Crystal structure of [2-({2-[(2-azanidyl­benzyl­idene)amino]­benzyl­idene}amino)-4-chloro­phenol­ato]nickel(II)

The metal atom of the title compound is four coordinated. The asymmetrically appended Cl atom and a widely spread π-conjugated system of the complex mol­ecule construct the supra­molecular structures of a hydrogen-bonded chain and a π–π inter­acted column.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.103
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.65 Report
PLAT410_ALERT_2_C Short Intra H...H Contact   H12    ..  H14     .       1.93 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.641 Check
PLAT975_ALERT_2_C Check Calcd Residual Density  0.77A From      N3       0.43 eA-3

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/c        P21/n Note
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ni1    --  N1      ..        5.1 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ni1    --  N2      ..        5.5 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ni1    --  N3      ..        5.3 s.u.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT882_ALERT_1_G Missing datum for _diffrn_reflns_av_unetI/netI .     Please Check
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          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 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
  10 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1995); cell refinement: RAPID-AUTO (Rigaku, 1995); data reduction: RAPID-AUTO (Rigaku, 1995); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: CrystalStructure (Rigaku, 2014); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).

[2-({2-[(2-Azanidylbenzylidene)amino]benzylidene}amino)-4-chlorophenolato]nickel(II)

Crystal data

[Ni(C20H14ClN3O)]	F(000) = 832.00
Mr = 406.50	Dx = 1.678 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 7.5510 (4) Å	Cell parameters from 13442 reflections
b = 17.8689 (9) Å	θ = 3.0–27.4°
c = 12.6834 (6) Å	µ = 1.39 mm^−1
β = 109.9504 (14)°	T = 100 K
V = 1608.64 (14) Å^3	Block, purple
Z = 4	0.46 × 0.27 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	3177 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.039
ω scans	θmax = 27.4°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→8
Tmin = 0.476, Tmax = 0.712	k = −23→23
15243 measured reflections	l = −16→16
3638 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 1.948P] where P = (Fo^2 + 2Fc^2)/3
3638 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 1.35 e Å^−3
1 restraint	Δρmin = −0.37 e Å^−3
Primary atom site location: structure-invariant direct methods

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.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Ni1	0.29838 (4)	0.53846 (2)	0.46051 (3)	0.01597 (11)
Cl1	0.22371 (10)	0.39200 (4)	0.93185 (6)	0.03146 (17)
O1	0.3645 (3)	0.58686 (10)	0.59854 (15)	0.0230 (4)
N1	0.2079 (3)	0.46083 (11)	0.52811 (18)	0.0195 (4)
N2	0.2225 (3)	0.49436 (12)	0.31594 (18)	0.0193 (4)
N3	0.3976 (3)	0.62220 (12)	0.41867 (19)	0.0221 (4)
C1	0.3301 (4)	0.54570 (14)	0.6762 (2)	0.0205 (5)
C2	0.3738 (4)	0.56917 (15)	0.7885 (2)	0.0229 (5)
C3	0.3380 (4)	0.52243 (15)	0.8656 (2)	0.0237 (5)
C4	0.2594 (4)	0.45198 (15)	0.8321 (2)	0.0236 (5)
C5	0.2109 (4)	0.42792 (15)	0.7223 (2)	0.0224 (5)
C6	0.2447 (4)	0.47561 (15)	0.6445 (2)	0.0207 (5)
C7	0.1169 (4)	0.40146 (14)	0.4813 (2)	0.0210 (5)
C8	0.0936 (3)	0.37840 (14)	0.3689 (2)	0.0197 (5)
C9	0.0092 (4)	0.30739 (15)	0.3366 (2)	0.0235 (5)
C10	−0.0089 (4)	0.27609 (15)	0.2338 (2)	0.0259 (6)
C11	0.0649 (4)	0.31435 (15)	0.1634 (2)	0.0251 (5)
C12	0.1469 (4)	0.38395 (15)	0.1918 (2)	0.0230 (5)
C13	0.1542 (3)	0.41975 (13)	0.2923 (2)	0.0187 (5)
C14	0.2147 (4)	0.53457 (14)	0.2259 (2)	0.0199 (5)
C15	0.2954 (4)	0.60452 (14)	0.2207 (2)	0.0214 (5)
C16	0.2781 (4)	0.63380 (15)	0.1133 (2)	0.0247 (5)
C17	0.3660 (4)	0.69883 (15)	0.1023 (2)	0.0262 (5)
C18	0.4758 (4)	0.73809 (15)	0.2007 (2)	0.0267 (6)
C19	0.4922 (4)	0.71300 (14)	0.3054 (2)	0.0253 (6)
C20	0.3979 (3)	0.64586 (14)	0.3194 (2)	0.0210 (5)
H1	0.452 (4)	0.6459 (17)	0.478 (2)	0.0315*
H2	0.42785	0.61711	0.81103	0.0275*
H3	0.36681	0.5382	0.94116	0.0285*
H5	0.15584	0.38005	0.70055	0.0268*
H7	0.06228	0.37131	0.52382	0.0253*
H9	−0.03614	0.28057	0.38682	0.0282*
H10	−0.07053	0.22937	0.21193	0.0310*
H11	0.05913	0.2923	0.09418	0.0301*
H12	0.19936	0.40819	0.14264	0.0276*
H14	0.14485	0.51283	0.15561	0.0239*
H16	0.2041	0.60767	0.04782	0.0296*
H17	0.35399	0.71755	0.03007	0.0314*
H18	0.53905	0.7827	0.19338	0.0321*
H19	0.56662	0.74021	0.36959	0.0304*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.01684 (17)	0.01610 (17)	0.01561 (17)	0.00035 (11)	0.00636 (13)	0.00011 (12)
Cl1	0.0320 (4)	0.0439 (4)	0.0214 (3)	−0.0047 (3)	0.0130 (3)	0.0036 (3)
O1	0.0285 (10)	0.0222 (9)	0.0181 (9)	0.0016 (8)	0.0076 (8)	−0.0014 (7)
N1	0.0167 (10)	0.0209 (11)	0.0216 (11)	0.0035 (8)	0.0072 (9)	0.0015 (8)
N2	0.0177 (10)	0.0202 (10)	0.0215 (10)	0.0012 (8)	0.0088 (9)	0.0001 (8)
N3	0.0210 (11)	0.0203 (11)	0.0238 (11)	0.0001 (9)	0.0062 (9)	−0.0002 (9)
C1	0.0183 (12)	0.0243 (13)	0.0183 (12)	0.0059 (10)	0.0054 (10)	0.0001 (10)
C2	0.0230 (12)	0.0228 (12)	0.0200 (12)	0.0049 (10)	0.0036 (10)	−0.0025 (10)
C3	0.0204 (12)	0.0315 (14)	0.0190 (12)	0.0063 (11)	0.0064 (10)	−0.0022 (11)
C4	0.0198 (12)	0.0304 (14)	0.0222 (13)	0.0036 (10)	0.0092 (10)	0.0040 (11)
C5	0.0180 (12)	0.0254 (13)	0.0241 (13)	0.0006 (10)	0.0078 (10)	−0.0024 (11)
C6	0.0171 (11)	0.0261 (13)	0.0196 (12)	0.0047 (10)	0.0070 (10)	−0.0001 (10)
C7	0.0188 (12)	0.0246 (13)	0.0211 (12)	0.0017 (10)	0.0085 (10)	0.0024 (10)
C8	0.0160 (11)	0.0228 (12)	0.0197 (12)	0.0032 (9)	0.0055 (10)	0.0023 (10)
C9	0.0195 (12)	0.0238 (13)	0.0276 (13)	−0.0001 (10)	0.0085 (11)	0.0055 (11)
C10	0.0218 (13)	0.0217 (12)	0.0310 (14)	−0.0024 (10)	0.0049 (11)	−0.0047 (11)
C11	0.0241 (13)	0.0267 (13)	0.0221 (13)	0.0019 (11)	0.0048 (11)	−0.0039 (11)
C12	0.0252 (13)	0.0232 (13)	0.0206 (12)	0.0038 (10)	0.0077 (11)	0.0003 (10)
C13	0.0167 (11)	0.0183 (12)	0.0209 (12)	0.0025 (9)	0.0062 (10)	0.0012 (10)
C14	0.0189 (12)	0.0216 (12)	0.0203 (12)	0.0019 (10)	0.0080 (10)	−0.0009 (10)
C15	0.0207 (12)	0.0182 (12)	0.0279 (13)	0.0029 (10)	0.0115 (11)	0.0015 (10)
C16	0.0242 (13)	0.0246 (13)	0.0274 (14)	0.0022 (11)	0.0116 (11)	−0.0010 (11)
C17	0.0302 (14)	0.0236 (13)	0.0291 (14)	0.0032 (11)	0.0158 (12)	0.0052 (11)
C18	0.0273 (13)	0.0204 (12)	0.0364 (15)	0.0002 (11)	0.0160 (12)	0.0038 (11)
C19	0.0216 (12)	0.0211 (13)	0.0330 (15)	−0.0002 (10)	0.0087 (11)	0.0007 (11)
C20	0.0165 (11)	0.0193 (12)	0.0285 (13)	0.0055 (9)	0.0094 (10)	0.0044 (10)

Geometric parameters (Å, º)

Ni1—N3	1.831 (2)	C8—C13	1.416 (3)
Ni1—O1	1.8617 (18)	C8—C9	1.416 (4)
Ni1—N1	1.878 (2)	C9—C10	1.382 (4)
Ni1—N2	1.896 (2)	C9—H9	0.9500
Cl1—C4	1.748 (3)	C10—C11	1.383 (4)
O1—C1	1.324 (3)	C10—H10	0.9500
N1—C7	1.293 (3)	C11—C12	1.381 (4)
N1—C6	1.430 (3)	C11—H11	0.9500
N2—C14	1.333 (3)	C12—C13	1.410 (3)
N2—C13	1.424 (3)	C12—H12	0.9500
N3—C20	1.329 (3)	C14—C15	1.402 (3)
N3—H1	0.836 (18)	C14—H14	0.9500
C1—C6	1.403 (4)	C15—C16	1.424 (4)
C1—C2	1.412 (3)	C15—C20	1.432 (4)
C2—C3	1.381 (4)	C16—C17	1.369 (4)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.395 (4)	C17—C18	1.425 (4)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.382 (4)	C18—C19	1.367 (4)
C5—C6	1.392 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.436 (4)
C7—C8	1.436 (3)	C19—H19	0.9500
C7—H7	0.9500
N3—Ni1—O1	83.57 (9)	C13—C8—C7	125.0 (2)
N3—Ni1—N1	169.92 (10)	C9—C8—C7	115.8 (2)
O1—Ni1—N1	86.35 (9)	C10—C9—C8	121.7 (2)
N3—Ni1—N2	94.46 (10)	C10—C9—H9	119.1
O1—Ni1—N2	176.53 (9)	C8—C9—H9	119.1
N1—Ni1—N2	95.61 (9)	C9—C10—C11	118.5 (2)
C1—O1—Ni1	112.57 (16)	C9—C10—H10	120.8
C7—N1—C6	120.7 (2)	C11—C10—H10	120.8
C7—N1—Ni1	128.02 (18)	C12—C11—C10	121.4 (3)
C6—N1—Ni1	111.23 (16)	C12—C11—H11	119.3
C14—N2—C13	114.6 (2)	C10—C11—H11	119.3
C14—N2—Ni1	121.00 (18)	C11—C12—C13	121.3 (2)
C13—N2—Ni1	124.14 (16)	C11—C12—H12	119.3
C20—N3—Ni1	131.89 (19)	C13—C12—H12	119.3
C20—N3—H1	122 (2)	C12—C13—C8	117.5 (2)
Ni1—N3—H1	106 (2)	C12—C13—N2	121.0 (2)
O1—C1—C6	118.0 (2)	C8—C13—N2	121.5 (2)
O1—C1—C2	123.2 (2)	N2—C14—C15	128.9 (2)
C6—C1—C2	118.7 (2)	N2—C14—H14	115.6
C3—C2—C1	120.0 (3)	C15—C14—H14	115.6
C3—C2—H2	120.0	C14—C15—C16	118.3 (2)
C1—C2—H2	120.0	C14—C15—C20	122.2 (2)
C2—C3—C4	119.7 (2)	C16—C15—C20	119.5 (2)
C2—C3—H3	120.1	C17—C16—C15	121.3 (3)
C4—C3—H3	120.1	C17—C16—H16	119.3
C5—C4—C3	121.8 (2)	C15—C16—H16	119.3
C5—C4—Cl1	119.0 (2)	C16—C17—C18	119.1 (3)
C3—C4—Cl1	119.2 (2)	C16—C17—H17	120.5
C4—C5—C6	118.3 (2)	C18—C17—H17	120.5
C4—C5—H5	120.8	C19—C18—C17	121.5 (2)
C6—C5—H5	120.8	C19—C18—H18	119.3
C5—C6—C1	121.4 (2)	C17—C18—H18	119.3
C5—C6—N1	126.9 (2)	C18—C19—C20	120.6 (3)
C1—C6—N1	111.7 (2)	C18—C19—H19	119.7
N1—C7—C8	123.8 (2)	C20—C19—H19	119.7
N1—C7—H7	118.1	N3—C20—C15	119.2 (2)
C8—C7—H7	118.1	N3—C20—C19	122.9 (2)
C13—C8—C9	119.2 (2)	C15—C20—C19	117.8 (2)
N3—Ni1—O1—C1	−176.59 (18)	Ni1—N1—C7—C8	10.2 (4)
N1—Ni1—O1—C1	3.42 (17)	N1—C7—C8—C13	−4.8 (4)
N3—Ni1—N1—C7	173.9 (5)	N1—C7—C8—C9	172.8 (2)
O1—Ni1—N1—C7	174.0 (2)	C13—C8—C9—C10	2.6 (4)
N2—Ni1—N1—C7	−3.1 (2)	C7—C8—C9—C10	−175.2 (2)
N3—Ni1—N1—C6	−3.6 (6)	C8—C9—C10—C11	2.7 (4)
O1—Ni1—N1—C6	−3.50 (16)	C9—C10—C11—C12	−3.2 (4)
N2—Ni1—N1—C6	179.37 (16)	C10—C11—C12—C13	−1.7 (4)
N3—Ni1—N2—C14	−15.0 (2)	C11—C12—C13—C8	6.9 (4)
N1—Ni1—N2—C14	164.51 (19)	C11—C12—C13—N2	−173.9 (2)
N3—Ni1—N2—C13	170.91 (19)	C9—C8—C13—C12	−7.2 (3)
N1—Ni1—N2—C13	−9.6 (2)	C7—C8—C13—C12	170.3 (2)
O1—Ni1—N3—C20	−171.4 (2)	C9—C8—C13—N2	173.6 (2)
N1—Ni1—N3—C20	−171.3 (4)	C7—C8—C13—N2	−8.9 (4)
N2—Ni1—N3—C20	5.7 (2)	C14—N2—C13—C12	22.3 (3)
Ni1—O1—C1—C6	−2.6 (3)	Ni1—N2—C13—C12	−163.25 (19)
Ni1—O1—C1—C2	177.86 (19)	C14—N2—C13—C8	−158.5 (2)
O1—C1—C2—C3	−178.4 (2)	Ni1—N2—C13—C8	15.9 (3)
C6—C1—C2—C3	2.1 (4)	C13—N2—C14—C15	−169.2 (2)
C1—C2—C3—C4	0.3 (4)	Ni1—N2—C14—C15	16.1 (4)
C2—C3—C4—C5	−1.8 (4)	N2—C14—C15—C16	175.5 (2)
C2—C3—C4—Cl1	177.5 (2)	N2—C14—C15—C20	−2.7 (4)
C3—C4—C5—C6	0.9 (4)	C14—C15—C16—C17	−174.8 (2)
Cl1—C4—C5—C6	−178.37 (19)	C20—C15—C16—C17	3.5 (4)
C4—C5—C6—C1	1.5 (4)	C15—C16—C17—C18	−0.4 (4)
C4—C5—C6—N1	178.9 (2)	C16—C17—C18—C19	−1.3 (4)
O1—C1—C6—C5	177.4 (2)	C17—C18—C19—C20	−0.2 (4)
C2—C1—C6—C5	−3.0 (4)	Ni1—N3—C20—C15	4.8 (4)
O1—C1—C6—N1	−0.2 (3)	Ni1—N3—C20—C19	−177.35 (19)
C2—C1—C6—N1	179.3 (2)	C14—C15—C20—N3	−8.6 (4)
C7—N1—C6—C5	7.7 (4)	C16—C15—C20—N3	173.2 (2)
Ni1—N1—C6—C5	−174.6 (2)	C14—C15—C20—C19	173.4 (2)
C7—N1—C6—C1	−174.8 (2)	C16—C15—C20—C19	−4.8 (3)
Ni1—N1—C6—C1	2.9 (3)	C18—C19—C20—N3	−174.7 (2)
C6—N1—C7—C8	−172.5 (2)	C18—C19—C20—C15	3.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl1^i	0.95	2.76	3.540 (3)	140
C10—H10···C20^ii	0.95	2.80	3.626 (4)	146

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