Crystal structure, Hirshfeld surface analysis and corrosion inhibition study of 3,6-bis­(pyridin-2-yl)-4-{[(3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetra­methyl­tetra­hydro-5H-bis­[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)meth­oxy]meth­yl}pyridazine monohydrate

Filali, M.; Elmsellem, H.; Hökelek, T.; El-Ghayoury, A.; Stetsiuk, O.; El Hadrami, E.M.; Ben-Tama, A.

doi:10.1107/S2056989019009848

Crystal structure, Hirshfeld surface analysis and corrosion inhibition study of 3,6-bis(pyridin-2-yl)-4-{[(3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-5H-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)methoxy]methyl}pyridazine monohydrate

M. Filali, H. Elmsellem, T. Hökelek, A. El-Ghayoury, O. Stetsiuk, E. M. El Hadrami and A. Ben-Tama

The title compound is built up by two dioxolo, two pyridine, one pyridazine and one pyran rings. The two dioxolo rings are in envelope conformations, while the pyran ring is in twisted-boat conformation. The pyradizine ring is oriented at dihedral angles of 9.23 (6) and 12.98 (9)° with respect to the pyridine rings, while the dihedral angle between the two pyridine rings is 13.45 (10)°. In the crystal, C—H_dioxolo

O_dioxolo, O—H_water

O_pyran, O—H_water

O_{methoxymethyl} and O—H_water

N_pyridazine hydrogen bonds link the molecules into a supramolecular structure. A weak C—H_{methoxymethyl}

π interaction is also observed.

Keywords: crystal structure; pyridazine; dioxolo; Hirshfeld surface; electrochemical measurements.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019009848/lh5910sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019009848/lh5910Isup2.hkl Contains datablock I
	Chemdraw file https://doi.org/10.1107/S2056989019009848/lh5910Isup3.cdx Supplementary material

CCDC reference: 1939591

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Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R factor = 0.048
wR factor = 0.121
Data-to-parameter ratio = 12.1

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No syntax errors found



Datablock: I


Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00509 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         66 %

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3             106.7 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O4             107.6 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O5             109.7 Degree
PLAT791_ALERT_4_G Model has Chirality at C1          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C2          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C6          (Chiral SPGR)          S Verify
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters         13 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         54 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


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              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2015); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2015).

3,6-Bis(pyridin-2-yl)-4-{[(3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-5H-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-5-yl)methoxy]methyl}pyridazine monohydrate top

Crystal data top

C₂₇H₃₀N₄O₆·H₂O	D_x = 1.354 Mg m⁻³
M_r = 524.56	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2843 reflections
a = 8.8417 (3) Å	θ = 3.3–72.3°
b = 11.3252 (3) Å	µ = 0.82 mm⁻¹
c = 25.7003 (8) Å	T = 150 K
V = 2573.47 (14) Å³	Plate, colourless
Z = 4	0.47 × 0.15 × 0.10 mm
F(000) = 1112

Data collection top

Rigaku Oxford Diffraction SuperNova, single source at offset, AtlasS2 diffractometer	4277 independent reflections
Radiation source: SuperNova(Cu) micro-focus sealed X-ray Source	3853 reflections with I > 2σ(I)
Detector resolution: 5.1990 pixels mm^-1	R_int = 0.037
ω scans	θ_max = 72.4°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis PRO (Rigaku OD, 2015)	h = −9→10
T_min = 0.656, T_max = 1.000	k = −13→5
6128 measured reflections	l = −31→29

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0538P)² + 0.4885P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.121	(Δ/σ)_max < 0.001
S = 1.10	Δρ_max = 0.27 e Å⁻³
4277 reflections	Δρ_min = −0.36 e Å⁻³
353 parameters	Absolute structure: Flack x determined using 1226 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: −0.01 (16)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.3541 (3)	0.1622 (2)	0.41689 (9)	0.0282 (5)
O2	0.3948 (3)	0.34989 (19)	0.45130 (10)	0.0314 (5)
O3	0.6462 (3)	0.30998 (18)	0.44345 (9)	0.0275 (5)
O4	0.5889 (3)	0.00085 (19)	0.47272 (8)	0.0298 (5)
O5	0.5504 (4)	−0.04337 (19)	0.38768 (10)	0.0397 (7)
O6	0.2874 (3)	0.20336 (19)	0.30710 (9)	0.0341 (6)
N1	0.0414 (3)	0.4001 (2)	0.16743 (11)	0.0279 (6)
N2	0.0957 (3)	0.5016 (2)	0.18697 (10)	0.0280 (6)
N3	0.3589 (4)	0.6013 (3)	0.28330 (11)	0.0324 (6)
N4	0.0746 (4)	0.0864 (2)	0.17094 (12)	0.0358 (7)
C1	0.4587 (4)	0.1547 (3)	0.37413 (12)	0.0258 (7)
H1	0.495093	0.234348	0.366098	0.031*
C2	0.4106 (4)	0.2260 (3)	0.45945 (13)	0.0277 (7)
H2	0.355033	0.203400	0.490891	0.033*
C3	0.5408 (4)	0.4049 (3)	0.44788 (14)	0.0310 (7)
C4	0.5790 (4)	0.2100 (3)	0.46886 (12)	0.0246 (6)
H4	0.600843	0.212023	0.506234	0.030*
C5	0.6463 (4)	0.0999 (3)	0.44448 (12)	0.0254 (6)
H5	0.756973	0.102135	0.446060	0.031*
C6	0.5926 (4)	0.0790 (3)	0.38885 (12)	0.0272 (7)
H6	0.676097	0.092996	0.364527	0.033*
C7	0.5754 (4)	−0.0947 (3)	0.43729 (13)	0.0310 (7)
C8	0.4413 (5)	−0.1669 (4)	0.4525 (2)	0.0550 (12)
H8A	0.453499	−0.194150	0.487614	0.082*
H8B	0.432577	−0.233440	0.429569	0.082*
H8C	0.351559	−0.119463	0.450095	0.082*
C9	0.7193 (5)	−0.1667 (3)	0.43584 (15)	0.0394 (9)
H9A	0.802843	−0.116353	0.427016	0.059*
H9B	0.709878	−0.227881	0.410208	0.059*
H9C	0.736583	−0.201467	0.469376	0.059*
C10	0.5503 (5)	0.4786 (3)	0.39910 (15)	0.0427 (9)
H10A	0.650263	0.510885	0.395892	0.064*
H10B	0.478045	0.541722	0.400967	0.064*
H10C	0.528653	0.430067	0.369395	0.064*
C11	0.5698 (5)	0.4759 (3)	0.49680 (16)	0.0442 (9)
H11A	0.569729	0.424125	0.526380	0.066*
H11B	0.491803	0.534147	0.500856	0.066*
H11C	0.666221	0.514400	0.494189	0.066*
C12	0.3729 (4)	0.1086 (3)	0.32779 (13)	0.0286 (7)
H12A	0.442659	0.078782	0.301797	0.034*
H12B	0.306342	0.044768	0.338237	0.034*
C13	0.2122 (4)	0.1736 (3)	0.26014 (13)	0.0275 (7)
H13A	0.122273	0.127514	0.267550	0.033*
H13B	0.278292	0.127130	0.238042	0.033*
C14	0.1697 (4)	0.2873 (3)	0.23325 (12)	0.0253 (6)
C15	0.0791 (4)	0.2958 (3)	0.18820 (12)	0.0247 (6)
C16	0.1872 (4)	0.4980 (3)	0.22846 (12)	0.0247 (6)
C17	0.2238 (4)	0.3919 (3)	0.25319 (12)	0.0263 (6)
H17	0.284224	0.391984	0.282822	0.032*
C18	0.2537 (4)	0.6114 (3)	0.24658 (12)	0.0265 (7)
C19	0.2107 (4)	0.7197 (3)	0.22546 (14)	0.0315 (7)
H19	0.135761	0.723846	0.200145	0.038*
C20	0.2823 (5)	0.8210 (3)	0.24304 (15)	0.0380 (8)
H20	0.256630	0.894499	0.229490	0.046*
C21	0.3920 (4)	0.8114 (3)	0.28088 (15)	0.0376 (9)
H21	0.441630	0.877961	0.293426	0.045*
C22	0.4265 (5)	0.7001 (3)	0.29975 (14)	0.0349 (8)
H22	0.500690	0.693707	0.325247	0.042*
C23	0.0175 (4)	0.1927 (3)	0.15887 (12)	0.0253 (7)
C24	−0.0897 (4)	0.2085 (3)	0.12003 (13)	0.0325 (7)
H24	−0.126828	0.283313	0.112401	0.039*
C25	−0.1402 (5)	0.1107 (3)	0.09294 (14)	0.0378 (8)
H25	−0.211674	0.119110	0.066653	0.045*
C26	−0.0836 (5)	0.0004 (3)	0.10520 (14)	0.0375 (8)
H26	−0.116014	−0.066836	0.087656	0.045*
C27	0.0224 (5)	−0.0065 (3)	0.14423 (15)	0.0414 (9)
H27	0.060342	−0.080694	0.152640	0.050*
O7	0.0146 (4)	0.1893 (3)	0.38725 (14)	0.0542 (8)
H7A	−0.011 (7)	0.141 (5)	0.3642 (19)	0.081*
H7B	0.111 (3)	0.189 (6)	0.386 (2)	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0250 (11)	0.0272 (10)	0.0325 (11)	−0.0023 (10)	−0.0016 (10)	−0.0023 (9)
O2	0.0294 (12)	0.0210 (10)	0.0438 (13)	0.0057 (9)	−0.0026 (11)	−0.0024 (9)
O3	0.0280 (11)	0.0181 (10)	0.0364 (12)	0.0007 (9)	0.0010 (10)	0.0006 (9)
O4	0.0419 (14)	0.0190 (9)	0.0286 (11)	−0.0011 (10)	−0.0005 (11)	0.0020 (8)
O5	0.0627 (18)	0.0179 (10)	0.0385 (13)	0.0041 (11)	−0.0184 (14)	−0.0038 (9)
O6	0.0499 (15)	0.0190 (9)	0.0333 (12)	0.0033 (11)	−0.0182 (12)	−0.0023 (9)
N1	0.0324 (15)	0.0203 (12)	0.0310 (13)	−0.0004 (11)	−0.0037 (13)	−0.0002 (10)
N2	0.0339 (16)	0.0192 (11)	0.0310 (13)	0.0005 (11)	0.0006 (13)	−0.0010 (10)
N3	0.0367 (16)	0.0252 (13)	0.0352 (14)	−0.0026 (12)	−0.0011 (13)	−0.0045 (11)
N4	0.0485 (18)	0.0212 (12)	0.0377 (15)	0.0021 (13)	−0.0154 (15)	−0.0018 (11)
C1	0.0331 (17)	0.0180 (12)	0.0265 (15)	−0.0010 (13)	−0.0025 (14)	0.0020 (11)
C2	0.0333 (17)	0.0201 (13)	0.0298 (15)	0.0016 (13)	0.0036 (15)	−0.0006 (12)
C3	0.0324 (18)	0.0192 (13)	0.0415 (18)	0.0039 (14)	−0.0005 (16)	−0.0011 (13)
C4	0.0299 (16)	0.0179 (12)	0.0260 (14)	−0.0003 (13)	−0.0018 (14)	−0.0005 (11)
C5	0.0295 (16)	0.0188 (13)	0.0280 (15)	0.0026 (13)	0.0008 (14)	0.0019 (12)
C6	0.0333 (18)	0.0209 (13)	0.0274 (15)	0.0010 (13)	−0.0001 (14)	−0.0005 (12)
C7	0.0382 (19)	0.0194 (13)	0.0354 (17)	0.0006 (14)	−0.0015 (16)	−0.0004 (12)
C8	0.047 (2)	0.0365 (19)	0.081 (3)	−0.012 (2)	0.017 (2)	−0.020 (2)
C9	0.044 (2)	0.0321 (17)	0.042 (2)	0.0111 (17)	−0.0034 (18)	0.0023 (15)
C10	0.051 (2)	0.0257 (16)	0.051 (2)	0.0042 (16)	0.002 (2)	0.0079 (15)
C11	0.051 (2)	0.0317 (17)	0.050 (2)	0.0028 (18)	−0.007 (2)	−0.0124 (16)
C12	0.0360 (18)	0.0191 (12)	0.0307 (15)	0.0030 (13)	−0.0085 (15)	0.0024 (12)
C13	0.0331 (17)	0.0174 (13)	0.0319 (16)	−0.0019 (13)	−0.0062 (14)	0.0005 (12)
C14	0.0270 (16)	0.0224 (14)	0.0265 (15)	0.0009 (13)	−0.0004 (13)	0.0014 (12)
C15	0.0269 (16)	0.0194 (13)	0.0277 (14)	0.0000 (13)	−0.0005 (14)	−0.0013 (12)
C16	0.0265 (16)	0.0212 (13)	0.0265 (14)	−0.0003 (12)	0.0026 (13)	−0.0020 (11)
C17	0.0297 (16)	0.0220 (13)	0.0272 (15)	0.0006 (13)	−0.0020 (14)	−0.0011 (12)
C18	0.0285 (16)	0.0217 (14)	0.0293 (15)	−0.0001 (12)	0.0037 (14)	−0.0029 (12)
C19	0.0348 (18)	0.0208 (14)	0.0389 (17)	−0.0005 (15)	−0.0010 (16)	−0.0021 (13)
C20	0.043 (2)	0.0209 (15)	0.050 (2)	−0.0014 (15)	0.0039 (18)	−0.0021 (14)
C21	0.039 (2)	0.0247 (15)	0.049 (2)	−0.0039 (14)	0.0037 (18)	−0.0108 (14)
C22	0.0395 (19)	0.0276 (15)	0.0375 (17)	−0.0033 (16)	−0.0026 (16)	−0.0073 (14)
C23	0.0262 (16)	0.0238 (14)	0.0259 (14)	−0.0037 (12)	0.0008 (13)	0.0003 (12)
C24	0.0327 (18)	0.0295 (15)	0.0353 (16)	0.0029 (15)	−0.0075 (15)	−0.0002 (14)
C25	0.0383 (19)	0.0395 (18)	0.0358 (18)	−0.0010 (17)	−0.0148 (17)	−0.0026 (15)
C26	0.049 (2)	0.0271 (15)	0.0366 (17)	−0.0079 (17)	−0.0059 (18)	−0.0080 (14)
C27	0.058 (3)	0.0234 (15)	0.0428 (19)	0.0013 (16)	−0.015 (2)	−0.0027 (15)
O7	0.0524 (18)	0.0479 (16)	0.0623 (19)	0.0030 (15)	−0.0015 (16)	−0.0140 (14)

Geometric parameters (Å, º) top

O1—C2	1.403 (4)	C9—H9B	0.9600
O1—C1	1.439 (4)	C9—H9C	0.9600
O2—C2	1.425 (4)	C10—H10A	0.9600
O2—C3	1.437 (4)	C10—H10B	0.9600
O3—C3	1.428 (4)	C10—H10C	0.9600
O3—C4	1.436 (4)	C11—H11A	0.9600
O4—C7	1.419 (4)	C11—H11B	0.9600
O4—C5	1.430 (4)	C11—H11C	0.9600
O5—C7	1.418 (4)	C12—H12A	0.9700
O5—C6	1.436 (4)	C12—H12B	0.9700
O6—C12	1.416 (4)	C13—C14	1.509 (4)
O6—C13	1.418 (4)	C13—H13A	0.9700
N1—C15	1.339 (4)	C13—H13B	0.9700
N1—N2	1.343 (4)	C14—C17	1.377 (4)
N2—C16	1.339 (4)	C14—C15	1.411 (4)
N3—C18	1.330 (5)	C15—C23	1.493 (4)
N3—C22	1.337 (5)	C16—C17	1.397 (4)
N4—C27	1.339 (5)	C16—C18	1.488 (4)
N4—C23	1.341 (4)	C17—H17	0.9300
C1—C12	1.506 (5)	C18—C19	1.394 (5)
C1—C6	1.510 (5)	C19—C20	1.386 (5)
C1—H1	0.9800	C19—H19	0.9300
C2—C4	1.519 (5)	C20—C21	1.378 (6)
C2—H2	0.9800	C20—H20	0.9300
C3—C10	1.508 (5)	C21—C22	1.385 (5)
C3—C11	1.514 (5)	C21—H21	0.9300
C4—C5	1.517 (4)	C22—H22	0.9300
C4—H4	0.9800	C23—C24	1.388 (5)
C5—C6	1.525 (4)	C24—C25	1.382 (5)
C5—H5	0.9800	C24—H24	0.9300
C6—H6	0.9800	C25—C26	1.383 (5)
C7—C8	1.492 (6)	C25—H25	0.9300
C7—C9	1.512 (5)	C26—C27	1.375 (6)
C8—H8A	0.9600	C26—H26	0.9300
C8—H8B	0.9600	C27—H27	0.9300
C8—H8C	0.9600	O7—H7A	0.84 (2)
C9—H9A	0.9600	O7—H7B	0.86 (2)

O1···O3	3.153 (2)	C2···C4ⁱⁱ	3.538 (4)
O1···O4	3.115 (3)	C2···H4ⁱⁱ	2.96
O1···O5	2.999 (3)	C3···H1	2.88
O1···O6	2.920 (3)	C4···H11A	2.84
O3···O1	3.153 (2)	C4···H2ⁱⁱⁱ	2.83
O3···C1	3.002 (3)	C4···H1	2.76
O7···O1	3.112 (3)	C5···H9A	2.85
O7···O6	3.176 (3)	C10···H1	2.93
O7···N2ⁱ	3.020 (3)	H1···H10C	2.24
O2···H1	2.70	H2···H4ⁱⁱ	2.44
O2···H4ⁱⁱ	2.90	H4···H11A	2.47
O3···H1	2.54	H5···H9A	2.56
O3···H2ⁱⁱⁱ	2.51	H7A···H19ⁱ	2.20
O5···H12B	2.70	H7A···N1ⁱ	2.84 (3)
O5···H12A	2.77	H7A···N2ⁱ	2.19 (4)
O6···H17	2.23	H7B···O1	2.30 (2)
O7···H19ⁱ	2.64	H7B···O6	2.56 (4)
N4···C13	2.776 (3)	H8A···H9C	2.55
N1···H24	2.44	H8B···H9B	2.50
N2···H19	2.56	H8C···H11Cⁱⁱ	2.48
N3···H17	2.46	H10A···H11C	2.53
N4···H13A	2.56	H10B···H11B	2.57
N4···H13B	2.54	H12A···H13B	2.26
C1···C3	3.485 (3)

C2—O1—C1	113.4 (2)	H10A—C10—H10B	109.5
C2—O2—C3	110.4 (2)	C3—C10—H10C	109.5
C3—O3—C4	106.7 (2)	H10A—C10—H10C	109.5
C7—O4—C5	107.6 (2)	H10B—C10—H10C	109.5
C7—O5—C6	109.6 (2)	C3—C11—H11A	109.5
C12—O6—C13	112.9 (2)	C3—C11—H11B	109.5
C15—N1—N2	121.1 (3)	H11A—C11—H11B	109.5
C16—N2—N1	119.2 (3)	C3—C11—H11C	109.5
C18—N3—C22	117.7 (3)	H11A—C11—H11C	109.5
C27—N4—C23	117.2 (3)	H11B—C11—H11C	109.5
O1—C1—C12	107.5 (3)	O6—C12—C1	107.7 (2)
O1—C1—C6	110.3 (2)	O6—C12—H12A	110.2
C12—C1—C6	113.4 (3)	C1—C12—H12A	110.2
O1—C1—H1	108.5	O6—C12—H12B	110.2
C12—C1—H1	108.5	C1—C12—H12B	110.2
C6—C1—H1	108.5	H12A—C12—H12B	108.5
O1—C2—O2	111.0 (3)	O6—C13—C14	107.7 (2)
O1—C2—C4	114.3 (3)	O6—C13—H13A	110.2
O2—C2—C4	103.7 (3)	C14—C13—H13A	110.2
O1—C2—H2	109.2	O6—C13—H13B	110.2
O2—C2—H2	109.2	C14—C13—H13B	110.2
C4—C2—H2	109.2	H13A—C13—H13B	108.5
O3—C3—O2	105.4 (2)	C17—C14—C15	116.4 (3)
O3—C3—C10	108.3 (3)	C17—C14—C13	118.5 (3)
O2—C3—C10	109.9 (3)	C15—C14—C13	125.1 (3)
O3—C3—C11	110.8 (3)	N1—C15—C14	121.9 (3)
O2—C3—C11	109.4 (3)	N1—C15—C23	113.5 (3)
C10—C3—C11	112.8 (3)	C14—C15—C23	124.6 (3)
O3—C4—C5	107.3 (2)	N2—C16—C17	121.9 (3)
O3—C4—C2	103.9 (2)	N2—C16—C18	117.5 (3)
C5—C4—C2	114.6 (3)	C17—C16—C18	120.5 (3)
O3—C4—H4	110.3	C14—C17—C16	119.3 (3)
C5—C4—H4	110.3	C14—C17—H17	120.3
C2—C4—H4	110.3	C16—C17—H17	120.3
O4—C5—C4	107.2 (2)	N3—C18—C19	122.9 (3)
O4—C5—C6	104.1 (2)	N3—C18—C16	115.1 (3)
C4—C5—C6	113.2 (3)	C19—C18—C16	122.0 (3)
O4—C5—H5	110.7	C20—C19—C18	118.5 (3)
C4—C5—H5	110.7	C20—C19—H19	120.8
C6—C5—H5	110.7	C18—C19—H19	120.8
O5—C6—C1	109.8 (3)	C21—C20—C19	119.1 (3)
O5—C6—C5	104.5 (2)	C21—C20—H20	120.5
C1—C6—C5	113.0 (3)	C19—C20—H20	120.5
O5—C6—H6	109.8	C20—C21—C22	118.3 (3)
C1—C6—H6	109.8	C20—C21—H21	120.8
C5—C6—H6	109.8	C22—C21—H21	120.8
O5—C7—O4	106.1 (2)	N3—C22—C21	123.5 (3)
O5—C7—C8	109.6 (4)	N3—C22—H22	118.2
O4—C7—C8	108.4 (3)	C21—C22—H22	118.2
O5—C7—C9	109.3 (3)	N4—C23—C24	122.6 (3)
O4—C7—C9	110.9 (3)	N4—C23—C15	116.6 (3)
C8—C7—C9	112.3 (3)	C24—C23—C15	120.8 (3)
C7—C8—H8A	109.5	C25—C24—C23	118.7 (3)
C7—C8—H8B	109.5	C25—C24—H24	120.7
H8A—C8—H8B	109.5	C23—C24—H24	120.7
C7—C8—H8C	109.5	C24—C25—C26	119.5 (3)
H8A—C8—H8C	109.5	C24—C25—H25	120.3
H8B—C8—H8C	109.5	C26—C25—H25	120.3
C7—C9—H9A	109.5	C27—C26—C25	117.7 (3)
C7—C9—H9B	109.5	C27—C26—H26	121.2
H9A—C9—H9B	109.5	C25—C26—H26	121.2
C7—C9—H9C	109.5	N4—C27—C26	124.4 (3)
H9A—C9—H9C	109.5	N4—C27—H27	117.8
H9B—C9—H9C	109.5	C26—C27—H27	117.8
C3—C10—H10A	109.5	H7A—O7—H7B	104 (6)
C3—C10—H10B	109.5

C15—N1—N2—C16	−1.1 (5)	O1—C1—C12—O6	77.8 (3)
C2—O1—C1—C12	−167.7 (2)	C6—C1—C12—O6	−160.1 (3)
C2—O1—C1—C6	68.2 (3)	C12—O6—C13—C14	−161.7 (3)
C1—O1—C2—O2	81.1 (3)	O6—C13—C14—C17	8.0 (4)
C1—O1—C2—C4	−35.8 (3)	O6—C13—C14—C15	−172.8 (3)
C3—O2—C2—O1	−115.1 (3)	N2—N1—C15—C14	3.9 (5)
C3—O2—C2—C4	8.1 (3)	N2—N1—C15—C23	−175.6 (3)
C4—O3—C3—O2	−27.7 (3)	C17—C14—C15—N1	−3.3 (5)
C4—O3—C3—C10	−145.2 (3)	C13—C14—C15—N1	177.6 (3)
C4—O3—C3—C11	90.5 (3)	C17—C14—C15—C23	176.1 (3)
C2—O2—C3—O3	11.5 (4)	C13—C14—C15—C23	−3.0 (5)
C2—O2—C3—C10	128.0 (3)	N1—N2—C16—C17	−2.2 (5)
C2—O2—C3—C11	−107.7 (3)	N1—N2—C16—C18	175.7 (3)
C3—O3—C4—C5	154.1 (3)	C15—C14—C17—C16	0.0 (5)
C3—O3—C4—C2	32.4 (3)	C13—C14—C17—C16	179.2 (3)
O1—C2—C4—O3	96.5 (3)	N2—C16—C17—C14	2.7 (5)
O2—C2—C4—O3	−24.4 (3)	C18—C16—C17—C14	−175.2 (3)
O1—C2—C4—C5	−20.2 (4)	C22—N3—C18—C19	−0.8 (5)
O2—C2—C4—C5	−141.2 (3)	C22—N3—C18—C16	177.7 (3)
C7—O4—C5—C4	147.7 (3)	N2—C16—C18—N3	−171.4 (3)
C7—O4—C5—C6	27.5 (3)	C17—C16—C18—N3	6.5 (4)
O3—C4—C5—O4	175.2 (2)	N2—C16—C18—C19	7.1 (5)
C2—C4—C5—O4	−70.0 (3)	C17—C16—C18—C19	−174.9 (3)
O3—C4—C5—C6	−70.5 (3)	N3—C18—C19—C20	0.9 (5)
C2—C4—C5—C6	44.2 (4)	C16—C18—C19—C20	−177.5 (3)
C7—O5—C6—C1	−121.7 (3)	C18—C19—C20—C21	−0.5 (5)
C7—O5—C6—C5	−0.3 (4)	C19—C20—C21—C22	0.1 (5)
O1—C1—C6—O5	76.1 (3)	C18—N3—C22—C21	0.4 (5)
C12—C1—C6—O5	−44.5 (4)	C20—C21—C22—N3	−0.1 (6)
O1—C1—C6—C5	−40.1 (3)	C27—N4—C23—C24	−0.9 (5)
C12—C1—C6—C5	−160.7 (3)	C27—N4—C23—C15	−178.8 (3)
O4—C5—C6—O5	−16.4 (3)	N1—C15—C23—N4	167.1 (3)
C4—C5—C6—O5	−132.5 (3)	C14—C15—C23—N4	−12.4 (5)
O4—C5—C6—C1	102.9 (3)	N1—C15—C23—C24	−10.8 (4)
C4—C5—C6—C1	−13.2 (4)	C14—C15—C23—C24	169.7 (3)
C6—O5—C7—O4	17.2 (4)	N4—C23—C24—C25	0.4 (5)
C6—O5—C7—C8	134.1 (3)	C15—C23—C24—C25	178.2 (3)
C6—O5—C7—C9	−102.4 (3)	C23—C24—C25—C26	0.2 (6)
C5—O4—C7—O5	−28.3 (4)	C24—C25—C26—C27	−0.3 (6)
C5—O4—C7—C8	−146.0 (3)	C23—N4—C27—C26	0.8 (6)
C5—O4—C7—C9	90.3 (3)	C25—C26—C27—N4	−0.3 (7)
C13—O6—C12—C1	174.4 (3)

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N3/C18–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···N2ⁱ	0.84 (2)	2.18 (3)	3.019 (4)	172 (6)
O7—H7B···O1	0.86 (2)	2.30 (3)	3.112 (4)	157 (6)
O7—H7B···O6	0.86 (2)	2.57 (5)	3.176 (5)	129 (5)
C2—H2···O3ⁱⁱ	0.98	2.51	3.444 (4)	160
C12—H12A···Cg^iv	0.97	3.07	3.761 (3)	130

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

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Crystal structure, Hirshfeld surface analysis and corrosion inhibition study of 3,6-bis­(pyridin-2-yl)-4-{[(3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetra­methyl­tetra­hydro-5H-bis­[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)meth­oxy]meth­yl}pyridazine monohydrate

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Crystal structure, Hirshfeld surface analysis and corrosion inhibition study of 3,6-bis(pyridin-2-yl)-4-{[(3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-5H-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)methoxy]methyl}pyridazine monohydrate