Covalent-assisted supra­molecular synthesis: the effect of hydrogen bonding in cocrystals of 4-tert-butyl­benzoic acid with isoniazid and its derivatized forms

A series of cocrystals of isoniazid and four of its derivatives have been produced with the cocrystal former 4-tert-but­ylbenzoic acid via a one-pot covalent and supra­molecular synthesis, namely 4-tert-butyl­benzoic acid–isoniazid, C₆H₇N₃O·C₁₁H₁₄O₂, 4-tert-butyl­benzoic acid–N′-(propan-2-yl­idene)iso­nico­tino­hydra­zide, C₉H₁₁N₃O·C₁₁H₁₄O₂, 4-tert-butyl­benzoic acid–N′-(butan-2-yl­idene)iso­nico­tino­hydrazide, C₁₀H₁₃N₃O·C₁₁H₁₄O₂, 4-tert-butyl­benzoic acid–N′-(di­phenyl­methyl­idene)isonicotinohydrazide, C₁₉H₁₅N₃O·C₁₁H₁₄O₂, and 4-tert-butyl­benzoic acid–N′-(4-hy­droxy-4-methyl­pentan-2-yl­idene)isonico­tino­hydrazide, C₁₂H₁₇N₃O₂·C₁₁H₁₄O₂. The co-former falls under the classification of a `generally regarded as safe' compound. The four derivatizing ketones used are propan-2-one, butan-2-one, benzo­phenone and 3-hy­droxy-3-methyl­butan-2-one. Hydrogen bonds involving the carb­oxy­lic acid occur consistently with the pyridine ring N atom of the isoniazid and all of its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary based on the steric influences of the derivative group. These are contrasted in each of the mol­ecular systems.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus and XPREP (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

4-tert-Butylbenzoic acid–pyridine-4-carbohydrazide (1/1) (I)

Crystal data

C6H7N3O·C11H14O2	Z = 2
Mr = 315.37	F(000) = 336
Triclinic, P1	Dx = 1.262 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6076 (2) Å	Cell parameters from 5430 reflections
b = 7.6668 (2) Å	θ = 2.5–28.1°
c = 16.5297 (5) Å	µ = 0.09 mm^−1
α = 94.565 (2)°	T = 173 K
β = 93.480 (2)°	Blocks, colourless
γ = 94.758 (2)°	0.85 × 0.47 × 0.27 mm
V = 829.94 (4) Å^3

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	3176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 28°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −8→8
Tmin = 0.9, Tmax = 0.95	k = −10→10
13895 measured reflections	l = −21→21
3992 independent reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0631P)^2 + 0.1039P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.008
3992 reflections	Δρmax = 0.19 e Å^−3
252 parameters	Δρmin = −0.2 e Å^−3
15 restraints

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.62281 (15)	1.05882 (14)	0.41195 (7)	0.0344 (2)
C2	0.41780 (16)	1.05522 (15)	0.38634 (8)	0.0407 (3)
H2A	0.34625	1.157015	0.394349	0.049*
C3	0.32042 (18)	0.90041 (16)	0.34900 (8)	0.0452 (3)
H3	0.180262	0.898008	0.331897	0.054*
C4	0.61142 (19)	0.75840 (15)	0.36048 (8)	0.0454 (3)
H4	0.679611	0.655097	0.351111	0.054*
C5	0.71985 (17)	0.90663 (15)	0.39891 (8)	0.0395 (3)
H5	0.859292	0.904382	0.416219	0.047*
C6	0.74764 (15)	1.21634 (14)	0.45485 (7)	0.0354 (2)
N1	0.64879 (14)	1.35761 (12)	0.47241 (7)	0.0396 (2)
N2	0.41444 (16)	0.75400 (13)	0.33587 (7)	0.0460 (3)
N3	0.74431 (14)	1.50755 (13)	0.51959 (8)	0.0434 (3)
O1	0.92956 (11)	1.21112 (10)	0.47285 (6)	0.0478 (2)
H1	0.522 (2)	1.3601 (19)	0.4640 (9)	0.056 (4)*
H3A	0.832 (2)	1.5626 (19)	0.4890 (9)	0.053 (4)*
H3B	0.818 (3)	1.469 (2)	0.5638 (10)	0.064 (5)*
C7	−0.01943 (19)	0.24213 (15)	0.22933 (8)	0.0435 (3)
C8	0.1039 (2)	0.13611 (19)	0.18693 (10)	0.0599 (4)
H8	0.245581	0.169776	0.186951	0.072*
C9	0.0218 (2)	−0.01964 (19)	0.14422 (10)	0.0630 (4)
H9	0.109123	−0.091708	0.115837	0.076*
C10	−0.1842 (2)	−0.07236 (16)	0.14201 (8)	0.0468 (3)
C11	−0.3059 (2)	0.03606 (17)	0.18471 (8)	0.0497 (3)
H11	−0.447876	0.003577	0.184148	0.06*
C12	−0.2251 (2)	0.19077 (16)	0.22821 (8)	0.0468 (3)
H12	−0.311667	0.261965	0.257455	0.056*
C13	0.06626 (19)	0.40888 (16)	0.27600 (8)	0.0454 (3)
C14	−0.2730 (2)	−0.24347 (17)	0.09333 (8)	0.0508 (3)
C15A	−0.1006 (5)	−0.3523 (4)	0.0598 (3)	0.0816 (12)	0.512 (3)
H15A	−0.011286	−0.381706	0.105315	0.122*	0.512 (3)
H15B	−0.161859	−0.460726	0.029345	0.122*	0.512 (3)
H15C	−0.020901	−0.282587	0.023727	0.122*	0.512 (3)
C16A	−0.3861 (6)	−0.3610 (4)	0.15009 (18)	0.0671 (10)	0.512 (3)
H16A	−0.29118	−0.387776	0.194336	0.101*	0.512 (3)
H16B	−0.496856	−0.299671	0.172867	0.101*	0.512 (3)
H16C	−0.442549	−0.470515	0.119273	0.101*	0.512 (3)
C17A	−0.4086 (6)	−0.1984 (4)	0.02516 (18)	0.0691 (10)	0.512 (3)
H17A	−0.466598	−0.306415	−0.006533	0.104*	0.512 (3)
H17B	−0.518719	−0.134268	0.04666	0.104*	0.512 (3)
H17C	−0.330555	−0.124771	−0.009868	0.104*	0.512 (3)
C15B	−0.5132 (4)	−0.2689 (4)	0.0931 (2)	0.0628 (9)	0.488 (3)
H15D	−0.571654	−0.169519	0.069453	0.094*	0.488 (3)
H15E	−0.56346	−0.378158	0.060649	0.094*	0.488 (3)
H15F	−0.553085	−0.274749	0.149011	0.094*	0.488 (3)
C16B	−0.2278 (6)	−0.2352 (4)	0.00347 (17)	0.0638 (9)	0.488 (3)
H16D	−0.285525	−0.132756	−0.01759	0.096*	0.488 (3)
H16E	−0.080273	−0.225248	−0.001203	0.096*	0.488 (3)
H16F	−0.288967	−0.342319	−0.028049	0.096*	0.488 (3)
C17B	−0.1904 (6)	−0.3950 (4)	0.1292 (2)	0.0640 (10)	0.488 (3)
H17D	−0.247378	−0.50385	0.097985	0.096*	0.488 (3)
H17E	−0.041834	−0.384827	0.127741	0.096*	0.488 (3)
H17F	−0.226979	−0.396977	0.18571	0.096*	0.488 (3)
O2	0.25825 (15)	0.45139 (13)	0.26351 (7)	0.0629 (3)
O3	−0.03104 (14)	0.49683 (12)	0.32126 (6)	0.0536 (3)
H2	0.305 (3)	0.566 (3)	0.2930 (13)	0.105 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0270 (5)	0.0281 (5)	0.0481 (6)	−0.0001 (4)	0.0032 (4)	0.0047 (4)
C2	0.0282 (5)	0.0321 (5)	0.0612 (7)	0.0026 (4)	−0.0004 (5)	0.0016 (5)
C3	0.0295 (5)	0.0404 (6)	0.0632 (8)	−0.0042 (5)	−0.0018 (5)	0.0002 (5)
C4	0.0420 (6)	0.0307 (6)	0.0631 (8)	0.0039 (5)	0.0037 (5)	0.0003 (5)
C5	0.0305 (5)	0.0323 (5)	0.0557 (7)	0.0034 (4)	0.0026 (5)	0.0030 (5)
C6	0.0251 (5)	0.0276 (5)	0.0532 (6)	0.0004 (4)	0.0006 (4)	0.0056 (4)
N1	0.0217 (4)	0.0299 (5)	0.0650 (6)	0.0003 (4)	−0.0006 (4)	−0.0038 (4)
N2	0.0410 (5)	0.0336 (5)	0.0612 (6)	−0.0050 (4)	0.0029 (5)	−0.0017 (4)
N3	0.0251 (4)	0.0283 (5)	0.0743 (7)	−0.0011 (4)	−0.0009 (5)	−0.0050 (5)
O1	0.0258 (4)	0.0310 (4)	0.0848 (6)	0.0022 (3)	−0.0064 (4)	0.0017 (4)
C7	0.0457 (7)	0.0325 (6)	0.0508 (7)	−0.0014 (5)	0.0053 (5)	−0.0013 (5)
C8	0.0435 (7)	0.0488 (8)	0.0835 (10)	−0.0029 (6)	0.0120 (7)	−0.0167 (7)
C9	0.0561 (8)	0.0478 (8)	0.0815 (10)	−0.0010 (6)	0.0176 (7)	−0.0204 (7)
C10	0.0562 (7)	0.0341 (6)	0.0482 (7)	−0.0057 (5)	0.0072 (5)	−0.0010 (5)
C11	0.0461 (7)	0.0400 (6)	0.0607 (8)	−0.0076 (5)	0.0107 (6)	−0.0020 (6)
C12	0.0462 (7)	0.0361 (6)	0.0572 (7)	−0.0011 (5)	0.0127 (5)	−0.0034 (5)
C13	0.0440 (6)	0.0338 (6)	0.0569 (7)	0.0007 (5)	0.0019 (5)	−0.0014 (5)
C14	0.0623 (8)	0.0363 (6)	0.0508 (7)	−0.0059 (6)	0.0028 (6)	−0.0041 (5)
C15A	0.082 (2)	0.0517 (18)	0.103 (3)	−0.0035 (16)	0.009 (2)	−0.0342 (18)
C16A	0.093 (3)	0.0403 (14)	0.0624 (17)	−0.0208 (15)	0.0024 (16)	−0.0024 (12)
C17A	0.091 (3)	0.0557 (17)	0.0549 (17)	−0.0096 (16)	−0.0048 (16)	−0.0039 (13)
C15B	0.0603 (18)	0.0467 (16)	0.076 (2)	−0.0108 (13)	0.0007 (15)	−0.0105 (14)
C16B	0.085 (2)	0.0542 (17)	0.0501 (16)	0.0025 (16)	0.0048 (15)	−0.0047 (13)
C17B	0.086 (2)	0.0391 (15)	0.0652 (19)	0.0093 (15)	−0.0092 (17)	−0.0005 (13)
O2	0.0483 (5)	0.0457 (5)	0.0894 (8)	−0.0118 (4)	0.0149 (5)	−0.0192 (5)
O3	0.0469 (5)	0.0420 (5)	0.0689 (6)	0.0051 (4)	0.0015 (4)	−0.0127 (4)

Geometric parameters (Å, º)

C1—C5	1.3857 (15)	C12—H12	0.95
C1—C2	1.3918 (15)	C13—O3	1.2157 (15)
C1—C6	1.5063 (15)	C13—O2	1.3161 (16)
C2—C3	1.3828 (16)	C14—C17B	1.475 (3)
C2—H2A	0.95	C14—C17A	1.477 (3)
C3—N2	1.3365 (16)	C14—C16A	1.536 (3)
C3—H3	0.95	C14—C16B	1.538 (3)
C4—N2	1.3367 (16)	C14—C15A	1.569 (3)
C4—C5	1.3795 (16)	C14—C15B	1.582 (3)
C4—H4	0.95	C15A—H15A	0.98
C5—H5	0.95	C15A—H15B	0.98
C6—O1	1.2254 (12)	C15A—H15C	0.98
C6—N1	1.3321 (14)	C16A—H16A	0.98
N1—N3	1.4161 (13)	C16A—H16B	0.98
N1—H1	0.844 (16)	C16A—H16C	0.98
N3—H3A	0.892 (16)	C17A—H17A	0.98
N3—H3B	0.934 (17)	C17A—H17B	0.98
C7—C8	1.3802 (18)	C17A—H17C	0.98
C7—C12	1.3815 (17)	C15B—H15D	0.98
C7—C13	1.4900 (16)	C15B—H15E	0.98
C8—C9	1.3895 (19)	C15B—H15F	0.98
C8—H8	0.95	C16B—H16D	0.98
C9—C10	1.385 (2)	C16B—H16E	0.98
C9—H9	0.95	C16B—H16F	0.98
C10—C11	1.3864 (18)	C17B—H17D	0.98
C10—C14	1.5363 (17)	C17B—H17E	0.98
C11—C12	1.3862 (17)	C17B—H17F	0.98
C11—H11	0.95	O2—H2	0.98 (2)
C5—C1—C2	118.35 (10)	C17A—C14—C16A	112.0 (2)
C5—C1—C6	117.00 (9)	C10—C14—C16A	109.24 (14)
C2—C1—C6	124.63 (9)	C17B—C14—C16B	112.5 (2)
C3—C2—C1	118.63 (10)	C10—C14—C16B	109.36 (15)
C3—C2—H2A	120.7	C17A—C14—C15A	109.9 (2)
C1—C2—H2A	120.7	C10—C14—C15A	111.41 (15)
N2—C3—C2	123.01 (11)	C16A—C14—C15A	105.7 (2)
N2—C3—H3	118.5	C17B—C14—C15B	108.0 (2)
C2—C3—H3	118.5	C10—C14—C15B	112.18 (14)
N2—C4—C5	122.77 (11)	C16B—C14—C15B	105.1 (2)
N2—C4—H4	118.6	C14—C15A—H15A	109.5
C5—C4—H4	118.6	C14—C15A—H15B	109.5
C4—C5—C1	119.16 (10)	H15A—C15A—H15B	109.5
C4—C5—H5	120.4	C14—C15A—H15C	109.5
C1—C5—H5	120.4	H15A—C15A—H15C	109.5
O1—C6—N1	122.89 (10)	H15B—C15A—H15C	109.5
O1—C6—C1	120.74 (9)	C14—C16A—H16A	109.5
N1—C6—C1	116.36 (9)	C14—C16A—H16B	109.5
C6—N1—N3	121.69 (9)	H16A—C16A—H16B	109.5
C6—N1—H1	123.8 (10)	C14—C16A—H16C	109.5
N3—N1—H1	113.7 (10)	H16A—C16A—H16C	109.5
C3—N2—C4	118.07 (10)	H16B—C16A—H16C	109.5
N1—N3—H3A	108.0 (9)	C14—C17A—H17A	109.5
N1—N3—H3B	108.0 (10)	C14—C17A—H17B	109.5
H3A—N3—H3B	108.4 (14)	H17A—C17A—H17B	109.5
C8—C7—C12	118.83 (11)	C14—C17A—H17C	109.5
C8—C7—C13	121.01 (11)	H17A—C17A—H17C	109.5
C12—C7—C13	120.16 (11)	H17B—C17A—H17C	109.5
C7—C8—C9	120.28 (13)	C14—C15B—H15D	109.5
C7—C8—H8	119.9	C14—C15B—H15E	109.5
C9—C8—H8	119.9	H15D—C15B—H15E	109.5
C10—C9—C8	121.59 (13)	C14—C15B—H15F	109.5
C10—C9—H9	119.2	H15D—C15B—H15F	109.5
C8—C9—H9	119.2	H15E—C15B—H15F	109.5
C9—C10—C11	117.33 (11)	C14—C16B—H16D	109.5
C9—C10—C14	120.93 (12)	C14—C16B—H16E	109.5
C11—C10—C14	121.75 (12)	H16D—C16B—H16E	109.5
C12—C11—C10	121.51 (12)	C14—C16B—H16F	109.5
C12—C11—H11	119.2	H16D—C16B—H16F	109.5
C10—C11—H11	119.2	H16E—C16B—H16F	109.5
C7—C12—C11	120.45 (12)	C14—C17B—H17D	109.5
C7—C12—H12	119.8	C14—C17B—H17E	109.5
C11—C12—H12	119.8	H17D—C17B—H17E	109.5
O3—C13—O2	123.28 (11)	C14—C17B—H17F	109.5
O3—C13—C7	123.46 (11)	H17D—C17B—H17F	109.5
O2—C13—C7	113.27 (11)	H17E—C17B—H17F	109.5
C17B—C14—C10	109.72 (16)	C13—O2—H2	110.1 (13)
C17A—C14—C10	108.49 (15)
C5—C1—C2—C3	−0.10 (18)	C14—C10—C11—C12	−179.67 (12)
C6—C1—C2—C3	−178.74 (11)	C8—C7—C12—C11	−0.5 (2)
C1—C2—C3—N2	−0.4 (2)	C13—C7—C12—C11	179.80 (12)
N2—C4—C5—C1	−0.9 (2)	C10—C11—C12—C7	0.7 (2)
C2—C1—C5—C4	0.71 (18)	C8—C7—C13—O3	−171.73 (14)
C6—C1—C5—C4	179.45 (11)	C12—C7—C13—O3	8.0 (2)
C5—C1—C6—O1	4.05 (17)	C8—C7—C13—O2	8.11 (19)
C2—C1—C6—O1	−177.29 (12)	C12—C7—C13—O2	−172.18 (12)
C5—C1—C6—N1	−175.15 (11)	C9—C10—C14—C17B	65.0 (2)
C2—C1—C6—N1	3.51 (17)	C11—C10—C14—C17B	−115.6 (2)
O1—C6—N1—N3	−5.51 (18)	C9—C10—C14—C17A	−113.6 (2)
C1—C6—N1—N3	173.67 (10)	C11—C10—C14—C17A	65.8 (2)
C2—C3—N2—C4	0.30 (19)	C9—C10—C14—C16A	124.0 (2)
C5—C4—N2—C3	0.3 (2)	C11—C10—C14—C16A	−56.6 (2)
C12—C7—C8—C9	−0.2 (2)	C9—C10—C14—C16B	−58.8 (2)
C13—C7—C8—C9	179.51 (14)	C11—C10—C14—C16B	120.6 (2)
C7—C8—C9—C10	0.7 (3)	C9—C10—C14—C15A	7.6 (3)
C8—C9—C10—C11	−0.4 (2)	C11—C10—C14—C15A	−173.0 (2)
C8—C9—C10—C14	178.98 (14)	C9—C10—C14—C15B	−174.96 (18)
C9—C10—C11—C12	−0.3 (2)	C11—C10—C14—C15B	4.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3^i	0.844 (16)	2.122 (15)	2.8807 (13)	149 (1)
N3—H3A···O1^ii	0.892 (16)	2.269 (16)	2.9095 (13)	129 (1)
N3—H3B···O3^iii	0.934 (17)	2.279 (17)	3.1513 (15)	155 (1)
O2—H2···N2	0.98 (2)	1.65 (2)	2.6248 (13)	172 (2)

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

4-tert-Butylbenzoic acid–N'-(propan-2-ylidene)pyridine-4-carbohydrazide (1/1) (II)

Crystal data

C9H11N3O·C11H14O2	F(000) = 1520
Mr = 355.43	Dx = 1.206 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9867 reflections
a = 14.2337 (6) Å	θ = 2.2–28.2°
b = 13.7116 (5) Å	µ = 0.08 mm^−1
c = 20.3233 (8) Å	T = 173 K
β = 99.298 (2)°	Blocks, colourless
V = 3914.3 (3) Å^3	0.89 × 0.87 × 0.44 mm
Z = 8

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	7394 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −18→17
Tmin = 0.9, Tmax = 0.95	k = −18→17
40471 measured reflections	l = −25→26
9446 independent reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 1.5864P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.003
9446 reflections	Δρmax = 0.44 e Å^−3
517 parameters	Δρmin = −0.32 e Å^−3
99 restraints

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.29018 (9)	−0.10036 (10)	0.21896 (7)	0.0251 (3)
C2A	0.25203 (10)	−0.05583 (10)	0.15947 (7)	0.0301 (3)
H2C	0.265668	−0.079817	0.118181	0.036*
C3A	0.19345 (11)	0.02459 (11)	0.16151 (8)	0.0327 (3)
H3A	0.167288	0.054939	0.120614	0.039*
C4A	0.20724 (10)	0.01655 (11)	0.27515 (8)	0.0326 (3)
H4A	0.191422	0.041135	0.315676	0.039*
C5A	0.26588 (10)	−0.06439 (11)	0.27763 (7)	0.0306 (3)
H5A	0.289147	−0.094851	0.319048	0.037*
C6A	0.35178 (10)	−0.18966 (10)	0.22177 (7)	0.0268 (3)
C7A	0.54580 (12)	−0.20221 (12)	0.08856 (9)	0.0413 (4)
H7A1	0.487695	−0.164603	0.073706	0.062*
H7A2	0.567786	−0.231764	0.049857	0.062*
H7A3	0.595307	−0.158861	0.111448	0.062*
C8A	0.52544 (11)	−0.28038 (12)	0.13519 (9)	0.0374 (3)
C9A	0.57944 (17)	−0.37443 (16)	0.13427 (13)	0.0692 (7)
H9A1	0.561165	−0.419034	0.167696	0.104*
H9A2	0.647929	−0.36133	0.144518	0.104*
H9A3	0.564433	−0.404238	0.08999	0.104*
N1A	0.41137 (8)	−0.19314 (8)	0.17671 (6)	0.0276 (3)
N2A	0.17191 (9)	0.06159 (9)	0.21811 (6)	0.0315 (3)
N3A	0.46596 (9)	−0.27726 (9)	0.17607 (7)	0.0338 (3)
O1A	0.34372 (9)	−0.25426 (8)	0.26231 (6)	0.0391 (3)
H1A	0.4257 (13)	−0.1393 (14)	0.1558 (9)	0.041 (5)*
C10A	0.07977 (9)	0.38639 (10)	0.13626 (7)	0.0247 (3)
C11A	0.04411 (10)	0.43589 (10)	0.18701 (7)	0.0271 (3)
H11A	0.033051	0.401665	0.225672	0.033*
C12A	0.02487 (9)	0.53465 (10)	0.18105 (7)	0.0267 (3)
H12A	−0.00005	0.567123	0.215755	0.032*
C13A	0.04113 (9)	0.58809 (10)	0.12524 (7)	0.0241 (3)
C14A	0.07571 (10)	0.53735 (10)	0.07477 (7)	0.0275 (3)
H14A	0.086523	0.571324	0.035952	0.033*
C15A	0.09472 (10)	0.43785 (10)	0.08014 (7)	0.0274 (3)
H15A	0.118168	0.404872	0.045016	0.033*
C16A	0.10469 (9)	0.28079 (10)	0.14175 (7)	0.0270 (3)
C17A	0.02145 (10)	0.69815 (10)	0.12209 (7)	0.0274 (3)
C18A	0.04925 (14)	0.74520 (12)	0.05979 (9)	0.0440 (4)
H18A	0.03549	0.815224	0.059876	0.066*
H18B	0.117407	0.735345	0.059626	0.066*
H18C	0.012672	0.715182	0.019928	0.066*
C19A	0.07834 (12)	0.74711 (12)	0.18394 (9)	0.0402 (4)
H19A	0.061125	0.717532	0.224247	0.06*
H19B	0.146596	0.738084	0.183734	0.06*
H19C	0.063625	0.816953	0.183319	0.06*
C20A	−0.08517 (11)	0.71575 (11)	0.12184 (9)	0.0364 (3)
H20A	−0.104006	0.685934	0.161555	0.055*
H20B	−0.097597	0.786036	0.122033	0.055*
H20C	−0.12195	0.686495	0.081765	0.055*
O2A	0.09261 (8)	0.24176 (8)	0.19966 (5)	0.0350 (2)
O3A	0.13385 (8)	0.23520 (8)	0.09816 (5)	0.0367 (2)
H2A	0.1166 (17)	0.1729 (18)	0.2037 (12)	0.072 (7)*
C1B	0.45291 (9)	0.17167 (9)	0.10916 (7)	0.0253 (3)
C2B	0.52256 (10)	0.24239 (10)	0.10809 (8)	0.0319 (3)
H2D	0.587177	0.229493	0.126105	0.038*
C3B	0.49537 (11)	0.33213 (11)	0.08009 (9)	0.0366 (3)
H3B	0.542882	0.380684	0.079674	0.044*
C4B	0.33952 (11)	0.28468 (11)	0.05332 (8)	0.0322 (3)
H4B	0.275813	0.299069	0.03379	0.039*
C5B	0.36003 (10)	0.19301 (10)	0.08029 (7)	0.0292 (3)
H5B	0.311297	0.145388	0.079061	0.035*
C6B	0.47451 (9)	0.07076 (9)	0.13644 (7)	0.0249 (3)
C7B	0.69225 (14)	0.03526 (14)	0.30062 (10)	0.0525 (5)
H7B1	0.708465	0.087455	0.271479	0.079*
H7B2	0.750806	0.007122	0.325328	0.079*
H7B3	0.653607	0.062005	0.332115	0.079*
C8B	0.63756 (10)	−0.04163 (11)	0.25967 (7)	0.0304 (3)
C9B	0.66609 (14)	−0.14486 (13)	0.27633 (10)	0.0502 (5)
H9B1	0.61679	−0.18908	0.254193	0.075*
H9B2	0.673633	−0.154272	0.3247	0.075*
H9B3	0.726534	−0.15885	0.261014	0.075*
N1B	0.54414 (8)	0.06390 (8)	0.18951 (6)	0.0277 (2)
N2B	0.40587 (9)	0.35389 (9)	0.05367 (7)	0.0341 (3)
N3B	0.56980 (9)	−0.03036 (9)	0.21078 (6)	0.0318 (3)
O1B	0.42949 (7)	0.00067 (7)	0.10983 (5)	0.0322 (2)
H1B	0.5712 (13)	0.1167 (14)	0.2113 (9)	0.039 (5)*
C10B	0.25277 (9)	0.64916 (10)	−0.03514 (7)	0.0255 (3)
C11B	0.30335 (10)	0.72580 (10)	−0.00137 (8)	0.0302 (3)
H11B	0.356196	0.712418	0.032347	0.036*
C12B	0.27722 (10)	0.82151 (10)	−0.01653 (7)	0.0299 (3)
H12B	0.312858	0.872936	0.006856	0.036*
C13B	0.19972 (10)	0.84398 (10)	−0.06541 (7)	0.0264 (3)
C14B	0.14933 (10)	0.76608 (11)	−0.09831 (7)	0.0310 (3)
H14B	0.096102	0.779175	−0.131789	0.037*
C15B	0.17494 (10)	0.67015 (11)	−0.08341 (7)	0.0303 (3)
H15B	0.139031	0.618549	−0.106369	0.036*
C16B	0.28065 (10)	0.54533 (10)	−0.02117 (7)	0.0291 (3)
C17B	0.17156 (11)	0.94991 (11)	−0.08219 (7)	0.0326 (3)
C18B	0.0753 (4)	0.9579 (4)	−0.1259 (3)	0.106 (2)	0.632 (7)
H18D	0.026804	0.927772	−0.10332	0.158*	0.632 (7)
H18E	0.059605	1.026823	−0.134548	0.158*	0.632 (7)
H18F	0.076994	0.924341	−0.168294	0.158*	0.632 (7)
C19B	0.2427 (5)	0.9960 (4)	−0.1178 (5)	0.141 (3)	0.632 (7)
H19F	0.247242	0.958813	−0.158336	0.212*	0.632 (7)
H19E	0.223062	1.06303	−0.129808	0.212*	0.632 (7)
H19D	0.304799	0.996682	−0.088852	0.212*	0.632 (7)
C20B	0.1619 (5)	1.0046 (3)	−0.01927 (16)	0.0748 (17)	0.632 (7)
H20D	0.11439	0.97235	0.003127	0.112*	0.632 (7)
H20E	0.223417	1.005392	0.010453	0.112*	0.632 (7)
H20F	0.141681	1.071741	−0.030503	0.112*	0.632 (7)
C21B	0.2366 (9)	1.0227 (4)	−0.0427 (6)	0.105 (4)	0.368 (7)
H21A	0.302774	1.007462	−0.046512	0.158*	0.368 (7)
H21B	0.22095	1.08841	−0.060194	0.158*	0.368 (7)
H21C	0.228481	1.019885	0.004188	0.158*	0.368 (7)
C22B	0.1882 (11)	0.9671 (7)	−0.1522 (3)	0.107 (4)	0.368 (7)
H22A	0.255949	0.958419	−0.154466	0.161*	0.368 (7)
H22B	0.150674	0.920414	−0.182152	0.161*	0.368 (7)
H22C	0.168875	1.033655	−0.165766	0.161*	0.368 (7)
C23B	0.0702 (5)	0.9636 (6)	−0.0812 (9)	0.144 (5)	0.368 (7)
H23A	0.056974	0.952777	−0.035918	0.216*	0.368 (7)
H23B	0.051782	1.030153	−0.095348	0.216*	0.368 (7)
H23C	0.033581	0.916912	−0.111734	0.216*	0.368 (7)
O2B	0.36109 (8)	0.53564 (8)	0.02060 (6)	0.0427 (3)
O3B	0.23449 (8)	0.47694 (8)	−0.04657 (6)	0.0446 (3)
H2B	0.3753 (17)	0.4671 (19)	0.0272 (12)	0.077 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0245 (6)	0.0194 (6)	0.0309 (7)	0.0000 (5)	0.0033 (5)	0.0026 (5)
C2A	0.0339 (7)	0.0255 (7)	0.0313 (7)	0.0053 (5)	0.0069 (6)	0.0036 (6)
C3A	0.0348 (7)	0.0286 (7)	0.0349 (8)	0.0080 (6)	0.0066 (6)	0.0080 (6)
C4A	0.0333 (7)	0.0312 (8)	0.0341 (8)	0.0049 (6)	0.0078 (6)	−0.0007 (6)
C5A	0.0332 (7)	0.0292 (7)	0.0290 (7)	0.0049 (6)	0.0034 (6)	0.0041 (6)
C6A	0.0287 (6)	0.0194 (6)	0.0303 (7)	0.0014 (5)	−0.0013 (5)	0.0018 (5)
C7A	0.0410 (8)	0.0386 (9)	0.0467 (9)	−0.0004 (7)	0.0149 (7)	−0.0082 (7)
C8A	0.0321 (7)	0.0315 (8)	0.0473 (9)	0.0070 (6)	0.0028 (7)	−0.0047 (7)
C9A	0.0676 (13)	0.0538 (13)	0.0913 (17)	0.0352 (11)	0.0282 (12)	0.0085 (12)
N1A	0.0276 (6)	0.0164 (5)	0.0383 (7)	0.0025 (4)	0.0038 (5)	0.0025 (5)
N2A	0.0311 (6)	0.0253 (6)	0.0388 (7)	0.0060 (5)	0.0079 (5)	0.0039 (5)
N3A	0.0312 (6)	0.0228 (6)	0.0462 (8)	0.0080 (5)	0.0028 (5)	0.0019 (5)
O1A	0.0516 (7)	0.0283 (6)	0.0388 (6)	0.0107 (5)	0.0111 (5)	0.0117 (5)
C10A	0.0215 (6)	0.0232 (6)	0.0286 (7)	0.0010 (5)	0.0016 (5)	0.0018 (5)
C11A	0.0293 (6)	0.0253 (7)	0.0272 (7)	0.0009 (5)	0.0061 (5)	0.0042 (5)
C12A	0.0290 (6)	0.0248 (7)	0.0268 (7)	0.0016 (5)	0.0066 (5)	0.0004 (5)
C13A	0.0216 (6)	0.0224 (6)	0.0276 (7)	−0.0004 (5)	0.0019 (5)	0.0018 (5)
C14A	0.0313 (7)	0.0260 (7)	0.0257 (7)	0.0010 (5)	0.0058 (5)	0.0044 (5)
C15A	0.0296 (7)	0.0265 (7)	0.0262 (7)	0.0026 (5)	0.0047 (5)	−0.0013 (5)
C16A	0.0234 (6)	0.0249 (7)	0.0322 (7)	0.0016 (5)	0.0026 (5)	0.0020 (5)
C17A	0.0295 (6)	0.0210 (6)	0.0324 (7)	0.0002 (5)	0.0071 (5)	0.0020 (5)
C18A	0.0620 (11)	0.0258 (8)	0.0491 (10)	0.0045 (7)	0.0232 (8)	0.0100 (7)
C19A	0.0410 (8)	0.0281 (8)	0.0494 (10)	−0.0057 (6)	0.0009 (7)	−0.0059 (7)
C20A	0.0323 (7)	0.0256 (7)	0.0510 (10)	0.0044 (6)	0.0054 (7)	0.0031 (7)
O2A	0.0452 (6)	0.0250 (5)	0.0373 (6)	0.0099 (4)	0.0142 (5)	0.0083 (4)
O3A	0.0476 (6)	0.0274 (5)	0.0371 (6)	0.0094 (4)	0.0128 (5)	0.0016 (4)
C1B	0.0292 (6)	0.0191 (6)	0.0273 (7)	0.0024 (5)	0.0038 (5)	0.0006 (5)
C2B	0.0282 (7)	0.0254 (7)	0.0405 (8)	0.0005 (5)	0.0013 (6)	0.0049 (6)
C3B	0.0369 (8)	0.0239 (7)	0.0485 (9)	−0.0024 (6)	0.0055 (7)	0.0070 (6)
C4B	0.0308 (7)	0.0289 (7)	0.0364 (8)	0.0074 (6)	0.0036 (6)	0.0036 (6)
C5B	0.0283 (6)	0.0241 (7)	0.0347 (7)	0.0007 (5)	0.0034 (6)	0.0017 (6)
C6B	0.0251 (6)	0.0189 (6)	0.0303 (7)	0.0011 (5)	0.0034 (5)	0.0006 (5)
C7B	0.0526 (10)	0.0381 (9)	0.0568 (11)	0.0095 (8)	−0.0215 (9)	−0.0114 (8)
C8B	0.0319 (7)	0.0292 (7)	0.0288 (7)	−0.0003 (6)	0.0011 (6)	0.0041 (6)
C9B	0.0589 (11)	0.0333 (9)	0.0497 (11)	−0.0016 (8)	−0.0176 (9)	0.0140 (8)
N1B	0.0324 (6)	0.0170 (5)	0.0312 (6)	−0.0011 (4)	−0.0025 (5)	−0.0002 (5)
N2B	0.0388 (7)	0.0235 (6)	0.0398 (7)	0.0064 (5)	0.0062 (5)	0.0056 (5)
N3B	0.0375 (6)	0.0208 (6)	0.0337 (7)	−0.0024 (5)	−0.0043 (5)	0.0068 (5)
O1B	0.0336 (5)	0.0205 (5)	0.0386 (6)	−0.0017 (4)	−0.0061 (4)	0.0006 (4)
C10B	0.0263 (6)	0.0233 (6)	0.0276 (7)	0.0024 (5)	0.0065 (5)	0.0017 (5)
C11B	0.0280 (6)	0.0267 (7)	0.0334 (8)	0.0024 (5)	−0.0028 (6)	0.0017 (6)
C12B	0.0312 (7)	0.0240 (7)	0.0326 (7)	−0.0005 (5)	−0.0003 (6)	−0.0002 (6)
C13B	0.0306 (7)	0.0253 (7)	0.0238 (7)	0.0042 (5)	0.0065 (5)	0.0032 (5)
C14B	0.0315 (7)	0.0313 (7)	0.0280 (7)	0.0057 (6)	−0.0015 (6)	−0.0017 (6)
C15B	0.0291 (7)	0.0291 (7)	0.0317 (7)	0.0005 (5)	0.0016 (6)	−0.0054 (6)
C16B	0.0310 (7)	0.0242 (7)	0.0335 (7)	0.0017 (5)	0.0093 (6)	0.0013 (6)
C17B	0.0395 (8)	0.0257 (7)	0.0316 (8)	0.0050 (6)	0.0028 (6)	0.0061 (6)
C18B	0.117 (4)	0.040 (2)	0.125 (4)	0.029 (3)	−0.085 (3)	−0.006 (3)
C19B	0.141 (5)	0.061 (4)	0.261 (8)	0.046 (3)	0.152 (6)	0.089 (5)
C20B	0.139 (5)	0.0333 (19)	0.0464 (18)	0.039 (2)	−0.002 (2)	−0.0012 (14)
C21B	0.156 (8)	0.018 (3)	0.111 (6)	−0.004 (4)	−0.072 (7)	0.009 (3)
C22B	0.223 (11)	0.049 (5)	0.056 (3)	0.025 (6)	0.043 (5)	0.033 (3)
C23B	0.061 (4)	0.035 (4)	0.358 (15)	0.028 (3)	0.097 (6)	0.050 (8)
O2B	0.0421 (6)	0.0230 (5)	0.0578 (8)	0.0045 (4)	−0.0080 (5)	0.0081 (5)
O3B	0.0470 (7)	0.0243 (6)	0.0590 (8)	−0.0006 (5)	−0.0019 (6)	−0.0049 (5)

Geometric parameters (Å, º)

C1A—C2A	1.385 (2)	C3B—H3B	0.95
C1A—C5A	1.385 (2)	C4B—N2B	1.338 (2)
C1A—C6A	1.5017 (18)	C4B—C5B	1.383 (2)
C2A—C3A	1.3872 (19)	C4B—H4B	0.95
C2A—H2C	0.95	C5B—H5B	0.95
C3A—N2A	1.337 (2)	C6B—O1B	1.2308 (16)
C3A—H3A	0.95	C6B—N1B	1.3450 (18)
C4A—N2A	1.338 (2)	C7B—C8B	1.484 (2)
C4A—C5A	1.385 (2)	C7B—H7B1	0.98
C4A—H4A	0.95	C7B—H7B2	0.98
C5A—H5A	0.95	C7B—H7B3	0.98
C6A—O1A	1.2276 (17)	C8B—N3B	1.2773 (19)
C6A—N1A	1.3459 (18)	C8B—C9B	1.496 (2)
C7A—C8A	1.490 (2)	C9B—H9B1	0.98
C7A—H7A1	0.98	C9B—H9B2	0.98
C7A—H7A2	0.98	C9B—H9B3	0.98
C7A—H7A3	0.98	N1B—N3B	1.3927 (16)
C8A—N3A	1.279 (2)	N1B—H1B	0.902 (19)
C8A—C9A	1.503 (2)	C10B—C15B	1.386 (2)
C9A—H9A1	0.98	C10B—C11B	1.391 (2)
C9A—H9A2	0.98	C10B—C16B	1.4929 (19)
C9A—H9A3	0.98	C11B—C12B	1.3851 (19)
N1A—N3A	1.3919 (16)	C11B—H11B	0.95
N1A—H1A	0.892 (19)	C12B—C13B	1.394 (2)
C10A—C15A	1.3865 (19)	C12B—H12B	0.95
C10A—C11A	1.3969 (19)	C13B—C14B	1.396 (2)
C10A—C16A	1.4906 (18)	C13B—C17B	1.5305 (19)
C11A—C12A	1.3829 (19)	C14B—C15B	1.385 (2)
C11A—H11A	0.95	C14B—H14B	0.95
C12A—C13A	1.4006 (19)	C15B—H15B	0.95
C12A—H12A	0.95	C16B—O3B	1.2115 (18)
C13A—C14A	1.3933 (19)	C16B—O2B	1.3172 (18)
C13A—C17A	1.5344 (18)	C17B—C23B	1.459 (5)
C14A—C15A	1.3917 (19)	C17B—C19B	1.478 (4)
C14A—H14A	0.95	C17B—C22B	1.498 (6)
C15A—H15A	0.95	C17B—C21B	1.502 (5)
C16A—O3A	1.2111 (17)	C17B—C20B	1.508 (3)
C16A—O2A	1.3292 (17)	C17B—C18B	1.512 (4)
C17A—C18A	1.529 (2)	C18B—H18D	0.98
C17A—C19A	1.535 (2)	C18B—H18E	0.98
C17A—C20A	1.536 (2)	C18B—H18F	0.98
C18A—H18A	0.98	C19B—H19F	0.98
C18A—H18B	0.98	C19B—H19E	0.98
C18A—H18C	0.98	C19B—H19D	0.98
C19A—H19A	0.98	C20B—H20D	0.98
C19A—H19B	0.98	C20B—H20E	0.98
C19A—H19C	0.98	C20B—H20F	0.98
C20A—H20A	0.98	C21B—H21A	0.98
C20A—H20B	0.98	C21B—H21B	0.98
C20A—H20C	0.98	C21B—H21C	0.98
O2A—H2A	1.00 (2)	C22B—H22A	0.98
C1B—C5B	1.3882 (19)	C22B—H22B	0.98
C1B—C2B	1.3894 (19)	C22B—H22C	0.98
C1B—C6B	1.5038 (18)	C23B—H23A	0.98
C2B—C3B	1.384 (2)	C23B—H23B	0.98
C2B—H2D	0.95	C23B—H23C	0.98
C3B—N2B	1.334 (2)	O2B—H2B	0.97 (3)
C2A—C1A—C5A	118.52 (12)	C4B—C5B—C1B	118.98 (13)
C2A—C1A—C6A	122.47 (12)	C4B—C5B—H5B	120.5
C5A—C1A—C6A	118.89 (12)	C1B—C5B—H5B	120.5
C1A—C2A—C3A	118.50 (13)	O1B—C6B—N1B	124.17 (12)
C1A—C2A—H2C	120.7	O1B—C6B—C1B	119.70 (12)
C3A—C2A—H2C	120.7	N1B—C6B—C1B	116.12 (11)
N2A—C3A—C2A	123.35 (14)	C8B—C7B—H7B1	109.5
N2A—C3A—H3A	118.3	C8B—C7B—H7B2	109.5
C2A—C3A—H3A	118.3	H7B1—C7B—H7B2	109.5
N2A—C4A—C5A	122.79 (14)	C8B—C7B—H7B3	109.5
N2A—C4A—H4A	118.6	H7B1—C7B—H7B3	109.5
C5A—C4A—H4A	118.6	H7B2—C7B—H7B3	109.5
C4A—C5A—C1A	119.15 (13)	N3B—C8B—C7B	127.75 (14)
C4A—C5A—H5A	120.4	N3B—C8B—C9B	115.70 (14)
C1A—C5A—H5A	120.4	C7B—C8B—C9B	116.53 (14)
O1A—C6A—N1A	124.65 (13)	C8B—C9B—H9B1	109.5
O1A—C6A—C1A	119.77 (13)	C8B—C9B—H9B2	109.5
N1A—C6A—C1A	115.55 (12)	H9B1—C9B—H9B2	109.5
C8A—C7A—H7A1	109.5	C8B—C9B—H9B3	109.5
C8A—C7A—H7A2	109.5	H9B1—C9B—H9B3	109.5
H7A1—C7A—H7A2	109.5	H9B2—C9B—H9B3	109.5
C8A—C7A—H7A3	109.5	C6B—N1B—N3B	115.85 (11)
H7A1—C7A—H7A3	109.5	C6B—N1B—H1B	122.5 (12)
H7A2—C7A—H7A3	109.5	N3B—N1B—H1B	121.6 (12)
N3A—C8A—C7A	127.32 (14)	C3B—N2B—C4B	118.09 (13)
N3A—C8A—C9A	115.49 (16)	C8B—N3B—N1B	118.74 (12)
C7A—C8A—C9A	117.19 (15)	C15B—C10B—C11B	118.89 (13)
C8A—C9A—H9A1	109.5	C15B—C10B—C16B	119.34 (13)
C8A—C9A—H9A2	109.5	C11B—C10B—C16B	121.76 (13)
H9A1—C9A—H9A2	109.5	C12B—C11B—C10B	120.48 (13)
C8A—C9A—H9A3	109.5	C12B—C11B—H11B	119.8
H9A1—C9A—H9A3	109.5	C10B—C11B—H11B	119.8
H9A2—C9A—H9A3	109.5	C11B—C12B—C13B	121.39 (13)
C6A—N1A—N3A	116.74 (12)	C11B—C12B—H12B	119.3
C6A—N1A—H1A	120.9 (12)	C13B—C12B—H12B	119.3
N3A—N1A—H1A	120.7 (12)	C12B—C13B—C14B	117.29 (13)
C3A—N2A—C4A	117.64 (12)	C12B—C13B—C17B	121.12 (13)
C8A—N3A—N1A	117.57 (13)	C14B—C13B—C17B	121.59 (13)
C15A—C10A—C11A	118.84 (12)	C15B—C14B—C13B	121.68 (13)
C15A—C10A—C16A	119.32 (12)	C15B—C14B—H14B	119.2
C11A—C10A—C16A	121.82 (12)	C13B—C14B—H14B	119.2
C12A—C11A—C10A	120.11 (13)	C14B—C15B—C10B	120.25 (13)
C12A—C11A—H11A	119.9	C14B—C15B—H15B	119.9
C10A—C11A—H11A	119.9	C10B—C15B—H15B	119.9
C11A—C12A—C13A	121.79 (12)	O3B—C16B—O2B	123.48 (14)
C11A—C12A—H12A	119.1	O3B—C16B—C10B	123.23 (13)
C13A—C12A—H12A	119.1	O2B—C16B—C10B	113.29 (12)
C14A—C13A—C12A	117.33 (12)	C23B—C17B—C22B	107.5 (8)
C14A—C13A—C17A	122.97 (12)	C23B—C17B—C21B	115.7 (7)
C12A—C13A—C17A	119.70 (12)	C22B—C17B—C21B	102.9 (6)
C15A—C14A—C13A	121.27 (12)	C19B—C17B—C20B	111.5 (4)
C15A—C14A—H14A	119.4	C19B—C17B—C18B	108.0 (4)
C13A—C14A—H14A	119.4	C20B—C17B—C18B	105.3 (3)
C10A—C15A—C14A	120.64 (13)	C23B—C17B—C13B	110.0 (3)
C10A—C15A—H15A	119.7	C19B—C17B—C13B	109.8 (2)
C14A—C15A—H15A	119.7	C22B—C17B—C13B	106.5 (4)
O3A—C16A—O2A	123.27 (13)	C21B—C17B—C13B	113.3 (3)
O3A—C16A—C10A	123.52 (13)	C20B—C17B—C13B	109.87 (17)
O2A—C16A—C10A	113.21 (12)	C18B—C17B—C13B	112.3 (2)
C18A—C17A—C13A	112.31 (12)	C17B—C18B—H18D	109.5
C18A—C17A—C19A	108.70 (13)	C17B—C18B—H18E	109.5
C13A—C17A—C19A	109.11 (12)	H18D—C18B—H18E	109.5
C18A—C17A—C20A	108.58 (13)	C17B—C18B—H18F	109.5
C13A—C17A—C20A	109.16 (11)	H18D—C18B—H18F	109.5
C19A—C17A—C20A	108.92 (12)	H18E—C18B—H18F	109.5
C17A—C18A—H18A	109.5	C17B—C19B—H19F	109.5
C17A—C18A—H18B	109.5	C17B—C19B—H19E	109.5
H18A—C18A—H18B	109.5	H19F—C19B—H19E	109.5
C17A—C18A—H18C	109.5	C17B—C19B—H19D	109.5
H18A—C18A—H18C	109.5	H19F—C19B—H19D	109.5
H18B—C18A—H18C	109.5	H19E—C19B—H19D	109.5
C17A—C19A—H19A	109.5	C17B—C20B—H20D	109.5
C17A—C19A—H19B	109.5	C17B—C20B—H20E	109.5
H19A—C19A—H19B	109.5	H20D—C20B—H20E	109.5
C17A—C19A—H19C	109.5	C17B—C20B—H20F	109.5
H19A—C19A—H19C	109.5	H20D—C20B—H20F	109.5
H19B—C19A—H19C	109.5	H20E—C20B—H20F	109.5
C17A—C20A—H20A	109.5	C17B—C21B—H21A	109.5
C17A—C20A—H20B	109.5	C17B—C21B—H21B	109.5
H20A—C20A—H20B	109.5	H21A—C21B—H21B	109.5
C17A—C20A—H20C	109.5	C17B—C21B—H21C	109.5
H20A—C20A—H20C	109.5	H21A—C21B—H21C	109.5
H20B—C20A—H20C	109.5	H21B—C21B—H21C	109.5
C16A—O2A—H2A	111.1 (14)	C17B—C22B—H22A	109.5
C5B—C1B—C2B	118.65 (12)	C17B—C22B—H22B	109.5
C5B—C1B—C6B	118.28 (12)	H22A—C22B—H22B	109.5
C2B—C1B—C6B	122.96 (12)	C17B—C22B—H22C	109.5
C3B—C2B—C1B	118.30 (13)	H22A—C22B—H22C	109.5
C3B—C2B—H2D	120.9	H22B—C22B—H22C	109.5
C1B—C2B—H2D	120.9	C17B—C23B—H23A	109.5
N2B—C3B—C2B	123.34 (14)	C17B—C23B—H23B	109.5
N2B—C3B—H3B	118.3	H23A—C23B—H23B	109.5
C2B—C3B—H3B	118.3	C17B—C23B—H23C	109.5
N2B—C4B—C5B	122.60 (13)	H23A—C23B—H23C	109.5
N2B—C4B—H4B	118.7	H23B—C23B—H23C	109.5
C5B—C4B—H4B	118.7	C16B—O2B—H2B	109.2 (15)
C5A—C1A—C2A—C3A	1.9 (2)	N2B—C4B—C5B—C1B	0.3 (2)
C6A—C1A—C2A—C3A	177.99 (13)	C2B—C1B—C5B—C4B	−1.9 (2)
C1A—C2A—C3A—N2A	0.1 (2)	C6B—C1B—C5B—C4B	−178.26 (13)
N2A—C4A—C5A—C1A	0.6 (2)	C5B—C1B—C6B—O1B	32.02 (19)
C2A—C1A—C5A—C4A	−2.2 (2)	C2B—C1B—C6B—O1B	−144.13 (14)
C6A—C1A—C5A—C4A	−178.47 (13)	C5B—C1B—C6B—N1B	−148.36 (13)
C2A—C1A—C6A—O1A	−141.31 (15)	C2B—C1B—C6B—N1B	35.48 (19)
C5A—C1A—C6A—O1A	34.78 (19)	O1B—C6B—N1B—N3B	5.3 (2)
C2A—C1A—C6A—N1A	36.89 (19)	C1B—C6B—N1B—N3B	−174.34 (11)
C5A—C1A—C6A—N1A	−147.02 (13)	C2B—C3B—N2B—C4B	−1.2 (2)
O1A—C6A—N1A—N3A	1.1 (2)	C5B—C4B—N2B—C3B	1.3 (2)
C1A—C6A—N1A—N3A	−176.96 (11)	C7B—C8B—N3B—N1B	3.1 (2)
C2A—C3A—N2A—C4A	−1.7 (2)	C9B—C8B—N3B—N1B	−175.48 (14)
C5A—C4A—N2A—C3A	1.4 (2)	C6B—N1B—N3B—C8B	177.84 (13)
C7A—C8A—N3A—N1A	1.9 (2)	C15B—C10B—C11B—C12B	−1.0 (2)
C9A—C8A—N3A—N1A	−177.37 (16)	C16B—C10B—C11B—C12B	178.41 (13)
C6A—N1A—N3A—C8A	−177.56 (14)	C10B—C11B—C12B—C13B	0.4 (2)
C15A—C10A—C11A—C12A	−0.4 (2)	C11B—C12B—C13B—C14B	0.2 (2)
C16A—C10A—C11A—C12A	177.79 (13)	C11B—C12B—C13B—C17B	−179.67 (13)
C10A—C11A—C12A—C13A	−0.7 (2)	C12B—C13B—C14B—C15B	−0.1 (2)
C11A—C12A—C13A—C14A	1.4 (2)	C17B—C13B—C14B—C15B	179.71 (13)
C11A—C12A—C13A—C17A	−178.12 (13)	C13B—C14B—C15B—C10B	−0.5 (2)
C12A—C13A—C14A—C15A	−1.0 (2)	C11B—C10B—C15B—C14B	1.1 (2)
C17A—C13A—C14A—C15A	178.52 (13)	C16B—C10B—C15B—C14B	−178.38 (13)
C11A—C10A—C15A—C14A	0.8 (2)	C15B—C10B—C16B—O3B	−5.5 (2)
C16A—C10A—C15A—C14A	−177.43 (13)	C11B—C10B—C16B—O3B	175.02 (14)
C13A—C14A—C15A—C10A	−0.1 (2)	C15B—C10B—C16B—O2B	173.41 (13)
C15A—C10A—C16A—O3A	−3.4 (2)	C11B—C10B—C16B—O2B	−6.03 (19)
C11A—C10A—C16A—O3A	178.40 (14)	C12B—C13B—C17B—C23B	−129.6 (8)
C15A—C10A—C16A—O2A	175.95 (12)	C14B—C13B—C17B—C23B	50.6 (8)
C11A—C10A—C16A—O2A	−2.23 (18)	C12B—C13B—C17B—C19B	71.3 (5)
C14A—C13A—C17A—C18A	−3.16 (19)	C14B—C13B—C17B—C19B	−108.5 (5)
C12A—C13A—C17A—C18A	176.34 (13)	C12B—C13B—C17B—C22B	114.1 (6)
C14A—C13A—C17A—C19A	−123.76 (14)	C14B—C13B—C17B—C22B	−65.7 (6)
C12A—C13A—C17A—C19A	55.74 (16)	C12B—C13B—C17B—C21B	1.7 (7)
C14A—C13A—C17A—C20A	117.32 (15)	C14B—C13B—C17B—C21B	−178.2 (7)
C12A—C13A—C17A—C20A	−63.18 (17)	C12B—C13B—C17B—C20B	−51.6 (3)
C5B—C1B—C2B—C3B	2.0 (2)	C14B—C13B—C17B—C20B	128.5 (3)
C6B—C1B—C2B—C3B	178.18 (14)	C12B—C13B—C17B—C18B	−168.5 (4)
C1B—C2B—C3B—N2B	−0.5 (3)	C14B—C13B—C17B—C18B	11.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1B	0.892 (19)	2.14 (2)	3.0149 (16)	167.1 (17)
O2A—H2A···N2A	1.00 (2)	1.72 (3)	2.7168 (15)	172 (2)
N1B—H1B···O1A^i	0.902 (19)	2.162 (19)	3.0362 (16)	163.0 (16)
O2B—H2B···N2B	0.97 (3)	1.68 (3)	2.6326 (16)	169 (2)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

4-tert-Butylbenzoic acid–N'-(butan-2-ylidene)pyridine-4-carbohydrazide (1/1) (III)

Crystal data

C10H13N3O·C11H14O2	F(000) = 1584
Mr = 369.45	Dx = 1.201 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8134 reflections
a = 14.7663 (4) Å	θ = 2.2–26.7°
b = 13.7022 (4) Å	µ = 0.08 mm^−1
c = 20.4647 (6) Å	T = 173 K
β = 99.279 (2)°	Block, colourless
V = 4086.5 (2) Å^3	0.46 × 0.42 × 0.24 mm
Z = 8

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	5703 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −17→17
Tmin = 0.9, Tmax = 0.95	k = −16→16
39826 measured reflections	l = −24→24
7616 independent reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.196	w = 1/[σ^2(Fo^2) + (0.1177P)^2 + 2.7917P] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.033
7616 reflections	Δρmax = 1.12 e Å^−3
541 parameters	Δρmin = −0.43 e Å^−3
99 restraints

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.28601 (15)	−0.09295 (15)	0.22633 (11)	0.0328 (5)
C2A	0.25233 (16)	−0.05148 (17)	0.16550 (12)	0.0370 (5)
H2A1	0.271	−0.075274	0.126149	0.044*
C3A	0.19108 (16)	0.02514 (17)	0.16318 (13)	0.0404 (6)
H3A	0.168121	0.052943	0.121255	0.048*
C4A	0.19392 (17)	0.02030 (18)	0.27486 (13)	0.0419 (6)
H4A	0.17384	0.045116	0.313442	0.05*
C5A	0.25406 (16)	−0.05708 (17)	0.28152 (12)	0.0386 (5)
H5A	0.273512	−0.08566	0.323744	0.046*
C6A	0.35156 (16)	−0.17714 (16)	0.23492 (12)	0.0372 (5)
C7A	0.5314 (2)	−0.2018 (2)	0.09980 (16)	0.0603 (8)
H7A1	0.469957	−0.188722	0.075209	0.09*
H7A2	0.569297	−0.231926	0.070211	0.09*
H7A3	0.559596	−0.140376	0.117145	0.09*
C8A	0.5240 (2)	−0.2700 (2)	0.15641 (18)	0.0588 (8)
C9A	0.5848 (2)	−0.3588 (3)	0.1660 (3)	0.0853 (12)
H9A1	0.645062	−0.342506	0.153443	0.102*
H9A2	0.595356	−0.376832	0.213465	0.102*
C10A	0.5469 (3)	−0.4400 (3)	0.1280 (3)	0.0984 (15)
H10A	0.490215	−0.46057	0.143264	0.148*
H10B	0.590995	−0.493994	0.13345	0.148*
H10C	0.533223	−0.421563	0.081223	0.148*
N1A	0.40996 (13)	−0.18226 (14)	0.19109 (12)	0.0403 (5)
N2A	0.16235 (13)	0.06228 (14)	0.21656 (10)	0.0397 (5)
N3A	0.46986 (16)	−0.26122 (16)	0.19866 (15)	0.0577 (7)
O1A	0.34784 (13)	−0.23703 (13)	0.27881 (9)	0.0507 (5)
H1A	0.4187 (19)	−0.130 (2)	0.1650 (14)	0.049 (8)*
C11A	0.07619 (14)	0.38611 (16)	0.13435 (11)	0.0336 (5)
C12A	0.04217 (15)	0.43553 (17)	0.18472 (12)	0.0355 (5)
H12A	0.029835	0.400733	0.222466	0.043*
C13A	0.02625 (15)	0.53492 (17)	0.18011 (11)	0.0348 (5)
H13A	0.003261	0.567362	0.215055	0.042*
C14A	0.04312 (15)	0.58891 (16)	0.12536 (11)	0.0328 (5)
C15A	0.07625 (16)	0.53830 (17)	0.07528 (12)	0.0374 (5)
H15A	0.087868	0.572734	0.037197	0.045*
C16A	0.09278 (16)	0.43848 (17)	0.07964 (12)	0.0372 (5)
H16A	0.115687	0.405851	0.044735	0.045*
C17A	0.09786 (16)	0.28008 (17)	0.13867 (12)	0.0365 (5)
C18A	0.02548 (17)	0.69924 (17)	0.12303 (12)	0.0381 (5)
C19A	0.0507 (2)	0.74624 (19)	0.06083 (15)	0.0566 (7)
H19A	0.115869	0.735086	0.059332	0.085*
H19B	0.013581	0.717276	0.021598	0.085*
H19C	0.038786	0.816562	0.061595	0.085*
C20A	0.0821 (2)	0.7476 (2)	0.18399 (15)	0.0551 (7)
H20A	0.066476	0.717994	0.224298	0.083*
H20B	0.147619	0.738197	0.182814	0.083*
H20C	0.068388	0.817633	0.183746	0.083*
C21A	−0.07665 (19)	0.71774 (19)	0.12415 (16)	0.0509 (7)
H21A	−0.094025	0.687969	0.163874	0.076*
H21B	−0.088005	0.788185	0.124645	0.076*
H21C	−0.11321	0.688899	0.084648	0.076*
O2A	0.07686 (13)	0.23763 (13)	0.19274 (9)	0.0481 (5)
O3A	0.13252 (13)	0.23617 (13)	0.09770 (9)	0.0478 (5)
H2A	0.102 (2)	0.170 (3)	0.1977 (17)	0.077 (10)*
C1B	0.44880 (16)	0.17139 (16)	0.10357 (11)	0.0351 (5)
C2B	0.51428 (17)	0.24027 (16)	0.09418 (12)	0.0387 (5)
H2B1	0.577555	0.228453	0.109426	0.046*
C3B	0.48598 (18)	0.32580 (18)	0.06245 (13)	0.0437 (6)
H3B	0.531267	0.3723	0.055645	0.052*
C4B	0.33542 (18)	0.27999 (18)	0.04846 (13)	0.0434 (6)
H4B	0.272747	0.293624	0.032231	0.052*
C5B	0.35754 (17)	0.19165 (18)	0.07906 (12)	0.0408 (6)
H5B	0.311013	0.145289	0.083324	0.049*
C6B	0.47203 (15)	0.07472 (16)	0.13630 (12)	0.0341 (5)
C7B	0.7033 (2)	0.0574 (2)	0.28530 (16)	0.0616 (8)
H7B1	0.696336	0.111144	0.253273	0.092*
H7B2	0.765457	0.030642	0.289372	0.092*
H7B3	0.69272	0.081706	0.328484	0.092*
C8B	0.6350 (2)	−0.02073 (19)	0.26207 (13)	0.0492 (7)
C9B	0.6533 (3)	−0.1190 (2)	0.29268 (18)	0.0746 (10)
H9B1	0.682023	−0.11136	0.339575	0.09*
H9B2	0.594586	−0.154215	0.291622	0.09*
C10B	0.7138 (3)	−0.1760 (3)	0.2577 (3)	0.1082 (17)
H10D	0.684911	−0.184909	0.211535	0.162*
H10E	0.725008	−0.239942	0.278986	0.162*
H10F	0.772286	−0.141561	0.259136	0.162*
N1B	0.54379 (14)	0.07407 (14)	0.18566 (10)	0.0375 (5)
N2B	0.39797 (15)	0.34707 (15)	0.04062 (11)	0.0438 (5)
N3B	0.56381 (15)	−0.01488 (15)	0.21798 (10)	0.0451 (5)
O1B	0.42614 (12)	0.00217 (11)	0.11719 (9)	0.0424 (4)
H1B	0.570 (2)	0.128 (2)	0.2033 (14)	0.052 (8)*
C11B	0.24636 (15)	0.64745 (17)	−0.03681 (11)	0.0344 (5)
C12B	0.29734 (16)	0.72244 (17)	−0.00284 (12)	0.0389 (5)
H12B	0.348854	0.70708	0.02968	0.047*
C13B	0.27399 (17)	0.81886 (17)	−0.01580 (12)	0.0400 (6)
H13B	0.30957	0.868797	0.008208	0.048*
C14B	0.19919 (17)	0.84449 (17)	−0.06345 (11)	0.0371 (5)
C15B	0.14821 (18)	0.76856 (19)	−0.09634 (12)	0.0435 (6)
H15B	0.096598	0.783591	−0.128859	0.052*
C16B	0.17067 (17)	0.67205 (18)	−0.08296 (12)	0.0407 (6)
H16B	0.133758	0.621967	−0.10568	0.049*
C17B	0.27150 (16)	0.54288 (17)	−0.02586 (12)	0.0378 (5)
C18B	0.17408 (19)	0.95175 (19)	−0.07780 (12)	0.0476 (6)
C19B	0.1031 (7)	0.9664 (4)	−0.1375 (4)	0.127 (4)	0.728 (7)
H19D	0.043702	0.942624	−0.128522	0.191*	0.728 (7)
H19E	0.120456	0.930054	−0.174882	0.191*	0.728 (7)
H19F	0.098341	1.035977	−0.148517	0.191*	0.728 (7)
C20B	0.2604 (4)	1.0084 (4)	−0.0899 (5)	0.108 (3)	0.728 (7)
H20D	0.283025	0.980893	−0.128465	0.161*	0.728 (7)
H20E	0.308147	1.002784	−0.05084	0.161*	0.728 (7)
H20F	0.244781	1.077257	−0.098121	0.161*	0.728 (7)
C21B	0.1506 (5)	0.9993 (3)	−0.0172 (2)	0.0777 (18)	0.728 (7)
H21D	0.141766	1.069481	−0.025109	0.117*	0.728 (7)
H21E	0.200715	0.989066	0.019881	0.117*	0.728 (7)
H21F	0.094017	0.970754	−0.006386	0.117*	0.728 (7)
C22B	0.2283 (14)	1.0223 (8)	−0.0309 (8)	0.099 (5)	0.272 (7)
H22A	0.293703	1.006604	−0.026639	0.148*	0.272 (7)
H22B	0.20878	1.017469	0.012523	0.148*	0.272 (7)
H22C	0.217694	1.088786	−0.048042	0.148*	0.272 (7)
C23B	0.0715 (7)	0.9588 (9)	−0.0769 (14)	0.117 (6)	0.272 (7)
H23A	0.058534	0.938191	−0.033498	0.175*	0.272 (7)
H23B	0.038573	0.916378	−0.111318	0.175*	0.272 (7)
H23C	0.051332	1.026442	−0.085301	0.175*	0.272 (7)
C24B	0.1966 (13)	0.9727 (10)	−0.1451 (5)	0.079 (4)	0.272 (7)
H24A	0.182825	1.041221	−0.156412	0.119*	0.272 (7)
H24B	0.159789	0.930481	−0.177758	0.119*	0.272 (7)
H24C	0.261922	0.96026	−0.145188	0.119*	0.272 (7)
O2B	0.35092 (13)	0.53042 (14)	0.01278 (11)	0.0576 (6)
O3B	0.22470 (14)	0.47631 (13)	−0.05062 (11)	0.0569 (5)
H2B	0.362 (2)	0.465 (3)	0.0177 (15)	0.062 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0298 (11)	0.0253 (11)	0.0419 (12)	−0.0030 (9)	0.0016 (9)	0.0038 (9)
C2A	0.0371 (12)	0.0327 (12)	0.0409 (13)	0.0056 (10)	0.0051 (10)	0.0029 (10)
C3A	0.0407 (13)	0.0358 (12)	0.0444 (13)	0.0067 (10)	0.0061 (11)	0.0086 (10)
C4A	0.0427 (13)	0.0388 (13)	0.0454 (14)	0.0028 (11)	0.0108 (11)	0.0008 (11)
C5A	0.0400 (13)	0.0356 (12)	0.0395 (13)	0.0016 (10)	0.0042 (10)	0.0073 (10)
C6A	0.0339 (12)	0.0255 (11)	0.0494 (14)	−0.0003 (9)	−0.0018 (10)	0.0060 (10)
C7A	0.0517 (16)	0.0591 (18)	0.072 (2)	0.0065 (14)	0.0143 (14)	−0.0197 (16)
C8A	0.0414 (15)	0.0361 (14)	0.101 (2)	0.0068 (12)	0.0164 (16)	−0.0043 (15)
C9A	0.060 (2)	0.055 (2)	0.145 (4)	0.0209 (16)	0.028 (2)	−0.002 (2)
C10A	0.073 (2)	0.061 (2)	0.154 (4)	0.0212 (19)	−0.002 (3)	−0.022 (2)
N1A	0.0344 (10)	0.0244 (10)	0.0621 (13)	0.0061 (8)	0.0074 (10)	0.0087 (9)
N2A	0.0373 (10)	0.0339 (10)	0.0492 (12)	0.0058 (8)	0.0106 (9)	0.0054 (9)
N3A	0.0415 (12)	0.0314 (11)	0.101 (2)	0.0125 (9)	0.0154 (13)	0.0143 (12)
O1A	0.0555 (11)	0.0380 (10)	0.0576 (11)	0.0081 (8)	0.0060 (9)	0.0184 (9)
C11A	0.0283 (11)	0.0331 (12)	0.0385 (12)	0.0014 (9)	0.0021 (9)	0.0038 (10)
C12A	0.0336 (12)	0.0349 (12)	0.0383 (12)	0.0027 (10)	0.0062 (10)	0.0070 (10)
C13A	0.0330 (11)	0.0354 (12)	0.0358 (12)	0.0018 (9)	0.0053 (9)	0.0010 (10)
C14A	0.0286 (11)	0.0318 (11)	0.0368 (12)	−0.0022 (9)	0.0013 (9)	0.0012 (9)
C15A	0.0414 (13)	0.0352 (12)	0.0358 (12)	−0.0007 (10)	0.0062 (10)	0.0047 (10)
C16A	0.0376 (12)	0.0369 (12)	0.0368 (12)	0.0019 (10)	0.0056 (10)	−0.0010 (10)
C17A	0.0324 (12)	0.0351 (12)	0.0414 (13)	0.0045 (10)	0.0041 (10)	0.0048 (10)
C18A	0.0410 (13)	0.0303 (12)	0.0438 (13)	−0.0029 (10)	0.0088 (10)	0.0006 (10)
C19A	0.077 (2)	0.0345 (13)	0.0635 (18)	0.0025 (13)	0.0267 (16)	0.0106 (13)
C20A	0.0598 (17)	0.0381 (14)	0.0642 (18)	−0.0110 (13)	0.0006 (14)	−0.0064 (13)
C21A	0.0491 (15)	0.0316 (13)	0.0720 (18)	0.0063 (11)	0.0095 (13)	0.0042 (12)
O2A	0.0554 (11)	0.0366 (10)	0.0567 (11)	0.0145 (8)	0.0220 (9)	0.0141 (8)
O3A	0.0577 (11)	0.0381 (9)	0.0492 (10)	0.0126 (8)	0.0135 (9)	0.0033 (8)
C1B	0.0395 (12)	0.0286 (11)	0.0374 (12)	0.0003 (10)	0.0062 (10)	−0.0026 (9)
C2B	0.0366 (12)	0.0322 (12)	0.0476 (14)	0.0011 (10)	0.0081 (10)	0.0016 (10)
C3B	0.0462 (14)	0.0325 (12)	0.0531 (15)	−0.0030 (11)	0.0105 (12)	0.0038 (11)
C4B	0.0405 (13)	0.0399 (13)	0.0491 (14)	0.0083 (11)	0.0054 (11)	0.0002 (11)
C5B	0.0376 (13)	0.0349 (12)	0.0496 (14)	−0.0005 (10)	0.0064 (11)	0.0003 (11)
C6B	0.0349 (12)	0.0274 (11)	0.0405 (12)	−0.0008 (9)	0.0078 (10)	−0.0029 (9)
C7B	0.0584 (18)	0.0498 (16)	0.0683 (19)	−0.0008 (14)	−0.0144 (15)	−0.0028 (14)
C8B	0.0564 (16)	0.0447 (14)	0.0425 (14)	−0.0049 (12)	−0.0034 (12)	0.0062 (12)
C9B	0.085 (2)	0.0563 (19)	0.071 (2)	−0.0053 (18)	−0.0209 (18)	0.0238 (17)
C10B	0.100 (3)	0.067 (2)	0.137 (4)	0.002 (2)	−0.043 (3)	0.017 (3)
N1B	0.0459 (12)	0.0256 (10)	0.0390 (11)	−0.0040 (9)	0.0003 (9)	−0.0011 (8)
N2B	0.0478 (12)	0.0322 (10)	0.0517 (12)	0.0073 (9)	0.0090 (10)	0.0049 (9)
N3B	0.0564 (13)	0.0331 (11)	0.0425 (12)	−0.0052 (9)	−0.0018 (10)	0.0069 (9)
O1B	0.0426 (9)	0.0290 (8)	0.0525 (10)	−0.0038 (7)	−0.0012 (8)	0.0008 (7)
C11B	0.0322 (11)	0.0364 (12)	0.0356 (12)	0.0019 (9)	0.0087 (9)	0.0012 (9)
C12B	0.0329 (12)	0.0345 (12)	0.0469 (14)	0.0031 (10)	−0.0011 (10)	0.0035 (10)
C13B	0.0403 (13)	0.0338 (12)	0.0442 (13)	−0.0008 (10)	0.0017 (11)	0.0007 (10)
C14B	0.0449 (13)	0.0359 (12)	0.0314 (12)	0.0071 (10)	0.0090 (10)	0.0032 (10)
C15B	0.0442 (14)	0.0453 (14)	0.0384 (13)	0.0107 (11)	−0.0017 (11)	−0.0026 (11)
C16B	0.0379 (13)	0.0411 (13)	0.0417 (13)	0.0030 (10)	0.0024 (10)	−0.0063 (11)
C17B	0.0379 (13)	0.0353 (12)	0.0414 (13)	0.0011 (10)	0.0100 (10)	0.0020 (10)
C18B	0.0653 (16)	0.0381 (13)	0.0388 (13)	0.0132 (12)	0.0062 (12)	0.0085 (10)
C19B	0.192 (7)	0.047 (3)	0.107 (4)	0.040 (4)	−0.086 (5)	0.000 (3)
C20B	0.115 (4)	0.054 (3)	0.167 (8)	0.008 (3)	0.061 (4)	0.044 (4)
C21B	0.132 (5)	0.044 (3)	0.062 (3)	0.039 (3)	0.031 (3)	0.009 (2)
C22B	0.167 (12)	0.037 (6)	0.081 (8)	0.010 (8)	−0.016 (10)	−0.004 (6)
C23B	0.084 (5)	0.036 (6)	0.247 (17)	0.033 (6)	0.075 (8)	0.039 (9)
C24B	0.125 (11)	0.058 (7)	0.058 (5)	0.025 (8)	0.022 (7)	0.034 (5)
O2B	0.0507 (11)	0.0311 (10)	0.0840 (15)	0.0069 (8)	−0.0107 (10)	0.0049 (9)
O3B	0.0566 (12)	0.0350 (10)	0.0746 (14)	−0.0035 (9)	−0.0029 (10)	−0.0048 (9)

Geometric parameters (Å, º)

C1A—C2A	1.386 (3)	C3B—H3B	0.95
C1A—C5A	1.383 (3)	C4B—N2B	1.331 (3)
C1A—C6A	1.498 (3)	C4B—C5B	1.378 (3)
C2A—C3A	1.381 (3)	C4B—H4B	0.95
C2A—H2A1	0.95	C5B—H5B	0.95
C3A—N2A	1.335 (3)	C6B—O1B	1.231 (3)
C3A—H3A	0.95	C6B—N1B	1.341 (3)
C4A—N2A	1.339 (3)	C7B—C8B	1.494 (4)
C4A—C5A	1.376 (3)	C7B—H7B1	0.98
C4A—H4A	0.95	C7B—H7B2	0.98
C5A—H5A	0.95	C7B—H7B3	0.98
C6A—O1A	1.224 (3)	C8B—N3B	1.273 (3)
C6A—N1A	1.343 (3)	C8B—C9B	1.491 (4)
C7A—C8A	1.505 (5)	C9B—C10B	1.459 (7)
C7A—H7A1	0.98	C9B—H9B1	0.99
C7A—H7A2	0.98	C9B—H9B2	0.99
C7A—H7A3	0.98	C10B—H10D	0.98
C8A—N3A	1.275 (4)	C10B—H10E	0.98
C8A—C9A	1.506 (4)	C10B—H10F	0.98
C9A—C10A	1.420 (5)	N1B—N3B	1.396 (3)
C9A—H9A1	0.99	N1B—H1B	0.88 (3)
C9A—H9A2	0.99	C11B—C16B	1.384 (3)
C10A—H10A	0.98	C11B—C12B	1.392 (3)
C10A—H10B	0.98	C11B—C17B	1.488 (3)
C10A—H10C	0.98	C12B—C13B	1.380 (3)
N1A—N3A	1.390 (3)	C12B—H12B	0.95
N1A—H1A	0.91 (3)	C13B—C14B	1.395 (3)
C11A—C16A	1.385 (3)	C13B—H13B	0.95
C11A—C12A	1.393 (3)	C14B—C15B	1.392 (4)
C11A—C17A	1.487 (3)	C14B—C18B	1.533 (3)
C12A—C13A	1.383 (3)	C15B—C16B	1.380 (4)
C12A—H12A	0.95	C15B—H15B	0.95
C13A—C14A	1.398 (3)	C16B—H16B	0.95
C13A—H13A	0.95	C17B—O3B	1.205 (3)
C14A—C15A	1.390 (3)	C17B—O2B	1.316 (3)
C14A—C18A	1.533 (3)	C18B—C19B	1.490 (5)
C15A—C16A	1.390 (3)	C18B—C21B	1.491 (4)
C15A—H15A	0.95	C18B—C22B	1.498 (7)
C16A—H16A	0.95	C18B—C24B	1.496 (7)
C17A—O3A	1.211 (3)	C18B—C23B	1.521 (7)
C17A—O2A	1.330 (3)	C18B—C20B	1.546 (5)
C18A—C19A	1.525 (4)	C19B—H19D	0.98
C18A—C21A	1.533 (4)	C19B—H19E	0.98
C18A—C20A	1.536 (4)	C19B—H19F	0.98
C19A—H19A	0.98	C20B—H20D	0.98
C19A—H19B	0.98	C20B—H20E	0.98
C19A—H19C	0.98	C20B—H20F	0.98
C20A—H20A	0.98	C21B—H21D	0.98
C20A—H20B	0.98	C21B—H21E	0.98
C20A—H20C	0.98	C21B—H21F	0.98
C21A—H21A	0.98	C22B—H22A	0.98
C21A—H21B	0.98	C22B—H22B	0.98
C21A—H21C	0.98	C22B—H22C	0.98
O2A—H2A	0.99 (4)	C23B—H23A	0.98
C1B—C2B	1.387 (3)	C23B—H23B	0.98
C1B—C5B	1.388 (3)	C23B—H23C	0.98
C1B—C6B	1.499 (3)	C24B—H24A	0.98
C2B—C3B	1.372 (3)	C24B—H24B	0.98
C2B—H2B1	0.95	C24B—H24C	0.98
C3B—N2B	1.336 (3)	O2B—H2B	0.91 (3)
C2A—C1A—C5A	117.9 (2)	C4B—C5B—C1B	119.0 (2)
C2A—C1A—C6A	123.6 (2)	C4B—C5B—H5B	120.5
C5A—C1A—C6A	118.5 (2)	C1B—C5B—H5B	120.5
C3A—C2A—C1A	118.7 (2)	O1B—C6B—N1B	124.2 (2)
C3A—C2A—H2A1	120.6	O1B—C6B—C1B	119.8 (2)
C1A—C2A—H2A1	120.6	N1B—C6B—C1B	116.02 (19)
N2A—C3A—C2A	123.7 (2)	C8B—C7B—H7B1	109.5
N2A—C3A—H3A	118.2	C8B—C7B—H7B2	109.5
C2A—C3A—H3A	118.2	H7B1—C7B—H7B2	109.5
N2A—C4A—C5A	123.1 (2)	C8B—C7B—H7B3	109.5
N2A—C4A—H4A	118.5	H7B1—C7B—H7B3	109.5
C5A—C4A—H4A	118.5	H7B2—C7B—H7B3	109.5
C4A—C5A—C1A	119.5 (2)	N3B—C8B—C7B	128.2 (2)
C4A—C5A—H5A	120.2	N3B—C8B—C9B	115.3 (2)
C1A—C5A—H5A	120.2	C7B—C8B—C9B	116.5 (2)
O1A—C6A—N1A	124.4 (2)	C10B—C9B—C8B	111.2 (3)
O1A—C6A—C1A	119.9 (2)	C10B—C9B—H9B1	109.4
N1A—C6A—C1A	115.7 (2)	C8B—C9B—H9B1	109.4
C8A—C7A—H7A1	109.5	C10B—C9B—H9B2	109.4
C8A—C7A—H7A2	109.5	C8B—C9B—H9B2	109.4
H7A1—C7A—H7A2	109.5	H9B1—C9B—H9B2	108
C8A—C7A—H7A3	109.5	C9B—C10B—H10D	109.5
H7A1—C7A—H7A3	109.5	C9B—C10B—H10E	109.5
H7A2—C7A—H7A3	109.5	H10D—C10B—H10E	109.5
N3A—C8A—C7A	126.5 (2)	C9B—C10B—H10F	109.5
N3A—C8A—C9A	114.4 (3)	H10D—C10B—H10F	109.5
C7A—C8A—C9A	119.1 (3)	H10E—C10B—H10F	109.5
C10A—C9A—C8A	112.8 (3)	C6B—N1B—N3B	116.37 (19)
C10A—C9A—H9A1	109	C6B—N1B—H1B	122.9 (19)
C8A—C9A—H9A1	109	N3B—N1B—H1B	119.4 (19)
C10A—C9A—H9A2	109	C4B—N2B—C3B	117.7 (2)
C8A—C9A—H9A2	109	C8B—N3B—N1B	118.6 (2)
H9A1—C9A—H9A2	107.8	C16B—C11B—C12B	118.3 (2)
C9A—C10A—H10A	109.5	C16B—C11B—C17B	119.5 (2)
C9A—C10A—H10B	109.5	C12B—C11B—C17B	122.3 (2)
H10A—C10A—H10B	109.5	C13B—C12B—C11B	120.8 (2)
C9A—C10A—H10C	109.5	C13B—C12B—H12B	119.6
H10A—C10A—H10C	109.5	C11B—C12B—H12B	119.6
H10B—C10A—H10C	109.5	C12B—C13B—C14B	121.4 (2)
C6A—N1A—N3A	115.6 (2)	C12B—C13B—H13B	119.3
C6A—N1A—H1A	121.1 (18)	C14B—C13B—H13B	119.3
N3A—N1A—H1A	121.8 (18)	C15B—C14B—C13B	117.1 (2)
C3A—N2A—C4A	117.0 (2)	C15B—C14B—C18B	121.9 (2)
C8A—N3A—N1A	117.1 (2)	C13B—C14B—C18B	121.0 (2)
C16A—C11A—C12A	118.6 (2)	C16B—C15B—C14B	121.7 (2)
C16A—C11A—C17A	119.3 (2)	C16B—C15B—H15B	119.1
C12A—C11A—C17A	122.0 (2)	C14B—C15B—H15B	119.1
C13A—C12A—C11A	120.4 (2)	C15B—C16B—C11B	120.7 (2)
C13A—C12A—H12A	119.8	C15B—C16B—H16B	119.6
C11A—C12A—H12A	119.8	C11B—C16B—H16B	119.6
C12A—C13A—C14A	121.7 (2)	O3B—C17B—O2B	123.3 (2)
C12A—C13A—H13A	119.1	O3B—C17B—C11B	123.6 (2)
C14A—C13A—H13A	119.1	O2B—C17B—C11B	113.1 (2)
C15A—C14A—C13A	117.1 (2)	C19B—C18B—C21B	113.4 (5)
C15A—C14A—C18A	123.2 (2)	C22B—C18B—C24B	106.9 (11)
C13A—C14A—C18A	119.7 (2)	C19B—C18B—C14B	113.7 (3)
C16A—C15A—C14A	121.5 (2)	C21B—C18B—C14B	110.0 (2)
C16A—C15A—H15A	119.2	C22B—C18B—C14B	114.1 (6)
C14A—C15A—H15A	119.2	C24B—C18B—C14B	106.1 (5)
C11A—C16A—C15A	120.7 (2)	C22B—C18B—C23B	112.4 (13)
C11A—C16A—H16A	119.7	C24B—C18B—C23B	111.6 (12)
C15A—C16A—H16A	119.7	C14B—C18B—C23B	105.6 (5)
O3A—C17A—O2A	122.7 (2)	C19B—C18B—C20B	106.9 (5)
O3A—C17A—C11A	123.7 (2)	C21B—C18B—C20B	102.8 (4)
O2A—C17A—C11A	113.6 (2)	C14B—C18B—C20B	109.4 (3)
C19A—C18A—C21A	108.4 (2)	C18B—C19B—H19D	109.5
C19A—C18A—C14A	112.3 (2)	C18B—C19B—H19E	109.5
C21A—C18A—C14A	108.97 (19)	H19D—C19B—H19E	109.5
C19A—C18A—C20A	108.7 (2)	C18B—C19B—H19F	109.5
C21A—C18A—C20A	108.9 (2)	H19D—C19B—H19F	109.5
C14A—C18A—C20A	109.4 (2)	H19E—C19B—H19F	109.5
C18A—C19A—H19A	109.5	C18B—C20B—H20D	109.5
C18A—C19A—H19B	109.5	C18B—C20B—H20E	109.5
H19A—C19A—H19B	109.5	H20D—C20B—H20E	109.5
C18A—C19A—H19C	109.5	C18B—C20B—H20F	109.5
H19A—C19A—H19C	109.5	H20D—C20B—H20F	109.5
H19B—C19A—H19C	109.5	H20E—C20B—H20F	109.5
C18A—C20A—H20A	109.5	C18B—C21B—H21D	109.5
C18A—C20A—H20B	109.5	C18B—C21B—H21E	109.5
H20A—C20A—H20B	109.5	H21D—C21B—H21E	109.5
C18A—C20A—H20C	109.5	C18B—C21B—H21F	109.5
H20A—C20A—H20C	109.5	H21D—C21B—H21F	109.5
H20B—C20A—H20C	109.5	H21E—C21B—H21F	109.5
C18A—C21A—H21A	109.5	C18B—C22B—H22A	109.5
C18A—C21A—H21B	109.5	C18B—C22B—H22B	109.5
H21A—C21A—H21B	109.5	H22A—C22B—H22B	109.5
C18A—C21A—H21C	109.5	C18B—C22B—H22C	109.5
H21A—C21A—H21C	109.5	H22A—C22B—H22C	109.5
H21B—C21A—H21C	109.5	H22B—C22B—H22C	109.5
C17A—O2A—H2A	111 (2)	C18B—C23B—H23A	109.5
C2B—C1B—C5B	118.2 (2)	C18B—C23B—H23B	109.4
C2B—C1B—C6B	123.3 (2)	H23A—C23B—H23B	109.5
C5B—C1B—C6B	118.5 (2)	C18B—C23B—H23C	109.5
C3B—C2B—C1B	118.8 (2)	H23A—C23B—H23C	109.5
C3B—C2B—H2B1	120.6	H23B—C23B—H23C	109.5
C1B—C2B—H2B1	120.6	C18B—C24B—H24A	109.5
N2B—C3B—C2B	123.4 (2)	C18B—C24B—H24B	109.5
N2B—C3B—H3B	118.3	H24A—C24B—H24B	109.5
C2B—C3B—H3B	118.3	C18B—C24B—H24C	109.5
N2B—C4B—C5B	122.9 (2)	H24A—C24B—H24C	109.5
N2B—C4B—H4B	118.5	H24B—C24B—H24C	109.5
C5B—C4B—H4B	118.5	C17B—O2B—H2B	109 (2)
C5A—C1A—C2A—C3A	2.0 (3)	N2B—C4B—C5B—C1B	0.7 (4)
C6A—C1A—C2A—C3A	179.1 (2)	C2B—C1B—C5B—C4B	−2.0 (4)
C1A—C2A—C3A—N2A	0.3 (4)	C6B—C1B—C5B—C4B	−179.5 (2)
N2A—C4A—C5A—C1A	1.6 (4)	C2B—C1B—C6B—O1B	−144.9 (2)
C2A—C1A—C5A—C4A	−2.8 (3)	C5B—C1B—C6B—O1B	32.5 (3)
C6A—C1A—C5A—C4A	179.9 (2)	C2B—C1B—C6B—N1B	34.9 (3)
C2A—C1A—C6A—O1A	−147.1 (2)	C5B—C1B—C6B—N1B	−147.7 (2)
C5A—C1A—C6A—O1A	30.0 (3)	N3B—C8B—C9B—C10B	92.2 (4)
C2A—C1A—C6A—N1A	31.1 (3)	C7B—C8B—C9B—C10B	−86.1 (4)
C5A—C1A—C6A—N1A	−151.8 (2)	O1B—C6B—N1B—N3B	−2.4 (4)
N3A—C8A—C9A—C10A	93.3 (5)	C1B—C6B—N1B—N3B	177.8 (2)
C7A—C8A—C9A—C10A	−86.3 (4)	C5B—C4B—N2B—C3B	1.4 (4)
O1A—C6A—N1A—N3A	−1.1 (4)	C2B—C3B—N2B—C4B	−2.2 (4)
C1A—C6A—N1A—N3A	−179.2 (2)	C7B—C8B—N3B—N1B	0.1 (5)
C2A—C3A—N2A—C4A	−1.6 (4)	C9B—C8B—N3B—N1B	−178.1 (3)
C5A—C4A—N2A—C3A	0.7 (4)	C6B—N1B—N3B—C8B	175.2 (2)
C7A—C8A—N3A—N1A	1.6 (5)	C16B—C11B—C12B—C13B	−1.2 (4)
C9A—C8A—N3A—N1A	−178.0 (3)	C17B—C11B—C12B—C13B	177.8 (2)
C6A—N1A—N3A—C8A	177.7 (3)	C11B—C12B—C13B—C14B	−0.4 (4)
C16A—C11A—C12A—C13A	−0.6 (3)	C12B—C13B—C14B—C15B	1.2 (4)
C17A—C11A—C12A—C13A	177.4 (2)	C12B—C13B—C14B—C18B	−179.6 (2)
C11A—C12A—C13A—C14A	0.2 (3)	C13B—C14B—C15B—C16B	−0.4 (4)
C12A—C13A—C14A—C15A	0.3 (3)	C18B—C14B—C15B—C16B	−179.6 (2)
C12A—C13A—C14A—C18A	−179.2 (2)	C14B—C15B—C16B—C11B	−1.2 (4)
C13A—C14A—C15A—C16A	−0.6 (3)	C12B—C11B—C16B—C15B	2.0 (4)
C18A—C14A—C15A—C16A	179.0 (2)	C17B—C11B—C16B—C15B	−177.0 (2)
C12A—C11A—C16A—C15A	0.3 (3)	C16B—C11B—C17B—O3B	−7.1 (4)
C17A—C11A—C16A—C15A	−177.7 (2)	C12B—C11B—C17B—O3B	173.9 (3)
C14A—C15A—C16A—C11A	0.3 (4)	C16B—C11B—C17B—O2B	171.8 (2)
C16A—C11A—C17A—O3A	2.5 (3)	C12B—C11B—C17B—O2B	−7.2 (3)
C12A—C11A—C17A—O3A	−175.5 (2)	C15B—C14B—C18B—C19B	−10.9 (6)
C16A—C11A—C17A—O2A	−178.5 (2)	C13B—C14B—C18B—C19B	170.0 (5)
C12A—C11A—C17A—O2A	3.5 (3)	C15B—C14B—C18B—C21B	117.5 (4)
C15A—C14A—C18A—C19A	−1.4 (3)	C13B—C14B—C18B—C21B	−61.6 (4)
C13A—C14A—C18A—C19A	178.1 (2)	C15B—C14B—C18B—C22B	171.6 (11)
C15A—C14A—C18A—C21A	118.7 (2)	C13B—C14B—C18B—C22B	−7.5 (11)
C13A—C14A—C18A—C21A	−61.8 (3)	C15B—C14B—C18B—C24B	−71.0 (8)
C15A—C14A—C18A—C20A	−122.3 (2)	C13B—C14B—C18B—C24B	109.9 (8)
C13A—C14A—C18A—C20A	57.2 (3)	C15B—C14B—C18B—C23B	47.6 (12)
C5B—C1B—C2B—C3B	1.3 (4)	C13B—C14B—C18B—C23B	−131.5 (12)
C6B—C1B—C2B—C3B	178.7 (2)	C15B—C14B—C18B—C20B	−130.3 (4)
C1B—C2B—C3B—N2B	0.8 (4)	C13B—C14B—C18B—C20B	50.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1B	0.91 (3)	2.07 (3)	2.974 (3)	170 (3)
O2A—H2A···N2A	0.99 (4)	1.74 (4)	2.721 (3)	169 (3)
N1B—H1B···N3A^i	0.88 (3)	2.66 (3)	3.300 (3)	131 (2)
N1B—H1B···O1A^i	0.88 (3)	2.21 (3)	3.068 (3)	164 (3)
O2B—H2B···N2B	0.91 (3)	1.75 (4)	2.644 (3)	169 (3)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

4-tert-Butylbenzoic acid–N'-(diphenylmethylene)pyridine-4-carbohydrazide (1/1) (IV)

Crystal data

C19H15N3O·C11H14O2	F(000) = 508
Mr = 479.56	Dx = 1.271 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6555 reflections
a = 7.6967 (1) Å	θ = 2.4–28.3°
b = 10.1984 (2) Å	µ = 0.08 mm^−1
c = 15.9931 (3) Å	T = 173 K
β = 93.505 (1)°	Blocks, colourless
V = 1253.01 (4) Å^3	0.46 × 0.37 × 0.25 mm
Z = 2

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	5107 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 28.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
Tmin = 0.9, Tmax = 0.95	k = −13→9
12710 measured reflections	l = −21→20
5486 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0496P)^2 + 0.1553P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.27 e Å^−3
5486 reflections	Δρmin = −0.18 e Å^−3
336 parameters	Absolute structure: The low value of Friedif(stat), 4.9, indicates that the absolute structure cannot be reliably determined on the basis of the diffraction data." Flack, H. D. & Bernardinelli, G. (2008). Acta Cryst. A64, 484-493. Flack, H. D. & Shmueli, U. (2007). Acta Cryst. A63, 257-265. (Equation 8).
1 restraint	Absolute structure parameter: 0.5 (4)
0 constraints

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.

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

	x	y	z	Uiso*/Ueq
C1	0.6969 (2)	0.27150 (19)	0.18498 (11)	0.0263 (4)
C2	0.6453 (3)	0.3508 (2)	0.24900 (12)	0.0324 (4)
H2A	0.719547	0.418296	0.271281	0.039*
C3	0.4831 (3)	0.3302 (2)	0.28020 (13)	0.0361 (5)
H3	0.449082	0.384506	0.324617	0.043*
C4	0.4224 (3)	0.1635 (2)	0.18812 (13)	0.0384 (5)
H4	0.343759	0.098877	0.165765	0.046*
C5	0.5821 (3)	0.1755 (2)	0.15401 (12)	0.0361 (5)
H5	0.613084	0.119084	0.110064	0.043*
C6	0.8715 (2)	0.27944 (19)	0.14762 (11)	0.0270 (4)
C7	1.1789 (2)	0.52887 (19)	0.12433 (11)	0.0251 (4)
C8	1.0989 (2)	0.65272 (19)	0.15428 (11)	0.0251 (4)
C9	1.0645 (2)	0.6698 (2)	0.23819 (12)	0.0323 (4)
H9	1.081815	0.599473	0.276759	0.039*
C10	1.0047 (3)	0.7906 (3)	0.26507 (14)	0.0415 (5)
H10	0.983292	0.802993	0.32241	0.05*
C11	0.9763 (3)	0.8927 (2)	0.20905 (16)	0.0418 (5)
H11	0.936382	0.975036	0.227995	0.05*
C12	1.0060 (3)	0.8748 (2)	0.12520 (15)	0.0360 (5)
H12	0.983571	0.944218	0.086401	0.043*
C13	1.0682 (2)	0.7559 (2)	0.09798 (12)	0.0296 (4)
H13	1.090221	0.744456	0.040635	0.035*
C14	1.3546 (2)	0.53948 (19)	0.09080 (11)	0.0259 (4)
C15	1.4121 (3)	0.4462 (2)	0.03529 (12)	0.0304 (4)
H15	1.338428	0.374981	0.01839	0.037*
C16	1.5765 (3)	0.4563 (2)	0.00439 (13)	0.0346 (4)
H16	1.61441	0.392655	−0.03383	0.042*
C17	1.6851 (2)	0.5594 (2)	0.02930 (12)	0.0344 (5)
H17	1.796607	0.567079	0.007398	0.041*
C18	1.6313 (2)	0.6509 (2)	0.08599 (12)	0.0324 (4)
H18	1.707136	0.719914	0.104431	0.039*
C19	1.4656 (2)	0.6418 (2)	0.11604 (12)	0.0289 (4)
H19	1.428074	0.705862	0.15408	0.035*
N1	0.9513 (2)	0.39894 (17)	0.15531 (10)	0.0274 (3)
N2	0.3731 (2)	0.23812 (19)	0.25089 (11)	0.0336 (4)
N3	1.1126 (2)	0.41337 (17)	0.12414 (10)	0.0278 (3)
O1	0.9334 (2)	0.18616 (15)	0.11321 (10)	0.0380 (3)
H1	0.894 (3)	0.465 (2)	0.1747 (14)	0.031 (6)*
C20	−0.0900 (3)	0.3101 (2)	0.43188 (12)	0.0320 (4)
C21	−0.1868 (3)	0.1970 (2)	0.44003 (15)	0.0446 (5)
H21	−0.163068	0.121764	0.4076	0.053*
C22	−0.3180 (3)	0.1934 (3)	0.49538 (16)	0.0460 (6)
H22	−0.383633	0.115051	0.49986	0.055*
C23	−0.3572 (3)	0.3002 (2)	0.54458 (12)	0.0320 (4)
C24	−0.2586 (3)	0.4129 (2)	0.53582 (13)	0.0378 (5)
H24	−0.28129	0.487897	0.568635	0.045*
C25	−0.1273 (3)	0.4178 (2)	0.47983 (13)	0.0368 (4)
H25	−0.062486	0.496368	0.47456	0.044*
C26	0.0529 (3)	0.3195 (2)	0.37310 (12)	0.0333 (4)
C27	−0.5099 (3)	0.2937 (2)	0.60171 (12)	0.0342 (4)
C28	−0.4999 (3)	0.4016 (3)	0.66821 (15)	0.0478 (6)
H28A	−0.511509	0.487433	0.64089	0.072*
H28B	−0.387568	0.396656	0.700372	0.072*
H28C	−0.594254	0.389866	0.706	0.072*
C29	−0.6786 (3)	0.3087 (3)	0.54581 (15)	0.0432 (5)
H29A	−0.686045	0.238005	0.504232	0.065*
H29B	−0.678186	0.393559	0.517082	0.065*
H29C	−0.779082	0.30406	0.580496	0.065*
C30	−0.5156 (3)	0.1606 (3)	0.64621 (13)	0.0416 (5)
H30A	−0.404822	0.145455	0.678262	0.062*
H30B	−0.53502	0.090897	0.604495	0.062*
H30C	−0.610655	0.160425	0.684288	0.062*
O2	0.0861 (2)	0.20904 (18)	0.33451 (10)	0.0433 (4)
O3	0.1323 (2)	0.42036 (17)	0.36303 (10)	0.0429 (4)
H2	0.171 (4)	0.214 (3)	0.3001 (18)	0.055 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0302 (9)	0.0212 (10)	0.0273 (8)	−0.0022 (7)	0.0001 (7)	0.0043 (7)
C2	0.0343 (10)	0.0273 (11)	0.0356 (9)	−0.0041 (8)	0.0013 (8)	−0.0030 (8)
C3	0.0383 (10)	0.0330 (12)	0.0375 (10)	−0.0019 (9)	0.0066 (8)	−0.0045 (9)
C4	0.0407 (11)	0.0373 (13)	0.0373 (9)	−0.0151 (10)	0.0037 (8)	−0.0034 (9)
C5	0.0411 (10)	0.0341 (12)	0.0338 (9)	−0.0105 (9)	0.0069 (8)	−0.0064 (9)
C6	0.0300 (9)	0.0232 (10)	0.0277 (8)	−0.0028 (7)	0.0010 (7)	0.0027 (7)
C7	0.0243 (8)	0.0224 (10)	0.0287 (8)	0.0015 (7)	0.0012 (6)	0.0021 (7)
C8	0.0200 (7)	0.0210 (9)	0.0344 (8)	−0.0029 (6)	0.0031 (6)	−0.0001 (7)
C9	0.0307 (9)	0.0325 (11)	0.0339 (9)	−0.0018 (8)	0.0049 (7)	0.0015 (8)
C10	0.0403 (11)	0.0442 (14)	0.0413 (11)	−0.0031 (10)	0.0121 (9)	−0.0124 (10)
C11	0.0351 (10)	0.0282 (12)	0.0633 (13)	0.0000 (9)	0.0134 (9)	−0.0109 (11)
C12	0.0304 (10)	0.0226 (11)	0.0557 (12)	−0.0003 (8)	0.0085 (9)	0.0048 (9)
C13	0.0255 (8)	0.0273 (11)	0.0364 (9)	−0.0017 (7)	0.0056 (7)	0.0031 (8)
C14	0.0238 (8)	0.0237 (9)	0.0301 (8)	0.0032 (7)	0.0016 (7)	0.0044 (7)
C15	0.0297 (9)	0.0255 (10)	0.0361 (9)	0.0027 (7)	0.0014 (7)	0.0001 (8)
C16	0.0325 (10)	0.0360 (12)	0.0358 (9)	0.0108 (9)	0.0056 (8)	−0.0001 (8)
C17	0.0238 (9)	0.0427 (13)	0.0371 (9)	0.0057 (8)	0.0052 (7)	0.0085 (9)
C18	0.0255 (9)	0.0316 (11)	0.0399 (10)	−0.0018 (8)	0.0004 (7)	0.0062 (9)
C19	0.0266 (9)	0.0269 (11)	0.0334 (9)	0.0010 (7)	0.0031 (7)	0.0013 (8)
N1	0.0261 (7)	0.0198 (8)	0.0365 (8)	0.0002 (6)	0.0041 (6)	0.0012 (7)
N2	0.0321 (8)	0.0334 (10)	0.0355 (8)	−0.0045 (7)	0.0034 (6)	0.0037 (7)
N3	0.0253 (7)	0.0246 (9)	0.0335 (7)	0.0007 (6)	0.0023 (6)	0.0028 (7)
O1	0.0441 (8)	0.0234 (8)	0.0478 (8)	−0.0029 (6)	0.0139 (6)	−0.0051 (6)
C20	0.0294 (9)	0.0326 (11)	0.0336 (9)	0.0006 (8)	−0.0015 (7)	0.0056 (8)
C21	0.0486 (12)	0.0332 (13)	0.0536 (12)	−0.0063 (10)	0.0162 (10)	−0.0083 (10)
C22	0.0475 (12)	0.0320 (13)	0.0604 (13)	−0.0107 (10)	0.0191 (11)	−0.0068 (11)
C23	0.0315 (9)	0.0322 (11)	0.0320 (9)	0.0021 (8)	0.0006 (7)	0.0034 (8)
C24	0.0426 (11)	0.0297 (12)	0.0412 (10)	0.0005 (9)	0.0038 (8)	−0.0021 (9)
C25	0.0390 (11)	0.0279 (11)	0.0437 (10)	−0.0038 (9)	0.0032 (8)	0.0044 (9)
C26	0.0310 (9)	0.0366 (13)	0.0317 (9)	0.0007 (9)	−0.0020 (7)	0.0077 (9)
C27	0.0349 (10)	0.0345 (12)	0.0333 (9)	0.0009 (9)	0.0034 (8)	0.0019 (8)
C28	0.0528 (13)	0.0470 (15)	0.0447 (11)	−0.0008 (12)	0.0129 (10)	−0.0089 (11)
C29	0.0345 (10)	0.0499 (15)	0.0451 (11)	0.0052 (10)	0.0020 (9)	0.0076 (11)
C30	0.0448 (11)	0.0433 (14)	0.0370 (10)	−0.0002 (10)	0.0036 (9)	0.0102 (10)
O2	0.0402 (8)	0.0415 (10)	0.0498 (8)	−0.0066 (7)	0.0165 (7)	−0.0035 (7)
O3	0.0478 (9)	0.0347 (9)	0.0472 (8)	−0.0044 (7)	0.0108 (7)	0.0088 (7)

Geometric parameters (Å, º)

C1—C2	1.382 (3)	C17—H17	0.95
C1—C5	1.389 (3)	C18—C19	1.393 (2)
C1—C6	1.506 (2)	C18—H18	0.95
C2—C3	1.388 (3)	C19—H19	0.95
C2—H2A	0.95	N1—N3	1.374 (2)
C3—N2	1.331 (3)	N1—H1	0.87 (3)
C3—H3	0.95	C20—C25	1.380 (3)
C4—N2	1.333 (3)	C20—C21	1.383 (3)
C4—C5	1.381 (3)	C20—C26	1.493 (3)
C4—H4	0.95	C21—C22	1.384 (3)
C5—H5	0.95	C21—H21	0.95
C6—O1	1.211 (2)	C22—C23	1.388 (3)
C6—N1	1.367 (3)	C22—H22	0.95
C7—N3	1.284 (3)	C23—C24	1.388 (3)
C7—C14	1.489 (2)	C23—C27	1.534 (3)
C7—C8	1.496 (3)	C24—C25	1.392 (3)
C8—C9	1.394 (3)	C24—H24	0.95
C8—C13	1.396 (3)	C25—H25	0.95
C9—C10	1.393 (3)	C26—O3	1.213 (3)
C9—H9	0.95	C26—O2	1.317 (3)
C10—C11	1.382 (4)	C27—C28	1.529 (3)
C10—H10	0.95	C27—C30	1.535 (3)
C11—C12	1.386 (3)	C27—C29	1.538 (3)
C11—H11	0.95	C28—H28A	0.98
C12—C13	1.384 (3)	C28—H28B	0.98
C12—H12	0.95	C28—H28C	0.98
C13—H13	0.95	C29—H29A	0.98
C14—C15	1.392 (3)	C29—H29B	0.98
C14—C19	1.393 (3)	C29—H29C	0.98
C15—C16	1.390 (3)	C30—H30A	0.98
C15—H15	0.95	C30—H30B	0.98
C16—C17	1.386 (3)	C30—H30C	0.98
C16—H16	0.95	O2—H2	0.88 (3)
C17—C18	1.382 (3)
C2—C1—C5	118.12 (17)	C18—C19—C14	120.57 (18)
C2—C1—C6	124.49 (17)	C18—C19—H19	119.7
C5—C1—C6	117.37 (17)	C14—C19—H19	119.7
C1—C2—C3	118.90 (19)	C6—N1—N3	118.30 (16)
C1—C2—H2A	120.6	C6—N1—H1	119.1 (16)
C3—C2—H2A	120.6	N3—N1—H1	122.2 (16)
N2—C3—C2	123.16 (19)	C3—N2—C4	117.64 (17)
N2—C3—H3	118.4	C7—N3—N1	117.72 (16)
C2—C3—H3	118.4	C25—C20—C21	118.70 (18)
N2—C4—C5	123.2 (2)	C25—C20—C26	119.02 (19)
N2—C4—H4	118.4	C21—C20—C26	122.3 (2)
C5—C4—H4	118.4	C20—C21—C22	120.0 (2)
C4—C5—C1	118.92 (19)	C20—C21—H21	120
C4—C5—H5	120.5	C22—C21—H21	120
C1—C5—H5	120.5	C21—C22—C23	122.3 (2)
O1—C6—N1	123.65 (17)	C21—C22—H22	118.9
O1—C6—C1	121.55 (17)	C23—C22—H22	118.9
N1—C6—C1	114.80 (16)	C22—C23—C24	116.98 (18)
N3—C7—C14	115.80 (17)	C22—C23—C27	120.3 (2)
N3—C7—C8	127.17 (16)	C24—C23—C27	122.63 (19)
C14—C7—C8	117.03 (16)	C23—C24—C25	121.2 (2)
C9—C8—C13	119.47 (18)	C23—C24—H24	119.4
C9—C8—C7	121.30 (17)	C25—C24—H24	119.4
C13—C8—C7	119.11 (16)	C20—C25—C24	120.8 (2)
C10—C9—C8	119.57 (19)	C20—C25—H25	119.6
C10—C9—H9	120.2	C24—C25—H25	119.6
C8—C9—H9	120.2	O3—C26—O2	123.33 (18)
C11—C10—C9	120.57 (19)	O3—C26—C20	122.3 (2)
C11—C10—H10	119.7	O2—C26—C20	114.34 (19)
C9—C10—H10	119.7	C28—C27—C23	112.04 (18)
C10—C11—C12	119.9 (2)	C28—C27—C30	108.40 (18)
C10—C11—H11	120	C23—C27—C30	111.06 (18)
C12—C11—H11	120	C28—C27—C29	109.7 (2)
C13—C12—C11	120.0 (2)	C23—C27—C29	107.45 (16)
C13—C12—H12	120	C30—C27—C29	108.09 (19)
C11—C12—H12	120	C27—C28—H28A	109.5
C12—C13—C8	120.40 (18)	C27—C28—H28B	109.5
C12—C13—H13	119.8	H28A—C28—H28B	109.5
C8—C13—H13	119.8	C27—C28—H28C	109.5
C15—C14—C19	118.91 (17)	H28A—C28—H28C	109.5
C15—C14—C7	120.75 (18)	H28B—C28—H28C	109.5
C19—C14—C7	120.33 (17)	C27—C29—H29A	109.5
C16—C15—C14	120.49 (19)	C27—C29—H29B	109.5
C16—C15—H15	119.8	H29A—C29—H29B	109.5
C14—C15—H15	119.8	C27—C29—H29C	109.5
C17—C16—C15	120.04 (19)	H29A—C29—H29C	109.5
C17—C16—H16	120	H29B—C29—H29C	109.5
C15—C16—H16	120	C27—C30—H30A	109.5
C18—C17—C16	120.06 (17)	C27—C30—H30B	109.5
C18—C17—H17	120	H30A—C30—H30B	109.5
C16—C17—H17	120	C27—C30—H30C	109.5
C17—C18—C19	119.90 (19)	H30A—C30—H30C	109.5
C17—C18—H18	120.1	H30B—C30—H30C	109.5
C19—C18—H18	120.1	C26—O2—H2	114 (2)
C5—C1—C2—C3	0.9 (3)	C17—C18—C19—C14	1.3 (3)
C6—C1—C2—C3	−177.50 (19)	C15—C14—C19—C18	0.3 (3)
C1—C2—C3—N2	−0.7 (3)	C7—C14—C19—C18	178.88 (17)
N2—C4—C5—C1	−1.3 (4)	O1—C6—N1—N3	−1.7 (3)
C2—C1—C5—C4	0.1 (3)	C1—C6—N1—N3	178.83 (14)
C6—C1—C5—C4	178.55 (19)	C2—C3—N2—C4	−0.5 (3)
C2—C1—C6—O1	155.4 (2)	C5—C4—N2—C3	1.5 (3)
C5—C1—C6—O1	−22.9 (3)	C14—C7—N3—N1	179.38 (15)
C2—C1—C6—N1	−25.0 (3)	C8—C7—N3—N1	−0.7 (3)
C5—C1—C6—N1	156.60 (18)	C6—N1—N3—C7	173.36 (17)
N3—C7—C8—C9	64.3 (3)	C25—C20—C21—C22	0.0 (4)
C14—C7—C8—C9	−115.82 (19)	C26—C20—C21—C22	−179.9 (2)
N3—C7—C8—C13	−119.7 (2)	C20—C21—C22—C23	−0.4 (4)
C14—C7—C8—C13	60.2 (2)	C21—C22—C23—C24	0.3 (4)
C13—C8—C9—C10	−1.8 (3)	C21—C22—C23—C27	176.9 (2)
C7—C8—C9—C10	174.24 (18)	C22—C23—C24—C25	0.3 (3)
C8—C9—C10—C11	1.2 (3)	C27—C23—C24—C25	−176.27 (19)
C9—C10—C11—C12	0.5 (3)	C21—C20—C25—C24	0.5 (3)
C10—C11—C12—C13	−1.6 (3)	C26—C20—C25—C24	−179.54 (19)
C11—C12—C13—C8	1.0 (3)	C23—C24—C25—C20	−0.7 (3)
C9—C8—C13—C12	0.7 (3)	C25—C20—C26—O3	−3.5 (3)
C7—C8—C13—C12	−175.41 (17)	C21—C20—C26—O3	176.5 (2)
N3—C7—C14—C15	23.5 (2)	C25—C20—C26—O2	175.60 (19)
C8—C7—C14—C15	−156.46 (17)	C21—C20—C26—O2	−4.4 (3)
N3—C7—C14—C19	−155.12 (17)	C22—C23—C27—C28	163.3 (2)
C8—C7—C14—C19	24.9 (2)	C24—C23—C27—C28	−20.3 (3)
C19—C14—C15—C16	−1.2 (3)	C22—C23—C27—C30	41.9 (3)
C7—C14—C15—C16	−179.79 (18)	C24—C23—C27—C30	−141.6 (2)
C14—C15—C16—C17	0.5 (3)	C22—C23—C27—C29	−76.1 (3)
C15—C16—C17—C18	1.1 (3)	C24—C23—C27—C29	100.3 (2)
C16—C17—C18—C19	−2.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.88 (3)	1.80 (3)	2.668 (2)	167 (3)
C3—H3···O3	0.95	2.58	3.214 (3)	125

4-tert-Butylbenzoic acid–N'-(4-hydroxy-4-methylpentan-2-ylidene)pyridine-4-carbohydrazide (1/1) (V)

Crystal data

C12H17N3O2·C11H14O2	F(000) = 888
Mr = 413.51	Dx = 1.179 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9874 reflections
a = 20.3803 (8) Å	θ = 3.0–28.3°
b = 6.9598 (3) Å	µ = 0.08 mm^−1
c = 17.2533 (7) Å	T = 173 K
β = 107.838 (1)°	Plate, colourless
V = 2329.61 (17) Å^3	0.37 × 0.3 × 0.2 mm
Z = 4

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	4687 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 28.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −25→26
Tmin = 0.9, Tmax = 0.95	k = −8→9
28123 measured reflections	l = −22→22
5623 independent reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0661P)^2 + 0.7248P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5623 reflections	Δρmax = 0.31 e Å^−3
289 parameters	Δρmin = −0.31 e Å^−3
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
C1	0.41111 (5)	0.08068 (17)	0.13094 (7)	0.0247 (2)
C2	0.40281 (6)	0.27161 (17)	0.14902 (7)	0.0279 (2)
H2A	0.441188	0.346491	0.178927	0.033*
C3	0.33740 (6)	0.35064 (18)	0.12253 (8)	0.0326 (3)
H3A	0.331913	0.481626	0.134751	0.039*
C4	0.28978 (6)	0.0672 (2)	0.06554 (8)	0.0347 (3)
H4	0.250192	−0.004821	0.036883	0.042*
C5	0.35293 (6)	−0.02436 (18)	0.08949 (7)	0.0293 (2)
H5	0.356535	−0.156661	0.077862	0.035*
C6	0.48014 (6)	−0.01681 (17)	0.15333 (7)	0.0278 (2)
C7	0.71753 (7)	0.0770 (2)	0.18895 (14)	0.0589 (5)
H7A	0.723366	−0.01635	0.233091	0.088*
H7B	0.745801	0.190698	0.209724	0.088*
H7C	0.732005	0.018881	0.145073	0.088*
C8	0.64289 (6)	0.13485 (19)	0.15664 (9)	0.0370 (3)
C9	0.62479 (6)	0.29097 (19)	0.09317 (8)	0.0349 (3)
H9A	0.582576	0.251316	0.049916	0.042*
H9B	0.662376	0.299247	0.068101	0.042*
C10	0.61267 (6)	0.49314 (18)	0.12187 (7)	0.0295 (3)
C11	0.60343 (8)	0.6342 (2)	0.05210 (9)	0.0465 (4)
H11A	0.566057	0.589961	0.004777	0.07*
H11B	0.646305	0.642285	0.037769	0.07*
H11C	0.591953	0.761227	0.06876	0.07*
C12	0.67055 (7)	0.5555 (2)	0.19626 (8)	0.0395 (3)
H12A	0.660559	0.683858	0.213103	0.059*
H12B	0.713999	0.558646	0.183029	0.059*
H12C	0.674513	0.464252	0.240729	0.059*
N1	0.53224 (5)	0.10170 (15)	0.15447 (7)	0.0311 (2)
N2	0.28181 (5)	0.25229 (17)	0.08079 (7)	0.0348 (2)
N3	0.60059 (5)	0.03810 (16)	0.18311 (8)	0.0374 (3)
O1	0.48528 (4)	−0.19087 (13)	0.16572 (6)	0.0390 (2)
O2	0.54963 (5)	0.48230 (14)	0.14236 (6)	0.0369 (2)
H1	0.5258 (8)	0.234 (3)	0.1463 (9)	0.038 (4)*
H2	0.5367 (9)	0.593 (3)	0.1514 (11)	0.052 (5)*
C13	0.10610 (6)	0.70020 (18)	−0.06055 (7)	0.0292 (3)
C14	0.04333 (7)	0.6166 (2)	−0.06605 (11)	0.0470 (4)
H14	0.04198	0.491674	−0.044423	0.056*
C15	−0.01769 (7)	0.7136 (2)	−0.10285 (11)	0.0505 (4)
H15	−0.060267	0.652967	−0.106338	0.061*
C16	−0.01823 (6)	0.89634 (19)	−0.13467 (8)	0.0330 (3)
C17	0.04530 (7)	0.9778 (2)	−0.12893 (9)	0.0395 (3)
H17	0.046847	1.102928	−0.150332	0.047*
C18	0.10653 (6)	0.8811 (2)	−0.09274 (8)	0.0374 (3)
H18	0.149178	0.940172	−0.09012	0.045*
C20	−0.08642 (7)	0.9977 (2)	−0.17768 (8)	0.0381 (3)
C19	0.17245 (6)	0.59863 (19)	−0.02078 (8)	0.0321 (3)
C21	−0.07695 (11)	1.2120 (3)	−0.1850 (2)	0.1041 (11)
H21A	−0.121614	1.271484	−0.212487	0.156*
H21B	−0.045233	1.23544	−0.216717	0.156*
H21C	−0.057875	1.267751	−0.130563	0.156*
C22	−0.13934 (9)	0.9629 (3)	−0.13345 (11)	0.0641 (5)
H22A	−0.120074	1.001775	−0.076367	0.096*
H22B	−0.151196	0.826106	−0.136181	0.096*
H22C	−0.180876	1.038445	−0.159282	0.096*
C23	−0.11496 (9)	0.9140 (4)	−0.26316 (10)	0.0713 (6)
H23A	−0.122222	0.77556	−0.259485	0.107*
H23B	−0.082075	0.936551	−0.293415	0.107*
H23C	−0.158912	0.976192	−0.291504	0.107*
O3	0.16422 (5)	0.43396 (16)	0.01190 (8)	0.0539 (3)
O4	0.22814 (5)	0.66225 (15)	−0.01899 (7)	0.0476 (3)
H3	0.2068 (11)	0.371 (3)	0.0365 (13)	0.075 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0211 (5)	0.0271 (5)	0.0264 (5)	0.0028 (4)	0.0080 (4)	0.0038 (4)
C2	0.0234 (5)	0.0288 (6)	0.0306 (5)	0.0002 (4)	0.0070 (4)	−0.0011 (5)
C3	0.0287 (6)	0.0282 (6)	0.0422 (7)	0.0052 (5)	0.0130 (5)	0.0026 (5)
C4	0.0224 (5)	0.0383 (7)	0.0406 (7)	−0.0030 (5)	0.0054 (5)	0.0017 (5)
C5	0.0275 (6)	0.0265 (6)	0.0347 (6)	−0.0013 (4)	0.0106 (5)	−0.0009 (5)
C6	0.0228 (5)	0.0265 (6)	0.0344 (6)	0.0027 (4)	0.0090 (4)	0.0022 (5)
C7	0.0234 (6)	0.0438 (9)	0.1089 (15)	0.0026 (6)	0.0195 (8)	0.0048 (9)
C8	0.0239 (6)	0.0299 (6)	0.0582 (8)	0.0006 (5)	0.0143 (5)	−0.0050 (6)
C9	0.0308 (6)	0.0375 (7)	0.0405 (7)	−0.0057 (5)	0.0170 (5)	−0.0088 (5)
C10	0.0292 (6)	0.0298 (6)	0.0312 (6)	−0.0027 (5)	0.0116 (5)	0.0010 (5)
C11	0.0534 (9)	0.0473 (8)	0.0370 (7)	−0.0094 (7)	0.0112 (6)	0.0093 (6)
C12	0.0388 (7)	0.0386 (7)	0.0375 (7)	−0.0019 (6)	0.0065 (5)	−0.0045 (6)
N1	0.0204 (5)	0.0259 (5)	0.0467 (6)	0.0043 (4)	0.0098 (4)	0.0057 (4)
N2	0.0224 (5)	0.0370 (6)	0.0438 (6)	0.0047 (4)	0.0083 (4)	0.0085 (5)
N3	0.0205 (5)	0.0302 (5)	0.0598 (7)	0.0042 (4)	0.0095 (5)	0.0042 (5)
O1	0.0282 (4)	0.0254 (4)	0.0637 (6)	0.0048 (3)	0.0145 (4)	0.0075 (4)
O2	0.0341 (5)	0.0249 (5)	0.0578 (6)	0.0020 (4)	0.0233 (4)	0.0020 (4)
C13	0.0237 (5)	0.0314 (6)	0.0310 (6)	0.0002 (5)	0.0062 (4)	0.0000 (5)
C14	0.0265 (6)	0.0356 (7)	0.0767 (10)	0.0010 (5)	0.0126 (6)	0.0180 (7)
C15	0.0226 (6)	0.0415 (8)	0.0838 (11)	−0.0008 (6)	0.0111 (7)	0.0179 (8)
C16	0.0278 (6)	0.0358 (7)	0.0337 (6)	0.0032 (5)	0.0067 (5)	0.0028 (5)
C17	0.0333 (6)	0.0372 (7)	0.0467 (7)	0.0010 (5)	0.0101 (6)	0.0140 (6)
C18	0.0258 (6)	0.0390 (7)	0.0453 (7)	−0.0045 (5)	0.0079 (5)	0.0077 (6)
C20	0.0289 (6)	0.0421 (7)	0.0416 (7)	0.0080 (5)	0.0084 (5)	0.0087 (6)
C19	0.0243 (5)	0.0330 (6)	0.0368 (6)	−0.0002 (5)	0.0059 (5)	−0.0004 (5)
C21	0.0460 (10)	0.0474 (11)	0.192 (3)	0.0132 (9)	−0.0036 (14)	0.0362 (15)
C22	0.0492 (9)	0.0944 (14)	0.0559 (9)	0.0356 (9)	0.0269 (8)	0.0263 (10)
C23	0.0506 (10)	0.1170 (18)	0.0398 (8)	0.0374 (11)	0.0043 (7)	0.0048 (10)
O3	0.0237 (4)	0.0468 (6)	0.0874 (8)	0.0065 (4)	0.0113 (5)	0.0301 (6)
O4	0.0230 (4)	0.0441 (6)	0.0717 (7)	−0.0026 (4)	0.0087 (4)	0.0090 (5)

Geometric parameters (Å, º)

C1—C2	1.3870 (16)	N1—N3	1.3996 (13)
C1—C5	1.3901 (16)	N1—H1	0.933 (17)
C1—C6	1.5020 (15)	O2—H2	0.84 (2)
C2—C3	1.3839 (16)	C13—C18	1.3772 (18)
C2—H2A	0.95	C13—C14	1.3820 (17)
C3—N2	1.3307 (16)	C13—C19	1.4935 (16)
C3—H3A	0.95	C14—C15	1.3860 (19)
C4—N2	1.3344 (18)	C14—H14	0.95
C4—C5	1.3813 (17)	C15—C16	1.384 (2)
C4—H4	0.95	C15—H15	0.95
C5—H5	0.95	C16—C17	1.3891 (18)
C6—O1	1.2290 (15)	C16—C20	1.5323 (17)
C6—N1	1.3400 (15)	C17—C18	1.3867 (18)
C7—C8	1.5058 (18)	C17—H17	0.95
C7—H7A	0.98	C18—H18	0.95
C7—H7B	0.98	C20—C21	1.514 (2)
C7—H7C	0.98	C20—C22	1.519 (2)
C8—N3	1.2831 (17)	C20—C23	1.526 (2)
C8—C9	1.506 (2)	C19—O4	1.2098 (15)
C9—C10	1.5366 (18)	C19—O3	1.3105 (17)
C9—H9A	0.99	C21—H21A	0.98
C9—H9B	0.99	C21—H21B	0.98
C10—O2	1.4352 (14)	C21—H21C	0.98
C10—C12	1.5165 (17)	C22—H22A	0.98
C10—C11	1.5195 (18)	C22—H22B	0.98
C11—H11A	0.98	C22—H22C	0.98
C11—H11B	0.98	C23—H23A	0.98
C11—H11C	0.98	C23—H23B	0.98
C12—H12A	0.98	C23—H23C	0.98
C12—H12B	0.98	O3—H3	0.95 (2)
C12—H12C	0.98
C2—C1—C5	118.42 (10)	C6—N1—H1	122.1 (9)
C2—C1—C6	122.97 (10)	N3—N1—H1	116.3 (9)
C5—C1—C6	118.61 (10)	C3—N2—C4	117.92 (10)
C3—C2—C1	118.56 (11)	C8—N3—N1	114.39 (11)
C3—C2—H2A	120.7	C10—O2—H2	110.6 (12)
C1—C2—H2A	120.7	C18—C13—C14	118.50 (11)
N2—C3—C2	123.27 (12)	C18—C13—C19	120.09 (11)
N2—C3—H3A	118.4	C14—C13—C19	121.41 (11)
C2—C3—H3A	118.4	C13—C14—C15	120.56 (13)
N2—C4—C5	123.03 (11)	C13—C14—H14	119.7
N2—C4—H4	118.5	C15—C14—H14	119.7
C5—C4—H4	118.5	C16—C15—C14	121.75 (12)
C4—C5—C1	118.75 (11)	C16—C15—H15	119.1
C4—C5—H5	120.6	C14—C15—H15	119.1
C1—C5—H5	120.6	C15—C16—C17	116.93 (12)
O1—C6—N1	125.39 (11)	C15—C16—C20	120.75 (12)
O1—C6—C1	120.89 (10)	C17—C16—C20	122.26 (12)
N1—C6—C1	113.66 (10)	C18—C17—C16	121.63 (12)
C8—C7—H7A	109.5	C18—C17—H17	119.2
C8—C7—H7B	109.5	C16—C17—H17	119.2
H7A—C7—H7B	109.5	C13—C18—C17	120.63 (12)
C8—C7—H7C	109.5	C13—C18—H18	119.7
H7A—C7—H7C	109.5	C17—C18—H18	119.7
H7B—C7—H7C	109.5	C21—C20—C22	109.10 (17)
N3—C8—C7	116.13 (13)	C21—C20—C23	108.43 (19)
N3—C8—C9	126.57 (11)	C22—C20—C23	107.79 (14)
C7—C8—C9	117.18 (12)	C21—C20—C16	111.98 (13)
C8—C9—C10	117.01 (11)	C22—C20—C16	111.18 (11)
C8—C9—H9A	108	C23—C20—C16	108.24 (12)
C10—C9—H9A	108	O4—C19—O3	123.49 (12)
C8—C9—H9B	108	O4—C19—C13	123.28 (12)
C10—C9—H9B	108	O3—C19—C13	113.22 (10)
H9A—C9—H9B	107.3	C20—C21—H21A	109.5
O2—C10—C12	109.24 (10)	C20—C21—H21B	109.5
O2—C10—C11	109.03 (11)	H21A—C21—H21B	109.5
C12—C10—C11	111.17 (11)	C20—C21—H21C	109.5
O2—C10—C9	106.00 (9)	H21A—C21—H21C	109.5
C12—C10—C9	112.00 (11)	H21B—C21—H21C	109.5
C11—C10—C9	109.23 (11)	C20—C22—H22A	109.5
C10—C11—H11A	109.5	C20—C22—H22B	109.5
C10—C11—H11B	109.5	H22A—C22—H22B	109.5
H11A—C11—H11B	109.5	C20—C22—H22C	109.5
C10—C11—H11C	109.5	H22A—C22—H22C	109.5
H11A—C11—H11C	109.5	H22B—C22—H22C	109.5
H11B—C11—H11C	109.5	C20—C23—H23A	109.5
C10—C12—H12A	109.5	C20—C23—H23B	109.5
C10—C12—H12B	109.5	H23A—C23—H23B	109.5
H12A—C12—H12B	109.5	C20—C23—H23C	109.5
C10—C12—H12C	109.5	H23A—C23—H23C	109.5
H12A—C12—H12C	109.5	H23B—C23—H23C	109.5
H12B—C12—H12C	109.5	C19—O3—H3	112.1 (13)
C6—N1—N3	120.60 (10)
C5—C1—C2—C3	−2.21 (17)	C6—N1—N3—C8	157.34 (12)
C6—C1—C2—C3	177.10 (11)	C18—C13—C14—C15	−0.3 (2)
C1—C2—C3—N2	0.32 (19)	C19—C13—C14—C15	179.70 (15)
N2—C4—C5—C1	−0.45 (19)	C13—C14—C15—C16	−0.5 (3)
C2—C1—C5—C4	2.27 (17)	C14—C15—C16—C17	0.7 (2)
C6—C1—C5—C4	−177.07 (11)	C14—C15—C16—C20	177.87 (15)
C2—C1—C6—O1	151.98 (12)	C15—C16—C17—C18	−0.2 (2)
C5—C1—C6—O1	−28.70 (17)	C20—C16—C17—C18	−177.33 (13)
C2—C1—C6—N1	−30.71 (16)	C14—C13—C18—C17	0.8 (2)
C5—C1—C6—N1	148.61 (11)	C19—C13—C18—C17	−179.21 (13)
N3—C8—C9—C10	82.25 (17)	C16—C17—C18—C13	−0.5 (2)
C7—C8—C9—C10	−101.81 (15)	C15—C16—C20—C21	162.8 (2)
C8—C9—C10—O2	−69.22 (13)	C17—C16—C20—C21	−20.2 (2)
C8—C9—C10—C12	49.84 (14)	C15—C16—C20—C22	40.5 (2)
C8—C9—C10—C11	173.45 (11)	C17—C16—C20—C22	−142.56 (16)
O1—C6—N1—N3	−10.2 (2)	C15—C16—C20—C23	−77.75 (19)
C1—C6—N1—N3	172.67 (11)	C17—C16—C20—C23	99.23 (18)
C2—C3—N2—C4	1.51 (19)	C18—C13—C19—O4	−4.5 (2)
C5—C4—N2—C3	−1.45 (19)	C14—C13—C19—O4	175.55 (15)
C7—C8—N3—N1	177.30 (13)	C18—C13—C19—O3	175.55 (13)
C9—C8—N3—N1	−6.7 (2)	C14—C13—C19—O3	−4.44 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.84 (2)	1.89 (2)	2.7166 (13)	165.2 (17)
N1—H1···O2	0.933 (17)	1.804 (17)	2.6891 (14)	157.5 (14)
O3—H3···N2	0.95 (2)	1.70 (2)	2.6476 (14)	178 (2)

Symmetry code: (i) x, y+1, z.