Synthesis and crystal structures of (E)-N′-(4-chloro-3-nitro­benzyl­idene)acetohydrazide and (E)-2-(4-chloro­benzyl­idene)-1-(quinolin-8-yl)hydrazine

Two benzyl­idenehydrazinederivatives have been synthesized and structurally characterized.

Key indicators

Structure: IV

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.038
• wR factor = 0.111
• Data-to-parameter ratio = 12.1

Structure: VII

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.031
• wR factor = 0.085
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Datablock: IV


Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          7 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT168_ALERT_4_G The CIF-Embedded .res File Contains EXYZ Records          1 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT189_ALERT_3_G A Non-default SAME Restraint Value for First Par     0.0010 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        25% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1A      ..C9       .       2.91 Ang.
                                                1-x,1-y,1-z  =      3_666 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3       ..O1       .       2.61 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        132 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         27 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.8 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

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




Datablock: VII



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H15      ..CL1      .       3.04 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H30      ..CL2      .       3.05 Ang.
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         29 Note
PLAT915_ALERT_3_G No Flack x Check Done: Low Friedel Pair Coverage         42 %
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.3 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 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
   9 ALERT level G = General information/check it is not something unexpected

   1 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
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2020).

(E)-N'-(4-Chloro-3-nitrobenzylidene)acetohydrazide (IV)

Crystal data

C9H8ClN3O3	F(000) = 496
Mr = 241.63	Dx = 1.500 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 4.4717 (1) Å	Cell parameters from 5559 reflections
b = 11.9367 (2) Å	θ = 4.3–72.9°
c = 20.1382 (3) Å	µ = 3.17 mm^−1
β = 95.689 (2)°	T = 293 K
V = 1069.63 (3) Å^3	Plate, yellow
Z = 4	0.34 × 0.21 × 0.06 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	1960 reflections with I > 2σ(I)
ω scans	Rint = 0.021
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2022)	θmax = 72.6°, θmin = 4.3°
Tmin = 0.500, Tmax = 1.000	h = −5→4
7967 measured reflections	k = −11→14
2107 independent reflections	l = −24→23

Refinement

Refinement on F^2	132 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0628P)^2 + 0.2562P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2107 reflections	Δρmax = 0.30 e Å^−3
174 parameters	Δρmin = −0.26 e Å^−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. Single-crystal XRD data were collected on an Agilent SuperNova Dual Atlas diffractometer with a mirror monochromator using Cu radiation. Crystal structures were solved and refined using SHELXT (Sheldrick, 2015a) and SHELXL (Sheldrick, 2015b). Non-hydrogen atoms for both IV and VII were refined with anisotropic displacement parameters.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	1.1687 (3)	0.64078 (14)	0.65566 (9)	0.0471 (4)	0.837 (4)
N1	1.2480 (5)	0.52916 (17)	0.63231 (17)	0.0625 (7)	0.837 (4)
O1	1.2534 (7)	0.45143 (16)	0.67293 (12)	0.0952 (8)	0.837 (4)
O2	1.2958 (7)	0.51630 (18)	0.57543 (12)	0.1103 (10)	0.837 (4)
C1A	1.1687 (3)	0.64078 (14)	0.65566 (9)	0.0471 (4)	0.163 (4)
N1A	1.2420 (17)	0.5222 (3)	0.6464 (8)	0.068 (3)	0.163 (4)
O1A	1.034 (2)	0.4543 (3)	0.6471 (9)	0.116 (4)	0.163 (4)
O2A	1.4995 (17)	0.4946 (6)	0.6475 (7)	0.090 (3)	0.163 (4)
C2	1.3004 (3)	0.68734 (15)	0.71455 (8)	0.0482 (4)
C3	1.2216 (4)	0.79476 (16)	0.73109 (8)	0.0512 (4)
H3	1.313563	0.828395	0.769479	0.061*
C4	1.0057 (4)	0.85255 (15)	0.69064 (8)	0.0472 (4)
H4	0.952715	0.924666	0.702441	0.057*
C5	0.8667 (3)	0.80468 (13)	0.63268 (7)	0.0411 (3)
C6	0.9539 (3)	0.69802 (13)	0.61454 (8)	0.0450 (4)
H6	0.868744	0.665462	0.575164	0.054*
C7	0.6293 (3)	0.86655 (13)	0.59289 (8)	0.0415 (3)
H7	0.572080	0.936881	0.606968	0.050*
C8	0.1213 (3)	0.85608 (14)	0.44985 (8)	0.0446 (3)
C9	0.2010 (5)	0.74632 (18)	0.42125 (11)	0.0691 (5)
H9A	0.062133	0.729457	0.383109	0.104*
H9B	0.191210	0.688737	0.454244	0.104*
H9C	0.401094	0.749991	0.407961	0.104*
N2	0.5005 (3)	0.82510 (11)	0.53927 (6)	0.0419 (3)
N3	0.2774 (3)	0.88996 (11)	0.50721 (7)	0.0428 (3)
H3A	0.235971	0.953659	0.524035	0.051*
O3	−0.0780 (3)	0.91708 (11)	0.42345 (6)	0.0548 (3)
Cl1	1.56369 (10)	0.61768 (4)	0.76803 (3)	0.0685 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0399 (7)	0.0448 (8)	0.0565 (9)	−0.0002 (6)	0.0039 (7)	0.0106 (7)
N1	0.0628 (13)	0.0481 (11)	0.0749 (17)	0.0061 (10)	−0.0019 (10)	0.0087 (10)
O1	0.137 (2)	0.0523 (11)	0.0910 (15)	0.0084 (12)	−0.0170 (14)	0.0188 (10)
O2	0.171 (2)	0.0700 (13)	0.0966 (17)	0.0287 (14)	0.0491 (17)	−0.0050 (11)
C1A	0.0399 (7)	0.0448 (8)	0.0565 (9)	−0.0002 (6)	0.0039 (7)	0.0106 (7)
N1A	0.071 (5)	0.055 (5)	0.078 (5)	0.002 (4)	0.007 (4)	0.015 (4)
O1A	0.122 (8)	0.077 (6)	0.146 (8)	−0.015 (6)	0.003 (7)	−0.005 (6)
O2A	0.072 (5)	0.060 (5)	0.138 (7)	0.027 (4)	0.010 (5)	−0.007 (5)
C2	0.0362 (7)	0.0569 (9)	0.0509 (9)	−0.0012 (6)	0.0014 (6)	0.0177 (7)
C3	0.0457 (8)	0.0625 (10)	0.0435 (8)	−0.0052 (7)	−0.0046 (7)	0.0048 (7)
C4	0.0446 (8)	0.0496 (9)	0.0464 (8)	−0.0002 (7)	0.0003 (6)	0.0018 (7)
C5	0.0343 (7)	0.0465 (8)	0.0421 (7)	−0.0018 (6)	0.0021 (6)	0.0084 (6)
C6	0.0418 (7)	0.0462 (8)	0.0461 (8)	−0.0028 (6)	−0.0005 (6)	0.0049 (6)
C7	0.0356 (7)	0.0437 (8)	0.0447 (8)	0.0003 (6)	0.0016 (6)	0.0053 (6)
C8	0.0418 (7)	0.0490 (8)	0.0422 (8)	−0.0022 (6)	−0.0003 (6)	0.0015 (6)
C9	0.0786 (13)	0.0622 (11)	0.0628 (11)	0.0109 (10)	−0.0116 (10)	−0.0160 (9)
N2	0.0359 (6)	0.0448 (7)	0.0444 (7)	0.0028 (5)	0.0004 (5)	0.0067 (5)
N3	0.0396 (6)	0.0429 (7)	0.0443 (7)	0.0049 (5)	−0.0044 (5)	0.0006 (5)
O3	0.0522 (6)	0.0591 (7)	0.0494 (6)	0.0066 (5)	−0.0138 (5)	−0.0016 (5)
Cl1	0.0502 (3)	0.0778 (4)	0.0735 (3)	0.0036 (2)	−0.0134 (2)	0.0291 (2)

Geometric parameters (Å, º)

C1—C6	1.385 (2)	C4—H4	0.9300
C1—C2	1.387 (2)	C5—C6	1.391 (2)
C1—N1	1.468 (3)	C5—C7	1.465 (2)
N1—O2	1.196 (4)	C6—H6	0.9300
N1—O1	1.236 (3)	C7—N2	1.273 (2)
C1A—C6	1.385 (2)	C7—H7	0.9300
C1A—C2	1.387 (2)	C8—O3	1.230 (2)
C1A—N1A	1.469 (3)	C8—N3	1.351 (2)
N1A—O2A	1.196 (4)	C8—C9	1.489 (3)
N1A—O1A	1.236 (4)	C9—H9A	0.9600
C2—C3	1.379 (3)	C9—H9B	0.9600
C2—Cl1	1.7281 (15)	C9—H9C	0.9600
C3—C4	1.384 (2)	N2—N3	1.3726 (17)
C3—H3	0.9300	N3—H3A	0.8600
C4—C5	1.390 (2)
C6—C1—C2	121.62 (15)	C4—C5—C6	118.90 (14)
C6—C1—N1	115.56 (19)	C4—C5—C7	119.45 (14)
C2—C1—N1	122.81 (18)	C6—C5—C7	121.64 (14)
O2—N1—O1	123.0 (2)	C1A—C6—C5	119.37 (15)
O2—N1—C1	119.7 (2)	C1—C6—C5	119.37 (15)
O1—N1—C1	117.3 (3)	C1—C6—H6	120.3
C6—C1A—C2	121.62 (15)	C5—C6—H6	120.3
C6—C1A—N1A	123.4 (6)	N2—C7—C5	120.71 (14)
C2—C1A—N1A	114.4 (6)	N2—C7—H7	119.6
O2A—N1A—O1A	122.9 (3)	C5—C7—H7	119.6
O2A—N1A—C1A	119.4 (3)	O3—C8—N3	118.88 (15)
O1A—N1A—C1A	117.0 (3)	O3—C8—C9	123.02 (15)
C3—C2—C1	118.81 (14)	N3—C8—C9	118.10 (15)
C3—C2—C1A	118.81 (14)	C8—C9—H9A	109.5
C3—C2—Cl1	118.12 (13)	C8—C9—H9B	109.5
C1—C2—Cl1	123.06 (14)	H9A—C9—H9B	109.5
C1A—C2—Cl1	123.06 (14)	C8—C9—H9C	109.5
C2—C3—C4	120.07 (16)	H9A—C9—H9C	109.5
C2—C3—H3	120.0	H9B—C9—H9C	109.5
C4—C3—H3	120.0	C7—N2—N3	115.24 (13)
C3—C4—C5	121.15 (16)	C8—N3—N2	121.54 (13)
C3—C4—H4	119.4	C8—N3—H3A	119.2
C5—C4—H4	119.4	N2—N3—H3A	119.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3^i	0.86	2.04	2.8803 (18)	167
C3—H3···O1^ii	0.93	2.61	3.442 (3)	149
C9—H9A···O1A^iii	0.96	2.30	2.906 (8)	120

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

(E)-2-(4-Chlorobenzylidene)-1-(quinolin-8-yl)hydrazine (VII)

Crystal data

C16H12ClN3	F(000) = 584
Mr = 281.74	Dx = 1.358 Mg m^−3
Monoclinic, Pn	Cu Kα radiation, λ = 1.54184 Å
a = 7.7968 (3) Å	Cell parameters from 6539 reflections
b = 12.0926 (4) Å	θ = 3.6–72.7°
c = 14.8738 (5) Å	µ = 2.38 mm^−1
β = 100.601 (3)°	T = 296 K
V = 1378.42 (8) Å^3	Plate, brown
Z = 4	0.26 × 0.14 × 0.07 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	3609 reflections with I > 2σ(I)
ω scans	Rint = 0.024
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2022)	θmax = 72.8°, θmin = 3.7°
Tmin = 0.713, Tmax = 1.000	h = −9→6
11753 measured reflections	k = −14→14
3869 independent reflections	l = −18→18

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 0.0525P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.085	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.12 e Å^−3
3869 reflections	Δρmin = −0.14 e Å^−3
361 parameters	Absolute structure: Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.016 (12)

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. Single-crystal XRD data were collected on an Agilent SuperNova Dual Atlas diffractometer with a mirror monochromator using Cu radiation. Crystal structures were solved and refined using SHELXT (Sheldrick, 2015a) and SHELXL (Sheldrick, 2015b). Non-hydrogen atoms for both IV and VII were refined with anisotropic displacement parameters.

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

	x	y	z	Uiso*/Ueq
C1	0.6750 (3)	0.4572 (2)	0.58792 (17)	0.0527 (5)
C2	0.5178 (4)	0.5151 (2)	0.58122 (18)	0.0576 (6)
H2	0.507242	0.585152	0.554930	0.069*
C3	0.3785 (4)	0.4695 (2)	0.61317 (19)	0.0591 (6)
H3	0.274364	0.508481	0.608568	0.071*
C4	0.3949 (4)	0.3653 (2)	0.65215 (17)	0.0559 (6)
C5	0.5470 (4)	0.3067 (2)	0.66004 (18)	0.0618 (6)
H5	0.556356	0.236933	0.686762	0.074*
C6	0.6876 (4)	0.3525 (2)	0.62774 (19)	0.0602 (6)
H6	0.791158	0.312863	0.632762	0.072*
C7	0.8253 (4)	0.5031 (2)	0.55413 (19)	0.0581 (6)
H7	0.925239	0.460403	0.556268	0.070*
C8	0.9657 (3)	0.73712 (19)	0.44787 (16)	0.0506 (5)
C9	0.8354 (4)	0.8142 (2)	0.44385 (18)	0.0565 (6)
H9	0.740133	0.800018	0.471623	0.068*
C10	0.8462 (4)	0.9148 (2)	0.39764 (19)	0.0620 (6)
H10	0.755828	0.965694	0.394070	0.074*
C11	0.9862 (4)	0.9395 (2)	0.35786 (19)	0.0592 (6)
H11	0.990642	1.006567	0.327755	0.071*
C12	1.1237 (3)	0.8630 (2)	0.36266 (16)	0.0516 (5)
C13	1.1132 (3)	0.75964 (19)	0.40668 (16)	0.0502 (5)
C14	1.2766 (4)	0.8827 (2)	0.32737 (18)	0.0604 (6)
H14	1.292238	0.950267	0.300041	0.072*
C15	1.4009 (4)	0.8035 (3)	0.3332 (2)	0.0662 (7)
H15	1.500980	0.815666	0.308877	0.079*
C16	1.3775 (4)	0.7031 (3)	0.3761 (2)	0.0671 (7)
H16	1.463862	0.649448	0.379133	0.080*
C17	0.1294 (4)	0.2803 (2)	0.41911 (17)	0.0567 (6)
C18	−0.0230 (4)	0.2228 (2)	0.4243 (2)	0.0644 (7)
H18	−0.015814	0.154010	0.452680	0.077*
C19	−0.1848 (4)	0.2662 (2)	0.3881 (2)	0.0681 (7)
H19	−0.285878	0.226660	0.391183	0.082*
C20	−0.1947 (4)	0.3694 (2)	0.34706 (19)	0.0663 (7)
C21	−0.0454 (4)	0.4295 (2)	0.34266 (19)	0.0661 (7)
H21	−0.053490	0.499214	0.315895	0.079*
C22	0.1157 (4)	0.3847 (2)	0.37846 (19)	0.0626 (6)
H22	0.216388	0.424649	0.375408	0.075*
C23	0.3017 (4)	0.2337 (2)	0.45288 (18)	0.0607 (6)
H23	0.400830	0.275359	0.450152	0.073*
C24	0.5092 (4)	0.0001 (2)	0.56549 (17)	0.0564 (6)
C25	0.3786 (4)	−0.0730 (2)	0.57278 (19)	0.0637 (7)
H25	0.264350	−0.057283	0.545057	0.076*
C26	0.4168 (5)	−0.1719 (2)	0.6221 (2)	0.0712 (8)
H26	0.327195	−0.221627	0.625588	0.085*
C27	0.5824 (5)	−0.1965 (2)	0.6649 (2)	0.0715 (8)
H27	0.604432	−0.261624	0.698298	0.086*
C28	0.7202 (4)	−0.1232 (2)	0.65860 (17)	0.0605 (6)
C29	0.6849 (4)	−0.0234 (2)	0.60844 (17)	0.0552 (5)
C30	0.8961 (5)	−0.1427 (3)	0.6997 (2)	0.0747 (8)
H30	0.926770	−0.207020	0.733023	0.090*
C31	1.0200 (5)	−0.0667 (3)	0.6902 (2)	0.0787 (9)
H31	1.135851	−0.078429	0.717383	0.094*
C32	0.9717 (4)	0.0294 (3)	0.6392 (2)	0.0743 (8)
H32	1.058474	0.080213	0.633341	0.089*
N1	0.8201 (3)	0.60135 (18)	0.52172 (15)	0.0572 (5)
N2	0.9658 (3)	0.63652 (19)	0.49216 (18)	0.0624 (5)
H2A	1.058243	0.596165	0.501010	0.075*
N3	1.2389 (3)	0.68040 (19)	0.41259 (17)	0.0605 (5)
N4	0.3177 (3)	0.13565 (18)	0.48631 (16)	0.0623 (6)
N5	0.4832 (3)	0.0983 (2)	0.51623 (18)	0.0675 (6)
H5A	0.571013	0.135167	0.504734	0.081*
N6	0.8104 (3)	0.05199 (19)	0.59898 (17)	0.0640 (5)
Cl1	0.21942 (11)	0.30746 (7)	0.69220 (7)	0.0832 (2)
Cl2	−0.39863 (14)	0.42416 (8)	0.30136 (9)	0.0979 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0560 (13)	0.0488 (12)	0.0530 (12)	−0.0026 (10)	0.0094 (10)	0.0045 (9)
C2	0.0686 (15)	0.0453 (12)	0.0600 (14)	0.0001 (11)	0.0143 (11)	0.0092 (9)
C3	0.0610 (15)	0.0567 (14)	0.0608 (14)	0.0026 (11)	0.0143 (11)	0.0066 (11)
C4	0.0639 (15)	0.0548 (13)	0.0501 (12)	−0.0117 (11)	0.0136 (11)	0.0029 (9)
C5	0.0776 (18)	0.0491 (13)	0.0581 (14)	−0.0073 (12)	0.0105 (12)	0.0136 (10)
C6	0.0625 (15)	0.0524 (13)	0.0648 (15)	0.0005 (11)	0.0090 (12)	0.0129 (11)
C7	0.0596 (15)	0.0524 (13)	0.0632 (14)	−0.0019 (11)	0.0135 (11)	0.0082 (10)
C8	0.0555 (14)	0.0462 (12)	0.0503 (12)	−0.0053 (10)	0.0101 (10)	−0.0006 (9)
C9	0.0605 (14)	0.0515 (13)	0.0610 (14)	−0.0019 (11)	0.0202 (11)	−0.0030 (10)
C10	0.0706 (17)	0.0487 (13)	0.0676 (15)	0.0084 (11)	0.0155 (13)	−0.0005 (10)
C11	0.0727 (16)	0.0430 (12)	0.0621 (14)	−0.0048 (11)	0.0127 (12)	0.0028 (10)
C12	0.0610 (14)	0.0474 (12)	0.0456 (11)	−0.0083 (10)	0.0078 (9)	−0.0011 (9)
C13	0.0546 (13)	0.0469 (12)	0.0484 (12)	−0.0051 (9)	0.0077 (10)	−0.0007 (9)
C14	0.0684 (15)	0.0605 (14)	0.0527 (13)	−0.0159 (13)	0.0124 (11)	0.0020 (10)
C15	0.0547 (15)	0.0821 (19)	0.0638 (15)	−0.0067 (13)	0.0158 (12)	0.0069 (13)
C16	0.0567 (15)	0.0708 (17)	0.0758 (17)	0.0045 (13)	0.0179 (13)	0.0049 (13)
C17	0.0749 (17)	0.0454 (12)	0.0481 (12)	0.0036 (11)	0.0067 (11)	−0.0006 (9)
C18	0.0829 (19)	0.0427 (13)	0.0662 (15)	0.0005 (12)	0.0102 (13)	0.0057 (10)
C19	0.0748 (18)	0.0543 (15)	0.0740 (17)	−0.0041 (13)	0.0106 (13)	0.0027 (12)
C20	0.079 (2)	0.0544 (15)	0.0620 (15)	0.0071 (13)	0.0031 (13)	0.0003 (10)
C21	0.087 (2)	0.0464 (13)	0.0612 (15)	0.0036 (12)	0.0036 (14)	0.0082 (10)
C22	0.0792 (18)	0.0482 (13)	0.0591 (15)	−0.0013 (12)	0.0093 (13)	0.0046 (10)
C23	0.0736 (18)	0.0521 (14)	0.0551 (14)	0.0056 (12)	0.0080 (12)	0.0030 (10)
C24	0.0741 (16)	0.0428 (11)	0.0517 (13)	0.0056 (11)	0.0100 (11)	−0.0026 (9)
C25	0.0721 (18)	0.0552 (14)	0.0617 (16)	0.0007 (12)	0.0068 (12)	−0.0060 (11)
C26	0.089 (2)	0.0533 (15)	0.0721 (17)	−0.0082 (14)	0.0158 (15)	−0.0006 (12)
C27	0.101 (2)	0.0493 (14)	0.0635 (16)	0.0068 (14)	0.0133 (15)	0.0066 (11)
C28	0.0787 (18)	0.0517 (14)	0.0512 (13)	0.0118 (12)	0.0123 (12)	−0.0007 (9)
C29	0.0689 (15)	0.0465 (12)	0.0510 (12)	0.0071 (11)	0.0135 (11)	−0.0054 (9)
C30	0.089 (2)	0.0681 (18)	0.0650 (17)	0.0239 (17)	0.0098 (15)	0.0024 (13)
C31	0.0683 (19)	0.089 (2)	0.0777 (19)	0.0205 (16)	0.0097 (14)	−0.0059 (15)
C32	0.0682 (18)	0.0788 (19)	0.0770 (18)	0.0022 (15)	0.0164 (15)	−0.0103 (14)
N1	0.0635 (13)	0.0498 (11)	0.0611 (12)	−0.0068 (9)	0.0185 (10)	0.0047 (9)
N2	0.0595 (13)	0.0521 (11)	0.0799 (14)	0.0001 (10)	0.0241 (11)	0.0127 (10)
N3	0.0563 (12)	0.0565 (12)	0.0700 (13)	0.0016 (9)	0.0152 (10)	0.0064 (9)
N4	0.0725 (15)	0.0489 (11)	0.0620 (12)	0.0083 (10)	0.0031 (10)	0.0005 (9)
N5	0.0710 (15)	0.0531 (12)	0.0762 (15)	0.0058 (11)	0.0075 (12)	0.0118 (10)
N6	0.0693 (14)	0.0572 (12)	0.0667 (13)	0.0040 (10)	0.0154 (11)	−0.0046 (10)
Cl1	0.0837 (5)	0.0792 (5)	0.0940 (5)	−0.0197 (4)	0.0358 (4)	0.0109 (4)
Cl2	0.0834 (6)	0.0768 (5)	0.1236 (7)	0.0133 (4)	−0.0063 (5)	0.0136 (5)

Geometric parameters (Å, º)

C1—C6	1.393 (4)	C17—C23	1.458 (4)
C1—C2	1.399 (4)	C18—C19	1.381 (5)
C1—C7	1.467 (4)	C18—H18	0.9300
C2—C3	1.379 (4)	C19—C20	1.384 (4)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.384 (4)	C20—C21	1.384 (5)
C3—H3	0.9300	C20—Cl2	1.741 (3)
C4—C5	1.368 (4)	C21—C22	1.382 (4)
C4—Cl1	1.736 (3)	C21—H21	0.9300
C5—C6	1.390 (4)	C22—H22	0.9300
C5—H5	0.9300	C23—N4	1.283 (4)
C6—H6	0.9300	C23—H23	0.9300
C7—N1	1.281 (3)	C24—C25	1.367 (4)
C7—H7	0.9300	C24—N5	1.391 (3)
C8—C9	1.372 (4)	C24—C29	1.429 (4)
C8—N2	1.383 (3)	C25—C26	1.406 (4)
C8—C13	1.425 (3)	C25—H25	0.9300
C9—C10	1.407 (4)	C26—C27	1.363 (5)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.367 (4)	C27—C28	1.409 (5)
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.408 (4)	C28—C30	1.415 (5)
C11—H11	0.9300	C28—C29	1.419 (4)
C12—C14	1.408 (4)	C29—N6	1.363 (4)
C12—C13	1.421 (3)	C30—C31	1.359 (5)
C13—N3	1.362 (3)	C30—H30	0.9300
C14—C15	1.355 (4)	C31—C32	1.402 (5)
C14—H14	0.9300	C31—H31	0.9300
C15—C16	1.399 (4)	C32—N6	1.318 (4)
C15—H15	0.9300	C32—H32	0.9300
C16—N3	1.325 (4)	N1—N2	1.360 (3)
C16—H16	0.9300	N2—H2A	0.8600
C17—C18	1.391 (4)	N4—N5	1.363 (3)
C17—C22	1.395 (4)	N5—H5A	0.8600
C6—C1—C2	118.6 (2)	C17—C18—H18	119.4
C6—C1—C7	119.4 (2)	C18—C19—C20	119.1 (3)
C2—C1—C7	122.1 (2)	C18—C19—H19	120.4
C3—C2—C1	120.7 (2)	C20—C19—H19	120.4
C3—C2—H2	119.7	C21—C20—C19	121.0 (3)
C1—C2—H2	119.7	C21—C20—Cl2	119.8 (2)
C2—C3—C4	119.4 (3)	C19—C20—Cl2	119.2 (3)
C2—C3—H3	120.3	C22—C21—C20	119.3 (2)
C4—C3—H3	120.3	C22—C21—H21	120.4
C5—C4—C3	121.3 (2)	C20—C21—H21	120.4
C5—C4—Cl1	119.20 (19)	C21—C22—C17	120.9 (3)
C3—C4—Cl1	119.5 (2)	C21—C22—H22	119.6
C4—C5—C6	119.4 (2)	C17—C22—H22	119.6
C4—C5—H5	120.3	N4—C23—C17	120.6 (3)
C6—C5—H5	120.3	N4—C23—H23	119.7
C5—C6—C1	120.7 (3)	C17—C23—H23	119.7
C5—C6—H6	119.7	C25—C24—N5	123.7 (3)
C1—C6—H6	119.7	C25—C24—C29	120.2 (2)
N1—C7—C1	120.5 (3)	N5—C24—C29	116.1 (2)
N1—C7—H7	119.7	C24—C25—C26	120.1 (3)
C1—C7—H7	119.7	C24—C25—H25	119.9
C9—C8—N2	123.7 (2)	C26—C25—H25	119.9
C9—C8—C13	120.1 (2)	C27—C26—C25	121.4 (3)
N2—C8—C13	116.3 (2)	C27—C26—H26	119.3
C8—C9—C10	119.9 (2)	C25—C26—H26	119.3
C8—C9—H9	120.1	C26—C27—C28	120.0 (3)
C10—C9—H9	120.1	C26—C27—H27	120.0
C11—C10—C9	121.7 (3)	C28—C27—H27	120.0
C11—C10—H10	119.2	C27—C28—C30	123.9 (3)
C9—C10—H10	119.2	C27—C28—C29	119.6 (3)
C10—C11—C12	119.7 (2)	C30—C28—C29	116.6 (3)
C10—C11—H11	120.1	N6—C29—C28	123.3 (3)
C12—C11—H11	120.1	N6—C29—C24	117.9 (2)
C11—C12—C14	124.0 (2)	C28—C29—C24	118.7 (3)
C11—C12—C13	119.6 (2)	C31—C30—C28	119.6 (3)
C14—C12—C13	116.5 (2)	C31—C30—H30	120.2
N3—C13—C12	123.2 (2)	C28—C30—H30	120.2
N3—C13—C8	117.8 (2)	C30—C31—C32	119.4 (3)
C12—C13—C8	119.1 (2)	C30—C31—H31	120.3
C15—C14—C12	120.1 (2)	C32—C31—H31	120.3
C15—C14—H14	120.0	N6—C32—C31	123.8 (3)
C12—C14—H14	120.0	N6—C32—H32	118.1
C14—C15—C16	119.4 (3)	C31—C32—H32	118.1
C14—C15—H15	120.3	C7—N1—N2	116.2 (2)
C16—C15—H15	120.3	N1—N2—C8	120.1 (2)
N3—C16—C15	123.5 (3)	N1—N2—H2A	120.0
N3—C16—H16	118.3	C8—N2—H2A	120.0
C15—C16—H16	118.3	C16—N3—C13	117.4 (2)
C18—C17—C22	118.6 (3)	C23—N4—N5	116.9 (3)
C18—C17—C23	122.0 (2)	N4—N5—C24	119.5 (2)
C22—C17—C23	119.5 (3)	N4—N5—H5A	120.2
C19—C18—C17	121.1 (2)	C24—N5—H5A	120.2
C19—C18—H18	119.4	C32—N6—C29	117.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cl1^i	0.93	3.04	3.779 (3)	138
C30—H30···Cl2^ii	0.93	3.05	3.943 (3)	163

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