1-(Cyclo­heptyl­idene)thio­semicarbazide

The asymmetric unit of the title compound, C₈H₁₅N₃S, contains two independent mol­ecules. In both mol­ecules, the seven-membered cyclo­heptane ring adopts a chair conformation. An intra­molecular N—H...N hydrogen bond is observed in both mol­ecules, forming S(5) graph-set motifs. In the crystal, the two independent mol­ecules are connected through N—H...S hydrogen bonds, forming dimers which are in turn further connected by N—H...S hydrogen bonds into chains along [010].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1A      --C1A      .        5.6 s.u.
PLAT420_ALERT_2_C D-H Without Acceptor       N2A      --H2A      .     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          8 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          6 Report
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         28 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

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

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker 2004); cell refinement: SAINT (Bruker 2004); data reduction: SAINT (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

1-(Cycloheptylidene)thiosemicarbazide

Crystal data

C8H15N3S	F(000) = 800
Mr = 185.29	Dx = 1.236 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.7584 (8) Å	Cell parameters from 2990 reflections
b = 11.7060 (7) Å	θ = 3.9–27.0°
c = 13.3452 (8) Å	µ = 0.28 mm^−1
β = 92.273 (2)°	T = 298 K
V = 1991.5 (2) Å^3	Block, white
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection

Bruker Xcalibur Sapphire3 diffractometer	3912 independent reflections
Radiation source: fine-focus sealed tube	3464 reflections with I > 2σ(I)
Detector resolution: 6.1049 pixels mm^-1	Rint = 0.024
ω scans	θmax = 26.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→15
Tmin = 0.699, Tmax = 0.746	k = −14→14
33823 measured reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.6361P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
3912 reflections	Δρmax = 0.18 e Å^−3
217 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.

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

	x	y	z	Uiso*/Ueq
S1A	0.36226 (4)	0.06485 (3)	0.43363 (3)	0.05590 (14)
S1B	0.32888 (3)	0.37480 (3)	1.23730 (3)	0.05222 (13)
N3A	0.47697 (9)	0.25310 (10)	0.65467 (9)	0.0424 (3)
N2B	0.23843 (10)	0.27542 (10)	1.07986 (9)	0.0447 (3)
H2B	0.231543	0.342491	1.054142	0.054*
N2A	0.44552 (10)	0.15830 (10)	0.59824 (8)	0.0432 (3)
H2A	0.455647	0.090225	0.620829	0.052*
N1A	0.38303 (12)	0.28310 (11)	0.48068 (10)	0.0567 (4)
H1A1	0.402306	0.337464	0.520658	0.068*
H1A2	0.353446	0.298699	0.423286	0.068*
N3B	0.19979 (10)	0.18009 (10)	1.02925 (9)	0.0459 (3)
C7B	0.12387 (13)	0.30010 (14)	0.77541 (11)	0.0513 (4)
H7B1	0.054775	0.266491	0.765209	0.062*
H7B2	0.120771	0.377224	0.748874	0.062*
N1B	0.30030 (12)	0.15393 (11)	1.20019 (10)	0.0569 (4)
H1B1	0.278309	0.098724	1.162387	0.068*
H1B2	0.330900	0.139585	1.257387	0.068*
C1A	0.39882 (11)	0.17595 (12)	0.50737 (10)	0.0399 (3)
C2B	0.15849 (11)	0.19368 (12)	0.94109 (10)	0.0410 (3)
C3B	0.11911 (14)	0.08565 (13)	0.89161 (12)	0.0533 (4)
H3B1	0.049944	0.099577	0.861264	0.064*
H3B2	0.112277	0.027142	0.942404	0.064*
C4A	0.57595 (16)	0.11539 (15)	0.89648 (12)	0.0619 (5)
H4A1	0.586940	0.035946	0.914709	0.074*
H4A2	0.643974	0.152500	0.899257	0.074*
C8A	0.54954 (14)	0.34168 (14)	0.79911 (12)	0.0549 (4)
H8A1	0.542756	0.406431	0.753965	0.066*
H8A2	0.622996	0.335077	0.819960	0.066*
C7A	0.48644 (15)	0.36587 (16)	0.89122 (13)	0.0659 (5)
H7A1	0.492016	0.446633	0.906777	0.079*
H7A2	0.413189	0.349641	0.874849	0.079*
C2A	0.51753 (11)	0.23580 (12)	0.74279 (10)	0.0395 (3)
C1B	0.28711 (11)	0.26050 (12)	1.17047 (10)	0.0402 (3)
C5B	0.17991 (16)	0.10414 (16)	0.71256 (14)	0.0659 (5)
H5B1	0.109231	0.092553	0.684959	0.079*
H5B2	0.227671	0.069586	0.666594	0.079*
C4B	0.19057 (15)	0.04172 (15)	0.81164 (14)	0.0630 (5)
H4B1	0.262725	0.047682	0.836836	0.076*
H4B2	0.175657	−0.038576	0.800130	0.076*
C8B	0.15023 (12)	0.30606 (12)	0.88766 (11)	0.0443 (3)
H8B1	0.216397	0.346083	0.897653	0.053*
H8B2	0.096817	0.351409	0.918760	0.053*
C3A	0.53213 (14)	0.11999 (13)	0.78878 (11)	0.0506 (4)
H3A1	0.578569	0.076577	0.747354	0.061*
H3A2	0.464727	0.081536	0.786133	0.061*
C6B	0.20140 (15)	0.23161 (16)	0.71647 (13)	0.0619 (5)
H6B1	0.271208	0.243695	0.746025	0.074*
H6B2	0.200863	0.260753	0.648405	0.074*
C5A	0.50865 (18)	0.17020 (17)	0.97414 (13)	0.0726 (5)
H5A1	0.526310	0.136075	1.038862	0.087*
H5A2	0.435772	0.152300	0.957581	0.087*
C6A	0.51947 (16)	0.29866 (17)	0.98366 (13)	0.0650 (5)
H6A1	0.477872	0.324016	1.038739	0.078*
H6A2	0.592196	0.316471	1.001002	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0894 (3)	0.0358 (2)	0.0411 (2)	−0.00783 (18)	−0.01484 (19)	−0.00011 (15)
S1B	0.0670 (3)	0.0429 (2)	0.0457 (2)	−0.00184 (17)	−0.01074 (18)	−0.00288 (16)
N3A	0.0522 (7)	0.0365 (6)	0.0382 (6)	−0.0023 (5)	−0.0011 (5)	−0.0036 (5)
N2B	0.0599 (7)	0.0347 (6)	0.0388 (6)	0.0003 (5)	−0.0047 (5)	−0.0003 (5)
N2A	0.0606 (7)	0.0334 (6)	0.0351 (6)	0.0012 (5)	−0.0041 (5)	−0.0021 (5)
N1A	0.0874 (10)	0.0363 (6)	0.0451 (7)	0.0066 (6)	−0.0151 (7)	−0.0027 (5)
N3B	0.0592 (7)	0.0351 (6)	0.0429 (6)	−0.0019 (5)	−0.0027 (5)	−0.0015 (5)
C7B	0.0589 (9)	0.0437 (8)	0.0503 (8)	−0.0043 (7)	−0.0118 (7)	0.0072 (7)
N1B	0.0825 (10)	0.0411 (7)	0.0458 (7)	0.0054 (7)	−0.0131 (7)	0.0013 (6)
C1A	0.0468 (7)	0.0375 (7)	0.0355 (7)	0.0004 (6)	0.0023 (5)	−0.0010 (5)
C2B	0.0468 (7)	0.0352 (7)	0.0411 (7)	−0.0018 (6)	0.0018 (6)	−0.0016 (6)
C3B	0.0709 (10)	0.0354 (7)	0.0530 (9)	−0.0098 (7)	−0.0072 (8)	0.0003 (7)
C4A	0.0868 (12)	0.0516 (9)	0.0463 (9)	0.0098 (9)	−0.0095 (8)	0.0046 (7)
C8A	0.0733 (11)	0.0415 (8)	0.0488 (8)	−0.0128 (7)	−0.0122 (8)	−0.0004 (7)
C7A	0.0771 (12)	0.0584 (10)	0.0608 (10)	0.0140 (9)	−0.0154 (9)	−0.0240 (8)
C2A	0.0417 (7)	0.0388 (7)	0.0380 (7)	−0.0023 (6)	0.0020 (5)	−0.0028 (6)
C1B	0.0425 (7)	0.0407 (7)	0.0376 (7)	0.0034 (6)	0.0035 (5)	−0.0002 (6)
C5B	0.0755 (12)	0.0659 (11)	0.0566 (10)	−0.0118 (9)	0.0078 (9)	−0.0245 (9)
C4B	0.0680 (11)	0.0459 (9)	0.0738 (11)	0.0080 (8)	−0.0148 (9)	−0.0209 (8)
C8B	0.0537 (8)	0.0343 (7)	0.0449 (8)	−0.0003 (6)	0.0017 (6)	−0.0022 (6)
C3A	0.0690 (10)	0.0407 (8)	0.0417 (8)	0.0039 (7)	−0.0029 (7)	−0.0030 (6)
C6B	0.0734 (11)	0.0675 (11)	0.0453 (8)	−0.0214 (9)	0.0077 (8)	−0.0101 (8)
C5A	0.0998 (15)	0.0739 (13)	0.0446 (9)	−0.0177 (11)	0.0110 (9)	−0.0009 (9)
C6A	0.0768 (12)	0.0725 (12)	0.0460 (9)	−0.0025 (9)	0.0047 (8)	−0.0177 (8)

Geometric parameters (Å, º)

S1A—C1A	1.6855 (14)	C4A—H4A1	0.9700
S1B—C1B	1.6828 (14)	C4A—H4A2	0.9700
N3A—C2A	1.2820 (18)	C8A—C2A	1.4978 (19)
N3A—N2A	1.3913 (16)	C8A—C7A	1.522 (3)
N2B—C1B	1.3486 (18)	C8A—H8A1	0.9700
N2B—N3B	1.3850 (16)	C8A—H8A2	0.9700
N2B—H2B	0.8600	C7A—C6A	1.509 (3)
N2A—C1A	1.3456 (17)	C7A—H7A1	0.9700
N2A—H2A	0.8600	C7A—H7A2	0.9700
N1A—C1A	1.3173 (18)	C2A—C3A	1.497 (2)
N1A—H1A1	0.8600	C5B—C4B	1.512 (3)
N1A—H1A2	0.8600	C5B—C6B	1.518 (3)
N3B—C2B	1.2798 (18)	C5B—H5B1	0.9700
C7B—C6B	1.517 (2)	C5B—H5B2	0.9700
C7B—C8B	1.524 (2)	C4B—H4B1	0.9700
C7B—H7B1	0.9700	C4B—H4B2	0.9700
C7B—H7B2	0.9700	C8B—H8B1	0.9700
N1B—C1B	1.3178 (19)	C8B—H8B2	0.9700
N1B—H1B1	0.8600	C3A—H3A1	0.9700
N1B—H1B2	0.8600	C3A—H3A2	0.9700
C2B—C8B	1.4981 (19)	C6B—H6B1	0.9700
C2B—C3B	1.5038 (19)	C6B—H6B2	0.9700
C3B—C4B	1.521 (2)	C5A—C6A	1.515 (3)
C3B—H3B1	0.9700	C5A—H5A1	0.9700
C3B—H3B2	0.9700	C5A—H5A2	0.9700
C4A—C5A	1.515 (3)	C6A—H6A1	0.9700
C4A—C3A	1.522 (2)	C6A—H6A2	0.9700
C2A—N3A—N2A	117.89 (12)	H7A1—C7A—H7A2	107.5
C1B—N2B—N3B	118.37 (12)	N3A—C2A—C3A	123.94 (12)
C1B—N2B—H2B	120.8	N3A—C2A—C8A	114.94 (13)
N3B—N2B—H2B	120.8	C3A—C2A—C8A	121.12 (12)
C1A—N2A—N3A	118.25 (11)	N1B—C1B—N2B	116.18 (13)
C1A—N2A—H2A	120.9	N1B—C1B—S1B	124.00 (11)
N3A—N2A—H2A	120.9	N2B—C1B—S1B	119.81 (11)
C1A—N1A—H1A1	120.0	C4B—C5B—C6B	115.80 (14)
C1A—N1A—H1A2	120.0	C4B—C5B—H5B1	108.3
H1A1—N1A—H1A2	120.0	C6B—C5B—H5B1	108.3
C2B—N3B—N2B	118.27 (12)	C4B—C5B—H5B2	108.3
C6B—C7B—C8B	114.26 (13)	C6B—C5B—H5B2	108.3
C6B—C7B—H7B1	108.7	H5B1—C5B—H5B2	107.4
C8B—C7B—H7B1	108.7	C5B—C4B—C3B	114.50 (14)
C6B—C7B—H7B2	108.7	C5B—C4B—H4B1	108.6
C8B—C7B—H7B2	108.7	C3B—C4B—H4B1	108.6
H7B1—C7B—H7B2	107.6	C5B—C4B—H4B2	108.6
C1B—N1B—H1B1	120.0	C3B—C4B—H4B2	108.6
C1B—N1B—H1B2	120.0	H4B1—C4B—H4B2	107.6
H1B1—N1B—H1B2	120.0	C2B—C8B—C7B	115.87 (12)
N1A—C1A—N2A	116.57 (12)	C2B—C8B—H8B1	108.3
N1A—C1A—S1A	122.76 (11)	C7B—C8B—H8B1	108.3
N2A—C1A—S1A	120.67 (10)	C2B—C8B—H8B2	108.3
N3B—C2B—C8B	124.43 (13)	C7B—C8B—H8B2	108.3
N3B—C2B—C3B	114.67 (13)	H8B1—C8B—H8B2	107.4
C8B—C2B—C3B	120.89 (12)	C2A—C3A—C4A	117.02 (13)
C2B—C3B—C4B	113.17 (14)	C2A—C3A—H3A1	108.0
C2B—C3B—H3B1	108.9	C4A—C3A—H3A1	108.0
C4B—C3B—H3B1	108.9	C2A—C3A—H3A2	108.0
C2B—C3B—H3B2	108.9	C4A—C3A—H3A2	108.0
C4B—C3B—H3B2	108.9	H3A1—C3A—H3A2	107.3
H3B1—C3B—H3B2	107.8	C7B—C6B—C5B	114.63 (15)
C5A—C4A—C3A	115.73 (16)	C7B—C6B—H6B1	108.6
C5A—C4A—H4A1	108.3	C5B—C6B—H6B1	108.6
C3A—C4A—H4A1	108.3	C7B—C6B—H6B2	108.6
C5A—C4A—H4A2	108.3	C5B—C6B—H6B2	108.6
C3A—C4A—H4A2	108.3	H6B1—C6B—H6B2	107.6
H4A1—C4A—H4A2	107.4	C4A—C5A—C6A	115.19 (16)
C2A—C8A—C7A	114.62 (14)	C4A—C5A—H5A1	108.5
C2A—C8A—H8A1	108.6	C6A—C5A—H5A1	108.5
C7A—C8A—H8A1	108.6	C4A—C5A—H5A2	108.5
C2A—C8A—H8A2	108.6	C6A—C5A—H5A2	108.5
C7A—C8A—H8A2	108.6	H5A1—C5A—H5A2	107.5
H8A1—C8A—H8A2	107.6	C7A—C6A—C5A	115.30 (15)
C6A—C7A—C8A	115.06 (15)	C7A—C6A—H6A1	108.5
C6A—C7A—H7A1	108.5	C5A—C6A—H6A1	108.5
C8A—C7A—H7A1	108.5	C7A—C6A—H6A2	108.5
C6A—C7A—H7A2	108.5	C5A—C6A—H6A2	108.5
C8A—C7A—H7A2	108.5	H6A1—C6A—H6A2	107.5
C2A—N3A—N2A—C1A	177.23 (13)	N3B—N2B—C1B—S1B	−176.43 (10)
C1B—N2B—N3B—C2B	−176.42 (13)	C6B—C5B—C4B—C3B	58.8 (2)
N3A—N2A—C1A—N1A	−2.5 (2)	C2B—C3B—C4B—C5B	−78.37 (18)
N3A—N2A—C1A—S1A	178.06 (10)	N3B—C2B—C8B—C7B	165.36 (14)
N2B—N3B—C2B—C8B	0.9 (2)	C3B—C2B—C8B—C7B	−13.4 (2)
N2B—N3B—C2B—C3B	179.74 (13)	C6B—C7B—C8B—C2B	−58.26 (18)
N3B—C2B—C3B—C4B	−104.03 (16)	N3A—C2A—C3A—C4A	−176.63 (15)
C8B—C2B—C3B—C4B	74.84 (18)	C8A—C2A—C3A—C4A	2.8 (2)
C2A—C8A—C7A—C6A	80.50 (19)	C5A—C4A—C3A—C2A	62.9 (2)
N2A—N3A—C2A—C3A	−0.6 (2)	C8B—C7B—C6B—C5B	85.86 (19)
N2A—N3A—C2A—C8A	179.98 (12)	C4B—C5B—C6B—C7B	−65.3 (2)
C7A—C8A—C2A—N3A	113.48 (16)	C3A—C4A—C5A—C6A	−82.1 (2)
C7A—C8A—C2A—C3A	−66.0 (2)	C8A—C7A—C6A—C5A	−62.0 (2)
N3B—N2B—C1B—N1B	4.7 (2)	C4A—C5A—C6A—C7A	62.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A1···N3A	0.86	2.22	2.5943 (2)	106
N1B—H1B1···N3B	0.86	2.22	2.5904 (2)	106
N1A—H1A2···S1B^i	0.86	2.64	3.4642 (2)	160
N1B—H1B2···S1A^ii	0.86	2.53	3.3499 (2)	161
N2B—H2B···S1A^iii	0.86	2.87	3.6254 (2)	147

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