2,6-Di-tert-butyl-4-{[N-(4,6-dichloro-1,3,5-triazin-2-­yl)propyl­amino]meth­yl}phenol

The title compound, C₂₁H₃₀Cl₂N₄O, contains a sterically hindered phenol group. The dihedral angle between the two rings is 72.3 (1)°. The propyl chain is disordered over two orientations.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.050
• wR factor = 0.149
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C11
PLAT420_ALERT_2_B D-H Without Acceptor       O1     -   H1     ...          ?

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.73 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1     -   H1     ...       1.02 Ang.
PLAT395_ALERT_2_C Deviating  X-O-Y  Angle from 120 Deg for      O1     140.50 Deg.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H16B    ..       1.92 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.20 Deg.
              C20  -C19  -C20'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.00 Deg.
              H19A -C19  -H19C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      19.20 Deg.
              H19B -C19  -H19D    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  12 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
  10 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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

2,6-Di-tert-butyl-4-{[N-(4,6-dichloro-1,3,5-triazin-2- yl)propylamino]methyl}phenol

Crystal data

C21H30Cl2N4O	F(000) = 904
Mr = 425.39	Dx = 1.200 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2871 reflections
a = 9.9134 (17) Å	θ = 2.3–21.7°
b = 19.373 (3) Å	µ = 0.29 mm^−1
c = 12.378 (2) Å	T = 294 K
β = 98.037 (3)°	Block, colourless
V = 2353.9 (7) Å^3	0.54 × 0.40 × 0.38 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	4796 independent reflections
Radiation source: fine-focus sealed tube	2364 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.840, Tmax = 0.895	k = −24→14
13049 measured reflections	l = −15→15

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) = 0.150	w = 1/[σ^2(Fo^2) + (0.0569P)^2 + 0.7546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4796 reflections	Δρmax = 0.25 e Å^−3
281 parameters	Δρmin = −0.26 e Å^−3
30 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: 0.0197 (15)

Special details

Experimental. ¹H NMR (C_DCl₃, δ, p.p.m.): 0.93 (t, 3H), 1.43 (s, 18H), 1.64 (t, 2H), 3.54 (t, 2H), 4.69 (s, 2H), 5.21 (s, 1H), 7.13 (s, 2H) ¹³C NMR (C_DCl₃, δ, p.p.m.):11.32 (1 C), 20.25 (1 C), 30.31 (6 C), 34.38 (2 C), 48.99 (1 C), 51.11 (1 C), 125.40 (2 C), 126.56 (1 C), 136.29 (2 C), 153.72 (1 C), 164.82 (1 C), 170.16 (2 C)

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)
Cl1	−0.41617 (8)	0.16672 (5)	0.63713 (7)	0.0813 (3)
Cl2	0.02511 (12)	0.21933 (8)	0.89709 (8)	0.1280 (5)
N1	−0.1936 (2)	0.20394 (11)	0.56797 (18)	0.0541 (6)
N2	−0.1894 (3)	0.19283 (13)	0.7601 (2)	0.0710 (7)
N3	0.0105 (2)	0.22911 (13)	0.6891 (2)	0.0663 (7)
N4	0.0016 (2)	0.24067 (11)	0.50302 (19)	0.0575 (6)
O1	−0.00452 (19)	−0.03721 (10)	0.23344 (18)	0.0731 (6)
H1	0.0057	−0.0866	0.2616	0.110*
C1	−0.0616 (3)	0.22433 (13)	0.5871 (2)	0.0537 (7)
C2	−0.2466 (3)	0.19023 (13)	0.6565 (2)	0.0573 (7)
C3	−0.0597 (4)	0.21300 (17)	0.7662 (3)	0.0718 (9)
C4	−0.0672 (3)	0.23323 (13)	0.3895 (2)	0.0608 (8)
H4A	−0.0293	0.2664	0.3434	0.073*
H4B	−0.1634	0.2435	0.3873	0.073*
C5	−0.0515 (3)	0.16141 (13)	0.3453 (2)	0.0483 (7)
C6	0.0578 (3)	0.14440 (14)	0.2922 (2)	0.0515 (7)
H6	0.1202	0.1787	0.2815	0.062*
C7	0.0783 (2)	0.07862 (13)	0.2546 (2)	0.0474 (6)
C8	−0.0192 (2)	0.02879 (13)	0.2704 (2)	0.0476 (6)
C9	−0.1321 (2)	0.04329 (13)	0.3237 (2)	0.0446 (6)
C10	−0.1450 (3)	0.11031 (13)	0.3592 (2)	0.0482 (7)
H10	−0.2195	0.1215	0.3938	0.058*
C11	0.2028 (3)	0.06184 (14)	0.1965 (2)	0.0570 (7)
C12	0.2873 (3)	0.00331 (19)	0.2537 (3)	0.0923 (11)
H12A	0.3631	−0.0063	0.2156	0.138*
H12B	0.2317	−0.0372	0.2542	0.138*
H12C	0.3202	0.0166	0.3274	0.138*
C13	0.2963 (4)	0.12395 (19)	0.1960 (4)	0.1218 (17)
H13A	0.3737	0.1118	0.1613	0.183*
H13B	0.3265	0.1382	0.2696	0.183*
H13C	0.2477	0.1611	0.1566	0.183*
C14	0.1564 (4)	0.0417 (2)	0.0775 (3)	0.1063 (13)
H14A	0.1015	0.0780	0.0416	0.159*
H14B	0.1039	−0.0001	0.0751	0.159*
H14C	0.2348	0.0344	0.0413	0.159*
C15	−0.2361 (3)	−0.01282 (14)	0.3450 (2)	0.0557 (7)
C16	−0.1650 (3)	−0.06927 (17)	0.4181 (3)	0.0861 (10)
H16A	−0.1219	−0.0492	0.4851	0.129*
H16B	−0.0974	−0.0913	0.3815	0.129*
H16C	−0.2308	−0.1028	0.4338	0.129*
C17	−0.3064 (3)	−0.04357 (19)	0.2367 (3)	0.0892 (11)
H17A	−0.3756	−0.0755	0.2513	0.134*
H17B	−0.2402	−0.0672	0.2006	0.134*
H17C	−0.3472	−0.0071	0.1907	0.134*
C18	−0.3487 (3)	0.01714 (17)	0.4041 (3)	0.0787 (10)
H18A	−0.3092	0.0356	0.4733	0.118*
H18B	−0.4123	−0.0186	0.4153	0.118*
H18C	−0.3952	0.0532	0.3606	0.118*
C19	0.1436 (3)	0.26413 (15)	0.5199 (3)	0.0757 (9)
H19A	0.1794	0.2602	0.4520	0.091*	0.603 (7)
H19B	0.1944	0.2332	0.5708	0.091*	0.603 (7)
H19C	0.1898	0.2493	0.4607	0.091*	0.397 (7)
H19D	0.1905	0.2457	0.5868	0.091*	0.397 (7)
C20	0.1699 (10)	0.3379 (4)	0.5625 (7)	0.089 (3)	0.603 (7)
H20A	0.1435	0.3418	0.6348	0.106*	0.603 (7)
H20B	0.2663	0.3484	0.5678	0.106*	0.603 (7)
C21	0.0893 (8)	0.3884 (3)	0.4865 (6)	0.114 (3)	0.603 (7)
H21A	0.1172	0.3851	0.4155	0.171*	0.603 (7)
H21B	0.1053	0.4344	0.5142	0.171*	0.603 (7)
H21C	−0.0060	0.3779	0.4815	0.171*	0.603 (7)
C20'	0.1392 (11)	0.3434 (4)	0.5241 (13)	0.080 (4)	0.397 (7)
H20C	0.0926	0.3614	0.4557	0.096*	0.397 (7)
H20D	0.0900	0.3583	0.5824	0.096*	0.397 (7)
C21'	0.2822 (9)	0.3702 (4)	0.5435 (8)	0.099 (4)	0.397 (7)
H21D	0.3345	0.3435	0.5999	0.148*	0.397 (7)
H21E	0.2815	0.4177	0.5657	0.148*	0.397 (7)
H21F	0.3223	0.3666	0.4775	0.148*	0.397 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0729 (6)	0.0918 (6)	0.0841 (6)	−0.0152 (4)	0.0278 (4)	0.0025 (5)
Cl2	0.1245 (9)	0.1910 (13)	0.0628 (6)	−0.0163 (8)	−0.0066 (6)	−0.0089 (7)
N1	0.0608 (15)	0.0492 (13)	0.0552 (14)	0.0001 (11)	0.0181 (12)	−0.0011 (11)
N2	0.088 (2)	0.0758 (18)	0.0521 (16)	−0.0078 (15)	0.0189 (14)	0.0010 (13)
N3	0.0678 (16)	0.0675 (17)	0.0648 (17)	0.0009 (13)	0.0133 (14)	−0.0104 (14)
N4	0.0683 (15)	0.0499 (13)	0.0590 (15)	−0.0065 (12)	0.0250 (12)	−0.0075 (12)
O1	0.0708 (13)	0.0429 (11)	0.1101 (17)	−0.0066 (9)	0.0286 (12)	−0.0183 (11)
C1	0.0635 (19)	0.0404 (15)	0.0607 (19)	0.0021 (13)	0.0205 (16)	−0.0062 (14)
C2	0.0700 (19)	0.0459 (16)	0.0600 (19)	−0.0018 (14)	0.0229 (16)	−0.0013 (14)
C3	0.082 (2)	0.074 (2)	0.060 (2)	−0.0009 (18)	0.0095 (18)	−0.0053 (17)
C4	0.077 (2)	0.0482 (17)	0.0627 (19)	0.0037 (14)	0.0300 (16)	0.0063 (14)
C5	0.0553 (16)	0.0444 (15)	0.0471 (15)	0.0025 (13)	0.0135 (13)	0.0019 (12)
C6	0.0557 (16)	0.0454 (16)	0.0569 (17)	−0.0042 (13)	0.0201 (13)	0.0019 (13)
C7	0.0436 (15)	0.0479 (16)	0.0519 (16)	0.0023 (12)	0.0110 (12)	−0.0001 (13)
C8	0.0454 (15)	0.0426 (15)	0.0544 (16)	−0.0011 (12)	0.0054 (13)	−0.0036 (13)
C9	0.0405 (14)	0.0477 (15)	0.0450 (15)	−0.0019 (12)	0.0032 (12)	0.0017 (12)
C10	0.0444 (15)	0.0572 (17)	0.0445 (15)	0.0021 (13)	0.0109 (12)	0.0019 (13)
C11	0.0529 (16)	0.0536 (17)	0.068 (2)	−0.0009 (14)	0.0205 (14)	−0.0032 (15)
C12	0.056 (2)	0.095 (3)	0.127 (3)	0.0140 (19)	0.015 (2)	0.009 (2)
C13	0.107 (3)	0.082 (3)	0.201 (5)	−0.024 (2)	0.107 (3)	−0.029 (3)
C14	0.107 (3)	0.141 (4)	0.077 (3)	0.017 (3)	0.032 (2)	−0.014 (2)
C15	0.0489 (16)	0.0584 (17)	0.0601 (18)	−0.0121 (13)	0.0082 (14)	−0.0007 (15)
C16	0.087 (2)	0.069 (2)	0.104 (3)	−0.0099 (18)	0.017 (2)	0.025 (2)
C17	0.074 (2)	0.114 (3)	0.080 (2)	−0.043 (2)	0.0121 (18)	−0.022 (2)
C18	0.0605 (19)	0.086 (2)	0.095 (2)	−0.0223 (17)	0.0302 (18)	−0.003 (2)
C19	0.071 (2)	0.069 (2)	0.094 (2)	−0.0111 (17)	0.0353 (18)	−0.0155 (19)
C20	0.088 (6)	0.094 (5)	0.085 (6)	−0.035 (4)	0.017 (5)	−0.016 (4)
C21	0.151 (6)	0.081 (5)	0.113 (5)	−0.024 (4)	0.028 (5)	0.001 (4)
C20'	0.062 (6)	0.077 (7)	0.093 (9)	−0.001 (5)	−0.013 (5)	0.009 (6)
C21'	0.101 (7)	0.100 (6)	0.099 (6)	−0.036 (5)	0.025 (5)	−0.007 (5)

Geometric parameters (Å, º)

Cl1—C2	1.726 (3)	C13—H13C	0.9600
Cl2—C3	1.722 (3)	C14—H14A	0.9600
N1—C2	1.307 (3)	C14—H14B	0.9600
N1—C1	1.356 (3)	C14—H14C	0.9600
N2—C2	1.328 (4)	C15—C16	1.528 (4)
N2—C3	1.336 (4)	C15—C18	1.532 (4)
N3—C3	1.296 (4)	C15—C17	1.542 (4)
N3—C1	1.364 (4)	C16—H16A	0.9600
N4—C1	1.326 (3)	C16—H16B	0.9600
N4—C19	1.466 (4)	C16—H16C	0.9600
N4—C4	1.480 (4)	C17—H17A	0.9600
O1—C8	1.373 (3)	C17—H17B	0.9600
O1—H1	1.0190	C17—H17C	0.9600
C4—C5	1.512 (4)	C18—H18A	0.9600
C4—H4A	0.9700	C18—H18B	0.9600
C4—H4B	0.9700	C18—H18C	0.9600
C5—C6	1.383 (3)	C19—C20	1.533 (7)
C5—C10	1.383 (3)	C19—C20'	1.538 (8)
C6—C7	1.382 (3)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9599
C7—C8	1.399 (3)	C19—H19C	0.9600
C7—C11	1.547 (3)	C19—H19D	0.9600
C8—C9	1.405 (3)	C20—C21	1.508 (8)
C9—C10	1.382 (3)	C20—H20A	0.9700
C9—C15	1.546 (3)	C20—H20B	0.9700
C10—H10	0.9300	C21—H21A	0.9600
C11—C13	1.519 (4)	C21—H21B	0.9600
C11—C12	1.524 (4)	C21—H21C	0.9600
C11—C14	1.531 (4)	C20'—C21'	1.497 (9)
C12—H12A	0.9600	C20'—H20C	0.9700
C12—H12B	0.9600	C20'—H20D	0.9700
C12—H12C	0.9600	C21'—H21D	0.9600
C13—H13A	0.9600	C21'—H21E	0.9600
C13—H13B	0.9600	C21'—H21F	0.9600
C2—N1—C1	113.8 (2)	C16—C15—C18	107.2 (3)
C2—N2—C3	110.1 (2)	C16—C15—C17	110.7 (3)
C3—N3—C1	113.6 (3)	C18—C15—C17	106.9 (2)
C1—N4—C19	120.8 (3)	C16—C15—C9	109.9 (2)
C1—N4—C4	121.1 (2)	C18—C15—C9	111.3 (2)
C19—N4—C4	118.1 (2)	C17—C15—C9	110.8 (2)
C8—O1—H1	140.5	C15—C16—H16A	109.5
N4—C1—N1	118.9 (3)	C15—C16—H16B	109.5
N4—C1—N3	117.8 (3)	H16A—C16—H16B	109.5
N1—C1—N3	123.3 (2)	C15—C16—H16C	109.5
N1—C2—N2	129.4 (3)	H16A—C16—H16C	109.5
N1—C2—Cl1	115.8 (2)	H16B—C16—H16C	109.5
N2—C2—Cl1	114.8 (2)	C15—C17—H17A	109.5
N3—C3—N2	129.8 (3)	C15—C17—H17B	109.5
N3—C3—Cl2	115.7 (3)	H17A—C17—H17B	109.5
N2—C3—Cl2	114.5 (3)	C15—C17—H17C	109.5
N4—C4—C5	112.1 (2)	H17A—C17—H17C	109.5
N4—C4—H4A	109.2	H17B—C17—H17C	109.5
C5—C4—H4A	109.2	C15—C18—H18A	109.5
N4—C4—H4B	109.2	C15—C18—H18B	109.5
C5—C4—H4B	109.2	H18A—C18—H18B	109.5
H4A—C4—H4B	107.9	C15—C18—H18C	109.5
C6—C5—C10	118.1 (2)	H18A—C18—H18C	109.5
C6—C5—C4	121.3 (2)	H18B—C18—H18C	109.5
C10—C5—C4	120.6 (2)	N4—C19—C20	116.8 (4)
C7—C6—C5	122.8 (2)	N4—C19—C20'	106.4 (5)
C7—C6—H6	118.6	C20—C19—C20'	20.2 (6)
C5—C6—H6	118.6	N4—C19—H19A	108.4
C6—C7—C8	116.9 (2)	C20—C19—H19A	108.1
C6—C7—C11	121.0 (2)	C20'—C19—H19A	97.2
C8—C7—C11	122.1 (2)	N4—C19—H19B	107.7
O1—C8—C7	119.2 (2)	C20—C19—H19B	107.9
O1—C8—C9	118.1 (2)	C20'—C19—H19B	128.1
C7—C8—C9	122.6 (2)	H19A—C19—H19B	107.5
C10—C9—C8	116.9 (2)	N4—C19—H19C	110.5
C10—C9—C15	120.9 (2)	C20—C19—H19C	117.7
C8—C9—C15	122.3 (2)	C20'—C19—H19C	110.0
C9—C10—C5	122.7 (2)	H19A—C19—H19C	15.0
C9—C10—H10	118.7	H19B—C19—H19C	93.0
C5—C10—H10	118.7	N4—C19—H19D	110.3
C13—C11—C12	107.2 (3)	C20—C19—H19D	90.6
C13—C11—C14	107.4 (3)	C20'—C19—H19D	110.8
C12—C11—C14	109.2 (3)	H19A—C19—H19D	122.2
C13—C11—C7	111.2 (2)	H19B—C19—H19D	19.2
C12—C11—C7	111.3 (2)	H19C—C19—H19D	108.8
C14—C11—C7	110.4 (2)	C21—C20—C19	109.9 (6)
C11—C12—H12A	109.5	C21—C20—H20A	109.7
C11—C12—H12B	109.5	C19—C20—H20A	109.7
H12A—C12—H12B	109.5	C21—C20—H20B	109.7
C11—C12—H12C	109.5	C19—C20—H20B	109.7
H12A—C12—H12C	109.5	H20A—C20—H20B	108.2
H12B—C12—H12C	109.5	C21'—C20'—C19	108.7 (7)
C11—C13—H13A	109.5	C21'—C20'—H20C	109.9
C11—C13—H13B	109.5	C19—C20'—H20C	109.9
H13A—C13—H13B	109.5	C21'—C20'—H20D	109.9
C11—C13—H13C	109.5	C19—C20'—H20D	109.9
H13A—C13—H13C	109.5	H20C—C20'—H20D	108.3
H13B—C13—H13C	109.5	C20'—C21'—H21D	109.5
C11—C14—H14A	109.5	C20'—C21'—H21E	109.5
C11—C14—H14B	109.5	H21D—C21'—H21E	109.5
H14A—C14—H14B	109.5	C20'—C21'—H21F	109.5
C11—C14—H14C	109.5	H21D—C21'—H21F	109.5
H14A—C14—H14C	109.5	H21E—C21'—H21F	109.5
H14B—C14—H14C	109.5
C19—N4—C1—N1	178.9 (2)	O1—C8—C9—C10	−179.4 (2)
C4—N4—C1—N1	−3.4 (4)	C7—C8—C9—C10	1.0 (4)
C19—N4—C1—N3	−1.0 (4)	O1—C8—C9—C15	2.1 (4)
C4—N4—C1—N3	176.7 (2)	C7—C8—C9—C15	−177.4 (2)
C2—N1—C1—N4	−178.9 (2)	C8—C9—C10—C5	−0.9 (4)
C2—N1—C1—N3	1.0 (4)	C15—C9—C10—C5	177.6 (2)
C3—N3—C1—N4	179.2 (3)	C6—C5—C10—C9	1.0 (4)
C3—N3—C1—N1	−0.7 (4)	C4—C5—C10—C9	−177.5 (2)
C1—N1—C2—N2	−0.8 (4)	C6—C7—C11—C13	4.0 (4)
C1—N1—C2—Cl1	177.98 (18)	C8—C7—C11—C13	−176.8 (3)
C3—N2—C2—N1	0.2 (4)	C6—C7—C11—C12	123.4 (3)
C3—N2—C2—Cl1	−178.5 (2)	C8—C7—C11—C12	−57.4 (3)
C1—N3—C3—N2	0.1 (5)	C6—C7—C11—C14	−115.2 (3)
C1—N3—C3—Cl2	−179.1 (2)	C8—C7—C11—C14	64.0 (3)
C2—N2—C3—N3	0.2 (5)	C10—C9—C15—C16	−116.9 (3)
C2—N2—C3—Cl2	179.3 (2)	C8—C9—C15—C16	61.5 (3)
C1—N4—C4—C5	−86.7 (3)	C10—C9—C15—C18	1.7 (3)
C19—N4—C4—C5	91.0 (3)	C8—C9—C15—C18	−179.9 (2)
N4—C4—C5—C6	−89.3 (3)	C10—C9—C15—C17	120.4 (3)
N4—C4—C5—C10	89.1 (3)	C8—C9—C15—C17	−61.1 (3)
C10—C5—C6—C7	−1.1 (4)	C1—N4—C19—C20	−74.6 (5)
C4—C5—C6—C7	177.3 (2)	C4—N4—C19—C20	107.7 (5)
C5—C6—C7—C8	1.2 (4)	C1—N4—C19—C20'	−93.3 (7)
C5—C6—C7—C11	−179.5 (2)	C4—N4—C19—C20'	88.9 (7)
C6—C7—C8—O1	179.2 (2)	N4—C19—C20—C21	−57.1 (8)
C11—C7—C8—O1	0.0 (4)	C20'—C19—C20—C21	6 (2)
C6—C7—C8—C9	−1.2 (4)	N4—C19—C20'—C21'	178.8 (8)
C11—C7—C8—C9	179.6 (2)	C20—C19—C20'—C21'	54.8 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O1	0.96	2.32	2.974 (4)	125
C14—H14B···O1	0.96	2.47	3.077 (4)	121
C16—H16B···O1	0.96	2.40	3.026 (4)	122
C17—H17B···O1	0.96	2.39	3.001 (4)	121