Crystal structures of two hydrazide derivatives of mefenamic acid, 3-(2,3-di­methyl­anilino)-N′-[(E)-(furan-2-yl)methyl­idene]benzohydrazide and N′-[(E)-benzyl­idene]-2-(2,3-di­methyl­anilino)benzo­hydrazide

The mol­ecular and crystal structures of (I), C₂₀H₁₉N₃O₂, and (II), C₂₂H₂₁N₃O, are similar because they differ only in the substituent at the hydrazide N atom where a phenyl­methyl­ene moiety for (II) is present instead of a furan­methyl­ene moiety for (I).

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.095
• Data-to-parameter ratio = 11.1

Structure: II

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.092
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         39 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2             106.1 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         50 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

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

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




Datablock: II


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.065 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         24 Report

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Info

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              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

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I)

Crystal data

C20H19N3O2	F(000) = 704
Mr = 333.38	Dx = 1.302 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 13.8467 (3) Å	Cell parameters from 9755 reflections
b = 15.8409 (3) Å	θ = 3.3–74.5°
c = 8.0225 (2) Å	µ = 0.69 mm^−1
β = 104.814 (1)°	T = 150 K
V = 1701.20 (7) Å^3	Column, colourless
Z = 4	0.19 × 0.11 × 0.07 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3372 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2939 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.4167 pixels mm^-1	θmax = 74.5°, θmin = 3.3°
ω scans	h = −14→16
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −18→19
Tmin = 0.88, Tmax = 0.95	l = −9→9
13222 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	All H-atom parameters refined
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.3981P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3372 reflections	Δρmax = 0.23 e Å^−3
303 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (4)

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.

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 > 2sigma(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
O1	0.43892 (6)	0.33178 (5)	0.45837 (10)	0.0275 (2)
O2	0.10644 (7)	0.20592 (6)	0.31256 (12)	0.0371 (2)
N1	0.62923 (8)	0.38535 (8)	0.58252 (15)	0.0353 (3)
H1	0.5810 (13)	0.3629 (11)	0.495 (2)	0.051 (5)*
N2	0.37222 (7)	0.26862 (7)	0.65665 (13)	0.0262 (2)
H2	0.3836 (12)	0.2485 (11)	0.763 (2)	0.043 (4)*
N3	0.29029 (7)	0.24278 (6)	0.52997 (12)	0.0260 (2)
C1	0.70907 (9)	0.42610 (8)	0.53437 (15)	0.0279 (3)
C2	0.76645 (9)	0.37935 (8)	0.44626 (15)	0.0276 (3)
C3	0.84199 (9)	0.42133 (9)	0.39033 (15)	0.0313 (3)
C4	0.85989 (10)	0.50619 (9)	0.42738 (17)	0.0361 (3)
H4	0.9119 (12)	0.5334 (11)	0.389 (2)	0.047 (5)*
C5	0.80281 (11)	0.55168 (9)	0.51433 (19)	0.0378 (3)
H5	0.8130 (13)	0.6122 (12)	0.533 (2)	0.052 (5)*
C6	0.72631 (10)	0.51191 (9)	0.56546 (18)	0.0342 (3)
H6	0.6815 (13)	0.5435 (11)	0.618 (2)	0.052 (5)*
C7	0.74397 (12)	0.28753 (9)	0.40596 (19)	0.0381 (3)
H7A	0.6963 (16)	0.2816 (13)	0.295 (3)	0.073 (6)*
H7B	0.8049 (17)	0.2542 (14)	0.398 (3)	0.078 (6)*
H7C	0.7169 (13)	0.2599 (12)	0.493 (2)	0.055 (5)*
C8	0.90166 (13)	0.37716 (12)	0.2834 (2)	0.0470 (4)
H8A	0.8587 (14)	0.3622 (12)	0.170 (3)	0.056 (5)*
H8B	0.957 (2)	0.4145 (17)	0.265 (3)	0.105 (8)*
H8C	0.9298 (16)	0.3242 (15)	0.331 (3)	0.075 (6)*
C9	0.60374 (9)	0.39480 (8)	0.73618 (15)	0.0275 (3)
C10	0.66889 (10)	0.43330 (8)	0.88024 (16)	0.0326 (3)
H10	0.7324 (13)	0.4574 (11)	0.866 (2)	0.045 (4)*
C11	0.64394 (10)	0.44053 (9)	1.03499 (16)	0.0350 (3)
H11	0.6916 (11)	0.4702 (10)	1.131 (2)	0.037 (4)*
C12	0.55432 (10)	0.40856 (9)	1.05579 (16)	0.0343 (3)
H12	0.5341 (11)	0.4161 (10)	1.165 (2)	0.037 (4)*
C13	0.48990 (10)	0.36959 (8)	0.91722 (16)	0.0293 (3)
H13	0.4250 (12)	0.3490 (10)	0.9272 (19)	0.038 (4)*
C14	0.51281 (9)	0.36090 (7)	0.75761 (15)	0.0251 (3)
C15	0.44003 (8)	0.32000 (7)	0.61193 (14)	0.0238 (2)
C16	0.23183 (9)	0.19224 (8)	0.58218 (15)	0.0280 (3)
H16	0.2460 (11)	0.1729 (10)	0.701 (2)	0.038 (4)*
C17	0.13770 (9)	0.16726 (8)	0.46938 (16)	0.0297 (3)
C18	0.06614 (11)	0.11334 (10)	0.4926 (2)	0.0410 (3)
H18	0.0716 (14)	0.0788 (12)	0.597 (2)	0.059 (5)*
C19	−0.01455 (11)	0.11896 (10)	0.3418 (2)	0.0440 (4)
H19	−0.0782 (15)	0.0886 (12)	0.319 (2)	0.061 (5)*
C20	0.01305 (10)	0.17477 (10)	0.2391 (2)	0.0425 (4)
H20	−0.0217 (15)	0.1968 (13)	0.124 (3)	0.063 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0276 (4)	0.0337 (5)	0.0215 (4)	−0.0028 (3)	0.0067 (3)	−0.0006 (3)
O2	0.0308 (5)	0.0430 (5)	0.0328 (5)	−0.0046 (4)	−0.0004 (4)	0.0003 (4)
N1	0.0289 (6)	0.0477 (7)	0.0315 (6)	−0.0131 (5)	0.0118 (4)	−0.0092 (5)
N2	0.0236 (5)	0.0337 (5)	0.0197 (5)	−0.0034 (4)	0.0026 (4)	0.0016 (4)
N3	0.0225 (5)	0.0315 (5)	0.0229 (5)	−0.0018 (4)	0.0040 (4)	−0.0016 (4)
C1	0.0224 (6)	0.0326 (6)	0.0280 (6)	−0.0021 (5)	0.0051 (4)	0.0011 (5)
C2	0.0266 (6)	0.0307 (6)	0.0239 (6)	−0.0007 (5)	0.0037 (4)	0.0010 (5)
C3	0.0236 (6)	0.0426 (7)	0.0269 (6)	−0.0005 (5)	0.0050 (5)	0.0022 (5)
C4	0.0288 (7)	0.0433 (8)	0.0352 (7)	−0.0101 (6)	0.0065 (5)	0.0057 (6)
C5	0.0387 (8)	0.0292 (7)	0.0428 (8)	−0.0044 (5)	0.0056 (6)	0.0025 (6)
C6	0.0295 (7)	0.0321 (7)	0.0402 (7)	0.0025 (5)	0.0078 (5)	−0.0009 (5)
C7	0.0498 (9)	0.0314 (7)	0.0344 (7)	−0.0032 (6)	0.0130 (6)	−0.0027 (5)
C8	0.0392 (9)	0.0645 (11)	0.0414 (9)	−0.0004 (7)	0.0176 (7)	−0.0055 (7)
C9	0.0250 (6)	0.0297 (6)	0.0271 (6)	0.0004 (5)	0.0052 (4)	0.0000 (5)
C10	0.0260 (6)	0.0356 (7)	0.0327 (7)	−0.0025 (5)	0.0011 (5)	−0.0009 (5)
C11	0.0358 (7)	0.0358 (7)	0.0275 (6)	−0.0008 (5)	−0.0028 (5)	−0.0015 (5)
C12	0.0411 (7)	0.0370 (7)	0.0235 (6)	−0.0008 (6)	0.0060 (5)	−0.0024 (5)
C13	0.0301 (7)	0.0313 (6)	0.0268 (6)	−0.0012 (5)	0.0079 (5)	0.0003 (5)
C14	0.0232 (6)	0.0275 (6)	0.0233 (6)	0.0009 (4)	0.0033 (4)	0.0001 (4)
C15	0.0217 (6)	0.0260 (6)	0.0236 (6)	0.0023 (4)	0.0055 (4)	0.0000 (4)
C16	0.0264 (6)	0.0335 (6)	0.0249 (6)	−0.0010 (5)	0.0081 (5)	−0.0001 (5)
C17	0.0272 (6)	0.0341 (6)	0.0286 (6)	−0.0013 (5)	0.0088 (5)	−0.0029 (5)
C18	0.0342 (7)	0.0482 (8)	0.0433 (8)	−0.0102 (6)	0.0150 (6)	−0.0046 (6)
C19	0.0250 (7)	0.0502 (9)	0.0563 (9)	−0.0075 (6)	0.0097 (6)	−0.0170 (7)
C20	0.0285 (7)	0.0471 (8)	0.0451 (8)	−0.0014 (6)	−0.0033 (6)	−0.0108 (7)

Geometric parameters (Å, º)

O1—C15	1.2422 (14)	C7—H7C	0.978 (19)
O2—C17	1.3663 (16)	C8—H8A	0.98 (2)
O2—C20	1.3687 (16)	C8—H8B	1.01 (3)
N1—C9	1.3744 (16)	C8—H8C	0.96 (2)
N1—C1	1.4165 (16)	C9—C10	1.4102 (17)
N1—H1	0.910 (19)	C9—C14	1.4191 (17)
N2—C15	1.3582 (15)	C10—C11	1.3759 (19)
N2—N3	1.3777 (13)	C10—H10	0.993 (17)
N2—H2	0.883 (18)	C11—C12	1.389 (2)
N3—C16	1.2826 (16)	C11—H11	0.996 (16)
C1—C6	1.3915 (18)	C12—C13	1.3804 (18)
C1—C2	1.4023 (17)	C12—H12	0.989 (16)
C2—C3	1.4063 (17)	C13—C14	1.4024 (17)
C2—C7	1.5053 (18)	C13—H13	0.978 (16)
C3—C4	1.385 (2)	C14—C15	1.4829 (15)
C3—C8	1.507 (2)	C16—C17	1.4392 (17)
C4—C5	1.383 (2)	C16—H16	0.973 (16)
C4—H4	0.955 (17)	C17—C18	1.3566 (19)
C5—C6	1.3818 (19)	C18—C19	1.424 (2)
C5—H5	0.975 (19)	C18—H18	0.990 (19)
C6—H6	0.976 (18)	C19—C20	1.330 (2)
C7—H7A	0.97 (2)	C19—H19	0.98 (2)
C7—H7B	1.01 (2)	C20—H20	0.99 (2)
C17—O2—C20	106.08 (11)	H8B—C8—H8C	108.9 (19)
C9—N1—C1	126.32 (11)	N1—C9—C10	121.67 (11)
C9—N1—H1	115.6 (11)	N1—C9—C14	120.45 (11)
C1—N1—H1	115.8 (11)	C10—C9—C14	117.77 (11)
C15—N2—N3	118.53 (10)	C11—C10—C9	121.32 (12)
C15—N2—H2	120.4 (11)	C11—C10—H10	120.6 (10)
N3—N2—H2	120.9 (11)	C9—C10—H10	118.0 (10)
C16—N3—N2	114.45 (10)	C10—C11—C12	121.07 (12)
C6—C1—C2	120.85 (11)	C10—C11—H11	118.0 (9)
C6—C1—N1	120.43 (11)	C12—C11—H11	120.9 (9)
C2—C1—N1	118.62 (11)	C13—C12—C11	118.64 (12)
C1—C2—C3	118.33 (11)	C13—C12—H12	119.6 (9)
C1—C2—C7	120.39 (11)	C11—C12—H12	121.7 (9)
C3—C2—C7	121.21 (12)	C12—C13—C14	121.92 (12)
C4—C3—C2	119.82 (12)	C12—C13—H13	120.1 (9)
C4—C3—C8	118.60 (13)	C14—C13—H13	118.0 (9)
C2—C3—C8	121.53 (13)	C13—C14—C9	119.23 (11)
C5—C4—C3	121.32 (12)	C13—C14—C15	119.71 (11)
C5—C4—H4	120.2 (10)	C9—C14—C15	121.00 (10)
C3—C4—H4	118.5 (10)	O1—C15—N2	121.19 (10)
C6—C5—C4	119.50 (13)	O1—C15—C14	123.33 (10)
C6—C5—H5	119.7 (10)	N2—C15—C14	115.47 (10)
C4—C5—H5	120.7 (10)	N3—C16—C17	120.80 (11)
C5—C6—C1	120.11 (13)	N3—C16—H16	122.0 (9)
C5—C6—H6	121.1 (11)	C17—C16—H16	117.0 (9)
C1—C6—H6	118.7 (11)	C18—C17—O2	109.77 (12)
C2—C7—H7A	110.2 (13)	C18—C17—C16	131.50 (13)
C2—C7—H7B	112.8 (13)	O2—C17—C16	118.59 (11)
H7A—C7—H7B	106.1 (17)	C17—C18—C19	106.60 (14)
C2—C7—H7C	112.1 (11)	C17—C18—H18	124.4 (11)
H7A—C7—H7C	108.4 (16)	C19—C18—H18	129.0 (11)
H7B—C7—H7C	106.9 (17)	C20—C19—C18	106.30 (13)
C3—C8—H8A	110.5 (11)	C20—C19—H19	126.7 (11)
C3—C8—H8B	111.0 (15)	C18—C19—H19	127.0 (11)
H8A—C8—H8B	108.1 (18)	C19—C20—O2	111.25 (13)
C3—C8—H8C	113.8 (13)	C19—C20—H20	131.6 (12)
H8A—C8—H8C	104.2 (17)	O2—C20—H20	117.1 (12)
C15—N2—N3—C16	177.81 (11)	C11—C12—C13—C14	0.5 (2)
C9—N1—C1—C6	−44.52 (19)	C12—C13—C14—C9	−1.49 (19)
C9—N1—C1—C2	139.08 (13)	C12—C13—C14—C15	−178.79 (12)
C6—C1—C2—C3	0.10 (18)	N1—C9—C14—C13	178.37 (11)
N1—C1—C2—C3	176.49 (11)	C10—C9—C14—C13	2.26 (17)
C6—C1—C2—C7	−177.09 (12)	N1—C9—C14—C15	−4.36 (18)
N1—C1—C2—C7	−0.70 (18)	C10—C9—C14—C15	179.53 (11)
C1—C2—C3—C4	1.90 (18)	N3—N2—C15—O1	−12.62 (17)
C7—C2—C3—C4	179.07 (12)	N3—N2—C15—C14	166.53 (10)
C1—C2—C3—C8	−175.36 (12)	C13—C14—C15—O1	157.42 (11)
C7—C2—C3—C8	1.81 (19)	C9—C14—C15—O1	−19.84 (18)
C2—C3—C4—C5	−1.98 (19)	C13—C14—C15—N2	−21.70 (16)
C8—C3—C4—C5	175.36 (13)	C9—C14—C15—N2	161.04 (11)
C3—C4—C5—C6	0.0 (2)	N2—N3—C16—C17	173.06 (11)
C4—C5—C6—C1	2.0 (2)	C20—O2—C17—C18	0.28 (15)
C2—C1—C6—C5	−2.09 (19)	C20—O2—C17—C16	−175.78 (12)
N1—C1—C6—C5	−178.41 (12)	N3—C16—C17—C18	177.42 (14)
C1—N1—C9—C10	−14.2 (2)	N3—C16—C17—O2	−7.54 (18)
C1—N1—C9—C14	169.88 (12)	O2—C17—C18—C19	−0.22 (16)
N1—C9—C10—C11	−178.26 (12)	C16—C17—C18—C19	175.15 (13)
C14—C9—C10—C11	−2.20 (19)	C17—C18—C19—C20	0.08 (17)
C9—C10—C11—C12	1.3 (2)	C18—C19—C20—O2	0.10 (18)
C10—C11—C12—C13	−0.4 (2)	C17—O2—C20—C19	−0.23 (16)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C17–C20/O2 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.910 (19)	1.977 (18)	2.7045 (14)	135.8 (15)
N2—H2···O1^i	0.883 (18)	2.014 (18)	2.8458 (13)	156.4 (15)
C4—H4···Cg1^ii	0.955 (17)	2.941 (17)	3.7248 (15)	140.1 (17)
C6—H6···O1^iii	0.976 (18)	2.556 (18)	3.3434 (16)	137.7 (14)
C11—H11···Cg2^iv	0.996 (16)	2.765 (16)	3.6231 (14)	144.8 (12)

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

N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II)

Crystal data

C22H21N3O	F(000) = 728
Mr = 343.42	Dx = 1.256 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 14.3493 (8) Å	Cell parameters from 9904 reflections
b = 15.7501 (9) Å	θ = 4.3–74.6°
c = 8.3737 (5) Å	µ = 0.62 mm^−1
β = 106.285 (2)°	T = 150 K
V = 1816.55 (18) Å^3	Block, pale yellow
Z = 4	0.19 × 0.13 × 0.08 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3665 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3140 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.4167 pixels mm^-1	θmax = 74.6°, θmin = 4.3°
ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −19→18
Tmin = 0.86, Tmax = 0.95	l = −10→9
13875 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	All H-atom parameters refined
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 0.444P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3665 reflections	Δρmax = 0.17 e Å^−3
320 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (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.

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 > 2sigma(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
O1	0.44514 (6)	0.33126 (6)	0.43024 (9)	0.0300 (2)
N1	0.62636 (8)	0.39413 (8)	0.53993 (14)	0.0392 (3)
H1	0.5771 (13)	0.3712 (11)	0.458 (2)	0.051 (5)*
N2	0.39227 (7)	0.26174 (7)	0.62519 (12)	0.0287 (2)
H2	0.4042 (11)	0.2421 (10)	0.732 (2)	0.040 (4)*
N3	0.30815 (7)	0.23802 (7)	0.50842 (12)	0.0278 (2)
C1	0.70441 (8)	0.43293 (8)	0.49433 (14)	0.0301 (3)
C2	0.75817 (9)	0.38475 (8)	0.41121 (14)	0.0301 (3)
C3	0.83421 (9)	0.42441 (9)	0.36395 (15)	0.0330 (3)
C4	0.85496 (10)	0.50931 (9)	0.40197 (17)	0.0386 (3)
H4	0.9098 (13)	0.5351 (11)	0.367 (2)	0.052 (5)*
C5	0.80049 (11)	0.55653 (9)	0.48198 (18)	0.0411 (3)
H5	0.8132 (13)	0.6202 (12)	0.504 (2)	0.053 (5)*
C6	0.72458 (10)	0.51889 (9)	0.52686 (16)	0.0365 (3)
H6	0.6833 (13)	0.5527 (12)	0.578 (2)	0.054 (5)*
C7	0.73544 (13)	0.29257 (9)	0.3725 (2)	0.0451 (4)
H7A	0.7008 (18)	0.2847 (16)	0.256 (3)	0.095 (7)*
H7B	0.7995 (19)	0.2567 (16)	0.388 (3)	0.096 (8)*
H7C	0.6979 (15)	0.2671 (13)	0.443 (3)	0.072 (6)*
C8	0.89350 (12)	0.37677 (12)	0.2713 (2)	0.0490 (4)
H8A	0.8504 (15)	0.3577 (13)	0.155 (3)	0.068 (6)*
H8B	0.9499 (16)	0.4120 (13)	0.259 (2)	0.074 (6)*
H8C	0.9197 (17)	0.3238 (15)	0.328 (3)	0.083 (7)*
C9	0.60826 (8)	0.39908 (8)	0.69193 (14)	0.0300 (3)
C10	0.67446 (9)	0.43734 (9)	0.83041 (16)	0.0356 (3)
H10	0.7358 (12)	0.4613 (10)	0.8156 (19)	0.045 (4)*
C11	0.65461 (10)	0.44332 (9)	0.98135 (16)	0.0391 (3)
H11	0.7018 (12)	0.4732 (10)	1.073 (2)	0.045 (4)*
C12	0.56938 (10)	0.41042 (9)	1.00387 (16)	0.0386 (3)
H12	0.5526 (12)	0.4186 (11)	1.110 (2)	0.053 (5)*
C13	0.50518 (9)	0.36998 (8)	0.87248 (15)	0.0323 (3)
H13	0.4448 (11)	0.3485 (10)	0.8855 (18)	0.037 (4)*
C14	0.52311 (8)	0.36209 (8)	0.71679 (14)	0.0273 (3)
C15	0.45190 (8)	0.31809 (8)	0.57935 (14)	0.0259 (2)
C16	0.25463 (8)	0.18507 (8)	0.55850 (14)	0.0283 (3)
H16	0.2745 (11)	0.1595 (10)	0.6724 (19)	0.039 (4)*
C17	0.15643 (8)	0.16629 (8)	0.45380 (14)	0.0270 (2)
C18	0.11897 (9)	0.20627 (8)	0.30028 (15)	0.0325 (3)
H18	0.1624 (12)	0.2442 (11)	0.258 (2)	0.046 (4)*
C19	0.02375 (10)	0.19387 (9)	0.20915 (17)	0.0387 (3)
H19	−0.0003 (12)	0.2241 (11)	0.098 (2)	0.051 (5)*
C20	−0.03663 (9)	0.14166 (9)	0.26957 (17)	0.0377 (3)
H20	−0.1059 (13)	0.1325 (11)	0.205 (2)	0.050 (4)*
C21	−0.00080 (9)	0.10191 (9)	0.42071 (17)	0.0373 (3)
H21	−0.0449 (13)	0.0660 (11)	0.467 (2)	0.051 (4)*
C22	0.09561 (9)	0.11354 (9)	0.51326 (16)	0.0333 (3)
H22	0.1219 (11)	0.0868 (10)	0.6234 (19)	0.038 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0270 (4)	0.0408 (5)	0.0213 (4)	−0.0033 (3)	0.0051 (3)	−0.0017 (3)
N1	0.0290 (5)	0.0598 (8)	0.0297 (5)	−0.0158 (5)	0.0096 (4)	−0.0104 (5)
N2	0.0229 (5)	0.0392 (6)	0.0212 (5)	−0.0030 (4)	0.0019 (4)	0.0015 (4)
N3	0.0219 (5)	0.0362 (6)	0.0235 (5)	−0.0016 (4)	0.0034 (4)	−0.0018 (4)
C1	0.0235 (5)	0.0390 (7)	0.0261 (6)	−0.0033 (5)	0.0041 (4)	0.0003 (5)
C2	0.0309 (6)	0.0328 (6)	0.0253 (6)	−0.0003 (5)	0.0053 (5)	0.0017 (5)
C3	0.0282 (6)	0.0424 (7)	0.0281 (6)	0.0030 (5)	0.0076 (5)	0.0056 (5)
C4	0.0333 (7)	0.0454 (8)	0.0364 (7)	−0.0080 (6)	0.0085 (5)	0.0067 (6)
C5	0.0463 (8)	0.0333 (7)	0.0417 (7)	−0.0066 (6)	0.0092 (6)	0.0012 (6)
C6	0.0354 (7)	0.0362 (7)	0.0368 (7)	0.0037 (5)	0.0083 (5)	−0.0027 (5)
C7	0.0632 (10)	0.0346 (7)	0.0402 (8)	−0.0068 (7)	0.0189 (7)	−0.0025 (6)
C8	0.0463 (8)	0.0616 (10)	0.0453 (9)	0.0114 (8)	0.0229 (7)	0.0053 (7)
C9	0.0248 (5)	0.0366 (7)	0.0263 (6)	−0.0003 (5)	0.0034 (4)	−0.0009 (5)
C10	0.0292 (6)	0.0416 (7)	0.0306 (6)	−0.0046 (5)	−0.0005 (5)	−0.0013 (5)
C11	0.0416 (7)	0.0412 (7)	0.0268 (6)	−0.0047 (6)	−0.0030 (5)	−0.0025 (5)
C12	0.0467 (7)	0.0436 (8)	0.0234 (6)	−0.0018 (6)	0.0065 (5)	−0.0032 (5)
C13	0.0336 (6)	0.0367 (7)	0.0260 (6)	−0.0004 (5)	0.0074 (5)	−0.0008 (5)
C14	0.0246 (5)	0.0329 (6)	0.0226 (5)	0.0012 (5)	0.0037 (4)	−0.0007 (4)
C15	0.0205 (5)	0.0326 (6)	0.0237 (5)	0.0029 (4)	0.0050 (4)	0.0003 (4)
C16	0.0260 (6)	0.0352 (6)	0.0236 (5)	0.0009 (5)	0.0066 (4)	0.0004 (5)
C17	0.0251 (6)	0.0307 (6)	0.0252 (5)	0.0008 (5)	0.0070 (4)	−0.0030 (4)
C18	0.0300 (6)	0.0369 (7)	0.0292 (6)	0.0000 (5)	0.0057 (5)	0.0012 (5)
C19	0.0330 (7)	0.0451 (8)	0.0326 (7)	0.0035 (6)	0.0001 (5)	0.0003 (6)
C20	0.0244 (6)	0.0447 (8)	0.0402 (7)	0.0007 (5)	0.0028 (5)	−0.0106 (6)
C21	0.0298 (6)	0.0425 (7)	0.0411 (7)	−0.0077 (6)	0.0123 (5)	−0.0075 (6)
C22	0.0306 (6)	0.0381 (7)	0.0306 (6)	−0.0049 (5)	0.0076 (5)	−0.0009 (5)

Geometric parameters (Å, º)

O1—C15	1.2424 (14)	C9—C10	1.4115 (17)
N1—C9	1.3707 (16)	C9—C14	1.4208 (17)
N1—C1	1.4189 (16)	C10—C11	1.3745 (19)
N1—H1	0.908 (18)	C10—H10	0.997 (16)
N2—C15	1.3607 (16)	C11—C12	1.389 (2)
N2—N3	1.3750 (13)	C11—H11	0.990 (16)
N2—H2	0.913 (16)	C12—C13	1.3770 (18)
N3—C16	1.2814 (16)	C12—H12	0.988 (17)
C1—C6	1.3954 (19)	C13—C14	1.4033 (16)
C1—C2	1.3987 (17)	C13—H13	0.965 (16)
C2—C3	1.4068 (17)	C14—C15	1.4796 (15)
C2—C7	1.5034 (19)	C16—C17	1.4659 (16)
C3—C4	1.387 (2)	C16—H16	1.000 (15)
C3—C8	1.5030 (19)	C17—C22	1.3941 (17)
C4—C5	1.381 (2)	C17—C18	1.3966 (17)
C4—H4	1.001 (17)	C18—C19	1.3793 (18)
C5—C6	1.382 (2)	C18—H18	0.997 (17)
C5—H5	1.026 (18)	C19—C20	1.389 (2)
C6—H6	0.980 (18)	C19—H19	1.013 (18)
C7—H7A	0.97 (3)	C20—C21	1.376 (2)
C7—H7B	1.06 (3)	C20—H20	1.000 (18)
C7—H7C	0.99 (2)	C21—C22	1.3952 (18)
C8—H8A	1.04 (2)	C21—H21	1.004 (18)
C8—H8B	1.01 (2)	C22—H22	0.988 (15)
C8—H8C	0.98 (2)
C9—N1—C1	126.50 (11)	C11—C10—C9	121.30 (12)
C9—N1—H1	114.2 (11)	C11—C10—H10	120.4 (9)
C1—N1—H1	118.4 (11)	C9—C10—H10	118.3 (9)
C15—N2—N3	118.21 (10)	C10—C11—C12	121.11 (12)
C15—N2—H2	122.4 (10)	C10—C11—H11	118.3 (9)
N3—N2—H2	119.3 (10)	C12—C11—H11	120.6 (9)
C16—N3—N2	115.55 (10)	C13—C12—C11	118.77 (12)
C6—C1—C2	120.68 (11)	C13—C12—H12	120.0 (10)
C6—C1—N1	120.10 (12)	C11—C12—H12	121.2 (10)
C2—C1—N1	119.17 (12)	C12—C13—C14	121.83 (12)
C1—C2—C3	118.60 (12)	C12—C13—H13	119.5 (9)
C1—C2—C7	120.96 (12)	C14—C13—H13	118.6 (9)
C3—C2—C7	120.44 (12)	C13—C14—C9	119.28 (11)
C4—C3—C2	119.79 (12)	C13—C14—C15	119.84 (11)
C4—C3—C8	118.91 (13)	C9—C14—C15	120.85 (10)
C2—C3—C8	121.30 (13)	O1—C15—N2	120.95 (10)
C5—C4—C3	121.08 (12)	O1—C15—C14	123.08 (10)
C5—C4—H4	121.5 (10)	N2—C15—C14	115.96 (10)
C3—C4—H4	117.4 (10)	N3—C16—C17	119.96 (11)
C4—C5—C6	119.84 (13)	N3—C16—H16	122.5 (9)
C4—C5—H5	121.3 (9)	C17—C16—H16	117.3 (9)
C6—C5—H5	118.8 (10)	C22—C17—C18	118.65 (11)
C5—C6—C1	119.96 (12)	C22—C17—C16	119.98 (11)
C5—C6—H6	120.4 (10)	C18—C17—C16	121.12 (11)
C1—C6—H6	119.6 (10)	C19—C18—C17	120.75 (12)
C2—C7—H7A	111.1 (15)	C19—C18—H18	120.5 (9)
C2—C7—H7B	111.2 (13)	C17—C18—H18	118.7 (9)
H7A—C7—H7B	103.8 (19)	C18—C19—C20	120.31 (12)
C2—C7—H7C	112.7 (12)	C18—C19—H19	118.0 (10)
H7A—C7—H7C	109.5 (19)	C20—C19—H19	121.7 (10)
H7B—C7—H7C	108.2 (18)	C21—C20—C19	119.62 (12)
C3—C8—H8A	110.6 (11)	C21—C20—H20	119.3 (10)
C3—C8—H8B	111.4 (12)	C19—C20—H20	121.0 (10)
H8A—C8—H8B	110.3 (15)	C20—C21—C22	120.51 (12)
C3—C8—H8C	111.8 (13)	C20—C21—H21	119.9 (10)
H8A—C8—H8C	104.6 (17)	C22—C21—H21	119.6 (10)
H8B—C8—H8C	107.9 (18)	C17—C22—C21	120.16 (12)
N1—C9—C10	121.87 (11)	C17—C22—H22	118.3 (9)
N1—C9—C14	120.49 (10)	C21—C22—H22	121.5 (9)
C10—C9—C14	117.58 (11)
C15—N2—N3—C16	−179.78 (11)	C12—C13—C14—C9	−2.03 (19)
C9—N1—C1—C6	−49.49 (19)	C12—C13—C14—C15	−179.98 (12)
C9—N1—C1—C2	132.87 (14)	N1—C9—C14—C13	−178.39 (12)
C6—C1—C2—C3	1.20 (17)	C10—C9—C14—C13	4.26 (18)
N1—C1—C2—C3	178.83 (11)	N1—C9—C14—C15	−0.46 (18)
C6—C1—C2—C7	−178.68 (12)	C10—C9—C14—C15	−177.81 (11)
N1—C1—C2—C7	−1.05 (18)	N3—N2—C15—O1	−18.17 (17)
C1—C2—C3—C4	0.75 (18)	N3—N2—C15—C14	161.30 (10)
C7—C2—C3—C4	−179.36 (12)	C13—C14—C15—O1	156.06 (12)
C1—C2—C3—C8	−178.75 (12)	C9—C14—C15—O1	−21.86 (18)
C7—C2—C3—C8	1.13 (19)	C13—C14—C15—N2	−23.40 (16)
C2—C3—C4—C5	−1.70 (19)	C9—C14—C15—N2	158.68 (11)
C8—C3—C4—C5	177.82 (13)	N2—N3—C16—C17	169.95 (10)
C3—C4—C5—C6	0.7 (2)	N3—C16—C17—C22	−175.28 (12)
C4—C5—C6—C1	1.3 (2)	N3—C16—C17—C18	−1.04 (18)
C2—C1—C6—C5	−2.25 (19)	C22—C17—C18—C19	−0.02 (19)
N1—C1—C6—C5	−179.86 (12)	C16—C17—C18—C19	−174.33 (12)
C1—N1—C9—C10	−7.4 (2)	C17—C18—C19—C20	0.4 (2)
C1—N1—C9—C14	175.32 (12)	C18—C19—C20—C21	−0.3 (2)
N1—C9—C10—C11	178.76 (13)	C19—C20—C21—C22	−0.1 (2)
C14—C9—C10—C11	−3.9 (2)	C18—C17—C22—C21	−0.45 (19)
C9—C10—C11—C12	1.2 (2)	C16—C17—C22—C21	173.93 (12)
C10—C11—C12—C13	1.2 (2)	C20—C21—C22—C17	0.5 (2)
C11—C12—C13—C14	−0.7 (2)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg3 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.908 (18)	1.946 (18)	2.6920 (13)	138.2 (15)
N2—H2···O1^i	0.913 (16)	1.974 (17)	2.8564 (13)	162.0 (14)
C4—H4···Cg3^ii	1.001 (17)	2.796 (17)	3.6141 (15)	139.4 (13)
C6—H6···O1^iii	0.980 (18)	2.583 (19)	3.4815 (16)	152.5 (13)
C20—H20···Cg1^iv	1.000 (18)	2.838 (17)	3.6644 (15)	140.5 (13)

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