A tetrakis­(secondary amide) derivative of quadricyclane: 3-iso­propyl­idene-tetra­cyclo­[3.2.0.0^2,7.0^4,6]­heptane-1,5,6,7-tetra­carboxyl­ic acid tetrakis(tert-butyl­amide)

The molecule of the title compound, C₃₀H₄₈N₄O₄, displays approximate twofold symmetry. The four amide groups are arranged such that four intramolecular N—H...O hydrogen bonds are formed.

Key indicators

• Single-crystal X-ray study
• T = 143 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.103
• Data-to-parameter ratio = 17.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_320  Alert C Check Hybridisation of  C5     in Main Residue .          ?

PLAT_320  Alert C Check Hybridisation of  C7     in Main Residue .          ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

3-Isopropylidene-tetracyclo[3.2.0.0^2,7.0^4,5]heptane- 1,5,6,7-tetracarboxylic acid tetrakis(tert-butylamide)

Crystal data

C30H48N4O4	Z = 2
Mr = 528.72	F(000) = 576
Triclinic, P1	Dx = 1.127 Mg m^−3
a = 9.9831 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2324 (10) Å	Cell parameters from 5756 reflections
c = 13.9644 (10) Å	θ = 2–28°
α = 92.574 (3)°	µ = 0.08 mm^−1
β = 106.831 (3)°	T = 143 K
γ = 105.554 (3)°	Prism, colourless
V = 1558.5 (2) Å^3	0.40 × 0.29 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer	4684 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 26.4°, θmin = 1.5°
Detector resolution: 8.192 pixels mm^-1	h = −12→12
ω–scan	k = −15→15
14409 measured reflections	l = −17→17
6352 independent reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.2051P] where P = (Fo^2 + 2Fc^2)/3
6352 reflections	(Δ/σ)max < 0.001
373 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.18 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	0.60747 (11)	0.47639 (8)	0.64218 (8)	0.0417 (3)
O2	0.43366 (10)	0.10456 (7)	0.70203 (7)	0.0356 (2)
O3	0.17048 (11)	0.23915 (8)	0.87880 (7)	0.0347 (2)
O4	0.28301 (11)	0.59070 (7)	0.77216 (7)	0.0351 (2)
N1	0.49918 (15)	0.60357 (9)	0.68437 (9)	0.0370 (3)
H01	0.4307 (18)	0.6122 (13)	0.7077 (12)	0.045 (5)*
N2	0.60441 (12)	0.26198 (10)	0.68533 (8)	0.0309 (3)
H02	0.6165 (16)	0.3373 (14)	0.6724 (11)	0.042 (4)*
N3	0.25743 (12)	0.10357 (9)	0.82410 (9)	0.0295 (3)
H03	0.3045 (17)	0.0890 (12)	0.7853 (11)	0.036 (4)*
N4	0.26571 (12)	0.47241 (9)	0.89138 (8)	0.0261 (2)
H04	0.2378 (15)	0.3975 (13)	0.8985 (11)	0.034 (4)*
C1	0.37739 (14)	0.40315 (10)	0.66910 (9)	0.0259 (3)
C2	0.21965 (14)	0.40172 (11)	0.61595 (9)	0.0269 (3)
H2	0.1981	0.4715	0.5886	0.032*
C3	0.13231 (14)	0.28643 (11)	0.56195 (9)	0.0268 (3)
C4	0.20270 (13)	0.21392 (11)	0.62881 (9)	0.0256 (3)
H4	0.1666	0.1286	0.6122	0.031*
C5	0.36551 (13)	0.27441 (10)	0.67752 (9)	0.0250 (3)
C6	0.25752 (13)	0.26996 (10)	0.73879 (9)	0.0241 (3)
C7	0.26756 (13)	0.39779 (10)	0.72941 (9)	0.0245 (3)
C8	0.02138 (15)	0.25601 (12)	0.47614 (10)	0.0336 (3)
C9	−0.05601 (18)	0.13288 (13)	0.43273 (11)	0.0448 (4)
H9A	−0.0320	0.1157	0.3716	0.054*
H9B	−0.1620	0.1192	0.4159	0.054*
H9C	−0.0245	0.0834	0.4824	0.054*
C10	−0.03578 (19)	0.34118 (14)	0.41501 (12)	0.0501 (4)
H10A	0.0248	0.4189	0.4459	0.060*
H10B	−0.1371	0.3320	0.4131	0.060*
H10C	−0.0324	0.3282	0.3461	0.060*
C11	0.50598 (15)	0.49833 (11)	0.66517 (9)	0.0299 (3)
C12	0.60886 (19)	0.71080 (12)	0.68096 (11)	0.0453 (4)
C13	0.7567 (2)	0.71772 (17)	0.75515 (17)	0.0929 (9)
H13A	0.7502	0.7201	0.8239	0.112*
H13B	0.8297	0.7872	0.7502	0.112*
H13C	0.7857	0.6503	0.7393	0.112*
C14	0.6179 (2)	0.71641 (14)	0.57472 (13)	0.0539 (5)
H14A	0.6548	0.6547	0.5561	0.065*
H14B	0.6845	0.7905	0.5718	0.065*
H14C	0.5203	0.7077	0.5276	0.065*
C15	0.5523 (3)	0.80717 (14)	0.71019 (15)	0.0763 (7)
H15A	0.4612	0.8052	0.6580	0.092*
H15B	0.6257	0.8810	0.7165	0.092*
H15C	0.5335	0.7974	0.7749	0.092*
C16	0.47254 (14)	0.20635 (11)	0.68937 (9)	0.0275 (3)
C17	0.72657 (15)	0.21211 (13)	0.69405 (11)	0.0380 (3)
C18	0.85528 (18)	0.31059 (16)	0.68948 (16)	0.0623 (5)
H18A	0.8279	0.3419	0.6257	0.075*
H18B	0.9396	0.2824	0.6937	0.075*
H18C	0.8810	0.3707	0.7461	0.075*
C19	0.6843 (2)	0.11741 (15)	0.60645 (13)	0.0530 (4)
H19A	0.5974	0.0574	0.6077	0.064*
H19B	0.7655	0.0848	0.6129	0.064*
H19C	0.6628	0.1493	0.5425	0.064*
C20	0.76546 (18)	0.16537 (16)	0.79443 (12)	0.0522 (4)
H20A	0.7890	0.2264	0.8498	0.063*
H20B	0.8504	0.1371	0.8013	0.063*
H20C	0.6820	0.1025	0.7967	0.063*
C21	0.22703 (13)	0.20304 (10)	0.82121 (9)	0.0250 (3)
C22	0.22689 (15)	0.02095 (11)	0.89486 (10)	0.0327 (3)
C23	0.3111 (2)	0.07463 (14)	1.00274 (12)	0.0579 (5)
H23A	0.4162	0.0989	1.0113	0.069*
H23B	0.2911	0.0185	1.0486	0.069*
H23C	0.2805	0.1413	1.0183	0.069*
C24	0.06388 (17)	−0.01849 (14)	0.88008 (14)	0.0526 (4)
H24A	0.0337	0.0453	0.9029	0.063*
H24B	0.0423	−0.0815	0.9194	0.063*
H24C	0.0102	−0.0447	0.8084	0.063*
C25	0.2765 (2)	−0.08014 (14)	0.86738 (14)	0.0584 (5)
H25A	0.2157	−0.1174	0.7992	0.070*
H25B	0.2665	−0.1351	0.9157	0.070*
H25C	0.3792	−0.0529	0.8696	0.070*
C26	0.27135 (13)	0.49490 (10)	0.80019 (9)	0.0258 (3)
C27	0.26760 (14)	0.55655 (11)	0.97165 (10)	0.0293 (3)
C28	0.40649 (15)	0.65728 (12)	0.99792 (11)	0.0386 (3)
H28A	0.4924	0.6291	1.0182	0.046*
H28B	0.4088	0.7102	1.0536	0.046*
H28C	0.4076	0.6973	0.9388	0.046*
C29	0.26686 (18)	0.49287 (13)	1.06292 (11)	0.0411 (4)
H29A	0.1808	0.4253	1.0446	0.049*
H29B	0.2634	0.5435	1.1180	0.049*
H29C	0.3559	0.4689	1.0849	0.049*
C30	0.13083 (15)	0.59655 (13)	0.93642 (11)	0.0369 (3)
H30A	0.1324	0.6359	0.8770	0.044*
H30B	0.1291	0.6493	0.9907	0.044*
H30C	0.0433	0.5302	0.9190	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0352 (6)	0.0344 (6)	0.0560 (7)	0.0060 (4)	0.0180 (5)	0.0118 (5)
O2	0.0387 (5)	0.0269 (5)	0.0475 (6)	0.0150 (4)	0.0172 (5)	0.0105 (4)
O3	0.0436 (6)	0.0286 (5)	0.0371 (5)	0.0105 (4)	0.0202 (5)	0.0080 (4)
O4	0.0531 (6)	0.0251 (5)	0.0318 (5)	0.0170 (4)	0.0146 (5)	0.0076 (4)
N1	0.0546 (8)	0.0225 (6)	0.0326 (7)	0.0023 (6)	0.0199 (6)	0.0048 (5)
N2	0.0299 (6)	0.0304 (6)	0.0344 (6)	0.0116 (5)	0.0102 (5)	0.0060 (5)
N3	0.0331 (6)	0.0264 (6)	0.0310 (6)	0.0105 (5)	0.0106 (5)	0.0103 (5)
N4	0.0310 (6)	0.0225 (6)	0.0247 (6)	0.0091 (5)	0.0075 (5)	0.0033 (4)
C1	0.0303 (7)	0.0228 (6)	0.0230 (6)	0.0074 (5)	0.0064 (5)	0.0040 (5)
C2	0.0336 (7)	0.0240 (6)	0.0230 (6)	0.0116 (5)	0.0055 (5)	0.0063 (5)
C3	0.0307 (7)	0.0250 (6)	0.0252 (7)	0.0106 (5)	0.0073 (5)	0.0038 (5)
C4	0.0271 (7)	0.0221 (6)	0.0252 (7)	0.0069 (5)	0.0050 (5)	0.0028 (5)
C5	0.0271 (7)	0.0219 (6)	0.0248 (6)	0.0072 (5)	0.0063 (5)	0.0041 (5)
C6	0.0238 (6)	0.0225 (6)	0.0244 (6)	0.0072 (5)	0.0045 (5)	0.0040 (5)
C7	0.0282 (7)	0.0226 (6)	0.0226 (6)	0.0088 (5)	0.0058 (5)	0.0058 (5)
C8	0.0370 (8)	0.0338 (7)	0.0275 (7)	0.0141 (6)	0.0035 (6)	0.0013 (6)
C9	0.0465 (9)	0.0399 (9)	0.0350 (8)	0.0122 (7)	−0.0049 (7)	−0.0032 (7)
C10	0.0621 (11)	0.0454 (9)	0.0338 (8)	0.0252 (8)	−0.0070 (8)	0.0036 (7)
C11	0.0343 (7)	0.0275 (7)	0.0217 (6)	0.0039 (6)	0.0043 (6)	0.0046 (5)
C12	0.0654 (11)	0.0246 (7)	0.0311 (8)	−0.0067 (7)	0.0110 (7)	0.0054 (6)
C13	0.0863 (16)	0.0510 (12)	0.0777 (15)	−0.0306 (11)	−0.0245 (12)	0.0175 (11)
C14	0.0733 (12)	0.0411 (9)	0.0480 (10)	0.0039 (8)	0.0307 (9)	0.0146 (8)
C15	0.142 (2)	0.0254 (9)	0.0626 (12)	0.0041 (10)	0.0536 (13)	0.0041 (8)
C16	0.0307 (7)	0.0288 (7)	0.0231 (6)	0.0115 (6)	0.0062 (5)	0.0024 (5)
C17	0.0333 (8)	0.0446 (8)	0.0429 (8)	0.0199 (7)	0.0143 (6)	0.0065 (7)
C18	0.0376 (9)	0.0656 (12)	0.0920 (15)	0.0187 (9)	0.0291 (10)	0.0156 (11)
C19	0.0644 (11)	0.0609 (11)	0.0494 (10)	0.0344 (9)	0.0266 (9)	0.0074 (8)
C20	0.0470 (10)	0.0731 (12)	0.0449 (9)	0.0371 (9)	0.0083 (8)	0.0122 (9)
C21	0.0219 (6)	0.0230 (6)	0.0247 (6)	0.0034 (5)	0.0021 (5)	0.0035 (5)
C22	0.0368 (8)	0.0244 (7)	0.0318 (7)	0.0047 (6)	0.0058 (6)	0.0119 (6)
C23	0.0730 (12)	0.0404 (9)	0.0361 (9)	−0.0009 (8)	−0.0049 (8)	0.0175 (7)
C24	0.0439 (9)	0.0422 (9)	0.0619 (11)	−0.0021 (7)	0.0137 (8)	0.0201 (8)
C25	0.0827 (13)	0.0401 (9)	0.0656 (12)	0.0313 (9)	0.0276 (10)	0.0275 (9)
C26	0.0261 (6)	0.0252 (7)	0.0256 (7)	0.0101 (5)	0.0048 (5)	0.0036 (5)
C27	0.0324 (7)	0.0299 (7)	0.0259 (7)	0.0110 (6)	0.0086 (6)	0.0002 (5)
C28	0.0351 (8)	0.0368 (8)	0.0374 (8)	0.0071 (6)	0.0069 (6)	−0.0078 (6)
C29	0.0519 (9)	0.0474 (9)	0.0293 (8)	0.0199 (7)	0.0157 (7)	0.0053 (7)
C30	0.0359 (8)	0.0402 (8)	0.0377 (8)	0.0162 (6)	0.0124 (6)	0.0005 (6)

Geometric parameters (Å, º)

O1—C11	1.2362 (16)	C13—H13B	0.9800
O2—C16	1.2379 (15)	C13—H13C	0.9800
O3—C21	1.2350 (15)	C14—H14A	0.9800
O4—C26	1.2387 (15)	C14—H14B	0.9800
N1—C11	1.3267 (18)	C14—H14C	0.9800
N1—C12	1.4789 (18)	C15—H15A	0.9800
N1—H01	0.866 (16)	C15—H15B	0.9800
N2—C16	1.3287 (17)	C15—H15C	0.9800
N2—C17	1.4811 (17)	C17—C20	1.523 (2)
N2—H02	0.930 (16)	C17—C19	1.526 (2)
N3—C21	1.3302 (16)	C17—C18	1.527 (2)
N3—C22	1.4799 (16)	C18—H18A	0.9800
N3—H03	0.854 (16)	C18—H18B	0.9800
N4—C26	1.3285 (16)	C18—H18C	0.9800
N4—C27	1.4799 (16)	C19—H19A	0.9800
N4—H04	0.903 (15)	C19—H19B	0.9800
C1—C11	1.5005 (18)	C19—H19C	0.9800
C1—C2	1.5291 (18)	C20—H20A	0.9800
C1—C7	1.5546 (18)	C20—H20B	0.9800
C1—C5	1.5597 (16)	C20—H20C	0.9800
C2—C3	1.4772 (18)	C22—C23	1.513 (2)
C2—C7	1.5237 (17)	C22—C24	1.516 (2)
C2—H2	1.0000	C22—C25	1.522 (2)
C3—C8	1.3309 (18)	C23—H23A	0.9800
C3—C4	1.4767 (17)	C23—H23B	0.9800
C4—C5	1.5237 (17)	C23—H23C	0.9800
C4—C6	1.5316 (17)	C24—H24A	0.9800
C4—H4	1.0000	C24—H24B	0.9800
C5—C16	1.4998 (17)	C24—H24C	0.9800
C5—C6	1.5505 (17)	C25—H25A	0.9800
C6—C21	1.4971 (17)	C25—H25B	0.9800
C6—C7	1.5537 (16)	C25—H25C	0.9800
C7—C26	1.4961 (17)	C27—C29	1.5241 (19)
C8—C9	1.502 (2)	C27—C28	1.5245 (19)
C8—C10	1.5021 (19)	C27—C30	1.5285 (19)
C9—H9A	0.9800	C28—H28A	0.9800
C9—H9B	0.9800	C28—H28B	0.9800
C9—H9C	0.9800	C28—H28C	0.9800
C10—H10A	0.9800	C29—H29A	0.9800
C10—H10B	0.9800	C29—H29B	0.9800
C10—H10C	0.9800	C29—H29C	0.9800
C12—C14	1.516 (2)	C30—H30A	0.9800
C12—C13	1.516 (3)	C30—H30B	0.9800
C12—C15	1.524 (2)	C30—H30C	0.9800
C13—H13A	0.9800
C11—N1—C12	125.83 (14)	C12—C15—H15A	109.5
C11—N1—H01	118.4 (11)	C12—C15—H15B	109.5
C12—N1—H01	115.3 (11)	H15A—C15—H15B	109.5
C16—N2—C17	125.57 (12)	C12—C15—H15C	109.5
C16—N2—H02	115.3 (9)	H15A—C15—H15C	109.5
C17—N2—H02	119.1 (9)	H15B—C15—H15C	109.5
C21—N3—C22	125.12 (12)	O2—C16—N2	124.86 (12)
C21—N3—H03	117.1 (10)	O2—C16—C5	119.03 (11)
C22—N3—H03	117.6 (10)	N2—C16—C5	116.11 (11)
C26—N4—C27	124.96 (11)	N2—C17—C20	110.13 (12)
C26—N4—H04	115.6 (9)	N2—C17—C19	109.98 (12)
C27—N4—H04	117.9 (9)	C20—C17—C19	110.40 (13)
C11—C1—C2	121.94 (11)	N2—C17—C18	105.64 (12)
C11—C1—C7	131.31 (11)	C20—C17—C18	110.12 (14)
C2—C1—C7	59.22 (8)	C19—C17—C18	110.46 (14)
C11—C1—C5	128.87 (11)	C17—C18—H18A	109.5
C2—C1—C5	103.65 (10)	C17—C18—H18B	109.5
C7—C1—C5	90.15 (9)	H18A—C18—H18B	109.5
C3—C2—C7	110.03 (10)	C17—C18—H18C	109.5
C3—C2—C1	110.17 (10)	H18A—C18—H18C	109.5
C7—C2—C1	61.23 (8)	H18B—C18—H18C	109.5
C3—C2—H2	120.4	C17—C19—H19A	109.5
C7—C2—H2	120.4	C17—C19—H19B	109.5
C1—C2—H2	120.4	H19A—C19—H19B	109.5
C8—C3—C4	129.46 (12)	C17—C19—H19C	109.5
C8—C3—C2	129.68 (12)	H19A—C19—H19C	109.5
C4—C3—C2	100.86 (10)	H19B—C19—H19C	109.5
C3—C4—C5	110.45 (10)	C17—C20—H20A	109.5
C3—C4—C6	110.26 (10)	C17—C20—H20B	109.5
C5—C4—C6	60.99 (8)	H20A—C20—H20B	109.5
C3—C4—H4	120.3	C17—C20—H20C	109.5
C5—C4—H4	120.3	H20A—C20—H20C	109.5
C6—C4—H4	120.3	H20B—C20—H20C	109.5
C16—C5—C4	119.22 (10)	O3—C21—N3	123.94 (12)
C16—C5—C6	126.12 (10)	O3—C21—C6	119.61 (11)
C4—C5—C6	59.76 (8)	N3—C21—C6	116.36 (11)
C16—C5—C1	133.63 (11)	N3—C22—C23	110.44 (11)
C4—C5—C1	103.53 (10)	N3—C22—C24	109.76 (11)
C6—C5—C1	89.62 (9)	C23—C22—C24	110.46 (14)
C21—C6—C4	121.26 (10)	N3—C22—C25	105.83 (12)
C21—C6—C5	133.07 (10)	C23—C22—C25	110.59 (13)
C4—C6—C5	59.25 (8)	C24—C22—C25	109.66 (13)
C21—C6—C7	128.32 (11)	C22—C23—H23A	109.5
C4—C6—C7	103.36 (9)	C22—C23—H23B	109.5
C5—C6—C7	90.53 (9)	H23A—C23—H23B	109.5
C26—C7—C2	119.96 (10)	C22—C23—H23C	109.5
C26—C7—C6	133.30 (11)	H23A—C23—H23C	109.5
C2—C7—C6	104.02 (10)	H23B—C23—H23C	109.5
C26—C7—C1	124.74 (11)	C22—C24—H24A	109.5
C2—C7—C1	59.56 (8)	C22—C24—H24B	109.5
C6—C7—C1	89.69 (9)	H24A—C24—H24B	109.5
C3—C8—C9	122.18 (12)	C22—C24—H24C	109.5
C3—C8—C10	123.03 (13)	H24A—C24—H24C	109.5
C9—C8—C10	114.79 (12)	H24B—C24—H24C	109.5
C8—C9—H9A	109.5	C22—C25—H25A	109.5
C8—C9—H9B	109.5	C22—C25—H25B	109.5
H9A—C9—H9B	109.5	H25A—C25—H25B	109.5
C8—C9—H9C	109.5	C22—C25—H25C	109.5
H9A—C9—H9C	109.5	H25A—C25—H25C	109.5
H9B—C9—H9C	109.5	H25B—C25—H25C	109.5
C8—C10—H10A	109.5	O4—C26—N4	124.08 (12)
C8—C10—H10B	109.5	O4—C26—C7	119.07 (11)
H10A—C10—H10B	109.5	N4—C26—C7	116.82 (11)
C8—C10—H10C	109.5	N4—C27—C29	105.65 (11)
H10A—C10—H10C	109.5	N4—C27—C28	110.38 (11)
H10B—C10—H10C	109.5	C29—C27—C28	109.59 (12)
O1—C11—N1	124.05 (13)	N4—C27—C30	109.21 (11)
O1—C11—C1	120.21 (12)	C29—C27—C30	110.74 (12)
N1—C11—C1	115.71 (13)	C28—C27—C30	111.13 (11)
N1—C12—C14	110.00 (12)	C27—C28—H28A	109.5
N1—C12—C13	109.94 (13)	C27—C28—H28B	109.5
C14—C12—C13	110.85 (17)	H28A—C28—H28B	109.5
N1—C12—C15	105.49 (14)	C27—C28—H28C	109.5
C14—C12—C15	109.47 (13)	H28A—C28—H28C	109.5
C13—C12—C15	110.95 (16)	H28B—C28—H28C	109.5
C12—C13—H13A	109.5	C27—C29—H29A	109.5
C12—C13—H13B	109.5	C27—C29—H29B	109.5
H13A—C13—H13B	109.5	H29A—C29—H29B	109.5
C12—C13—H13C	109.5	C27—C29—H29C	109.5
H13A—C13—H13C	109.5	H29A—C29—H29C	109.5
H13B—C13—H13C	109.5	H29B—C29—H29C	109.5
C12—C14—H14A	109.5	C27—C30—H30A	109.5
C12—C14—H14B	109.5	C27—C30—H30B	109.5
H14A—C14—H14B	109.5	H30A—C30—H30B	109.5
C12—C14—H14C	109.5	C27—C30—H30C	109.5
H14A—C14—H14C	109.5	H30A—C30—H30C	109.5
H14B—C14—H14C	109.5	H30B—C30—H30C	109.5
C11—C1—C2—C3	135.33 (12)	C2—C1—C7—C26	−107.30 (13)
C7—C1—C2—C3	−102.39 (11)	C5—C1—C7—C26	146.85 (11)
C5—C1—C2—C3	−20.52 (13)	C11—C1—C7—C2	107.24 (15)
C11—C1—C2—C7	−122.28 (13)	C5—C1—C7—C2	−105.85 (10)
C5—C1—C2—C7	81.87 (10)	C11—C1—C7—C6	−146.25 (13)
C7—C2—C3—C8	147.41 (14)	C2—C1—C7—C6	106.51 (9)
C1—C2—C3—C8	−146.91 (14)	C5—C1—C7—C6	0.66 (9)
C7—C2—C3—C4	−33.09 (13)	C4—C3—C8—C9	1.3 (2)
C1—C2—C3—C4	32.58 (13)	C2—C3—C8—C9	−179.38 (14)
C8—C3—C4—C5	146.62 (14)	C4—C3—C8—C10	−178.44 (14)
C2—C3—C4—C5	−32.87 (13)	C2—C3—C8—C10	0.9 (2)
C8—C3—C4—C6	−147.83 (14)	C12—N1—C11—O1	0.5 (2)
C2—C3—C4—C6	32.67 (13)	C12—N1—C11—C1	−177.32 (12)
C3—C4—C5—C16	−140.42 (11)	C2—C1—C11—O1	−130.25 (13)
C6—C4—C5—C16	117.11 (12)	C7—C1—C11—O1	154.52 (13)
C3—C4—C5—C6	102.46 (11)	C5—C1—C11—O1	19.0 (2)
C3—C4—C5—C1	20.98 (13)	C2—C1—C11—N1	47.65 (17)
C6—C4—C5—C1	−81.48 (10)	C7—C1—C11—N1	−27.58 (19)
C11—C1—C5—C16	3.6 (2)	C5—C1—C11—N1	−163.06 (12)
C2—C1—C5—C16	157.16 (13)	C11—N1—C12—C14	62.8 (2)
C7—C1—C5—C16	−144.58 (14)	C11—N1—C12—C13	−59.5 (2)
C11—C1—C5—C4	−153.75 (12)	C11—N1—C12—C15	−179.19 (15)
C2—C1—C5—C4	−0.23 (12)	C17—N2—C16—O2	0.7 (2)
C7—C1—C5—C4	58.03 (10)	C17—N2—C16—C5	−179.33 (12)
C11—C1—C5—C6	147.56 (13)	C4—C5—C16—O2	−31.00 (17)
C2—C1—C5—C6	−58.92 (10)	C6—C5—C16—O2	41.16 (18)
C7—C1—C5—C6	−0.66 (9)	C1—C5—C16—O2	174.36 (12)
C3—C4—C6—C21	132.58 (12)	C4—C5—C16—N2	149.03 (11)
C5—C4—C6—C21	−124.64 (13)	C6—C5—C16—N2	−138.80 (12)
C3—C4—C6—C5	−102.78 (11)	C1—C5—C16—N2	−5.6 (2)
C3—C4—C6—C7	−20.27 (13)	C16—N2—C17—C20	−58.67 (18)
C5—C4—C6—C7	82.51 (9)	C16—N2—C17—C19	63.23 (18)
C16—C5—C6—C21	−0.2 (2)	C16—N2—C17—C18	−177.55 (14)
C4—C5—C6—C21	105.69 (15)	C22—N3—C21—O3	0.9 (2)
C1—C5—C6—C21	−148.37 (13)	C22—N3—C21—C6	−175.86 (11)
C16—C5—C6—C4	−105.91 (13)	C4—C6—C21—O3	−127.28 (13)
C1—C5—C6—C4	105.94 (9)	C5—C6—C21—O3	157.28 (13)
C16—C5—C6—C7	148.81 (12)	C7—C6—C21—O3	18.26 (19)
C4—C5—C6—C7	−105.28 (9)	C4—C6—C21—N3	49.60 (16)
C1—C5—C6—C7	0.66 (9)	C5—C6—C21—N3	−25.85 (19)
C3—C2—C7—C26	−142.28 (12)	C7—C6—C21—N3	−164.86 (11)
C1—C2—C7—C26	115.10 (13)	C21—N3—C22—C23	−61.86 (18)
C3—C2—C7—C6	21.43 (13)	C21—N3—C22—C24	60.16 (17)
C1—C2—C7—C6	−81.19 (10)	C21—N3—C22—C25	178.42 (13)
C3—C2—C7—C1	102.62 (11)	C27—N4—C26—O4	2.1 (2)
C21—C6—C7—C26	9.6 (2)	C27—N4—C26—C7	−179.76 (11)
C4—C6—C7—C26	159.82 (13)	C2—C7—C26—O4	−23.46 (18)
C5—C6—C7—C26	−141.74 (14)	C6—C7—C26—O4	178.49 (12)
C21—C6—C7—C2	−150.87 (12)	C1—C7—C26—O4	48.36 (17)
C4—C6—C7—C2	−0.68 (12)	C2—C7—C26—N4	158.29 (11)
C5—C6—C7—C2	57.76 (10)	C6—C7—C26—N4	0.2 (2)
C21—C6—C7—C1	150.71 (12)	C1—C7—C26—N4	−129.89 (13)
C4—C6—C7—C1	−59.11 (10)	C26—N4—C27—C29	−177.27 (12)
C5—C6—C7—C1	−0.66 (9)	C26—N4—C27—C28	−58.87 (16)
C11—C1—C7—C26	−0.1 (2)	C26—N4—C27—C30	63.58 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O4	0.866 (16)	1.906 (17)	2.7481 (17)	163.7 (15)
N2—H02···O1	0.930 (16)	1.790 (16)	2.7116 (15)	170.5 (14)
N3—H03···O2	0.854 (16)	1.951 (16)	2.7799 (16)	163.2 (14)
N4—H04···O3	0.903 (15)	1.851 (15)	2.7350 (14)	165.8 (13)