(Carbazol-9-ido-κN)di­chlorido­(η⁵:η¹-2,3,4,5-tetra­methyl­penta­fulvene)tantalum(V)

The reaction of (η⁵:η¹-2,3,4,5-tetra­methyl­penta­fulvene)tantalum(V) dicarbazolide chloride (1) with etheric HCl results in the formation of the title compound (2), [Ta(C₁₀H₁₄)(C₁₂H₈N)Cl₂]. The Ta^V atom has a distorted tetra­hedral coordination environment in a three-legged piano-stool fashion. The conformation of the penta­fulvene exocyclic C atom to the three other ligands is staggered and not eclipsed, as found in the crystal structure of 1. Inter­molecular inter­actions include π–π stacking, H...π inter­actions and weak C—H...Cl hydrogen bonds.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• R factor = 0.016
• wR factor = 0.044
• Data-to-parameter ratio = 46.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         26 Report
              Ta1       Cl1       Cl2       N1        C1                  etc.

Author Response: Apparently, checkCIF is not able to handle the anharmonically refined displacement parameters of the Ta1 atom correctly. This is the reason for this alert, which otherwise is meaningless.

Alert level B
PLAT210_ALERT_3_B No Anisotropic ADP's Found in CIF ..............     Please Check

Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT073_ALERT_1_G H-atoms ref, but _hydrogen_treatment Reported as     constr Check
PLAT343_ALERT_2_G Unusual sp?      Angle Range in Main Residue for         C1 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H8B      ..CL2      .       2.91 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H15      ..CL2      .       2.86 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H18      ..CL1      .       3.13 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H18      ..CL2      .       2.85 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H19      ..CL1      .       3.08 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H20      ..CL1      .       2.95 Ang.
PLAT769_ALERT_4_G CIF Embedded explicitly supplied scattering data     Please Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT872_ALERT_4_G ALERTS Related to Anharmonic Refine   Suppressed          ! Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...         44 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info
PLAT982_ALERT_1_G The Ta-f'=   -0.5847 Deviates from  IT-value =      -0.7052 Check
PLAT983_ALERT_1_G The Cl-f"=    0.1603 Deviates from  IT-Value =       0.1585 Check
PLAT983_ALERT_1_G The Ta-f"=    6.5815 Deviates from  IT-Value =       6.5227 Check

   1 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  19 ALERT level G = General information/check it is not something unexpected

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   9 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: Olex2 (Bourhis et al., 2015); molecular graphics: Olex2 (Bourhis et al., 2015); software used to prepare material for publication: Olex2 (Bourhis et al., 2015).

(Carbazol-9-ido-κN)dichlorido(η⁵:η¹-2,3,4,5-tetramethylpentafulvene)tantalum(V)

Crystal data

[Ta(C10H14)(C12H8N)Cl2]	F(000) = 1072.380
Mr = 552.28	Dx = 1.888 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.8422 (12) Å	Cell parameters from 9727 reflections
b = 7.3442 (5) Å	θ = 2.6–40.3°
c = 16.7885 (11) Å	µ = 5.94 mm^−1
β = 117.950 (2)°	T = 100 K
V = 1943.3 (2) Å^3	Block, red
Z = 4	0.12 × 0.11 × 0.05 mm

Data collection

Bruker Photon III CPAD diffractometer	11363 reflections with I ≥ 2θ(I)
φ and ω scans	Rint = 0.043
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 40.3°, θmin = 2.4°
Tmin = 0.511, Tmax = 0.651	h = −32→32
128718 measured reflections	k = −13→13
12240 independent reflections	l = −30→30

Refinement

Refinement on F^2	35 constraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.016	H-atom parameters constrained
wR(F^2) = 0.044	w = 1/[σ^2(Fo^2) + (0.0164P)^2 + 1.1947P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = −0.001
12240 reflections	Δρmax = 1.28 e Å^−3
264 parameters	Δρmin = −1.24 e Å^−3
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ta1	0.278227 (6)	0.666931 (14)	0.609660 (6)	0.01317 (5)
Cl1	0.392598 (18)	0.63539 (4)	0.754919 (18)	0.02060 (5)
Cl2	0.188124 (17)	0.54264 (4)	0.666091 (19)	0.01858 (5)
N1	0.26155 (5)	0.45000 (13)	0.52677 (6)	0.01386 (12)
C1	0.31669 (7)	0.90414 (15)	0.55660 (7)	0.01712 (16)
C2	0.30629 (8)	0.98409 (15)	0.62994 (8)	0.01875 (17)
C3	0.21917 (8)	0.97380 (15)	0.60722 (8)	0.01822 (17)
C4	0.17348 (7)	0.89795 (15)	0.51906 (8)	0.01707 (16)
C5	0.23188 (7)	0.85726 (15)	0.48611 (7)	0.01642 (16)
C6	0.38444 (7)	0.77942 (18)	0.57472 (8)	0.01934 (18)
H6a	0.44053 (7)	0.80823 (18)	0.62603 (8)	0.0232 (2)*
H6b	0.38711 (7)	0.72515 (18)	0.52213 (8)	0.0232 (2)*
C7	0.37542 (10)	1.06857 (19)	0.71354 (9)	0.0256 (2)
H7a	0.3710 (6)	1.20151 (19)	0.7085 (4)	0.0384 (3)*
H7b	0.3696 (6)	1.0293 (16)	0.76616 (15)	0.0384 (3)*
H7c	0.43078 (10)	1.0301 (16)	0.7205 (5)	0.0384 (3)*
C8	0.17969 (10)	1.03756 (19)	0.66363 (10)	0.0256 (2)
H8a	0.22378 (17)	1.052 (2)	0.7263 (2)	0.0384 (3)*
H8b	0.1516 (9)	1.1549 (10)	0.6408 (7)	0.0384 (3)*
H8c	0.1378 (7)	0.9479 (10)	0.6608 (8)	0.0384 (3)*
C9	0.07868 (8)	0.88368 (19)	0.46864 (9)	0.0225 (2)
H9a	0.06216 (9)	0.8053 (15)	0.4158 (5)	0.0337 (3)*
H9b	0.05769 (11)	0.8313 (17)	0.5081 (3)	0.0337 (3)*
H9c	0.05421 (9)	1.0052 (3)	0.4490 (8)	0.0337 (3)*
C10	0.21185 (8)	0.78707 (18)	0.39424 (7)	0.01993 (18)
H10a	0.2608 (3)	0.7197 (15)	0.39786 (18)	0.0299 (3)*
H10b	0.1626 (5)	0.7060 (14)	0.3724 (4)	0.0299 (3)*
H10c	0.1992 (8)	0.8897 (2)	0.3526 (2)	0.0299 (3)*
C11	0.18132 (6)	0.39330 (14)	0.45672 (7)	0.01415 (14)
C12	0.10037 (7)	0.42830 (16)	0.44654 (8)	0.01689 (16)
H12	0.09314 (7)	0.49491 (16)	0.49097 (8)	0.02027 (19)*
C13	0.03042 (7)	0.36314 (17)	0.36962 (8)	0.01928 (18)
H13	−0.02505 (7)	0.38633 (17)	0.36168 (8)	0.0231 (2)*
C14	0.04027 (7)	0.26427 (18)	0.30388 (8)	0.01979 (18)
H14	−0.00838 (7)	0.22206 (18)	0.25180 (8)	0.0238 (2)*
C15	0.12064 (7)	0.22749 (16)	0.31426 (7)	0.01721 (16)
H15	0.12740 (7)	0.16001 (16)	0.26977 (7)	0.02065 (19)*
C16	0.19144 (6)	0.29109 (14)	0.39104 (7)	0.01395 (14)
C17	0.28193 (6)	0.27368 (14)	0.42311 (7)	0.01377 (14)
C18	0.32964 (7)	0.18151 (15)	0.38960 (8)	0.01630 (16)
H18	0.30272 (7)	0.12006 (15)	0.33329 (8)	0.01957 (19)*
C19	0.41763 (7)	0.18178 (16)	0.44069 (8)	0.01833 (17)
H19	0.45125 (7)	0.12051 (16)	0.41887 (8)	0.0220 (2)*
C20	0.45710 (7)	0.27159 (17)	0.52402 (8)	0.01864 (17)
H20	0.51720 (7)	0.26906 (17)	0.55802 (8)	0.0224 (2)*
C21	0.41031 (7)	0.36438 (16)	0.55811 (7)	0.01696 (16)
H21	0.43742 (7)	0.42398 (16)	0.61491 (7)	0.02035 (19)*
C22	0.32212 (6)	0.36687 (14)	0.50595 (7)	0.01367 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ta1	0.01119 (6)	0.01644 (8)	0.01408 (7)	0.00048 (3)	0.00775 (5)	0.00024 (3)
Cl1	0.01654 (10)	0.02804 (12)	0.01445 (9)	−0.00206 (9)	0.00495 (8)	0.00104 (8)
Cl2	0.01698 (10)	0.02367 (11)	0.01952 (10)	0.00074 (8)	0.01225 (8)	0.00389 (8)
N1	0.0117 (3)	0.0159 (3)	0.0152 (3)	0.0003 (2)	0.0074 (2)	−0.0015 (2)
C1	0.0197 (4)	0.0167 (4)	0.0181 (4)	−0.0030 (3)	0.0115 (3)	0.0003 (3)
C2	0.0256 (5)	0.0139 (4)	0.0200 (4)	−0.0037 (3)	0.0135 (4)	−0.0021 (3)
C3	0.0228 (4)	0.0155 (4)	0.0200 (4)	0.0021 (3)	0.0130 (4)	−0.0002 (3)
C4	0.0187 (4)	0.0159 (4)	0.0182 (4)	0.0030 (3)	0.0100 (3)	0.0023 (3)
C5	0.0192 (4)	0.0166 (4)	0.0155 (4)	0.0004 (3)	0.0098 (3)	0.0016 (3)
C6	0.0165 (4)	0.0244 (5)	0.0207 (4)	−0.0033 (3)	0.0118 (3)	−0.0016 (4)
C7	0.0300 (6)	0.0238 (5)	0.0232 (5)	−0.0088 (4)	0.0127 (4)	−0.0072 (4)
C8	0.0324 (6)	0.0230 (5)	0.0292 (6)	0.0029 (4)	0.0210 (5)	−0.0041 (4)
C9	0.0192 (4)	0.0235 (5)	0.0250 (5)	0.0062 (4)	0.0106 (4)	0.0036 (4)
C10	0.0243 (5)	0.0215 (4)	0.0153 (4)	0.0007 (4)	0.0105 (4)	0.0018 (3)
C11	0.0122 (3)	0.0154 (4)	0.0151 (3)	0.0006 (3)	0.0066 (3)	−0.0001 (3)
C12	0.0128 (3)	0.0197 (4)	0.0194 (4)	0.0011 (3)	0.0086 (3)	−0.0007 (3)
C13	0.0121 (4)	0.0240 (5)	0.0207 (4)	0.0016 (3)	0.0068 (3)	0.0011 (4)
C14	0.0135 (4)	0.0251 (5)	0.0180 (4)	−0.0009 (3)	0.0050 (3)	−0.0003 (4)
C15	0.0153 (4)	0.0204 (4)	0.0146 (4)	−0.0005 (3)	0.0060 (3)	−0.0010 (3)
C16	0.0126 (3)	0.0154 (3)	0.0144 (3)	0.0004 (3)	0.0068 (3)	−0.0001 (3)
C17	0.0124 (3)	0.0156 (4)	0.0142 (3)	0.0009 (3)	0.0069 (3)	−0.0001 (3)
C18	0.0154 (4)	0.0195 (4)	0.0162 (4)	0.0014 (3)	0.0093 (3)	−0.0011 (3)
C19	0.0154 (4)	0.0232 (5)	0.0194 (4)	0.0031 (3)	0.0106 (3)	0.0000 (3)
C20	0.0128 (4)	0.0240 (5)	0.0195 (4)	0.0034 (3)	0.0079 (3)	0.0006 (3)
C21	0.0121 (3)	0.0228 (4)	0.0155 (4)	0.0013 (3)	0.0061 (3)	−0.0007 (3)
C22	0.0118 (3)	0.0162 (4)	0.0138 (3)	0.0012 (3)	0.0068 (3)	−0.0001 (3)

Geometric parameters (Å, º)

Ta1—Cl1	2.3452 (3)	C8—H8c	0.9800
Ta1—Cl2	2.3965 (3)	C9—H9a	0.9800
Ta1—N1	2.0433 (9)	C9—H9b	0.9800
Ta1—C1	2.2074 (11)	C9—H9c	0.9800
Ta1—C2	2.3732 (11)	C10—H10a	0.9800
Ta1—C3	2.4801 (11)	C10—H10b	0.9800
Ta1—C4	2.4536 (11)	C10—H10c	0.9800
Ta1—C5	2.3091 (11)	C11—C12	1.3965 (14)
Ta1—C6	2.3791 (11)	C11—C16	1.4137 (14)
N1—C11	1.4238 (13)	C12—H12	0.9500
N1—C22	1.4202 (13)	C12—C13	1.3941 (16)
C1—C2	1.4525 (16)	C13—H13	0.9500
C1—C5	1.4594 (16)	C13—C14	1.3994 (18)
C1—C6	1.4311 (17)	C14—H14	0.9500
C2—C3	1.4183 (18)	C14—C15	1.3876 (16)
C2—C7	1.5012 (18)	C15—H15	0.9500
C3—C4	1.4263 (16)	C15—C16	1.3960 (15)
C3—C8	1.4959 (17)	C16—C17	1.4486 (14)
C4—C5	1.4217 (16)	C17—C18	1.3957 (15)
C4—C9	1.4988 (17)	C17—C22	1.4079 (14)
C5—C10	1.5020 (16)	C18—H18	0.9500
C6—H6a	0.9900	C18—C19	1.3922 (16)
C6—H6b	0.9900	C19—H19	0.9500
C7—H7a	0.9800	C19—C20	1.4015 (17)
C7—H7b	0.9800	C20—H20	0.9500
C7—H7c	0.9800	C20—C21	1.3917 (16)
C8—H8a	0.9800	C21—H21	0.9500
C8—H8b	0.9800	C21—C22	1.3969 (15)
Cl2—Ta1—Cl1	88.239 (10)	C10—C5—C4	127.35 (11)
N1—Ta1—Cl1	114.15 (3)	C1—C6—Ta1	65.39 (6)
N1—Ta1—Cl2	93.54 (3)	H6a—C6—Ta1	117.19 (3)
C1—Ta1—Cl1	102.36 (3)	H6a—C6—C1	117.19 (7)
C1—Ta1—Cl2	148.56 (3)	H6b—C6—Ta1	117.19 (3)
C1—Ta1—N1	108.30 (4)	H6b—C6—C1	117.19 (6)
C2—Ta1—Cl1	85.73 (3)	H6b—C6—H6a	114.2
C2—Ta1—Cl2	116.91 (3)	H7a—C7—C2	109.5
C2—Ta1—N1	144.74 (4)	H7b—C7—C2	109.5
C2—Ta1—C1	36.75 (4)	H7b—C7—H7a	109.5
C3—Ta1—Cl1	105.24 (3)	H7c—C7—C2	109.5
C3—Ta1—Cl2	89.66 (3)	H7c—C7—H7a	109.5
C3—Ta1—N1	140.55 (4)	H7c—C7—H7b	109.5
C3—Ta1—C1	59.08 (4)	H8a—C8—C3	109.5
C3—Ta1—C2	33.89 (4)	H8b—C8—C3	109.5
C4—Ta1—Cl1	138.73 (3)	H8b—C8—H8a	109.5
C4—Ta1—Cl2	92.94 (3)	H8c—C8—C3	109.5
C4—Ta1—N1	106.95 (4)	H8c—C8—H8a	109.5
C4—Ta1—C1	59.64 (4)	H8c—C8—H8b	109.5
C4—Ta1—C2	57.21 (4)	H9a—C9—C4	109.5
C4—Ta1—C3	33.60 (4)	H9b—C9—C4	109.5
C5—Ta1—Cl1	139.87 (3)	H9b—C9—H9a	109.5
C5—Ta1—Cl2	124.16 (3)	H9c—C9—C4	109.5
C5—Ta1—N1	89.07 (4)	H9c—C9—H9a	109.5
C5—Ta1—C1	37.62 (4)	H9c—C9—H9b	109.5
C5—Ta1—C2	59.83 (4)	H10a—C10—C5	109.5
C5—Ta1—C3	57.63 (4)	H10b—C10—C5	109.5
C5—Ta1—C4	34.57 (4)	H10b—C10—H10a	109.5
C6—Ta1—Cl1	83.41 (3)	H10c—C10—C5	109.5
C6—Ta1—Cl2	171.58 (3)	H10c—C10—H10a	109.5
C6—Ta1—N1	88.93 (4)	H10c—C10—H10b	109.5
C6—Ta1—C1	36.12 (4)	C12—C11—N1	128.98 (9)
C6—Ta1—C2	63.62 (4)	C16—C11—N1	110.67 (8)
C6—Ta1—C3	93.54 (4)	C16—C11—C12	120.34 (9)
C6—Ta1—C4	94.03 (4)	H12—C12—C11	120.80 (6)
C6—Ta1—C5	63.87 (4)	C13—C12—C11	118.41 (10)
C11—N1—Ta1	124.03 (7)	C13—C12—H12	120.80 (7)
C22—N1—Ta1	128.17 (7)	H13—C13—C12	119.34 (7)
C22—N1—C11	104.92 (8)	C14—C13—C12	121.33 (10)
C2—C1—Ta1	77.85 (6)	C14—C13—H13	119.34 (6)
C5—C1—Ta1	74.97 (6)	H14—C14—C13	119.79 (6)
C5—C1—C2	106.66 (10)	C15—C14—C13	120.42 (10)
C6—C1—Ta1	78.49 (7)	C15—C14—H14	119.79 (7)
C6—C1—C2	120.62 (10)	H15—C15—C14	120.48 (7)
C6—C1—C5	118.22 (10)	C16—C15—C14	119.04 (10)
C1—C2—Ta1	65.41 (6)	C16—C15—H15	120.48 (6)
C3—C2—Ta1	77.19 (6)	C15—C16—C11	120.45 (9)
C3—C2—C1	108.05 (10)	C17—C16—C11	106.53 (8)
C7—C2—Ta1	124.43 (9)	C17—C16—C15	133.01 (10)
C7—C2—C1	125.74 (12)	C18—C17—C16	132.62 (9)
C7—C2—C3	126.17 (11)	C22—C17—C16	106.69 (8)
C2—C3—Ta1	68.92 (6)	C22—C17—C18	120.63 (9)
C4—C3—Ta1	72.18 (6)	H18—C18—C17	120.80 (6)
C4—C3—C2	108.73 (10)	C19—C18—C17	118.40 (10)
C8—C3—Ta1	126.62 (8)	C19—C18—H18	120.80 (6)
C8—C3—C2	126.51 (11)	H19—C19—C18	119.68 (6)
C8—C3—C4	124.72 (11)	C20—C19—C18	120.63 (10)
C3—C4—Ta1	74.22 (6)	C20—C19—H19	119.68 (6)
C5—C4—Ta1	67.15 (6)	H20—C20—C19	119.22 (6)
C5—C4—C3	108.62 (10)	C21—C20—C19	121.56 (10)
C9—C4—Ta1	129.19 (8)	C21—C20—H20	119.22 (6)
C9—C4—C3	123.93 (10)	H21—C21—C20	121.14 (6)
C9—C4—C5	127.19 (11)	C22—C21—C20	117.72 (10)
C1—C5—Ta1	67.41 (6)	C22—C21—H21	121.14 (6)
C4—C5—Ta1	78.28 (6)	C17—C22—N1	110.98 (8)
C4—C5—C1	107.78 (10)	C21—C22—N1	127.94 (9)
C10—C5—Ta1	121.82 (8)	C21—C22—C17	121.02 (9)
C10—C5—C1	124.80 (10)
Ta1—N1—C11—C12	−21.34 (10)	N1—C11—C16—C15	−177.53 (9)
Ta1—N1—C11—C16	157.54 (8)	N1—C11—C16—C17	3.18 (9)
Ta1—N1—C22—C17	−156.81 (9)	N1—C22—C17—C16	−2.47 (10)
Ta1—N1—C22—C21	25.74 (11)	N1—C22—C17—C18	−179.87 (9)
Ta1—C1—C2—C3	−66.06 (7)	N1—C22—C21—C20	179.22 (12)
Ta1—C1—C2—C7	115.89 (8)	C1—C2—C3—C4	−3.05 (10)
Ta1—C1—C5—C4	68.63 (7)	C1—C2—C3—C8	179.13 (9)
Ta1—C1—C5—C10	−113.97 (7)	C1—C5—C4—C3	1.63 (10)
Ta1—C2—C1—C5	70.04 (7)	C1—C5—C4—C9	175.84 (9)
Ta1—C2—C1—C6	−68.61 (7)	C2—C3—C4—C5	0.87 (10)
Ta1—C2—C3—C4	−61.51 (7)	C2—C3—C4—C9	−173.56 (9)
Ta1—C2—C3—C8	120.67 (8)	C3—C4—C5—C10	−175.68 (9)
Ta1—C3—C2—C1	58.46 (7)	C11—C12—C13—C14	0.24 (13)
Ta1—C3—C2—C7	−123.51 (8)	C11—C16—C15—C14	−0.73 (13)
Ta1—C3—C4—C5	−58.60 (7)	C11—C16—C17—C18	176.53 (8)
Ta1—C3—C4—C9	126.96 (7)	C11—C16—C17—C22	−0.43 (10)
Ta1—C4—C3—C2	59.48 (7)	C12—C13—C14—C15	0.48 (15)
Ta1—C4—C3—C8	−122.65 (8)	C13—C14—C15—C16	−0.23 (14)
Ta1—C4—C5—C1	−61.41 (7)	C14—C15—C16—C17	178.34 (10)
Ta1—C4—C5—C10	121.28 (7)	C15—C16—C17—C18	−2.63 (16)
Ta1—C5—C1—C2	−72.07 (7)	C15—C16—C17—C22	−179.59 (14)
Ta1—C5—C1—C6	67.75 (7)	C16—C17—C18—C19	−175.66 (13)
Ta1—C5—C4—C3	63.04 (7)	C16—C17—C22—C21	175.18 (9)
Ta1—C5—C4—C9	−122.75 (7)	C17—C18—C19—C20	0.42 (13)
Ta1—C6—C1—C2	68.27 (7)	C17—C22—C21—C20	2.00 (12)
Ta1—C6—C1—C5	−65.82 (7)	C18—C19—C20—C21	−0.59 (14)
N1—C11—C12—C13	177.59 (12)	C19—C20—C21—C22	−0.62 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8b···Cl2^i	0.98	2.91 (1)	3.7119 (14)	140 (1)
C12—H12···Cl2	0.95	2.64 (1)	3.3663 (12)	134 (1)
C13—H13···Cl2^ii	0.95	2.77 (1)	3.7217 (12)	179 (1)
C15—H15···Cl2^iii	0.95	2.86 (1)	3.7923 (12)	167 (1)
C18—H18···Cl1^iii	0.95	3.13 (1)	3.7645 (11)	126 (1)
C18—H18···Cl2^iii	0.95	2.85 (1)	3.7795 (12)	167 (1)
C19—H19···Cl1^iii	0.95	3.08 (1)	3.7479 (12)	128 (1)
C20—H20···Cl1^iv	0.95	2.95 (1)	3.5548 (12)	123 (1)

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