2',2'-Dibenzyl­ideneisophthalohydrazide methanol solvate

The title compound, C₂₂H₁₈N₄O₂·CH₃OH, was synthesized by the reaction of benzaldehyde and isophthaloyl hydrazine in methanol. The mol­ecule is non-planar, the dihedral angles between the pairs of aromatic rings being 13.2 (1), 27.0 (1) and 18.4 (1)°. The hydrazide mol­ecules are linked via hydrogen bonds into a chain along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.155
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.778     0.970
            Tmin(prime) and Tmax expected:      0.954     0.970
            RR(prime) =      0.816
            Please check that your absorption correction is appropriate.
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      18.60
            Cell volume su given      =      15.00
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.81
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       6.31 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97/2 (Sheldrick, 1997).

2',2'-Dibenzylideneisophthalohydrazide methanol solvate

Crystal data

C23H22N4O3	F(000) = 1696
Mr = 402.45	Dx = 1.229 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4999 reflections
a = 20.168 (4) Å	θ = 1.8–27.5°
b = 14.737 (3) Å	µ = 0.08 mm^−1
c = 16.357 (3) Å	T = 293 K
β = 116.54 (3)°	Prism, colorless
V = 4349.0 (15) Å^3	0.55 × 0.42 × 0.36 mm
Z = 8

Data collection

Rigaku Weissenberg IP diffractometer	4999 independent reflections
Radiation source: fine-focus sealed tube	3243 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = 0→26
Tmin = 0.778, Tmax = 0.970	k = −19→19
20697 measured reflections	l = −21→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0901P)^2] where P = (Fo^2 + 2Fc^2)/3
4999 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.44217 (9)	−0.05548 (11)	0.33589 (11)	0.0529 (4)
C2	0.43306 (10)	−0.13845 (12)	0.36941 (13)	0.0610 (4)
H2B	0.3877	−0.1683	0.3417	0.073*
C3	0.49100 (12)	−0.17650 (16)	0.44357 (15)	0.0800 (6)
H3B	0.4848	−0.2320	0.4663	0.096*
C4	0.55846 (12)	−0.1323 (2)	0.48442 (16)	0.0899 (7)
H4B	0.5974	−0.1582	0.5349	0.108*
C5	0.56849 (12)	−0.05116 (19)	0.45155 (18)	0.0918 (7)
H5A	0.6141	−0.0219	0.4792	0.110*
C6	0.51095 (11)	−0.01310 (14)	0.37759 (16)	0.0761 (6)
H6A	0.5179	0.0420	0.3548	0.091*
C7	0.38278 (10)	−0.00983 (11)	0.25938 (12)	0.0569 (4)
H7A	0.3946	0.0409	0.2347	0.068*
C8	0.19378 (9)	0.00274 (9)	0.11527 (11)	0.0493 (4)
C9	0.14804 (9)	0.07022 (9)	0.04362 (11)	0.0475 (3)
C10	0.17282 (8)	0.15852 (9)	0.04371 (10)	0.0440 (3)
H10A	0.2169	0.1778	0.0918	0.053*
C11	0.13266 (8)	0.21787 (9)	−0.02682 (10)	0.0445 (3)
C12	0.06619 (10)	0.18904 (12)	−0.09731 (13)	0.0649 (5)
H12A	0.0394	0.2276	−0.1460	0.078*
C13	0.03989 (11)	0.10285 (13)	−0.09500 (15)	0.0794 (6)
H13A	−0.0058	0.0847	−0.1409	0.095*
C14	0.08071 (10)	0.04353 (12)	−0.02534 (14)	0.0652 (5)
H14A	0.0628	−0.0145	−0.0249	0.078*
C15	0.16019 (8)	0.31091 (10)	−0.03247 (11)	0.0458 (3)
C16	0.28167 (10)	0.46415 (10)	0.12448 (12)	0.0552 (4)
H16A	0.2934	0.4281	0.1758	0.066*
C17	0.31690 (9)	0.55314 (11)	0.13602 (12)	0.0542 (4)
C18	0.37162 (12)	0.57653 (13)	0.22157 (15)	0.0721 (5)
H18A	0.3843	0.5366	0.2703	0.087*
C19	0.40756 (13)	0.65904 (16)	0.23486 (18)	0.0919 (7)
H19A	0.4445	0.6743	0.2924	0.110*
C20	0.38907 (14)	0.71824 (15)	0.16387 (19)	0.0931 (7)
H20A	0.4130	0.7740	0.1733	0.112*
C21	0.33506 (13)	0.69571 (13)	0.07835 (17)	0.0804 (6)
H21A	0.3232	0.7358	0.0299	0.097*
C22	0.29830 (11)	0.61377 (11)	0.06400 (14)	0.0643 (5)
H22A	0.2612	0.5992	0.0063	0.077*
C23	0.30528 (19)	0.23499 (17)	0.29017 (17)	0.1246 (12)
H23A	0.3082	0.1835	0.2560	0.187*
H23B	0.2932	0.2150	0.3378	0.187*
H23C	0.3522	0.2658	0.3167	0.187*
N1	0.31563 (7)	−0.03554 (8)	0.22437 (9)	0.0512 (3)
N2	0.26757 (7)	0.01782 (8)	0.15277 (9)	0.0535 (3)
H2A	0.2847	0.0608	0.1321	0.064*
N3	0.20711 (7)	0.34913 (8)	0.04749 (9)	0.0480 (3)
H3A	0.2192	0.3210	0.0982	0.052 (5)*
N4	0.23556 (7)	0.43439 (8)	0.04670 (9)	0.0481 (3)
O1	0.16633 (7)	−0.06044 (7)	0.13789 (9)	0.0647 (3)
O2	0.14186 (7)	0.34821 (8)	−0.10677 (8)	0.0594 (3)
O3	0.25191 (8)	0.29256 (8)	0.23362 (9)	0.0731 (4)
H3C	0.2470	0.3409	0.2625	0.113 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0530 (9)	0.0534 (8)	0.0523 (9)	−0.0016 (7)	0.0237 (8)	0.0004 (7)
C2	0.0547 (9)	0.0610 (10)	0.0635 (11)	0.0017 (8)	0.0233 (9)	0.0126 (9)
C3	0.0744 (13)	0.0886 (13)	0.0765 (14)	0.0166 (11)	0.0332 (12)	0.0312 (12)
C4	0.0634 (12)	0.125 (2)	0.0619 (13)	0.0257 (13)	0.0104 (10)	0.0114 (13)
C5	0.0596 (12)	0.1021 (17)	0.0881 (17)	−0.0089 (12)	0.0102 (12)	−0.0106 (14)
C6	0.0641 (11)	0.0710 (12)	0.0842 (14)	−0.0108 (10)	0.0250 (11)	−0.0024 (11)
C7	0.0638 (10)	0.0463 (8)	0.0614 (11)	−0.0015 (7)	0.0288 (9)	0.0101 (7)
C8	0.0616 (9)	0.0400 (7)	0.0478 (9)	−0.0037 (7)	0.0257 (8)	0.0010 (6)
C9	0.0517 (8)	0.0422 (7)	0.0493 (9)	−0.0009 (6)	0.0233 (7)	0.0025 (6)
C10	0.0448 (7)	0.0420 (7)	0.0433 (8)	−0.0001 (6)	0.0178 (7)	0.0010 (6)
C11	0.0441 (7)	0.0423 (7)	0.0448 (8)	0.0012 (6)	0.0178 (7)	0.0019 (6)
C12	0.0574 (10)	0.0579 (10)	0.0588 (11)	−0.0001 (8)	0.0074 (9)	0.0094 (8)
C13	0.0592 (11)	0.0637 (11)	0.0800 (14)	−0.0137 (9)	−0.0007 (10)	0.0032 (10)
C14	0.0576 (10)	0.0504 (9)	0.0744 (12)	−0.0112 (8)	0.0178 (9)	0.0026 (9)
C15	0.0454 (8)	0.0425 (7)	0.0474 (9)	0.0069 (6)	0.0188 (7)	0.0073 (7)
C16	0.0644 (10)	0.0446 (8)	0.0550 (10)	0.0001 (7)	0.0253 (9)	0.0053 (7)
C17	0.0594 (9)	0.0438 (8)	0.0621 (10)	−0.0010 (7)	0.0297 (9)	−0.0033 (7)
C18	0.0752 (12)	0.0652 (11)	0.0675 (12)	−0.0098 (9)	0.0243 (10)	−0.0047 (10)
C19	0.0905 (16)	0.0802 (14)	0.0882 (17)	−0.0301 (12)	0.0250 (14)	−0.0150 (13)
C20	0.1007 (17)	0.0598 (11)	0.113 (2)	−0.0301 (12)	0.0423 (16)	−0.0086 (13)
C21	0.0999 (15)	0.0519 (10)	0.0894 (16)	−0.0105 (10)	0.0422 (14)	0.0062 (10)
C22	0.0750 (11)	0.0461 (8)	0.0687 (12)	−0.0017 (8)	0.0293 (10)	0.0003 (8)
C23	0.168 (3)	0.0819 (16)	0.0697 (16)	0.0374 (17)	0.0041 (17)	−0.0013 (13)
N1	0.0580 (8)	0.0439 (6)	0.0490 (8)	0.0024 (6)	0.0214 (6)	0.0084 (6)
N2	0.0578 (8)	0.0446 (6)	0.0557 (8)	0.0014 (6)	0.0233 (7)	0.0156 (6)
N3	0.0566 (7)	0.0380 (6)	0.0472 (8)	−0.0019 (5)	0.0213 (6)	0.0062 (6)
N4	0.0535 (7)	0.0362 (6)	0.0553 (8)	0.0016 (5)	0.0250 (7)	0.0042 (6)
O1	0.0729 (8)	0.0519 (6)	0.0663 (8)	−0.0115 (6)	0.0284 (7)	0.0122 (6)
O2	0.0663 (7)	0.0536 (6)	0.0485 (7)	−0.0019 (5)	0.0169 (6)	0.0121 (5)
O3	0.1111 (11)	0.0498 (6)	0.0503 (7)	0.0095 (7)	0.0288 (7)	−0.0004 (6)

Geometric parameters (Å, º)

C1—C2	1.385 (2)	C14—H14A	0.9300
C1—C6	1.391 (3)	C15—O2	1.2305 (18)
C1—C7	1.454 (2)	C15—N3	1.348 (2)
C2—C3	1.373 (3)	C16—N4	1.272 (2)
C2—H2B	0.9300	C16—C17	1.463 (2)
C3—C4	1.382 (3)	C16—H16A	0.9300
C3—H3B	0.9300	C17—C18	1.384 (3)
C4—C5	1.363 (4)	C17—C22	1.390 (2)
C4—H4B	0.9300	C18—C19	1.382 (3)
C5—C6	1.367 (3)	C18—H18A	0.9300
C5—H5A	0.9300	C19—C20	1.364 (3)
C6—H6A	0.9300	C19—H19A	0.9300
C7—N1	1.270 (2)	C20—C21	1.375 (3)
C7—H7A	0.9300	C20—H20A	0.9300
C8—O1	1.2219 (17)	C21—C22	1.381 (3)
C8—N2	1.351 (2)	C21—H21A	0.9300
C8—C9	1.499 (2)	C22—H22A	0.9300
C9—C14	1.379 (2)	C23—O3	1.358 (3)
C9—C10	1.394 (2)	C23—H23A	0.9600
C10—C11	1.384 (2)	C23—H23B	0.9600
C10—H10A	0.9300	C23—H23C	0.9600
C11—C12	1.388 (2)	N1—N2	1.3838 (18)
C11—C15	1.497 (2)	N2—H2A	0.8600
C12—C13	1.383 (3)	N3—N4	1.3837 (16)
C12—H12A	0.9300	N3—H3A	0.8600
C13—C14	1.379 (3)	O3—H3C	0.8853
C13—H13A	0.9300
C2—C1—C6	118.81 (17)	C9—C14—H14A	120.0
C2—C1—C7	123.03 (15)	O2—C15—N3	122.84 (14)
C6—C1—C7	118.16 (16)	O2—C15—C11	120.92 (14)
C3—C2—C1	119.94 (18)	N3—C15—C11	116.21 (13)
C3—C2—H2B	120.0	N4—C16—C17	122.27 (15)
C1—C2—H2B	120.0	N4—C16—H16A	118.9
C2—C3—C4	120.0 (2)	C17—C16—H16A	118.9
C2—C3—H3B	120.0	C18—C17—C22	119.22 (16)
C4—C3—H3B	120.0	C18—C17—C16	118.40 (16)
C5—C4—C3	120.7 (2)	C22—C17—C16	122.37 (16)
C5—C4—H4B	119.7	C19—C18—C17	120.2 (2)
C3—C4—H4B	119.7	C19—C18—H18A	119.9
C4—C5—C6	119.5 (2)	C17—C18—H18A	119.9
C4—C5—H5A	120.3	C20—C19—C18	120.3 (2)
C6—C5—H5A	120.3	C20—C19—H19A	119.9
C5—C6—C1	121.1 (2)	C18—C19—H19A	119.9
C5—C6—H6A	119.5	C19—C20—C21	120.2 (2)
C1—C6—H6A	119.5	C19—C20—H20A	119.9
N1—C7—C1	123.54 (15)	C21—C20—H20A	119.9
N1—C7—H7A	118.2	C20—C21—C22	120.3 (2)
C1—C7—H7A	118.2	C20—C21—H21A	119.8
O1—C8—N2	122.96 (15)	C22—C21—H21A	119.8
O1—C8—C9	122.57 (15)	C21—C22—C17	119.80 (19)
N2—C8—C9	114.47 (12)	C21—C22—H22A	120.1
C14—C9—C10	119.25 (15)	C17—C22—H22A	120.1
C14—C9—C8	119.16 (14)	O3—C23—H23A	109.5
C10—C9—C8	121.56 (14)	O3—C23—H23B	109.5
C11—C10—C9	120.86 (14)	H23A—C23—H23B	109.5
C11—C10—H10A	119.6	O3—C23—H23C	109.5
C9—C10—H10A	119.6	H23A—C23—H23C	109.5
C10—C11—C12	119.15 (14)	H23B—C23—H23C	109.5
C10—C11—C15	122.34 (13)	C7—N1—N2	114.50 (13)
C12—C11—C15	118.44 (14)	C8—N2—N1	120.25 (12)
C13—C12—C11	119.88 (17)	C8—N2—H2A	119.9
C13—C12—H12A	120.1	N1—N2—H2A	119.9
C11—C12—H12A	120.1	C15—N3—N4	118.98 (13)
C14—C13—C12	120.66 (17)	C15—N3—H3A	120.5
C14—C13—H13A	119.7	N4—N3—H3A	120.5
C12—C13—H13A	119.7	C16—N4—N3	115.12 (13)
C13—C14—C9	120.07 (16)	C23—O3—H3C	112.5
C13—C14—H14A	120.0
C6—C1—C2—C3	1.2 (3)	C8—C9—C14—C13	−176.01 (18)
C7—C1—C2—C3	−178.17 (17)	C10—C11—C15—O2	151.34 (15)
C1—C2—C3—C4	−0.4 (3)	C12—C11—C15—O2	−25.5 (2)
C2—C3—C4—C5	−0.4 (4)	C10—C11—C15—N3	−26.8 (2)
C3—C4—C5—C6	0.3 (4)	C12—C11—C15—N3	156.30 (15)
C4—C5—C6—C1	0.6 (4)	N4—C16—C17—C18	−173.87 (17)
C2—C1—C6—C5	−1.3 (3)	N4—C16—C17—C22	4.9 (3)
C7—C1—C6—C5	178.1 (2)	C22—C17—C18—C19	−0.4 (3)
C2—C1—C7—N1	9.4 (3)	C16—C17—C18—C19	178.41 (19)
C6—C1—C7—N1	−169.93 (18)	C17—C18—C19—C20	0.4 (4)
O1—C8—C9—C14	−28.7 (2)	C18—C19—C20—C21	−0.7 (4)
N2—C8—C9—C14	151.56 (16)	C19—C20—C21—C22	1.1 (4)
O1—C8—C9—C10	153.04 (15)	C20—C21—C22—C17	−1.1 (3)
N2—C8—C9—C10	−26.7 (2)	C18—C17—C22—C21	0.8 (3)
C14—C9—C10—C11	−3.4 (2)	C16—C17—C22—C21	−177.99 (18)
C8—C9—C10—C11	174.88 (14)	C1—C7—N1—N2	179.25 (14)
C9—C10—C11—C12	1.3 (2)	O1—C8—N2—N1	−4.5 (2)
C9—C10—C11—C15	−175.52 (14)	C9—C8—N2—N1	175.28 (13)
C10—C11—C12—C13	1.9 (3)	C7—N1—N2—C8	−173.87 (15)
C15—C11—C12—C13	178.82 (18)	O2—C15—N3—N4	0.7 (2)
C11—C12—C13—C14	−3.0 (3)	C11—C15—N3—N4	178.84 (12)
C12—C13—C14—C9	0.8 (3)	C17—C16—N4—N3	−179.83 (13)
C10—C9—C14—C13	2.3 (3)	C15—N3—N4—C16	−177.30 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.86	2.17	3.0048 (17)	164
O3—H3C···N1^ii	0.89	2.28	3.0954 (18)	153
O3—H3C···O1^ii	0.89	2.30	2.9550 (19)	131
N3—H3A···O3	0.86	2.05	2.8848 (19)	163

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