O22^iii	3.487
H72···C16^x	3.328	H302···N31^iii	3.594
H72···H152^xi	3.178	H302···N32^iii	3.478
H72···H153^xi	2.470	H302···C4^ii	3.563
H72···H161^x	3.192	H302···C15^ii	3.258
H72···H162^xi	2.962	H302···C16^ii	3.271
H72···H163^x	2.686	H302···H301^iv	2.814
H72···H302^iv	3.514	H302···H71^iv	3.447
H72···H303^iv	3.499	H302···H72^iv	3.514
H81···C6^ix	3.322	H302···H132^v	3.520
H81···C16^x	3.026	H302···H133^v	2.943
H81···H6^ix	3.162	H302···H152^ii	2.419
H81···H151^ix	2.999	H302···H153^ii	3.536
H81···H161^x	2.991	H302···H161^ii	2.463
H81···H162^x	2.723	H302···H162^ii	3.492
H81···H163^x	2.854	H302···H201^ii	2.330
H81···H171^ix	3.160	H302···H303^iii	2.764
H82···C13^v	3.458	H303···O21^x	3.503
H82···C17^ix	3.578	H303···O21^ii	3.523
H82···H6^ix	3.566	H303···O22^iii	2.204
H82···H131^v	2.629	H303···N31^iv	3.295
H82···H133^v	3.590	H303···N31^iii	2.974
H82···H151^ix	3.040	H303···N32^iii	2.844
H82···H171^ix	2.654	H303···C7^iv	3.555
H111···C12^ix	3.509	H303···C9^iii	2.764
H111···H121^ix	3.191	H303···H301^iv	2.518
H111···H123^ix	2.931	H303···H71^iv	2.768
H111···H163^x	3.512	H303···H72^iv	3.499
H111···H173^x	3.148	H303···H132^x	3.000
H112···C17^xi	3.507	H303···H161^ii	3.009
H112···H113^xii	3.302	H303···H201^x	3.119
H112···H171^xi	3.541	H303···H201^ii	3.536
H112···H172^xi	2.671	H303···H302^iii	2.764
H112···H173^x	3.225	H303···H303^iii	2.397
H113···C11^xii	3.397
N32—N31—C9	123.33 (9)	C8—C7—H71	108.5
C2—C1—C6	118.22 (11)	C8—C7—H72	108.7
C2—C1—C7	121.45 (12)	H71—C7—H72	109.5
C6—C1—C7	120.32 (10)	C7—C8—H81	107.4
C1—C2—C3	122.78 (12)	C7—C8—H82	107.6
C2—C3—C4	116.91 (11)	C9—C8—H81	107.6
C2—C3—C10	120.42 (12)	C9—C8—H82	107.6
C4—C3—C10	122.67 (10)	H81—C8—H82	109.5
O21—C4—C3	122.42 (10)	C10—C11—H111	109.2
O21—C4—C5	115.00 (10)	C10—C11—H112	109.7
C3—C4—C5	122.59 (10)	C10—C11—H113	109.5
C4—C5—C6	116.60 (11)	H111—C11—H112	109.5
C4—C5—C14	122.57 (10)	H111—C11—H113	109.5
C6—C5—C14	120.83 (10)	H112—C11—H113	109.5
C1—C6—C5	122.86 (11)	C10—C12—H121	109.2
C1—C7—C8	112.73 (11)	C10—C12—H122	109.7
C7—C8—C9	117.06 (11)	C10—C12—H123	109.5
O22—C9—N31	122.04 (10)	H121—C12—H122	109.5
O22—C9—C8	121.44 (11)	H121—C12—H123	109.5
N31—C9—C8	116.52 (10)	H122—C12—H123	109.5
C3—C10—C11	111.36 (10)	C10—C13—H131	109.6
C3—C10—C12	110.95 (11)	C10—C13—H132	109.4
C3—C10—C13	110.50 (12)	C10—C13—H133	109.4
C11—C10—C12	106.49 (12)	H131—C13—H132	109.5
C11—C10—C13	106.36 (12)	H131—C13—H133	109.5
C12—C10—C13	111.03 (10)	H132—C13—H133	109.5
C5—C14—C15	110.36 (11)	C14—C15—H151	109.4
C5—C14—C16	110.60 (11)	C14—C15—H152	109.7
C5—C14—C17	111.84 (11)	C14—C15—H153	109.3
C15—C14—C16	110.71 (11)	H151—C15—H152	109.5
C15—C14—C17	107.21 (11)	H151—C15—H153	109.5
C16—C14—C17	106.00 (12)	H152—C15—H153	109.5
C4—O21—H201	115.9	C14—C16—H161	109.3
N32—N31—H301	110.7	C14—C16—H162	109.7
C9—N31—H301	125.0	C14—C16—H163	109.5
N31—N32—H302	106.6	H161—C16—H162	109.5
N31—N32—H303	109.5	H161—C16—H163	109.5
H302—N32—H303	107.3	H162—C16—H163	109.5
C1—C2—H2	118.5	C14—C17—H171	109.4
C3—C2—H2	118.7	C14—C17—H172	109.6
C1—C6—H6	118.5	C14—C17—H173	109.4
C5—C6—H6	118.6	H171—C17—H172	109.5
C1—C7—H71	108.6	H171—C17—H173	109.5
C1—C7—H72	108.7	H172—C17—H173	109.5
N32—N31—C9—O22	−8.76 (19)	C10—C3—C4—O21	−2.58 (19)
N32—N31—C9—C8	170.71 (10)	C10—C3—C4—C5	177.73 (12)
C2—C1—C6—C5	−0.77 (19)	O21—C4—C5—C6	−177.52 (11)
C6—C1—C2—C3	1.03 (19)	O21—C4—C5—C14	2.70 (17)
C2—C1—C7—C8	−89.35 (15)	C3—C4—C5—C6	2.19 (18)
C7—C1—C2—C3	−179.93 (12)	C3—C4—C5—C14	−177.58 (12)
C6—C1—C7—C8	89.68 (14)	C4—C5—C6—C1	−0.78 (19)
C7—C1—C6—C5	−179.82 (11)	C4—C5—C14—C15	−64.61 (16)
C1—C2—C3—C4	0.30 (19)	C4—C5—C14—C16	58.24 (15)
C1—C2—C3—C10	−179.40 (12)	C4—C5—C14—C17	176.13 (12)
C2—C3—C4—O21	177.73 (11)	C6—C5—C14—C15	115.62 (13)
C2—C3—C4—C5	−1.96 (19)	C6—C5—C14—C16	−121.53 (13)
C2—C3—C10—C11	2.65 (18)	C6—C5—C14—C17	−3.63 (17)
C2—C3—C10—C12	−115.78 (14)	C14—C5—C6—C1	179.00 (12)
C2—C3—C10—C13	120.63 (13)	C1—C7—C8—C9	−177.34 (10)
C4—C3—C10—C11	−177.03 (12)	C7—C8—C9—O22	178.63 (11)
C4—C3—C10—C12	64.54 (17)	C7—C8—C9—N31	−0.84 (17)
C4—C3—C10—C13	−59.05 (16)

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x+1, −y+1/2, z+1/2; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) x, −y+1/2, z+1/2; (vi) x, −y+1/2, z−1/2; (vii) x−1, y, z; (viii) −x+1, y−1/2, −z+1/2; (ix) x+1, y, z; (x) −x+1, y+1/2, −z+1/2; (xi) −x, y+1/2, −z+1/2; (xii) −x+1, −y+1, −z; (xiii) −x, y−1/2, −z+1/2; (xiv) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H201···O22^i	0.84	2.19	2.8710 (10)	139
N31—H301···N32^iv	0.89	2.11	2.9182 (14)	151
N32—H302···O21^ii	0.96	2.24	3.2011 (18)	173
N32—H303···O22^iii	0.89	2.20	3.0756 (18)	164

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