1,8-Bis(3-formyl-5-methyl-2-oxido­benzyl)-1,8-diaza-4,11-diazo­niacyclo­tetra­decane chloro­form solvate

The title compound, C₂₈H₄₀N₄O₄·CHCl₃, crystallizes with two half-mol­ecules of the macrocycle and one molecule of chloro­form solvent in the asymmetric unit. Each macrocycle lies on a centre of inversion. The mol­ecular structure is stabilized by N—H...O and C—H...O intra­molecular inter­actions, and the crystal packing is stabilized by C—H...O and C—H...π inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.161
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C29
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O2
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O4
PLAT432_ALERT_2_C Short Inter X...Y Contact  Cl3    ..  C3      ..       3.22 Ang.
PLAT731_ALERT_1_C Bond    Calc   0.898(19), Rep    0.899(9) ......       2.11 su-Ra
              N2   -H2B     1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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 and PARST (Nardelli, 1995).

1,8-Bis(3-formyl-2-oxido-5-methylbenzyl}-1,8-diaza-4,11-diazoniacyclotetradecane chloroform solvate

Crystal data

C28H40N4O4·CHCl3	Z = 2
Mr = 616.01	F(000) = 652
Triclinic, P1	Dx = 1.329 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1366 (5) Å	Cell parameters from 3495 reflections
b = 11.2816 (5) Å	θ = 2.0–25.0°
c = 14.2124 (7) Å	µ = 0.34 mm^−1
α = 69.564 (1)°	T = 293 K
β = 84.559 (1)°	Block, yellow
γ = 67.110 (1)°	0.29 × 0.26 × 0.25 mm
V = 1539.74 (12) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5878 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 28.0°, θmin = 2.0°
ω scans	h = −14→14
17829 measured reflections	k = −14→14
7069 independent reflections	l = −18→18

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0823P)^2 + 0.5118P] where P = (Fo^2 + 2Fc^2)/3
7069 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.69 e Å^−3
4 restraints	Δρmin = −0.43 e Å^−3

Special details

Experimental. 4,11-diammonium-1,8-N,N'-bis{(3-formyl-2-oxido-5-methyl)benzyl}-1,4,8,11- tetra-azacyclotetradecane

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
C1	0.0050 (3)	0.8854 (3)	0.7527 (2)	0.0834 (8)
H1A	0.0310	0.9424	0.7761	0.125*
H1B	−0.0459	0.8452	0.8021	0.125*
H1C	−0.0463	0.9397	0.6908	0.125*
C2	0.1251 (2)	0.7732 (2)	0.73525 (15)	0.0538 (5)
C3	0.2454 (2)	0.73944 (19)	0.77505 (14)	0.0497 (4)
H3	0.2542	0.7878	0.8135	0.060*
C4	0.35595 (18)	0.63460 (18)	0.76012 (12)	0.0426 (4)
C5	0.34739 (17)	0.55977 (17)	0.70034 (12)	0.0407 (4)
C6	0.22160 (17)	0.59600 (18)	0.65827 (12)	0.0410 (4)
C7	0.11554 (18)	0.6989 (2)	0.67672 (13)	0.0482 (4)
H7	0.0341	0.7201	0.6493	0.058*
C8	0.4813 (2)	0.6005 (2)	0.80579 (15)	0.0532 (5)
H8	0.5528	0.5340	0.7901	0.064*
C9	0.20974 (18)	0.5187 (2)	0.59475 (13)	0.0456 (4)
H9A	0.2484	0.4212	0.6315	0.055*
H9B	0.1182	0.5426	0.5803	0.055*
C10	0.19447 (18)	0.68522 (19)	0.42880 (13)	0.0469 (4)
H10A	0.1500	0.7459	0.4664	0.056*
H10B	0.1284	0.6743	0.3965	0.056*
C11	0.27054 (19)	0.75145 (19)	0.34845 (13)	0.0498 (4)
H11A	0.3165	0.6897	0.3119	0.060*
H11B	0.2094	0.8342	0.3012	0.060*
C12	0.3122 (2)	0.4430 (2)	0.45447 (14)	0.0487 (4)
H12A	0.3421	0.4752	0.3875	0.058*
H12B	0.2356	0.4249	0.4481	0.058*
C13	0.4186 (2)	0.31061 (19)	0.51634 (15)	0.0510 (4)
H13A	0.3806	0.2613	0.5729	0.061*
H13B	0.4574	0.2535	0.4753	0.061*
C14	0.6322 (2)	0.21277 (18)	0.61211 (16)	0.0529 (5)
H14A	0.6754	0.1594	0.5692	0.063*
H14B	0.5989	0.1570	0.6680	0.063*
C15	0.1705 (2)	1.0779 (3)	0.54136 (18)	0.0699 (6)
H15A	0.2104	1.0925	0.4776	0.105*
H15B	0.0916	1.1557	0.5374	0.105*
H15C	0.1506	0.9976	0.5583	0.105*
C16	0.26353 (19)	1.0588 (2)	0.62128 (14)	0.0483 (4)
C17	0.39104 (19)	0.97072 (19)	0.63108 (14)	0.0468 (4)
H17	0.4204	0.9202	0.5881	0.056*
C18	0.47940 (18)	0.95343 (17)	0.70331 (12)	0.0413 (4)
C19	0.43978 (17)	1.03102 (16)	0.76933 (11)	0.0384 (3)
C20	0.30609 (17)	1.12130 (17)	0.75957 (12)	0.0407 (4)
C21	0.22303 (18)	1.13237 (19)	0.68785 (13)	0.0453 (4)
H21	0.1362	1.1914	0.6836	0.054*
C22	0.6127 (2)	0.8550 (2)	0.71203 (15)	0.0525 (4)
H22	0.6691	0.8502	0.7587	0.063*
C23	0.26149 (19)	1.21183 (18)	0.82268 (13)	0.0463 (4)
H23A	0.3079	1.2732	0.8048	0.056*
H23B	0.1692	1.2673	0.8079	0.056*
C24	0.1927 (2)	1.0639 (2)	0.96753 (15)	0.0567 (5)
H24A	0.1744	1.0364	0.9148	0.068*
H24B	0.1111	1.1275	0.9818	0.068*
C25	0.2446 (2)	0.9387 (2)	1.06130 (16)	0.0593 (5)
H25A	0.2662	0.9664	1.1127	0.071*
H25B	0.1755	0.9051	1.0858	0.071*
C26	0.2798 (2)	1.2214 (2)	0.98808 (14)	0.0529 (5)
H26A	0.2798	1.1724	1.0593	0.063*
H26B	0.1998	1.3024	0.9697	0.063*
C27	0.3952 (2)	1.26439 (19)	0.96819 (15)	0.0542 (5)
H27A	0.3816	1.3363	0.9032	0.065*
H27B	0.4030	1.3004	1.0191	0.065*
C28	0.6367 (2)	1.1780 (2)	0.95207 (17)	0.0601 (5)
H28A	0.6539	1.1993	1.0086	0.072*
H28B	0.6214	1.2585	0.8925	0.072*
C29	0.1760 (2)	0.5116 (2)	0.13106 (16)	0.0566 (5)
H29	0.2613	0.4381	0.1560	0.068*
N1	0.27589 (14)	0.55101 (14)	0.49936 (10)	0.0401 (3)
N2	0.52114 (15)	0.33812 (14)	0.55384 (12)	0.0431 (3)
H2A	0.486 (2)	0.385 (2)	0.5965 (16)	0.073 (7)*
H2B	0.554 (2)	0.3862 (19)	0.5012 (12)	0.052 (6)*
N3	0.28326 (15)	1.13394 (15)	0.93124 (10)	0.0438 (3)
N4	0.51743 (16)	1.14565 (15)	0.96955 (11)	0.0448 (3)
H4A	0.513 (2)	1.114 (2)	0.9202 (14)	0.062 (6)*
H4B	0.522 (2)	1.0807 (18)	1.0299 (10)	0.057 (6)*
O1	0.50187 (18)	0.65046 (18)	0.86273 (12)	0.0709 (4)
O2	0.44953 (13)	0.46180 (15)	0.68592 (12)	0.0585 (4)
O3	0.65720 (17)	0.77854 (18)	0.66422 (14)	0.0749 (5)
O4	0.52180 (12)	1.02169 (13)	0.83351 (9)	0.0454 (3)
Cl1	0.13923 (8)	0.62388 (9)	0.19877 (6)	0.0893 (2)
Cl2	0.06037 (7)	0.43912 (8)	0.14658 (6)	0.0892 (2)
Cl3	0.18474 (9)	0.59785 (8)	0.00379 (5)	0.0924 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0694 (15)	0.0706 (15)	0.0936 (19)	0.0019 (12)	0.0147 (14)	−0.0436 (15)
C2	0.0547 (11)	0.0479 (10)	0.0485 (10)	−0.0074 (8)	0.0127 (8)	−0.0207 (8)
C3	0.0643 (12)	0.0436 (9)	0.0426 (9)	−0.0167 (8)	0.0104 (8)	−0.0226 (8)
C4	0.0516 (10)	0.0415 (9)	0.0353 (8)	−0.0159 (7)	0.0043 (7)	−0.0164 (7)
C5	0.0450 (9)	0.0410 (8)	0.0357 (8)	−0.0127 (7)	0.0047 (7)	−0.0175 (7)
C6	0.0449 (9)	0.0459 (9)	0.0325 (8)	−0.0176 (7)	0.0072 (6)	−0.0148 (7)
C7	0.0425 (9)	0.0540 (10)	0.0395 (9)	−0.0117 (8)	0.0058 (7)	−0.0143 (8)
C8	0.0609 (11)	0.0544 (11)	0.0506 (10)	−0.0207 (9)	−0.0017 (9)	−0.0255 (9)
C9	0.0490 (9)	0.0553 (10)	0.0388 (8)	−0.0246 (8)	0.0045 (7)	−0.0187 (8)
C10	0.0416 (9)	0.0517 (10)	0.0377 (8)	−0.0057 (7)	−0.0021 (7)	−0.0166 (8)
C11	0.0527 (10)	0.0426 (9)	0.0357 (8)	−0.0021 (8)	−0.0008 (7)	−0.0093 (7)
C12	0.0603 (11)	0.0524 (10)	0.0408 (9)	−0.0224 (9)	0.0010 (8)	−0.0230 (8)
C13	0.0667 (12)	0.0431 (9)	0.0512 (10)	−0.0214 (9)	0.0035 (9)	−0.0250 (8)
C14	0.0580 (11)	0.0328 (8)	0.0567 (11)	−0.0080 (8)	0.0050 (9)	−0.0133 (8)
C15	0.0636 (13)	0.0947 (17)	0.0595 (13)	−0.0228 (12)	−0.0082 (10)	−0.0412 (13)
C16	0.0550 (10)	0.0546 (10)	0.0398 (9)	−0.0210 (9)	−0.0022 (8)	−0.0200 (8)
C17	0.0588 (11)	0.0464 (9)	0.0407 (9)	−0.0183 (8)	0.0018 (8)	−0.0230 (8)
C18	0.0505 (9)	0.0390 (8)	0.0345 (8)	−0.0149 (7)	0.0016 (7)	−0.0151 (7)
C19	0.0486 (9)	0.0358 (8)	0.0292 (7)	−0.0146 (7)	−0.0001 (6)	−0.0104 (6)
C20	0.0499 (9)	0.0389 (8)	0.0309 (7)	−0.0130 (7)	−0.0005 (7)	−0.0132 (6)
C21	0.0467 (9)	0.0482 (9)	0.0373 (8)	−0.0129 (8)	−0.0013 (7)	−0.0153 (7)
C22	0.0554 (11)	0.0535 (10)	0.0474 (10)	−0.0120 (9)	0.0000 (8)	−0.0252 (9)
C23	0.0531 (10)	0.0423 (9)	0.0346 (8)	−0.0049 (7)	−0.0041 (7)	−0.0163 (7)
C24	0.0501 (10)	0.0751 (14)	0.0453 (10)	−0.0222 (10)	0.0031 (8)	−0.0230 (10)
C25	0.0644 (12)	0.0739 (14)	0.0459 (10)	−0.0355 (11)	0.0085 (9)	−0.0188 (10)
C26	0.0589 (11)	0.0527 (10)	0.0396 (9)	−0.0041 (9)	−0.0027 (8)	−0.0253 (8)
C27	0.0734 (13)	0.0414 (9)	0.0460 (10)	−0.0116 (9)	−0.0088 (9)	−0.0217 (8)
C28	0.0770 (14)	0.0577 (12)	0.0564 (12)	−0.0378 (11)	0.0035 (10)	−0.0184 (10)
C29	0.0506 (11)	0.0587 (12)	0.0585 (12)	−0.0194 (9)	−0.0030 (9)	−0.0177 (10)
N1	0.0452 (7)	0.0424 (7)	0.0324 (7)	−0.0134 (6)	0.0015 (6)	−0.0162 (6)
N2	0.0501 (8)	0.0330 (7)	0.0451 (8)	−0.0128 (6)	0.0076 (6)	−0.0168 (6)
N3	0.0492 (8)	0.0475 (8)	0.0326 (7)	−0.0116 (7)	0.0009 (6)	−0.0187 (6)
N4	0.0597 (9)	0.0395 (8)	0.0364 (7)	−0.0181 (7)	−0.0030 (6)	−0.0138 (6)
O1	0.0853 (11)	0.0798 (11)	0.0633 (9)	−0.0329 (9)	−0.0093 (8)	−0.0378 (8)
O2	0.0458 (7)	0.0652 (9)	0.0699 (9)	−0.0035 (6)	−0.0032 (6)	−0.0478 (8)
O3	0.0693 (10)	0.0773 (11)	0.0772 (11)	−0.0033 (8)	0.0002 (8)	−0.0523 (9)
O4	0.0490 (7)	0.0504 (7)	0.0366 (6)	−0.0116 (5)	−0.0036 (5)	−0.0214 (5)
Cl1	0.0933 (5)	0.1053 (5)	0.0847 (5)	−0.0307 (4)	−0.0087 (4)	−0.0548 (4)
Cl2	0.0839 (5)	0.0919 (5)	0.1061 (6)	−0.0537 (4)	0.0083 (4)	−0.0285 (4)
Cl3	0.1177 (6)	0.0947 (5)	0.0660 (4)	−0.0497 (5)	0.0198 (4)	−0.0221 (4)

Geometric parameters (Å, º)

C1—C2	1.514 (3)	C16—C17	1.366 (3)
C1—H1A	0.96	C16—C21	1.401 (3)
C1—H1B	0.96	C17—C18	1.401 (3)
C1—H1C	0.96	C17—H17	0.93
C2—C3	1.362 (3)	C18—C19	1.427 (2)
C2—C7	1.407 (3)	C18—C22	1.452 (3)
C3—C4	1.398 (3)	C19—O4	1.301 (2)
C3—H3	0.93	C19—C20	1.426 (2)
C4—C5	1.422 (2)	C20—C21	1.382 (2)
C4—C8	1.448 (3)	C20—C23	1.502 (2)
C5—O2	1.301 (2)	C21—H21	0.93
C5—C6	1.425 (2)	C22—O3	1.210 (2)
C6—C7	1.378 (2)	C22—H22	0.93
C6—C9	1.501 (2)	C23—N3	1.473 (2)
C7—H7	0.93	C23—H23A	0.97
C8—O1	1.217 (2)	C23—H23B	0.97
C8—H8	0.93	C24—N3	1.465 (3)
C9—N1	1.479 (2)	C24—C25	1.517 (3)
C9—H9A	0.97	C24—H24A	0.97
C9—H9B	0.97	C24—H24B	0.97
C10—N1	1.471 (2)	C25—C28^ii	1.513 (3)
C10—C11	1.514 (3)	C25—H25A	0.97
C10—H10A	0.97	C25—H25B	0.97
C10—H10B	0.97	C26—N3	1.466 (2)
C11—C14^i	1.504 (3)	C26—C27	1.512 (3)
C11—H11A	0.97	C26—H26A	0.97
C11—H11B	0.97	C26—H26B	0.97
C12—N1	1.472 (2)	C27—N4	1.489 (2)
C12—C13	1.521 (3)	C27—H27A	0.97
C12—H12A	0.97	C27—H27B	0.97
C12—H12B	0.97	C28—N4	1.487 (3)
C13—N2	1.480 (3)	C28—C25^ii	1.513 (3)
C13—H13A	0.97	C28—H28A	0.97
C13—H13B	0.97	C28—H28B	0.97
C14—N2	1.494 (2)	C29—Cl2	1.736 (2)
C14—C11^i	1.504 (3)	C29—Cl3	1.743 (2)
C14—H14A	0.97	C29—Cl1	1.753 (2)
C14—H14B	0.97	C29—H29	0.98
C15—C16	1.512 (3)	N2—H2A	0.902 (10)
C15—H15A	0.96	N2—H2B	0.899 (9)
C15—H15B	0.96	N4—H4A	0.905 (10)
C15—H15C	0.96	N4—H4B	0.903 (9)
C2—C1—H1A	109.5	C17—C18—C19	120.72 (16)
C2—C1—H1B	109.5	C17—C18—C22	119.98 (16)
H1A—C1—H1B	109.5	C19—C18—C22	119.30 (16)
C2—C1—H1C	109.5	O4—C19—C20	121.95 (14)
H1A—C1—H1C	109.5	O4—C19—C18	121.75 (16)
H1B—C1—H1C	109.5	C20—C19—C18	116.29 (15)
C3—C2—C7	117.38 (17)	C21—C20—C19	120.30 (15)
C3—C2—C1	122.2 (2)	C21—C20—C23	121.16 (16)
C7—C2—C1	120.4 (2)	C19—C20—C23	118.33 (15)
C2—C3—C4	122.22 (18)	C20—C21—C16	123.10 (17)
C2—C3—H3	118.9	C20—C21—H21	118.5
C4—C3—H3	118.9	C16—C21—H21	118.5
C3—C4—C5	120.77 (17)	O3—C22—C18	126.02 (19)
C3—C4—C8	120.21 (17)	O3—C22—H22	117.0
C5—C4—C8	119.02 (16)	C18—C22—H22	117.0
O2—C5—C4	121.41 (16)	N3—C23—C20	112.74 (14)
O2—C5—C6	121.75 (15)	N3—C23—H23A	109.0
C4—C5—C6	116.84 (15)	C20—C23—H23A	109.0
C7—C6—C5	119.94 (16)	N3—C23—H23B	109.0
C7—C6—C9	122.09 (17)	C20—C23—H23B	109.0
C5—C6—C9	117.97 (15)	H23A—C23—H23B	107.8
C6—C7—C2	122.84 (18)	N3—C24—C25	113.20 (17)
C6—C7—H7	118.6	N3—C24—H24A	108.9
C2—C7—H7	118.6	C25—C24—H24A	108.9
O1—C8—C4	126.2 (2)	N3—C24—H24B	108.9
O1—C8—H8	116.9	C25—C24—H24B	108.9
C4—C8—H8	116.9	H24A—C24—H24B	107.8
N1—C9—C6	110.91 (14)	C28^ii—C25—C24	115.44 (18)
N1—C9—H9A	109.5	C28^ii—C25—H25A	108.4
C6—C9—H9A	109.5	C24—C25—H25A	108.4
N1—C9—H9B	109.5	C28^ii—C25—H25B	108.4
C6—C9—H9B	109.5	C24—C25—H25B	108.4
H9A—C9—H9B	108.0	H25A—C25—H25B	107.5
N1—C10—C11	113.72 (15)	N3—C26—C27	111.88 (15)
N1—C10—H10A	108.8	N3—C26—H26A	109.2
C11—C10—H10A	108.8	C27—C26—H26A	109.2
N1—C10—H10B	108.8	N3—C26—H26B	109.2
C11—C10—H10B	108.8	C27—C26—H26B	109.2
H10A—C10—H10B	107.7	H26A—C26—H26B	107.9
C14^i—C11—C10	114.36 (16)	N4—C27—C26	110.35 (15)
C14^i—C11—H11A	108.7	N4—C27—H27A	109.6
C10—C11—H11A	108.7	C26—C27—H27A	109.6
C14^i—C11—H11B	108.7	N4—C27—H27B	109.6
C10—C11—H11B	108.7	C26—C27—H27B	109.6
H11A—C11—H11B	107.6	H27A—C27—H27B	108.1
N1—C12—C13	112.65 (14)	N4—C28—C25^ii	112.64 (17)
N1—C12—H12A	109.1	N4—C28—H28A	109.1
C13—C12—H12A	109.1	C25^ii—C28—H28A	109.1
N1—C12—H12B	109.1	N4—C28—H28B	109.1
C13—C12—H12B	109.1	C25^ii—C28—H28B	109.1
H12A—C12—H12B	107.8	H28A—C28—H28B	107.8
N2—C13—C12	111.13 (15)	Cl2—C29—Cl3	109.77 (12)
N2—C13—H13A	109.4	Cl2—C29—Cl1	111.25 (12)
C12—C13—H13A	109.4	Cl3—C29—Cl1	110.06 (12)
N2—C13—H13B	109.4	Cl2—C29—H29	108.6
C12—C13—H13B	109.4	Cl3—C29—H29	108.6
H13A—C13—H13B	108.0	Cl1—C29—H29	108.6
N2—C14—C11^i	111.47 (15)	C10—N1—C12	111.6 (1)
N2—C14—H14A	109.3	C10—N1—C9	110.2 (1)
C11^i—C14—H14A	109.3	C12—N1—C9	112.3 (1)
N2—C14—H14B	109.3	C13—N2—C14	114.5 (1)
C11^i—C14—H14B	109.3	C13—N2—H2A	108.7 (17)
H14A—C14—H14B	108.0	C14—N2—H2A	105.8 (17)
C16—C15—H15A	109.5	C13—N2—H2B	108.9 (14)
C16—C15—H15B	109.5	C14—N2—H2B	107.6 (14)
H15A—C15—H15B	109.5	H2A—N2—H2B	111 (2)
C16—C15—H15C	109.5	C24—N3—C26	112.6 (2)
H15A—C15—H15C	109.5	C24—N3—C23	111.7 (2)
H15B—C15—H15C	109.5	C26—N3—C23	111.0 (1)
C17—C16—C21	116.93 (16)	C28—N4—C27	114.14 (16)
C17—C16—C15	121.71 (18)	C28—N4—H4A	105.5 (15)
C21—C16—C15	121.36 (18)	C27—N4—H4A	110.4 (16)
C16—C17—C18	122.62 (16)	C28—N4—H4B	112.2 (15)
C16—C17—H17	118.7	C27—N4—H4B	105.4 (14)
C18—C17—H17	118.7	H4A—N4—H4B	109 (2)
C7—C2—C3—C4	−0.6 (3)	O4—C19—C20—C21	177.46 (16)
C1—C2—C3—C4	179.1 (2)	C18—C19—C20—C21	−1.3 (2)
C2—C3—C4—C5	1.2 (3)	O4—C19—C20—C23	2.6 (2)
C2—C3—C4—C8	−178.66 (18)	C18—C19—C20—C23	−176.13 (15)
C3—C4—C5—O2	−179.92 (17)	C19—C20—C21—C16	−0.6 (3)
C8—C4—C5—O2	−0.1 (3)	C23—C20—C21—C16	174.16 (18)
C3—C4—C5—C6	−0.7 (2)	C17—C16—C21—C20	1.4 (3)
C8—C4—C5—C6	179.14 (17)	C15—C16—C21—C20	−177.7 (2)
O2—C5—C6—C7	178.92 (17)	C17—C18—C22—O3	−3.2 (3)
C4—C5—C6—C7	−0.3 (2)	C19—C18—C22—O3	176.4 (2)
O2—C5—C6—C9	−0.9 (3)	C21—C20—C23—N3	126.3 (2)
C4—C5—C6—C9	179.95 (15)	C19—C20—C23—N3	−58.9 (2)
C5—C6—C7—C2	0.9 (3)	N3—C24—C25—C28^ii	−65.6 (2)
C9—C6—C7—C2	−179.37 (17)	N3—C26—C27—N4	−44.0 (2)
C3—C2—C7—C6	−0.4 (3)	C11—C10—N1—C12	−76.9 (2)
C1—C2—C7—C6	179.9 (2)	C11—C10—N1—C9	157.64 (15)
C3—C4—C8—O1	4.0 (3)	C13—C12—N1—C10	167.81 (16)
C5—C4—C8—O1	−175.8 (2)	C13—C12—N1—C9	−67.9 (2)
C7—C6—C9—N1	111.7 (2)	C6—C9—N1—C10	−77.51 (18)
C5—C6—C9—N1	−68.5 (2)	C6—C9—N1—C12	157.37 (15)
N1—C10—C11—C14^i	−64.3 (2)	C12—C13—N2—C14	−177.72 (16)
N1—C12—C13—N2	−41.9 (2)	C11^i—C14—N2—C13	−177.52 (16)
C21—C16—C17—C18	−0.4 (3)	C25—C24—N3—C26	−79.6 (2)
C15—C16—C17—C18	178.7 (2)	C25—C24—N3—C23	154.77 (17)
C16—C17—C18—C19	−1.5 (3)	C27—C26—N3—C24	165.67 (16)
C16—C17—C18—C22	178.06 (18)	C27—C26—N3—C23	−68.4 (2)
C17—C18—C19—O4	−176.47 (16)	C20—C23—N3—C24	−72.1 (2)
C22—C18—C19—O4	4.0 (3)	C20—C23—N3—C26	161.39 (16)
C17—C18—C19—C20	2.3 (2)	C25^ii—C28—N4—C27	−171.55 (16)
C22—C18—C19—C20	−177.30 (16)	C26—C27—N4—C28	−179.16 (16)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.90 (2)	1.71 (2)	2.605 (2)	169 (2)
N2—H2B···N1^i	0.90 (2)	2.26 (2)	2.909 (2)	128 (2)
N4—H4A···O4	0.90 (2)	1.85 (2)	2.741 (2)	171 (2)
N4—H4B···O4^ii	0.90 (2)	2.01 (2)	2.883 (2)	163 (2)
N4—H4B···N3^ii	0.90 (2)	2.47 (2)	2.984 (2)	117 (2)
C8—H8···O2	0.93	2.46	2.808 (3)	102
C11—H11A···O2^i	0.97	2.50	3.231 (3)	133
C14—H14B···O4^iii	0.97	2.59	3.557 (3)	172
C22—H22···O4	0.93	2.49	2.828 (3)	102
C26—H26A···O4^ii	0.97	2.56	3.213 (2)	125
C27—H27B···O1^ii	0.97	2.39	3.317 (3)	161
C29—H29···O1^i	0.98	2.46	3.326 (3)	148
C13—H13A···Cg1^iii	0.97	2.58	3.483 (2)	154

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