(S)-2-(2-Chloro­quinolin-3-yl)-2-[(S)-α-methylbenzyl­amino]acetonitrile

The title compound, C₁₉H₁₆ClN₃, crystallizes with two independent mol­ecules in the asymmetric unit. The structure is stabilized by C—H...N, N—H...N and C—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.093
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.70 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17B   -   C18B    ..       5.14 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C17B   -   H17'   ...       0.83 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N3B    -   H3'    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3'    ..  N2A     ..       2.68 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C11A   ..  CL1A    ..      97.40 Deg.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.00
           From the CIF: _reflns_number_total               7662
           Count of symmetry unique reflns         4359
           Completeness (_total/calc)            175.77%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3303
           Fraction of Friedel pairs measured     0.758
           Are heavy atom types Z>Si present        yes

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: 1- Benali-Cherif: Structure determination 2- Belfaitah, Ladraa, Debache, Rhouati: Organic synthesis 3- Bouraiou: purification and crystallization

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: KappaCCD Server Software (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).

(S)-2-(2-Chloroquinolin-3-yl)-2-[(S)-α-methylbenzylamino]acetonitrile

Crystal data

C19H16ClN3	F(000) = 672
Mr = 321.8	Dx = 1.275 Mg m^−3
Monoclinic, P21	Melting point: 383 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.8540 (1) Å	Cell parameters from 2548 reflections
b = 7.1090 (1) Å	θ = 1.7–28.0°
c = 23.9330 (3) Å	µ = 0.23 mm^−1
β = 91.590 (2)°	T = 293 K
V = 1675.91 (4) Å^3	Prism, yellow
Z = 4	0.2 × 0.15 × 0.1 mm

Data collection

Nonius KappaCCD area-detector diffractometer	4482 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.065
Graphite monochromator	θmax = 28.0°, θmin = 3.0°
φ/ω scans	h = −13→12
35588 measured reflections	k = −8→9
7662 independent reflections	l = −31→31

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0312P)^2 + 0.1354P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
7662 reflections	Δρmax = 0.15 e Å^−3
531 parameters	Δρmin = −0.15 e Å^−3
1 restraint	Absolute structure: Flack (1983), with how many Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (5)

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
C2A	0.3067 (3)	0.2435 (4)	0.16188 (10)	0.0590 (7)
C2B	0.5109 (3)	0.7287 (3)	0.26368 (12)	0.0544 (6)
C3A	0.4286 (2)	0.2318 (3)	0.19455 (10)	0.0459 (6)
C3B	0.4430 (3)	0.6621 (3)	0.31084 (10)	0.0493 (6)
C4A	0.4151 (3)	0.1936 (3)	0.24958 (11)	0.0504 (6)
C4B	0.3094 (3)	0.6266 (4)	0.30302 (12)	0.0524 (7)
C5A	0.2674 (4)	0.1198 (4)	0.32904 (15)	0.0698 (9)
C5B	0.1022 (3)	0.6227 (4)	0.24139 (15)	0.0672 (8)
C6A	0.1394 (5)	0.0830 (5)	0.3469 (2)	0.0891 (12)
C6B	0.0453 (4)	0.6530 (5)	0.18982 (17)	0.0835 (10)
C7A	0.0299 (4)	0.0834 (5)	0.3087 (2)	0.0947 (13)
C7B	0.1255 (5)	0.7178 (5)	0.14631 (17)	0.0896 (12)
C8A	0.0453 (3)	0.1235 (5)	0.2548 (2)	0.0830 (10)
C8B	0.2594 (4)	0.7488 (4)	0.15399 (13)	0.0744 (9)
C9A	0.2859 (3)	0.1599 (3)	0.27183 (11)	0.0538 (7)
C9B	0.2420 (3)	0.6556 (3)	0.25086 (11)	0.0524 (6)
C10A	0.1752 (3)	0.1653 (4)	0.23465 (14)	0.0621 (7)
C10B	0.3214 (3)	0.7175 (3)	0.20705 (11)	0.0565 (7)
C11A	0.5655 (3)	0.2460 (4)	0.16757 (11)	0.0539 (7)
C11B	0.5175 (3)	0.6261 (4)	0.36613 (10)	0.0538 (7)
C12A	0.7263 (3)	0.0391 (4)	0.11733 (12)	0.0607 (7)
C12B	0.6467 (3)	0.3789 (4)	0.41786 (11)	0.0537 (7)
C13A	0.7650 (3)	0.1883 (4)	0.07601 (10)	0.0538 (7)
C13B	0.7583 (3)	0.5135 (4)	0.43421 (11)	0.0536 (7)
C14A	0.6731 (3)	0.2481 (4)	0.03503 (11)	0.0666 (8)
C14B	0.8716 (4)	0.5325 (5)	0.40179 (16)	0.0797 (9)
C15A	0.7094 (4)	0.3817 (5)	−0.00396 (13)	0.0745 (9)
C15B	0.9739 (4)	0.6570 (7)	0.4169 (2)	0.0997 (12)
C16A	0.8387 (4)	0.4517 (5)	−0.00318 (16)	0.0786 (9)
C16B	0.9656 (5)	0.7624 (6)	0.4630 (2)	0.0972 (12)
C17A	0.9306 (4)	0.3933 (5)	0.03698 (16)	0.0782 (10)
C17B	0.8550 (5)	0.7500 (5)	0.49490 (18)	0.0906 (12)
C18A	0.8938 (3)	0.2636 (5)	0.07634 (13)	0.0690 (8)
C18B	0.7507 (4)	0.6249 (4)	0.48074 (13)	0.0673 (8)
C19A	0.7297 (3)	−0.1572 (5)	0.09188 (13)	0.0914 (10)
H19A	0.7046	−0.2481	0.1194	0.137*
H19B	0.8197	−0.1839	0.0797	0.137*
H19C	0.6670	−0.1633	0.0605	0.137*
C19B	0.6943 (5)	0.1787 (5)	0.41029 (19)	0.0810 (10)
C20A	0.6707 (2)	0.2936 (4)	0.21198 (12)	0.0582 (7)
C20B	0.4240 (3)	0.6516 (5)	0.41233 (12)	0.0756 (9)
Cl1A	0.31679 (8)	0.31128 (13)	0.09178 (3)	0.0849 (3)
Cl1B	0.68313 (7)	0.78912 (11)	0.27095 (3)	0.0779 (2)
N1A	0.1859 (2)	0.2102 (3)	0.17912 (11)	0.0680 (6)
N1B	0.4577 (2)	0.7533 (3)	0.21403 (9)	0.0588 (6)
N2A	0.7472 (3)	0.3284 (4)	0.24552 (11)	0.0858 (8)
N2B	0.3513 (3)	0.6755 (6)	0.44753 (12)	0.1213 (12)
N3A	0.5900 (2)	0.0694 (3)	0.13827 (9)	0.0546 (6)
N3B	0.5690 (2)	0.4327 (3)	0.36654 (9)	0.0528 (6)
H3	0.569 (3)	−0.022 (4)	0.1626 (11)	0.066 (9)*
H3'	0.627 (2)	0.433 (3)	0.3393 (10)	0.047 (7)*
H4	0.493 (2)	0.186 (3)	0.2740 (9)	0.037 (6)*
H4'	0.256 (2)	0.582 (3)	0.3310 (10)	0.045 (7)*
H5'	0.052 (3)	0.576 (4)	0.2701 (14)	0.084 (11)*
H5	0.335 (3)	0.128 (4)	0.3530 (11)	0.068 (10)*
H6'	−0.044 (3)	0.641 (4)	0.1814 (12)	0.081 (10)*
H6	0.125 (3)	0.068 (5)	0.3858 (15)	0.101 (12)*
H7'	0.078 (3)	0.736 (4)	0.1148 (14)	0.094 (11)*
H7	−0.057 (3)	0.070 (4)	0.3212 (11)	0.071 (9)*
H8'	0.320 (2)	0.798 (4)	0.1262 (10)	0.070 (8)*
H8	−0.024 (3)	0.136 (5)	0.2238 (14)	0.101 (12)*
H9A'	0.750 (4)	0.166 (5)	0.3768 (15)	0.109 (13)*
H9B'	0.750 (3)	0.137 (4)	0.4406 (13)	0.082 (10)*
H9C'	0.616 (4)	0.102 (5)	0.4045 (14)	0.102 (13)*
H11'	0.591 (2)	0.721 (3)	0.3710 (8)	0.045 (6)*
H11	0.570 (2)	0.354 (4)	0.1411 (10)	0.063 (7)*
H12'	0.582 (2)	0.381 (3)	0.4472 (10)	0.056 (7)*
H12	0.794 (2)	0.043 (3)	0.1472 (10)	0.055 (7)*
H14'	0.872 (3)	0.450 (5)	0.3709 (14)	0.093 (11)*
H14	0.585 (2)	0.198 (3)	0.0328 (9)	0.051 (7)*
H15	0.648 (3)	0.416 (4)	−0.0305 (11)	0.068 (9)*
H15'	1.046 (4)	0.652 (5)	0.3934 (14)	0.103 (13)*
H16	0.868 (3)	0.548 (5)	−0.0314 (14)	0.104 (11)*
H16'	1.042 (4)	0.839 (6)	0.4745 (13)	0.116 (13)*
H17	1.018 (3)	0.433 (5)	0.0371 (13)	0.094 (11)*
H17'	0.843 (3)	0.809 (5)	0.5244 (13)	0.086 (11)*
H18	0.957 (3)	0.224 (4)	0.1042 (11)	0.069 (9)*
H18'	0.674 (3)	0.615 (4)	0.5036 (10)	0.062 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2A	0.0662 (18)	0.0533 (17)	0.0572 (16)	0.0169 (14)	−0.0030 (14)	−0.0195 (13)
C2B	0.0653 (16)	0.0390 (14)	0.0592 (17)	0.0037 (12)	0.0043 (14)	−0.0008 (12)
C3A	0.0515 (15)	0.0402 (14)	0.0459 (15)	0.0064 (11)	−0.0003 (12)	−0.0106 (11)
C3B	0.0635 (17)	0.0371 (14)	0.0474 (15)	0.0017 (12)	0.0019 (13)	−0.0026 (12)
C4A	0.0559 (17)	0.0400 (14)	0.0549 (17)	0.0027 (12)	−0.0046 (14)	−0.0064 (12)
C4B	0.0658 (19)	0.0434 (15)	0.0483 (17)	0.0032 (13)	0.0076 (15)	−0.0003 (13)
C5A	0.077 (2)	0.059 (2)	0.074 (2)	−0.0069 (17)	0.011 (2)	−0.0100 (17)
C5B	0.073 (2)	0.0611 (19)	0.067 (2)	0.0031 (16)	−0.0089 (19)	−0.0044 (17)
C6A	0.106 (3)	0.076 (2)	0.088 (3)	−0.014 (2)	0.045 (3)	−0.019 (2)
C6B	0.084 (3)	0.070 (2)	0.094 (3)	0.009 (2)	−0.031 (2)	−0.005 (2)
C7A	0.064 (3)	0.095 (3)	0.127 (4)	−0.006 (2)	0.040 (3)	−0.024 (2)
C7B	0.120 (3)	0.073 (2)	0.073 (3)	0.012 (2)	−0.040 (3)	−0.0050 (19)
C8A	0.057 (2)	0.087 (2)	0.106 (3)	0.0018 (18)	0.013 (2)	−0.026 (2)
C8B	0.109 (3)	0.0544 (19)	0.058 (2)	0.0035 (18)	−0.012 (2)	0.0027 (15)
C9A	0.0603 (17)	0.0398 (14)	0.0618 (18)	0.0007 (13)	0.0130 (15)	−0.0130 (13)
C9B	0.0635 (18)	0.0390 (14)	0.0542 (16)	0.0069 (12)	−0.0041 (14)	−0.0034 (12)
C10A	0.0581 (18)	0.0464 (16)	0.082 (2)	0.0029 (14)	0.0125 (17)	−0.0183 (15)
C10B	0.081 (2)	0.0387 (14)	0.0495 (16)	0.0077 (14)	−0.0065 (15)	−0.0033 (12)
C11A	0.0624 (16)	0.0475 (17)	0.0522 (16)	0.0036 (13)	0.0056 (13)	0.0004 (14)
C11B	0.0647 (17)	0.0503 (17)	0.0464 (15)	−0.0012 (14)	0.0002 (13)	−0.0068 (13)
C12A	0.0606 (18)	0.071 (2)	0.0505 (17)	0.0157 (15)	0.0028 (15)	−0.0037 (15)
C12B	0.0677 (18)	0.0544 (17)	0.0389 (15)	0.0027 (14)	0.0003 (14)	0.0041 (12)
C13A	0.0587 (17)	0.0646 (17)	0.0384 (14)	0.0066 (14)	0.0062 (13)	−0.0055 (13)
C13B	0.0608 (18)	0.0551 (16)	0.0444 (16)	0.0040 (14)	−0.0067 (14)	0.0030 (13)
C14A	0.0612 (18)	0.090 (2)	0.0481 (16)	−0.0096 (17)	0.0030 (14)	0.0026 (16)
C14B	0.074 (2)	0.091 (2)	0.074 (2)	−0.009 (2)	0.0033 (19)	−0.008 (2)
C15A	0.078 (2)	0.096 (3)	0.0504 (18)	0.006 (2)	0.0047 (17)	0.0088 (17)
C15B	0.072 (2)	0.120 (3)	0.107 (3)	−0.014 (2)	0.007 (2)	0.009 (3)
C16A	0.086 (3)	0.080 (2)	0.071 (2)	0.000 (2)	0.024 (2)	0.0043 (18)
C16B	0.095 (3)	0.091 (3)	0.104 (3)	−0.027 (3)	−0.033 (3)	0.015 (3)
C17A	0.063 (2)	0.085 (2)	0.087 (3)	−0.0067 (19)	0.020 (2)	−0.011 (2)
C17B	0.126 (4)	0.073 (2)	0.072 (2)	−0.003 (2)	−0.025 (3)	−0.007 (2)
C18A	0.0626 (19)	0.087 (2)	0.0574 (18)	0.0140 (19)	0.0039 (16)	−0.0066 (18)
C18B	0.078 (2)	0.067 (2)	0.0566 (18)	0.0009 (18)	−0.0034 (17)	−0.0027 (16)
C19A	0.113 (2)	0.073 (2)	0.089 (2)	0.031 (2)	0.0265 (19)	−0.0062 (19)
C19B	0.107 (3)	0.056 (2)	0.080 (3)	0.009 (2)	−0.015 (3)	0.0085 (18)
C20A	0.0461 (14)	0.0574 (17)	0.0712 (18)	0.0005 (15)	0.0066 (14)	−0.0151 (16)
C20B	0.080 (2)	0.099 (2)	0.0472 (17)	0.0230 (19)	−0.0056 (16)	−0.0124 (17)
Cl1A	0.0979 (5)	0.1011 (6)	0.0549 (4)	0.0278 (5)	−0.0124 (4)	−0.0100 (4)
Cl1B	0.0694 (4)	0.0758 (5)	0.0887 (5)	−0.0087 (4)	0.0067 (4)	0.0097 (5)
N1A	0.0584 (15)	0.0643 (15)	0.0809 (18)	0.0131 (12)	−0.0031 (13)	−0.0190 (13)
N1B	0.0823 (16)	0.0425 (13)	0.0519 (13)	0.0012 (11)	0.0043 (12)	0.0045 (10)
N2A	0.0701 (16)	0.098 (2)	0.0892 (18)	0.0075 (16)	−0.0037 (15)	−0.0285 (17)
N2B	0.111 (2)	0.191 (3)	0.0620 (18)	0.043 (2)	0.0118 (17)	−0.026 (2)
N3A	0.0687 (16)	0.0474 (13)	0.0482 (14)	0.0074 (11)	0.0114 (11)	−0.0019 (11)
N3B	0.0638 (14)	0.0501 (14)	0.0445 (13)	0.0064 (11)	0.0025 (12)	0.0009 (10)

Geometric parameters (Å, º)

N2A—C20A	1.113 (3)	C11A—C20A	1.503 (4)
C17A—C18A	1.374 (4)	C11A—H11	1.00 (3)
N2B—C20B	1.134 (3)	C11B—N3B	1.465 (3)
C17B—C18B	1.394 (5)	C11B—C20B	1.470 (4)
C2A—N1A	1.292 (3)	C11B—H11'	0.99 (2)
C2A—C3A	1.417 (3)	C12A—N3A	1.463 (3)
C2A—Cl1A	1.751 (3)	C12A—C13A	1.506 (4)
C2B—N1B	1.297 (3)	C12A—C19A	1.524 (4)
C2B—C3B	1.410 (3)	C12A—H12	0.96 (2)
C2B—Cl1B	1.755 (3)	C12B—N3B	1.480 (3)
C3A—C4A	1.355 (3)	C12B—C13B	1.501 (4)
C3A—C11A	1.515 (3)	C12B—C19B	1.511 (4)
C3B—C4B	1.349 (3)	C12B—H12'	0.96 (2)
C3B—C11B	1.517 (3)	C13A—C18A	1.378 (4)
C4A—C9A	1.414 (3)	C13A—C14A	1.383 (4)
C4A—H4	0.95 (2)	C13B—C18B	1.370 (4)
C4B—C9B	1.413 (3)	C13B—C14B	1.384 (4)
C4B—H4'	0.92 (2)	C14A—C15A	1.386 (4)
C5A—C6A	1.368 (5)	C14A—H14	0.94 (2)
C5A—C9A	1.415 (4)	C14B—C15B	1.382 (5)
C5A—H5	0.87 (3)	C14B—H14'	0.94 (3)
C5B—C6B	1.358 (4)	C15A—C16A	1.367 (4)
C5B—C9B	1.409 (4)	C15A—H15	0.90 (3)
C5B—H5'	0.92 (3)	C15B—C16B	1.337 (5)
C6A—C7A	1.395 (5)	C15B—H15'	0.92 (3)
C6A—H6	0.95 (3)	C16A—C17A	1.367 (5)
C6B—C7B	1.402 (5)	C16A—H16	1.01 (4)
C6B—H6'	0.90 (3)	C16B—C17B	1.351 (5)
C7A—C8A	1.334 (5)	C16B—H16'	0.97 (4)
C7A—H7	0.92 (3)	C17A—H17	0.91 (3)
C7B—C8B	1.345 (5)	C17B—H17'	0.83 (3)
C7B—H7'	0.89 (3)	C18A—H18	0.94 (3)
C8A—C10A	1.412 (4)	C18B—H18'	0.95 (3)
C8A—H8	1.00 (3)	C19A—H19A	0.9600
C8B—C10B	1.411 (4)	C19A—H19B	0.9600
C8B—H8'	0.97 (3)	C19A—H19C	0.9600
C9A—C10A	1.389 (4)	C19B—H9A'	0.99 (4)
C9B—C10B	1.397 (4)	C19B—H9B'	0.95 (3)
C10A—N1A	1.374 (3)	C19B—H9C'	0.95 (4)
C10B—N1B	1.373 (3)	N3A—H3	0.90 (3)
C11A—N3A	1.462 (3)	N3B—H3'	0.88 (2)
N3A—C11A—C20A	114.4 (2)	N3A—C12A—C13A	111.9 (2)
C11A—N3A—C12A	117.1 (2)	N3A—C12A—C19A	107.6 (3)
N3B—C11B—C20B	109.6 (2)	C13A—C12A—C19A	112.0 (2)
C11B—N3B—C12B	114.8 (2)	N3A—C12A—H12	111.4 (14)
N1A—C2A—C3A	125.9 (2)	C13A—C12A—H12	106.5 (14)
N1A—C2A—Cl1A	115.7 (2)	C19A—C12A—H12	107.5 (15)
C3A—C2A—Cl1A	118.3 (2)	N3B—C12B—C13B	114.2 (2)
N1B—C2B—C3B	126.2 (2)	N3B—C12B—C19B	107.4 (3)
N1B—C2B—Cl1B	115.02 (19)	C13B—C12B—C19B	113.8 (3)
C3B—C2B—Cl1B	118.8 (2)	N3B—C12B—H12'	105.4 (14)
C4A—C3A—C2A	116.3 (2)	C13B—C12B—H12'	107.2 (14)
C4A—C3A—C11A	122.7 (2)	C19B—C12B—H12'	108.3 (14)
C2A—C3A—C11A	120.8 (2)	C18A—C13A—C14A	118.0 (3)
C4B—C3B—C2B	115.8 (2)	C18A—C13A—C12A	121.3 (3)
C4B—C3B—C11B	122.4 (2)	C14A—C13A—C12A	120.6 (3)
C2B—C3B—C11B	121.7 (2)	C18B—C13B—C14B	117.5 (3)
C3A—C4A—C9A	120.9 (2)	C18B—C13B—C12B	121.6 (3)
C3A—C4A—H4	120.6 (12)	C14B—C13B—C12B	120.8 (3)
C9A—C4A—H4	118.5 (12)	C13A—C14A—C15A	120.8 (3)
C3B—C4B—C9B	121.9 (3)	C13A—C14A—H14	120.8 (15)
C3B—C4B—H4'	122.7 (15)	C15A—C14A—H14	118.4 (15)
C9B—C4B—H4'	115.3 (15)	C15B—C14B—C13B	120.7 (4)
C6A—C5A—C9A	119.0 (4)	C15B—C14B—H14'	126 (2)
C6A—C5A—H5	120.2 (19)	C13B—C14B—H14'	114 (2)
C9A—C5A—H5	120.6 (19)	C16A—C15A—C14A	119.9 (3)
C6B—C5B—C9B	119.8 (4)	C16A—C15A—H15	121.4 (18)
C6B—C5B—H5'	121 (2)	C14A—C15A—H15	118.6 (18)
C9B—C5B—H5'	119 (2)	C16B—C15B—C14B	120.9 (4)
C5A—C6A—C7A	119.9 (4)	C16B—C15B—H15'	126 (2)
C5A—C6A—H6	119 (2)	C14B—C15B—H15'	113 (2)
C7A—C6A—H6	121 (2)	C17A—C16A—C15A	119.9 (4)
C5B—C6B—C7B	120.0 (4)	C17A—C16A—H16	118.7 (19)
C5B—C6B—H6'	124.3 (19)	C15A—C16A—H16	121.4 (19)
C7B—C6B—H6'	115.6 (19)	C15B—C16B—C17B	119.9 (4)
C8A—C7A—C6A	121.8 (4)	C15B—C16B—H16'	119 (2)
C8A—C7A—H7	118.0 (17)	C17B—C16B—H16'	121 (2)
C6A—C7A—H7	119.8 (17)	C16A—C17A—C18A	120.2 (4)
C8B—C7B—C6B	121.5 (4)	C16A—C17A—H17	121 (2)
C8B—C7B—H7'	126 (2)	C18A—C17A—H17	118 (2)
C6B—C7B—H7'	112 (2)	C16B—C17B—C18B	120.3 (4)
C7A—C8A—C10A	120.3 (4)	C16B—C17B—H17'	126 (2)
C7A—C8A—H8	130.1 (19)	C18B—C17B—H17'	114 (2)
C10A—C8A—H8	109.6 (19)	C17A—C18A—C13A	121.2 (3)
C7B—C8B—C10B	119.7 (3)	C17A—C18A—H18	120.3 (16)
C7B—C8B—H8'	125.7 (15)	C13A—C18A—H18	118.6 (16)
C10B—C8B—H8'	114.5 (15)	C13B—C18B—C17B	120.7 (4)
C10A—C9A—C4A	117.0 (2)	C13B—C18B—H18'	119.2 (16)
C10A—C9A—C5A	120.4 (3)	C17B—C18B—H18'	120.2 (16)
C4A—C9A—C5A	122.7 (3)	C12A—C19A—H19A	109.5
C10B—C9B—C5B	119.8 (3)	C12A—C19A—H19B	109.5
C10B—C9B—C4B	116.7 (2)	H19A—C19A—H19B	109.5
C5B—C9B—C4B	123.5 (3)	C12A—C19A—H19C	109.5
N1A—C10A—C9A	123.1 (2)	H19A—C19A—H19C	109.5
N1A—C10A—C8A	118.3 (3)	H19B—C19A—H19C	109.5
C9A—C10A—C8A	118.6 (3)	C12B—C19B—H9A'	112 (2)
N1B—C10B—C9B	122.2 (2)	C12B—C19B—H9B'	112.4 (19)
N1B—C10B—C8B	118.6 (3)	H9A'—C19B—H9B'	105 (3)
C9B—C10B—C8B	119.2 (3)	C12B—C19B—H9C'	108 (2)
N3A—C11A—C3A	108.0 (2)	H9A'—C19B—H9C'	107 (3)
C20A—C11A—C3A	108.59 (19)	H9B'—C19B—H9C'	113 (3)
N3A—C11A—H11	110.4 (13)	N2A—C20A—C11A	178.9 (3)
C20A—C11A—H11	103.6 (13)	N2B—C20B—C11B	178.4 (4)
C3A—C11A—H11	112.0 (13)	C2A—N1A—C10A	116.6 (2)
N3B—C11B—C3B	108.9 (2)	C2B—N1B—C10B	117.1 (2)
C20B—C11B—C3B	109.7 (2)	C11A—N3A—H3	105.2 (17)
N3B—C11B—H11'	112.9 (12)	C12A—N3A—H3	110.4 (16)
C20B—C11B—H11'	107.2 (12)	C11B—N3B—H3'	103.0 (16)
C3B—C11B—H11'	108.6 (12)	C12B—N3B—H3'	106.3 (15)
C3A—C11A—N3A—C12A	−169.6 (2)	C7B—C8B—C10B—C9B	−0.3 (4)
C4A—C3A—C11A—N3A	100.8 (3)	C2A—C3A—C11A—N3A	−74.1 (3)
C19A—C12A—C13A—C18A	−99.7 (3)	C4A—C3A—C11A—C20A	−23.8 (3)
C3B—C11B—N3B—C12B	178.9 (2)	C2A—C3A—C11A—C20A	161.4 (2)
C4B—C3B—C11B—N3B	89.2 (3)	C2B—C3B—C11B—N3B	−88.5 (3)
C19B—C12B—C13B—C18B	−125.7 (3)	C4B—C3B—C11B—C20B	−30.7 (3)
N1A—C2A—C3A—C4A	−4.3 (4)	C2B—C3B—C11B—C20B	151.6 (3)
Cl1A—C2A—C3A—C4A	174.90 (18)	N3A—C12A—C13A—C18A	139.4 (3)
N1A—C2A—C3A—C11A	170.8 (2)	N3A—C12A—C13A—C14A	−43.3 (4)
Cl1A—C2A—C3A—C11A	−9.9 (3)	C19A—C12A—C13A—C14A	77.6 (3)
N1B—C2B—C3B—C4B	−2.1 (3)	N3B—C12B—C13B—C18B	110.5 (3)
Cl1B—C2B—C3B—C4B	176.99 (19)	N3B—C12B—C13B—C14B	−68.0 (3)
N1B—C2B—C3B—C11B	175.8 (2)	C19B—C12B—C13B—C14B	55.9 (4)
Cl1B—C2B—C3B—C11B	−5.2 (3)	C18A—C13A—C14A—C15A	−0.9 (4)
C2A—C3A—C4A—C9A	2.5 (3)	C12A—C13A—C14A—C15A	−178.3 (3)
C11A—C3A—C4A—C9A	−172.6 (2)	C18B—C13B—C14B—C15B	1.3 (5)
C2B—C3B—C4B—C9B	−0.3 (3)	C12B—C13B—C14B—C15B	179.8 (3)
C11B—C3B—C4B—C9B	−178.1 (2)	C13A—C14A—C15A—C16A	2.0 (4)
C9A—C5A—C6A—C7A	0.7 (5)	C13B—C14B—C15B—C16B	−0.3 (6)
C9B—C5B—C6B—C7B	−0.4 (5)	C14A—C15A—C16A—C17A	−1.8 (5)
C5A—C6A—C7A—C8A	−1.6 (5)	C14B—C15B—C16B—C17B	−1.0 (6)
C5B—C6B—C7B—C8B	1.0 (5)	C15A—C16A—C17A—C18A	0.5 (5)
C6A—C7A—C8A—C10A	0.6 (5)	C15B—C16B—C17B—C18B	1.4 (6)
C6B—C7B—C8B—C10B	−0.6 (5)	C16A—C17A—C18A—C13A	0.7 (4)
C3A—C4A—C9A—C10A	0.9 (4)	C14A—C13A—C18A—C17A	−0.4 (4)
C3A—C4A—C9A—C5A	−179.9 (2)	C12A—C13A—C18A—C17A	176.9 (3)
C6A—C5A—C9A—C10A	1.2 (4)	C14B—C13B—C18B—C17B	−1.0 (4)
C6A—C5A—C9A—C4A	−177.9 (3)	C12B—C13B—C18B—C17B	−179.5 (3)
C6B—C5B—C9B—C10B	−0.5 (4)	C16B—C17B—C18B—C13B	−0.3 (5)
C6B—C5B—C9B—C4B	−179.6 (3)	C3A—C2A—N1A—C10A	2.2 (4)
C3B—C4B—C9B—C10B	1.9 (3)	Cl1A—C2A—N1A—C10A	−177.06 (18)
C3B—C4B—C9B—C5B	−179.0 (3)	C9A—C10A—N1A—C2A	1.7 (4)
C4A—C9A—C10A—N1A	−3.2 (4)	C8A—C10A—N1A—C2A	−178.5 (3)
C5A—C9A—C10A—N1A	177.5 (2)	C3B—C2B—N1B—C10B	2.5 (3)
C4A—C9A—C10A—C8A	177.0 (3)	Cl1B—C2B—N1B—C10B	−176.59 (17)
C5A—C9A—C10A—C8A	−2.2 (4)	C9B—C10B—N1B—C2B	−0.6 (3)
C7A—C8A—C10A—N1A	−178.5 (3)	C8B—C10B—N1B—C2B	177.9 (2)
C7A—C8A—C10A—C9A	1.3 (5)	C20A—C11A—N3A—C12A	−48.7 (3)
C5B—C9B—C10B—N1B	179.4 (2)	C13A—C12A—N3A—C11A	−60.1 (3)
C4B—C9B—C10B—N1B	−1.4 (3)	C19A—C12A—N3A—C11A	176.6 (2)
C5B—C9B—C10B—C8B	0.9 (4)	C20B—C11B—N3B—C12B	−61.2 (3)
C4B—C9B—C10B—C8B	−180.0 (2)	C13B—C12B—N3B—C11B	−51.3 (3)
C7B—C8B—C10B—N1B	−178.9 (3)	C19B—C12B—N3B—C11B	−178.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3···N1B^i	0.90 (3)	2.31 (3)	3.189 (3)	165.6 (2)
N3B—H3′···N2A	0.87 (2)	2.68 (2)	3.508 (3)	159.6 (19)
C11B—H11′···Cl1B	0.98 (2)	2.641 (19)	3.067 (3)	106.3 (13)
C11A—H11···Cl1A	1.00 (3)	2.76 (2)	3.044 (3)	97.4 (14)

Symmetry code: (i) x, y−1, z.