Crystal structure of r-1,c-2-dibenzoyl-t-3,t-4-bis­(2-nitro­phen­yl)cyclo­butane

The title mol­ecule is a tetra­substituted truxinic-type cyclo­butane derivative with a central ring that is almost planar despite of being placed in a general position. The mol­ecular structure of the dimer shows that the four benzene rings of the substituents are oriented in such a way that potential steric hindrance is minimized, whilst allowing some degree of inter­molecular π–π inter­actions for crystal stabilization.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.053
• wR factor = 0.164
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT213_ALERT_2_C Atom O2B             has ADP max/min Ratio .....        3.5 prolat
PLAT220_ALERT_2_C Non-Solvent Resd 1   O   Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N6 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        N12 Check
PLAT410_ALERT_2_C Short Intra H...H Contact   H3A    ..  H16A    .       1.95 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.624 Report
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..         5% Note
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C2      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C3      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         24 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

[3,4-Bis(2-nitrophenyl)cyclobutane-1,2-diyl]bis[(phenyl)methanone]

Crystal data

C30H22N2O6	F(000) = 528
Mr = 506.49	Dx = 1.341 Mg m^−3
Triclinic, P1	Melting point: 517 K
a = 7.2599 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5614 (5) Å	Cell parameters from 5272 reflections
c = 16.7351 (8) Å	θ = 3.6–27.9°
α = 78.863 (4)°	µ = 0.10 mm^−1
β = 87.472 (5)°	T = 295 K
γ = 85.238 (5)°	Prism, colourless
V = 1254.13 (13) Å^3	0.37 × 0.20 × 0.15 mm
Z = 2

Data collection

Agilent Xcalibur Atlas Gemini diffractometer	5116 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3292 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 10.5564 pixels mm^-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −9→8
Absorption correction: analytical (CrysAlis PRO; Agilent, 2013)	k = −13→13
Tmin = 0.962, Tmax = 0.983	l = −20→20
25649 measured reflections

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)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.0762P)^2 + 0.1873P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5116 reflections	Δρmax = 0.27 e Å^−3
363 parameters	Δρmin = −0.27 e Å^−3
24 restraints	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.011 (3)
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.6552 (3)	0.64030 (16)	0.23390 (11)	0.0415 (4)
H1A	0.548307	0.694892	0.209849	0.050*
C2	0.6594 (3)	0.63982 (16)	0.32828 (11)	0.0406 (4)
H2A	0.558141	0.699162	0.342918	0.049*
C3	0.8388 (3)	0.71065 (17)	0.31510 (11)	0.0415 (4)
H3A	0.942691	0.650434	0.336831	0.050*
C4	0.8326 (3)	0.71816 (17)	0.22142 (11)	0.0414 (4)
H4A	0.938656	0.668933	0.200920	0.050*
C5	0.6680 (3)	0.51217 (17)	0.20721 (11)	0.0466 (5)
C6	0.5325 (3)	0.4711 (2)	0.16339 (15)	0.0648 (6)
C7	0.5406 (5)	0.3472 (3)	0.1475 (2)	0.0961 (10)
H7A	0.447643	0.322545	0.118570	0.115*
C8	0.6849 (5)	0.2614 (3)	0.1744 (2)	0.0980 (10)
H8A	0.690019	0.177555	0.164369	0.118*
C9	0.8229 (5)	0.2982 (2)	0.21645 (17)	0.0815 (8)
H9A	0.922486	0.239823	0.234101	0.098*
C10	0.8140 (3)	0.4216 (2)	0.23247 (13)	0.0591 (6)
H10A	0.908604	0.445158	0.261050	0.071*
C11	0.6561 (3)	0.51184 (17)	0.38742 (11)	0.0424 (4)
C12	0.5073 (3)	0.43324 (18)	0.39869 (12)	0.0466 (5)
C13	0.5125 (3)	0.3138 (2)	0.45159 (13)	0.0564 (6)
H13A	0.410934	0.264323	0.456958	0.068*
C14	0.6658 (4)	0.2693 (2)	0.49537 (13)	0.0637 (6)
H14A	0.670172	0.189494	0.530677	0.076*
C15	0.8138 (3)	0.3437 (2)	0.48669 (14)	0.0646 (6)
H15A	0.919549	0.314127	0.516170	0.078*
C16	0.8071 (3)	0.4627 (2)	0.43438 (13)	0.0565 (6)
H16A	0.908810	0.511744	0.430641	0.068*
C17	0.8343 (3)	0.83090 (18)	0.35266 (11)	0.0449 (5)
C18	0.9976 (3)	0.91010 (17)	0.34225 (11)	0.0448 (5)
C19	0.9958 (3)	1.0116 (2)	0.38363 (15)	0.0633 (6)
H19A	0.892064	1.031224	0.414871	0.076*
C20	1.1465 (4)	1.0838 (3)	0.37887 (18)	0.0789 (8)
H20A	1.144193	1.151593	0.407100	0.095*
C21	1.3000 (4)	1.0563 (3)	0.33276 (17)	0.0766 (8)
H21A	1.401455	1.105457	0.329712	0.092*
C22	1.3038 (3)	0.9565 (2)	0.29124 (15)	0.0642 (6)
H22A	1.407992	0.937882	0.259970	0.077*
C23	1.1527 (3)	0.8830 (2)	0.29563 (13)	0.0527 (5)
H23A	1.155681	0.815337	0.267201	0.063*
C24	0.7924 (3)	0.84768 (18)	0.16696 (12)	0.0438 (5)
C25	0.8062 (3)	0.85576 (19)	0.07748 (12)	0.0469 (5)
C26	0.7499 (3)	0.9703 (2)	0.02607 (14)	0.0623 (6)
H26A	0.703596	1.041174	0.048177	0.075*
C27	0.7615 (4)	0.9808 (3)	−0.05686 (15)	0.0782 (8)
H27A	0.723599	1.058504	−0.090560	0.094*
C28	0.8287 (4)	0.8769 (3)	−0.09014 (15)	0.0817 (8)
H28A	0.836448	0.884338	−0.146453	0.098*
C29	0.8843 (4)	0.7627 (3)	−0.04106 (15)	0.0809 (8)
H29A	0.929398	0.692340	−0.063924	0.097*
C30	0.8737 (4)	0.7515 (2)	0.04271 (14)	0.0647 (6)
H30A	0.911977	0.673403	0.075957	0.078*
N6	0.3729 (4)	0.5581 (3)	0.13166 (19)	0.0906 (8)
O1A	0.3951 (6)	0.6676 (4)	0.1010 (3)	0.1231 (16)	0.876 (7)
O2A	0.2222 (4)	0.5095 (3)	0.1392 (2)	0.1287 (16)	0.876 (7)
O1B	0.307 (5)	0.642 (4)	0.154 (3)	0.149 (13)	0.124 (7)
O2B	0.360 (5)	0.567 (3)	0.0504 (17)	0.209 (16)	0.124 (7)
N12	0.3353 (2)	0.47251 (18)	0.35551 (12)	0.0607 (5)
O3	0.2211 (3)	0.3957 (2)	0.3593 (2)	0.1493 (13)
O4	0.3067 (2)	0.58039 (15)	0.31765 (11)	0.0740 (5)
O17	0.7042 (2)	0.85530 (15)	0.39699 (10)	0.0658 (5)
O24	0.7394 (2)	0.94134 (13)	0.19653 (9)	0.0615 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0485 (11)	0.0308 (9)	0.0445 (10)	−0.0046 (8)	−0.0076 (8)	−0.0030 (8)
C2	0.0457 (10)	0.0316 (9)	0.0440 (10)	−0.0048 (8)	−0.0007 (8)	−0.0055 (8)
C3	0.0470 (10)	0.0339 (10)	0.0421 (10)	−0.0059 (8)	−0.0030 (8)	−0.0023 (8)
C4	0.0483 (11)	0.0326 (10)	0.0421 (10)	−0.0035 (8)	0.0017 (8)	−0.0049 (8)
C5	0.0628 (13)	0.0345 (10)	0.0422 (11)	−0.0086 (9)	0.0004 (9)	−0.0051 (8)
C6	0.0732 (16)	0.0551 (14)	0.0720 (15)	−0.0143 (12)	−0.0027 (12)	−0.0229 (12)
C7	0.113 (2)	0.0699 (19)	0.122 (3)	−0.0273 (18)	−0.004 (2)	−0.0510 (18)
C8	0.141 (3)	0.0449 (15)	0.117 (3)	−0.0163 (18)	0.019 (2)	−0.0380 (16)
C9	0.120 (2)	0.0465 (14)	0.0735 (17)	0.0141 (14)	0.0103 (16)	−0.0105 (12)
C10	0.0822 (16)	0.0420 (12)	0.0506 (12)	0.0059 (11)	−0.0009 (11)	−0.0074 (9)
C11	0.0531 (11)	0.0351 (10)	0.0397 (10)	−0.0077 (8)	0.0028 (8)	−0.0076 (8)
C12	0.0520 (12)	0.0402 (11)	0.0480 (11)	−0.0092 (9)	0.0055 (9)	−0.0082 (8)
C13	0.0727 (15)	0.0432 (12)	0.0525 (12)	−0.0185 (11)	0.0069 (11)	−0.0035 (9)
C14	0.0940 (18)	0.0417 (12)	0.0511 (13)	−0.0135 (12)	−0.0039 (12)	0.0056 (10)
C15	0.0793 (16)	0.0530 (13)	0.0561 (13)	−0.0101 (12)	−0.0166 (11)	0.0084 (10)
C16	0.0667 (14)	0.0472 (12)	0.0531 (12)	−0.0158 (10)	−0.0126 (10)	0.0037 (9)
C17	0.0540 (12)	0.0406 (11)	0.0396 (10)	−0.0094 (9)	−0.0002 (9)	−0.0045 (8)
C18	0.0523 (11)	0.0374 (10)	0.0425 (10)	−0.0107 (9)	−0.0059 (9)	0.0019 (8)
C19	0.0747 (15)	0.0518 (13)	0.0689 (15)	−0.0207 (11)	0.0016 (12)	−0.0192 (11)
C20	0.094 (2)	0.0624 (16)	0.0895 (19)	−0.0351 (14)	−0.0022 (16)	−0.0237 (14)
C21	0.0775 (18)	0.0671 (17)	0.0843 (18)	−0.0349 (14)	−0.0142 (14)	0.0031 (14)
C22	0.0563 (13)	0.0607 (15)	0.0687 (15)	−0.0143 (11)	−0.0032 (11)	0.0093 (12)
C23	0.0547 (12)	0.0450 (12)	0.0552 (12)	−0.0096 (10)	−0.0055 (10)	0.0022 (9)
C24	0.0495 (11)	0.0356 (10)	0.0455 (11)	−0.0080 (8)	0.0035 (8)	−0.0047 (8)
C25	0.0509 (11)	0.0442 (11)	0.0444 (11)	−0.0103 (9)	0.0007 (9)	−0.0029 (9)
C26	0.0765 (15)	0.0528 (13)	0.0530 (13)	0.0000 (11)	−0.0017 (11)	−0.0003 (10)
C27	0.0956 (19)	0.0791 (18)	0.0502 (14)	0.0041 (15)	−0.0057 (13)	0.0078 (13)
C28	0.106 (2)	0.094 (2)	0.0416 (13)	−0.0032 (17)	−0.0048 (13)	−0.0059 (14)
C29	0.114 (2)	0.0783 (18)	0.0509 (14)	0.0014 (15)	0.0051 (14)	−0.0198 (13)
C30	0.0890 (17)	0.0526 (13)	0.0501 (13)	−0.0018 (12)	0.0024 (11)	−0.0066 (10)
N6	0.0822 (18)	0.0880 (19)	0.114 (2)	−0.0055 (17)	−0.0415 (15)	−0.0410 (19)
O1A	0.133 (3)	0.084 (2)	0.150 (4)	−0.005 (2)	−0.085 (3)	0.002 (2)
O2A	0.0728 (18)	0.148 (3)	0.183 (4)	−0.0225 (16)	−0.0267 (17)	−0.064 (2)
O1B	0.15 (2)	0.12 (2)	0.19 (3)	0.075 (19)	−0.081 (19)	−0.08 (2)
O2B	0.27 (3)	0.25 (3)	0.12 (2)	0.09 (2)	−0.13 (2)	−0.109 (19)
N12	0.0526 (11)	0.0481 (11)	0.0804 (13)	−0.0163 (9)	0.0023 (9)	−0.0054 (10)
O3	0.1017 (17)	0.0876 (15)	0.241 (3)	−0.0563 (14)	−0.0743 (18)	0.0496 (17)
O4	0.0612 (10)	0.0490 (10)	0.1066 (14)	−0.0061 (8)	−0.0150 (9)	0.0015 (9)
O17	0.0734 (10)	0.0636 (10)	0.0683 (10)	−0.0249 (8)	0.0213 (8)	−0.0288 (8)
O24	0.0923 (11)	0.0372 (8)	0.0528 (9)	0.0021 (7)	−0.0004 (8)	−0.0066 (7)

Geometric parameters (Å, º)

C1—C5	1.499 (3)	C16—H16A	0.9300
C1—C4	1.569 (3)	C17—O17	1.217 (2)
C1—C2	1.580 (3)	C17—C18	1.491 (3)
C1—H1A	0.9800	C18—C19	1.383 (3)
C2—C11	1.514 (2)	C18—C23	1.384 (3)
C2—C3	1.542 (2)	C19—C20	1.375 (3)
C2—H2A	0.9800	C19—H19A	0.9300
C3—C17	1.519 (3)	C20—C21	1.371 (4)
C3—C4	1.557 (3)	C20—H20A	0.9300
C3—H3A	0.9800	C21—C22	1.368 (4)
C4—C24	1.504 (3)	C21—H21A	0.9300
C4—H4A	0.9800	C22—C23	1.387 (3)
C5—C10	1.390 (3)	C22—H22A	0.9300
C5—C6	1.397 (3)	C23—H23A	0.9300
C6—C7	1.380 (3)	C24—O24	1.217 (2)
C6—N6	1.469 (4)	C24—C25	1.483 (3)
C7—C8	1.359 (5)	C25—C26	1.385 (3)
C7—H7A	0.9300	C25—C30	1.387 (3)
C8—C9	1.372 (4)	C26—C27	1.370 (3)
C8—H8A	0.9300	C26—H26A	0.9300
C9—C10	1.376 (3)	C27—C28	1.369 (4)
C9—H9A	0.9300	C27—H27A	0.9300
C10—H10A	0.9300	C28—C29	1.363 (4)
C11—C16	1.383 (3)	C28—H28A	0.9300
C11—C12	1.401 (3)	C29—C30	1.383 (3)
C12—C13	1.393 (3)	C29—H29A	0.9300
C12—N12	1.460 (3)	C30—H30A	0.9300
C13—C14	1.360 (3)	N6—O1B	1.09 (3)
C13—H13A	0.9300	N6—O1A	1.192 (4)
C14—C15	1.369 (3)	N6—O2A	1.238 (4)
C14—H14A	0.9300	N6—O2B	1.35 (2)
C15—C16	1.384 (3)	N12—O3	1.198 (2)
C15—H15A	0.9300	N12—O4	1.198 (2)
C5—C1—C4	117.35 (16)	C16—C15—H15A	119.7
C5—C1—C2	117.82 (14)	C11—C16—C15	123.0 (2)
C4—C1—C2	88.90 (13)	C11—C16—H16A	118.5
C5—C1—H1A	110.4	C15—C16—H16A	118.5
C4—C1—H1A	110.4	O17—C17—C18	120.32 (18)
C2—C1—H1A	110.4	O17—C17—C3	119.49 (17)
C11—C2—C3	119.52 (15)	C18—C17—C3	119.87 (17)
C11—C2—C1	118.78 (14)	C19—C18—C23	118.94 (19)
C3—C2—C1	90.19 (13)	C19—C18—C17	118.30 (19)
C11—C2—H2A	109.0	C23—C18—C17	122.71 (18)
C3—C2—H2A	109.0	C20—C19—C18	120.4 (2)
C1—C2—H2A	109.0	C20—C19—H19A	119.8
C17—C3—C2	114.65 (15)	C18—C19—H19A	119.8
C17—C3—C4	122.24 (15)	C21—C20—C19	120.4 (2)
C2—C3—C4	90.76 (13)	C21—C20—H20A	119.8
C17—C3—H3A	109.2	C19—C20—H20A	119.8
C2—C3—H3A	109.2	C22—C21—C20	119.9 (2)
C4—C3—H3A	109.2	C22—C21—H21A	120.0
C24—C4—C3	119.06 (15)	C20—C21—H21A	120.0
C24—C4—C1	110.24 (15)	C21—C22—C23	120.2 (2)
C3—C4—C1	90.03 (13)	C21—C22—H22A	119.9
C24—C4—H4A	111.9	C23—C22—H22A	119.9
C3—C4—H4A	111.9	C18—C23—C22	120.1 (2)
C1—C4—H4A	111.9	C18—C23—H23A	119.9
C10—C5—C6	115.99 (19)	C22—C23—H23A	119.9
C10—C5—C1	119.59 (18)	O24—C24—C25	121.40 (17)
C6—C5—C1	124.18 (19)	O24—C24—C4	119.91 (17)
C7—C6—C5	122.2 (3)	C25—C24—C4	118.55 (16)
C7—C6—N6	116.4 (2)	C26—C25—C30	118.15 (19)
C5—C6—N6	121.5 (2)	C26—C25—C24	119.69 (19)
C8—C7—C6	119.8 (3)	C30—C25—C24	122.16 (18)
C8—C7—H7A	120.1	C27—C26—C25	121.0 (2)
C6—C7—H7A	120.1	C27—C26—H26A	119.5
C7—C8—C9	120.1 (2)	C25—C26—H26A	119.5
C7—C8—H8A	120.0	C28—C27—C26	120.0 (2)
C9—C8—H8A	120.0	C28—C27—H27A	120.0
C8—C9—C10	120.0 (3)	C26—C27—H27A	120.0
C8—C9—H9A	120.0	C29—C28—C27	120.2 (2)
C10—C9—H9A	120.0	C29—C28—H28A	119.9
C9—C10—C5	122.0 (2)	C27—C28—H28A	119.9
C9—C10—H10A	119.0	C28—C29—C30	120.1 (2)
C5—C10—H10A	119.0	C28—C29—H29A	120.0
C16—C11—C12	114.61 (17)	C30—C29—H29A	120.0
C16—C11—C2	120.86 (16)	C29—C30—C25	120.5 (2)
C12—C11—C2	124.52 (17)	C29—C30—H30A	119.8
C13—C12—C11	122.70 (19)	C25—C30—H30A	119.8
C13—C12—N12	115.67 (17)	O1A—N6—O2A	124.8 (3)
C11—C12—N12	121.63 (17)	O1B—N6—O2B	114 (2)
C14—C13—C12	120.2 (2)	O1B—N6—C6	129.1 (15)
C14—C13—H13A	119.9	O1A—N6—C6	119.5 (3)
C12—C13—H13A	119.9	O2A—N6—C6	115.7 (3)
C13—C14—C15	119.0 (2)	O2B—N6—C6	111.4 (13)
C13—C14—H14A	120.5	O3—N12—O4	120.1 (2)
C15—C14—H14A	120.5	O3—N12—C12	119.1 (2)
C14—C15—C16	120.5 (2)	O4—N12—C12	120.80 (17)
C14—C15—H15A	119.7
C5—C1—C2—C11	−6.2 (2)	C14—C15—C16—C11	−1.3 (4)
C4—C1—C2—C11	−126.84 (16)	C2—C3—C17—O17	8.2 (3)
C5—C1—C2—C3	118.12 (17)	C4—C3—C17—O17	116.0 (2)
C4—C1—C2—C3	−2.51 (13)	C2—C3—C17—C18	−178.33 (15)
C11—C2—C3—C17	−107.37 (19)	C4—C3—C17—C18	−70.5 (2)
C1—C2—C3—C17	128.91 (15)	O17—C17—C18—C19	−0.5 (3)
C11—C2—C3—C4	126.25 (17)	C3—C17—C18—C19	−173.92 (18)
C1—C2—C3—C4	2.53 (13)	O17—C17—C18—C23	176.93 (19)
C17—C3—C4—C24	−9.3 (3)	C3—C17—C18—C23	3.5 (3)
C2—C3—C4—C24	110.78 (17)	C23—C18—C19—C20	−0.4 (3)
C17—C3—C4—C1	−122.65 (18)	C17—C18—C19—C20	177.1 (2)
C2—C3—C4—C1	−2.55 (13)	C18—C19—C20—C21	0.3 (4)
C5—C1—C4—C24	120.25 (17)	C19—C20—C21—C22	−0.1 (4)
C2—C1—C4—C24	−118.70 (15)	C20—C21—C22—C23	0.0 (4)
C5—C1—C4—C3	−118.56 (16)	C19—C18—C23—C22	0.4 (3)
C2—C1—C4—C3	2.49 (13)	C17—C18—C23—C22	−177.02 (18)
C4—C1—C5—C10	50.3 (2)	C21—C22—C23—C18	−0.2 (3)
C2—C1—C5—C10	−54.1 (2)	C3—C4—C24—O24	−10.5 (3)
C4—C1—C5—C6	−135.5 (2)	C1—C4—C24—O24	91.3 (2)
C2—C1—C5—C6	120.1 (2)	C3—C4—C24—C25	173.63 (16)
C10—C5—C6—C7	1.4 (4)	C1—C4—C24—C25	−84.5 (2)
C1—C5—C6—C7	−173.0 (2)	O24—C24—C25—C26	−3.1 (3)
C10—C5—C6—N6	−178.7 (2)	C4—C24—C25—C26	172.72 (19)
C1—C5—C6—N6	7.0 (4)	O24—C24—C25—C30	177.2 (2)
C5—C6—C7—C8	−0.5 (5)	C4—C24—C25—C30	−7.0 (3)
N6—C6—C7—C8	179.5 (3)	C30—C25—C26—C27	−0.4 (3)
C6—C7—C8—C9	−0.7 (5)	C24—C25—C26—C27	179.9 (2)
C7—C8—C9—C10	1.0 (5)	C25—C26—C27—C28	0.3 (4)
C8—C9—C10—C5	−0.1 (4)	C26—C27—C28—C29	0.0 (4)
C6—C5—C10—C9	−1.1 (3)	C27—C28—C29—C30	−0.3 (5)
C1—C5—C10—C9	173.6 (2)	C28—C29—C30—C25	0.1 (4)
C3—C2—C11—C16	5.1 (3)	C26—C25—C30—C29	0.2 (3)
C1—C2—C11—C16	113.4 (2)	C24—C25—C30—C29	179.9 (2)
C3—C2—C11—C12	−173.80 (17)	C7—C6—N6—O1B	153 (4)
C1—C2—C11—C12	−65.4 (2)	C5—C6—N6—O1B	−27 (4)
C16—C11—C12—C13	−1.4 (3)	C7—C6—N6—O1A	−137.9 (4)
C2—C11—C12—C13	177.54 (18)	C5—C6—N6—O1A	42.2 (5)
C16—C11—C12—N12	178.28 (18)	C7—C6—N6—O2A	41.9 (4)
C2—C11—C12—N12	−2.8 (3)	C5—C6—N6—O2A	−138.0 (3)
C11—C12—C13—C14	0.5 (3)	C7—C6—N6—O2B	−56 (2)
N12—C12—C13—C14	−179.2 (2)	C5—C6—N6—O2B	124 (2)
C12—C13—C14—C15	0.1 (3)	C13—C12—N12—O3	−9.5 (3)
C13—C14—C15—C16	0.2 (4)	C11—C12—N12—O3	170.8 (3)
C12—C11—C16—C15	1.8 (3)	C13—C12—N12—O4	169.5 (2)
C2—C11—C16—C15	−177.2 (2)	C11—C12—N12—O4	−10.2 (3)