2-Chloro-6-methyl-8,9-di­phenyl­imidazo­[1,2-c]­quinazoline

The title compound, C₂₃H₁₆ClN₃, has been synthesized by the reaction of 4,5-di­phenyl-2-(2-nitro-5-chloro­phenyl)­imidazole with triethyl ortho-acetate, induced by a low-valent titanium reagent. There are two independent mol­ecules of similar conformation in the asymmetric unit. The dihedral angles between the pyrimidine and imidazole rings are 2.14 (2) and 2.71 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.087
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.795

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-chloro-6-methyl-8,9-diphenylimidazo[1,2-c]quinazoline

Crystal data

C23H16ClN3	F(000) = 1536
Mr = 369.84	Dx = 1.367 Mg m^−3
Monoclinic, P21/c	Melting point = 452–453 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.789 (1) Å	Cell parameters from 35 reflections
b = 17.777 (2) Å	θ = 2.9–14.9°
c = 26.040 (3) Å	µ = 0.23 mm^−1
β = 94.70 (1)°	T = 291 K
V = 3593.7 (9) Å^3	Block, colorless
Z = 8	0.54 × 0.48 × 0.34 mm

Data collection

Siemens P4 diffractometer	3063 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.011
Graphite monochromator	θmax = 25.0°, θmin = 1.4°
ω scans	h = 0→9
Absorption correction: ψ scan (XSCANS; Siemens, 1994)	k = 0→21
Tmin = 0.882, Tmax = 0.926	l = −30→30
7325 measured reflections	3 standard reflections every 97 reflections
6330 independent reflections	intensity decay: 1.9%

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)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0384P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max = 0.001
6330 reflections	Δρmax = 0.14 e Å^−3
490 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (2)

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
Cl	0.31998 (9)	0.76302 (4)	0.53087 (3)	0.0816 (2)
N1	0.3554 (2)	0.46802 (10)	0.42845 (7)	0.0593 (5)
N2	0.6123 (2)	0.50260 (9)	0.39244 (7)	0.0472 (5)
N3	0.7484 (2)	0.61308 (9)	0.40530 (7)	0.0508 (5)
C1	0.3512 (3)	0.53833 (13)	0.45174 (9)	0.0553 (6)
C2	0.2160 (3)	0.55456 (15)	0.48200 (9)	0.0698 (7)
H2	0.1315	0.5186	0.4861	0.084*
C3	0.2067 (3)	0.62306 (15)	0.50567 (9)	0.0721 (8)
H3	0.1162	0.6335	0.5257	0.087*
C4	0.3333 (3)	0.67714 (14)	0.49964 (9)	0.0622 (7)
C5	0.4667 (3)	0.66296 (12)	0.46996 (9)	0.0570 (6)
H5	0.5500	0.6994	0.4659	0.068*
C6	0.4761 (3)	0.59334 (12)	0.44600 (8)	0.0503 (6)
C7	0.6132 (3)	0.57348 (12)	0.41533 (8)	0.0486 (6)
C8	0.4797 (3)	0.45110 (12)	0.40057 (9)	0.0535 (6)
C9	0.7638 (3)	0.49878 (11)	0.36624 (8)	0.0456 (6)
C10	0.8428 (3)	0.56719 (11)	0.37502 (8)	0.0461 (6)
C11	0.8166 (3)	0.43284 (11)	0.33675 (8)	0.0467 (6)
C12	0.7370 (3)	0.41576 (12)	0.28860 (9)	0.0577 (6)
H12	0.6484	0.4463	0.2744	0.069*
C13	0.7875 (3)	0.35397 (13)	0.26133 (9)	0.0662 (7)
H13	0.7325	0.3431	0.2291	0.079*
C14	0.9183 (4)	0.30872 (13)	0.28162 (10)	0.0689 (8)
H14	0.9504	0.2664	0.2637	0.083*
C15	1.0020 (3)	0.32625 (12)	0.32867 (10)	0.0648 (7)
H15	1.0932	0.2964	0.3420	0.078*
C16	0.9519 (3)	0.38774 (12)	0.35632 (8)	0.0545 (6)
H16	1.0092	0.3989	0.3882	0.065*
C17	1.0036 (3)	0.59804 (11)	0.35697 (8)	0.0456 (6)
C18	1.0557 (3)	0.66954 (11)	0.37360 (8)	0.0542 (6)
H18	0.9905	0.6954	0.3962	0.065*
C19	1.2016 (3)	0.70281 (13)	0.35730 (9)	0.0650 (7)
H19	1.2331	0.7508	0.3687	0.078*
C20	1.3003 (3)	0.66521 (14)	0.32439 (10)	0.0696 (8)
H20	1.3992	0.6875	0.3136	0.084*
C21	1.2523 (3)	0.59447 (14)	0.30736 (9)	0.0682 (7)
H21	1.3191	0.5689	0.2850	0.082*
C22	1.1049 (3)	0.56114 (12)	0.32335 (8)	0.0577 (7)
H22	1.0734	0.5134	0.3114	0.069*
C23	0.4808 (3)	0.37564 (12)	0.37614 (9)	0.0691 (7)
H23A	0.3985	0.3438	0.3910	0.083*
H23B	0.5936	0.3540	0.3818	0.083*
H23C	0.4508	0.3804	0.3398	0.083*
Cl'	−0.17754 (10)	0.75994 (4)	0.53180 (3)	0.0955 (3)
N1'	−0.1547 (2)	1.04812 (11)	0.41982 (8)	0.0639 (6)
N2'	0.1019 (2)	1.01240 (9)	0.38499 (7)	0.0482 (5)
N3'	0.2419 (2)	0.90328 (9)	0.40045 (7)	0.0504 (5)
C1'	−0.1554 (3)	0.97976 (14)	0.44558 (9)	0.0571 (6)
C2'	−0.2881 (3)	0.96504 (16)	0.47769 (10)	0.0762 (8)
H2'	−0.3727	1.0011	0.4814	0.091*
C3'	−0.2937 (3)	0.89830 (17)	0.50352 (10)	0.0796 (8)
H3'	−0.3818	0.8891	0.5248	0.096*
C4'	−0.1681 (3)	0.84436 (14)	0.49802 (9)	0.0659 (7)
C5'	−0.0365 (3)	0.85649 (13)	0.46739 (8)	0.0582 (6)
H5'	0.0476	0.8200	0.4642	0.070*
C6'	−0.0307 (3)	0.92476 (13)	0.44098 (8)	0.0513 (6)
C7'	0.1057 (3)	0.94273 (12)	0.40925 (8)	0.0470 (6)
C8'	−0.0326 (3)	1.06344 (12)	0.39091 (9)	0.0572 (6)
C9'	0.2530 (3)	1.01581 (11)	0.35889 (8)	0.0479 (6)
C10'	0.3350 (3)	0.94790 (11)	0.36922 (8)	0.0459 (6)
C11'	0.3074 (3)	1.08175 (11)	0.32978 (8)	0.0469 (6)
C12'	0.2349 (3)	1.09708 (12)	0.28028 (9)	0.0583 (7)
H12'	0.1524	1.0647	0.2647	0.070*
C13'	0.2843 (3)	1.15997 (13)	0.25407 (9)	0.0670 (7)
H13'	0.2340	1.1701	0.2212	0.080*
C14'	0.4069 (3)	1.20746 (13)	0.27636 (10)	0.0648 (7)
H14'	0.4378	1.2504	0.2589	0.078*
C15'	0.4842 (3)	1.19182 (12)	0.32420 (10)	0.0632 (7)
H15'	0.5703	1.2233	0.3388	0.076*
C16'	0.4348 (3)	1.12938 (12)	0.35101 (9)	0.0542 (6)
H16'	0.4877	1.1193	0.3836	0.065*
C17'	0.4972 (3)	0.91750 (11)	0.35208 (8)	0.0459 (6)
C18'	0.5534 (3)	0.84765 (12)	0.37075 (8)	0.0530 (6)
H18'	0.4893	0.8225	0.3940	0.064*
C19'	0.7006 (3)	0.81491 (13)	0.35578 (9)	0.0612 (7)
H19'	0.7344	0.7679	0.3686	0.073*
C20'	0.7987 (3)	0.85157 (14)	0.32182 (9)	0.0664 (7)
H20'	0.8992	0.8298	0.3118	0.080*
C21'	0.7461 (3)	0.92047 (14)	0.30308 (9)	0.0657 (7)
H21'	0.8118	0.9455	0.2802	0.079*
C22'	0.5968 (3)	0.95348 (12)	0.31771 (8)	0.0561 (6)
H22'	0.5629	1.0002	0.3044	0.067*
C23'	−0.0385 (3)	1.13622 (12)	0.36268 (10)	0.0862 (9)
H23D	−0.0674	1.1272	0.3267	0.103*
H23E	0.0721	1.1602	0.3673	0.103*
H23F	−0.1239	1.1682	0.3758	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0740 (6)	0.0977 (5)	0.0741 (5)	0.0230 (4)	0.0122 (4)	−0.0156 (4)
N1	0.0458 (14)	0.0673 (13)	0.0653 (14)	−0.0038 (10)	0.0083 (11)	0.0091 (11)
N2	0.0399 (13)	0.0474 (11)	0.0547 (12)	−0.0008 (9)	0.0062 (10)	0.0049 (9)
N3	0.0457 (13)	0.0493 (11)	0.0585 (12)	0.0013 (10)	0.0114 (10)	0.0004 (9)
C1	0.0477 (17)	0.0670 (16)	0.0514 (15)	0.0014 (13)	0.0060 (13)	0.0075 (12)
C2	0.0515 (18)	0.089 (2)	0.0718 (19)	−0.0037 (14)	0.0199 (15)	0.0097 (15)
C3	0.059 (2)	0.100 (2)	0.0590 (18)	0.0156 (16)	0.0172 (15)	0.0035 (16)
C4	0.0541 (19)	0.0819 (18)	0.0508 (16)	0.0144 (14)	0.0050 (14)	0.0004 (13)
C5	0.0507 (18)	0.0672 (16)	0.0536 (15)	0.0065 (12)	0.0081 (13)	0.0029 (12)
C6	0.0433 (16)	0.0593 (15)	0.0486 (14)	0.0037 (12)	0.0067 (12)	0.0063 (12)
C7	0.0473 (17)	0.0473 (14)	0.0514 (14)	0.0014 (12)	0.0051 (12)	0.0064 (11)
C8	0.0478 (17)	0.0519 (14)	0.0595 (15)	−0.0069 (12)	−0.0024 (13)	0.0099 (12)
C9	0.0406 (15)	0.0500 (14)	0.0463 (13)	0.0029 (11)	0.0043 (11)	0.0035 (11)
C10	0.0426 (15)	0.0451 (13)	0.0509 (14)	0.0026 (11)	0.0062 (12)	0.0015 (11)
C11	0.0494 (15)	0.0415 (12)	0.0492 (14)	−0.0014 (11)	0.0047 (12)	0.0026 (11)
C12	0.0644 (18)	0.0512 (14)	0.0568 (16)	0.0021 (12)	0.0003 (14)	0.0050 (12)
C13	0.085 (2)	0.0614 (16)	0.0521 (16)	−0.0100 (15)	0.0066 (15)	−0.0036 (13)
C14	0.089 (2)	0.0484 (15)	0.072 (2)	0.0009 (15)	0.0265 (17)	−0.0030 (14)
C15	0.0634 (19)	0.0525 (16)	0.0798 (19)	0.0114 (13)	0.0147 (16)	0.0081 (14)
C16	0.0539 (16)	0.0553 (14)	0.0543 (15)	0.0022 (12)	0.0050 (13)	0.0060 (12)
C17	0.0416 (15)	0.0476 (13)	0.0475 (14)	0.0012 (11)	0.0036 (12)	0.0051 (11)
C18	0.0456 (16)	0.0513 (14)	0.0656 (16)	0.0014 (12)	0.0044 (13)	0.0007 (12)
C19	0.0571 (19)	0.0591 (15)	0.0787 (19)	−0.0114 (14)	0.0052 (15)	0.0041 (14)
C20	0.0555 (19)	0.0782 (19)	0.0767 (19)	−0.0143 (15)	0.0144 (16)	0.0144 (15)
C21	0.064 (2)	0.0776 (18)	0.0662 (18)	−0.0037 (15)	0.0251 (15)	0.0000 (14)
C22	0.0563 (18)	0.0591 (15)	0.0590 (16)	−0.0033 (13)	0.0131 (14)	−0.0008 (12)
C23	0.0607 (18)	0.0618 (16)	0.0864 (19)	−0.0165 (13)	0.0159 (15)	0.0018 (14)
Cl'	0.0724 (6)	0.1373 (7)	0.0779 (5)	−0.0182 (5)	0.0125 (4)	0.0366 (5)
N1'	0.0484 (15)	0.0665 (14)	0.0782 (15)	−0.0006 (11)	0.0143 (12)	−0.0167 (11)
N2'	0.0398 (13)	0.0492 (11)	0.0564 (12)	−0.0022 (9)	0.0078 (10)	−0.0081 (9)
N3'	0.0432 (13)	0.0534 (11)	0.0555 (12)	−0.0005 (10)	0.0101 (10)	−0.0005 (9)
C1'	0.0441 (17)	0.0729 (17)	0.0549 (15)	−0.0067 (13)	0.0087 (13)	−0.0148 (13)
C2'	0.0522 (19)	0.103 (2)	0.076 (2)	0.0058 (15)	0.0205 (16)	−0.0141 (17)
C3'	0.0525 (19)	0.125 (3)	0.0647 (19)	−0.0080 (18)	0.0235 (15)	0.0013 (18)
C4'	0.0513 (19)	0.098 (2)	0.0482 (16)	−0.0121 (15)	0.0048 (14)	0.0064 (14)
C5'	0.0450 (17)	0.0797 (17)	0.0502 (15)	−0.0065 (13)	0.0046 (13)	0.0011 (13)
C6'	0.0403 (16)	0.0650 (15)	0.0491 (14)	−0.0061 (12)	0.0064 (12)	−0.0084 (12)
C7'	0.0372 (15)	0.0536 (14)	0.0507 (14)	−0.0048 (11)	0.0064 (12)	−0.0072 (11)
C8'	0.0448 (17)	0.0545 (15)	0.0728 (18)	0.0003 (12)	0.0085 (13)	−0.0159 (13)
C9'	0.0409 (15)	0.0505 (14)	0.0523 (14)	−0.0016 (11)	0.0037 (12)	−0.0071 (11)
C10'	0.0405 (15)	0.0498 (13)	0.0479 (14)	−0.0034 (11)	0.0071 (11)	−0.0058 (11)
C11'	0.0456 (15)	0.0441 (13)	0.0517 (15)	0.0020 (11)	0.0083 (12)	−0.0053 (11)
C12'	0.0643 (18)	0.0497 (14)	0.0600 (16)	−0.0019 (12)	−0.0013 (14)	−0.0071 (12)
C13'	0.079 (2)	0.0624 (16)	0.0588 (17)	0.0043 (15)	−0.0002 (15)	0.0006 (13)
C14'	0.076 (2)	0.0499 (15)	0.0716 (18)	0.0016 (14)	0.0222 (15)	0.0039 (14)
C15'	0.0620 (18)	0.0575 (16)	0.0709 (18)	−0.0146 (13)	0.0104 (15)	−0.0079 (14)
C16'	0.0529 (17)	0.0556 (14)	0.0539 (15)	−0.0071 (12)	0.0032 (13)	−0.0060 (12)
C17'	0.0445 (15)	0.0484 (13)	0.0446 (13)	−0.0018 (11)	0.0032 (12)	−0.0058 (11)
C18'	0.0452 (16)	0.0539 (14)	0.0600 (16)	−0.0041 (12)	0.0060 (13)	−0.0031 (12)
C19'	0.0554 (19)	0.0564 (15)	0.0713 (18)	0.0078 (13)	0.0026 (15)	−0.0043 (13)
C20'	0.0593 (19)	0.0711 (18)	0.0698 (18)	0.0142 (14)	0.0112 (15)	−0.0136 (14)
C21'	0.0578 (19)	0.0822 (18)	0.0603 (17)	−0.0007 (14)	0.0243 (14)	−0.0035 (14)
C22'	0.0564 (18)	0.0576 (15)	0.0555 (15)	0.0029 (13)	0.0125 (13)	0.0006 (12)
C23'	0.070 (2)	0.0565 (16)	0.135 (3)	0.0129 (14)	0.0262 (18)	−0.0038 (16)

Geometric parameters (Å, º)

Cl—C4	1.737 (2)	Cl'—C4'	1.744 (2)
N1—C8	1.292 (3)	N1'—C8'	1.290 (3)
N1—C1	1.391 (3)	N1'—C1'	1.388 (3)
N2—C7	1.394 (2)	N2'—C7'	1.390 (2)
N2—C8	1.409 (3)	N2'—C8'	1.404 (3)
N2—C9	1.413 (2)	N2'—C9'	1.408 (3)
N3—C7	1.311 (2)	N3'—C7'	1.307 (2)
N3—C10	1.387 (2)	N3'—C10'	1.383 (2)
C1—C6	1.396 (3)	C1'—C6'	1.390 (3)
C1—C2	1.396 (3)	C1'—C2'	1.406 (3)
C2—C3	1.369 (3)	C2'—C3'	1.366 (3)
C2—H2	0.9300	C2'—H2'	0.9300
C3—C4	1.395 (3)	C3'—C4'	1.386 (3)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.368 (3)	C4'—C5'	1.367 (3)
C5—C6	1.391 (3)	C5'—C6'	1.398 (3)
C5—H5	0.9300	C5'—H5'	0.9300
C6—C7	1.429 (3)	C6'—C7'	1.435 (3)
C8—C23	1.485 (3)	C8'—C23'	1.487 (3)
C9—C10	1.374 (3)	C9'—C10'	1.382 (3)
C9—C11	1.478 (3)	C9'—C11'	1.477 (3)
C10—C17	1.478 (3)	C10'—C17'	1.476 (3)
C11—C12	1.386 (3)	C11'—C16'	1.385 (3)
C11—C16	1.388 (3)	C11'—C12'	1.391 (3)
C12—C13	1.382 (3)	C12'—C13'	1.381 (3)
C12—H12	0.9300	C12'—H12'	0.9300
C13—C14	1.370 (3)	C13'—C14'	1.368 (3)
C13—H13	0.9300	C13'—H13'	0.9300
C14—C15	1.376 (3)	C14'—C15'	1.367 (3)
C14—H14	0.9300	C14'—H14'	0.9300
C15—C16	1.383 (3)	C15'—C16'	1.382 (3)
C15—H15	0.9300	C15'—H15'	0.9300
C16—H16	0.9300	C16'—H16'	0.9300
C17—C22	1.390 (3)	C17'—C22'	1.388 (3)
C17—C18	1.393 (3)	C17'—C18'	1.391 (3)
C18—C19	1.379 (3)	C18'—C19'	1.371 (3)
C18—H18	0.9300	C18'—H18'	0.9300
C19—C20	1.371 (3)	C19'—C20'	1.379 (3)
C19—H19	0.9300	C19'—H19'	0.9300
C20—C21	1.375 (3)	C20'—C21'	1.369 (3)
C20—H20	0.9300	C20'—H20'	0.9300
C21—C22	1.386 (3)	C21'—C22'	1.384 (3)
C21—H21	0.9300	C21'—H21'	0.9300
C22—H22	0.9300	C22'—H22'	0.9300
C23—H23A	0.9600	C23'—H23D	0.9600
C23—H23B	0.9600	C23'—H23E	0.9600
C23—H23C	0.9600	C23'—H23F	0.9600
C8—N1—C1	120.0 (2)	C8'—N1'—C1'	120.0 (2)
C7—N2—C8	120.07 (19)	C7'—N2'—C8'	120.98 (19)
C7—N2—C9	105.96 (17)	C7'—N2'—C9'	105.66 (17)
C8—N2—C9	133.89 (19)	C8'—N2'—C9'	133.32 (19)
C7—N3—C10	105.64 (18)	C7'—N3'—C10'	105.52 (18)
N1—C1—C6	122.8 (2)	N1'—C1'—C6'	122.9 (2)
N1—C1—C2	118.5 (2)	N1'—C1'—C2'	118.9 (2)
C6—C1—C2	118.7 (2)	C6'—C1'—C2'	118.2 (2)
C3—C2—C1	120.5 (2)	C3'—C2'—C1'	120.6 (3)
C3—C2—H2	119.7	C3'—C2'—H2'	119.7
C1—C2—H2	119.7	C1'—C2'—H2'	119.7
C2—C3—C4	119.9 (3)	C2'—C3'—C4'	119.9 (3)
C2—C3—H3	120.0	C2'—C3'—H3'	120.1
C4—C3—H3	120.0	C4'—C3'—H3'	120.1
C5—C4—C3	120.9 (2)	C5'—C4'—C3'	121.4 (2)
C5—C4—Cl	120.2 (2)	C5'—C4'—Cl'	119.6 (2)
C3—C4—Cl	118.9 (2)	C3'—C4'—Cl'	118.9 (2)
C4—C5—C6	119.2 (2)	C4'—C5'—C6'	118.7 (2)
C4—C5—H5	120.4	C4'—C5'—H5'	120.7
C6—C5—H5	120.4	C6'—C5'—H5'	120.7
C5—C6—C1	120.8 (2)	C1'—C6'—C5'	121.2 (2)
C5—C6—C7	122.7 (2)	C1'—C6'—C7'	116.7 (2)
C1—C6—C7	116.5 (2)	C5'—C6'—C7'	122.1 (2)
N3—C7—N2	112.1 (2)	N3'—C7'—N2'	112.71 (19)
N3—C7—C6	128.9 (2)	N3'—C7'—C6'	129.2 (2)
N2—C7—C6	119.0 (2)	N2'—C7'—C6'	118.1 (2)
N1—C8—N2	121.7 (2)	N1'—C8'—N2'	121.3 (2)
N1—C8—C23	118.8 (2)	N1'—C8'—C23'	118.5 (2)
N2—C8—C23	119.5 (2)	N2'—C8'—C23'	120.1 (2)
C10—C9—N2	104.94 (18)	C10'—C9'—N2'	105.08 (18)
C10—C9—C11	130.5 (2)	C10'—C9'—C11'	130.2 (2)
N2—C9—C11	124.60 (19)	N2'—C9'—C11'	124.65 (19)
C9—C10—N3	111.4 (2)	C9'—C10'—N3'	111.0 (2)
C9—C10—C17	130.9 (2)	C9'—C10'—C17'	130.9 (2)
N3—C10—C17	117.71 (19)	N3'—C10'—C17'	118.09 (19)
C12—C11—C16	118.4 (2)	C16'—C11'—C12'	118.3 (2)
C12—C11—C9	121.4 (2)	C16'—C11'—C9'	120.5 (2)
C16—C11—C9	120.2 (2)	C12'—C11'—C9'	121.3 (2)
C13—C12—C11	120.9 (2)	C13'—C12'—C11'	120.5 (2)
C13—C12—H12	119.5	C13'—C12'—H12'	119.7
C11—C12—H12	119.5	C11'—C12'—H12'	119.7
C14—C13—C12	120.2 (2)	C14'—C13'—C12'	120.2 (2)
C14—C13—H13	119.9	C14'—C13'—H13'	119.9
C12—C13—H13	119.9	C12'—C13'—H13'	119.9
C13—C14—C15	119.6 (2)	C15'—C14'—C13'	120.1 (2)
C13—C14—H14	120.2	C15'—C14'—H14'	120.0
C15—C14—H14	120.2	C13'—C14'—H14'	120.0
C14—C15—C16	120.6 (2)	C14'—C15'—C16'	120.2 (2)
C14—C15—H15	119.7	C14'—C15'—H15'	119.9
C16—C15—H15	119.7	C16'—C15'—H15'	119.9
C15—C16—C11	120.3 (2)	C15'—C16'—C11'	120.6 (2)
C15—C16—H16	119.9	C15'—C16'—H16'	119.7
C11—C16—H16	119.9	C11'—C16'—H16'	119.7
C22—C17—C18	117.4 (2)	C22'—C17'—C18'	117.4 (2)
C22—C17—C10	124.4 (2)	C22'—C17'—C10'	124.3 (2)
C18—C17—C10	118.2 (2)	C18'—C17'—C10'	118.3 (2)
C19—C18—C17	121.5 (2)	C19'—C18'—C17'	121.8 (2)
C19—C18—H18	119.3	C19'—C18'—H18'	119.1
C17—C18—H18	119.3	C17'—C18'—H18'	119.1
C20—C19—C18	120.1 (2)	C18'—C19'—C20'	120.1 (2)
C20—C19—H19	119.9	C18'—C19'—H19'	119.9
C18—C19—H19	119.9	C20'—C19'—H19'	119.9
C19—C20—C21	119.8 (2)	C21'—C20'—C19'	119.1 (2)
C19—C20—H20	120.1	C21'—C20'—H20'	120.4
C21—C20—H20	120.1	C19'—C20'—H20'	120.4
C20—C21—C22	120.2 (2)	C20'—C21'—C22'	121.0 (2)
C20—C21—H21	119.9	C20'—C21'—H21'	119.5
C22—C21—H21	119.9	C22'—C21'—H21'	119.5
C21—C22—C17	121.0 (2)	C21'—C22'—C17'	120.6 (2)
C21—C22—H22	119.5	C21'—C22'—H22'	119.7
C17—C22—H22	119.5	C17'—C22'—H22'	119.7
C8—C23—H23A	109.5	C8'—C23'—H23D	109.5
C8—C23—H23B	109.5	C8'—C23'—H23E	109.5
H23A—C23—H23B	109.5	H23D—C23'—H23E	109.5
C8—C23—H23C	109.5	C8'—C23'—H23F	109.5
H23A—C23—H23C	109.5	H23D—C23'—H23F	109.5
H23B—C23—H23C	109.5	H23E—C23'—H23F	109.5
C8—N1—C1—C6	0.8 (3)	C8'—N1'—C1'—C6'	−1.5 (3)
C8—N1—C1—C2	−179.4 (2)	C8'—N1'—C1'—C2'	178.7 (2)
N1—C1—C2—C3	180.0 (2)	N1'—C1'—C2'—C3'	179.7 (2)
C6—C1—C2—C3	−0.2 (4)	C6'—C1'—C2'—C3'	−0.1 (4)
C1—C2—C3—C4	−0.1 (4)	C1'—C2'—C3'—C4'	−0.2 (4)
C2—C3—C4—C5	0.5 (4)	C2'—C3'—C4'—C5'	0.5 (4)
C2—C3—C4—Cl	−179.07 (18)	C2'—C3'—C4'—Cl'	179.5 (2)
C3—C4—C5—C6	−0.6 (4)	C3'—C4'—C5'—C6'	−0.5 (4)
Cl—C4—C5—C6	178.97 (17)	Cl'—C4'—C5'—C6'	−179.52 (17)
C4—C5—C6—C1	0.3 (3)	N1'—C1'—C6'—C5'	−179.7 (2)
C4—C5—C6—C7	−178.6 (2)	C2'—C1'—C6'—C5'	0.1 (3)
N1—C1—C6—C5	179.9 (2)	N1'—C1'—C6'—C7'	2.2 (3)
C2—C1—C6—C5	0.1 (3)	C2'—C1'—C6'—C7'	−178.0 (2)
N1—C1—C6—C7	−1.2 (3)	C4'—C5'—C6'—C1'	0.2 (3)
C2—C1—C6—C7	179.0 (2)	C4'—C5'—C6'—C7'	178.2 (2)
C10—N3—C7—N2	−0.6 (2)	C10'—N3'—C7'—N2'	0.3 (2)
C10—N3—C7—C6	178.4 (2)	C10'—N3'—C7'—C6'	−177.2 (2)
C8—N2—C7—N3	177.70 (18)	C8'—N2'—C7'—N3'	−178.53 (19)
C9—N2—C7—N3	0.6 (2)	C9'—N2'—C7'—N3'	−0.5 (2)
C8—N2—C7—C6	−1.4 (3)	C8'—N2'—C7'—C6'	−0.7 (3)
C9—N2—C7—C6	−178.47 (19)	C9'—N2'—C7'—C6'	177.42 (18)
C5—C6—C7—N3	1.4 (4)	C1'—C6'—C7'—N3'	176.4 (2)
C1—C6—C7—N3	−177.5 (2)	C5'—C6'—C7'—N3'	−1.7 (4)
C5—C6—C7—N2	−179.66 (19)	C1'—C6'—C7'—N2'	−1.1 (3)
C1—C6—C7—N2	1.4 (3)	C5'—C6'—C7'—N2'	−179.17 (19)
C1—N1—C8—N2	−0.6 (3)	C1'—N1'—C8'—N2'	−0.4 (3)
C1—N1—C8—C23	−179.95 (19)	C1'—N1'—C8'—C23'	178.2 (2)
C7—N2—C8—N1	1.0 (3)	C7'—N2'—C8'—N1'	1.5 (3)
C9—N2—C8—N1	177.1 (2)	C9'—N2'—C8'—N1'	−176.0 (2)
C7—N2—C8—C23	−179.72 (19)	C7'—N2'—C8'—C23'	−177.2 (2)
C9—N2—C8—C23	−3.6 (3)	C9'—N2'—C8'—C23'	5.4 (4)
C7—N2—C9—C10	−0.4 (2)	C7'—N2'—C9'—C10'	0.4 (2)
C8—N2—C9—C10	−176.9 (2)	C8'—N2'—C9'—C10'	178.1 (2)
C7—N2—C9—C11	179.39 (19)	C7'—N2'—C9'—C11'	−176.76 (19)
C8—N2—C9—C11	2.9 (4)	C8'—N2'—C9'—C11'	1.0 (4)
N2—C9—C10—N3	0.1 (2)	N2'—C9'—C10'—N3'	−0.2 (2)
C11—C9—C10—N3	−179.7 (2)	C11'—C9'—C10'—N3'	176.7 (2)
N2—C9—C10—C17	−178.5 (2)	N2'—C9'—C10'—C17'	178.9 (2)
C11—C9—C10—C17	1.7 (4)	C11'—C9'—C10'—C17'	−4.2 (4)
C7—N3—C10—C9	0.3 (2)	C7'—N3'—C10'—C9'	−0.1 (2)
C7—N3—C10—C17	179.11 (18)	C7'—N3'—C10'—C17'	−179.28 (18)
C10—C9—C11—C12	−104.9 (3)	C10'—C9'—C11'—C16'	−74.5 (3)
N2—C9—C11—C12	75.3 (3)	N2'—C9'—C11'—C16'	101.8 (3)
C10—C9—C11—C16	73.0 (3)	C10'—C9'—C11'—C12'	104.4 (3)
N2—C9—C11—C16	−106.7 (3)	N2'—C9'—C11'—C12'	−79.2 (3)
C16—C11—C12—C13	2.0 (3)	C16'—C11'—C12'—C13'	−2.6 (3)
C9—C11—C12—C13	179.9 (2)	C9'—C11'—C12'—C13'	178.4 (2)
C11—C12—C13—C14	−0.3 (4)	C11'—C12'—C13'—C14'	0.8 (4)
C12—C13—C14—C15	−1.7 (4)	C12'—C13'—C14'—C15'	1.6 (4)
C13—C14—C15—C16	1.9 (4)	C13'—C14'—C15'—C16'	−2.2 (4)
C14—C15—C16—C11	−0.3 (4)	C14'—C15'—C16'—C11'	0.3 (4)
C12—C11—C16—C15	−1.7 (3)	C12'—C11'—C16'—C15'	2.1 (3)
C9—C11—C16—C15	−179.7 (2)	C9'—C11'—C16'—C15'	−179.0 (2)
C9—C10—C17—C22	3.5 (4)	C9'—C10'—C17'—C22'	−4.0 (4)
N3—C10—C17—C22	−175.0 (2)	N3'—C10'—C17'—C22'	175.0 (2)
C9—C10—C17—C18	−178.0 (2)	C9'—C10'—C17'—C18'	177.1 (2)
N3—C10—C17—C18	3.4 (3)	N3'—C10'—C17'—C18'	−3.9 (3)
C22—C17—C18—C19	0.3 (3)	C22'—C17'—C18'—C19'	−0.4 (3)
C10—C17—C18—C19	−178.3 (2)	C10'—C17'—C18'—C19'	178.5 (2)
C17—C18—C19—C20	−0.7 (4)	C17'—C18'—C19'—C20'	0.8 (4)
C18—C19—C20—C21	0.5 (4)	C18'—C19'—C20'—C21'	−0.6 (4)
C19—C20—C21—C22	0.0 (4)	C19'—C20'—C21'—C22'	0.0 (4)
C20—C21—C22—C17	−0.4 (4)	C20'—C21'—C22'—C17'	0.4 (4)
C18—C17—C22—C21	0.3 (3)	C18'—C17'—C22'—C21'	−0.2 (3)
C10—C17—C22—C21	178.7 (2)	C10'—C17'—C22'—C21'	−179.1 (2)