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The reaction of 3,5-diamino­benzoic acid, 1,10-phenanthroline, NaN3 and ZnII in basic aqueous solution gave rise to the title compound, [Zn(C7H7N2O2)(N3)(C12H8N2)(H2O)2]·H2O. The ZnII atom is six-coordinate with a distorted octa­hedral geometry. The two aqua ligands are in cis positions and the 3,5-diamino­benzoate ligand binds to the central Zn atom through one of its amino groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044710/gk2034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044710/gk2034Isup2.hkl
Contains datablock I

CCDC reference: 629591

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.025
  • wR factor = 0.067
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N3 - N4 .. 7.20 su
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - N5 .. 6.57 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N3 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1WB .. N4 .. 2.66 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Diaquaazido(3,5-diaminobenzoato-κN)(1,10-phenanthroline-κ2N,N')zinc(II) monohydrate top
Crystal data top
[Zn(C7H7N2O2)(N3)(C12H8N2)(H2O)2]·H2OZ = 2
Mr = 492.80F(000) = 508
Triclinic, P1Dx = 1.584 Mg m3
a = 7.8039 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1720 (2) ÅCell parameters from 5973 reflections
c = 13.4728 (2) Åθ = 2.7–27.5°
α = 81.959 (1)°µ = 1.24 mm1
β = 85.029 (1)°T = 293 K
γ = 77.786 (1)°Block, colourless
V = 1033.20 (3) Å30.30 × 0.20 × 0.16 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3629 independent reflections
Radiation source: fine-focus sealed tube3307 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.708, Tmax = 0.827k = 1212
10775 measured reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.035P)2 + 0.2809P]
where P = (Fo2 + 2Fc2)/3
3629 reflections(Δ/σ)max = 0.002
318 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Zn10.96446 (3)0.18279 (2)0.776106 (16)0.02717 (9)
C11.2251 (3)0.0404 (2)0.66870 (19)0.0461 (6)
H11.24180.08610.73300.055*
C21.3202 (3)0.0982 (3)0.5881 (2)0.0554 (7)
H21.39880.18060.59900.066*
C31.2979 (3)0.0339 (3)0.4939 (2)0.0530 (6)
H31.35970.07250.43930.064*
C41.1805 (3)0.0917 (2)0.47906 (17)0.0439 (5)
C51.1482 (4)0.1665 (3)0.38247 (18)0.0575 (7)
H51.21050.13390.32590.069*
C61.0291 (4)0.2833 (3)0.37196 (18)0.0579 (7)
H61.00960.32950.30800.070*
C70.9315 (3)0.3384 (2)0.45701 (16)0.0425 (5)
C80.8041 (3)0.4586 (3)0.44954 (18)0.0504 (6)
H80.77680.50600.38690.060*
C90.7209 (3)0.5053 (2)0.53377 (19)0.0488 (6)
H90.63550.58460.52930.059*
C100.7644 (3)0.4333 (2)0.62807 (17)0.0417 (5)
H100.70830.46770.68550.050*
C110.9646 (3)0.2700 (2)0.55399 (14)0.0312 (4)
C121.0892 (3)0.1430 (2)0.56459 (15)0.0318 (4)
C130.7330 (2)0.40946 (17)0.89294 (13)0.0232 (4)
C140.8003 (2)0.52348 (18)0.89672 (13)0.0248 (4)
H140.91740.51530.90980.030*
C150.6911 (2)0.65102 (17)0.88075 (13)0.0243 (4)
C160.5173 (2)0.66250 (18)0.85925 (14)0.0267 (4)
H160.44580.74800.84700.032*
C170.4488 (2)0.54726 (19)0.85587 (14)0.0262 (4)
C180.5580 (2)0.42029 (18)0.87356 (14)0.0263 (4)
H180.51400.34240.87240.032*
C190.7624 (2)0.77614 (18)0.88756 (14)0.0263 (4)
H7A0.245 (3)0.490 (3)0.8389 (19)0.045 (7)*
H7B0.203 (3)0.626 (3)0.8457 (18)0.044 (7)*
H1WA0.712 (3)0.045 (3)0.797 (2)0.044 (8)*
H9WA0.325 (3)0.989 (3)1.0160 (19)0.046 (8)*
H1WB0.647 (4)0.146 (3)0.739 (2)0.052 (8)*
H2WB0.997 (3)0.071 (3)0.8836 (18)0.049 (7)*
H9WB0.420 (4)0.919 (3)0.947 (2)0.055 (8)*
N11.1115 (2)0.07697 (16)0.65801 (13)0.0328 (4)
N20.8824 (2)0.31810 (16)0.63837 (12)0.0313 (4)
N31.1850 (3)0.2732 (2)0.79167 (16)0.0485 (5)
N41.3078 (2)0.25850 (17)0.73405 (15)0.0380 (4)
N51.4276 (2)0.2503 (2)0.67590 (16)0.0524 (5)
N60.8446 (2)0.27711 (14)0.90573 (12)0.0257 (3)
H6A0.78110.22060.94150.031*
H6B0.93170.28180.94390.031*
N70.2765 (2)0.5593 (2)0.83058 (16)0.0391 (4)
O10.7370 (2)0.10497 (18)0.76125 (13)0.0366 (4)
O21.03315 (19)0.00529 (14)0.87731 (11)0.0344 (3)
H2WA1.12740.00420.90030.052*
O30.92316 (18)0.76468 (14)0.89555 (13)0.0420 (4)
O40.65351 (17)0.88859 (12)0.88359 (11)0.0334 (3)
O90.3255 (2)0.93507 (16)0.97908 (13)0.0353 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02818 (13)0.02190 (13)0.03021 (13)0.00462 (9)0.00070 (9)0.00128 (9)
C10.0420 (13)0.0378 (12)0.0541 (14)0.0003 (10)0.0016 (11)0.0067 (11)
C20.0450 (14)0.0425 (14)0.0757 (19)0.0013 (11)0.0088 (13)0.0205 (13)
C30.0470 (14)0.0594 (16)0.0583 (16)0.0140 (12)0.0141 (12)0.0320 (13)
C40.0444 (13)0.0534 (14)0.0416 (13)0.0214 (11)0.0053 (10)0.0195 (11)
C50.0720 (18)0.0720 (19)0.0348 (13)0.0241 (15)0.0081 (12)0.0204 (12)
C60.0807 (19)0.0728 (19)0.0261 (12)0.0294 (16)0.0035 (12)0.0046 (11)
C70.0512 (14)0.0473 (13)0.0342 (11)0.0230 (11)0.0071 (10)0.0001 (10)
C80.0610 (16)0.0504 (14)0.0397 (13)0.0175 (12)0.0182 (12)0.0138 (11)
C90.0467 (14)0.0392 (13)0.0553 (15)0.0043 (11)0.0119 (11)0.0109 (11)
C100.0420 (12)0.0355 (12)0.0435 (12)0.0051 (10)0.0011 (10)0.0032 (10)
C110.0341 (11)0.0352 (11)0.0283 (10)0.0177 (9)0.0019 (8)0.0016 (8)
C120.0312 (10)0.0355 (11)0.0337 (11)0.0163 (9)0.0023 (8)0.0092 (9)
C130.0278 (9)0.0184 (9)0.0229 (9)0.0038 (7)0.0013 (7)0.0037 (7)
C140.0227 (9)0.0233 (9)0.0295 (10)0.0070 (7)0.0008 (7)0.0034 (7)
C150.0278 (10)0.0208 (9)0.0250 (9)0.0068 (7)0.0005 (7)0.0039 (7)
C160.0288 (10)0.0202 (9)0.0303 (10)0.0014 (7)0.0031 (8)0.0050 (7)
C170.0241 (9)0.0290 (10)0.0269 (9)0.0056 (8)0.0022 (7)0.0070 (8)
C180.0288 (10)0.0230 (9)0.0304 (10)0.0115 (8)0.0005 (8)0.0066 (8)
C190.0292 (10)0.0208 (9)0.0294 (10)0.0073 (8)0.0027 (8)0.0045 (7)
N10.0314 (9)0.0297 (9)0.0373 (9)0.0060 (7)0.0012 (7)0.0063 (7)
N20.0313 (9)0.0290 (9)0.0321 (9)0.0080 (7)0.0001 (7)0.0028 (7)
N30.0377 (11)0.0508 (12)0.0651 (13)0.0221 (9)0.0095 (10)0.0222 (10)
N40.0314 (10)0.0312 (9)0.0534 (11)0.0084 (7)0.0116 (9)0.0034 (8)
N50.0295 (10)0.0637 (14)0.0586 (13)0.0067 (9)0.0007 (10)0.0041 (10)
N60.0279 (8)0.0171 (7)0.0324 (8)0.0054 (6)0.0037 (7)0.0014 (6)
N70.0269 (9)0.0319 (10)0.0618 (13)0.0048 (9)0.0104 (8)0.0138 (9)
O10.0326 (9)0.0336 (9)0.0436 (9)0.0115 (7)0.0077 (7)0.0065 (7)
O20.0359 (8)0.0242 (7)0.0444 (9)0.0106 (6)0.0126 (6)0.0046 (6)
O30.0293 (8)0.0248 (7)0.0748 (11)0.0086 (6)0.0068 (7)0.0093 (7)
O40.0305 (7)0.0181 (7)0.0513 (9)0.0053 (6)0.0030 (6)0.0059 (6)
O90.0267 (8)0.0367 (8)0.0460 (9)0.0100 (6)0.0018 (7)0.0139 (7)
Geometric parameters (Å, º) top
Zn1—O22.1060 (13)C11—C121.441 (3)
Zn1—O12.1255 (15)C12—N11.348 (3)
Zn1—N32.1539 (18)C13—C141.380 (2)
Zn1—N12.1558 (16)C13—C181.391 (3)
Zn1—N62.1568 (15)C13—N61.437 (2)
Zn1—N22.2061 (16)C14—C151.393 (3)
C1—N11.326 (3)C14—H140.9300
C1—C21.389 (3)C15—C161.389 (3)
C1—H10.9300C15—C191.510 (2)
C2—C31.352 (4)C16—C171.395 (3)
C2—H20.9300C16—H160.9300
C3—C41.406 (4)C17—C181.391 (3)
C3—H30.9300C17—N71.391 (3)
C4—C121.406 (3)C18—H180.9300
C4—C51.426 (4)C19—O31.248 (2)
C5—C61.343 (4)C19—O41.270 (2)
C5—H50.9300N3—N41.177 (3)
C6—C71.434 (4)N4—N51.163 (3)
C6—H60.9300N6—H6A0.9000
C7—C81.401 (3)N6—H6B0.9000
C7—C111.409 (3)N7—H7A0.79 (3)
C8—C91.352 (4)N7—H7B0.83 (3)
C8—H80.9300O1—H1WA0.77 (3)
C9—C101.406 (3)O1—H1WB0.80 (3)
C9—H90.9300O2—H2WB0.87 (3)
C10—N21.326 (3)O2—H2WA0.8200
C10—H100.9300O9—H9WA0.79 (3)
C11—N21.356 (3)O9—H9WB0.82 (3)
O2—Zn1—O183.93 (6)N1—C12—C4122.5 (2)
O2—Zn1—N398.48 (7)N1—C12—C11117.54 (17)
O1—Zn1—N3176.63 (7)C4—C12—C11119.91 (19)
O2—Zn1—N188.90 (6)C14—C13—C18120.90 (16)
O1—Zn1—N192.80 (6)C14—C13—N6120.32 (16)
N3—Zn1—N189.62 (7)C18—C13—N6118.75 (16)
O2—Zn1—N685.89 (6)C13—C14—C15119.34 (17)
O1—Zn1—N691.55 (6)C13—C14—H14120.3
N3—Zn1—N686.28 (7)C15—C14—H14120.3
N1—Zn1—N6172.82 (6)C16—C15—C14119.98 (17)
O2—Zn1—N2160.85 (6)C16—C15—C19120.34 (16)
O1—Zn1—N284.22 (6)C14—C15—C19119.68 (16)
N3—Zn1—N294.06 (7)C15—C16—C17120.74 (17)
N1—Zn1—N276.71 (6)C15—C16—H16119.6
N6—Zn1—N2109.43 (6)C17—C16—H16119.6
N1—C1—C2122.9 (2)C18—C17—N7120.55 (18)
N1—C1—H1118.5C18—C17—C16118.84 (17)
C2—C1—H1118.5N7—C17—C16120.54 (18)
C3—C2—C1119.7 (2)C13—C18—C17120.18 (17)
C3—C2—H2120.2C13—C18—H18119.9
C1—C2—H2120.2C17—C18—H18119.9
C2—C3—C4119.4 (2)O3—C19—O4123.58 (17)
C2—C3—H3120.3O3—C19—C15119.11 (16)
C4—C3—H3120.3O4—C19—C15117.30 (16)
C12—C4—C3117.4 (2)C1—N1—C12118.12 (18)
C12—C4—C5119.4 (2)C1—N1—Zn1126.94 (15)
C3—C4—C5123.3 (2)C12—N1—Zn1114.85 (13)
C6—C5—C4121.0 (2)C10—N2—C11118.04 (18)
C6—C5—H5119.5C10—N2—Zn1129.40 (14)
C4—C5—H5119.5C11—N2—Zn1112.53 (13)
C5—C6—C7121.5 (2)N4—N3—Zn1120.28 (16)
C5—C6—H6119.2N5—N4—N3176.9 (2)
C7—C6—H6119.2C13—N6—Zn1120.01 (11)
C8—C7—C11117.4 (2)C13—N6—H6A107.3
C8—C7—C6123.5 (2)Zn1—N6—H6A107.3
C11—C7—C6119.1 (2)C13—N6—H6B107.3
C9—C8—C7119.7 (2)Zn1—N6—H6B107.3
C9—C8—H8120.1H6A—N6—H6B106.9
C7—C8—H8120.1C17—N7—H7A113.3 (18)
C8—C9—C10119.6 (2)C17—N7—H7B118.1 (17)
C8—C9—H9120.2H7A—N7—H7B116 (2)
C10—C9—H9120.2Zn1—O1—H1WA122.6 (19)
N2—C10—C9122.6 (2)Zn1—O1—H1WB127.0 (19)
N2—C10—H10118.7H1WA—O1—H1WB105 (3)
C9—C10—H10118.7Zn1—O2—H2WB130.2 (17)
N2—C11—C7122.68 (19)Zn1—O2—H2WA109.5
N2—C11—C12118.27 (17)H2WB—O2—H2WA117.5
C7—C11—C12119.05 (19)H9WA—O9—H9WB111 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7A···N3i0.79 (3)2.52 (3)3.260 (3)157 (2)
N7—H7B···O3i0.83 (3)2.43 (3)3.223 (2)160 (2)
O1—H1WA···O4ii0.77 (3)1.95 (3)2.719 (2)178 (3)
O9—H9WA···O4iii0.79 (3)2.00 (3)2.788 (2)174 (3)
O1—H1WB···N5i0.80 (3)2.00 (3)2.799 (3)177 (3)
O1—H1WB···N4i0.80 (3)2.66 (3)3.410 (2)159 (2)
O2—H2WB···O3ii0.87 (3)1.86 (3)2.7334 (19)179 (2)
O9—H9WB···O40.82 (3)1.93 (3)2.742 (2)174 (3)
N6—H6A···O9iv0.902.072.957 (2)170
N6—H6B···O3v0.902.473.291 (2)152
O2—H2WA···O9vi0.821.902.678 (2)157
Symmetry codes: (i) x1, y, z; (ii) x, y1, z; (iii) x+1, y+2, z+2; (iv) x+1, y+1, z+2; (v) x+2, y+1, z+2; (vi) x+1, y1, z.
 

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