2,6-Bis(4-amino­phen­yl)benzo[1,2-d:5,4-d']dioxazole 1-methyl­pyrrolidin-2-one trisolvate

The title compound, C₂₀H₁₄N₄O₂·3C₅H₉NO, crystallizes with three mol­ecules of 1-methyl-2-pyrrolidinone. The amino groups at each end of the fused-ring heterocycle each inter­act with two of the solvent mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.066
• wR factor = 0.184
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.654     0.983
            Tmin(prime) and Tmax expected:      0.965     0.982
            RR(prime) =      0.677
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.68

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.63
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   N6     -   C26     ..       8.97 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C27    -   C28     ..       7.00 su
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C28
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C5 H9 N O

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

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

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Computing details

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2,6-Bis(4-aminophenyl)benzo[1,2 - d:5,4 - d']dioxazole 1-methylpyrrolidin-2-one trisolvate

Crystal data

C20H14N4O2·3C5H9NO	Z = 2
Mr = 639.75	F(000) = 680
Triclinic, P1	Dx = 1.293 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.586 (2) Å	Cell parameters from 14761 reflections
b = 12.525 (2) Å	θ = 3.0–27.4°
c = 17.627 (2) Å	µ = 0.09 mm^−1
α = 94.92 (1)°	T = 295 K
β = 92.88 (2)°	Prism, yellow
γ = 99.19 (1)°	0.39 × 0.27 × 0.20 mm
V = 1643.8 (6) Å^3

Data collection

Rigaku R-AXIS RAPID IP diffractometer	7333 independent reflections
Radiation source: fine-focus sealed tube	4014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 27.4°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.654, Tmax = 0.983	k = −16→16
15592 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.184	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0898P)^2 + 0.1894P] where P = (Fo^2 + 2Fc^2)/3
7333 reflections	(Δ/σ)max = 0.001
427 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.3373 (2)	0.9225 (1)	0.5646 (1)	0.047 (1)
O2	0.3879 (2)	0.6985 (1)	0.3273 (1)	0.046 (1)
O3	0.1506 (3)	1.3944 (2)	0.8979 (1)	0.083 (1)
O4	0.2400 (4)	0.0954 (2)	0.0543 (1)	0.104 (1)
O5	0.8782 (3)	0.7872 (2)	0.4205 (1)	0.098 (1)
N1	0.2605 (4)	1.1666 (2)	0.8927 (1)	0.079 (1)
N2	0.4007 (3)	0.7904 (1)	0.6356 (1)	0.045 (1)
N3	0.4552 (3)	0.5618 (1)	0.3922 (1)	0.044 (1)
N4	0.3669 (4)	0.3433 (2)	0.0420 (1)	0.076 (1)
N5	0.0963 (3)	1.4981 (2)	0.8021 (2)	0.069 (1)
N6	0.1999 (3)	−0.0083 (2)	0.1526 (2)	0.077 (1)
N7	0.8890 (3)	0.8021 (2)	0.5503 (1)	0.062 (1)
C1	0.2831 (4)	1.0996 (2)	0.8299 (1)	0.054 (1)
C2	0.3174 (4)	0.9937 (2)	0.8372 (1)	0.057 (1)
C3	0.3421 (3)	0.9263 (2)	0.7747 (1)	0.050 (1)
C4	0.3340 (3)	0.9603 (2)	0.7011 (1)	0.042 (1)
C5	0.3007 (3)	1.0659 (2)	0.6936 (1)	0.048 (1)
C6	0.2769 (3)	1.1335 (2)	0.7567 (1)	0.053 (1)
C7	0.3597 (3)	0.8869 (2)	0.6360 (1)	0.042 (1)
C8	0.3655 (3)	0.8370 (2)	0.5147 (1)	0.041 (1)
C9	0.3555 (3)	0.8310 (2)	0.4362 (1)	0.048 (1)
C10	0.3898 (3)	0.7329 (2)	0.4040 (1)	0.040 (1)
C11	0.4325 (3)	0.6481 (2)	0.4448 (1)	0.039 (1)
C12	0.4404 (3)	0.6567 (2)	0.5239 (1)	0.045 (1)
C13	0.4062 (3)	0.7544 (2)	0.5583 (1)	0.040 (1)
C14	0.4272 (3)	0.5943 (2)	0.3260 (1)	0.041 (1)
C15	0.4224 (3)	0.5330 (2)	0.2517 (1)	0.041 (1)
C16	0.3888 (4)	0.5779 (2)	0.1842 (1)	0.054 (1)
C17	0.3719 (4)	0.5158 (2)	0.1150 (1)	0.058 (1)
C18	0.3870 (3)	0.4064 (2)	0.1101 (1)	0.053 (1)
C19	0.4267 (3)	0.3617 (2)	0.1783 (1)	0.049 (1)
C20	0.4436 (3)	0.4237 (2)	0.2473 (1)	0.045 (1)
C21	0.0789 (4)	1.4137 (3)	0.7399 (2)	0.089 (1)
C22	0.0752 (4)	1.6075 (2)	0.7882 (2)	0.069 (1)
C23	0.1052 (5)	1.6697 (3)	0.8680 (2)	0.082 (1)
C24	0.1341 (4)	1.5884 (2)	0.9225 (2)	0.073 (1)
C25	0.1288 (4)	1.4815 (2)	0.8732 (2)	0.066 (1)
C26	0.1740 (5)	0.0764 (3)	0.2098 (2)	0.086 (1)
C27	0.2067 (4)	−0.1175 (2)	0.1732 (2)	0.077 (1)
C28	0.2326 (5)	−0.1800 (3)	0.0971 (2)	0.099 (1)
C29	0.2484 (5)	−0.1002 (3)	0.0392 (2)	0.087 (1)
C30	0.2290 (4)	0.0089 (3)	0.0828 (2)	0.077 (1)
C31	0.8935 (4)	0.7485 (2)	0.4815 (2)	0.065 (1)
C32	0.9199 (4)	0.6342 (2)	0.4919 (2)	0.072 (1)
C33	0.9406 (4)	0.6293 (2)	0.5778 (2)	0.074 (1)
C34	0.8991 (4)	0.7368 (2)	0.6138 (2)	0.065 (1)
C35	0.8528 (4)	0.9113 (2)	0.5616 (2)	0.077 (1)
H1n1	0.2418	1.2317	0.8877	0.094*
H1n2	0.2649	1.1438	0.9373	0.094*
H4n1	0.3441	0.3712	0.0004	0.091*
H4n2	0.3770	0.2758	0.0408	0.091*
H2	0.3233	0.9691	0.8854	0.068*
H3	0.3646	0.8567	0.7812	0.060*
H5	0.2946	1.0906	0.6454	0.058*
H6	0.2562	1.2035	0.7503	0.064*
H9	0.3286	0.8866	0.4082	0.058*
H12	0.4669	0.6010	0.5518	0.054*
H16	0.3775	0.6508	0.1857	0.065*
H17	0.3500	0.5479	0.0705	0.070*
H19	0.4416	0.2893	0.1767	0.059*
H20	0.4695	0.3926	0.2917	0.054*
H21a	0.1803	1.4260	0.7094	0.133*
H21b	−0.0286	1.4144	0.7089	0.133*
H21c	0.0734	1.3444	0.7599	0.133*
H22a	−0.0437	1.6094	0.7660	0.083*
H22b	0.1631	1.6377	0.7544	0.083*
H23a	0.2089	1.7265	0.8702	0.098*
H23b	0.0016	1.7026	0.8804	0.098*
H24a	0.0406	1.5817	0.9581	0.088*
H24b	0.2489	1.6095	0.9509	0.088*
H26a	0.2804	0.0966	0.2431	0.129*
H26b	0.0751	0.0505	0.2389	0.129*
H26c	0.1493	0.1386	0.1854	0.129*
H27a	0.0963	−0.1482	0.1943	0.092*
H27b	0.3061	−0.1180	0.2099	0.092*
H28a	0.3400	−0.2126	0.1009	0.118*
H28b	0.1311	−0.2372	0.0831	0.118*
H29a	0.1548	−0.1209	−0.0013	0.105*
H29b	0.3637	−0.0952	0.0172	0.105*
H32a	1.0261	0.6179	0.4679	0.086*
H32b	0.8174	0.5825	0.4697	0.086*
H33a	1.0616	0.6205	0.5932	0.089*
H33b	0.8580	0.5688	0.5932	0.089*
H34a	0.7864	0.7260	0.6380	0.078*
H34b	0.9932	0.7709	0.6516	0.078*
H35a	0.9544	0.9572	0.5883	0.115*
H35b	0.7500	0.9123	0.5911	0.115*
H35c	0.8298	0.9373	0.5130	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.065 (1)	0.036 (1)	0.041 (1)	0.015 (1)	0.005 (1)	0.003 (1)
O2	0.067 (1)	0.037 (1)	0.037 (1)	0.014 (1)	0.002 (1)	0.005 (1)
O3	0.097 (2)	0.066 (1)	0.091 (2)	0.020 (1)	0.001 (1)	0.033 (1)
O4	0.174 (3)	0.059 (1)	0.082 (2)	0.017 (1)	−0.002 (2)	0.025 (1)
O5	0.111 (2)	0.127 (2)	0.068 (2)	0.042 (2)	0.007 (1)	0.038 (2)
N1	0.127 (2)	0.062 (2)	0.049 (2)	0.031 (2)	0.004 (1)	−0.009 (1)
N2	0.057 (1)	0.039 (1)	0.041 (1)	0.013 (1)	0.002 (1)	0.004 (1)
N3	0.056 (1)	0.038 (1)	0.040 (1)	0.014 (1)	0.001 (1)	0.003 (1)
N4	0.117 (2)	0.062 (1)	0.046 (1)	0.021 (1)	−0.007 (1)	−0.009 (1)
N5	0.065 (2)	0.070 (2)	0.076 (2)	0.016 (1)	0.003 (1)	0.017 (1)
N6	0.074 (2)	0.081 (2)	0.078 (2)	0.011 (1)	0.001 (1)	0.021 (2)
N7	0.062 (1)	0.057 (1)	0.068 (2)	0.011 (1)	0.005 (1)	0.016 (1)
C1	0.065 (2)	0.052 (1)	0.045 (2)	0.012 (1)	0.001 (1)	−0.006 (1)
C2	0.076 (2)	0.057 (2)	0.038 (1)	0.015 (1)	0.002 (1)	0.008 (1)
C3	0.062 (2)	0.043 (1)	0.046 (2)	0.015 (1)	0.002 (1)	0.006 (1)
C4	0.045 (1)	0.039 (1)	0.041 (1)	0.007 (1)	0.003 (1)	0.003 (1)
C5	0.061 (2)	0.043 (1)	0.042 (1)	0.014 (1)	0.006 (1)	0.005 (1)
C6	0.071 (2)	0.039 (1)	0.054 (2)	0.017 (1)	0.007 (1)	0.003 (1)
C7	0.046 (1)	0.039 (1)	0.041 (1)	0.006 (1)	0.002 (1)	0.007 (1)
C8	0.048 (1)	0.033 (1)	0.044 (1)	0.010 (1)	0.004 (1)	0.002 (1)
C9	0.070 (2)	0.036 (1)	0.043 (1)	0.015 (1)	0.002 (1)	0.010 (1)
C10	0.049 (1)	0.037 (1)	0.035 (1)	0.007 (1)	0.001 (1)	0.004 (1)
C11	0.045 (1)	0.032 (1)	0.042 (1)	0.010 (1)	0.002 (1)	0.003 (1)
C12	0.058 (1)	0.037 (1)	0.043 (1)	0.016 (1)	0.000 (1)	0.007 (1)
C13	0.047 (1)	0.038 (1)	0.037 (1)	0.009 (1)	−0.001 (1)	0.006 (1)
C14	0.047 (1)	0.033 (1)	0.044 (1)	0.008 (1)	0.002 (1)	0.005 (1)
C15	0.045 (1)	0.039 (1)	0.040 (1)	0.009 (1)	0.001 (1)	0.002 (1)
C16	0.080 (2)	0.039 (1)	0.044 (2)	0.014 (1)	−0.001 (1)	0.005 (1)
C17	0.085 (2)	0.052 (1)	0.038 (1)	0.012 (1)	−0.004 (1)	0.008 (1)
C18	0.065 (2)	0.050 (1)	0.040 (1)	0.009 (1)	−0.002 (1)	−0.005 (1)
C19	0.065 (2)	0.035 (1)	0.048 (2)	0.014 (1)	0.002 (1)	−0.001 (1)
C20	0.051 (1)	0.043 (1)	0.041 (1)	0.011 (1)	0.001 (1)	0.008 (1)
C21	0.075 (2)	0.094 (2)	0.094 (3)	0.019 (2)	−0.005 (2)	−0.017 (2)
C22	0.069 (2)	0.070 (2)	0.074 (2)	0.018 (1)	−0.002 (2)	0.027 (2)
C23	0.096 (2)	0.067 (2)	0.087 (2)	0.020 (2)	0.012 (2)	0.017 (2)
C24	0.079 (2)	0.073 (2)	0.069 (2)	0.013 (2)	0.005 (2)	0.016 (2)
C25	0.055 (2)	0.075 (2)	0.073 (2)	0.009 (1)	0.006 (1)	0.028 (2)
C26	0.082 (2)	0.090 (2)	0.081 (2)	0.011 (2)	0.007 (2)	−0.011 (2)
C27	0.081 (2)	0.074 (2)	0.080 (2)	0.013 (2)	0.008 (2)	0.032 (2)
C28	0.104 (3)	0.071 (2)	0.125 (3)	0.015 (2)	0.024 (2)	0.029 (2)
C29	0.114 (3)	0.072 (2)	0.076 (2)	0.015 (2)	0.001 (2)	0.011 (2)
C30	0.085 (2)	0.067 (2)	0.077 (2)	0.007 (2)	−0.006 (2)	0.019 (2)
C31	0.055 (2)	0.080 (2)	0.064 (2)	0.013 (1)	0.003 (1)	0.019 (2)
C32	0.063 (2)	0.072 (2)	0.082 (2)	0.018 (2)	−0.003 (2)	0.001 (2)
C33	0.070 (2)	0.066 (2)	0.091 (2)	0.010 (2)	0.008 (2)	0.028 (2)
C34	0.062 (2)	0.070 (1)	0.064 (2)	0.008 (1)	0.002 (1)	0.022 (2)
C35	0.076 (2)	0.058 (2)	0.099 (3)	0.014 (2)	0.006 (2)	0.016 (2)

Geometric parameters (Å, º)

O1—C8	1.378 (3)	C28—C29	1.484 (4)
O1—C7	1.383 (3)	C29—C30	1.540 (4)
O2—C10	1.381 (3)	C31—C32	1.503 (4)
O2—C14	1.383 (2)	C32—C33	1.523 (4)
O3—C25	1.241 (3)	C33—C34	1.525 (4)
O4—C30	1.227 (3)	N1—H1n1	0.86
O5—C31	1.224 (3)	N1—H1n2	0.86
N1—C1	1.366 (3)	N4—H4n1	0.86
N2—C7	1.294 (3)	N4—H4n2	0.86
N2—C13	1.403 (3)	C2—H2	0.93
N3—C14	1.288 (3)	C3—H3	0.93
N3—C11	1.400 (3)	C5—H5	0.93
N4—C18	1.367 (3)	C6—H6	0.93
N5—C25	1.306 (4)	C9—H9	0.93
N5—C21	1.442 (4)	C12—H12	0.93
N5—C22	1.445 (3)	C16—H16	0.93
N6—C30	1.291 (4)	C17—H17	0.93
N6—C26	1.444 (4)	C19—H19	0.93
N6—C27	1.454 (4)	C20—H20	0.93
N7—C31	1.339 (4)	C21—H21a	0.96
N7—C35	1.437 (3)	C21—H21b	0.96
N7—C34	1.448 (3)	C21—H21c	0.96
C1—C6	1.394 (3)	C22—H22a	0.97
C1—C2	1.406 (3)	C22—H22b	0.97
C2—C3	1.369 (3)	C23—H23a	0.97
C3—C4	1.401 (3)	C23—H23b	0.97
C4—C5	1.401 (3)	C24—H24a	0.97
C4—C7	1.449 (3)	C24—H24b	0.97
C5—C6	1.376 (3)	C26—H26a	0.96
C8—C9	1.376 (3)	C26—H26b	0.96
C8—C13	1.403 (3)	C26—H26c	0.96
C9—C10	1.378 (3)	C27—H27a	0.97
C10—C11	1.403 (3)	C27—H27b	0.97
C11—C12	1.386 (3)	C28—H28a	0.97
C12—C13	1.386 (3)	C28—H28b	0.97
C14—C15	1.456 (3)	C29—H29a	0.97
C15—C16	1.389 (3)	C29—H29b	0.97
C15—C20	1.400 (3)	C32—H32a	0.97
C16—C17	1.378 (3)	C32—H32b	0.97
C17—C18	1.389 (3)	C33—H33a	0.97
C18—C19	1.408 (3)	C33—H33b	0.97
C19—C20	1.373 (3)	C34—H34a	0.97
C22—C23	1.536 (4)	C34—H34b	0.97
C23—C24	1.491 (4)	C35—H35a	0.96
C24—C25	1.525 (4)	C35—H35b	0.96
C27—C28	1.531 (5)	C35—H35c	0.96
C8—O1—C7	104.36 (16)	C4—C3—H3	119.4
C10—O2—C14	104.36 (16)	C6—C5—H5	119.6
C7—N2—C13	105.28 (18)	C4—C5—H5	119.6
C14—N3—C11	105.50 (18)	C5—C6—H6	119.2
C25—N5—C21	123.3 (3)	C1—C6—H6	119.2
C25—N5—C22	116.0 (3)	C8—C9—H9	123.9
C21—N5—C22	120.7 (3)	C10—C9—H9	123.9
C30—N6—C26	123.1 (3)	C11—C12—H12	122.4
C30—N6—C27	116.4 (3)	C13—C12—H12	122.4
C26—N6—C27	120.4 (3)	C17—C16—H16	119.5
C31—N7—C35	123.7 (3)	C15—C16—H16	119.5
C31—N7—C34	114.8 (2)	C16—C17—H17	119.3
C35—N7—C34	121.0 (3)	C18—C17—H17	119.3
N1—C1—C6	121.7 (2)	C20—C19—H19	119.6
N1—C1—C2	120.8 (2)	C18—C19—H19	119.6
C6—C1—C2	117.4 (2)	C19—C20—H20	119.5
C3—C2—C1	121.3 (2)	C15—C20—H20	119.5
C2—C3—C4	121.1 (2)	N5—C21—H21a	109.5
C3—C4—C5	117.8 (2)	N5—C21—H21b	109.5
C3—C4—C7	119.9 (2)	H21a—C21—H21b	109.5
C5—C4—C7	122.3 (2)	N5—C21—H21c	109.5
C6—C5—C4	120.8 (2)	H21a—C21—H21c	109.5
C5—C6—C1	121.6 (2)	H21b—C21—H21c	109.5
N2—C7—O1	114.7 (2)	N5—C22—H22a	111.0
N2—C7—C4	128.3 (2)	C23—C22—H22a	111.0
O1—C7—C4	116.99 (18)	N5—C22—H22b	111.0
C9—C8—O1	127.3 (2)	C23—C22—H22b	111.0
C9—C8—C13	125.1 (2)	H22a—C22—H22b	109.0
O1—C8—C13	107.59 (19)	C24—C23—H23a	110.4
C8—C9—C10	112.1 (2)	C22—C23—H23a	110.4
C9—C10—O2	127.65 (19)	C24—C23—H23b	110.4
C9—C10—C11	125.1 (2)	C22—C23—H23b	110.4
O2—C10—C11	107.27 (18)	H23a—C23—H23b	108.6
C12—C11—N3	130.58 (19)	C23—C24—H24a	110.6
C12—C11—C10	121.2 (2)	C25—C24—H24a	110.6
N3—C11—C10	108.15 (19)	C23—C24—H24b	110.6
C11—C12—C13	115.2 (2)	C25—C24—H24b	110.6
C12—C13—C8	121.2 (2)	H24a—C24—H24b	108.8
C12—C13—N2	130.7 (2)	N6—C26—H26a	109.5
C8—C13—N2	108.07 (19)	N6—C26—H26b	109.5
N3—C14—O2	114.71 (19)	H26a—C26—H26b	109.5
N3—C14—C15	127.9 (2)	N6—C26—H26c	109.5
O2—C14—C15	117.28 (19)	H26a—C26—H26c	109.5
C16—C15—C20	118.1 (2)	H26b—C26—H26c	109.5
C16—C15—C14	122.1 (2)	N6—C27—H27a	111.1
C20—C15—C14	119.8 (2)	C28—C27—H27a	111.1
C17—C16—C15	121.0 (2)	N6—C27—H27b	111.1
C16—C17—C18	121.4 (2)	C28—C27—H27b	111.1
N4—C18—C17	122.1 (2)	H27a—C27—H27b	109.1
N4—C18—C19	120.3 (2)	C29—C28—H28a	110.4
C17—C18—C19	117.6 (2)	C27—C28—H28a	110.4
C20—C19—C18	120.8 (2)	C29—C28—H28b	110.4
C19—C20—C15	121.0 (2)	C27—C28—H28b	110.4
N5—C22—C23	103.6 (2)	H28a—C28—H28b	108.6
C24—C23—C22	106.5 (3)	C28—C29—H29a	110.7
C23—C24—C25	105.5 (3)	C30—C29—H29a	110.7
O3—C25—N5	126.8 (3)	C28—C29—H29b	110.7
O3—C25—C24	124.8 (3)	C30—C29—H29b	110.7
N5—C25—C24	108.4 (3)	H29a—C29—H29b	108.8
N6—C27—C28	103.2 (3)	C31—C32—H32a	110.7
C29—C28—C27	106.8 (3)	C33—C32—H32a	110.7
C28—C29—C30	105.3 (3)	C31—C32—H32b	110.7
O4—C30—N6	127.4 (3)	C33—C32—H32b	110.7
O4—C30—C29	124.6 (3)	H32a—C32—H32b	108.8
N6—C30—C29	108.0 (3)	C32—C33—H33a	110.5
O5—C31—N7	125.1 (3)	C34—C33—H33a	110.5
O5—C31—C32	126.1 (3)	C32—C33—H33b	110.5
N7—C31—C32	108.8 (3)	C34—C33—H33b	110.5
C31—C32—C33	105.3 (3)	H33a—C33—H33b	108.7
C32—C33—C34	106.0 (2)	N7—C34—H34a	110.9
N7—C34—C33	104.2 (2)	C33—C34—H34a	110.9
C1—N1—H1n1	120.0	N7—C34—H34b	110.9
C1—N1—H1n2	120.0	C33—C34—H34b	110.9
H1n1—N1—H1n2	120.0	H34a—C34—H34b	108.9
C18—N4—H4n1	120.0	N7—C35—H35a	109.5
C18—N4—H4n2	120.0	N7—C35—H35b	109.5
H4n1—N4—H4n2	120.0	H35a—C35—H35b	109.5
C3—C2—H2	119.4	N7—C35—H35c	109.5
C1—C2—H2	119.4	H35a—C35—H35c	109.5
C2—C3—H3	119.4	H35b—C35—H35c	109.5
N1—C1—C2—C3	−179.3 (2)	C10—O2—C14—C15	175.8 (2)
C6—C1—C2—C3	−0.6 (4)	N3—C14—C15—C16	179.3 (2)
C1—C2—C3—C4	0.0 (4)	O2—C14—C15—C16	3.2 (3)
C2—C3—C4—C5	0.3 (4)	N3—C14—C15—C20	2.4 (4)
C2—C3—C4—C7	−179.7 (2)	O2—C14—C15—C20	−173.7 (2)
C3—C4—C5—C6	0.0 (4)	C20—C15—C16—C17	1.7 (4)
C7—C4—C5—C6	−180.0 (2)	C14—C15—C16—C17	−175.2 (2)
C4—C5—C6—C1	−0.6 (4)	C15—C16—C17—C18	0.3 (4)
N1—C1—C6—C5	179.7 (2)	C16—C17—C18—N4	178.6 (2)
C2—C1—C6—C5	0.9 (4)	C16—C17—C18—C19	−2.2 (4)
C13—N2—C7—O1	−0.6 (3)	N4—C18—C19—C20	−178.7 (2)
C13—N2—C7—C4	179.0 (2)	C17—C18—C19—C20	2.1 (4)
C8—O1—C7—N2	0.9 (2)	C18—C19—C20—C15	−0.1 (4)
C8—O1—C7—C4	−178.7 (2)	C16—C15—C20—C19	−1.8 (3)
C3—C4—C7—N2	−4.2 (4)	C14—C15—C20—C19	175.2 (2)
C5—C4—C7—N2	175.8 (2)	C25—N5—C22—C23	1.3 (3)
C3—C4—C7—O1	175.4 (2)	C21—N5—C22—C23	−179.6 (2)
C5—C4—C7—O1	−4.6 (3)	N5—C22—C23—C24	−2.3 (3)
C7—O1—C8—C9	178.8 (2)	C22—C23—C24—C25	2.4 (3)
C7—O1—C8—C13	−0.9 (2)	C21—N5—C25—O3	0.6 (5)
O1—C8—C9—C10	−179.4 (2)	C22—N5—C25—O3	179.7 (3)
C13—C8—C9—C10	0.2 (3)	C21—N5—C25—C24	−178.9 (3)
C8—C9—C10—O2	178.7 (2)	C22—N5—C25—C24	0.2 (3)
C8—C9—C10—C11	−0.7 (3)	C23—C24—C25—O3	178.8 (3)
C14—O2—C10—C9	−178.8 (2)	C23—C24—C25—N5	−1.7 (3)
C14—O2—C10—C11	0.7 (2)	C30—N6—C27—C28	−4.9 (4)
C14—N3—C11—C12	177.6 (2)	C26—N6—C27—C28	179.2 (3)
C14—N3—C11—C10	−0.1 (2)	N6—C27—C28—C29	3.0 (4)
C9—C10—C11—C12	1.1 (4)	C27—C28—C29—C30	−0.7 (4)
O2—C10—C11—C12	−178.4 (2)	C26—N6—C30—O4	0.3 (6)
C9—C10—C11—N3	179.1 (2)	C27—N6—C30—O4	−175.4 (3)
O2—C10—C11—N3	−0.4 (2)	C26—N6—C30—C29	−179.7 (3)
N3—C11—C12—C13	−178.4 (2)	C27—N6—C30—C29	4.6 (4)
C10—C11—C12—C13	−0.9 (3)	C28—C29—C30—O4	177.8 (4)
C11—C12—C13—C8	0.4 (3)	C28—C29—C30—N6	−2.2 (4)
C11—C12—C13—N2	179.1 (2)	C35—N7—C31—O5	4.6 (4)
C9—C8—C13—C12	−0.1 (4)	C34—N7—C31—O5	176.4 (3)
O1—C8—C13—C12	179.5 (2)	C35—N7—C31—C32	−175.4 (2)
C9—C8—C13—N2	−179.1 (2)	C34—N7—C31—C32	−3.6 (3)
O1—C8—C13—N2	0.6 (2)	O5—C31—C32—C33	177.1 (3)
C7—N2—C13—C12	−178.8 (2)	N7—C31—C32—C33	−2.9 (3)
C7—N2—C13—C8	0.0 (2)	C31—C32—C33—C34	7.8 (3)
C11—N3—C14—O2	0.7 (2)	C31—N7—C34—C33	8.4 (3)
C11—N3—C14—C15	−175.6 (2)	C35—N7—C34—C33	−179.5 (2)
C10—O2—C14—N3	−0.9 (2)	C32—C33—C34—N7	−9.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n1···O3	0.86	2.25	3.092 (3)	166
N1—H1n2···O4^i	0.86	2.21	3.060 (3)	172
N4—H4n1···O3^ii	0.86	2.34	3.122 (3)	152
N4—H4n2···O4	0.86	2.37	3.130 (3)	148

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