2-Amino-5-[4-(octylamino)phen­yl]cyclo­hepta-2,4,6-trien-1-one

Kubo, K.; Matsumoto, T.; Katahira, K.; Mori, A.

doi:10.1107/S1600536805023792

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2-Amino-5-[4-(octylamino)phenyl]cyclohepta-2,4,6-trien-1-one

K. Kubo, T. Matsumoto, K. Katahira and A. Mori

The title compound, also known as 2-amino-5-[4-(octylamino)phenyl]tropone, C₂₁H₂₈N₂O, contains two crystallographically independent molecules in the asymmetric unit. The NH₂ group of the 2-aminotropone unit and the NH group of the aminobenzene unit participate in intermolecular hydrogen bonding with the O atoms of neighbouring molecules. An intermolecular π–π interaction is observed in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023792/cf6449sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023792/cf6449Isup2.hkl Contains datablock I

CCDC reference: 282273

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.004 Å
R factor = 0.071
wR factor = 0.202
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.49
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.29
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H2     ...          ?

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

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

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; 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: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: CrystalStructure.

2-Amino-5-[4-(octylamino)phenyl]cyclohepta-2,4,6-trien-1-one top

Crystal data top

C₂₁H₂₈N₂O	Z = 4
M_r = 324.46	F(000) = 704.00
Triclinic, P1	D_x = 1.176 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.691 (2) Å	Cell parameters from 2903 reflections
b = 14.882 (4) Å	θ = 3.1–27.5°
c = 16.948 (5) Å	µ = 0.07 mm⁻¹
α = 77.200 (14)°	T = 123 K
β = 77.262 (14)°	Platelet, yellow
γ = 80.658 (14)°	0.12 × 0.10 × 0.03 mm
V = 1832.0 (9) Å³

Data collection top

Rigaku Saturn diffractometer	3759 reflections with I > 2σ(I)
Detector resolution: 7.31 pixels mm^-1	R_int = 0.064
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)	h = −9→9
T_min = 0.991, T_max = 0.998	k = −19→19
22067 measured reflections	l = −21→21
8302 independent reflections

Refinement top

Refinement on F²	w = 1/[0.0015F_o² + σ(F_o²)]/(4F_o²)
R[F² > 2σ(F²)] = 0.071	(Δ/σ)_max < 0.001
wR(F²) = 0.202	Δρ_max = 0.53 e Å⁻³
S = 1.00	Δρ_min = −0.49 e Å⁻³
8285 reflections	Extinction correction: Larson (1970), eq. 22
508 parameters	Extinction coefficient: 156 (60)
H atoms treated by a mixture of independent and constrained refinement

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.5904 (2)	−0.17499 (12)	0.92294 (13)	0.0420 (5)
O2	−0.7684 (2)	0.43864 (12)	0.87833 (14)	0.0497 (6)
N1	−0.8196 (2)	−0.03081 (19)	0.93900 (18)	0.0430 (7)
N2	0.2986 (2)	0.29675 (14)	0.77113 (17)	0.0412 (7)
N3	−0.5656 (3)	0.32250 (17)	0.9663 (2)	0.0439 (7)
N4	0.2345 (3)	0.83994 (16)	0.77863 (19)	0.0435 (7)
C1	−0.5203 (3)	−0.09927 (17)	0.90830 (19)	0.0355 (7)
C2	−0.6465 (3)	−0.01504 (18)	0.91794 (19)	0.0356 (7)
C3	−0.6016 (3)	0.07370 (17)	0.90716 (19)	0.0374 (7)
C4	−0.4381 (3)	0.10978 (17)	0.88252 (19)	0.0369 (7)
C5	−0.2648 (3)	0.06720 (17)	0.85957 (19)	0.0336 (7)
C6	−0.2234 (3)	−0.02941 (17)	0.8607 (2)	0.0371 (7)
C7	−0.3326 (3)	−0.09895 (17)	0.88204 (19)	0.0369 (7)
C8	−0.1156 (3)	0.12548 (16)	0.83487 (19)	0.0342 (7)
C9	−0.1198 (3)	0.20149 (17)	0.8727 (2)	0.0368 (7)
C10	0.0160 (3)	0.25720 (17)	0.8509 (2)	0.0375 (7)
C11	0.1656 (3)	0.24104 (17)	0.78853 (19)	0.0359 (7)
C12	0.1713 (3)	0.16649 (17)	0.74969 (19)	0.0372 (7)
C13	0.0338 (3)	0.11064 (17)	0.77316 (19)	0.0372 (7)
C14	0.4667 (3)	0.28704 (17)	0.7130 (2)	0.0414 (8)
C15	0.5838 (3)	0.35556 (18)	0.7225 (2)	0.0407 (8)
C16	0.7680 (3)	0.35629 (18)	0.6666 (2)	0.0420 (8)
C17	0.8603 (3)	0.43722 (18)	0.6725 (2)	0.0466 (8)
C18	1.0458 (3)	0.44315 (19)	0.6208 (2)	0.0456 (8)
C19	1.1335 (3)	0.52461 (19)	0.6299 (2)	0.0551 (9)
C20	1.3160 (3)	0.5337 (2)	0.5746 (2)	0.0580 (10)
C21	1.4047 (4)	0.6141 (2)	0.5834 (2)	0.0765 (13)
C22	−0.6227 (3)	0.46744 (18)	0.8805 (2)	0.0412 (8)
C23	−0.5026 (3)	0.40458 (18)	0.9309 (2)	0.0405 (8)
C24	−0.3362 (3)	0.42076 (18)	0.9403 (2)	0.0398 (8)
C25	−0.2389 (3)	0.49549 (17)	0.9095 (2)	0.0398 (8)
C26	−0.2790 (3)	0.58025 (18)	0.8581 (2)	0.0405 (8)
C27	−0.4383 (3)	0.60486 (18)	0.8269 (2)	0.0437 (8)
C28	−0.5826 (3)	0.55685 (17)	0.8357 (2)	0.0414 (8)
C29	−0.1476 (3)	0.64890 (18)	0.8373 (2)	0.0373 (8)
C30	−0.0504 (3)	0.65994 (17)	0.8950 (2)	0.0385 (8)
C31	0.0725 (3)	0.72352 (17)	0.8753 (2)	0.0376 (8)
C32	0.1094 (3)	0.77758 (18)	0.7957 (2)	0.0387 (8)
C33	0.0146 (3)	0.76721 (18)	0.7378 (2)	0.0431 (8)
C34	−0.1108 (3)	0.70448 (18)	0.7583 (2)	0.0411 (8)
C35	0.3114 (3)	0.88325 (19)	0.6964 (2)	0.0440 (8)
C36	0.4656 (3)	0.93323 (19)	0.6991 (2)	0.0449 (8)
C37	0.5510 (3)	0.9897 (2)	0.6175 (2)	0.0478 (9)
C38	0.7103 (3)	1.03365 (19)	0.6257 (2)	0.0465 (9)
C39	0.8001 (4)	1.0925 (2)	0.5465 (2)	0.0490 (9)
C40	0.9623 (4)	1.1326 (2)	0.5568 (2)	0.0480 (9)
C41	1.0564 (4)	1.1906 (2)	0.4788 (2)	0.0546 (10)
C42	1.2145 (4)	1.2326 (2)	0.4903 (2)	0.0646 (11)
H1	−0.840 (3)	−0.088 (2)	0.939 (2)	0.056 (9)*
H2	−0.901 (4)	0.013 (2)	0.937 (2)	0.053 (9)*
H3	−0.7016	0.1186	0.9191	0.046*
H4	−0.4461	0.1745	0.8810	0.046*
H5	−0.0997	−0.0494	0.8437	0.046*
H6	−0.2693	−0.1587	0.8785	0.046*
H7	−0.2196	0.2146	0.9146	0.045*
H8	0.0091	0.3072	0.8783	0.046*
H9	0.2699	0.1542	0.7071	0.044*
H10	0.0415	0.0601	0.7462	0.046*
H11	0.277 (3)	0.3474 (19)	0.7977 (17)	0.036 (7)*
H12	0.5250	0.2255	0.7244	0.048*
H13	0.4445	0.3005	0.6583	0.048*
H14	0.5209	0.4161	0.7117	0.047*
H15	0.6010	0.3412	0.7779	0.047*
H16	0.8401	0.2998	0.6826	0.048*
H17	0.7546	0.3619	0.6113	0.048*
H18	0.7873	0.4931	0.6557	0.052*
H19	0.8689	0.4317	0.7285	0.052*
H20	1.1195	0.3873	0.6370	0.050*
H21	1.0381	0.4498	0.5646	0.051*
H22	1.0569	0.5802	0.6163	0.061*
H23	1.1466	0.5164	0.6855	0.061*
H24	1.3923	0.4779	0.5880	0.063*
H25	1.3027	0.5422	0.5189	0.063*
H26	1.3713	0.6680	0.5454	0.086*
H27	1.5315	0.5992	0.5725	0.086*
H28	1.3664	0.6254	0.6380	0.086*
H29	−0.672 (4)	0.320 (2)	0.9586 (19)	0.047 (8)*
H30	−0.524 (4)	0.279 (2)	1.011 (2)	0.087 (13)*
H31	−0.2785	0.3710	0.9748	0.050*
H32	−0.1259	0.4878	0.9257	0.050*
H33	−0.4484	0.6652	0.7936	0.055*
H34	−0.6722	0.5897	0.8060	0.053*
H35	−0.0695	0.6227	0.9487	0.046*
H36	0.1326	0.7309	0.9164	0.046*
H37	0.0363	0.8034	0.6836	0.053*
H38	−0.1742	0.6991	0.7177	0.051*
H39	0.298 (3)	0.828 (2)	0.825 (2)	0.051 (9)*
H40	0.3541	0.8372	0.6635	0.052*
H41	0.2225	0.9266	0.6731	0.053*
H42	0.4223	0.9742	0.7367	0.053*
H43	0.5563	0.8880	0.7188	0.053*
H44	0.5911	0.9500	0.5786	0.056*
H45	0.4634	1.0375	0.5985	0.056*
H46	0.6693	1.0720	0.6657	0.055*
H47	0.7975	0.9853	0.6442	0.055*
H48	0.8383	1.0550	0.5058	0.056*
H49	0.7147	1.1424	0.5288	0.056*
H50	0.9231	1.1705	0.5971	0.055*
H51	1.0462	1.0824	0.5755	0.055*
H52	0.9718	1.2396	0.4591	0.062*
H53	1.0994	1.1522	0.4390	0.062*
H54	1.1737	1.2918	0.5042	0.075*
H55	1.3013	1.2390	0.4405	0.075*
H56	1.2672	1.1932	0.5333	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0319 (9)	0.0266 (9)	0.0725 (16)	−0.0055 (7)	−0.0150 (9)	−0.0135 (9)
O2	0.0333 (10)	0.0327 (10)	0.0931 (19)	0.0005 (8)	−0.0223 (10)	−0.0261 (11)
N1	0.0256 (11)	0.0311 (13)	0.076 (2)	0.0023 (10)	−0.0178 (12)	−0.0148 (13)
N2	0.0327 (11)	0.0269 (11)	0.0639 (19)	−0.0063 (9)	0.0007 (11)	−0.0163 (12)
N3	0.0339 (13)	0.0283 (12)	0.073 (2)	−0.0019 (10)	−0.0117 (13)	−0.0167 (13)
N4	0.0460 (13)	0.0317 (12)	0.0553 (19)	−0.0118 (11)	−0.0113 (13)	−0.0070 (12)
C1	0.0307 (13)	0.0249 (12)	0.055 (2)	−0.0034 (10)	−0.0140 (12)	−0.0116 (12)
C2	0.0257 (12)	0.0306 (13)	0.056 (2)	0.0007 (10)	−0.0171 (12)	−0.0125 (13)
C3	0.0291 (13)	0.0269 (12)	0.059 (2)	0.0048 (10)	−0.0142 (13)	−0.0141 (13)
C4	0.0335 (13)	0.0227 (12)	0.058 (2)	0.0016 (10)	−0.0152 (13)	−0.0136 (12)
C5	0.0308 (12)	0.0233 (12)	0.0514 (19)	−0.0025 (10)	−0.0145 (12)	−0.0110 (12)
C6	0.0294 (12)	0.0248 (12)	0.060 (2)	0.0019 (10)	−0.0110 (13)	−0.0151 (13)
C7	0.0295 (12)	0.0223 (12)	0.062 (2)	0.0036 (10)	−0.0150 (13)	−0.0139 (13)
C8	0.0293 (12)	0.0215 (11)	0.053 (2)	0.0004 (10)	−0.0101 (12)	−0.0103 (12)
C9	0.0305 (13)	0.0249 (12)	0.057 (2)	0.0007 (10)	−0.0090 (13)	−0.0141 (12)
C10	0.0314 (13)	0.0216 (12)	0.062 (2)	0.0015 (10)	−0.0107 (13)	−0.0149 (12)
C11	0.0301 (13)	0.0222 (12)	0.054 (2)	−0.0008 (10)	−0.0061 (12)	−0.0070 (12)
C12	0.0327 (13)	0.0247 (12)	0.053 (2)	−0.0009 (11)	−0.0040 (13)	−0.0108 (12)
C13	0.0362 (14)	0.0244 (12)	0.054 (2)	0.0022 (11)	−0.0123 (13)	−0.0143 (13)
C14	0.0338 (13)	0.0230 (12)	0.062 (2)	−0.0020 (11)	−0.0015 (13)	−0.0064 (13)
C15	0.0372 (14)	0.0248 (12)	0.057 (2)	−0.0046 (11)	−0.0018 (13)	−0.0072 (13)
C16	0.0357 (14)	0.0268 (13)	0.057 (2)	−0.0014 (11)	−0.0020 (13)	−0.0037 (13)
C17	0.0361 (14)	0.0277 (13)	0.066 (2)	−0.0032 (11)	0.0048 (14)	−0.0038 (14)
C18	0.0345 (14)	0.0315 (14)	0.060 (2)	−0.0020 (12)	0.0025 (14)	0.0003 (14)
C19	0.0378 (15)	0.0283 (14)	0.086 (2)	−0.0039 (12)	0.0080 (16)	−0.0038 (15)
C20	0.0431 (16)	0.0382 (16)	0.076 (2)	−0.0059 (14)	0.0052 (16)	0.0085 (16)
C21	0.0492 (19)	0.0473 (19)	0.117 (3)	−0.0138 (16)	0.007 (2)	0.000 (2)
C22	0.0295 (13)	0.0277 (13)	0.072 (2)	0.0054 (11)	−0.0144 (14)	−0.0240 (14)
C23	0.0343 (13)	0.0243 (12)	0.067 (2)	0.0027 (11)	−0.0107 (14)	−0.0212 (13)
C24	0.0316 (13)	0.0249 (13)	0.068 (2)	0.0038 (11)	−0.0176 (13)	−0.0158 (13)
C25	0.0278 (12)	0.0265 (13)	0.070 (2)	0.0039 (10)	−0.0152 (13)	−0.0195 (13)
C26	0.0322 (13)	0.0257 (12)	0.070 (2)	0.0017 (11)	−0.0138 (13)	−0.0214 (13)
C27	0.0384 (14)	0.0259 (13)	0.073 (2)	0.0053 (11)	−0.0200 (15)	−0.0193 (14)
C28	0.0357 (14)	0.0251 (13)	0.070 (2)	0.0052 (11)	−0.0221 (14)	−0.0180 (14)
C29	0.0308 (13)	0.0261 (13)	0.059 (2)	0.0041 (11)	−0.0136 (13)	−0.0164 (13)
C30	0.0274 (12)	0.0261 (13)	0.062 (2)	0.0042 (10)	−0.0109 (13)	−0.0117 (13)
C31	0.0286 (12)	0.0275 (13)	0.060 (2)	0.0010 (10)	−0.0153 (13)	−0.0121 (13)
C32	0.0346 (13)	0.0238 (12)	0.061 (2)	0.0008 (11)	−0.0126 (13)	−0.0140 (13)
C33	0.0446 (15)	0.0287 (13)	0.058 (2)	−0.0024 (12)	−0.0117 (15)	−0.0122 (14)
C34	0.0393 (14)	0.0296 (13)	0.060 (2)	0.0007 (11)	−0.0180 (14)	−0.0147 (14)
C35	0.0452 (15)	0.0315 (14)	0.055 (2)	−0.0016 (12)	−0.0086 (15)	−0.0101 (14)
C36	0.0445 (16)	0.0283 (13)	0.060 (2)	−0.0028 (12)	−0.0052 (15)	−0.0091 (14)
C37	0.0492 (17)	0.0346 (15)	0.056 (2)	−0.0041 (13)	−0.0043 (15)	−0.0085 (14)
C38	0.0510 (17)	0.0306 (14)	0.055 (2)	−0.0066 (13)	−0.0018 (15)	−0.0086 (14)
C39	0.0536 (18)	0.0359 (15)	0.051 (2)	−0.0044 (14)	−0.0007 (15)	−0.0045 (14)
C40	0.0541 (17)	0.0315 (14)	0.053 (2)	−0.0082 (13)	0.0034 (15)	−0.0074 (14)
C41	0.0597 (19)	0.0410 (17)	0.055 (2)	−0.0035 (15)	−0.0020 (17)	−0.0040 (15)
C42	0.064 (2)	0.0512 (19)	0.071 (2)	−0.0105 (17)	0.0027 (19)	−0.0083 (19)

Geometric parameters (Å, º) top

O1—C1	1.279 (3)	N3—H29	0.87 (3)
O2—C22	1.274 (3)	N3—H30	0.97 (3)
N1—C2	1.345 (3)	N4—H39	0.98 (3)
N2—C11	1.362 (3)	C3—H3	0.950
N2—C14	1.451 (3)	C4—H4	0.950
N3—C23	1.352 (3)	C6—H5	0.950
N4—C32	1.385 (3)	C7—H6	0.950
N4—C35	1.439 (4)	C9—H7	0.950
C1—C2	1.472 (3)	C10—H8	0.950
C1—C7	1.414 (3)	C12—H9	0.950
C2—C3	1.382 (3)	C13—H10	0.950
C3—C4	1.390 (3)	C14—H12	0.950
C4—C5	1.391 (3)	C14—H13	0.950
C5—C6	1.418 (3)	C15—H14	0.950
C5—C8	1.482 (3)	C15—H15	0.950
C6—C7	1.375 (3)	C16—H16	0.950
C8—C9	1.411 (4)	C16—H17	0.950
C8—C13	1.397 (3)	C17—H18	0.950
C9—C10	1.374 (3)	C17—H19	0.950
C10—C11	1.409 (3)	C18—H20	0.950
C11—C12	1.400 (4)	C18—H21	0.950
C12—C13	1.386 (3)	C19—H22	0.950
C14—C15	1.521 (4)	C19—H23	0.950
C15—C16	1.521 (3)	C20—H24	0.950
C16—C17	1.525 (4)	C20—H25	0.950
C17—C18	1.506 (3)	C21—H26	0.950
C18—C19	1.530 (4)	C21—H27	0.950
C19—C20	1.513 (4)	C21—H28	0.950
C20—C21	1.519 (5)	C24—H31	0.950
C22—C23	1.473 (4)	C25—H32	0.950
C22—C28	1.423 (3)	C27—H33	0.950
C23—C24	1.389 (4)	C28—H34	0.950
C24—C25	1.382 (3)	C30—H35	0.950
C25—C26	1.397 (3)	C31—H36	0.950
C26—C27	1.404 (4)	C33—H37	0.950
C26—C29	1.486 (3)	C34—H38	0.950
C27—C28	1.379 (4)	C35—H40	0.950
C29—C30	1.405 (4)	C35—H41	0.950
C29—C34	1.405 (4)	C36—H42	0.950
C30—C31	1.382 (3)	C36—H43	0.950
C31—C32	1.406 (4)	C37—H44	0.950
C32—C33	1.392 (5)	C37—H45	0.950
C33—C34	1.387 (4)	C38—H46	0.950
C35—C36	1.512 (4)	C38—H47	0.950
C36—C37	1.521 (4)	C39—H48	0.950
C37—C38	1.524 (4)	C39—H49	0.950
C38—C39	1.521 (4)	C40—H50	0.950
C39—C40	1.525 (4)	C40—H51	0.950
C40—C41	1.514 (4)	C41—H52	0.950
C41—C42	1.520 (5)	C41—H53	0.950
N1—H1	0.89 (3)	C42—H54	0.950
N1—H2	0.83 (3)	C42—H55	0.950
N2—H11	0.93 (3)	C42—H56	0.950

O1···N3ⁱ	2.845 (3)	C10···H19ⁱⁱⁱ	3.166
O1···N4ⁱⁱ	2.993 (4)	C10···H31	3.262
O1···C31ⁱⁱ	3.520 (3)	C11···H3^v	2.805
O2···N2ⁱⁱⁱ	2.993 (3)	C11···H4^v	3.574
O2···C10ⁱⁱⁱ	3.550 (3)	C11···H16ⁱⁱⁱ	3.291
O2···C25ⁱⁱⁱ	3.529 (3)	C11···H19ⁱⁱⁱ	3.455
N1···N1^iv	3.210 (3)	C11···H20ⁱⁱⁱ	3.022
N1···N4ⁱⁱ	3.580 (4)	C12···H2^v	3.46 (3)
N1···C5ⁱ	3.523 (4)	C12···H3^v	3.132
N1···C8ⁱⁱⁱ	3.455 (3)	C12···H16ⁱⁱⁱ	3.218
N1···C13ⁱⁱⁱ	3.407 (3)	C12···H20ⁱⁱⁱ	3.425
N2···O2^v	2.993 (3)	C12···H42^ix	3.204
N2···C4^v	3.597 (3)	C12···H50ⁱⁱ	3.522
N3···O1ⁱ	2.845 (3)	C12···H56ⁱⁱ	3.523
N3···C1ⁱ	3.573 (3)	C13···H2^v	2.94 (3)
N3···C26^vi	3.486 (4)	C13···H3^v	3.564
N3···C30^vi	3.358 (3)	C13···H16ⁱⁱⁱ	3.198
N4···O1^vii	2.993 (4)	C13···H41^ix	3.488
N4···N1^vii	3.580 (4)	C13···H42^ix	3.348
N4···C1^vii	3.531 (4)	C13···H50ⁱⁱ	3.180
C1···N3ⁱ	3.573 (3)	C13···H51ⁱⁱ	3.446
C1···N4ⁱⁱ	3.531 (4)	C14···H4^v	3.119
C1···C3ⁱ	3.570 (4)	C14···H20ⁱⁱⁱ	3.223
C1···C4ⁱ	3.459 (4)	C14···H24ⁱⁱⁱ	3.197
C1···C36ⁱⁱ	3.495 (4)	C14···H46^ix	3.504
C2···C4ⁱ	3.522 (4)	C15···H4^v	3.354
C3···C1ⁱ	3.570 (4)	C15···H24ⁱⁱⁱ	3.074
C3···C7ⁱ	3.591 (4)	C16···H24ⁱⁱⁱ	3.512
C3···C11ⁱⁱⁱ	3.372 (3)	C16···H25^xii	3.294
C3···C12ⁱⁱⁱ	3.423 (4)	C16···H50^ix	3.194
C4···N2ⁱⁱⁱ	3.597 (3)	C18···H13^v	3.531
C4···C1ⁱ	3.459 (4)	C18···H21^xii	3.342
C4···C2ⁱ	3.522 (4)	C18···H54^ix	3.215
C4···C14ⁱⁱⁱ	3.563 (3)	C19···H14^v	3.561
C5···N1ⁱ	3.523 (4)	C19···H38^v	3.567
C7···C3ⁱ	3.591 (4)	C19···H52^xiii	3.537
C8···N1^v	3.455 (3)	C20···H13^v	3.516
C10···O2^v	3.550 (3)	C20···H14^v	3.142
C11···C3^v	3.372 (3)	C20···H17^xii	3.308
C12···C3^v	3.423 (4)	C20···H24^viii	3.166
C13···N1^v	3.407 (3)	C20···H25^viii	3.172
C14···C4^v	3.563 (3)	C20···H27^viii	3.413
C15···C22^v	3.422 (4)	C21···H14^v	3.372
C20···C20^viii	3.530 (4)	C21···H18^v	3.506
C22···C15ⁱⁱⁱ	3.422 (4)	C21···H24^viii	3.439
C23···C25^vi	3.454 (4)	C21···H25^viii	3.442
C25···O2^v	3.529 (3)	C21···H52^xiii	3.439
C25···C23^vi	3.454 (4)	C21···H55^xiv	3.297
C26···N3^vi	3.486 (4)	C22···H11ⁱⁱⁱ	2.79 (3)
C28···C31ⁱⁱⁱ	3.385 (3)	C22···H14ⁱⁱⁱ	3.047
C30···N3^vi	3.358 (3)	C22···H15ⁱⁱⁱ	2.931
C31···O1^vii	3.520 (3)	C22···H32^vi	3.567
C31···C28^v	3.385 (3)	C22···H35^vi	3.475
C36···C1^vii	3.495 (4)	C22···H35^vi	3.475
O1···H4ⁱ	3.398	C23···H7	3.301
O1···H7ⁱ	2.803	C23···H11ⁱⁱⁱ	3.42 (3)
O1···H29ⁱ	3.35 (3)	C23···H15ⁱⁱⁱ	2.859
O1···H30ⁱ	1.90 (3)	C23···H35^vi	3.503
O1···H31ⁱ	3.236	C24···H7	3.153
O1···H33^ix	3.473	C24···H8	3.018
O1···H36ⁱⁱ	2.766	C24···H15ⁱⁱⁱ	3.380
O1···H39ⁱⁱ	2.02 (3)	C24···H19ⁱⁱⁱ	3.568
O1···H42ⁱⁱ	3.425	C24···H36^xv	3.397
O1···H43ⁱⁱ	3.363	C25···H8	3.200
O2···H8ⁱⁱⁱ	2.800	C25···H19ⁱⁱⁱ	3.304
O2···H11ⁱⁱⁱ	2.07 (3)	C26···H19ⁱⁱⁱ	3.352
O2···H14ⁱⁱⁱ	3.232	C26···H30^vi	3.34 (4)
O2···H15ⁱⁱⁱ	3.270	C27···H30^vi	3.50 (4)
O2···H23^x	3.386	C27···H39ⁱⁱⁱ	3.59 (2)
O2···H32ⁱⁱⁱ	2.716	C28···H14ⁱⁱⁱ	3.179
O2···H35ⁱⁱⁱ	3.530	C28···H15ⁱⁱⁱ	3.544
O2···H35^vi	2.925	C28···H28^x	3.370
N1···H1^iv	3.46 (3)	C28···H31^vi	3.500
N1···H2^iv	2.68 (2)	C28···H36ⁱⁱⁱ	3.433
N1···H5ⁱⁱⁱ	3.041	C29···H6^xi	3.048
N1···H7ⁱ	3.284	C29···H29^vi	3.53 (3)
N1···H10ⁱⁱⁱ	3.572	C29···H30^vi	3.41 (3)
N1···H39ⁱⁱ	3.07 (3)	C29···H34^v	3.568
N1···H42ⁱⁱ	3.513	C30···H6^xi	2.931
N2···H3^v	3.221	C30···H29^vi	2.93 (2)
N2···H4^v	3.095	C30···H30^vi	3.39 (3)
N2···H20ⁱⁱⁱ	2.882	C30···H34^v	3.099
N2···H23ⁱⁱⁱ	3.400	C31···H1^vii	3.42 (3)
N2···H29^v	3.33 (3)	C31···H5^xi	3.394
N3···H4	2.821	C31···H6^xi	2.910
N3···H6ⁱ	3.340	C31···H31^xv	3.226
N3···H7	2.940	C31···H34^v	2.821
N3···H11ⁱⁱⁱ	3.27 (3)	C32···H1^vii	3.58 (3)
N3···H15ⁱⁱⁱ	3.136	C32···H5^xi	2.981
N3···H35^vi	2.934	C32···H6^xi	3.040
N4···H1^vii	3.04 (3)	C32···H33^v	3.535
N4···H5^xi	2.952	C32···H34^v	3.010
N4···H10^xi	3.350	C33···H5^xi	3.485
N4···H33^v	3.271	C33···H6^xi	3.124
C1···H4ⁱ	3.463	C33···H28ⁱⁱⁱ	3.513
C1···H7ⁱ	3.485	C33···H34^v	3.453
C1···H30ⁱ	2.72 (3)	C33···H52^xvi	3.338
C1···H39ⁱⁱ	2.68 (3)	C33···H53^xvi	3.226
C1···H42ⁱⁱ	2.974	C34···H6^xi	3.117
C1···H43ⁱⁱ	3.178	C34···H22ⁱⁱⁱ	3.272
C2···H39ⁱⁱ	3.22 (3)	C34···H23ⁱⁱⁱ	3.454
C2···H42ⁱⁱ	3.035	C34···H43ⁱⁱⁱ	3.484
C3···H12ⁱⁱⁱ	3.455	C34···H52^xvi	3.550
C3···H42ⁱⁱ	3.485	C34···H53^xvi	3.537
C4···H12ⁱⁱⁱ	2.892	C35···H10^xi	3.223
C4···H15ⁱⁱⁱ	3.534	C36···H9^xi	3.405
C4···H30	3.57 (4)	C36···H10^xi	3.516
C5···H2^v	3.26 (3)	C37···H9^xi	3.384
C5···H12ⁱⁱⁱ	3.380	C37···H53^xiii	3.244
C5···H46ⁱⁱ	3.418	C38···H12^xi	3.567
C6···H1^v	3.40 (3)	C38···H53^xiii	3.211
C6···H2^v	3.24 (3)	C39···H48^xiii	3.337
C6···H46ⁱⁱ	3.532	C39···H51^xiii	3.572
C6···H47ⁱⁱ	3.596	C39···H53^xiii	3.562
C7···H3ⁱ	3.383	C40···H10^vii	3.310
C7···H30ⁱ	3.09 (3)	C40···H16^xi	3.511
C7···H39ⁱⁱ	3.59 (3)	C40···H48^xiii	3.236
C7···H42ⁱⁱ	3.316	C41···H22^xiii	3.494
C7···H43ⁱⁱ	3.124	C41···H37^xvi	2.972
C8···H2^v	2.76 (3)	C41···H38^xvi	3.368
C8···H16ⁱⁱⁱ	3.261	C41···H44^xiii	3.251
C9···H1ⁱ	3.24 (3)	C41···H47^xiii	3.590
C9···H2^v	3.13 (3)	C41···H48^xiii	3.576
C9···H3^v	3.447	C42···H22^xiii	3.595
C9···H15ⁱⁱⁱ	3.179	C42···H27^xiv	3.271
C9···H16ⁱⁱⁱ	3.289	C42···H38^xvi	3.514
C9···H31	3.294	C42···H44^xiii	3.208
C10···H3^v	2.984	C42···H45^v	3.583
C10···H16ⁱⁱⁱ	3.316

C11—N2—C14	126.2 (2)	C14—C15—H14	107.9
C32—N4—C35	123.4 (3)	C14—C15—H15	107.7
O1—C1—C2	116.0 (2)	C16—C15—H14	107.8
O1—C1—C7	120.4 (2)	C16—C15—H15	107.7
C2—C1—C7	123.6 (2)	H14—C15—H15	109.5
N1—C2—C1	113.5 (2)	C15—C16—H16	109.1
N1—C2—C3	120.3 (2)	C15—C16—H17	109.0
C1—C2—C3	126.2 (2)	C17—C16—H16	109.0
C2—C3—C4	132.3 (2)	C17—C16—H17	109.2
C3—C4—C5	130.9 (2)	H16—C16—H17	109.5
C4—C5—C6	123.3 (2)	C16—C17—H18	107.9
C4—C5—C8	118.2 (2)	C16—C17—H19	108.1
C6—C5—C8	118.4 (2)	C18—C17—H18	108.0
C5—C6—C7	130.7 (2)	C18—C17—H19	108.0
C1—C7—C6	132.8 (2)	H18—C17—H19	109.5
C5—C8—C9	120.6 (2)	C17—C18—H20	108.5
C5—C8—C13	123.2 (2)	C17—C18—H21	108.6
C9—C8—C13	116.2 (2)	C19—C18—H20	108.4
C8—C9—C10	122.1 (2)	C19—C18—H21	108.6
C9—C10—C11	120.9 (2)	H20—C18—H21	109.5
N2—C11—C10	118.4 (2)	C18—C19—H22	108.4
N2—C11—C12	123.7 (2)	C18—C19—H23	108.6
C10—C11—C12	117.9 (2)	C20—C19—H22	108.3
C11—C12—C13	120.3 (2)	C20—C19—H23	108.6
C8—C13—C12	122.7 (2)	H22—C19—H23	109.5
N2—C14—C15	107.8 (2)	C19—C20—H24	108.2
C14—C15—C16	116.1 (2)	C19—C20—H25	108.6
C15—C16—C17	111.0 (2)	C21—C20—H24	108.2
C16—C17—C18	115.3 (2)	C21—C20—H25	108.5
C17—C18—C19	113.3 (2)	H24—C20—H25	109.5
C18—C19—C20	113.4 (2)	C20—C21—H26	109.3
C19—C20—C21	113.8 (3)	C20—C21—H27	109.7
O2—C22—C23	117.0 (2)	C20—C21—H28	109.4
O2—C22—C28	120.0 (2)	H26—C21—H27	109.5
C23—C22—C28	123.0 (2)	H26—C21—H28	109.5
N3—C23—C22	112.9 (2)	H27—C21—H28	109.5
N3—C23—C24	120.4 (2)	C23—C24—H31	113.8
C22—C23—C24	126.7 (2)	C25—C24—H31	113.9
C23—C24—C25	132.3 (2)	C24—C25—H32	114.7
C24—C25—C26	130.6 (2)	C26—C25—H32	114.7
C25—C26—C27	123.6 (2)	C26—C27—H33	114.3
C25—C26—C29	118.0 (2)	C28—C27—H33	114.3
C27—C26—C29	118.4 (2)	C22—C28—H34	113.8
C26—C27—C28	131.4 (2)	C27—C28—H34	113.8
C22—C28—C27	132.4 (2)	C29—C30—H35	119.1
C26—C29—C30	121.7 (2)	C31—C30—H35	119.2
C26—C29—C34	121.7 (3)	C30—C31—H36	119.5
C30—C29—C34	116.6 (2)	C32—C31—H36	119.5
C29—C30—C31	121.6 (2)	C32—C33—H37	119.7
C30—C31—C32	121.0 (3)	C34—C33—H37	119.7
N4—C32—C31	119.0 (3)	C29—C34—H38	118.9
N4—C32—C33	123.0 (2)	C33—C34—H38	119.0
C31—C32—C33	118.0 (2)	N4—C35—H40	109.5
C32—C33—C34	120.7 (2)	N4—C35—H41	109.4
C29—C34—C33	122.1 (3)	C36—C35—H40	109.5
N4—C35—C36	109.6 (2)	C36—C35—H41	109.4
C35—C36—C37	116.0 (3)	H40—C35—H41	109.5
C36—C37—C38	112.1 (2)	C35—C36—H42	107.8
C37—C38—C39	114.8 (3)	C35—C36—H43	107.8
C38—C39—C40	113.0 (2)	C37—C36—H42	107.9
C39—C40—C41	114.4 (3)	C37—C36—H43	107.8
C40—C41—C42	114.1 (3)	H42—C36—H43	109.5
C2—N1—H1	115.8 (18)	C36—C37—H44	108.8
C2—N1—H2	120 (2)	C36—C37—H45	108.8
H1—N1—H2	121 (3)	C38—C37—H44	108.8
C11—N2—H11	116.4 (15)	C38—C37—H45	108.8
C14—N2—H11	117.4 (15)	H44—C37—H45	109.5
C23—N3—H29	113.2 (18)	C37—C38—H46	108.1
C23—N3—H30	125 (2)	C37—C38—H47	108.1
H29—N3—H30	118 (2)	C39—C38—H46	108.1
C32—N4—H39	108.6 (17)	C39—C38—H47	108.1
C35—N4—H39	122.6 (16)	H46—C38—H47	109.5
C2—C3—H3	113.8	C38—C39—H48	108.6
C4—C3—H3	113.9	C38—C39—H49	108.6
C3—C4—H4	114.5	C40—C39—H48	108.6
C5—C4—H4	114.6	C40—C39—H49	108.6
C5—C6—H5	114.7	H48—C39—H49	109.5
C7—C6—H5	114.6	C39—C40—H50	108.2
C1—C7—H6	113.6	C39—C40—H51	108.2
C6—C7—H6	113.6	C41—C40—H50	108.2
C8—C9—H7	119.0	C41—C40—H51	108.3
C10—C9—H7	118.9	H50—C40—H51	109.5
C9—C10—H8	119.6	C40—C41—H52	108.4
C11—C10—H8	119.5	C40—C41—H53	108.3
C11—C12—H9	119.8	C42—C41—H52	108.4
C13—C12—H9	119.9	C42—C41—H53	108.2
C8—C13—H10	118.7	H52—C41—H53	109.5
C12—C13—H10	118.6	C41—C42—H54	109.4
N2—C14—H12	109.9	C41—C42—H55	109.6
N2—C14—H13	109.9	C41—C42—H56	109.5
C15—C14—H12	110.0	H54—C42—H55	109.5
C15—C14—H13	109.8	H54—C42—H56	109.5
H12—C14—H13	109.5	H55—C42—H56	109.5

C11—N2—C14—C15	−172.2 (2)	C16—C17—C18—C19	−179.2 (2)
C14—N2—C11—C10	175.9 (2)	C17—C18—C19—C20	−177.0 (2)
C14—N2—C11—C12	−2.0 (4)	C18—C19—C20—C21	−179.7 (2)
C32—N4—C35—C36	−169.9 (2)	O2—C22—C23—N3	1.7 (4)
C35—N4—C32—C31	165.8 (2)	O2—C22—C23—C24	178.3 (3)
C35—N4—C32—C33	−15.7 (3)	O2—C22—C28—C27	−179.9 (2)
O1—C1—C2—N1	−1.6 (4)	C23—C22—C28—C27	0.3 (5)
O1—C1—C2—C3	178.6 (3)	C28—C22—C23—N3	−178.5 (3)
O1—C1—C7—C6	178.4 (3)	C28—C22—C23—C24	−1.9 (5)
C2—C1—C7—C6	0.5 (5)	N3—C23—C24—C25	177.8 (3)
C7—C1—C2—N1	176.4 (3)	C22—C23—C24—C25	1.4 (6)
C7—C1—C2—C3	−3.4 (5)	C23—C24—C25—C26	0.2 (5)
N1—C2—C3—C4	−176.8 (3)	C24—C25—C26—C27	−0.1 (4)
C1—C2—C3—C4	2.9 (6)	C24—C25—C26—C29	178.2 (3)
C2—C3—C4—C5	0.9 (6)	C25—C26—C27—C28	−1.4 (5)
C3—C4—C5—C6	−2.6 (5)	C25—C26—C29—C30	−36.6 (4)
C3—C4—C5—C8	179.1 (3)	C25—C26—C29—C34	141.8 (2)
C4—C5—C6—C7	0.4 (5)	C27—C26—C29—C30	141.8 (2)
C4—C5—C8—C9	34.2 (4)	C27—C26—C29—C34	−39.8 (4)
C4—C5—C8—C13	−144.6 (2)	C29—C26—C27—C28	−179.8 (3)
C6—C5—C8—C9	−144.2 (3)	C26—C27—C28—C22	1.7 (6)
C6—C5—C8—C13	37.0 (4)	C26—C29—C30—C31	179.7 (2)
C8—C5—C6—C7	178.7 (3)	C26—C29—C34—C33	−178.5 (2)
C5—C6—C7—C1	1.4 (6)	C30—C29—C34—C33	−0.0 (3)
C5—C8—C9—C10	−179.6 (2)	C34—C29—C30—C31	1.2 (3)
C5—C8—C13—C12	179.0 (2)	C29—C30—C31—C32	−2.2 (3)
C9—C8—C13—C12	0.1 (3)	C30—C31—C32—N4	−179.5 (2)
C13—C8—C9—C10	−0.7 (4)	C30—C31—C32—C33	1.9 (3)
C8—C9—C10—C11	0.8 (4)	N4—C32—C33—C34	−179.2 (2)
C9—C10—C11—N2	−178.1 (2)	C31—C32—C33—C34	−0.7 (3)
C9—C10—C11—C12	−0.1 (3)	C32—C33—C34—C29	−0.2 (4)
N2—C11—C12—C13	177.4 (2)	N4—C35—C36—C37	−174.9 (2)
C10—C11—C12—C13	−0.5 (4)	C35—C36—C37—C38	−177.3 (2)
C11—C12—C13—C8	0.5 (4)	C36—C37—C38—C39	−179.0 (2)
N2—C14—C15—C16	179.9 (2)	C37—C38—C39—C40	−178.1 (2)
C14—C15—C16—C17	171.3 (2)	C38—C39—C40—C41	179.2 (2)
C15—C16—C17—C18	178.8 (2)	C39—C40—C41—C42	178.3 (2)

Symmetry codes: (i) −x−1, −y, −z+2; (ii) x−1, y−1, z; (iii) x−1, y, z; (iv) −x−2, −y, −z+2; (v) x+1, y, z; (vi) −x−1, −y+1, −z+2; (vii) x+1, y+1, z; (viii) −x+3, −y+1, −z+1; (ix) x, y−1, z; (x) x−2, y, z; (xi) x, y+1, z; (xii) −x+2, −y+1, −z+1; (xiii) −x+2, −y+2, −z+1; (xiv) −x+3, −y+2, −z+1; (xv) −x, −y+1, −z+2; (xvi) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.89 (3)	2.13 (2)	2.570 (2)	109 (2)
N2—H11···O2^v	0.93 (3)	2.07 (3)	2.993 (3)	168 (2)
N3—H29···O2	0.87 (3)	2.11 (2)	2.579 (3)	113 (2)
N3—H30···O1ⁱ	0.97 (3)	1.90 (3)	2.845 (3)	165 (3)
N4—H39···O1^vii	0.98 (3)	2.02 (3)	2.993 (4)	170 (2)

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

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