Chlorido­(2-{(2-hy­droxy­eth­yl)[tris­(hy­droxy­meth­yl)meth­yl]amino}­ethano­lato-κ⁵N,O,O′,O′′,O′′′)copper(II)

The title complex, [Cu(C₈H₁₈NO₅)Cl] or [Cu(H₄bis-tris­)Cl], was obtained starting from the previously reported [Cu(H₅bis-tris­)Cl]Cl compound. The deprotonation of the amino­polyol ligand H₅bis-tris {[bis­(2-hy­droxy­eth­yl)amino]­tris­(hy­droxy­meth­yl)methane, C₈H₁₉NO₅} promotes the formation of a very strong O—H...O inter­molecular hydrogen bond, characterized by an H...O separation of 1.553 (19) Å and an O—H...O angle of 178 (4)°. The remaining hy­droxy groups are also engaged in hydrogen bonds, forming R₂²(8), R₄⁴(16), R₄⁴(20) and R₄⁴(22) ring motifs, which stabilize the triperiodic supra­molecular network.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 109 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.130
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT410_ALERT_2_B Short Intra H...H Contact  H4A      ..H7A      .       1.89 Ang.
                                                      x,y,z  =      1_555 Check

Alert level C
PLAT112_ALERT_2_C ADDSYM Detects New (Pseudo) Symm. Elem         B         87 %Fit
PLAT213_ALERT_2_C Atom O2              has ADP max/min Ratio .....        3.3 prolat
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.79Ang From O3      .       0.57 eA-3
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.80Ang From O3      .       0.47 eA-3
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  1.06Ang From O1      .       0.43 eA-3
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.75Ang From O4      .       0.41 eA-3
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  1.08Ang From O2      .      -0.59 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H2        .      -0.34 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H4B      ..CL1      .       2.97 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H5A      ..CL1      .       2.97 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H7B      ..CL1      .       2.85 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H8B      ..O1       .       2.65 Ang.
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C4       ..CL1      .        157 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C5       ..CL1      .        155 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C7       ..CL1      .        148 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C8       ..O1       .        157 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1       (II)      .       2.18 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
               -1  0  1,   1  0  1,   0  1  1,   0  0  2,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        478 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        2.1 Low
PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ.          2 Units
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ.          2 Units
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       1.95 Note
              Predicted wR2: Based on SigI   2  6.65 or SHELX Weight 12.82       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 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
  10 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

Chlorido(2-{(2-hydroxyethyl)[tris(hydroxymethyl)methyl]amino}ethanolato-κ⁵N,O,O',O'',O''')copper(II)

Crystal data

[Cu(C8H18NO5)Cl]	Dx = 1.844 Mg m^−3
Mr = 307.22	Melting point: 435 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2605 (9) Å	Cell parameters from 1395 reflections
b = 10.4221 (14) Å	θ = 3.4–29.6°
c = 14.668 (2) Å	µ = 2.22 mm^−1
β = 94.366 (12)°	T = 109 K
V = 1106.7 (3) Å^3	Prism, blue
Z = 4	0.17 × 0.06 × 0.04 mm
F(000) = 636

Data collection

Xcalibur, Atlas, Gemini diffractometer	2582 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2002 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 10.4685 pixels mm^-1	θmax = 29.6°, θmin = 3.4°
ω scans	h = −9→10
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2022)	k = −14→13
Tmin = 0.848, Tmax = 0.917	l = −18→18
5523 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: mixed
wR(F^2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0646P)^2] where P = (Fo^2 + 2Fc^2)/3
2582 reflections	(Δ/σ)max = 0.001
157 parameters	Δρmax = 1.18 e Å^−3
4 restraints	Δρmin = −1.17 e Å^−3
0 constraints

Special details

Refinement. Methylene H atoms were refined using a riding model (C—H: 0.99 Å); hydroxy H atoms (H1, H2, H3, H4) were located from electron-difference maps and were refined freely, with the O—H bond lengths restrained to 0.85 (2) Å.

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

	x	y	z	Uiso*/Ueq
Cu1	0.22842 (5)	0.75373 (4)	0.75931 (3)	0.00775 (16)
Cl1	0.31899 (12)	0.76196 (8)	0.61387 (6)	0.0145 (2)
O1	0.2269 (3)	0.8024 (2)	1.09572 (16)	0.0130 (5)
H1	0.116 (3)	0.790 (4)	1.103 (3)	0.019*
O2	0.3908 (3)	0.6168 (2)	0.80600 (16)	0.0096 (5)
H2	0.407 (5)	0.539 (2)	0.790 (3)	0.014*
O3	0.4592 (3)	0.8730 (2)	0.84389 (17)	0.0143 (5)
H3	0.462 (5)	0.9507 (19)	0.836 (3)	0.022*
O4	−0.0338 (3)	0.6104 (2)	0.72784 (16)	0.0104 (5)
H4	−0.113 (4)	0.641 (4)	0.692 (2)	0.016*
O5	0.0620 (3)	0.8995 (2)	0.74310 (16)	0.0111 (5)
N1	0.1319 (4)	0.7390 (2)	0.8869 (2)	0.0075 (6)
C1	0.3128 (5)	0.7294 (3)	0.9443 (2)	0.0080 (7)
C2	0.2964 (5)	0.6976 (3)	1.0446 (2)	0.0121 (7)
H2A	0.213089	0.622927	1.048817	0.015*
H2B	0.419525	0.672641	1.072706	0.015*
C3	0.4235 (4)	0.6194 (3)	0.9021 (2)	0.0109 (7)
H3A	0.557130	0.631837	0.918562	0.013*
H3B	0.386836	0.536144	0.927768	0.013*
C4	0.4244 (4)	0.8542 (3)	0.9372 (2)	0.0104 (7)
H4A	0.353726	0.927666	0.959330	0.012*
H4B	0.542532	0.847779	0.975361	0.012*
C5	0.0232 (4)	0.6181 (3)	0.8917 (2)	0.0096 (7)
H5A	−0.039617	0.617991	0.949336	0.012*
H5B	0.109414	0.544400	0.893907	0.012*
C6	−0.1206 (4)	0.5993 (3)	0.8123 (2)	0.0118 (7)
H6A	−0.178021	0.513531	0.816363	0.014*
H6B	−0.218735	0.664857	0.814672	0.014*
C7	0.0172 (4)	0.8544 (3)	0.9019 (2)	0.0094 (7)
H7A	0.095096	0.922177	0.932473	0.011*
H7B	−0.081487	0.832157	0.942142	0.011*
C8	−0.0692 (4)	0.9044 (3)	0.8101 (2)	0.0114 (7)
H8A	−0.177933	0.851406	0.789966	0.014*
H8B	−0.111298	0.993927	0.817219	0.014*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0099 (3)	0.0069 (2)	0.0065 (2)	0.00093 (15)	0.00096 (17)	0.00036 (15)
Cl1	0.0135 (4)	0.0219 (5)	0.0084 (4)	0.0024 (3)	0.0025 (3)	0.0011 (3)
O1	0.0108 (11)	0.0173 (13)	0.0108 (13)	−0.0005 (11)	0.0007 (9)	−0.0040 (11)
O2	0.0163 (11)	0.0046 (11)	0.0080 (12)	0.0047 (10)	0.0018 (9)	−0.0025 (10)
O3	0.0218 (12)	0.0108 (11)	0.0110 (13)	−0.0061 (11)	0.0049 (10)	0.0006 (11)
O4	0.0128 (11)	0.0111 (12)	0.0073 (12)	−0.0009 (10)	−0.0007 (9)	0.0000 (10)
O5	0.0154 (11)	0.0085 (11)	0.0100 (12)	0.0031 (10)	0.0037 (9)	0.0011 (10)
N1	0.0095 (13)	0.0039 (13)	0.0088 (14)	0.0006 (10)	−0.0011 (11)	−0.0011 (11)
C1	0.0085 (15)	0.0082 (15)	0.0070 (16)	−0.0009 (13)	−0.0022 (12)	−0.0015 (13)
C2	0.0128 (16)	0.0119 (16)	0.0114 (18)	0.0007 (14)	−0.0012 (13)	−0.0009 (15)
C3	0.0114 (15)	0.0090 (16)	0.0121 (18)	0.0007 (14)	−0.0011 (12)	0.0020 (14)
C4	0.0120 (15)	0.0078 (16)	0.0112 (18)	−0.0019 (14)	0.0001 (12)	−0.0028 (13)
C5	0.0119 (15)	0.0090 (15)	0.0075 (16)	−0.0004 (14)	−0.0013 (12)	0.0018 (14)
C6	0.0137 (15)	0.0113 (16)	0.0101 (17)	−0.0055 (14)	−0.0015 (12)	0.0021 (14)
C7	0.0102 (15)	0.0105 (16)	0.0076 (17)	0.0038 (13)	0.0010 (12)	0.0011 (13)
C8	0.0124 (15)	0.0115 (16)	0.0102 (17)	0.0004 (14)	0.0012 (12)	0.0014 (14)

Geometric parameters (Å, º)

Cu1—O2	1.943 (2)	C1—C4	1.540 (4)
Cu1—O5	1.944 (2)	C1—C3	1.556 (5)
Cu1—N1	2.054 (3)	C2—H2A	0.9900
Cu1—Cl1	2.2812 (10)	C2—H2B	0.9900
Cu1—O3	2.361 (3)	C3—H3A	0.9900
Cu1—O4	2.436 (2)	C3—H3B	0.9900
O1—C2	1.438 (4)	C4—H4A	0.9900
O1—H1	0.833 (19)	C4—H4B	0.9900
O2—C3	1.412 (4)	C5—C6	1.516 (4)
O2—H2	0.856 (19)	C5—H5A	0.9900
O3—C4	1.425 (4)	C5—H5B	0.9900
O3—H3	0.818 (19)	C6—H6A	0.9900
O4—C6	1.437 (4)	C6—H6B	0.9900
O4—H4	0.819 (18)	C7—C8	1.534 (5)
O5—C8	1.420 (4)	C7—H7A	0.9900
N1—C7	1.489 (4)	C7—H7B	0.9900
N1—C5	1.491 (4)	C8—H8A	0.9900
N1—C1	1.509 (4)	C8—H8B	0.9900
C1—C2	1.522 (5)
O2—Cu1—O5	166.42 (10)	C1—C2—H2A	108.9
O2—Cu1—N1	82.17 (10)	O1—C2—H2B	108.9
O5—Cu1—N1	85.29 (10)	C1—C2—H2B	108.9
O2—Cu1—Cl1	98.45 (7)	H2A—C2—H2B	107.7
O5—Cu1—Cl1	94.41 (7)	O2—C3—C1	111.0 (3)
N1—Cu1—Cl1	176.13 (8)	O2—C3—H3A	109.4
O2—Cu1—O3	79.29 (9)	C1—C3—H3A	109.4
O5—Cu1—O3	93.57 (9)	O2—C3—H3B	109.4
N1—Cu1—O3	80.70 (10)	C1—C3—H3B	109.4
Cl1—Cu1—O3	103.18 (7)	H3A—C3—H3B	108.0
O2—Cu1—O4	93.48 (9)	O3—C4—C1	108.3 (3)
O5—Cu1—O4	89.25 (9)	O3—C4—H4A	110.0
N1—Cu1—O4	79.10 (10)	C1—C4—H4A	110.0
Cl1—Cu1—O4	97.04 (6)	O3—C4—H4B	110.0
O3—Cu1—O4	159.29 (9)	C1—C4—H4B	110.0
C2—O1—H1	110 (3)	H4A—C4—H4B	108.4
C3—O2—Cu1	112.91 (19)	N1—C5—C6	114.1 (3)
C3—O2—H2	106 (3)	N1—C5—H5A	108.7
Cu1—O2—H2	134 (3)	C6—C5—H5A	108.7
C4—O3—Cu1	105.16 (18)	N1—C5—H5B	108.7
C4—O3—H3	106 (3)	C6—C5—H5B	108.7
Cu1—O3—H3	118 (3)	H5A—C5—H5B	107.6
C6—O4—Cu1	105.88 (18)	O4—C6—C5	109.3 (3)
C6—O4—H4	105 (3)	O4—C6—H6A	109.8
Cu1—O4—H4	113 (3)	C5—C6—H6A	109.8
C8—O5—Cu1	112.74 (19)	O4—C6—H6B	109.8
C7—N1—C5	111.8 (3)	C5—C6—H6B	109.8
C7—N1—C1	116.3 (3)	H6A—C6—H6B	108.3
C5—N1—C1	111.1 (2)	N1—C7—C8	109.9 (3)
C7—N1—Cu1	107.9 (2)	N1—C7—H7A	109.7
C5—N1—Cu1	109.0 (2)	C8—C7—H7A	109.7
C1—N1—Cu1	99.8 (2)	N1—C7—H7B	109.7
N1—C1—C2	115.2 (3)	C8—C7—H7B	109.7
N1—C1—C4	110.3 (3)	H7A—C7—H7B	108.2
C2—C1—C4	109.3 (3)	O5—C8—C7	110.1 (3)
N1—C1—C3	106.3 (3)	O5—C8—H8A	109.6
C2—C1—C3	107.7 (3)	C7—C8—H8A	109.6
C4—C1—C3	107.8 (3)	O5—C8—H8B	109.6
O1—C2—C1	113.2 (3)	C7—C8—H8B	109.6
O1—C2—H2A	108.9	H8A—C8—H8B	108.1
C7—N1—C1—C2	72.7 (4)	C4—C1—C3—O2	−82.8 (3)
C5—N1—C1—C2	−56.7 (4)	Cu1—O3—C4—C1	22.4 (3)
Cu1—N1—C1—C2	−171.5 (2)	N1—C1—C4—O3	−60.1 (3)
C7—N1—C1—C4	−51.5 (4)	C2—C1—C4—O3	172.3 (3)
C5—N1—C1—C4	179.1 (3)	C3—C1—C4—O3	55.5 (3)
Cu1—N1—C1—C4	64.2 (3)	C7—N1—C5—C6	69.7 (4)
C7—N1—C1—C3	−168.1 (3)	C1—N1—C5—C6	−158.5 (3)
C5—N1—C1—C3	62.5 (3)	Cu1—N1—C5—C6	−49.5 (3)
Cu1—N1—C1—C3	−52.3 (3)	Cu1—O4—C6—C5	−28.5 (3)
N1—C1—C2—O1	−72.4 (3)	N1—C5—C6—O4	53.5 (4)
C4—C1—C2—O1	52.4 (4)	C5—N1—C7—C8	−91.3 (3)
C3—C1—C2—O1	169.2 (2)	C1—N1—C7—C8	139.7 (3)
Cu1—O2—C3—C1	2.2 (3)	Cu1—N1—C7—C8	28.6 (3)
N1—C1—C3—O2	35.5 (3)	Cu1—O5—C8—C7	34.4 (3)
C2—C1—C3—O2	159.4 (3)	N1—C7—C8—O5	−41.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1^i	0.83 (2)	2.24 (2)	3.068 (2)	174 (4)
O2—H2···O5^ii	0.86 (2)	1.55 (2)	2.408 (3)	178 (4)
O3—H3···O4^iii	0.82 (2)	2.00 (2)	2.758 (3)	154 (4)
O4—H4···O1^iv	0.82 (2)	1.85 (2)	2.663 (3)	171 (4)
C4—H4B···Cl1^v	0.99	2.97	3.906 (3)	157
C5—H5A···Cl1^i	0.99	2.97	3.887 (4)	155
C7—H7B···Cl1^i	0.99	2.85	3.727 (3)	148
C8—H8B···O1^vi	0.99	2.65	3.577 (4)	157

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