Triethyl­aminium 4-(2-chloro­benzo­yl)-3-methyl-1-(p-tol­yl)-1H-pyrazol-5-olate

Two independent ion pairs comprise the asymmetric unit of the title compound, C₆H₁₆N⁺·C₁₈H₁₄ClN₂O₂⁻. The pyrazole ring, the methyl­benzene ring and the chloro­benzene ring are each essentially planar. The dihedral angles between the two benzene rings are 97.6 (3) and 97.1 (3)° for the two anions. Weak N—H...O inter­actions are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.056
• wR factor = 0.180
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1     ..  C39     ..       2.90 Ang.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.57 Ratio
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.08 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for       C41'
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C37
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N5
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C39
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C41
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N6
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.57
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      30.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H18C   ..  H38F    ..       2.13 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C39'    ..       2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C47     ..       2.93 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      21.70 Deg.
              C39' -N5   -C39     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      14.70 Deg.
              C41' -N5   -C41     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.90 Deg.
              C37  -N5   -C37'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       9.30 Deg.
              H5A  -N5   -H5B     1.555   1.555   1.555

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Or SAINT?); data reduction: SAINT (Bruker, 1997); 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.

Triethylaminium 4-(2-chlorobenzoyl)-3-methyl-1-(p-tolyl)-5-pyrazol-5-olate

Crystal data

C6H16N^+·C18H14ClN2O2^−	F(000) = 1824
Mr = 427.96	Dx = 1.203 Mg m^−3
Monoclinic, P21/n	Melting point: 451(1) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 22.216 (2) Å	Cell parameters from 4315 reflections
b = 9.2475 (10) Å	θ = 2.7–20.7°
c = 23.913 (2) Å	µ = 0.19 mm^−1
β = 105.778 (2)°	T = 293 K
V = 4727.6 (9) Å^3	Prism, colourless
Z = 8	0.22 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	8307 independent reflections
Radiation source: fine-focus sealed tube	5157 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→26
Tmin = 0.948, Tmax = 0.982	k = −10→10
24828 measured reflections	l = −28→25

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.180	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0816P)^2 + 1.8822P] where P = (Fo^2 + 2Fc^2)/3
8307 reflections	(Δ/σ)max = 0.001
614 parameters	Δρmax = 0.38 e Å^−3
42 restraints	Δρmin = −0.30 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)
Cl1	0.68756 (4)	0.17854 (11)	0.46754 (4)	0.0929 (3)
O1	0.59473 (10)	0.3195 (2)	0.64156 (8)	0.0678 (6)
O2	0.55317 (11)	0.2099 (3)	0.52143 (9)	0.0840 (7)
N1	0.65653 (11)	0.5201 (2)	0.63910 (9)	0.0566 (6)
N2	0.67827 (13)	0.5971 (3)	0.59835 (11)	0.0735 (7)
C1	0.61886 (12)	0.4052 (3)	0.61388 (12)	0.0514 (6)
C2	0.61680 (12)	0.4121 (3)	0.55362 (11)	0.0520 (6)
C3	0.65443 (15)	0.5326 (3)	0.54891 (13)	0.0669 (8)
C4	0.6710 (2)	0.5917 (5)	0.49651 (16)	0.1128 (16)
H4A	0.6999	0.6703	0.5080	0.169*
H4B	0.6338	0.6258	0.4689	0.169*
H4C	0.6898	0.5169	0.4791	0.169*
C5	0.58321 (13)	0.3145 (3)	0.51120 (12)	0.0555 (7)
C6	0.58249 (13)	0.3372 (3)	0.44842 (12)	0.0546 (7)
C7	0.62646 (13)	0.2793 (3)	0.42434 (12)	0.0600 (7)
C8	0.62473 (17)	0.2992 (4)	0.36693 (14)	0.0752 (9)
H8	0.6554	0.2591	0.3518	0.090*
C9	0.57692 (19)	0.3792 (4)	0.33234 (14)	0.0847 (10)
H9	0.5749	0.3932	0.2934	0.102*
C10	0.53241 (18)	0.4381 (4)	0.35490 (16)	0.0882 (11)
H10	0.5003	0.4928	0.3312	0.106*
C11	0.53449 (15)	0.4176 (4)	0.41236 (14)	0.0746 (9)
H11	0.5036	0.4577	0.4272	0.090*
C12	0.67332 (12)	0.5695 (3)	0.69685 (11)	0.0530 (6)
C13	0.71661 (16)	0.6785 (4)	0.71320 (14)	0.0751 (9)
H13	0.7360	0.7157	0.6864	0.090*
C14	0.73153 (18)	0.7328 (4)	0.76836 (15)	0.0954 (12)
H14	0.7609	0.8066	0.7782	0.114*
C15	0.70418 (16)	0.6812 (4)	0.81005 (14)	0.0768 (9)
C16	0.66393 (14)	0.5676 (4)	0.79393 (13)	0.0670 (8)
H16	0.6470	0.5261	0.8217	0.080*
C17	0.64729 (13)	0.5118 (3)	0.73850 (12)	0.0609 (7)
H17	0.6188	0.4361	0.7290	0.073*
C18	0.7181 (2)	0.7486 (6)	0.87001 (16)	0.1175 (15)
H18A	0.6927	0.7036	0.8917	0.176*
H18B	0.7091	0.8502	0.8664	0.176*
H18C	0.7615	0.7347	0.8899	0.176*
Cl2	0.56583 (6)	0.16805 (14)	0.84306 (5)	0.1191 (4)
O3	0.35464 (9)	0.3163 (2)	0.89810 (9)	0.0638 (5)
O4	0.48216 (10)	0.2119 (3)	0.94675 (11)	0.0856 (7)
N3	0.36154 (9)	0.5143 (2)	0.84053 (9)	0.0504 (5)
N4	0.40741 (11)	0.5903 (3)	0.82292 (10)	0.0622 (6)
C19	0.38649 (12)	0.4015 (3)	0.87753 (11)	0.0477 (6)
C20	0.45245 (12)	0.4105 (3)	0.88481 (11)	0.0510 (6)
C21	0.46028 (13)	0.5291 (3)	0.84962 (12)	0.0589 (7)
C22	0.51859 (15)	0.5863 (4)	0.83786 (17)	0.0954 (12)
H22A	0.5083	0.6660	0.8113	0.143*
H22B	0.5380	0.5112	0.8211	0.143*
H22C	0.5469	0.6182	0.8736	0.143*
C23	0.49618 (13)	0.3162 (3)	0.92048 (12)	0.0579 (7)
C24	0.56556 (13)	0.3450 (3)	0.93125 (12)	0.0585 (7)
C25	0.60098 (15)	0.2787 (4)	0.90053 (13)	0.0699 (8)
C26	0.66626 (16)	0.2987 (4)	0.91492 (17)	0.0821 (10)
H26	0.6903	0.2516	0.8942	0.099*
C27	0.69310 (16)	0.3879 (4)	0.95953 (18)	0.0848 (10)
H27	0.7361	0.4027	0.9693	0.102*
C28	0.65818 (16)	0.4568 (4)	0.99044 (16)	0.0862 (10)
H28	0.6778	0.5187	1.0206	0.103*
C29	0.59534 (14)	0.4368 (3)	0.97808 (14)	0.0712 (8)
H29	0.5722	0.4827	1.0000	0.085*
C30	0.29905 (12)	0.5618 (3)	0.82057 (11)	0.0491 (6)
C31	0.28259 (14)	0.6620 (3)	0.77631 (13)	0.0644 (8)
H31	0.3123	0.6939	0.7582	0.077*
C32	0.22294 (15)	0.7147 (4)	0.75890 (14)	0.0775 (9)
H32	0.2129	0.7818	0.7288	0.093*
C33	0.17713 (15)	0.6720 (4)	0.78437 (15)	0.0758 (9)
C34	0.19341 (14)	0.5677 (4)	0.82673 (14)	0.0727 (9)
H34	0.1631	0.5329	0.8435	0.087*
C35	0.25317 (13)	0.5129 (3)	0.84517 (13)	0.0626 (8)
H35	0.2627	0.4429	0.8742	0.075*
C36	0.11258 (17)	0.7399 (6)	0.7677 (2)	0.1174 (16)
H36A	0.0815	0.6651	0.7583	0.176*
H36B	0.1085	0.8014	0.7345	0.176*
H36C	0.1069	0.7960	0.7996	0.176*
N5	0.55949 (13)	0.0388 (3)	0.63088 (11)	0.0782 (8)
H5A	0.5708	0.1243	0.6188	0.094*	0.459 (14)
H5B	0.5647	0.1293	0.6192	0.094*	0.541 (14)
C37	0.6035 (8)	−0.0733 (16)	0.6233 (8)	0.219 (15)	0.459 (14)
H37A	0.5799	−0.1591	0.6073	0.263*	0.459 (14)
H37B	0.6306	−0.0987	0.6611	0.263*	0.459 (14)
C38	0.6431 (11)	−0.030 (3)	0.5847 (9)	0.224 (14)	0.459 (14)
H38A	0.6763	−0.0990	0.5885	0.336*	0.459 (14)
H38B	0.6604	0.0639	0.5957	0.336*	0.459 (14)
H38C	0.6179	−0.0280	0.5451	0.336*	0.459 (14)
C39	0.5610 (9)	0.0581 (17)	0.6927 (3)	0.096 (6)	0.459 (14)
H39A	0.5287	0.1267	0.6951	0.115*	0.459 (14)
H39B	0.6010	0.0994	0.7133	0.115*	0.459 (14)
C40	0.5513 (19)	−0.081 (3)	0.7232 (8)	0.147 (14)	0.459 (14)
H40A	0.5738	−0.0753	0.7636	0.220*	0.459 (14)
H40B	0.5664	−0.1614	0.7056	0.220*	0.459 (14)
H40C	0.5075	−0.0936	0.7197	0.220*	0.459 (14)
C41	0.4945 (4)	0.0101 (11)	0.5946 (4)	0.095 (6)	0.459 (14)
H41A	0.4826	−0.0887	0.6001	0.114*	0.459 (14)
H41B	0.4920	0.0239	0.5538	0.114*	0.459 (14)
C42	0.4510 (7)	0.115 (2)	0.6133 (11)	0.175 (11)	0.459 (14)
H42A	0.4085	0.0838	0.5982	0.262*	0.459 (14)
H42B	0.4557	0.2101	0.5986	0.262*	0.459 (14)
H42C	0.4613	0.1186	0.6550	0.262*	0.459 (14)
C37'	0.5943 (4)	−0.0594 (10)	0.6006 (5)	0.104 (4)	0.541 (14)
H37C	0.5768	−0.0511	0.5589	0.125*	0.541 (14)
H37D	0.5894	−0.1588	0.6115	0.125*	0.541 (14)
C38'	0.6631 (4)	−0.0216 (14)	0.6163 (7)	0.130 (5)	0.541 (14)
H38D	0.6850	−0.0911	0.5992	0.194*	0.541 (14)
H38E	0.6798	−0.0227	0.6578	0.194*	0.541 (14)
H38F	0.6683	0.0731	0.6018	0.194*	0.541 (14)
C39'	0.5838 (8)	0.0310 (16)	0.6946 (3)	0.089 (4)	0.541 (14)
H39C	0.5683	0.1135	0.7116	0.106*	0.541 (14)
H39D	0.6290	0.0378	0.7049	0.106*	0.541 (14)
C40'	0.5656 (15)	−0.107 (2)	0.7209 (8)	0.118 (7)	0.541 (14)
H40D	0.5764	−0.0976	0.7625	0.176*	0.541 (14)
H40E	0.5876	−0.1874	0.7106	0.176*	0.541 (14)
H40F	0.5214	−0.1222	0.7063	0.176*	0.541 (14)
C41'	0.4926 (4)	0.0072 (16)	0.6099 (8)	0.219 (13)	0.541 (14)
H41C	0.4793	−0.0354	0.6416	0.263*	0.541 (14)
H41D	0.4869	−0.0654	0.5796	0.263*	0.541 (14)
C42'	0.4505 (5)	0.1302 (19)	0.5866 (8)	0.146 (7)	0.541 (14)
H42D	0.4094	0.0944	0.5679	0.219*	0.541 (14)
H42E	0.4664	0.1825	0.5589	0.219*	0.541 (14)
H42F	0.4485	0.1934	0.6179	0.219*	0.541 (14)
N6	0.36977 (13)	1.0303 (3)	0.92944 (13)	0.0743 (8)
H6A	0.3832 (15)	1.123 (4)	0.9239 (14)	0.087 (11)*
C43	0.3886 (2)	1.0020 (6)	0.9917 (2)	0.1248 (16)
H43A	0.3696	0.9122	0.9992	0.150*
H43B	0.4336	0.9894	1.0043	0.150*
C44	0.3713 (3)	1.1157 (6)	1.0260 (2)	0.161 (3)
H44A	0.3885	1.0951	1.0666	0.241*
H44B	0.3265	1.1211	1.0173	0.241*
H44C	0.3874	1.2064	1.0169	0.241*
C45	0.4074 (2)	0.9263 (5)	0.9009 (2)	0.1199 (15)
H45A	0.4507	0.9250	0.9240	0.144*
H45B	0.3908	0.8291	0.9008	0.144*
C46	0.4047 (3)	0.9685 (6)	0.8412 (3)	0.178 (3)
H46A	0.4321	0.9076	0.8267	0.268*
H46B	0.4176	1.0675	0.8407	0.268*
H46C	0.3626	0.9581	0.8171	0.268*
C47	0.30173 (17)	1.0267 (4)	0.90080 (18)	0.0915 (11)
H47A	0.2815	1.0986	0.9190	0.110*
H47B	0.2950	1.0544	0.8604	0.110*
C48	0.2710 (2)	0.8863 (5)	0.9027 (2)	0.1220 (16)
H48A	0.2277	0.8930	0.8815	0.183*
H48B	0.2743	0.8609	0.9423	0.183*
H48C	0.2910	0.8134	0.8854	0.183*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0861 (6)	0.1119 (8)	0.0820 (6)	0.0366 (5)	0.0249 (5)	0.0123 (5)
O1	0.0911 (14)	0.0599 (12)	0.0577 (12)	−0.0274 (11)	0.0291 (11)	−0.0051 (10)
O2	0.1102 (18)	0.0819 (15)	0.0644 (13)	−0.0421 (14)	0.0311 (12)	−0.0123 (11)
N1	0.0717 (15)	0.0499 (13)	0.0515 (13)	−0.0145 (11)	0.0224 (11)	−0.0015 (11)
N2	0.1001 (19)	0.0671 (16)	0.0583 (15)	−0.0317 (15)	0.0301 (14)	−0.0039 (13)
C1	0.0540 (15)	0.0441 (15)	0.0581 (16)	−0.0027 (12)	0.0188 (13)	−0.0026 (13)
C2	0.0580 (16)	0.0498 (15)	0.0503 (15)	−0.0038 (13)	0.0183 (12)	−0.0020 (12)
C3	0.087 (2)	0.0629 (19)	0.0557 (18)	−0.0224 (16)	0.0271 (16)	−0.0032 (15)
C4	0.168 (4)	0.108 (3)	0.073 (2)	−0.076 (3)	0.051 (3)	−0.011 (2)
C5	0.0576 (16)	0.0555 (17)	0.0560 (16)	−0.0040 (14)	0.0197 (13)	0.0001 (14)
C6	0.0577 (16)	0.0526 (16)	0.0529 (16)	−0.0037 (13)	0.0137 (13)	−0.0030 (13)
C7	0.0635 (17)	0.0605 (18)	0.0565 (17)	−0.0017 (14)	0.0172 (14)	−0.0008 (14)
C8	0.094 (2)	0.079 (2)	0.059 (2)	−0.0014 (19)	0.0312 (18)	−0.0049 (17)
C9	0.109 (3)	0.089 (3)	0.0523 (19)	−0.010 (2)	0.015 (2)	0.0066 (18)
C10	0.091 (3)	0.091 (3)	0.070 (2)	0.009 (2)	0.0018 (19)	0.018 (2)
C11	0.076 (2)	0.076 (2)	0.069 (2)	0.0067 (18)	0.0135 (16)	0.0057 (17)
C12	0.0569 (15)	0.0502 (16)	0.0519 (16)	−0.0011 (13)	0.0151 (13)	−0.0017 (13)
C13	0.090 (2)	0.077 (2)	0.0627 (19)	−0.0354 (18)	0.0277 (17)	−0.0091 (16)
C14	0.111 (3)	0.102 (3)	0.071 (2)	−0.054 (2)	0.023 (2)	−0.021 (2)
C15	0.079 (2)	0.093 (3)	0.0575 (19)	−0.0190 (19)	0.0168 (16)	−0.0135 (17)
C16	0.0643 (18)	0.085 (2)	0.0550 (18)	−0.0078 (16)	0.0218 (14)	−0.0026 (16)
C17	0.0579 (17)	0.0685 (19)	0.0578 (18)	−0.0125 (14)	0.0181 (14)	−0.0047 (15)
C18	0.138 (4)	0.148 (4)	0.066 (2)	−0.045 (3)	0.027 (2)	−0.033 (3)
Cl2	0.1264 (9)	0.1365 (10)	0.0956 (8)	−0.0007 (7)	0.0324 (6)	−0.0470 (7)
O3	0.0532 (11)	0.0551 (12)	0.0817 (14)	0.0019 (9)	0.0161 (10)	0.0218 (10)
O4	0.0595 (13)	0.0776 (15)	0.1142 (19)	0.0033 (11)	0.0141 (12)	0.0423 (14)
N3	0.0501 (12)	0.0478 (13)	0.0534 (13)	0.0014 (10)	0.0143 (10)	0.0100 (10)
N4	0.0562 (14)	0.0639 (15)	0.0669 (15)	−0.0011 (12)	0.0176 (12)	0.0191 (12)
C19	0.0516 (15)	0.0432 (14)	0.0472 (14)	0.0007 (12)	0.0118 (12)	0.0015 (12)
C20	0.0514 (15)	0.0483 (15)	0.0515 (15)	−0.0013 (12)	0.0110 (12)	0.0008 (13)
C21	0.0543 (17)	0.0616 (18)	0.0611 (17)	−0.0024 (14)	0.0161 (14)	0.0088 (14)
C22	0.065 (2)	0.112 (3)	0.111 (3)	−0.006 (2)	0.0258 (19)	0.046 (2)
C23	0.0534 (16)	0.0586 (18)	0.0597 (17)	0.0023 (14)	0.0122 (13)	0.0043 (14)
C24	0.0580 (17)	0.0601 (18)	0.0568 (17)	0.0035 (14)	0.0146 (14)	0.0103 (14)
C25	0.074 (2)	0.073 (2)	0.0638 (19)	0.0072 (17)	0.0214 (16)	0.0040 (16)
C26	0.074 (2)	0.088 (3)	0.094 (3)	0.0119 (19)	0.040 (2)	0.019 (2)
C27	0.062 (2)	0.091 (3)	0.096 (3)	0.0010 (19)	0.012 (2)	0.014 (2)
C28	0.073 (2)	0.087 (3)	0.088 (2)	−0.0092 (19)	0.0030 (19)	−0.004 (2)
C29	0.0543 (18)	0.073 (2)	0.079 (2)	−0.0037 (15)	0.0066 (15)	−0.0006 (17)
C30	0.0542 (15)	0.0449 (15)	0.0464 (14)	0.0019 (12)	0.0106 (12)	0.0022 (12)
C31	0.0662 (19)	0.0678 (19)	0.0591 (18)	0.0086 (15)	0.0168 (14)	0.0188 (15)
C32	0.073 (2)	0.083 (2)	0.074 (2)	0.0193 (18)	0.0147 (17)	0.0346 (18)
C33	0.0613 (19)	0.084 (2)	0.080 (2)	0.0191 (17)	0.0160 (16)	0.0242 (18)
C34	0.0596 (18)	0.076 (2)	0.085 (2)	0.0119 (16)	0.0248 (16)	0.0258 (18)
C35	0.0625 (18)	0.0616 (18)	0.0639 (18)	0.0090 (14)	0.0174 (14)	0.0186 (15)
C36	0.080 (3)	0.146 (4)	0.127 (4)	0.045 (3)	0.030 (2)	0.060 (3)
N5	0.103 (2)	0.0573 (16)	0.0794 (19)	−0.0226 (15)	0.0339 (17)	−0.0025 (14)
C37	0.37 (3)	0.114 (12)	0.26 (3)	0.106 (15)	0.24 (2)	0.106 (14)
C38	0.32 (3)	0.25 (2)	0.154 (18)	0.18 (2)	0.137 (18)	0.106 (16)
C39	0.142 (13)	0.072 (9)	0.073 (7)	−0.046 (9)	0.029 (6)	−0.008 (5)
C40	0.30 (4)	0.058 (8)	0.095 (12)	−0.055 (17)	0.072 (17)	−0.018 (7)
C41	0.167 (16)	0.070 (8)	0.052 (5)	−0.078 (9)	0.034 (7)	−0.020 (5)
C42	0.176 (17)	0.105 (11)	0.30 (3)	−0.007 (10)	0.162 (19)	0.039 (15)
C37'	0.195 (12)	0.054 (5)	0.086 (6)	−0.014 (6)	0.078 (6)	0.010 (4)
C38'	0.130 (8)	0.108 (7)	0.175 (14)	0.024 (6)	0.084 (9)	0.078 (8)
C39'	0.129 (9)	0.065 (6)	0.075 (6)	−0.003 (6)	0.033 (5)	0.005 (4)
C40'	0.179 (12)	0.093 (12)	0.097 (11)	0.018 (10)	0.066 (10)	0.026 (9)
C41'	0.141 (16)	0.189 (19)	0.28 (2)	−0.066 (14)	−0.030 (13)	0.113 (17)
C42'	0.077 (7)	0.219 (17)	0.152 (12)	−0.020 (8)	0.047 (7)	0.050 (10)
N6	0.0705 (17)	0.0564 (17)	0.091 (2)	−0.0018 (14)	0.0127 (14)	0.0182 (15)
C43	0.130 (4)	0.115 (4)	0.116 (4)	−0.006 (3)	0.012 (3)	0.050 (3)
C44	0.278 (8)	0.112 (4)	0.127 (4)	0.051 (5)	0.114 (5)	0.019 (3)
C45	0.129 (4)	0.076 (3)	0.167 (5)	0.005 (3)	0.062 (3)	0.003 (3)
C46	0.267 (8)	0.115 (4)	0.198 (7)	−0.030 (5)	0.139 (6)	−0.029 (4)
C47	0.085 (2)	0.084 (3)	0.100 (3)	−0.013 (2)	0.016 (2)	0.006 (2)
C48	0.121 (3)	0.106 (3)	0.152 (4)	−0.033 (3)	0.058 (3)	−0.030 (3)

Geometric parameters (Å, º)

Cl1—C7	1.737 (3)	C34—C35	1.377 (4)
O1—C1	1.244 (3)	C34—H34	0.9300
O2—C5	1.237 (3)	C35—H35	0.9300
N1—C1	1.386 (3)	C36—H36A	0.9600
N1—N2	1.395 (3)	C36—H36B	0.9600
N1—C12	1.405 (3)	C36—H36C	0.9600
N2—C3	1.301 (4)	N5—C41'	1.462 (8)
C1—C2	1.431 (4)	N5—C37	1.469 (8)
C2—C5	1.410 (4)	N5—C39'	1.474 (7)
C2—C3	1.416 (4)	N5—C39	1.481 (8)
C3—C4	1.501 (4)	N5—C41	1.492 (7)
C4—H4A	0.9600	N5—C37'	1.501 (7)
C4—H4B	0.9600	N5—H5A	0.9001
C4—H4C	0.9600	N5—H5B	0.9001
C5—C6	1.511 (4)	C37—C38	1.491 (10)
C6—C7	1.370 (4)	C37—H37A	0.9700
C6—C11	1.391 (4)	C37—H37B	0.9700
C7—C8	1.375 (4)	C38—H38A	0.9600
C8—C9	1.372 (5)	C38—H38B	0.9600
C8—H8	0.9300	C38—H38C	0.9600
C9—C10	1.362 (5)	C39—C40	1.521 (9)
C9—H9	0.9300	C39—H39A	0.9700
C10—C11	1.375 (5)	C39—H39B	0.9700
C10—H10	0.9300	C40—H40A	0.9600
C11—H11	0.9300	C40—H40B	0.9600
C12—C13	1.374 (4)	C40—H40C	0.9600
C12—C17	1.387 (4)	C41—C42	1.523 (9)
C13—C14	1.365 (4)	C41—H41A	0.9700
C13—H13	0.9300	C41—H41B	0.9700
C14—C15	1.386 (5)	C42—H42A	0.9600
C14—H14	0.9300	C42—H42B	0.9600
C15—C16	1.365 (4)	C42—H42C	0.9600
C15—C18	1.517 (5)	C37'—C38'	1.512 (9)
C16—C17	1.376 (4)	C37'—H37C	0.9700
C16—H16	0.9300	C37'—H37D	0.9700
C17—H17	0.9300	C38'—H38D	0.9600
C18—H18A	0.9600	C38'—H38E	0.9600
C18—H18B	0.9600	C38'—H38F	0.9600
C18—H18C	0.9600	C39'—C40'	1.523 (9)
Cl2—C25	1.721 (3)	C39'—H39C	0.9700
O3—C19	1.246 (3)	C39'—H39D	0.9700
O4—C23	1.237 (3)	C40'—H40D	0.9600
N3—C19	1.382 (3)	C40'—H40E	0.9600
N3—N4	1.394 (3)	C40'—H40F	0.9600
N3—C30	1.410 (3)	C41'—C42'	1.482 (9)
N4—C21	1.304 (3)	C41'—H41C	0.9700
C19—C20	1.430 (4)	C41'—H41D	0.9700
C20—C23	1.407 (4)	C42'—H42D	0.9600
C20—C21	1.422 (4)	C42'—H42E	0.9600
C21—C22	1.495 (4)	C42'—H42F	0.9600
C22—H22A	0.9600	N6—C43	1.457 (5)
C22—H22B	0.9600	N6—C47	1.481 (4)
C22—H22C	0.9600	N6—C45	1.549 (5)
C23—C24	1.515 (4)	N6—H6A	0.93 (4)
C24—C25	1.360 (4)	C43—C44	1.447 (6)
C24—C29	1.418 (4)	C43—H43A	0.9700
C25—C26	1.409 (5)	C43—H43B	0.9700
C26—C27	1.352 (5)	C44—H44A	0.9600
C26—H26	0.9300	C44—H44B	0.9600
C27—C28	1.366 (5)	C44—H44C	0.9600
C27—H27	0.9300	C45—C46	1.466 (7)
C28—C29	1.359 (4)	C45—H45A	0.9700
C28—H28	0.9300	C45—H45B	0.9700
C29—H29	0.9300	C46—H46A	0.9600
C30—C31	1.379 (4)	C46—H46B	0.9600
C30—C35	1.384 (4)	C46—H46C	0.9600
C31—C32	1.367 (4)	C47—C48	1.473 (5)
C31—H31	0.9300	C47—H47A	0.9700
C32—C33	1.378 (4)	C47—H47B	0.9700
C32—H32	0.9300	C48—H48A	0.9600
C33—C34	1.374 (4)	C48—H48B	0.9600
C33—C36	1.516 (5)	C48—H48C	0.9600
C1—N1—N2	111.7 (2)	H36A—C36—H36C	109.5
C1—N1—C12	130.1 (2)	H36B—C36—H36C	109.5
N2—N1—C12	118.1 (2)	C41'—N5—C37	117.6 (11)
C3—N2—N1	105.6 (2)	C41'—N5—C39'	113.4 (8)
O1—C1—N1	123.6 (2)	C37—N5—C39'	91.4 (10)
O1—C1—C2	131.6 (2)	C41'—N5—C39	96.5 (11)
N1—C1—C2	104.7 (2)	C37—N5—C39	111.9 (8)
C5—C2—C3	130.9 (2)	C39'—N5—C39	21.7 (10)
C5—C2—C1	124.2 (2)	C41'—N5—C41	14.7 (9)
C3—C2—C1	104.9 (2)	C37—N5—C41	111.9 (8)
N2—C3—C2	113.1 (2)	C39'—N5—C41	128.1 (8)
N2—C3—C4	117.4 (3)	C39—N5—C41	111.0 (7)
C2—C3—C4	129.6 (3)	C41'—N5—C37'	108.8 (7)
C3—C4—H4A	109.5	C37—N5—C37'	20.9 (8)
C3—C4—H4B	109.5	C39'—N5—C37'	112.2 (7)
H4A—C4—H4B	109.5	C39—N5—C37'	132.9 (8)
C3—C4—H4C	109.5	C41—N5—C37'	99.0 (6)
H4A—C4—H4C	109.5	C41'—N5—H5A	114.3
H4B—C4—H4C	109.5	C37—N5—H5A	109.1
O2—C5—C2	124.5 (3)	C39'—N5—H5A	108.6
O2—C5—C6	116.4 (2)	C39—N5—H5A	106.3
C2—C5—C6	119.1 (2)	C41—N5—H5A	106.2
C7—C6—C11	117.5 (3)	C37'—N5—H5A	98.7
C7—C6—C5	123.2 (3)	C41'—N5—H5B	106.5
C11—C6—C5	119.3 (3)	C37—N5—H5B	118.1
C6—C7—C8	122.5 (3)	C39'—N5—H5B	108.9
C6—C7—Cl1	119.4 (2)	C39—N5—H5B	103.2
C8—C7—Cl1	118.1 (2)	C41—N5—H5B	99.8
C9—C8—C7	118.7 (3)	C37'—N5—H5B	106.6
C9—C8—H8	120.6	H5A—N5—H5B	9.3
C7—C8—H8	120.6	N5—C37—C38	114.3 (11)
C10—C9—C8	120.2 (3)	N5—C37—H37A	108.7
C10—C9—H9	119.9	C38—C37—H37A	108.7
C8—C9—H9	119.9	N5—C37—H37B	108.7
C9—C10—C11	120.6 (3)	C38—C37—H37B	108.7
C9—C10—H10	119.7	H37A—C37—H37B	107.6
C11—C10—H10	119.7	N5—C39—C40	114.1 (10)
C10—C11—C6	120.3 (3)	N5—C39—H39A	108.7
C10—C11—H11	119.8	C40—C39—H39A	108.7
C6—C11—H11	119.8	N5—C39—H39B	108.7
C13—C12—C17	118.3 (3)	C40—C39—H39B	108.7
C13—C12—N1	119.7 (2)	H39A—C39—H39B	107.6
C17—C12—N1	122.0 (2)	N5—C41—C42	107.9 (9)
C14—C13—C12	120.8 (3)	N5—C41—H41A	110.1
C14—C13—H13	119.6	C42—C41—H41A	110.1
C12—C13—H13	119.6	N5—C41—H41B	110.1
C13—C14—C15	122.0 (3)	C42—C41—H41B	110.1
C13—C14—H14	119.0	H41A—C41—H41B	108.4
C15—C14—H14	119.0	N5—C37'—C38'	111.1 (7)
C16—C15—C14	116.3 (3)	N5—C37'—H37C	109.4
C16—C15—C18	122.2 (3)	C38'—C37'—H37C	109.4
C14—C15—C18	121.5 (3)	N5—C37'—H37D	109.4
C15—C16—C17	123.0 (3)	C38'—C37'—H37D	109.4
C15—C16—H16	118.5	H37C—C37'—H37D	108.0
C17—C16—H16	118.5	C37'—C38'—H38D	109.5
C16—C17—C12	119.5 (3)	C37'—C38'—H38E	109.5
C16—C17—H17	120.3	H38D—C38'—H38E	109.5
C12—C17—H17	120.3	C37'—C38'—H38F	109.5
C15—C18—H18A	109.5	H38D—C38'—H38F	109.5
C15—C18—H18B	109.5	H38E—C38'—H38F	109.5
H18A—C18—H18B	109.5	N5—C39'—C40'	113.9 (9)
C15—C18—H18C	109.5	N5—C39'—H39C	108.8
H18A—C18—H18C	109.5	C40'—C39'—H39C	108.8
H18B—C18—H18C	109.5	N5—C39'—H39D	108.8
C19—N3—N4	112.0 (2)	C40'—C39'—H39D	108.8
C19—N3—C30	129.7 (2)	H39C—C39'—H39D	107.7
N4—N3—C30	118.3 (2)	C39'—C40'—H40D	109.5
C21—N4—N3	105.5 (2)	C39'—C40'—H40E	109.5
O3—C19—N3	123.9 (2)	H40D—C40'—H40E	109.5
O3—C19—C20	131.4 (2)	C39'—C40'—H40F	109.5
N3—C19—C20	104.7 (2)	H40D—C40'—H40F	109.5
C23—C20—C21	131.4 (2)	H40E—C40'—H40F	109.5
C23—C20—C19	123.6 (2)	N5—C41'—C42'	117.0 (9)
C21—C20—C19	105.0 (2)	N5—C41'—H41C	108.0
N4—C21—C20	112.7 (2)	C42'—C41'—H41C	108.0
N4—C21—C22	117.7 (3)	N5—C41'—H41D	108.0
C20—C21—C22	129.5 (3)	C42'—C41'—H41D	108.0
C21—C22—H22A	109.5	H41C—C41'—H41D	107.3
C21—C22—H22B	109.5	C41'—C42'—H42D	109.5
H22A—C22—H22B	109.5	C41'—C42'—H42E	109.5
C21—C22—H22C	109.5	H42D—C42'—H42E	109.5
H22A—C22—H22C	109.5	C41'—C42'—H42F	109.5
H22B—C22—H22C	109.5	H42D—C42'—H42F	109.5
O4—C23—C20	124.3 (3)	H42E—C42'—H42F	109.5
O4—C23—C24	115.8 (2)	C43—N6—C47	116.2 (3)
C20—C23—C24	119.8 (2)	C43—N6—C45	107.4 (3)
C25—C24—C29	118.8 (3)	C47—N6—C45	112.8 (3)
C25—C24—C23	122.7 (3)	C43—N6—H6A	107 (2)
C29—C24—C23	118.3 (3)	C47—N6—H6A	106 (2)
C24—C25—C26	121.2 (3)	C45—N6—H6A	106 (2)
C24—C25—Cl2	119.7 (3)	C44—C43—N6	113.7 (4)
C26—C25—Cl2	119.1 (3)	C44—C43—H43A	108.8
C27—C26—C25	118.5 (3)	N6—C43—H43A	108.8
C27—C26—H26	120.8	C44—C43—H43B	108.8
C25—C26—H26	120.8	N6—C43—H43B	108.8
C26—C27—C28	121.2 (3)	H43A—C43—H43B	107.7
C26—C27—H27	119.4	C43—C44—H44A	109.5
C28—C27—H27	119.4	C43—C44—H44B	109.5
C29—C28—C27	121.3 (4)	H44A—C44—H44B	109.5
C29—C28—H28	119.3	C43—C44—H44C	109.5
C27—C28—H28	119.3	H44A—C44—H44C	109.5
C28—C29—C24	119.0 (3)	H44B—C44—H44C	109.5
C28—C29—H29	120.5	C46—C45—N6	112.3 (4)
C24—C29—H29	120.5	C46—C45—H45A	109.1
C31—C30—C35	118.3 (3)	N6—C45—H45A	109.1
C31—C30—N3	120.0 (2)	C46—C45—H45B	109.1
C35—C30—N3	121.7 (2)	N6—C45—H45B	109.1
C32—C31—C30	120.4 (3)	H45A—C45—H45B	107.9
C32—C31—H31	119.8	C45—C46—H46A	109.5
C30—C31—H31	119.8	C45—C46—H46B	109.5
C31—C32—C33	122.3 (3)	H46A—C46—H46B	109.5
C31—C32—H32	118.8	C45—C46—H46C	109.5
C33—C32—H32	118.8	H46A—C46—H46C	109.5
C34—C33—C32	116.7 (3)	H46B—C46—H46C	109.5
C34—C33—C36	121.7 (3)	C48—C47—N6	115.4 (3)
C32—C33—C36	121.6 (3)	C48—C47—H47A	108.4
C33—C34—C35	122.2 (3)	N6—C47—H47A	108.4
C33—C34—H34	118.9	C48—C47—H47B	108.4
C35—C34—H34	118.9	N6—C47—H47B	108.4
C34—C35—C30	120.1 (3)	H47A—C47—H47B	107.5
C34—C35—H35	120.0	C47—C48—H48A	109.5
C30—C35—H35	120.0	C47—C48—H48B	109.5
C33—C36—H36A	109.5	H48A—C48—H48B	109.5
C33—C36—H36B	109.5	C47—C48—H48C	109.5
H36A—C36—H36B	109.5	H48A—C48—H48C	109.5
C33—C36—H36C	109.5	H48B—C48—H48C	109.5
C1—N1—N2—C3	0.5 (3)	C21—C20—C23—C24	7.3 (5)
C12—N1—N2—C3	−177.8 (3)	C19—C20—C23—C24	−172.6 (2)
N2—N1—C1—O1	178.9 (3)	O4—C23—C24—C25	86.2 (4)
C12—N1—C1—O1	−3.2 (5)	C20—C23—C24—C25	−97.0 (4)
N2—N1—C1—C2	−0.4 (3)	O4—C23—C24—C29	−89.1 (3)
C12—N1—C1—C2	177.5 (3)	C20—C23—C24—C29	87.7 (3)
O1—C1—C2—C5	0.9 (5)	C29—C24—C25—C26	0.7 (5)
N1—C1—C2—C5	−179.9 (3)	C23—C24—C25—C26	−174.6 (3)
O1—C1—C2—C3	−179.0 (3)	C29—C24—C25—Cl2	−179.4 (2)
N1—C1—C2—C3	0.2 (3)	C23—C24—C25—Cl2	5.3 (4)
N1—N2—C3—C2	−0.3 (4)	C24—C25—C26—C27	−1.3 (5)
N1—N2—C3—C4	−179.1 (3)	Cl2—C25—C26—C27	178.8 (3)
C5—C2—C3—N2	−179.8 (3)	C25—C26—C27—C28	0.5 (5)
C1—C2—C3—N2	0.0 (4)	C26—C27—C28—C29	0.9 (6)
C5—C2—C3—C4	−1.3 (6)	C27—C28—C29—C24	−1.4 (5)
C1—C2—C3—C4	178.6 (4)	C25—C24—C29—C28	0.6 (5)
C3—C2—C5—O2	177.8 (3)	C23—C24—C29—C28	176.1 (3)
C1—C2—C5—O2	−2.0 (5)	C19—N3—C30—C31	−169.4 (3)
C3—C2—C5—C6	−2.7 (5)	N4—N3—C30—C31	12.4 (4)
C1—C2—C5—C6	177.4 (2)	C19—N3—C30—C35	12.0 (4)
O2—C5—C6—C7	−91.5 (3)	N4—N3—C30—C35	−166.2 (2)
C2—C5—C6—C7	89.0 (3)	C35—C30—C31—C32	2.3 (5)
O2—C5—C6—C11	87.0 (3)	N3—C30—C31—C32	−176.3 (3)
C2—C5—C6—C11	−92.4 (3)	C30—C31—C32—C33	0.4 (5)
C11—C6—C7—C8	0.5 (5)	C31—C32—C33—C34	−3.0 (6)
C5—C6—C7—C8	179.1 (3)	C31—C32—C33—C36	175.3 (4)
C11—C6—C7—Cl1	179.8 (2)	C32—C33—C34—C35	3.1 (5)
C5—C6—C7—Cl1	−1.7 (4)	C36—C33—C34—C35	−175.2 (4)
C6—C7—C8—C9	−0.4 (5)	C33—C34—C35—C30	−0.6 (5)
Cl1—C7—C8—C9	−179.7 (3)	C31—C30—C35—C34	−2.2 (4)
C7—C8—C9—C10	0.4 (5)	N3—C30—C35—C34	176.4 (3)
C8—C9—C10—C11	−0.5 (6)	C41'—N5—C37—C38	117 (2)
C9—C10—C11—C6	0.6 (5)	C39'—N5—C37—C38	−126 (2)
C7—C6—C11—C10	−0.6 (5)	C39—N5—C37—C38	−133 (2)
C5—C6—C11—C10	−179.2 (3)	C41—N5—C37—C38	102 (2)
C1—N1—C12—C13	173.7 (3)	C37'—N5—C37—C38	47 (3)
N2—N1—C12—C13	−8.5 (4)	C41'—N5—C39—C40	70 (2)
C1—N1—C12—C17	−6.6 (4)	C37—N5—C39—C40	−53 (2)
N2—N1—C12—C17	171.3 (3)	C39'—N5—C39—C40	−73 (4)
C17—C12—C13—C14	−2.8 (5)	C41—N5—C39—C40	72 (2)
N1—C12—C13—C14	177.0 (3)	C37'—N5—C39—C40	−53 (2)
C12—C13—C14—C15	0.1 (6)	C41'—N5—C41—C42	54 (3)
C13—C14—C15—C16	3.4 (6)	C37—N5—C41—C42	170.0 (12)
C13—C14—C15—C18	−176.1 (4)	C39'—N5—C41—C42	59.6 (15)
C14—C15—C16—C17	−4.4 (5)	C39—N5—C41—C42	44.2 (14)
C18—C15—C16—C17	175.2 (4)	C37'—N5—C41—C42	−172.9 (11)
C15—C16—C17—C12	1.8 (5)	C41'—N5—C37'—C38'	174.4 (11)
C13—C12—C17—C16	1.9 (4)	C37—N5—C37'—C38'	−67 (3)
N1—C12—C17—C16	−177.9 (3)	C39'—N5—C37'—C38'	−59.2 (12)
C19—N3—N4—C21	−1.7 (3)	C39—N5—C37'—C38'	−67.1 (14)
C30—N3—N4—C21	176.8 (2)	C41—N5—C37'—C38'	163.1 (10)
N4—N3—C19—O3	−178.5 (2)	C41'—N5—C39'—C40'	49.6 (18)
C30—N3—C19—O3	3.2 (4)	C37—N5—C39'—C40'	−71.5 (17)
N4—N3—C19—C20	1.8 (3)	C39—N5—C39'—C40'	90 (3)
C30—N3—C19—C20	−176.5 (2)	C41—N5—C39'—C40'	48.1 (19)
O3—C19—C20—C23	−0.9 (5)	C37'—N5—C39'—C40'	−74.2 (17)
N3—C19—C20—C23	178.8 (2)	C37—N5—C41'—C42'	−146.4 (17)
O3—C19—C20—C21	179.2 (3)	C39'—N5—C41'—C42'	108.6 (18)
N3—C19—C20—C21	−1.1 (3)	C39—N5—C41'—C42'	94.7 (19)
N3—N4—C21—C20	0.9 (3)	C41—N5—C41'—C42'	−76 (4)
N3—N4—C21—C22	178.5 (3)	C37'—N5—C41'—C42'	−125.8 (17)
C23—C20—C21—N4	−179.8 (3)	C47—N6—C43—C44	−69.0 (5)
C19—C20—C21—N4	0.1 (3)	C45—N6—C43—C44	163.6 (4)
C23—C20—C21—C22	3.0 (5)	C43—N6—C45—C46	−165.4 (4)
C19—C20—C21—C22	−177.1 (3)	C47—N6—C45—C46	65.2 (5)
C21—C20—C23—O4	−176.2 (3)	C43—N6—C47—C48	−62.7 (5)
C19—C20—C23—O4	3.9 (5)	C45—N6—C47—C48	62.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O1	0.90	1.90	2.703 (3)	147
N5—H5A···O2	0.90	2.39	3.029 (3)	128
N6—H6A···O3^i	0.93 (4)	1.94 (4)	2.744 (3)	144 (3)
N6—H6A···O4^i	0.93 (4)	2.27 (3)	2.943 (4)	129 (3)

Symmetry code: (i) x, y+1, z.