Crystal structure of di­chlorido­{2-methyl-2-[(pyridin-2-ylmeth­yl)amino]­propan-1-ol-κ³N,N′,O}copper(II) from synchrotron data

The Cu^II ion in the title compound shows a distorted square-pyramidal coordination geometry with two N and one O atoms of the mpmapOH ligand and two Cl anions. In the crystal, mol­ecules are connected by hydrogen bonds and π–π inter­actions, forming a strong supra­molecular network along the a-axis direction.

Key indicators

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.022
• wR factor = 0.061
• Data-to-parameter ratio = 24.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT019_ALERT_1_C _diffrn_measured_fraction_theta_full/*_max < 1.0      0.994 Report
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           5 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         39 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          1 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1    --  O1      ..        6.3 s.u.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT793_ALERT_4_G The Model has Chirality at N2      (Centro SPGR)          S Verify
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1     (II)    .....       2.16 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          3 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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 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: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Putz & Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).

Dichlorido{2-methyl-2-[(pyridin-2-ylmethyl)amino]propan-1-ol-κ³N,N',O}copper(II)

Crystal data

[CuCl2(C10H16N2O)]	F(000) = 644
Mr = 314.69	Dx = 1.652 Mg m^−3
Monoclinic, P21/n	Synchrotron radiation, λ = 0.610 Å
a = 8.4470 (17) Å	Cell parameters from 24265 reflections
b = 9.895 (2) Å	θ = 0.4–33.7°
c = 15.254 (3) Å	µ = 1.40 mm^−1
β = 97.13 (3)°	T = 100 K
V = 1265.1 (5) Å^3	Block, blue
Z = 4	0.12 × 0.10 × 0.09 mm

Data collection

ADSC Q210 CCD area detector diffractometer	3556 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnet	Rint = 0.031
ω scan	θmax = 25.5°, θmin = 2.9°
Absorption correction: empirical (using intensity measurements) (HKL3000 Scalepack; Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.809, Tmax = 0.887	k = −13→13
11018 measured reflections	l = −21→21
3674 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 0.6535P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.004
3674 reflections	Δρmax = 0.51 e Å^−3
148 parameters	Δρmin = −0.90 e Å^−3

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
Cu1	0.28124 (2)	0.60310 (2)	0.68527 (2)	0.00421 (5)
Cl1	0.19986 (4)	0.77197 (3)	0.59216 (2)	0.01365 (7)
Cl2	0.02903 (3)	0.50366 (3)	0.72731 (2)	0.01123 (7)
O1	0.31493 (9)	0.73256 (8)	0.79008 (5)	0.00605 (14)
H1O1	0.3621 (18)	0.8042 (12)	0.7791 (11)	0.007*
N1	0.32349 (11)	0.46940 (9)	0.59369 (6)	0.00555 (16)
N2	0.43588 (10)	0.48634 (9)	0.76378 (6)	0.00424 (15)
H2N2	0.3706	0.4292	0.7998	0.005*
C1	0.24193 (13)	0.46123 (12)	0.51215 (7)	0.00921 (19)
H1	0.1599	0.5252	0.4952	0.011*
C2	0.27367 (14)	0.36289 (13)	0.45236 (7)	0.0113 (2)
H2	0.2134	0.3580	0.3956	0.014*
C3	0.39622 (14)	0.27116 (13)	0.47736 (8)	0.0121 (2)
H3	0.4234	0.2046	0.4369	0.015*
C4	0.47810 (13)	0.27800 (12)	0.56195 (8)	0.0103 (2)
H4	0.5602	0.2149	0.5806	0.012*
C5	0.43811 (12)	0.37864 (11)	0.61898 (7)	0.00587 (18)
C6	0.52329 (13)	0.39249 (11)	0.71132 (7)	0.00744 (19)
H6A	0.5317	0.3028	0.7402	0.009*
H6B	0.6326	0.4270	0.7088	0.009*
C7	0.53496 (12)	0.57791 (11)	0.82728 (7)	0.00457 (17)
C8	0.64485 (12)	0.66575 (11)	0.77880 (7)	0.00812 (18)
H8A	0.7355	0.6116	0.7647	0.012*
H8B	0.6840	0.7418	0.8166	0.012*
H8C	0.5856	0.7002	0.7241	0.012*
C9	0.63253 (14)	0.49822 (12)	0.90080 (7)	0.00968 (19)
H9A	0.5613	0.4402	0.9303	0.015*
H9B	0.6878	0.5611	0.9438	0.015*
H9C	0.7111	0.4422	0.8755	0.015*
C10	0.40927 (12)	0.66639 (11)	0.86317 (7)	0.00648 (18)
H10A	0.3397	0.6100	0.8960	0.008*
H10B	0.4620	0.7348	0.9042	0.008*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.00445 (7)	0.00330 (8)	0.00458 (7)	0.00238 (4)	−0.00066 (5)	−0.00020 (4)
Cl1	0.02298 (14)	0.00915 (13)	0.00860 (12)	0.00964 (10)	0.00104 (10)	0.00304 (9)
Cl2	0.00569 (11)	0.00647 (12)	0.02190 (14)	0.00083 (8)	0.00314 (9)	−0.00072 (9)
O1	0.0060 (3)	0.0038 (3)	0.0080 (3)	0.0009 (2)	−0.0002 (3)	−0.0005 (3)
N1	0.0066 (4)	0.0049 (4)	0.0051 (4)	0.0009 (3)	0.0002 (3)	−0.0002 (3)
N2	0.0039 (3)	0.0036 (4)	0.0049 (4)	0.0009 (3)	−0.0006 (3)	−0.0007 (3)
C1	0.0101 (4)	0.0106 (5)	0.0063 (4)	0.0002 (4)	−0.0013 (3)	0.0003 (4)
C2	0.0132 (5)	0.0143 (5)	0.0063 (4)	−0.0032 (4)	0.0002 (4)	−0.0024 (4)
C3	0.0117 (5)	0.0143 (5)	0.0107 (5)	−0.0017 (4)	0.0025 (4)	−0.0074 (4)
C4	0.0077 (4)	0.0095 (5)	0.0133 (5)	0.0017 (4)	0.0002 (4)	−0.0067 (4)
C5	0.0048 (4)	0.0057 (4)	0.0070 (4)	−0.0004 (3)	0.0005 (3)	−0.0020 (3)
C6	0.0073 (4)	0.0061 (5)	0.0082 (4)	0.0040 (3)	−0.0017 (4)	−0.0034 (3)
C7	0.0044 (4)	0.0045 (4)	0.0044 (4)	0.0000 (3)	−0.0009 (3)	−0.0010 (3)
C8	0.0057 (4)	0.0071 (4)	0.0118 (5)	−0.0012 (3)	0.0024 (3)	0.0006 (4)
C9	0.0106 (5)	0.0094 (5)	0.0076 (4)	0.0016 (4)	−0.0044 (4)	0.0005 (4)
C10	0.0068 (4)	0.0074 (4)	0.0053 (4)	0.0018 (3)	0.0007 (3)	−0.0011 (3)

Geometric parameters (Å, º)

Cu1—N1	1.9881 (10)	C3—H3	0.9500
Cu1—N2	2.0217 (10)	C4—C5	1.3913 (15)
Cu1—O1	2.0409 (9)	C4—H4	0.9500
Cu1—Cl1	2.2448 (5)	C5—C6	1.5063 (16)
Cu1—Cl2	2.5014 (6)	C6—H6A	0.9900
O1—C10	1.4444 (13)	C6—H6B	0.9900
O1—H1O1	0.840 (9)	C7—C9	1.5262 (15)
N1—C5	1.3417 (14)	C7—C8	1.5278 (15)
N1—C1	1.3474 (14)	C7—C10	1.5289 (14)
N2—C6	1.4814 (13)	C8—H8A	0.9800
N2—C7	1.5028 (14)	C8—H8B	0.9800
N2—H2N2	1.0000	C8—H8C	0.9800
C1—C2	1.3825 (16)	C9—H9A	0.9800
C1—H1	0.9500	C9—H9B	0.9800
C2—C3	1.3938 (17)	C9—H9C	0.9800
C2—H2	0.9500	C10—H10A	0.9900
C3—C4	1.3880 (16)	C10—H10B	0.9900
N1—Cu1—N2	82.92 (4)	N1—C5—C4	121.46 (10)
N1—Cu1—O1	161.51 (4)	N1—C5—C6	116.87 (9)
N2—Cu1—O1	82.97 (4)	C4—C5—C6	121.67 (10)
N1—Cu1—Cl1	96.80 (3)	N2—C6—C5	110.48 (9)
N2—Cu1—Cl1	157.64 (3)	N2—C6—H6A	109.6
O1—Cu1—Cl1	91.74 (3)	C5—C6—H6A	109.6
N1—Cu1—Cl2	98.69 (3)	N2—C6—H6B	109.6
N2—Cu1—Cl2	97.56 (3)	C5—C6—H6B	109.6
O1—Cu1—Cl2	94.96 (3)	H6A—C6—H6B	108.1
Cl1—Cu1—Cl2	104.55 (2)	N2—C7—C9	111.65 (9)
C10—O1—Cu1	109.28 (6)	N2—C7—C8	110.75 (8)
C10—O1—H1O1	107.8 (12)	C9—C7—C8	110.15 (9)
Cu1—O1—H1O1	113.4 (12)	N2—C7—C10	102.72 (8)
C5—N1—C1	119.56 (10)	C9—C7—C10	111.62 (9)
C5—N1—Cu1	115.43 (7)	C8—C7—C10	109.76 (9)
C1—N1—Cu1	124.94 (8)	C7—C8—H8A	109.5
C6—N2—C7	116.81 (8)	C7—C8—H8B	109.5
C6—N2—Cu1	111.52 (7)	H8A—C8—H8B	109.5
C7—N2—Cu1	107.72 (7)	C7—C8—H8C	109.5
C6—N2—H2N2	106.7	H8A—C8—H8C	109.5
C7—N2—H2N2	106.7	H8B—C8—H8C	109.5
Cu1—N2—H2N2	106.7	C7—C9—H9A	109.5
N1—C1—C2	122.17 (11)	C7—C9—H9B	109.5
N1—C1—H1	118.9	H9A—C9—H9B	109.5
C2—C1—H1	118.9	C7—C9—H9C	109.5
C1—C2—C3	118.43 (11)	H9A—C9—H9C	109.5
C1—C2—H2	120.8	H9B—C9—H9C	109.5
C3—C2—H2	120.8	O1—C10—C7	108.92 (8)
C4—C3—C2	119.35 (11)	O1—C10—H10A	109.9
C4—C3—H3	120.3	C7—C10—H10A	109.9
C2—C3—H3	120.3	O1—C10—H10B	109.9
C3—C4—C5	118.99 (11)	C7—C10—H10B	109.9
C3—C4—H4	120.5	H10A—C10—H10B	108.3
C5—C4—H4	120.5
C5—N1—C1—C2	−0.93 (17)	N1—C5—C6—N2	13.48 (13)
Cu1—N1—C1—C2	−177.79 (9)	C4—C5—C6—N2	−167.61 (10)
N1—C1—C2—C3	−1.17 (18)	C6—N2—C7—C9	−64.80 (12)
C1—C2—C3—C4	2.37 (18)	Cu1—N2—C7—C9	168.82 (7)
C2—C3—C4—C5	−1.55 (18)	C6—N2—C7—C8	58.33 (12)
C1—N1—C5—C4	1.81 (16)	Cu1—N2—C7—C8	−68.04 (9)
Cu1—N1—C5—C4	178.96 (9)	C6—N2—C7—C10	175.47 (8)
C1—N1—C5—C6	−179.28 (10)	Cu1—N2—C7—C10	49.09 (8)
Cu1—N1—C5—C6	−2.13 (12)	Cu1—O1—C10—C7	37.17 (9)
C3—C4—C5—N1	−0.56 (17)	N2—C7—C10—O1	−56.79 (10)
C3—C4—C5—C6	−179.42 (11)	C9—C7—C10—O1	−176.54 (8)
C7—N2—C6—C5	−142.45 (9)	C8—C7—C10—O1	61.04 (11)
Cu1—N2—C6—C5	−17.98 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···Cl2^i	0.84 (1)	2.19 (1)	3.0151 (10)	170 (2)
N2—H2N2···Cl1^ii	1.00	2.40	3.3568 (11)	161

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