4-(3-Chloro­benzyl­ideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

The title Schiff base compound, C₁₈H₁₆ClN₃O, was synthesized by the reaction of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro­pyrazol-3-one and 3-chloro­benzaldehyde in methanol solution. As expected, the compound adopts a trans configuration about the central C=N bond. The asymmetric unit contains two independent mol­ecules. In the crystal structure, the mol­ecules stack with no short contacts.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.157
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99

   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
   0 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, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

4-(3-Chlorobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Crystal data

C18H16ClN3O	F(000) = 1360
Mr = 325.79	Dx = 1.311 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4126 reflections
a = 6.7580 (5) Å	θ = 2.4–22.0°
b = 26.7540 (19) Å	µ = 0.24 mm^−1
c = 18.5240 (13) Å	T = 298 K
β = 99.620 (1)°	Thin_plates, yellow
V = 3302.1 (4) Å^3	0.21 × 0.18 × 0.08 mm
Z = 8

Data collection

Bruker APEX area-detector diffractometer	6822 independent reflections
Radiation source: fine-focus sealed tube	4241 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 26.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.992, Tmax = 0.995	k = −33→33
25598 measured reflections	l = −23→22

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0631P)^2 + 0.9648P] where P = (Fo^2 + 2Fc^2)/3
6822 reflections	(Δ/σ)max < 0.001
419 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.27 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
Cl1	0.09757 (16)	0.30453 (3)	0.51690 (5)	0.0995 (3)
Cl2	0.45880 (16)	0.72233 (3)	0.98769 (6)	0.1042 (3)
O1	−0.1718 (2)	0.58927 (7)	0.62396 (10)	0.0598 (5)
O2	0.6831 (2)	0.43270 (6)	0.89140 (9)	0.0583 (5)
N1	0.1273 (3)	0.61749 (8)	0.69004 (11)	0.0505 (5)
N2	0.3120 (3)	0.59553 (8)	0.71842 (11)	0.0524 (5)
N3	0.0855 (3)	0.49270 (8)	0.61430 (10)	0.0511 (5)
N4	0.3821 (3)	0.40657 (7)	0.82388 (11)	0.0497 (5)
N5	0.1991 (3)	0.42972 (8)	0.79616 (11)	0.0539 (5)
N6	0.4341 (3)	0.53059 (7)	0.90166 (10)	0.0497 (5)
C1	0.0456 (3)	0.65564 (9)	0.73030 (14)	0.0501 (6)
C2	−0.0684 (4)	0.69220 (10)	0.69224 (17)	0.0655 (7)
H2	−0.0854	0.6930	0.6414	0.079*
C3	−0.1577 (5)	0.72783 (12)	0.7295 (2)	0.0878 (10)
H3	−0.2375	0.7524	0.7036	0.105*
C4	−0.1303 (5)	0.72750 (15)	0.8039 (3)	0.0997 (12)
H4	−0.1903	0.7519	0.8287	0.120*
C5	−0.0152 (6)	0.69143 (16)	0.8420 (2)	0.0934 (11)
H5	0.0041	0.6915	0.8929	0.112*
C6	0.0738 (4)	0.65456 (11)	0.80562 (15)	0.0675 (8)
H6	0.1508	0.6296	0.8316	0.081*
C7	0.0065 (4)	0.58211 (9)	0.64837 (12)	0.0472 (6)
C8	0.1337 (3)	0.53925 (9)	0.64632 (12)	0.0459 (6)
C9	0.3168 (3)	0.54960 (9)	0.68708 (13)	0.0495 (6)
C10	0.5019 (4)	0.51925 (11)	0.69785 (16)	0.0645 (7)
H10A	0.5989	0.5344	0.6723	0.097*
H10B	0.4716	0.4862	0.6791	0.097*
H10C	0.5556	0.5174	0.7491	0.097*
C11	0.4856 (4)	0.62818 (11)	0.73824 (17)	0.0747 (9)
H11A	0.5910	0.6102	0.7686	0.112*
H11B	0.4482	0.6566	0.7646	0.112*
H11C	0.5317	0.6392	0.6946	0.112*
C12	−0.0895 (4)	0.48514 (9)	0.57726 (13)	0.0534 (6)
H12	−0.1813	0.5113	0.5710	0.064*
C13	−0.1495 (4)	0.43674 (9)	0.54453 (13)	0.0526 (6)
C14	−0.0137 (4)	0.39799 (10)	0.54585 (13)	0.0567 (7)
H14	0.1191	0.4024	0.5681	0.068*
C15	−0.0756 (5)	0.35297 (10)	0.51410 (14)	0.0623 (7)
C16	−0.2713 (5)	0.34578 (11)	0.48024 (15)	0.0713 (8)
H16	−0.3110	0.3151	0.4589	0.086*
C17	−0.4066 (5)	0.38397 (12)	0.47821 (16)	0.0750 (9)
H17	−0.5383	0.3795	0.4549	0.090*
C18	−0.3474 (4)	0.42906 (11)	0.51072 (15)	0.0660 (7)
H18	−0.4407	0.4547	0.5101	0.079*
C19	0.4612 (3)	0.36853 (9)	0.78300 (14)	0.0511 (6)
C20	0.5676 (4)	0.33043 (10)	0.82058 (17)	0.0638 (7)
H20	0.5789	0.3285	0.8712	0.077*
C21	0.6574 (5)	0.29505 (12)	0.7833 (2)	0.0900 (11)
H21	0.7321	0.2696	0.8089	0.108*
C22	0.6379 (6)	0.29703 (16)	0.7091 (3)	0.1060 (14)
H22	0.6981	0.2728	0.6841	0.127*
C23	0.5295 (6)	0.33473 (16)	0.6712 (2)	0.0967 (12)
H23	0.5155	0.3358	0.6204	0.116*
C24	0.4409 (4)	0.37122 (12)	0.70778 (16)	0.0718 (8)
H24	0.3689	0.3971	0.6822	0.086*
C25	0.5050 (3)	0.44100 (9)	0.86691 (12)	0.0457 (6)
C26	0.3815 (3)	0.48439 (9)	0.86983 (12)	0.0464 (6)
C27	0.1978 (3)	0.47499 (9)	0.82847 (13)	0.0480 (6)
C28	0.0136 (4)	0.50626 (11)	0.81879 (16)	0.0650 (7)
H28A	−0.0408	0.5088	0.7676	0.097*
H28B	0.0464	0.5390	0.8382	0.097*
H28C	−0.0837	0.4912	0.8443	0.097*
C29	0.0237 (4)	0.39868 (11)	0.77027 (16)	0.0685 (8)
H29A	−0.0556	0.3953	0.8084	0.103*
H29B	0.0668	0.3662	0.7571	0.103*
H29C	−0.0554	0.4141	0.7283	0.103*
C30	0.6081 (4)	0.53679 (9)	0.94003 (13)	0.0519 (6)
H30	0.6944	0.5095	0.9483	0.062*
C31	0.6757 (4)	0.58502 (9)	0.97119 (13)	0.0494 (6)
C32	0.5484 (4)	0.62619 (10)	0.96573 (14)	0.0577 (7)
H32	0.4162	0.6234	0.9421	0.069*
C33	0.6200 (5)	0.67098 (10)	0.99568 (15)	0.0644 (7)
C34	0.8139 (5)	0.67607 (11)	1.03114 (15)	0.0718 (8)
H34	0.8595	0.7066	1.0513	0.086*
C35	0.9397 (5)	0.63560 (11)	1.03649 (16)	0.0695 (8)
H35	1.0716	0.6387	1.0604	0.083*
C36	0.8722 (4)	0.59089 (10)	1.00694 (14)	0.0611 (7)
H36	0.9594	0.5638	1.0107	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1351 (8)	0.0605 (5)	0.0957 (6)	0.0254 (5)	−0.0017 (6)	−0.0059 (4)
Cl2	0.1268 (8)	0.0578 (5)	0.1217 (8)	0.0295 (5)	0.0024 (6)	0.0022 (5)
O1	0.0420 (10)	0.0645 (12)	0.0699 (11)	−0.0016 (8)	0.0004 (8)	−0.0069 (9)
O2	0.0403 (10)	0.0580 (11)	0.0732 (12)	0.0014 (8)	−0.0002 (8)	−0.0072 (9)
N1	0.0388 (11)	0.0545 (12)	0.0574 (12)	−0.0039 (9)	0.0060 (9)	−0.0058 (10)
N2	0.0332 (11)	0.0619 (14)	0.0612 (13)	−0.0063 (9)	0.0054 (9)	−0.0053 (11)
N3	0.0514 (13)	0.0533 (13)	0.0503 (12)	−0.0049 (10)	0.0133 (10)	0.0007 (10)
N4	0.0367 (11)	0.0532 (12)	0.0571 (12)	0.0004 (9)	0.0017 (9)	−0.0010 (10)
N5	0.0339 (11)	0.0613 (14)	0.0650 (13)	−0.0055 (10)	0.0043 (9)	0.0020 (11)
N6	0.0488 (12)	0.0487 (12)	0.0530 (12)	−0.0024 (9)	0.0122 (10)	0.0026 (10)
C1	0.0413 (14)	0.0502 (15)	0.0599 (16)	−0.0085 (11)	0.0116 (11)	−0.0088 (12)
C2	0.0616 (18)	0.0610 (18)	0.0734 (19)	0.0006 (14)	0.0094 (14)	0.0022 (15)
C3	0.068 (2)	0.061 (2)	0.133 (3)	0.0072 (16)	0.011 (2)	−0.013 (2)
C4	0.076 (2)	0.093 (3)	0.135 (4)	0.001 (2)	0.030 (2)	−0.051 (3)
C5	0.090 (3)	0.116 (3)	0.079 (2)	−0.012 (2)	0.028 (2)	−0.036 (2)
C6	0.0694 (19)	0.0713 (19)	0.0620 (18)	−0.0058 (15)	0.0116 (14)	−0.0094 (15)
C7	0.0449 (14)	0.0521 (15)	0.0461 (13)	−0.0078 (11)	0.0115 (11)	−0.0012 (11)
C8	0.0442 (14)	0.0493 (14)	0.0465 (13)	−0.0061 (11)	0.0143 (11)	−0.0005 (11)
C9	0.0410 (14)	0.0562 (15)	0.0539 (14)	−0.0057 (11)	0.0153 (11)	0.0017 (12)
C10	0.0442 (15)	0.0704 (18)	0.0805 (19)	0.0014 (13)	0.0147 (13)	0.0041 (15)
C11	0.0474 (16)	0.082 (2)	0.094 (2)	−0.0169 (15)	0.0081 (15)	−0.0243 (17)
C12	0.0560 (16)	0.0494 (15)	0.0555 (15)	−0.0011 (12)	0.0112 (13)	−0.0008 (12)
C13	0.0591 (16)	0.0523 (15)	0.0468 (14)	−0.0067 (13)	0.0098 (12)	0.0024 (12)
C14	0.0633 (17)	0.0547 (16)	0.0493 (14)	−0.0028 (13)	0.0016 (12)	0.0001 (12)
C15	0.084 (2)	0.0491 (16)	0.0519 (15)	0.0002 (14)	0.0062 (14)	0.0058 (12)
C16	0.096 (2)	0.0532 (17)	0.0590 (17)	−0.0218 (17)	−0.0026 (16)	0.0061 (14)
C17	0.073 (2)	0.073 (2)	0.072 (2)	−0.0208 (17)	−0.0068 (15)	0.0070 (16)
C18	0.0608 (18)	0.0597 (17)	0.0739 (19)	−0.0057 (14)	0.0010 (14)	0.0045 (15)
C19	0.0403 (14)	0.0509 (15)	0.0625 (16)	−0.0114 (11)	0.0100 (12)	−0.0069 (13)
C20	0.0533 (16)	0.0568 (17)	0.0788 (19)	−0.0048 (13)	0.0038 (14)	−0.0013 (15)
C21	0.062 (2)	0.063 (2)	0.140 (3)	0.0038 (16)	0.003 (2)	−0.021 (2)
C22	0.074 (2)	0.106 (3)	0.141 (4)	−0.007 (2)	0.029 (3)	−0.064 (3)
C23	0.089 (3)	0.122 (3)	0.081 (2)	−0.017 (2)	0.022 (2)	−0.038 (2)
C24	0.072 (2)	0.078 (2)	0.0657 (19)	−0.0131 (16)	0.0126 (15)	−0.0107 (16)
C25	0.0389 (14)	0.0510 (14)	0.0470 (13)	−0.0063 (11)	0.0070 (11)	0.0018 (11)
C26	0.0410 (13)	0.0498 (14)	0.0495 (13)	−0.0008 (11)	0.0106 (11)	0.0058 (11)
C27	0.0388 (13)	0.0531 (15)	0.0543 (14)	−0.0031 (11)	0.0143 (11)	0.0089 (12)
C28	0.0452 (15)	0.0714 (18)	0.0796 (19)	0.0069 (13)	0.0144 (13)	0.0156 (15)
C29	0.0456 (15)	0.0766 (19)	0.0800 (19)	−0.0157 (14)	0.0009 (14)	−0.0044 (16)
C30	0.0525 (16)	0.0497 (15)	0.0538 (14)	0.0026 (12)	0.0100 (12)	0.0029 (12)
C31	0.0523 (15)	0.0499 (15)	0.0458 (13)	−0.0005 (12)	0.0073 (11)	0.0064 (11)
C32	0.0617 (17)	0.0560 (16)	0.0532 (15)	0.0030 (13)	0.0036 (12)	0.0054 (12)
C33	0.084 (2)	0.0480 (16)	0.0593 (16)	0.0075 (14)	0.0062 (15)	0.0075 (13)
C34	0.094 (2)	0.0524 (17)	0.0638 (18)	−0.0115 (16)	−0.0031 (16)	0.0024 (14)
C35	0.0673 (19)	0.0643 (19)	0.0703 (19)	−0.0088 (15)	−0.0076 (15)	0.0025 (15)
C36	0.0623 (18)	0.0563 (16)	0.0618 (16)	0.0027 (13)	0.0023 (13)	0.0058 (13)

Geometric parameters (Å, º)

Cl1—C15	1.741 (3)	C13—C18	1.394 (4)
Cl2—C33	1.744 (3)	C14—C15	1.375 (4)
O1—C7	1.229 (3)	C14—H14	0.9300
O2—C25	1.233 (3)	C15—C16	1.379 (4)
N1—C7	1.396 (3)	C16—C17	1.367 (4)
N1—N2	1.400 (3)	C16—H16	0.9300
N1—C1	1.428 (3)	C17—C18	1.377 (4)
N2—C9	1.362 (3)	C17—H17	0.9300
N2—C11	1.459 (3)	C18—H18	0.9300
N3—C12	1.280 (3)	C19—C20	1.369 (4)
N3—C8	1.394 (3)	C19—C24	1.379 (4)
N4—C25	1.397 (3)	C20—C21	1.372 (4)
N4—N5	1.401 (3)	C20—H20	0.9300
N4—C19	1.425 (3)	C21—C22	1.359 (5)
N5—C27	1.352 (3)	C21—H21	0.9300
N5—C29	1.461 (3)	C22—C23	1.369 (5)
N6—C30	1.279 (3)	C22—H22	0.9300
N6—C26	1.390 (3)	C23—C24	1.380 (4)
C1—C2	1.366 (4)	C23—H23	0.9300
C1—C6	1.377 (4)	C24—H24	0.9300
C2—C3	1.375 (4)	C25—C26	1.436 (3)
C2—H2	0.9300	C26—C27	1.369 (3)
C3—C4	1.359 (5)	C27—C28	1.485 (3)
C3—H3	0.9300	C28—H28A	0.9600
C4—C5	1.361 (5)	C28—H28B	0.9600
C4—H4	0.9300	C28—H28C	0.9600
C5—C6	1.386 (4)	C29—H29A	0.9600
C5—H5	0.9300	C29—H29B	0.9600
C6—H6	0.9300	C29—H29C	0.9600
C7—C8	1.437 (3)	C30—C31	1.456 (3)
C8—C9	1.366 (3)	C30—H30	0.9300
C9—C10	1.477 (3)	C31—C36	1.391 (3)
C10—H10A	0.9600	C31—C32	1.391 (3)
C10—H10B	0.9600	C32—C33	1.374 (4)
C10—H10C	0.9600	C32—H32	0.9300
C11—H11A	0.9600	C33—C34	1.371 (4)
C11—H11B	0.9600	C34—C35	1.370 (4)
C11—H11C	0.9600	C34—H34	0.9300
C12—C13	1.458 (3)	C35—C36	1.362 (4)
C12—H12	0.9300	C35—H35	0.9300
C13—C14	1.382 (3)	C36—H36	0.9300
C7—N1—N2	108.99 (19)	C15—C16—H16	120.2
C7—N1—C1	122.13 (19)	C16—C17—C18	119.9 (3)
N2—N1—C1	120.14 (19)	C16—C17—H17	120.0
C9—N2—N1	107.58 (18)	C18—C17—H17	120.0
C9—N2—C11	124.9 (2)	C17—C18—C13	120.8 (3)
N1—N2—C11	118.1 (2)	C17—C18—H18	119.6
C12—N3—C8	119.9 (2)	C13—C18—H18	119.6
C25—N4—N5	108.76 (19)	C20—C19—C24	120.5 (3)
C25—N4—C19	122.25 (19)	C20—C19—N4	118.3 (2)
N5—N4—C19	120.50 (19)	C24—C19—N4	121.1 (2)
C27—N5—N4	107.73 (18)	C19—C20—C21	119.8 (3)
C27—N5—C29	126.1 (2)	C19—C20—H20	120.1
N4—N5—C29	119.1 (2)	C21—C20—H20	120.1
C30—N6—C26	119.8 (2)	C22—C21—C20	120.4 (4)
C2—C1—C6	120.6 (3)	C22—C21—H21	119.8
C2—C1—N1	118.4 (2)	C20—C21—H21	119.8
C6—C1—N1	120.9 (2)	C21—C22—C23	120.0 (4)
C1—C2—C3	119.6 (3)	C21—C22—H22	120.0
C1—C2—H2	120.2	C23—C22—H22	120.0
C3—C2—H2	120.2	C22—C23—C24	120.5 (4)
C4—C3—C2	120.5 (3)	C22—C23—H23	119.7
C4—C3—H3	119.7	C24—C23—H23	119.7
C2—C3—H3	119.7	C19—C24—C23	118.7 (3)
C3—C4—C5	120.0 (3)	C19—C24—H24	120.6
C3—C4—H4	120.0	C23—C24—H24	120.6
C5—C4—H4	120.0	O2—C25—N4	122.8 (2)
C4—C5—C6	120.6 (3)	O2—C25—C26	132.0 (2)
C4—C5—H5	119.7	N4—C25—C26	105.12 (19)
C6—C5—H5	119.7	C27—C26—N6	123.0 (2)
C1—C6—C5	118.6 (3)	C27—C26—C25	108.0 (2)
C1—C6—H6	120.7	N6—C26—C25	128.8 (2)
C5—C6—H6	120.7	N5—C27—C26	109.9 (2)
O1—C7—N1	123.0 (2)	N5—C27—C28	121.2 (2)
O1—C7—C8	131.9 (2)	C26—C27—C28	128.9 (2)
N1—C7—C8	105.0 (2)	C27—C28—H28A	109.5
C9—C8—N3	122.8 (2)	C27—C28—H28B	109.5
C9—C8—C7	108.3 (2)	H28A—C28—H28B	109.5
N3—C8—C7	128.7 (2)	C27—C28—H28C	109.5
N2—C9—C8	109.5 (2)	H28A—C28—H28C	109.5
N2—C9—C10	121.2 (2)	H28B—C28—H28C	109.5
C8—C9—C10	129.2 (2)	N5—C29—H29A	109.5
C9—C10—H10A	109.5	N5—C29—H29B	109.5
C9—C10—H10B	109.5	H29A—C29—H29B	109.5
H10A—C10—H10B	109.5	N5—C29—H29C	109.5
C9—C10—H10C	109.5	H29A—C29—H29C	109.5
H10A—C10—H10C	109.5	H29B—C29—H29C	109.5
H10B—C10—H10C	109.5	N6—C30—C31	122.3 (2)
N2—C11—H11A	109.5	N6—C30—H30	118.9
N2—C11—H11B	109.5	C31—C30—H30	118.9
H11A—C11—H11B	109.5	C36—C31—C32	118.4 (2)
N2—C11—H11C	109.5	C36—C31—C30	120.0 (2)
H11A—C11—H11C	109.5	C32—C31—C30	121.6 (2)
H11B—C11—H11C	109.5	C33—C32—C31	119.3 (3)
N3—C12—C13	122.1 (2)	C33—C32—H32	120.4
N3—C12—H12	119.0	C31—C32—H32	120.4
C13—C12—H12	119.0	C34—C33—C32	121.6 (3)
C14—C13—C18	118.8 (2)	C34—C33—Cl2	119.7 (2)
C14—C13—C12	121.4 (2)	C32—C33—Cl2	118.7 (2)
C18—C13—C12	119.8 (2)	C35—C34—C33	119.2 (3)
C15—C14—C13	119.7 (3)	C35—C34—H34	120.4
C15—C14—H14	120.1	C33—C34—H34	120.4
C13—C14—H14	120.1	C36—C35—C34	120.2 (3)
C14—C15—C16	121.1 (3)	C36—C35—H35	119.9
C14—C15—Cl1	119.0 (2)	C34—C35—H35	119.9
C16—C15—Cl1	119.9 (2)	C35—C36—C31	121.3 (3)
C17—C16—C15	119.6 (3)	C35—C36—H36	119.3
C17—C16—H16	120.2	C31—C36—H36	119.3
C7—N1—N2—C9	8.0 (2)	C15—C16—C17—C18	−0.8 (4)
C1—N1—N2—C9	156.2 (2)	C16—C17—C18—C13	1.4 (4)
C7—N1—N2—C11	156.2 (2)	C14—C13—C18—C17	−0.9 (4)
C1—N1—N2—C11	−55.6 (3)	C12—C13—C18—C17	178.7 (2)
C25—N4—N5—C27	−7.6 (2)	C25—N4—C19—C20	69.3 (3)
C19—N4—N5—C27	−156.3 (2)	N5—N4—C19—C20	−146.3 (2)
C25—N4—N5—C29	−160.1 (2)	C25—N4—C19—C24	−107.3 (3)
C19—N4—N5—C29	51.2 (3)	N5—N4—C19—C24	37.1 (3)
C7—N1—C1—C2	−67.9 (3)	C24—C19—C20—C21	1.1 (4)
N2—N1—C1—C2	148.1 (2)	N4—C19—C20—C21	−175.6 (2)
C7—N1—C1—C6	109.5 (3)	C19—C20—C21—C22	−1.4 (5)
N2—N1—C1—C6	−34.5 (3)	C20—C21—C22—C23	0.6 (6)
C6—C1—C2—C3	−0.8 (4)	C21—C22—C23—C24	0.6 (6)
N1—C1—C2—C3	176.5 (2)	C20—C19—C24—C23	0.1 (4)
C1—C2—C3—C4	1.3 (5)	N4—C19—C24—C23	176.6 (3)
C2—C3—C4—C5	−0.6 (6)	C22—C23—C24—C19	−0.9 (5)
C3—C4—C5—C6	−0.6 (6)	N5—N4—C25—O2	−171.5 (2)
C2—C1—C6—C5	−0.3 (4)	C19—N4—C25—O2	−23.5 (4)
N1—C1—C6—C5	−177.6 (2)	N5—N4—C25—C26	5.4 (2)
C4—C5—C6—C1	1.0 (5)	C19—N4—C25—C26	153.4 (2)
N2—N1—C7—O1	171.3 (2)	C30—N6—C26—C27	179.6 (2)
C1—N1—C7—O1	23.8 (4)	C30—N6—C26—C25	−7.0 (4)
N2—N1—C7—C8	−5.9 (2)	O2—C25—C26—C27	175.1 (2)
C1—N1—C7—C8	−153.4 (2)	N4—C25—C26—C27	−1.4 (2)
C12—N3—C8—C9	179.3 (2)	O2—C25—C26—N6	1.0 (4)
C12—N3—C8—C7	4.5 (4)	N4—C25—C26—N6	−175.5 (2)
O1—C7—C8—C9	−175.1 (3)	N4—N5—C27—C26	6.8 (3)
N1—C7—C8—C9	1.8 (3)	C29—N5—C27—C26	156.8 (2)
O1—C7—C8—N3	0.4 (4)	N4—N5—C27—C28	−171.5 (2)
N1—C7—C8—N3	177.2 (2)	C29—N5—C27—C28	−21.5 (4)
N1—N2—C9—C8	−6.9 (3)	N6—C26—C27—N5	171.2 (2)
C11—N2—C9—C8	−152.4 (2)	C25—C26—C27—N5	−3.4 (3)
N1—N2—C9—C10	171.8 (2)	N6—C26—C27—C28	−10.8 (4)
C11—N2—C9—C10	26.3 (4)	C25—C26—C27—C28	174.7 (2)
N3—C8—C9—N2	−172.6 (2)	C26—N6—C30—C31	176.4 (2)
C7—C8—C9—N2	3.2 (3)	N6—C30—C31—C36	−174.3 (2)
N3—C8—C9—C10	8.8 (4)	N6—C30—C31—C32	5.2 (4)
C7—C8—C9—C10	−175.4 (2)	C36—C31—C32—C33	−0.1 (4)
C8—N3—C12—C13	−178.1 (2)	C30—C31—C32—C33	−179.6 (2)
N3—C12—C13—C14	−6.4 (4)	C31—C32—C33—C34	−0.3 (4)
N3—C12—C13—C18	173.9 (2)	C31—C32—C33—Cl2	179.50 (19)
C18—C13—C14—C15	0.0 (4)	C32—C33—C34—C35	0.4 (5)
C12—C13—C14—C15	−179.7 (2)	Cl2—C33—C34—C35	−179.4 (2)
C13—C14—C15—C16	0.5 (4)	C33—C34—C35—C36	−0.1 (5)
C13—C14—C15—Cl1	−179.59 (19)	C34—C35—C36—C31	−0.3 (4)
C14—C15—C16—C17	−0.1 (4)	C32—C31—C36—C35	0.4 (4)
Cl1—C15—C16—C17	−180.0 (2)	C30—C31—C36—C35	179.9 (3)