1,2-Bis(3,5-di­methyl­pyrazol-1-yl)-anti-[2.2]­para­cyclo­naphthane

The title compound, C₃₄H₃₃N₄, is a new 3,5-di­methyl­pyrazole-substituted para­cyclo­naphthane. Each of the two symmetry-independent mol­ecules in the asymmetric unit occupies a special position on a twofold axis and exhibits an intramol­ecular π–π stacking interaction between the naphthalene moieties. The geometry of both mol­ecules is essentially the same, the bridged rings of the naphthalene nuclei being deformed into a boat shape.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.145
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.072
            Value of mu given      =     0.070
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.10 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.50 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      39.00 A   3  

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1,2-Bis(3,5-dimethylpyrazol-1-yl)-anti-[2.2]paracyclonaphthane

Crystal data

C34H32N4	Dx = 1.209 Mg m^−3
Mr = 496.64	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Ibca	Cell parameters from 938 reflections
a = 16.6732 (18) Å	θ = 2.8–26.4°
b = 16.674 (2) Å	µ = 0.07 mm^−1
c = 39.267 (8) Å	T = 293 K
V = 10916 (3) Å^3	Prism, colourless
Z = 16	0.32 × 0.26 × 0.16 mm
F(000) = 4224

Data collection

Bruker SMART CCD area-detector diffractometer	3521 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Graphite monochromator	θmax = 26.4°, θmin = 1.0°
φ and ω scans	h = −13→20
30541 measured reflections	k = −20→20
5619 independent reflections	l = −46→49

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0673P)^2 + 3.9798P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
5619 reflections	Δρmax = 0.30 e Å^−3
347 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00047 (8)

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
N1	0.52791 (17)	0.84588 (15)	0.52268 (6)	0.0367 (6)
N2	0.60947 (17)	0.84088 (17)	0.52440 (6)	0.0457 (7)
C1	0.4761 (2)	0.82831 (18)	0.46406 (7)	0.0321 (7)
C2	0.5437 (2)	0.85487 (18)	0.44805 (8)	0.0378 (7)
H2	0.5872	0.8721	0.4609	0.045*
C3	0.5485 (2)	0.85644 (18)	0.41239 (8)	0.0402 (8)
H3	0.5951	0.8749	0.4020	0.048*
C4	0.4862 (2)	0.8314 (2)	0.39261 (7)	0.0388 (8)
C5	0.40990 (19)	0.82178 (19)	0.40847 (7)	0.0393 (8)
C6	0.3394 (2)	0.8080 (2)	0.38930 (8)	0.0556 (10)
H6	0.3419	0.8097	0.3657	0.067*
C7	0.2688 (2)	0.7924 (3)	0.40459 (9)	0.0662 (12)
H7	0.2233	0.7834	0.3914	0.079*
C8	0.2633 (2)	0.7896 (2)	0.43994 (9)	0.0588 (10)
H8	0.2142	0.7790	0.4503	0.071*
C9	0.32916 (19)	0.8024 (2)	0.45932 (8)	0.0440 (8)
H9	0.3246	0.8000	0.4829	0.053*
C10	0.40486 (18)	0.81942 (18)	0.44465 (7)	0.0342 (7)
C11	0.4818 (2)	0.79382 (19)	0.49999 (7)	0.0335 (8)
H11	0.4272	0.7903	0.5091	0.040*
C12	0.5027 (2)	0.7969 (2)	0.35764 (7)	0.0497 (12)
H12A	0.5559	0.8130	0.3503	0.060*
H12B	0.4643	0.8184	0.3415	0.060*
C13	0.5002 (2)	0.9135 (2)	0.53758 (8)	0.0400 (10)
C14	0.5654 (2)	0.9526 (2)	0.55020 (8)	0.0503 (10)
H14	0.5657	1.0007	0.5622	0.060*
C15	0.6314 (2)	0.9062 (2)	0.54159 (8)	0.0493 (9)
C16	0.4133 (2)	0.9346 (2)	0.53808 (10)	0.0612 (11)
H16A	0.3951	0.9439	0.5152	0.092*
H16B	0.4055	0.9822	0.5514	0.092*
H16C	0.3834	0.8912	0.5479	0.092*
C17	0.7178 (2)	0.9215 (3)	0.54951 (11)	0.0827 (14)
H17A	0.7509	0.8926	0.5337	0.124*
H17B	0.7293	0.9038	0.5723	0.124*
H17C	0.7287	0.9779	0.5477	0.124*
N3	0.40497 (14)	0.22133 (17)	0.72563 (6)	0.0360 (6)
N4	0.41191 (16)	0.13985 (17)	0.72280 (6)	0.0460 (7)
C18	0.42118 (18)	0.2706 (2)	0.78436 (7)	0.0341 (7)
C19	0.39728 (18)	0.2021 (2)	0.79998 (7)	0.0366 (7)
H19	0.3812	0.1585	0.7869	0.044*
C20	0.39656 (19)	0.1959 (2)	0.83584 (7)	0.0417 (8)
H20	0.3812	0.1479	0.8460	0.050*
C21	0.4179 (2)	0.2592 (2)	0.85588 (8)	0.0409 (9)
C22	0.42299 (19)	0.3365 (2)	0.84031 (7)	0.0400 (8)
C23	0.4325 (2)	0.4069 (2)	0.85986 (9)	0.0598 (10)
H23	0.4301	0.4037	0.8835	0.072*
C24	0.4450 (3)	0.4793 (2)	0.84487 (10)	0.0697 (12)
H24	0.4500	0.5251	0.8582	0.084*
C25	0.4502 (2)	0.4849 (2)	0.80979 (10)	0.0665 (12)
H25	0.4601	0.5344	0.7997	0.080*
C26	0.4409 (2)	0.4188 (2)	0.78982 (8)	0.0491 (9)
H26	0.4441	0.4240	0.7663	0.059*
C27	0.42665 (18)	0.34221 (19)	0.80423 (7)	0.0356 (7)
C28	0.45589 (18)	0.2671 (2)	0.74867 (6)	0.0332 (8)
H28	0.4583	0.3222	0.7400	0.040*
C29	0.4528 (2)	0.2445 (2)	0.89073 (7)	0.0497 (12)
H29A	0.4396	0.1905	0.8980	0.060*
H29B	0.4290	0.2817	0.9068	0.060*
C30	0.3364 (2)	0.24863 (19)	0.71081 (8)	0.0406 (10)
C31	0.2999 (2)	0.1829 (2)	0.69694 (9)	0.0539 (10)
H31	0.2523	0.1822	0.6846	0.065*
C32	0.3478 (2)	0.1173 (2)	0.70493 (8)	0.0536 (9)
C33	0.3113 (2)	0.3334 (2)	0.71232 (10)	0.0561 (10)
H33A	0.2931	0.3458	0.7349	0.084*
H33B	0.2684	0.3423	0.6964	0.084*
H33C	0.3559	0.3672	0.7066	0.084*
C34	0.3352 (3)	0.0313 (3)	0.69641 (13)	0.0936 (16)
H34A	0.3862	0.0054	0.6937	0.140*
H34B	0.3054	0.0272	0.6756	0.140*
H34C	0.3058	0.0058	0.7144	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0432 (17)	0.0374 (16)	0.0294 (13)	0.0010 (13)	−0.0036 (12)	−0.0058 (11)
N2	0.0407 (16)	0.0517 (18)	0.0447 (15)	0.0031 (13)	−0.0091 (12)	−0.0073 (13)
C1	0.0400 (18)	0.0283 (18)	0.0280 (14)	0.0039 (16)	−0.0002 (14)	0.0003 (13)
C2	0.0407 (19)	0.0318 (18)	0.0408 (17)	−0.0006 (14)	−0.0069 (14)	−0.0011 (14)
C3	0.0446 (19)	0.0358 (19)	0.0402 (17)	−0.0033 (14)	0.0038 (15)	0.0086 (14)
C4	0.053 (2)	0.036 (2)	0.0273 (16)	0.0040 (16)	−0.0004 (14)	0.0088 (15)
C5	0.0433 (19)	0.0398 (19)	0.0347 (15)	0.0022 (15)	−0.0062 (14)	0.0049 (14)
C6	0.053 (2)	0.078 (3)	0.0358 (17)	0.0064 (19)	−0.0110 (16)	0.0022 (16)
C7	0.041 (2)	0.100 (3)	0.058 (2)	−0.004 (2)	−0.0152 (18)	−0.004 (2)
C8	0.037 (2)	0.078 (3)	0.062 (2)	0.0016 (18)	−0.0036 (18)	−0.0031 (19)
C9	0.0379 (18)	0.056 (2)	0.0385 (17)	0.0073 (15)	0.0027 (14)	−0.0009 (14)
C10	0.0383 (18)	0.0291 (16)	0.0351 (14)	0.0061 (13)	−0.0025 (13)	−0.0009 (13)
C11	0.0368 (16)	0.033 (2)	0.0311 (15)	0.0008 (14)	−0.0009 (14)	−0.0039 (13)
C12	0.062 (3)	0.060 (3)	0.0266 (16)	−0.0001 (17)	0.0010 (14)	0.0023 (17)
C13	0.056 (3)	0.033 (3)	0.0313 (17)	0.0009 (14)	0.0001 (13)	−0.0018 (17)
C14	0.075 (3)	0.037 (2)	0.0390 (17)	−0.0046 (17)	−0.0107 (17)	−0.0045 (15)
C15	0.057 (2)	0.048 (2)	0.0427 (17)	−0.0082 (18)	−0.0138 (16)	−0.0015 (16)
C16	0.068 (3)	0.045 (2)	0.070 (2)	0.012 (2)	0.006 (2)	−0.015 (2)
C17	0.064 (3)	0.087 (3)	0.096 (3)	−0.015 (2)	−0.030 (2)	−0.010 (3)
N3	0.0368 (16)	0.0427 (18)	0.0285 (12)	0.0010 (13)	−0.0040 (11)	−0.0052 (12)
N4	0.0503 (17)	0.0440 (17)	0.0436 (14)	−0.0010 (14)	−0.0040 (13)	−0.0080 (13)
C18	0.0270 (16)	0.0435 (18)	0.0318 (14)	0.0036 (16)	−0.0051 (13)	−0.0027 (15)
C19	0.0300 (17)	0.047 (2)	0.0331 (15)	−0.0040 (14)	0.0006 (13)	−0.0045 (14)
C20	0.0360 (18)	0.050 (2)	0.0389 (16)	−0.0065 (15)	0.0067 (14)	0.0022 (15)
C21	0.036 (2)	0.057 (2)	0.0302 (16)	−0.0007 (15)	0.0049 (15)	−0.0022 (15)
C22	0.0369 (18)	0.046 (2)	0.0367 (15)	0.0047 (15)	−0.0012 (14)	−0.0081 (15)
C23	0.075 (3)	0.062 (3)	0.0420 (18)	0.005 (2)	−0.0013 (17)	−0.0179 (18)
C24	0.104 (3)	0.041 (2)	0.064 (3)	0.008 (2)	−0.009 (2)	−0.0211 (19)
C25	0.099 (3)	0.035 (2)	0.065 (3)	0.006 (2)	−0.011 (2)	−0.0037 (19)
C26	0.064 (2)	0.041 (2)	0.0424 (17)	0.0066 (17)	−0.0058 (16)	−0.0009 (15)
C27	0.0314 (16)	0.0390 (18)	0.0364 (15)	0.0048 (14)	0.0002 (12)	−0.0046 (14)
C28	0.0345 (19)	0.0398 (18)	0.0252 (14)	0.0005 (14)	−0.0011 (13)	−0.0018 (13)
C29	0.054 (3)	0.062 (3)	0.0338 (17)	−0.0054 (18)	0.0063 (17)	−0.0003 (15)
C30	0.034 (2)	0.055 (3)	0.0323 (18)	0.0017 (14)	−0.0007 (17)	−0.0005 (13)
C31	0.037 (2)	0.075 (3)	0.049 (2)	−0.0038 (18)	−0.0080 (16)	−0.0122 (19)
C32	0.050 (2)	0.060 (2)	0.0509 (19)	−0.0101 (19)	−0.0029 (17)	−0.0152 (18)
C33	0.039 (2)	0.066 (3)	0.063 (2)	0.0115 (19)	−0.0082 (17)	0.003 (2)
C34	0.093 (4)	0.068 (3)	0.120 (4)	−0.019 (3)	−0.013 (3)	−0.033 (3)

Geometric parameters (Å, º)

N1—C13	1.352 (4)	C17—H17C	0.9600
N1—N2	1.364 (4)	N3—C30	1.361 (4)
N1—C11	1.462 (4)	N3—N4	1.368 (4)
N2—C15	1.333 (4)	N4—C32	1.332 (4)
N3—C28	1.457 (4)	C18—C19	1.357 (4)
C1—C2	1.365 (4)	C18—C27	1.429 (4)
C1—C10	1.420 (4)	C18—C28	1.517 (4)
C1—C11	1.526 (4)	C19—C20	1.412 (4)
C2—C3	1.403 (4)	C19—H19	0.9300
C2—H2	0.9300	C20—C21	1.363 (5)
C3—C4	1.363 (5)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.429 (5)
C4—C5	1.425 (5)	C21—C29	1.507 (4)
C4—C12	1.515 (4)	C22—C23	1.412 (5)
C5—C6	1.414 (4)	C22—C27	1.421 (4)
C5—C10	1.424 (4)	C23—C24	1.358 (6)
C6—C7	1.348 (5)	C23—H23	0.9300
C6—H6	0.9300	C24—C25	1.383 (5)
C7—C8	1.392 (5)	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.362 (5)
C8—C9	1.353 (5)	C25—H25	0.9300
C8—H8	0.9300	C26—C27	1.417 (5)
C9—C10	1.416 (4)	C26—H26	0.9300
C9—H9	0.9300	C28—C28^ii	1.578 (6)
C11—C11^i	1.582 (6)	C28—H28	0.9800
C11—H11	0.9800	C29—C29^ii	1.586 (8)
C12—C12^i	1.565 (8)	C29—H29A	0.9700
C12—H12A	0.9700	C29—H29B	0.9700
C12—H12B	0.9700	C30—C31	1.366 (5)
C13—C14	1.361 (5)	C30—C33	1.475 (5)
C13—C16	1.491 (5)	C31—C32	1.391 (5)
C14—C15	1.387 (5)	C31—H31	0.9300
C14—H14	0.9300	C32—C34	1.487 (6)
C15—C17	1.496 (5)	C33—H33A	0.9600
C16—H16A	0.9600	C33—H33B	0.9600
C16—H16B	0.9600	C33—H33C	0.9600
C16—H16C	0.9600	C34—H34A	0.9600
C17—H17A	0.9600	C34—H34B	0.9600
C17—H17B	0.9600	C34—H34C	0.9600
C13—N1—N2	111.7 (2)	C30—N3—N4	111.6 (2)
C13—N1—C11	125.4 (3)	C30—N3—C28	125.4 (3)
N2—N1—C11	121.2 (2)	N4—N3—C28	121.4 (2)
C15—N2—N1	104.4 (3)	C32—N4—N3	104.8 (3)
C2—C1—C10	118.5 (3)	C19—C18—C27	118.4 (3)
C1—C2—C3	120.8 (3)	C27—C18—C28	120.8 (3)
C1—C11—C11^i	111.83 (17)	C18—C19—C20	121.0 (3)
C2—C1—C11	119.8 (3)	C18—C28—C28^ii	111.67 (17)
C1—C2—H2	119.6	C18—C19—H19	119.5
C3—C2—H2	119.6	C19—C18—C28	119.8 (3)
C3—C4—C12	119.6 (3)	C20—C19—H19	119.5
C4—C3—C2	121.3 (3)	C21—C20—H20	119.4
C4—C12—C12^i	111.7 (2)	C19—C20—H20	119.4
C10—C1—C11	120.6 (3)	C20—C21—C22	117.8 (3)
C4—C3—H3	119.3	C20—C21—C29	120.0 (3)
C2—C3—H3	119.3	C21—C20—C19	121.2 (3)
C3—C4—C5	117.8 (3)	C22—C21—C29	120.8 (3)
C5—C4—C12	121.1 (3)	C23—C22—C27	118.8 (3)
C6—C5—C10	118.5 (3)	C23—C22—C21	121.6 (3)
C6—C5—C4	121.8 (3)	C27—C22—C21	119.3 (3)
C10—C5—C4	119.5 (3)	C24—C23—C22	121.3 (3)
C7—C6—C5	121.4 (3)	C24—C23—H23	119.3
C7—C6—H6	119.3	C22—C23—H23	119.3
C5—C6—H6	119.3	C23—C24—C25	120.1 (3)
C6—C7—C8	120.5 (3)	C23—C24—H24	119.9
C6—C7—H7	119.7	C25—C24—H24	119.9
C8—C7—H7	119.7	C26—C25—C24	120.7 (4)
C9—C8—C7	120.1 (3)	C26—C25—H25	119.6
C9—C8—H8	119.9	C24—C25—H25	119.6
C7—C8—H8	119.9	C25—C26—C27	121.3 (3)
C8—C9—C10	121.8 (3)	C25—C26—H26	119.4
C8—C9—H9	119.1	C27—C26—H26	119.4
C10—C9—H9	119.1	C26—C27—C22	117.8 (3)
C9—C10—C1	123.3 (3)	C26—C27—C18	123.1 (3)
C9—C10—C5	117.6 (3)	C22—C27—C18	119.1 (3)
C1—C10—C5	118.9 (3)	N3—C28—C18	111.8 (3)
N1—C11—C1	111.9 (3)	N3—C28—C28^ii	110.7 (3)
N1—C11—C11^i	110.3 (3)	N3—C28—H28	107.5
N1—C11—H11	107.5	C18—C28—H28	107.5
C1—C11—H11	107.5	C28^ii—C28—H28	107.5
C11^i—C11—H11	107.5	C21—C29—C29^ii	111.4 (2)
C4—C12—H12A	109.3	C21—C29—H29A	109.4
C12^i—C12—H12A	109.3	C29^ii—C29—H29A	109.4
C4—C12—H12B	109.3	C21—C29—H29B	109.4
C12^i—C12—H12B	109.3	C29^ii—C29—H29B	109.4
H12A—C12—H12B	107.9	H29A—C29—H29B	108.0
N1—C13—C14	106.5 (3)	N3—C30—C31	106.0 (3)
N1—C13—C16	122.3 (3)	N3—C30—C33	122.8 (3)
C14—C13—C16	131.2 (4)	C31—C30—C33	131.1 (4)
C13—C14—C15	106.1 (3)	C30—C31—C32	106.6 (3)
C13—C14—H14	126.9	C30—C31—H31	126.7
C15—C14—H14	126.9	C32—C31—H31	126.7
N2—C15—C14	111.2 (3)	N4—C32—C31	110.9 (3)
N2—C15—C17	120.6 (3)	N4—C32—C34	120.3 (4)
C14—C15—C17	128.2 (3)	C31—C32—C34	128.8 (4)
C13—C16—H16A	109.5	C30—C33—H33A	109.5
C13—C16—H16B	109.5	C30—C33—H33B	109.5
H16A—C16—H16B	109.5	H33A—C33—H33B	109.5
C13—C16—H16C	109.5	C30—C33—H33C	109.5
H16A—C16—H16C	109.5	H33A—C33—H33C	109.5
H16B—C16—H16C	109.5	H33B—C33—H33C	109.5
C15—C17—H17A	109.5	C32—C34—H34A	109.5
C15—C17—H17B	109.5	C32—C34—H34B	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
C15—C17—H17C	109.5	C32—C34—H34C	109.5
H17A—C17—H17C	109.5	H34A—C34—H34C	109.5
H17B—C17—H17C	109.5	H34B—C34—H34C	109.5
C13—N1—N2—C15	1.6 (3)	C30—N3—N4—C32	2.1 (3)
C11—N1—N2—C15	167.6 (3)	C28—N3—N4—C32	168.8 (3)
C1—C2—C3—C4	−0.2 (5)	C18—C19—C20—C21	1.6 (5)
C2—C1—C11—C11^i	−75.6 (4)	C19—C18—C28—C28^ii	−74.5 (4)
C2—C3—C4—C5	14.7 (5)	C19—C20—C21—C22	14.2 (5)
C2—C3—C4—C12	−151.3 (3)	C19—C20—C21—C29	−152.2 (3)
C3—C4—C12—C12^i	102.0 (4)	C20—C21—C29—C29^ii	101.9 (5)
C10—C1—C2—C3	−14.0 (5)	C27—C18—C19—C20	−15.2 (4)
C11—C1—C2—C3	154.3 (3)	C28—C18—C19—C20	153.5 (3)
C3—C4—C5—C6	170.3 (3)	C20—C21—C22—C23	170.1 (3)
C12—C4—C5—C6	−24.0 (5)	C29—C21—C22—C23	−23.6 (5)
C3—C4—C5—C10	−14.9 (5)	C20—C21—C22—C27	−16.2 (5)
C12—C4—C5—C10	150.8 (3)	C29—C21—C22—C27	150.1 (3)
C10—C5—C6—C7	−0.4 (5)	C27—C22—C23—C24	−0.1 (5)
C4—C5—C6—C7	174.5 (4)	C21—C22—C23—C24	173.6 (4)
C5—C6—C7—C8	0.2 (6)	C22—C23—C24—C25	−1.2 (6)
C6—C7—C8—C9	−0.2 (6)	C23—C24—C25—C26	1.6 (6)
C7—C8—C9—C10	0.5 (6)	C24—C25—C26—C27	−0.7 (6)
C8—C9—C10—C1	−176.0 (3)	C25—C26—C27—C22	−0.6 (5)
C8—C9—C10—C5	−0.7 (5)	C25—C26—C27—C18	−176.3 (3)
C2—C1—C10—C9	−171.6 (3)	C23—C22—C27—C26	0.9 (4)
C11—C1—C10—C9	20.2 (5)	C21—C22—C27—C26	−172.9 (3)
C2—C1—C10—C5	13.2 (4)	C23—C22—C27—C18	176.9 (3)
C11—C1—C10—C5	−155.0 (3)	C21—C22—C27—C18	3.1 (4)
C6—C5—C10—C9	0.7 (4)	C19—C18—C27—C26	−171.7 (3)
C4—C5—C10—C9	−174.3 (3)	C28—C18—C27—C26	19.7 (5)
C6—C5—C10—C1	176.2 (3)	C19—C18—C27—C22	12.6 (4)
C4—C5—C10—C1	1.2 (4)	C28—C18—C27—C22	−156.0 (3)
C13—N1—C11—C1	78.4 (4)	C30—N3—C28—C18	78.3 (4)
N2—N1—C11—C1	−85.6 (3)	N4—N3—C28—C18	−86.5 (3)
C13—N1—C11—C11^i	−156.4 (3)	C30—N3—C28—C28^ii	−156.5 (3)
N2—N1—C11—C11^i	39.6 (4)	N4—N3—C28—C28^ii	38.7 (4)
C2—C1—C11—N1	48.8 (4)	C19—C18—C28—N3	50.1 (4)
C10—C1—C11—N1	−143.2 (3)	C27—C18—C28—N3	−141.5 (3)
C10—C1—C11—C11^i	92.5 (4)	C27—C18—C28—C28^ii	93.9 (4)
C5—C4—C12—C12^i	−63.5 (5)	C22—C21—C29—C29^ii	−64.1 (5)
N2—N1—C13—C14	−1.7 (4)	N4—N3—C30—C31	−2.3 (4)
C11—N1—C13—C14	−167.0 (3)	C28—N3—C30—C31	−168.4 (3)
N2—N1—C13—C16	177.9 (3)	N4—N3—C30—C33	175.5 (3)
C11—N1—C13—C16	12.6 (5)	C28—N3—C30—C33	9.5 (5)
N1—C13—C14—C15	1.0 (4)	N3—C30—C31—C32	1.6 (4)
C16—C13—C14—C15	−178.5 (4)	C33—C30—C31—C32	−176.0 (4)
N1—N2—C15—C14	−0.9 (4)	N3—N4—C32—C31	−1.0 (4)
N1—N2—C15—C17	178.6 (3)	N3—N4—C32—C34	179.4 (3)
C13—C14—C15—N2	−0.1 (4)	C30—C31—C32—N4	−0.4 (4)
C13—C14—C15—C17	−179.5 (4)	C30—C31—C32—C34	179.1 (4)

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