4-[(4-Methyl­phenyl)­diazenyl]-6-methoxy-2-{[tris­(hydroxy­methyl)­methyl]­amino­methyl­ene}cyclo­hexa-3,5-dien-1(2H)-one

The title compound, C₁₉H₂₃N₃O₅, adopts the keto–amine tautomeric form and the configuration around the —N=N— double bond is trans. There is an intramolecular N—H...O hydrogen bond and intermolecular O—H...O interactions, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.071
• wR factor = 0.173
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  C2B    ..  C5B      =       3.01 Ang.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.137
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.14
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.43 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.98 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C1
PLAT301_ALERT_3_C Main Residue  Disorder .........................      16.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

   0 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
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1998).

4-[(4-methylphenyl)diazenyl]-6-methoxy-2-{[tris(hydroxymethyl)methyl] aminomethylene}cyclohexa-3,5-dien-1(2H)-one

Crystal data

C19H23N3O5	F(000) = 792
Mr = 373.40	Dx = 1.249 Mg m^−3
Monoclinic, P21/c	Melting point = 368–370 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.4603 (17) Å	Cell parameters from 6249 reflections
b = 10.7156 (12) Å	θ = 25.8–1.9°
c = 10.6495 (9) Å	µ = 0.09 mm^−1
β = 94.830 (7)°	T = 293 K
V = 1985.4 (3) Å^3	Prism, orange
Z = 4	0.25 × 0.15 × 0.09 mm

Data collection

Stoe IPDS-2 diffractometer	3500 independent reflections
Radiation source: fine-focus sealed tube	1490 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.137
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −20→20
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.983, Tmax = 0.992	l = −12→12
15669 measured 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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.066P)^2] where P = (Fo^2 + 2Fc^2)/3
3500 reflections	(Δ/σ)max = 0.029
289 parameters	Δρmax = 0.19 e Å^−3
82 restraints	Δρmin = −0.26 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	Occ. (<1)
C1	0.5591 (3)	0.4041 (5)	0.3708 (5)	0.0708 (15)
C2A	0.5779 (7)	0.4392 (9)	0.2498 (11)	0.0940 (16)	0.550 (5)
H2A	0.6263	0.4697	0.2355	0.113*	0.550 (5)
C2B	0.5318 (8)	0.5044 (14)	0.2996 (13)	0.0940 (16)	0.450 (5)
H2B	0.5533	0.5826	0.3171	0.113*	0.450 (5)
C3A	0.5192 (7)	0.4255 (9)	0.1516 (12)	0.0940 (16)	0.550 (5)
H3A	0.5283	0.4471	0.0696	0.113*	0.550 (5)
C3B	0.4737 (8)	0.4942 (14)	0.2029 (13)	0.0940 (16)	0.450 (5)
H3B	0.4562	0.5635	0.1563	0.113*	0.450 (5)
C4	0.4430 (3)	0.3768 (6)	0.1785 (6)	0.0884 (18)
C5A	0.4371 (8)	0.3361 (10)	0.2925 (13)	0.0940 (16)	0.550 (5)
H5A	0.3915	0.2970	0.3094	0.113*	0.550 (5)
C5B	0.4623 (8)	0.2811 (15)	0.2486 (14)	0.0940 (16)	0.450 (5)
H5B	0.4373	0.2052	0.2341	0.113*	0.450 (5)
C6A	0.4932 (7)	0.3472 (11)	0.3886 (13)	0.0940 (16)	0.550 (5)
H6A	0.4855	0.3146	0.4674	0.113*	0.550 (5)
C6B	0.5210 (9)	0.2923 (15)	0.3466 (15)	0.0940 (16)	0.450 (5)
H6B	0.5346	0.2231	0.3962	0.113*	0.450 (5)
C7	0.7146 (3)	0.5171 (4)	0.5732 (4)	0.0542 (13)
C8	0.7596 (3)	0.6210 (4)	0.5722 (5)	0.0536 (12)
C9	0.8111 (2)	0.6525 (4)	0.6755 (4)	0.0423 (11)
C10	0.8176 (3)	0.5750 (4)	0.7844 (4)	0.0458 (11)
C11	0.7719 (3)	0.4621 (4)	0.7779 (5)	0.0528 (12)
C12	0.7218 (3)	0.4365 (5)	0.6790 (5)	0.0577 (13)
C13	0.8563 (3)	0.7606 (4)	0.6695 (4)	0.0466 (11)
C14	0.9583 (2)	0.9022 (3)	0.7631 (4)	0.0399 (10)
C15	1.0377 (3)	0.8566 (4)	0.8085 (4)	0.0470 (12)
C16	0.9268 (3)	0.9948 (4)	0.8553 (4)	0.0456 (11)
C17	0.9645 (3)	0.9622 (4)	0.6345 (4)	0.0457 (12)
C18A	0.7608 (7)	0.2633 (13)	0.8724 (14)	0.0940 (16)	0.550 (5)
H18A	0.7731	0.2204	0.9506	0.141*	0.550 (5)
H18B	0.7857	0.2226	0.8066	0.141*	0.550 (5)
H18C	0.7061	0.2619	0.8522	0.141*	0.550 (5)
C18B	0.7331 (9)	0.2913 (16)	0.9046 (18)	0.0940 (16)	0.450 (5)
H18D	0.7495	0.2481	0.9811	0.141*	0.450 (5)
H18E	0.7315	0.2339	0.8351	0.141*	0.450 (5)
H18F	0.6829	0.3257	0.9110	0.141*	0.450 (5)
C19	0.3793 (4)	0.3618 (8)	0.0737 (7)	0.136 (3)
H19A	0.3825	0.2805	0.0367	0.163*
H19B	0.3846	0.4244	0.0106	0.163*
H19C	0.3303	0.3710	0.1076	0.163*
N1	0.6156 (2)	0.4136 (4)	0.4754 (4)	0.0636 (11)
N2	0.6605 (3)	0.5032 (4)	0.4673 (4)	0.0654 (12)
N3	0.9063 (2)	0.7952 (3)	0.7596 (4)	0.0430 (9)
O1	0.86172 (18)	0.6014 (2)	0.8829 (3)	0.0512 (8)
O2	1.03549 (19)	0.7775 (3)	0.9162 (3)	0.0493 (8)
O3	0.9746 (2)	1.1015 (3)	0.8607 (3)	0.0634 (11)
O4	0.9006 (2)	1.0413 (3)	0.5969 (3)	0.0516 (9)
O5	0.7869 (2)	0.3913 (3)	0.8840 (3)	0.0826 (12)
H1	0.913 (2)	0.744 (4)	0.823 (4)	0.044 (12)*
H8	0.754 (2)	0.672 (4)	0.495 (4)	0.053 (13)*
H12	0.689 (3)	0.366 (4)	0.675 (4)	0.073 (15)*
H13	0.852 (3)	0.817 (4)	0.590 (4)	0.064 (14)*
H15A	1.062 (3)	0.808 (4)	0.740 (5)	0.074 (16)*
H15B	1.072 (2)	0.933 (4)	0.835 (4)	0.045 (11)*
H16A	0.927 (2)	0.949 (4)	0.940 (4)	0.051 (12)*
H16B	0.871 (2)	1.012 (3)	0.831 (4)	0.041 (11)*
H17A	1.014 (2)	1.010 (4)	0.642 (3)	0.045 (12)*
H17B	0.975 (2)	0.899 (4)	0.569 (4)	0.057 (13)*
H22	1.060 (3)	0.708 (4)	0.911 (4)	0.058 (15)*
H33	0.972 (3)	1.138 (5)	0.926 (5)	0.08 (2)*
H44	0.877 (3)	1.022 (4)	0.522 (5)	0.075 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.075 (4)	0.068 (3)	0.067 (3)	−0.020 (3)	−0.009 (3)	−0.018 (3)
C2A	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C2B	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C3A	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C3B	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C4	0.063 (4)	0.106 (4)	0.091 (4)	−0.018 (3)	−0.023 (3)	−0.014 (4)
C5A	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C5B	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C6A	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C6B	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C7	0.061 (3)	0.044 (3)	0.055 (3)	−0.008 (2)	−0.012 (3)	−0.004 (2)
C8	0.063 (3)	0.050 (3)	0.045 (3)	−0.008 (2)	−0.010 (2)	0.003 (2)
C9	0.047 (3)	0.036 (2)	0.043 (3)	−0.003 (2)	−0.003 (2)	0.003 (2)
C10	0.047 (3)	0.043 (2)	0.047 (3)	0.001 (2)	−0.001 (2)	0.000 (2)
C11	0.056 (3)	0.045 (3)	0.057 (3)	−0.011 (2)	0.002 (3)	0.011 (2)
C12	0.057 (3)	0.050 (3)	0.064 (3)	−0.013 (3)	−0.003 (3)	−0.001 (3)
C13	0.053 (3)	0.038 (2)	0.047 (3)	−0.002 (2)	−0.005 (2)	0.003 (2)
C14	0.052 (3)	0.033 (2)	0.033 (2)	−0.006 (2)	−0.001 (2)	−0.0046 (18)
C15	0.059 (3)	0.037 (2)	0.044 (3)	−0.004 (2)	0.000 (2)	0.002 (2)
C16	0.056 (3)	0.037 (2)	0.044 (3)	0.001 (2)	0.004 (2)	−0.001 (2)
C17	0.060 (3)	0.042 (2)	0.035 (3)	−0.004 (2)	0.004 (2)	0.000 (2)
C18A	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C18B	0.085 (4)	0.095 (3)	0.098 (4)	−0.026 (3)	−0.016 (3)	−0.003 (3)
C19	0.087 (5)	0.199 (8)	0.113 (6)	−0.020 (5)	−0.038 (5)	−0.051 (6)
N1	0.060 (3)	0.062 (3)	0.069 (3)	−0.003 (2)	−0.002 (2)	−0.007 (2)
N2	0.067 (3)	0.057 (2)	0.070 (3)	−0.016 (2)	−0.014 (2)	−0.006 (2)
N3	0.053 (2)	0.0374 (19)	0.037 (2)	−0.0070 (17)	−0.0059 (19)	0.0045 (18)
O1	0.060 (2)	0.0484 (18)	0.0440 (18)	−0.0063 (15)	−0.0037 (16)	0.0063 (14)
O2	0.067 (2)	0.0367 (17)	0.0427 (18)	0.0092 (16)	−0.0025 (15)	−0.0022 (15)
O3	0.103 (3)	0.0393 (18)	0.049 (2)	−0.0171 (18)	0.009 (2)	−0.0093 (17)
O4	0.073 (2)	0.0424 (17)	0.0369 (18)	−0.0009 (16)	−0.0074 (17)	0.0009 (15)
O5	0.103 (3)	0.067 (2)	0.073 (3)	−0.039 (2)	−0.016 (2)	0.0298 (19)

Geometric parameters (Å, º)

C1—C6A	1.330 (13)	C12—H12	0.95 (5)
C1—C2B	1.377 (15)	C13—N3	1.296 (5)
C1—C6B	1.384 (15)	C13—H13	1.04 (5)
C1—C2A	1.407 (13)	C14—N3	1.460 (5)
C1—N1	1.429 (6)	C14—C15	1.512 (6)
C2A—C3A	1.410 (14)	C14—C17	1.525 (6)
C2A—H2A	0.9300	C14—C16	1.530 (6)
C2B—C3B	1.388 (17)	C15—O2	1.430 (5)
C2B—H2B	0.9300	C15—H15A	1.02 (5)
C3A—C4	1.480 (12)	C15—H15B	1.04 (4)
C3A—H3A	0.9300	C16—O3	1.414 (5)
C3B—C4	1.384 (14)	C16—H16A	1.03 (4)
C3B—H3B	0.9300	C16—H16B	1.01 (4)
C4—C5B	1.296 (16)	C17—O4	1.431 (5)
C4—C5A	1.302 (14)	C17—H17A	1.00 (4)
C4—C19	1.516 (8)	C17—H17B	1.00 (4)
C5A—C6A	1.362 (15)	C18A—O5	1.448 (14)
C5A—H5A	0.9300	C18A—H18A	0.9600
C5B—C6B	1.405 (19)	C18A—H18B	0.9600
C5B—H5B	0.9300	C18A—H18C	0.9600
C6A—H6A	0.9300	C18B—O5	1.453 (16)
C6B—H6B	0.9300	C18B—H18D	0.9600
C7—C8	1.363 (6)	C18B—H18E	0.9600
C7—N2	1.417 (5)	C18B—H18F	0.9600
C7—C12	1.417 (6)	C19—H19A	0.9600
C8—C9	1.402 (6)	C19—H19B	0.9600
C8—H8	0.98 (4)	C19—H19C	0.9600
C9—C13	1.406 (6)	N1—N2	1.247 (5)
C9—C10	1.424 (6)	N3—H1	0.87 (4)
C10—O1	1.279 (5)	O2—H22	0.87 (5)
C10—C11	1.447 (6)	O3—H33	0.80 (6)
C11—C12	1.340 (6)	O4—H44	0.90 (5)
C11—O5	1.368 (5)
C6A—C1—C2B	100.0 (9)	C11—C12—H12	123 (3)
C2B—C1—C6B	115.7 (10)	C7—C12—H12	116 (3)
C6A—C1—C2A	121.6 (9)	N3—C13—C9	123.3 (4)
C2B—C1—C2A	52.0 (6)	N3—C13—H13	116 (2)
C6B—C1—C2A	101.9 (8)	C9—C13—H13	121 (2)
C6A—C1—N1	118.0 (7)	N3—C14—C15	107.8 (3)
C2B—C1—N1	123.9 (7)	N3—C14—C17	113.5 (4)
C6B—C1—N1	119.8 (8)	C15—C14—C17	106.9 (4)
C2A—C1—N1	119.7 (6)	N3—C14—C16	105.6 (4)
C1—C2A—C3A	116.1 (10)	C15—C14—C16	112.0 (4)
C1—C2A—H2A	121.9	C17—C14—C16	111.1 (3)
C3A—C2A—H2A	121.9	O2—C15—C14	111.2 (4)
C1—C2B—C3B	123.0 (12)	O2—C15—H15A	108 (3)
C1—C2B—H2B	118.5	C14—C15—H15A	111 (3)
C3B—C2B—H2B	118.5	O2—C15—H15B	108 (2)
C2A—C3A—C4	120.2 (11)	C14—C15—H15B	109 (2)
C2A—C3A—H3A	119.9	H15A—C15—H15B	109 (3)
C4—C3A—H3A	119.9	O3—C16—C14	107.9 (4)
C4—C3B—C2B	117.3 (13)	O3—C16—H16A	113 (2)
C4—C3B—H3B	121.4	C14—C16—H16A	106 (2)
C2B—C3B—H3B	121.4	O3—C16—H16B	115 (2)
C5B—C4—C3B	122.2 (10)	C14—C16—H16B	110 (2)
C5A—C4—C3B	100.9 (8)	H16A—C16—H16B	104 (3)
C5B—C4—C3A	101.3 (9)	O4—C17—C14	112.9 (4)
C5A—C4—C3A	116.2 (9)	O4—C17—H17A	111 (2)
C3B—C4—C3A	51.3 (6)	C14—C17—H17A	106 (2)
C5B—C4—C19	118.7 (8)	O4—C17—H17B	113 (2)
C5A—C4—C19	122.7 (8)	C14—C17—H17B	112 (2)
C3B—C4—C19	118.9 (9)	H17A—C17—H17B	101 (3)
C3A—C4—C19	120.7 (7)	O5—C18A—H18A	109.5
C4—C5A—C6A	124.3 (12)	O5—C18A—H18B	109.5
C4—C5A—H5A	117.9	H18A—C18A—H18B	109.5
C6A—C5A—H5A	117.9	O5—C18A—H18C	109.5
C4—C5B—C6B	119.9 (13)	H18A—C18A—H18C	109.5
C4—C5B—H5B	120.0	H18B—C18A—H18C	109.5
C6B—C5B—H5B	120.0	O5—C18B—H18D	109.5
C1—C6A—C5A	120.6 (12)	O5—C18B—H18E	109.5
C1—C6A—H6A	119.7	H18D—C18B—H18E	109.5
C5A—C6A—H6A	119.7	O5—C18B—H18F	109.5
C1—C6B—C5B	121.4 (14)	H18D—C18B—H18F	109.5
C1—C6B—H6B	119.3	H18E—C18B—H18F	109.5
C5B—C6B—H6B	119.3	C4—C19—H19A	109.5
C8—C7—N2	115.2 (4)	C4—C19—H19B	109.5
C8—C7—C12	119.4 (4)	H19A—C19—H19B	109.5
N2—C7—C12	125.3 (4)	C4—C19—H19C	109.5
C7—C8—C9	121.6 (5)	H19A—C19—H19C	109.5
C7—C8—H8	116 (2)	H19B—C19—H19C	109.5
C9—C8—H8	122 (2)	N2—N1—C1	113.4 (4)
C8—C9—C13	119.3 (4)	N1—N2—C7	114.0 (4)
C8—C9—C10	120.0 (4)	C13—N3—C14	128.4 (4)
C13—C9—C10	120.7 (4)	C13—N3—H1	116 (3)
O1—C10—C9	122.7 (4)	C14—N3—H1	115 (3)
O1—C10—C11	121.0 (4)	C15—O2—H22	114 (3)
C9—C10—C11	116.3 (4)	C16—O3—H33	110 (4)
C12—C11—O5	127.1 (4)	C17—O4—H44	114 (3)
C12—C11—C10	121.9 (4)	C11—O5—C18A	114.7 (7)
O5—C11—C10	110.9 (4)	C11—O5—C18B	116.9 (8)
C11—C12—C7	120.6 (5)
C6A—C1—C2A—C3A	8.0 (12)	C7—C8—C9—C10	0.4 (7)
C2B—C1—C2A—C3A	−69.1 (10)	C8—C9—C10—O1	−177.6 (4)
C6B—C1—C2A—C3A	44.4 (10)	C13—C9—C10—O1	2.8 (7)
N1—C1—C2A—C3A	179.2 (6)	C8—C9—C10—C11	3.2 (6)
C6A—C1—C2B—C3B	−42.2 (11)	C13—C9—C10—C11	−176.4 (4)
C6B—C1—C2B—C3B	−4.7 (14)	O1—C10—C11—C12	175.8 (5)
C2A—C1—C2B—C3B	80.4 (11)	C9—C10—C11—C12	−5.0 (7)
N1—C1—C2B—C3B	−176.2 (7)	O1—C10—C11—O5	−3.4 (6)
C1—C2A—C3A—C4	0.1 (10)	C9—C10—C11—O5	175.8 (4)
C1—C2B—C3B—C4	−0.2 (11)	O5—C11—C12—C7	−177.7 (5)
C2B—C3B—C4—C5B	5.6 (13)	C10—C11—C12—C7	3.3 (8)
C2B—C3B—C4—C5A	42.6 (10)	C8—C7—C12—C11	0.5 (8)
C2B—C3B—C4—C3A	−72.3 (10)	N2—C7—C12—C11	−176.0 (5)
C2B—C3B—C4—C19	179.9 (7)	C8—C9—C13—N3	−178.6 (4)
C2A—C3A—C4—C5B	−46.7 (10)	C10—C9—C13—N3	1.0 (7)
C2A—C3A—C4—C5A	−7.1 (11)	N3—C14—C15—O2	−46.1 (5)
C2A—C3A—C4—C3B	75.7 (11)	C17—C14—C15—O2	−168.5 (3)
C2A—C3A—C4—C19	179.9 (6)	C16—C14—C15—O2	69.6 (4)
C5B—C4—C5A—C6A	82.5 (18)	N3—C14—C16—O3	−179.2 (4)
C3B—C4—C5A—C6A	−45.3 (13)	C15—C14—C16—O3	63.8 (5)
C3A—C4—C5A—C6A	6.7 (14)	C17—C14—C16—O3	−55.7 (5)
C19—C4—C5A—C6A	179.5 (9)	N3—C14—C17—O4	78.8 (5)
C5A—C4—C5B—C6B	−72.0 (16)	C15—C14—C17—O4	−162.5 (3)
C3B—C4—C5B—C6B	−5.6 (17)	C16—C14—C17—O4	−40.1 (5)
C3A—C4—C5B—C6B	45.5 (13)	C6A—C1—N1—N2	−154.7 (7)
C19—C4—C5B—C6B	−179.9 (10)	C2B—C1—N1—N2	−28.2 (9)
C2B—C1—C6A—C5A	42.2 (13)	C6B—C1—N1—N2	160.6 (9)
C6B—C1—C6A—C5A	−76.8 (17)	C2A—C1—N1—N2	33.7 (8)
C2A—C1—C6A—C5A	−9.1 (15)	C1—N1—N2—C7	177.2 (4)
N1—C1—C6A—C5A	179.6 (8)	C8—C7—N2—N1	−174.2 (5)
C4—C5A—C6A—C1	1.1 (17)	C12—C7—N2—N1	2.5 (7)
C6A—C1—C6B—C5B	77.8 (18)	C9—C13—N3—C14	177.7 (4)
C2B—C1—C6B—C5B	4.8 (17)	C15—C14—N3—C13	−131.9 (5)
C2A—C1—C6B—C5B	−48.5 (14)	C17—C14—N3—C13	−13.6 (6)
N1—C1—C6B—C5B	176.6 (9)	C16—C14—N3—C13	108.3 (5)
C4—C5B—C6B—C1	0.2 (19)	C12—C11—O5—C18A	17.0 (9)
N2—C7—C8—C9	174.5 (4)	C10—C11—O5—C18A	−163.9 (7)
C12—C7—C8—C9	−2.4 (8)	C12—C11—O5—C18B	−13.2 (11)
C7—C8—C9—C13	179.9 (5)	C10—C11—O5—C18B	165.9 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O1	0.87 (4)	1.91 (4)	2.611 (4)	136 (4)
O2—H22···O4^i	0.87 (5)	1.92 (5)	2.774 (4)	171 (4)
O3—H33···O2^ii	0.80 (6)	1.92 (6)	2.726 (5)	179 (6)
O4—H44···O1^iii	0.90 (5)	1.98 (5)	2.780 (4)	148 (4)
O4—H44···O5^iii	0.90 (5)	2.26 (5)	2.973 (5)	136 (4)

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