Crystal structure of {(S)-1-phenyl-N,N-bis­[(pyridin-2-yl)meth­yl]ethanamine-κ³N,N′,N′′}bis­(thio­cyanato-κN)zinc from synchrotron data

The Zn^II ion in the title compound shows a distorted square-pyramidal coordination geometry with three N atoms of the chiral S-ppme ligand and two N atoms of the thio­cyanate anions. In the crystal, mol­ecules are connected by hydrogen bonds and π–π inter­actions, forming a two-dimensional supra­molecular network parallel to the bc plane.

Key indicators

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.039
• wR factor = 0.093
• Data-to-parameter ratio = 22.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.977 Note
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00622 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         47 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT791_ALERT_4_G The Model has Chirality at C13     (Chiral SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         62 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note

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

   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
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: PAL BL2D-SMDC (Shin et al., 2016); cell refinement: HKL3000sm (Otwinowski & Minor, 1997); data reduction: HKL3000sm (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Putz & Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).

{(S)-1-Phenyl-N,N-bis[(pyridin-2-yl)methyl]ethanamine-κ³N,N',N''}bis(thiocyanato-κN)zinc(II)

Crystal data

[Zn(NCS)2(C20H21N3)]	F(000) = 1000
Mr = 484.93	Dx = 1.446 Mg m^−3
Monoclinic, C2	Synchrotron radiation, λ = 0.630 Å
a = 19.270 (4) Å	Cell parameters from 32924 reflections
b = 7.7950 (16) Å	θ = 0.4–33.6°
c = 14.834 (3) Å	µ = 0.94 mm^−1
β = 91.71 (3)°	T = 100 K
V = 2227.2 (8) Å^3	Needle, colorless
Z = 4	0.10 × 0.04 × 0.02 mm

Data collection

ADSC Q210 CCD area detector diffractometer	5123 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnet	Rint = 0.048
ω scan	θmax = 26.0°, θmin = 2.4°
Absorption correction: empirical (using intensity measurements) (HKL3000sm SCALEPACK; Otwinowski & Minor, 1997)	h = −26→26
Tmin = 0.912, Tmax = 0.981	k = −10→10
11189 measured reflections	l = −20→20
6035 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0509P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.093	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.35 e Å^−3
6035 reflections	Δρmin = −1.03 e Å^−3
272 parameters	Absolute structure: Flack x determined using 2026 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.010 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Zn1	0.46128 (2)	0.33954 (6)	0.76988 (3)	0.01920 (11)
N1	0.52691 (16)	0.5093 (4)	0.8331 (2)	0.0213 (7)
N2	0.40589 (15)	0.6204 (4)	0.7503 (2)	0.0165 (7)
N3	0.43224 (14)	0.3562 (5)	0.6353 (2)	0.0199 (6)
C1	0.5905 (2)	0.4552 (6)	0.8617 (3)	0.0287 (9)
H1	0.6043	0.3414	0.8480	0.034*
C2	0.6357 (2)	0.5585 (7)	0.9097 (3)	0.0331 (10)
H2	0.6797	0.5161	0.9298	0.040*
C3	0.6165 (2)	0.7254 (7)	0.9286 (3)	0.0306 (10)
H3	0.6474	0.7999	0.9606	0.037*
C4	0.5509 (2)	0.7824 (6)	0.8998 (3)	0.0254 (9)
H4	0.5362	0.8960	0.9126	0.030*
C5	0.50773 (19)	0.6714 (6)	0.8525 (3)	0.0198 (8)
C6	0.4348 (2)	0.7272 (5)	0.8232 (3)	0.0232 (8)
H6A	0.4042	0.7208	0.8755	0.028*
H6B	0.4360	0.8480	0.8028	0.028*
C7	0.44001 (19)	0.6585 (6)	0.6647 (3)	0.0194 (7)
H7A	0.4905	0.6735	0.6761	0.023*
H7B	0.4212	0.7666	0.6388	0.023*
C8	0.42740 (19)	0.5140 (5)	0.5994 (3)	0.0188 (8)
C9	0.4133 (2)	0.5404 (7)	0.5076 (3)	0.0277 (10)
H9	0.4107	0.6529	0.4831	0.033*
C10	0.4032 (2)	0.3974 (7)	0.4533 (3)	0.0360 (13)
H10	0.3938	0.4108	0.3905	0.043*
C11	0.4069 (2)	0.2344 (7)	0.4910 (3)	0.0360 (13)
H11	0.3991	0.1356	0.4546	0.043*
C12	0.4220 (2)	0.2182 (6)	0.5822 (3)	0.0282 (10)
H12	0.4252	0.1069	0.6081	0.034*
C13	0.32788 (18)	0.6288 (5)	0.7383 (3)	0.0188 (8)
H13	0.3149	0.5409	0.6917	0.023*
C14	0.30213 (18)	0.8003 (5)	0.7011 (3)	0.0184 (8)
C15	0.2898 (2)	0.9419 (5)	0.7561 (3)	0.0238 (8)
H15	0.2977	0.9328	0.8194	0.029*
C16	0.2663 (2)	1.0954 (6)	0.7194 (3)	0.0286 (10)
H16	0.2576	1.1899	0.7579	0.034*
C17	0.2554 (2)	1.1123 (5)	0.6272 (3)	0.0258 (9)
H17	0.2394	1.2179	0.6024	0.031*
C18	0.2679 (2)	0.9745 (6)	0.5717 (3)	0.0272 (9)
H18	0.2616	0.9858	0.5083	0.033*
C19	0.28976 (18)	0.8195 (6)	0.6087 (3)	0.0221 (8)
H19	0.2964	0.7241	0.5701	0.027*
C20	0.2913 (2)	0.5759 (6)	0.8239 (3)	0.0253 (9)
H20A	0.2982	0.6648	0.8700	0.038*
H20B	0.3107	0.4672	0.8462	0.038*
H20C	0.2415	0.5619	0.8104	0.038*
N4	0.53102 (18)	0.1463 (5)	0.7434 (3)	0.0299 (8)
C21	0.5672 (2)	0.0390 (5)	0.7176 (3)	0.0210 (8)
S1	0.61788 (5)	−0.11203 (13)	0.68120 (7)	0.0269 (2)
N5	0.40467 (18)	0.2318 (5)	0.8601 (3)	0.0267 (8)
S2	0.31745 (6)	0.13587 (16)	0.99713 (8)	0.0303 (3)
C22	0.3691 (2)	0.1913 (5)	0.9177 (3)	0.0220 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.01633 (18)	0.0166 (2)	0.0249 (2)	0.0000 (2)	0.00448 (14)	0.0002 (2)
N1	0.0170 (15)	0.0190 (17)	0.0276 (17)	0.0002 (14)	−0.0009 (13)	0.0016 (13)
N2	0.0123 (13)	0.0154 (16)	0.0221 (16)	−0.0017 (12)	0.0027 (12)	−0.0035 (12)
N3	0.0122 (12)	0.0209 (17)	0.0270 (15)	0.0012 (16)	0.0053 (11)	−0.0060 (15)
C1	0.0173 (18)	0.029 (2)	0.039 (2)	0.0041 (18)	−0.0019 (17)	0.0042 (19)
C2	0.0173 (19)	0.039 (3)	0.043 (3)	−0.003 (2)	−0.0062 (18)	0.004 (2)
C3	0.027 (2)	0.040 (3)	0.025 (2)	−0.012 (2)	−0.0027 (17)	0.0042 (19)
C4	0.0291 (19)	0.026 (2)	0.0212 (19)	−0.0066 (18)	0.0015 (15)	0.0004 (15)
C5	0.0170 (17)	0.021 (2)	0.0212 (18)	−0.0035 (17)	0.0021 (14)	0.0012 (15)
C6	0.0206 (18)	0.022 (2)	0.027 (2)	0.0001 (17)	0.0027 (15)	−0.0061 (16)
C7	0.0145 (16)	0.0213 (19)	0.0226 (18)	0.0009 (16)	0.0041 (14)	0.0029 (16)
C8	0.0103 (16)	0.025 (2)	0.0217 (19)	0.0004 (16)	0.0050 (14)	−0.0006 (16)
C9	0.0163 (18)	0.044 (3)	0.023 (2)	0.005 (2)	0.0043 (15)	0.0002 (19)
C10	0.0156 (17)	0.069 (4)	0.024 (2)	0.001 (2)	0.0044 (15)	−0.011 (2)
C11	0.020 (2)	0.053 (4)	0.036 (3)	−0.004 (2)	0.0055 (19)	−0.026 (2)
C12	0.018 (2)	0.027 (2)	0.040 (3)	0.0004 (19)	0.0066 (17)	−0.009 (2)
C13	0.0138 (16)	0.0162 (19)	0.027 (2)	0.0018 (15)	0.0036 (14)	−0.0021 (15)
C14	0.0110 (14)	0.016 (2)	0.0280 (19)	0.0010 (14)	0.0021 (13)	−0.0027 (14)
C15	0.0221 (19)	0.021 (2)	0.029 (2)	0.0023 (18)	0.0022 (15)	−0.0063 (17)
C16	0.026 (2)	0.023 (2)	0.037 (2)	0.0081 (19)	−0.0006 (18)	−0.0068 (18)
C17	0.0190 (19)	0.021 (2)	0.037 (2)	0.0048 (17)	−0.0008 (17)	0.0020 (17)
C18	0.0201 (19)	0.031 (2)	0.030 (2)	0.0104 (19)	−0.0016 (16)	0.0013 (18)
C19	0.0171 (15)	0.021 (2)	0.0277 (18)	0.0029 (18)	−0.0016 (13)	−0.0064 (18)
C20	0.0179 (17)	0.027 (2)	0.031 (2)	0.0028 (18)	0.0079 (15)	0.0043 (18)
N4	0.0291 (18)	0.027 (2)	0.034 (2)	0.0080 (17)	0.0060 (16)	0.0060 (16)
C21	0.0214 (18)	0.020 (2)	0.0216 (18)	0.0018 (17)	0.0034 (14)	0.0026 (15)
S1	0.0247 (5)	0.0236 (6)	0.0326 (5)	0.0079 (4)	0.0072 (4)	0.0012 (4)
N5	0.0260 (18)	0.0229 (18)	0.0316 (19)	−0.0019 (15)	0.0071 (14)	0.0042 (15)
S2	0.0287 (5)	0.0326 (6)	0.0300 (6)	−0.0088 (5)	0.0087 (4)	0.0029 (5)
C22	0.0219 (18)	0.0156 (19)	0.028 (2)	−0.0021 (17)	−0.0032 (15)	0.0011 (16)

Geometric parameters (Å, º)

Zn1—N5	1.942 (3)	C9—H9	0.9500
Zn1—N1	2.039 (3)	C10—C11	1.389 (8)
Zn1—N3	2.061 (3)	C10—H10	0.9500
Zn1—N4	2.064 (4)	C11—C12	1.381 (7)
Zn1—N2	2.449 (3)	C11—H11	0.9500
N1—C5	1.350 (5)	C12—H12	0.9500
N1—C1	1.352 (5)	C13—C14	1.524 (5)
N2—C6	1.461 (5)	C13—C20	1.526 (5)
N2—C7	1.478 (5)	C13—H13	1.0000
N2—C13	1.510 (5)	C14—C19	1.392 (5)
N3—C8	1.342 (6)	C14—C15	1.397 (5)
N3—C12	1.344 (6)	C15—C16	1.385 (6)
C1—C2	1.370 (7)	C15—H15	0.9500
C1—H1	0.9500	C16—C17	1.384 (6)
C2—C3	1.383 (7)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.378 (6)
C3—C4	1.394 (6)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.387 (6)
C4—C5	1.378 (6)	C18—H18	0.9500
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.523 (5)	C20—H20A	0.9800
C6—H6A	0.9900	C20—H20B	0.9800
C6—H6B	0.9900	C20—H20C	0.9800
C7—C8	1.500 (6)	N4—C21	1.160 (5)
C7—H7A	0.9900	C21—S1	1.633 (4)
C7—H7B	0.9900	N5—C22	1.155 (5)
C8—C9	1.397 (6)	S2—C22	1.624 (4)
C9—C10	1.385 (7)
N5—Zn1—N1	108.46 (15)	N3—C8—C9	122.1 (4)
N5—Zn1—N3	123.55 (14)	N3—C8—C7	115.1 (4)
N1—Zn1—N3	123.46 (14)	C9—C8—C7	122.8 (4)
N5—Zn1—N4	101.43 (15)	C10—C9—C8	117.9 (5)
N1—Zn1—N4	99.36 (15)	C10—C9—H9	121.1
N3—Zn1—N4	91.21 (14)	C8—C9—H9	121.1
N5—Zn1—N2	102.49 (13)	C9—C10—C11	119.9 (4)
N1—Zn1—N2	74.73 (12)	C9—C10—H10	120.1
N3—Zn1—N2	73.99 (13)	C11—C10—H10	120.1
N4—Zn1—N2	156.01 (13)	C12—C11—C10	119.0 (5)
C5—N1—C1	118.4 (4)	C12—C11—H11	120.5
C5—N1—Zn1	122.4 (3)	C10—C11—H11	120.5
C1—N1—Zn1	119.1 (3)	N3—C12—C11	121.6 (5)
C6—N2—C7	110.6 (3)	N3—C12—H12	119.2
C6—N2—C13	114.7 (3)	C11—C12—H12	119.2
C7—N2—C13	110.9 (3)	N2—C13—C14	113.1 (3)
C6—N2—Zn1	105.5 (2)	N2—C13—C20	111.9 (3)
C7—N2—Zn1	94.5 (2)	C14—C13—C20	112.6 (3)
C13—N2—Zn1	118.8 (2)	N2—C13—H13	106.2
C8—N3—C12	119.6 (4)	C14—C13—H13	106.2
C8—N3—Zn1	117.1 (3)	C20—C13—H13	106.2
C12—N3—Zn1	123.2 (3)	C19—C14—C15	117.6 (4)
N1—C1—C2	122.4 (4)	C19—C14—C13	119.7 (4)
N1—C1—H1	118.8	C15—C14—C13	122.7 (4)
C2—C1—H1	118.8	C16—C15—C14	120.8 (4)
C1—C2—C3	119.2 (4)	C16—C15—H15	119.6
C1—C2—H2	120.4	C14—C15—H15	119.6
C3—C2—H2	120.4	C17—C16—C15	120.6 (4)
C2—C3—C4	118.9 (4)	C17—C16—H16	119.7
C2—C3—H3	120.5	C15—C16—H16	119.7
C4—C3—H3	120.5	C18—C17—C16	119.5 (4)
C5—C4—C3	118.9 (4)	C18—C17—H17	120.3
C5—C4—H4	120.5	C16—C17—H17	120.3
C3—C4—H4	120.5	C17—C18—C19	119.9 (4)
N1—C5—C4	122.1 (4)	C17—C18—H18	120.0
N1—C5—C6	117.6 (4)	C19—C18—H18	120.0
C4—C5—C6	120.3 (4)	C18—C19—C14	121.6 (4)
N2—C6—C5	112.1 (3)	C18—C19—H19	119.2
N2—C6—H6A	109.2	C14—C19—H19	119.2
C5—C6—H6A	109.2	C13—C20—H20A	109.5
N2—C6—H6B	109.2	C13—C20—H20B	109.5
C5—C6—H6B	109.2	H20A—C20—H20B	109.5
H6A—C6—H6B	107.9	C13—C20—H20C	109.5
N2—C7—C8	109.6 (3)	H20A—C20—H20C	109.5
N2—C7—H7A	109.7	H20B—C20—H20C	109.5
C8—C7—H7A	109.7	C21—N4—Zn1	171.6 (4)
N2—C7—H7B	109.7	N4—C21—S1	179.9 (5)
C8—C7—H7B	109.7	C22—N5—Zn1	170.3 (4)
H7A—C7—H7B	108.2	N5—C22—S2	178.5 (4)
C5—N1—C1—C2	0.3 (6)	N3—C8—C9—C10	0.9 (6)
Zn1—N1—C1—C2	−175.7 (4)	C7—C8—C9—C10	179.3 (3)
N1—C1—C2—C3	−1.2 (7)	C8—C9—C10—C11	0.4 (6)
C1—C2—C3—C4	1.4 (7)	C9—C10—C11—C12	−1.3 (6)
C2—C3—C4—C5	−0.8 (6)	C8—N3—C12—C11	0.4 (5)
C1—N1—C5—C4	0.3 (6)	Zn1—N3—C12—C11	−175.8 (3)
Zn1—N1—C5—C4	176.2 (3)	C10—C11—C12—N3	0.9 (7)
C1—N1—C5—C6	−177.4 (4)	C6—N2—C13—C14	70.2 (4)
Zn1—N1—C5—C6	−1.5 (5)	C7—N2—C13—C14	−56.0 (4)
C3—C4—C5—N1	0.0 (6)	Zn1—N2—C13—C14	−163.8 (2)
C3—C4—C5—C6	177.7 (4)	C6—N2—C13—C20	−58.3 (4)
C7—N2—C6—C5	−72.5 (4)	C7—N2—C13—C20	175.5 (3)
C13—N2—C6—C5	161.1 (3)	Zn1—N2—C13—C20	67.7 (4)
Zn1—N2—C6—C5	28.5 (4)	N2—C13—C14—C19	94.8 (4)
N1—C5—C6—N2	−21.4 (5)	C20—C13—C14—C19	−137.1 (4)
C4—C5—C6—N2	160.8 (3)	N2—C13—C14—C15	−85.5 (4)
C6—N2—C7—C8	161.8 (3)	C20—C13—C14—C15	42.7 (5)
C13—N2—C7—C8	−69.7 (4)	C19—C14—C15—C16	−0.1 (6)
Zn1—N2—C7—C8	53.4 (3)	C13—C14—C15—C16	−179.9 (4)
C12—N3—C8—C9	−1.3 (5)	C14—C15—C16—C17	−0.9 (7)
Zn1—N3—C8—C9	175.1 (3)	C15—C16—C17—C18	0.2 (7)
C12—N3—C8—C7	−179.8 (3)	C16—C17—C18—C19	1.5 (6)
Zn1—N3—C8—C7	−3.4 (4)	C17—C18—C19—C14	−2.5 (6)
N2—C7—C8—N3	−41.4 (4)	C15—C14—C19—C18	1.8 (6)
N2—C7—C8—C9	140.1 (4)	C13—C14—C19—C18	−178.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···S2^i	0.95	2.77	3.604 (5)	147
C11—H11···S1^ii	0.95	2.80	3.738 (5)	169

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