N-Benzyl-8-nitro­quinolin-2-amine

In the crystal structure of the title compound, C₁₆H₁₃N₃O₂, there are two independent L-shaped mol­ecules in the asymmetric unit. No classical hydrogen bonds were found in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.046
• wR factor = 0.119
• Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.11
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.59
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N6
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2N    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N5     -   H5N    ...          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           67.92
           From the CIF: _reflns_number_total               2497
           Count of symmetry unique reflns         2497
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

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Computing details

Data collection: CAD-4-PC Software (Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N-Benzyl-8-nitroquinolin-2-amine

Crystal data

C16H13N3O2	F(000) = 584
Mr = 279.29	Dx = 1.348 Mg m^−3
Monoclinic, Pc	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P -2yc	Cell parameters from 25 reflections
a = 7.439 (1) Å	θ = 3.9–19.4°
b = 11.215 (1) Å	µ = 0.75 mm^−1
c = 16.541 (1) Å	T = 299 K
β = 93.96 (1)°	Needle, orange
V = 1376.7 (2) Å^3	0.68 × 0.20 × 0.10 mm
Z = 4

Data collection

Nonius CAD-4 diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 67.9°, θmin = 3.9°
Graphite monochromator	h = −8→0
ω/2θ scans	k = −13→1
2913 measured reflections	l = −19→19
2497 independent reflections	3 standard reflections every 120 min
2233 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0853P)^2 + 0.028P] where P = (Fo^2 + 2Fc^2)/3
2497 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.16 e Å^−3
2 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.6479 (4)	0.0074 (2)	0.56618 (15)	0.0832 (8)
O2	0.7853 (5)	−0.1592 (3)	0.55330 (19)	0.0948 (9)
N1	0.8025 (3)	0.1310 (2)	0.43538 (14)	0.0483 (5)
N2	0.9293 (3)	0.3181 (3)	0.43035 (18)	0.0605 (7)
H2N	0.9479	0.3789	0.4002	0.073*
N3	0.7053 (4)	−0.0717 (2)	0.52474 (16)	0.0588 (6)
C1	0.7217 (3)	0.0378 (3)	0.39533 (16)	0.0462 (6)
C2	0.8469 (4)	0.2242 (3)	0.39204 (18)	0.0505 (7)
C3	0.8129 (4)	0.2303 (3)	0.3059 (2)	0.0604 (8)
H3	0.8457	0.2976	0.2775	0.073*
C4	0.7332 (4)	0.1377 (3)	0.26650 (19)	0.0620 (8)
H4	0.7107	0.1407	0.2105	0.074*
C5	0.6829 (4)	0.0351 (3)	0.30994 (17)	0.0529 (7)
C6	0.6003 (4)	−0.0644 (3)	0.2731 (2)	0.0651 (9)
H6	0.5757	−0.0644	0.2172	0.078*
C7	0.5544 (5)	−0.1619 (3)	0.3166 (2)	0.0661 (8)
H7	0.4986	−0.2270	0.2907	0.079*
C8	0.5923 (4)	−0.1624 (3)	0.4001 (2)	0.0603 (8)
H8	0.5636	−0.2287	0.4304	0.072*
C9	0.6720 (4)	−0.0653 (3)	0.43729 (18)	0.0504 (6)
C10	0.9608 (4)	0.3268 (3)	0.5174 (2)	0.0646 (8)
H10A	1.0658	0.3764	0.5301	0.078*
H10B	0.9865	0.2480	0.5395	0.078*
C11	0.8005 (4)	0.3792 (3)	0.55762 (18)	0.0563 (7)
C12	0.7751 (7)	0.5012 (3)	0.5620 (3)	0.0828 (11)
H12	0.8612	0.5523	0.5430	0.099*
C13	0.6242 (9)	0.5482 (5)	0.5940 (3)	0.1075 (18)
H13	0.6086	0.6304	0.5963	0.129*
C14	0.4991 (8)	0.4743 (6)	0.6219 (3)	0.1050 (17)
H14	0.3967	0.5060	0.6430	0.126*
C15	0.5216 (6)	0.3532 (5)	0.6195 (2)	0.0809 (11)
H15	0.4355	0.3032	0.6395	0.097*
C16	0.6725 (5)	0.3054 (3)	0.58721 (19)	0.0618 (8)
H16	0.6874	0.2231	0.5855	0.074*
O3	0.1486 (5)	0.2968 (2)	0.13557 (17)	0.0872 (8)
O4	0.3004 (6)	0.1769 (4)	0.0676 (2)	0.1184 (12)
N4	0.2999 (3)	0.2281 (2)	0.29424 (14)	0.0507 (6)
N5	0.4277 (4)	0.3376 (3)	0.40077 (18)	0.0663 (7)
H5N	0.4694	0.3440	0.4502	0.080*
N6	0.2144 (4)	0.2006 (3)	0.12596 (18)	0.0671 (7)
C17	0.2232 (3)	0.1241 (3)	0.26696 (19)	0.0499 (6)
C18	0.3450 (4)	0.2359 (3)	0.37237 (19)	0.0549 (7)
C19	0.3129 (4)	0.1431 (4)	0.4288 (2)	0.0657 (9)
H19	0.3458	0.1528	0.4836	0.079*
C20	0.2355 (4)	0.0426 (4)	0.4017 (2)	0.0663 (9)
H20	0.2132	−0.0181	0.4380	0.080*
C21	0.1865 (4)	0.0272 (3)	0.3178 (2)	0.0598 (8)
C22	0.1118 (5)	−0.0777 (3)	0.2848 (3)	0.0768 (11)
H22	0.0852	−0.1396	0.3194	0.092*
C23	0.0767 (6)	−0.0923 (4)	0.2038 (3)	0.0828 (11)
H23	0.0276	−0.1633	0.1834	0.099*
C24	0.1147 (5)	−0.0001 (3)	0.1517 (3)	0.0724 (9)
H24	0.0936	−0.0093	0.0960	0.087*
C25	0.1841 (4)	0.1053 (3)	0.1832 (2)	0.0567 (7)
C26	0.4415 (4)	0.4442 (3)	0.3536 (2)	0.0658 (8)
H26A	0.4711	0.4229	0.2993	0.079*
H26B	0.5388	0.4931	0.3775	0.079*
C27	0.2689 (4)	0.5159 (3)	0.3488 (2)	0.0547 (7)
C28	0.2263 (5)	0.5870 (3)	0.4127 (2)	0.0669 (9)
H28	0.3081	0.5953	0.4575	0.080*
C29	0.0630 (7)	0.6461 (3)	0.4108 (3)	0.0805 (11)
H29	0.0359	0.6943	0.4540	0.097*
C30	−0.0576 (7)	0.6340 (3)	0.3463 (3)	0.0839 (12)
H30	−0.1672	0.6740	0.3457	0.101*
C31	−0.0202 (5)	0.5637 (4)	0.2819 (3)	0.0747 (10)
H31	−0.1038	0.5558	0.2378	0.090*
C32	0.1439 (5)	0.5041 (3)	0.2831 (2)	0.0602 (8)
H32	0.1700	0.4561	0.2396	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.123 (2)	0.0750 (15)	0.0531 (13)	−0.0014 (15)	0.0195 (14)	0.0002 (12)
O2	0.117 (2)	0.0860 (18)	0.0783 (18)	0.0235 (18)	−0.0164 (17)	0.0178 (15)
N1	0.0330 (11)	0.0640 (14)	0.0488 (12)	0.0063 (10)	0.0094 (9)	0.0059 (11)
N2	0.0479 (14)	0.0699 (16)	0.0655 (15)	−0.0020 (12)	0.0175 (12)	0.0104 (13)
N3	0.0659 (17)	0.0584 (15)	0.0517 (14)	−0.0065 (13)	0.0005 (12)	0.0047 (12)
C1	0.0317 (13)	0.0605 (16)	0.0472 (14)	0.0124 (11)	0.0089 (11)	0.0014 (12)
C2	0.0308 (13)	0.0645 (18)	0.0578 (16)	0.0076 (12)	0.0143 (11)	0.0083 (14)
C3	0.0430 (16)	0.081 (2)	0.0595 (18)	0.0107 (15)	0.0206 (14)	0.0172 (16)
C4	0.0508 (17)	0.092 (2)	0.0441 (15)	0.0162 (17)	0.0102 (13)	0.0079 (16)
C5	0.0352 (14)	0.078 (2)	0.0468 (14)	0.0160 (13)	0.0105 (11)	0.0006 (14)
C6	0.0529 (18)	0.091 (2)	0.0516 (17)	0.0201 (17)	0.0028 (13)	−0.0132 (17)
C7	0.0566 (18)	0.071 (2)	0.070 (2)	0.0100 (16)	−0.0005 (15)	−0.0149 (17)
C8	0.0573 (19)	0.0599 (17)	0.0637 (19)	0.0103 (15)	0.0033 (14)	−0.0051 (14)
C9	0.0406 (14)	0.0586 (16)	0.0526 (15)	0.0109 (12)	0.0070 (12)	−0.0017 (12)
C10	0.0443 (17)	0.077 (2)	0.072 (2)	−0.0063 (15)	−0.0015 (14)	0.0044 (17)
C11	0.0547 (16)	0.0664 (17)	0.0471 (15)	−0.0025 (14)	−0.0022 (12)	0.0017 (13)
C12	0.108 (3)	0.065 (2)	0.076 (2)	−0.003 (2)	0.017 (2)	0.0035 (18)
C13	0.155 (5)	0.086 (3)	0.084 (3)	0.037 (3)	0.027 (3)	−0.001 (2)
C14	0.115 (4)	0.139 (5)	0.063 (2)	0.048 (4)	0.021 (2)	−0.003 (3)
C15	0.068 (2)	0.118 (3)	0.058 (2)	0.004 (2)	0.0135 (16)	0.002 (2)
C16	0.0587 (18)	0.073 (2)	0.0536 (16)	−0.0015 (16)	0.0025 (13)	−0.0012 (15)
O3	0.123 (2)	0.0691 (15)	0.0680 (15)	0.0051 (16)	−0.0037 (15)	0.0073 (13)
O4	0.135 (3)	0.136 (3)	0.091 (2)	0.024 (3)	0.054 (2)	0.022 (2)
N4	0.0319 (11)	0.0672 (15)	0.0533 (13)	0.0110 (10)	0.0047 (10)	0.0053 (11)
N5	0.0482 (15)	0.0868 (19)	0.0623 (16)	0.0112 (14)	−0.0082 (12)	−0.0016 (14)
N6	0.0672 (18)	0.0761 (19)	0.0576 (15)	0.0016 (15)	0.0019 (13)	0.0001 (14)
C17	0.0294 (13)	0.0602 (16)	0.0605 (16)	0.0130 (12)	0.0068 (11)	0.0065 (13)
C18	0.0326 (14)	0.075 (2)	0.0570 (16)	0.0182 (13)	0.0033 (12)	0.0036 (14)
C19	0.0476 (17)	0.095 (3)	0.0547 (17)	0.0268 (18)	0.0067 (13)	0.0130 (17)
C20	0.0506 (17)	0.078 (2)	0.073 (2)	0.0183 (16)	0.0175 (15)	0.0277 (18)
C21	0.0369 (15)	0.0675 (19)	0.076 (2)	0.0123 (13)	0.0114 (14)	0.0179 (16)
C22	0.057 (2)	0.065 (2)	0.110 (3)	0.0013 (17)	0.018 (2)	0.018 (2)
C23	0.064 (2)	0.072 (2)	0.111 (3)	−0.0054 (19)	0.001 (2)	−0.001 (2)
C24	0.061 (2)	0.072 (2)	0.084 (2)	0.0044 (17)	−0.0035 (18)	−0.0066 (18)
C25	0.0414 (15)	0.0633 (17)	0.0661 (18)	0.0105 (13)	0.0077 (13)	0.0053 (14)
C26	0.0383 (16)	0.084 (2)	0.076 (2)	−0.0065 (16)	0.0044 (13)	−0.0047 (19)
C27	0.0516 (16)	0.0555 (16)	0.0575 (16)	−0.0101 (13)	0.0066 (12)	0.0024 (13)
C28	0.079 (2)	0.0577 (18)	0.0638 (19)	−0.0130 (17)	0.0030 (17)	−0.0019 (14)
C29	0.108 (3)	0.0545 (18)	0.082 (2)	0.008 (2)	0.031 (2)	−0.0018 (17)
C30	0.081 (3)	0.062 (2)	0.110 (3)	0.021 (2)	0.020 (2)	0.012 (2)
C31	0.065 (2)	0.072 (2)	0.085 (2)	0.0080 (18)	−0.0098 (18)	0.0122 (19)
C32	0.0598 (18)	0.0660 (18)	0.0555 (16)	0.0010 (15)	0.0076 (13)	0.0019 (14)

Geometric parameters (Å, º)

O1—N3	1.217 (4)	O3—N6	1.200 (4)
O2—N3	1.225 (4)	O4—N6	1.224 (4)
N1—C2	1.323 (4)	N4—C18	1.316 (4)
N1—C1	1.356 (4)	N4—C17	1.362 (4)
N2—C2	1.354 (4)	N5—C18	1.364 (5)
N2—C10	1.446 (5)	N5—C26	1.435 (5)
N2—H2N	0.8617	N5—H5N	0.8571
N3—C9	1.452 (4)	N6—C25	1.455 (4)
C1—C9	1.411 (4)	C17—C21	1.412 (4)
C1—C5	1.422 (4)	C17—C25	1.412 (4)
C2—C3	1.432 (4)	C18—C19	1.429 (5)
C3—C4	1.342 (5)	C19—C20	1.328 (5)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.420 (5)	C20—C21	1.422 (5)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.393 (5)	C21—C22	1.396 (6)
C6—C7	1.365 (6)	C22—C23	1.357 (6)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.390 (5)	C23—C24	1.387 (6)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.366 (4)	C24—C25	1.377 (5)
C8—H8	0.9300	C24—H24	0.9300
C10—C11	1.522 (5)	C26—C27	1.512 (5)
C10—H10A	0.9700	C26—H26A	0.9700
C10—H10B	0.9700	C26—H26B	0.9700
C11—C16	1.377 (5)	C27—C28	1.379 (5)
C11—C12	1.385 (5)	C27—C32	1.388 (5)
C12—C13	1.378 (7)	C28—C29	1.382 (6)
C12—H12	0.9300	C28—H28	0.9300
C13—C14	1.351 (8)	C29—C30	1.352 (7)
C13—H13	0.9300	C29—H29	0.9300
C14—C15	1.369 (7)	C30—C31	1.370 (6)
C14—H14	0.9300	C30—H30	0.9300
C15—C16	1.384 (5)	C31—C32	1.391 (5)
C15—H15	0.9300	C31—H31	0.9300
C16—H16	0.9300	C32—H32	0.9300
C2—N1—C1	117.6 (2)	C18—N4—C17	117.1 (3)
C2—N2—C10	123.8 (3)	C18—N5—C26	123.9 (3)
C2—N2—H2N	115.5	C18—N5—H5N	121.5
C10—N2—H2N	120.1	C26—N5—H5N	114.5
O1—N3—O2	123.2 (3)	O3—N6—O4	122.7 (4)
O1—N3—C9	118.9 (3)	O3—N6—C25	119.4 (3)
O2—N3—C9	117.9 (3)	O4—N6—C25	117.8 (3)
N1—C1—C9	120.9 (2)	N4—C17—C21	123.8 (3)
N1—C1—C5	123.7 (3)	N4—C17—C25	120.4 (3)
C9—C1—C5	115.4 (3)	C21—C17—C25	115.7 (3)
N1—C2—N2	118.9 (3)	N4—C18—N5	118.2 (3)
N1—C2—C3	122.9 (3)	N4—C18—C19	123.4 (3)
N2—C2—C3	118.2 (3)	N5—C18—C19	118.4 (3)
C4—C3—C2	119.2 (3)	C20—C19—C18	119.1 (3)
C4—C3—H3	120.4	C20—C19—H19	120.4
C2—C3—H3	120.4	C18—C19—H19	120.4
C3—C4—C5	120.3 (3)	C19—C20—C21	120.5 (3)
C3—C4—H4	119.9	C19—C20—H20	119.7
C5—C4—H4	119.9	C21—C20—H20	119.7
C6—C5—C4	123.4 (3)	C22—C21—C17	120.3 (4)
C6—C5—C1	120.3 (3)	C22—C21—C20	123.6 (3)
C4—C5—C1	116.3 (3)	C17—C21—C20	116.1 (3)
C7—C6—C5	122.0 (3)	C23—C22—C21	122.1 (4)
C7—C6—H6	119.0	C23—C22—H22	118.9
C5—C6—H6	119.0	C21—C22—H22	118.9
C6—C7—C8	119.1 (3)	C22—C23—C24	119.3 (4)
C6—C7—H7	120.5	C22—C23—H23	120.4
C8—C7—H7	120.5	C24—C23—H23	120.4
C9—C8—C7	119.8 (3)	C25—C24—C23	119.5 (4)
C9—C8—H8	120.1	C25—C24—H24	120.2
C7—C8—H8	120.1	C23—C24—H24	120.2
C8—C9—C1	123.5 (3)	C24—C25—C17	123.0 (3)
C8—C9—N3	116.6 (3)	C24—C25—N6	117.1 (3)
C1—C9—N3	119.9 (3)	C17—C25—N6	119.9 (3)
N2—C10—C11	112.5 (3)	N5—C26—C27	112.3 (3)
N2—C10—H10A	109.1	N5—C26—H26A	109.2
C11—C10—H10A	109.1	C27—C26—H26A	109.2
N2—C10—H10B	109.1	N5—C26—H26B	109.2
C11—C10—H10B	109.1	C27—C26—H26B	109.2
H10A—C10—H10B	107.8	H26A—C26—H26B	107.9
C16—C11—C12	118.4 (4)	C28—C27—C32	118.6 (3)
C16—C11—C10	120.4 (3)	C28—C27—C26	120.4 (3)
C12—C11—C10	121.2 (3)	C32—C27—C26	120.8 (3)
C13—C12—C11	121.1 (4)	C27—C28—C29	120.5 (4)
C13—C12—H12	119.5	C27—C28—H28	119.7
C11—C12—H12	119.5	C29—C28—H28	119.7
C14—C13—C12	119.7 (5)	C30—C29—C28	120.3 (4)
C14—C13—H13	120.2	C30—C29—H29	119.9
C12—C13—H13	120.2	C28—C29—H29	119.9
C13—C14—C15	120.6 (5)	C29—C30—C31	120.8 (4)
C13—C14—H14	119.7	C29—C30—H30	119.6
C15—C14—H14	119.7	C31—C30—H30	119.6
C14—C15—C16	120.0 (4)	C30—C31—C32	119.4 (4)
C14—C15—H15	120.0	C30—C31—H31	120.3
C16—C15—H15	120.0	C32—C31—H31	120.3
C11—C16—C15	120.2 (4)	C27—C32—C31	120.4 (3)
C11—C16—H16	119.9	C27—C32—H32	119.8
C15—C16—H16	119.9	C31—C32—H32	119.8
C2—N1—C1—C9	179.4 (2)	C18—N4—C17—C21	1.6 (4)
C2—N1—C1—C5	0.2 (3)	C18—N4—C17—C25	−175.0 (2)
C1—N1—C2—N2	−179.4 (2)	C17—N4—C18—N5	177.8 (2)
C1—N1—C2—C3	0.1 (4)	C17—N4—C18—C19	−1.8 (4)
C10—N2—C2—N1	−4.6 (4)	C26—N5—C18—N4	10.9 (4)
C10—N2—C2—C3	175.8 (3)	C26—N5—C18—C19	−169.5 (3)
N1—C2—C3—C4	−0.3 (4)	N4—C18—C19—C20	0.8 (4)
N2—C2—C3—C4	179.3 (3)	N5—C18—C19—C20	−178.8 (3)
C2—C3—C4—C5	0.1 (4)	C18—C19—C20—C21	0.5 (4)
C3—C4—C5—C6	−179.8 (3)	N4—C17—C21—C22	−178.3 (3)
C3—C4—C5—C1	0.1 (4)	C25—C17—C21—C22	−1.6 (4)
N1—C1—C5—C6	179.6 (3)	N4—C17—C21—C20	−0.4 (4)
C9—C1—C5—C6	0.4 (4)	C25—C17—C21—C20	176.4 (3)
N1—C1—C5—C4	−0.3 (4)	C19—C20—C21—C22	177.2 (3)
C9—C1—C5—C4	−179.5 (2)	C19—C20—C21—C17	−0.7 (4)
C4—C5—C6—C7	179.7 (3)	C17—C21—C22—C23	1.9 (5)
C1—C5—C6—C7	−0.2 (4)	C20—C21—C22—C23	−175.9 (3)
C5—C6—C7—C8	−0.5 (5)	C21—C22—C23—C24	−0.5 (6)
C6—C7—C8—C9	1.0 (5)	C22—C23—C24—C25	−1.3 (6)
C7—C8—C9—C1	−0.8 (4)	C23—C24—C25—C17	1.6 (5)
C7—C8—C9—N3	179.2 (3)	C23—C24—C25—N6	−177.5 (3)
N1—C1—C9—C8	−179.1 (3)	N4—C17—C25—C24	176.7 (3)
C5—C1—C9—C8	0.1 (4)	C21—C17—C25—C24	−0.1 (4)
N1—C1—C9—N3	0.9 (4)	N4—C17—C25—N6	−4.2 (4)
C5—C1—C9—N3	−179.9 (2)	C21—C17—C25—N6	179.0 (3)
O1—N3—C9—C8	−126.1 (3)	O3—N6—C25—C24	125.7 (3)
O2—N3—C9—C8	51.6 (4)	O4—N6—C25—C24	−51.1 (5)
O1—N3—C9—C1	53.9 (4)	O3—N6—C25—C17	−53.4 (4)
O2—N3—C9—C1	−128.4 (3)	O4—N6—C25—C17	129.8 (4)
C2—N2—C10—C11	−86.2 (4)	C18—N5—C26—C27	79.1 (4)
N2—C10—C11—C16	93.7 (4)	N5—C26—C27—C28	78.8 (4)
N2—C10—C11—C12	−83.2 (4)	N5—C26—C27—C32	−96.0 (4)
C16—C11—C12—C13	−1.0 (6)	C32—C27—C28—C29	−0.6 (5)
C10—C11—C12—C13	176.0 (4)	C26—C27—C28—C29	−175.5 (3)
C11—C12—C13—C14	0.3 (8)	C27—C28—C29—C30	0.5 (6)
C12—C13—C14—C15	0.6 (8)	C28—C29—C30—C31	−0.2 (6)
C13—C14—C15—C16	−0.8 (7)	C29—C30—C31—C32	0.0 (6)
C12—C11—C16—C15	0.8 (5)	C28—C27—C32—C31	0.4 (5)
C10—C11—C16—C15	−176.2 (3)	C26—C27—C32—C31	175.3 (3)
C14—C15—C16—C11	0.1 (6)	C30—C31—C32—C27	−0.1 (5)