Completing the picture of tolaza­mide polymorphism under extreme conditions: a low-temperature study

We present the results of an experimental and computational study of structural changes in two polymorphs of tolaza­mide {systematic name: 1-[(azepan-1-yl­amino)­carbon­yl]-4-methyl­benzene­sulfonamide}, C₁₄H₂₁N₃O₃S, on cooling to 100 K and reverse heating. No phase transitions occurred in this temperature range. The anisotropy of the thermal expansion was different for the two polymorphs and differed from that reported previously for the hydro­static compression. The changes in different inter­molecular contacts responsible for the strain anisotropy were analysed. Relative shortening of the contacts was related directly to their initial length and reversely to the steric density around them. Increasing steric density is likely to be the driving force for the con­formational ordering of the azepane ring under compression.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015) for TZA_I_295, TZA_II_295, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100; CrysAlis PRO (Agilent, 2014) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for TZA_I_295, TZA_II_295, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100; CrysAlis PRO (Agilent, 2014) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for TZA_I_295, TZA_II_295, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100; CrysAlis PRO (Agilent, 2014) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for TZA_I_295, TZA_II_295; SHELXT (Sheldrick, 2015a) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100. For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009). Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009) for TZA_I_295; OLEX2 (Dolomanov et al., 2009) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100, TZA_II_295, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_295)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.336 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.3506 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2241 (9) Å	Cell parameters from 3538 reflections
c = 13.4984 (13) Å	θ = 2.3–24.0°
α = 79.091 (8)°	µ = 0.22 mm^−1
β = 87.215 (8)°	T = 295 K
γ = 85.815 (8)°	Block, colourless
V = 773.87 (13) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3157 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2134 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 1.5°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.912, Tmax = 1.000	l = −16→16
12448 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0469P)^2 + 0.175P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3157 reflections	Δρmax = 0.32 e Å^−3
218 parameters	Δρmin = −0.26 e Å^−3
2 restraints

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	Occ. (<1)
S1	0.02120 (10)	0.27197 (6)	0.22617 (5)	0.0525 (2)
O1	0.1381 (3)	0.15808 (18)	0.18513 (13)	0.0697 (5)
O2	−0.2030 (3)	0.27333 (19)	0.23401 (14)	0.0681 (5)
O3	−0.0662 (3)	0.45843 (17)	0.38256 (12)	0.0541 (4)
N1	0.1136 (4)	0.2549 (2)	0.33948 (15)	0.0535 (5)
H1	0.210 (4)	0.196 (3)	0.3526 (19)	0.052 (8)*
N2	0.1636 (4)	0.3207 (2)	0.49094 (16)	0.0556 (6)
H2	0.137 (4)	0.378 (3)	0.5288 (19)	0.055 (8)*
N3	0.3141 (3)	0.2000 (2)	0.51011 (14)	0.0520 (5)
C1	0.2067 (4)	0.7173 (3)	0.05245 (18)	0.0547 (6)
C2	0.3548 (4)	0.6027 (3)	0.0791 (2)	0.0672 (7)
H2A	0.4956	0.6170	0.0602	0.081*
C3	0.3020 (4)	0.4662 (3)	0.1333 (2)	0.0633 (7)
H3	0.4057	0.3902	0.1506	0.076*
C4	0.0939 (4)	0.4452 (2)	0.16108 (16)	0.0443 (5)
C5	−0.0569 (4)	0.5579 (3)	0.1357 (2)	0.0607 (7)
H5	−0.1976	0.5441	0.1551	0.073*
C6	0.0003 (4)	0.6929 (3)	0.0807 (2)	0.0640 (7)
H6	−0.1036	0.7684	0.0627	0.077*
C7	0.2679 (5)	0.8658 (3)	−0.0051 (2)	0.0802 (9)
H7A	0.4093	0.8564	−0.0326	0.120*
H7B	0.2606	0.9355	0.0397	0.120*
H7C	0.1725	0.8999	−0.0589	0.120*
C8	0.0612 (4)	0.3526 (2)	0.40410 (17)	0.0457 (6)
C9	0.5260 (4)	0.2532 (3)	0.5135 (2)	0.0666 (7)
H9AA	0.6275	0.1712	0.5076	0.080*	0.826 (6)
H9AB	0.5459	0.3284	0.4536	0.080*	0.826 (6)
H9BC	0.5966	0.2522	0.4482	0.080*	0.174 (6)
H9BD	0.5087	0.3555	0.5219	0.080*	0.174 (6)
C10A	0.5835 (5)	0.3148 (3)	0.6004 (2)	0.0624 (11)	0.826 (6)
H10A	0.4717	0.3865	0.6141	0.075*	0.826 (6)
H10B	0.7108	0.3673	0.5822	0.075*	0.826 (6)
C10B	0.6665 (17)	0.1744 (15)	0.5905 (5)	0.061 (5)	0.174 (6)
H10C	0.8096	0.2005	0.5704	0.074*	0.174 (6)
H10D	0.6616	0.0691	0.5918	0.074*	0.174 (6)
C11	0.6209 (5)	0.2021 (4)	0.6964 (2)	0.0847 (9)
H11A	0.7205	0.1248	0.6796	0.102*	0.826 (6)
H11B	0.6897	0.2506	0.7426	0.102*	0.826 (6)
H11C	0.7458	0.1696	0.7353	0.102*	0.174 (6)
H11D	0.5975	0.3080	0.6931	0.102*	0.174 (6)
C12	0.4373 (4)	0.1291 (4)	0.7522 (2)	0.0750 (8)
H12A	0.4100	0.1702	0.8130	0.090*
H12B	0.4793	0.0250	0.7734	0.090*
C13	0.2322 (4)	0.1397 (3)	0.69923 (19)	0.0604 (7)
H13A	0.1332	0.0795	0.7428	0.072*
H13B	0.1743	0.2414	0.6896	0.068 (8)*
C14	0.2479 (5)	0.0918 (3)	0.5987 (2)	0.0635 (7)
H14A	0.352 (4)	0.006 (3)	0.608 (2)	0.080 (9)*
H14B	0.109 (4)	0.062 (3)	0.5863 (19)	0.065 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0685 (4)	0.0432 (3)	0.0473 (4)	−0.0016 (3)	−0.0136 (3)	−0.0098 (3)
O1	0.1059 (15)	0.0490 (10)	0.0580 (11)	0.0109 (10)	−0.0181 (10)	−0.0219 (9)
O2	0.0626 (11)	0.0631 (11)	0.0773 (13)	−0.0158 (9)	−0.0156 (9)	−0.0020 (10)
O3	0.0624 (11)	0.0487 (9)	0.0485 (10)	0.0116 (8)	−0.0043 (8)	−0.0071 (8)
N1	0.0707 (15)	0.0443 (12)	0.0448 (12)	0.0121 (11)	−0.0122 (10)	−0.0098 (10)
N2	0.0750 (15)	0.0491 (12)	0.0427 (12)	0.0135 (11)	−0.0097 (11)	−0.0129 (10)
N3	0.0628 (13)	0.0450 (11)	0.0466 (12)	0.0074 (10)	−0.0106 (10)	−0.0069 (9)
C1	0.0659 (17)	0.0583 (15)	0.0410 (13)	−0.0107 (13)	−0.0091 (12)	−0.0076 (12)
C2	0.0502 (15)	0.0775 (19)	0.0725 (19)	−0.0101 (14)	0.0013 (13)	−0.0092 (16)
C3	0.0507 (16)	0.0614 (16)	0.0745 (18)	0.0110 (13)	−0.0073 (13)	−0.0082 (14)
C4	0.0517 (14)	0.0434 (12)	0.0386 (12)	0.0018 (11)	−0.0088 (10)	−0.0097 (10)
C5	0.0482 (14)	0.0607 (16)	0.0663 (17)	0.0026 (13)	−0.0041 (12)	0.0035 (13)
C6	0.0650 (18)	0.0538 (15)	0.0653 (17)	0.0077 (13)	−0.0055 (14)	0.0055 (13)
C7	0.103 (2)	0.0696 (19)	0.0662 (19)	−0.0273 (18)	−0.0117 (17)	0.0016 (15)
C8	0.0556 (14)	0.0407 (12)	0.0391 (13)	−0.0061 (11)	0.0017 (11)	−0.0030 (10)
C9	0.0669 (18)	0.0758 (18)	0.0544 (16)	−0.0037 (15)	0.0021 (13)	−0.0067 (14)
C10A	0.056 (2)	0.060 (2)	0.072 (2)	−0.0103 (16)	−0.0008 (16)	−0.0126 (17)
C10B	0.047 (9)	0.081 (12)	0.048 (9)	0.015 (8)	0.007 (7)	0.000 (8)
C11	0.0695 (19)	0.119 (3)	0.068 (2)	−0.0093 (19)	−0.0161 (16)	−0.0166 (19)
C12	0.0702 (19)	0.096 (2)	0.0536 (17)	0.0036 (16)	−0.0092 (14)	−0.0022 (16)
C13	0.0629 (16)	0.0559 (16)	0.0569 (16)	−0.0083 (13)	0.0042 (13)	0.0034 (13)
C14	0.078 (2)	0.0474 (15)	0.0642 (18)	−0.0132 (15)	−0.0135 (15)	−0.0028 (13)

Geometric parameters (Å, º)

S1—O1	1.4241 (18)	C9—H9AA	0.9700
S1—O2	1.4221 (18)	C9—H9AB	0.9700
S1—N1	1.640 (2)	C9—H9BC	0.9700
S1—C4	1.754 (2)	C9—H9BD	0.9700
O3—C8	1.222 (3)	C9—C10A	1.468 (4)
N1—H1	0.79 (2)	C9—C10B	1.454 (6)
N1—C8	1.382 (3)	C10A—H10A	0.9700
N2—H2	0.81 (2)	C10A—H10B	0.9700
N2—N3	1.407 (3)	C10A—C11	1.517 (4)
N2—C8	1.341 (3)	C10B—H10C	0.9700
N3—C9	1.471 (3)	C10B—H10D	0.9700
N3—C14	1.471 (3)	C10B—C11	1.511 (6)
C1—C2	1.369 (4)	C11—H11A	0.9700
C1—C6	1.370 (3)	C11—H11B	0.9700
C1—C7	1.508 (4)	C11—H11C	0.9700
C2—H2A	0.9300	C11—H11D	0.9700
C2—C3	1.387 (4)	C11—C12	1.489 (4)
C3—H3	0.9300	C12—H12A	0.9700
C3—C4	1.373 (3)	C12—H12B	0.9700
C4—C5	1.367 (3)	C12—C13	1.505 (4)
C5—H5	0.9300	C13—H13A	0.9700
C5—C6	1.386 (3)	C13—H13B	0.9700
C6—H6	0.9300	C13—C14	1.501 (4)
C7—H7A	0.9600	C14—H14A	0.99 (3)
C7—H7B	0.9600	C14—H14B	0.98 (3)
C7—H7C	0.9600
O1—S1—N1	103.56 (11)	C10A—C9—N3	120.1 (2)
O1—S1—C4	109.54 (11)	C10A—C9—H9AA	107.3
O2—S1—O1	119.57 (12)	C10A—C9—H9AB	107.3
O2—S1—N1	109.05 (12)	C10B—C9—N3	118.3 (6)
O2—S1—C4	108.78 (11)	C10B—C9—H9BC	107.7
N1—S1—C4	105.38 (11)	C10B—C9—H9BD	107.7
S1—N1—H1	116.1 (19)	C9—C10A—H10A	108.5
C8—N1—S1	124.20 (19)	C9—C10A—H10B	108.5
C8—N1—H1	118.6 (19)	C9—C10A—C11	115.1 (3)
N3—N2—H2	123.5 (19)	H10A—C10A—H10B	107.5
C8—N2—H2	115.1 (19)	C11—C10A—H10A	108.5
C8—N2—N3	121.3 (2)	C11—C10A—H10B	108.5
N2—N3—C9	110.09 (19)	C9—C10B—H10C	108.2
N2—N3—C14	110.7 (2)	C9—C10B—H10D	108.2
C14—N3—C9	115.6 (2)	C9—C10B—C11	116.3 (5)
C2—C1—C6	117.6 (2)	H10C—C10B—H10D	107.4
C2—C1—C7	121.5 (2)	C11—C10B—H10C	108.2
C6—C1—C7	120.9 (3)	C11—C10B—H10D	108.2
C1—C2—H2A	118.9	C10A—C11—H11A	107.6
C1—C2—C3	122.3 (2)	C10A—C11—H11B	107.6
C3—C2—H2A	118.9	C10B—C11—H11C	108.2
C2—C3—H3	120.6	C10B—C11—H11D	108.2
C4—C3—C2	118.8 (2)	H11A—C11—H11B	107.0
C4—C3—H3	120.6	H11C—C11—H11D	107.4
C3—C4—S1	119.85 (19)	C12—C11—C10A	119.1 (3)
C5—C4—S1	120.04 (18)	C12—C11—C10B	116.3 (6)
C5—C4—C3	120.1 (2)	C12—C11—H11A	107.6
C4—C5—H5	120.1	C12—C11—H11B	107.6
C4—C5—C6	119.8 (2)	C12—C11—H11C	108.2
C6—C5—H5	120.1	C12—C11—H11D	108.2
C1—C6—C5	121.4 (2)	C11—C12—H12A	107.7
C1—C6—H6	119.3	C11—C12—H12B	107.7
C5—C6—H6	119.3	C11—C12—C13	118.5 (2)
C1—C7—H7A	109.5	H12A—C12—H12B	107.1
C1—C7—H7B	109.5	C13—C12—H12A	107.7
C1—C7—H7C	109.5	C13—C12—H12B	107.7
H7A—C7—H7B	109.5	C12—C13—H13A	108.5
H7A—C7—H7C	109.5	C12—C13—H13B	108.5
H7B—C7—H7C	109.5	H13A—C13—H13B	107.5
O3—C8—N1	122.2 (2)	C14—C13—C12	115.1 (2)
O3—C8—N2	123.9 (2)	C14—C13—H13A	108.5
N2—C8—N1	113.9 (2)	C14—C13—H13B	108.5
N3—C9—H9AA	107.3	N3—C14—C13	117.8 (2)
N3—C9—H9AB	107.3	N3—C14—H14A	108.8 (16)
N3—C9—H9BC	107.7	N3—C14—H14B	107.8 (15)
N3—C9—H9BD	107.7	C13—C14—H14A	104.7 (17)
H9AA—C9—H9AB	106.9	C13—C14—H14B	107.1 (15)
H9BC—C9—H9BD	107.1	H14A—C14—H14B	111 (2)
S1—N1—C8—O3	2.6 (3)	C2—C3—C4—S1	178.0 (2)
S1—N1—C8—N2	−176.90 (17)	C2—C3—C4—C5	−0.3 (4)
S1—C4—C5—C6	−177.4 (2)	C3—C4—C5—C6	0.8 (4)
O1—S1—N1—C8	173.1 (2)	C4—S1—N1—C8	58.1 (2)
O1—S1—C4—C3	−40.0 (2)	C4—C5—C6—C1	−1.1 (4)
O1—S1—C4—C5	138.3 (2)	C6—C1—C2—C3	−0.4 (4)
O2—S1—N1—C8	−58.5 (2)	C7—C1—C2—C3	179.0 (2)
O2—S1—C4—C3	−172.3 (2)	C7—C1—C6—C5	−178.5 (2)
O2—S1—C4—C5	5.9 (2)	C8—N2—N3—C9	112.7 (2)
N1—S1—C4—C3	70.9 (2)	C8—N2—N3—C14	−118.3 (2)
N1—S1—C4—C5	−110.9 (2)	C9—N3—C14—C13	61.3 (3)
N2—N3—C9—C10A	73.1 (3)	C9—C10A—C11—C12	−71.0 (4)
N2—N3—C9—C10B	139.2 (4)	C9—C10B—C11—C12	75.4 (11)
N2—N3—C14—C13	−64.7 (3)	C10A—C11—C12—C13	15.2 (4)
N3—N2—C8—O3	−177.8 (2)	C10B—C11—C12—C13	−47.2 (5)
N3—N2—C8—N1	1.7 (3)	C11—C12—C13—C14	53.0 (4)
N3—C9—C10A—C11	73.3 (4)	C12—C13—C14—N3	−82.9 (3)
N3—C9—C10B—C11	−76.0 (11)	C14—N3—C9—C10A	−53.2 (3)
C1—C2—C3—C4	0.1 (4)	C14—N3—C9—C10B	12.8 (5)
C2—C1—C6—C5	1.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.81 (2)	2.11 (3)	2.912 (3)	175 (2)

Symmetry code: (i) −x, −y+1, −z+1.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_275)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.343 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.3453 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1929 (5) Å	Cell parameters from 3671 reflections
c = 13.4917 (7) Å	θ = 2.3–24.1°
α = 79.103 (5)°	µ = 0.22 mm^−1
β = 87.266 (4)°	T = 275 K
γ = 85.857 (5)°	Block, colourless
V = 770.32 (7) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3149 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2245 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 2.3°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.915, Tmax = 1.000	l = −16→16
12387 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0426P)^2 + 0.2182P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3149 reflections	Δρmax = 0.27 e Å^−3
218 parameters	Δρmin = −0.21 e Å^−3
2 restraints

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	Occ. (<1)
S1	0.02093 (10)	0.27106 (6)	0.22573 (4)	0.0475 (2)
O1	0.1389 (3)	0.15700 (18)	0.18456 (12)	0.0631 (5)
O2	−0.2033 (3)	0.27213 (19)	0.23364 (13)	0.0613 (5)
O3	−0.0672 (2)	0.45771 (17)	0.38254 (11)	0.0497 (4)
N1	0.1136 (4)	0.2539 (2)	0.33936 (14)	0.0483 (5)
H1	0.209 (4)	0.197 (3)	0.3532 (18)	0.045 (7)*
N2	0.1624 (3)	0.3204 (2)	0.49105 (15)	0.0505 (5)
H2	0.135 (4)	0.377 (3)	0.5321 (19)	0.059 (8)*
N3	0.3147 (3)	0.2001 (2)	0.51007 (13)	0.0470 (5)
C1	0.2058 (4)	0.7178 (3)	0.05262 (16)	0.0495 (6)
C2	0.3544 (4)	0.6027 (3)	0.0789 (2)	0.0605 (7)
H2A	0.4953	0.6171	0.0598	0.073*
C3	0.3020 (4)	0.4660 (3)	0.13291 (19)	0.0571 (6)
H3	0.4058	0.3898	0.1501	0.068*
C4	0.0938 (3)	0.4449 (2)	0.16077 (15)	0.0401 (5)
C5	−0.0580 (4)	0.5579 (3)	0.13584 (18)	0.0539 (6)
H5	−0.1987	0.5437	0.1556	0.065*
C6	−0.0013 (4)	0.6932 (3)	0.08114 (18)	0.0570 (6)
H6	−0.1054	0.7690	0.0633	0.068*
C7	0.2670 (5)	0.8665 (3)	−0.0046 (2)	0.0715 (8)
H7A	0.4069	0.8566	−0.0340	0.107*
H7B	0.2643	0.9356	0.0407	0.107*
H7C	0.1689	0.9023	−0.0571	0.107*
C8	0.0616 (3)	0.3523 (2)	0.40436 (16)	0.0413 (5)
C9	0.5267 (4)	0.2536 (3)	0.51312 (19)	0.0614 (7)
H9AA	0.5461	0.3290	0.4532	0.074*	0.823 (6)
H9AB	0.6283	0.1715	0.5071	0.074*	0.823 (6)
H9BC	0.5969	0.2528	0.4478	0.074*	0.177 (6)
H9BD	0.5095	0.3563	0.5217	0.074*	0.177 (6)
C10A	0.5847 (5)	0.3160 (3)	0.6003 (2)	0.0560 (10)	0.823 (6)
H10A	0.4727	0.3877	0.6143	0.067*	0.823 (6)
H10B	0.7118	0.3690	0.5820	0.067*	0.823 (6)
C10B	0.6676 (16)	0.1740 (14)	0.5903 (4)	0.063 (5)	0.177 (6)
H10C	0.8110	0.1997	0.5700	0.076*	0.177 (6)
H10D	0.6618	0.0685	0.5916	0.076*	0.177 (6)
C11	0.6231 (4)	0.2020 (4)	0.6965 (2)	0.0750 (8)
H11A	0.7213	0.1240	0.6792	0.090*	0.823 (6)
H11B	0.6937	0.2500	0.7426	0.090*	0.823 (6)
H11C	0.7482	0.1687	0.7353	0.090*	0.177 (6)
H11D	0.6010	0.3083	0.6932	0.090*	0.177 (6)
C12	0.4384 (4)	0.1297 (3)	0.75282 (19)	0.0671 (7)
H12A	0.4113	0.1717	0.8133	0.081*
H12B	0.4797	0.0252	0.7746	0.081*
C13	0.2326 (4)	0.1402 (3)	0.69950 (18)	0.0537 (6)
H13A	0.1332	0.0801	0.7431	0.064*
H13B	0.1750	0.2423	0.6894	0.068 (8)*
C14	0.2492 (5)	0.0911 (3)	0.5988 (2)	0.0578 (7)
H14A	0.352 (4)	0.006 (3)	0.6056 (19)	0.068 (8)*
H14B	0.115 (4)	0.063 (3)	0.5847 (18)	0.064 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0617 (4)	0.0393 (3)	0.0426 (3)	−0.0013 (3)	−0.0118 (3)	−0.0088 (3)
O1	0.0952 (13)	0.0441 (10)	0.0531 (10)	0.0097 (9)	−0.0157 (9)	−0.0193 (8)
O2	0.0571 (10)	0.0563 (11)	0.0694 (11)	−0.0149 (8)	−0.0139 (8)	−0.0018 (9)
O3	0.0576 (10)	0.0461 (10)	0.0430 (9)	0.0092 (8)	−0.0036 (7)	−0.0068 (7)
N1	0.0652 (13)	0.0387 (11)	0.0404 (11)	0.0097 (10)	−0.0130 (10)	−0.0080 (9)
N2	0.0681 (13)	0.0444 (12)	0.0390 (11)	0.0121 (10)	−0.0083 (9)	−0.0126 (9)
N3	0.0563 (12)	0.0408 (11)	0.0423 (11)	0.0068 (9)	−0.0081 (9)	−0.0062 (8)
C1	0.0609 (15)	0.0531 (15)	0.0362 (12)	−0.0105 (12)	−0.0075 (11)	−0.0084 (11)
C2	0.0443 (14)	0.0713 (19)	0.0650 (16)	−0.0115 (13)	0.0024 (12)	−0.0088 (14)
C3	0.0468 (14)	0.0542 (16)	0.0680 (17)	0.0077 (12)	−0.0052 (12)	−0.0090 (13)
C4	0.0453 (12)	0.0415 (12)	0.0339 (11)	0.0016 (10)	−0.0066 (9)	−0.0088 (9)
C5	0.0433 (13)	0.0533 (15)	0.0590 (15)	0.0033 (11)	−0.0030 (11)	0.0033 (12)
C6	0.0570 (15)	0.0462 (15)	0.0607 (16)	0.0094 (12)	−0.0055 (12)	0.0040 (12)
C7	0.091 (2)	0.0610 (18)	0.0608 (17)	−0.0212 (15)	−0.0116 (15)	0.0025 (14)
C8	0.0497 (13)	0.0362 (12)	0.0364 (12)	−0.0043 (10)	0.0010 (10)	−0.0026 (10)
C9	0.0626 (16)	0.0694 (18)	0.0494 (15)	−0.0041 (13)	0.0006 (12)	−0.0051 (13)
C10A	0.0498 (17)	0.054 (2)	0.066 (2)	−0.0104 (15)	0.0038 (14)	−0.0148 (16)
C10B	0.046 (8)	0.088 (13)	0.051 (9)	−0.009 (8)	0.007 (7)	−0.001 (8)
C11	0.0616 (17)	0.107 (2)	0.0581 (17)	−0.0091 (16)	−0.0131 (14)	−0.0149 (17)
C12	0.0651 (17)	0.084 (2)	0.0473 (15)	0.0035 (15)	−0.0063 (13)	−0.0026 (14)
C13	0.0550 (14)	0.0489 (15)	0.0523 (15)	−0.0070 (11)	0.0024 (11)	0.0033 (11)
C14	0.0723 (19)	0.0414 (15)	0.0593 (16)	−0.0095 (14)	−0.0142 (14)	−0.0026 (12)

Geometric parameters (Å, º)

S1—O1	1.4268 (17)	C9—H9AA	0.9700
S1—O2	1.4215 (17)	C9—H9AB	0.9700
S1—N1	1.644 (2)	C9—H9BC	0.9700
S1—C4	1.753 (2)	C9—H9BD	0.9700
O3—C8	1.222 (3)	C9—C10A	1.475 (4)
N1—H1	0.78 (2)	C9—C10B	1.458 (6)
N1—C8	1.388 (3)	C10A—H10A	0.9700
N2—H2	0.84 (3)	C10A—H10B	0.9700
N2—N3	1.409 (3)	C10A—C11	1.524 (4)
N2—C8	1.333 (3)	C10B—H10C	0.9700
N3—C9	1.470 (3)	C10B—H10D	0.9700
N3—C14	1.473 (3)	C10B—C11	1.514 (6)
C1—C2	1.371 (4)	C11—H11A	0.9700
C1—C6	1.374 (3)	C11—H11B	0.9700
C1—C7	1.506 (3)	C11—H11C	0.9700
C2—H2A	0.9300	C11—H11D	0.9700
C2—C3	1.382 (3)	C11—C12	1.493 (4)
C3—H3	0.9300	C12—H12A	0.9700
C3—C4	1.373 (3)	C12—H12B	0.9700
C4—C5	1.369 (3)	C12—C13	1.509 (3)
C5—H5	0.9300	C13—H13A	0.9700
C5—C6	1.384 (3)	C13—H13B	0.9700
C6—H6	0.9300	C13—C14	1.507 (4)
C7—H7A	0.9600	C14—H14A	0.98 (3)
C7—H7B	0.9600	C14—H14B	0.94 (3)
C7—H7C	0.9600
O1—S1—N1	103.49 (11)	H9BC—C9—H9BD	107.2
O1—S1—C4	109.34 (10)	C10A—C9—H9AA	107.3
O2—S1—O1	119.79 (11)	C10A—C9—H9AB	107.3
O2—S1—N1	108.96 (11)	C10B—C9—N3	118.0 (6)
O2—S1—C4	108.91 (10)	C10B—C9—H9BC	107.8
N1—S1—C4	105.35 (10)	C10B—C9—H9BD	107.8
S1—N1—H1	117.5 (18)	C9—C10A—H10A	108.6
C8—N1—S1	124.33 (18)	C9—C10A—H10B	108.6
C8—N1—H1	116.9 (18)	C9—C10A—C11	114.8 (2)
N3—N2—H2	121.8 (18)	H10A—C10A—H10B	107.6
C8—N2—H2	116.9 (18)	C11—C10A—H10A	108.6
C8—N2—N3	121.21 (19)	C11—C10A—H10B	108.6
N2—N3—C9	110.50 (18)	C9—C10B—H10C	108.2
N2—N3—C14	110.53 (19)	C9—C10B—H10D	108.2
C9—N3—C14	115.6 (2)	C9—C10B—C11	116.4 (5)
C2—C1—C6	117.7 (2)	H10C—C10B—H10D	107.3
C2—C1—C7	121.3 (2)	C11—C10B—H10C	108.2
C6—C1—C7	121.0 (2)	C11—C10B—H10D	108.2
C1—C2—H2A	118.9	C10A—C11—H11A	107.6
C1—C2—C3	122.2 (2)	C10A—C11—H11B	107.6
C3—C2—H2A	118.9	C10B—C11—H11C	108.2
C2—C3—H3	120.6	C10B—C11—H11D	108.2
C4—C3—C2	118.8 (2)	H11A—C11—H11B	107.0
C4—C3—H3	120.6	H11C—C11—H11D	107.3
C3—C4—S1	119.91 (18)	C12—C11—C10A	118.8 (2)
C5—C4—S1	119.75 (16)	C12—C11—C10B	116.5 (6)
C5—C4—C3	120.3 (2)	C12—C11—H11A	107.6
C4—C5—H5	120.2	C12—C11—H11B	107.6
C4—C5—C6	119.7 (2)	C12—C11—H11C	108.2
C6—C5—H5	120.2	C12—C11—H11D	108.2
C1—C6—C5	121.3 (2)	C11—C12—H12A	107.7
C1—C6—H6	119.4	C11—C12—H12B	107.7
C5—C6—H6	119.4	C11—C12—C13	118.4 (2)
C1—C7—H7A	109.5	H12A—C12—H12B	107.1
C1—C7—H7B	109.5	C13—C12—H12A	107.7
C1—C7—H7C	109.5	C13—C12—H12B	107.7
H7A—C7—H7B	109.5	C12—C13—H13A	108.5
H7A—C7—H7C	109.5	C12—C13—H13B	108.5
H7B—C7—H7C	109.5	H13A—C13—H13B	107.5
O3—C8—N1	121.7 (2)	C14—C13—C12	114.9 (2)
O3—C8—N2	124.1 (2)	C14—C13—H13A	108.5
N2—C8—N1	114.2 (2)	C14—C13—H13B	108.5
N3—C9—H9AA	107.3	N3—C14—C13	117.5 (2)
N3—C9—H9AB	107.3	N3—C14—H14A	107.8 (15)
N3—C9—H9BC	107.8	N3—C14—H14B	106.0 (16)
N3—C9—H9BD	107.8	C13—C14—H14A	106.7 (15)
N3—C9—C10A	120.0 (2)	C13—C14—H14B	108.3 (15)
H9AA—C9—H9AB	106.9	H14A—C14—H14B	110 (2)
S1—N1—C8—O3	3.3 (3)	C2—C3—C4—S1	177.93 (18)
S1—N1—C8—N2	−177.16 (16)	C2—C3—C4—C5	−0.4 (3)
S1—C4—C5—C6	−177.48 (18)	C3—C4—C5—C6	0.9 (3)
O1—S1—N1—C8	172.74 (19)	C4—S1—N1—C8	58.0 (2)
O1—S1—C4—C3	−39.6 (2)	C4—C5—C6—C1	−1.2 (4)
O1—S1—C4—C5	138.71 (19)	C6—C1—C2—C3	−0.5 (4)
O2—S1—N1—C8	−58.8 (2)	C7—C1—C2—C3	178.9 (2)
O2—S1—C4—C3	−172.24 (18)	C7—C1—C6—C5	−178.5 (2)
O2—S1—C4—C5	6.1 (2)	C8—N2—N3—C9	111.9 (2)
N1—S1—C4—C3	71.0 (2)	C8—N2—N3—C14	−118.9 (2)
N1—S1—C4—C5	−110.6 (2)	C9—N3—C14—C13	61.9 (3)
N2—N3—C9—C10A	73.1 (3)	C9—C10A—C11—C12	−71.8 (3)
N2—N3—C9—C10B	139.2 (4)	C9—C10B—C11—C12	75.2 (11)
N2—N3—C14—C13	−64.6 (3)	C10A—C11—C12—C13	16.1 (4)
N3—N2—C8—O3	−177.74 (19)	C10B—C11—C12—C13	−46.6 (5)
N3—N2—C8—N1	2.7 (3)	C11—C12—C13—C14	52.8 (3)
N3—C9—C10A—C11	73.4 (3)	C12—C13—C14—N3	−83.4 (3)
N3—C9—C10B—C11	−76.3 (11)	C14—N3—C9—C10A	−53.4 (3)
C1—C2—C3—C4	0.2 (4)	C14—N3—C9—C10B	12.8 (4)
C2—C1—C6—C5	1.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.84 (3)	2.08 (3)	2.911 (3)	172 (2)

Symmetry code: (i) −x, −y+1, −z+1.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_250)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.351 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.3346 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1641 (5) Å	Cell parameters from 4017 reflections
c = 13.4642 (7) Å	θ = 2.3–26.5°
α = 79.222 (4)°	µ = 0.23 mm^−1
β = 87.305 (4)°	T = 250 K
γ = 85.936 (4)°	Block, colourless
V = 765.43 (7) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3131 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2355 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 2.3°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.919, Tmax = 1.000	l = −16→16
12313 measured reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 0.1936P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3131 reflections	Δρmax = 0.30 e Å^−3
218 parameters	Δρmin = −0.22 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	Occ. (<1)
S1	0.02087 (9)	0.27000 (6)	0.22520 (4)	0.04136 (18)
O1	0.1394 (3)	0.15591 (17)	0.18364 (11)	0.0553 (4)
O2	−0.2039 (2)	0.27037 (17)	0.23306 (12)	0.0539 (4)
O3	−0.0680 (2)	0.45699 (16)	0.38256 (10)	0.0432 (4)
N1	0.1140 (3)	0.2527 (2)	0.33923 (13)	0.0429 (5)
H1	0.208 (4)	0.196 (3)	0.3532 (18)	0.048 (7)*
N2	0.1619 (3)	0.3197 (2)	0.49126 (14)	0.0450 (5)
H2	0.138 (3)	0.380 (3)	0.5300 (17)	0.049 (7)*
N3	0.3157 (3)	0.19975 (19)	0.51009 (13)	0.0426 (4)
C1	0.2052 (3)	0.7188 (2)	0.05231 (15)	0.0424 (5)
C2	0.3545 (4)	0.6032 (3)	0.07873 (18)	0.0516 (6)
H2A	0.4956	0.6180	0.0599	0.062*
C3	0.3022 (3)	0.4660 (3)	0.13218 (17)	0.0496 (6)
H3	0.4061	0.3894	0.1487	0.060*
C4	0.0934 (3)	0.4446 (2)	0.16062 (14)	0.0353 (5)
C5	−0.0600 (3)	0.5578 (3)	0.13592 (17)	0.0470 (5)
H5	−0.2007	0.5432	0.1557	0.056*
C6	−0.0030 (4)	0.6937 (3)	0.08124 (17)	0.0498 (6)
H6	−0.1073	0.7697	0.0637	0.060*
C7	0.2667 (4)	0.8675 (3)	−0.00456 (19)	0.0625 (7)
H7A	0.4063	0.8573	−0.0345	0.094*
H7B	0.2654	0.9364	0.0412	0.094*
H7C	0.1678	0.9039	−0.0567	0.094*
C8	0.0609 (3)	0.3512 (2)	0.40422 (14)	0.0369 (5)
C9	0.5277 (4)	0.2545 (3)	0.51281 (17)	0.0537 (6)
H9AA	0.5460	0.3308	0.4531	0.064*	0.834 (6)
H9AB	0.6302	0.1728	0.5061	0.064*	0.834 (6)
H9BC	0.5976	0.2555	0.4470	0.064*	0.166 (6)
H9BD	0.5108	0.3567	0.5231	0.064*	0.166 (6)
C10A	0.5858 (4)	0.3166 (3)	0.6007 (2)	0.0488 (9)	0.834 (6)
H10A	0.4727	0.3872	0.6156	0.059*	0.834 (6)
H10B	0.7122	0.3709	0.5825	0.059*	0.834 (6)
C10B	0.6675 (16)	0.1709 (14)	0.5897 (4)	0.056 (5)	0.166 (6)
H10C	0.8123	0.1928	0.5690	0.067*	0.166 (6)
H10D	0.6553	0.0656	0.5913	0.067*	0.166 (6)
C11	0.6267 (4)	0.2009 (3)	0.69647 (18)	0.0629 (7)
H11A	0.7223	0.1221	0.6780	0.075*	0.834 (6)
H11B	0.7008	0.2478	0.7423	0.075*	0.834 (6)
H11C	0.7524	0.1668	0.7348	0.075*	0.166 (6)
H11D	0.6069	0.3077	0.6928	0.075*	0.166 (6)
C12	0.4405 (4)	0.1301 (3)	0.75386 (18)	0.0573 (6)
H12A	0.4138	0.1741	0.8137	0.069*
H12B	0.4807	0.0255	0.7767	0.069*
C13	0.2340 (3)	0.1404 (3)	0.69991 (16)	0.0460 (5)
H13A	0.1339	0.0806	0.7435	0.055*
H13B	0.1766	0.2429	0.6895	0.050 (6)*
C14	0.2517 (5)	0.0903 (3)	0.59926 (18)	0.0511 (6)
H14A	0.357 (4)	0.003 (3)	0.6037 (17)	0.058 (7)*
H14B	0.121 (4)	0.061 (3)	0.5850 (17)	0.054 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0533 (3)	0.0342 (3)	0.0374 (3)	−0.0007 (2)	−0.0102 (2)	−0.0073 (2)
O1	0.0819 (11)	0.0393 (9)	0.0477 (9)	0.0081 (8)	−0.0126 (8)	−0.0175 (7)
O2	0.0507 (9)	0.0498 (10)	0.0604 (10)	−0.0131 (7)	−0.0115 (7)	−0.0021 (8)
O3	0.0509 (9)	0.0387 (9)	0.0383 (8)	0.0079 (7)	−0.0039 (6)	−0.0059 (7)
N1	0.0561 (12)	0.0368 (11)	0.0353 (10)	0.0080 (9)	−0.0099 (9)	−0.0070 (8)
N2	0.0611 (12)	0.0389 (11)	0.0354 (10)	0.0113 (9)	−0.0082 (9)	−0.0120 (9)
N3	0.0526 (11)	0.0368 (10)	0.0375 (10)	0.0052 (8)	−0.0082 (8)	−0.0060 (8)
C1	0.0522 (13)	0.0448 (13)	0.0316 (11)	−0.0082 (11)	−0.0059 (9)	−0.0078 (9)
C2	0.0394 (12)	0.0616 (16)	0.0538 (14)	−0.0090 (11)	0.0026 (10)	−0.0094 (12)
C3	0.0399 (12)	0.0478 (14)	0.0588 (14)	0.0073 (10)	−0.0046 (10)	−0.0067 (11)
C4	0.0412 (11)	0.0361 (11)	0.0289 (10)	0.0021 (9)	−0.0068 (8)	−0.0073 (8)
C5	0.0374 (11)	0.0472 (14)	0.0505 (13)	0.0014 (10)	−0.0021 (10)	0.0050 (11)
C6	0.0503 (13)	0.0412 (13)	0.0522 (14)	0.0068 (10)	−0.0056 (11)	0.0032 (11)
C7	0.0765 (17)	0.0551 (16)	0.0546 (15)	−0.0193 (13)	−0.0095 (13)	0.0003 (12)
C8	0.0455 (12)	0.0327 (11)	0.0315 (11)	−0.0050 (9)	0.0025 (9)	−0.0032 (9)
C9	0.0547 (14)	0.0592 (15)	0.0446 (13)	−0.0024 (12)	−0.0002 (11)	−0.0035 (11)
C10A	0.0448 (15)	0.0454 (18)	0.0573 (18)	−0.0085 (13)	0.0024 (13)	−0.0115 (13)
C10B	0.036 (8)	0.082 (12)	0.042 (8)	−0.003 (7)	0.001 (6)	0.005 (7)
C11	0.0522 (14)	0.087 (2)	0.0510 (15)	−0.0072 (13)	−0.0098 (11)	−0.0147 (14)
C12	0.0561 (14)	0.0677 (17)	0.0439 (14)	0.0052 (12)	−0.0061 (11)	−0.0020 (12)
C13	0.0481 (12)	0.0421 (13)	0.0436 (13)	−0.0053 (10)	0.0024 (10)	0.0029 (10)
C14	0.0640 (16)	0.0383 (14)	0.0508 (14)	−0.0103 (12)	−0.0135 (12)	−0.0018 (11)

Geometric parameters (Å, º)

S1—O1	1.4275 (16)	C9—H9AA	0.9700
S1—O2	1.4229 (16)	C9—H9AB	0.9700
S1—N1	1.6465 (19)	C9—H9BC	0.9700
S1—C4	1.753 (2)	C9—H9BD	0.9700
O3—C8	1.223 (2)	C9—C10A	1.477 (3)
N1—H1	0.77 (2)	C9—C10B	1.462 (6)
N1—C8	1.385 (3)	C10A—H10A	0.9700
N2—H2	0.83 (2)	C10A—H10B	0.9700
N2—N3	1.411 (2)	C10A—C11	1.528 (4)
N2—C8	1.336 (3)	C10B—H10C	0.9700
N3—C9	1.471 (3)	C10B—H10D	0.9700
N3—C14	1.475 (3)	C10B—C11	1.520 (6)
C1—C2	1.375 (3)	C11—H11A	0.9700
C1—C6	1.380 (3)	C11—H11B	0.9700
C1—C7	1.501 (3)	C11—H11C	0.9700
C2—H2A	0.9300	C11—H11D	0.9700
C2—C3	1.381 (3)	C11—C12	1.498 (3)
C3—H3	0.9300	C12—H12A	0.9700
C3—C4	1.377 (3)	C12—H12B	0.9700
C4—C5	1.374 (3)	C12—C13	1.515 (3)
C5—H5	0.9300	C13—H13A	0.9700
C5—C6	1.386 (3)	C13—H13B	0.9700
C6—H6	0.9300	C13—C14	1.507 (3)
C7—H7A	0.9600	C14—H14A	1.00 (3)
C7—H7B	0.9600	C14—H14B	0.92 (2)
C7—H7C	0.9600
O1—S1—N1	103.47 (10)	H9BC—C9—H9BD	107.3
O1—S1—C4	109.39 (10)	C10A—C9—H9AA	107.4
O2—S1—O1	119.69 (10)	C10A—C9—H9AB	107.4
O2—S1—N1	109.02 (10)	C10B—C9—N3	116.5 (6)
O2—S1—C4	108.96 (10)	C10B—C9—H9BC	108.2
N1—S1—C4	105.31 (9)	C10B—C9—H9BD	108.2
S1—N1—H1	117.8 (18)	C9—C10A—H10A	108.6
C8—N1—S1	124.03 (17)	C9—C10A—H10B	108.6
C8—N1—H1	117.0 (18)	C9—C10A—C11	114.6 (2)
N3—N2—H2	122.6 (16)	H10A—C10A—H10B	107.6
C8—N2—H2	115.9 (16)	C11—C10A—H10A	108.6
C8—N2—N3	121.16 (18)	C11—C10A—H10B	108.6
N2—N3—C9	110.60 (17)	C9—C10B—H10C	108.3
N2—N3—C14	110.56 (18)	C9—C10B—H10D	108.3
C9—N3—C14	115.49 (18)	C9—C10B—C11	116.0 (4)
C2—C1—C6	117.6 (2)	H10C—C10B—H10D	107.4
C2—C1—C7	121.2 (2)	C11—C10B—H10C	108.3
C6—C1—C7	121.2 (2)	C11—C10B—H10D	108.3
C1—C2—H2A	118.8	C10A—C11—H11A	107.7
C1—C2—C3	122.3 (2)	C10A—C11—H11B	107.7
C3—C2—H2A	118.8	C10B—C11—H11C	108.3
C2—C3—H3	120.6	C10B—C11—H11D	108.3
C4—C3—C2	118.8 (2)	H11A—C11—H11B	107.1
C4—C3—H3	120.6	H11C—C11—H11D	107.4
C3—C4—S1	119.86 (16)	C12—C11—C10A	118.2 (2)
C5—C4—S1	119.60 (15)	C12—C11—C10B	116.1 (6)
C5—C4—C3	120.5 (2)	C12—C11—H11A	107.7
C4—C5—H5	120.3	C12—C11—H11B	107.7
C4—C5—C6	119.39 (19)	C12—C11—H11C	108.3
C6—C5—H5	120.3	C12—C11—H11D	108.3
C1—C6—C5	121.4 (2)	C11—C12—H12A	107.8
C1—C6—H6	119.3	C11—C12—H12B	107.8
C5—C6—H6	119.3	C11—C12—C13	118.1 (2)
C1—C7—H7A	109.5	H12A—C12—H12B	107.1
C1—C7—H7B	109.5	C13—C12—H12A	107.8
C1—C7—H7C	109.5	C13—C12—H12B	107.8
H7A—C7—H7B	109.5	C12—C13—H13A	108.6
H7A—C7—H7C	109.5	C12—C13—H13B	108.6
H7B—C7—H7C	109.5	H13A—C13—H13B	107.6
O3—C8—N1	122.08 (19)	C14—C13—C12	114.7 (2)
O3—C8—N2	123.79 (19)	C14—C13—H13A	108.6
N2—C8—N1	114.12 (19)	C14—C13—H13B	108.6
N3—C9—H9AA	107.4	N3—C14—C13	117.40 (19)
N3—C9—H9AB	107.4	N3—C14—H14A	106.7 (13)
N3—C9—H9BC	108.2	N3—C14—H14B	105.7 (15)
N3—C9—H9BD	108.2	C13—C14—H14A	108.9 (14)
N3—C9—C10A	119.82 (19)	C13—C14—H14B	108.8 (14)
H9AA—C9—H9AB	106.9	H14A—C14—H14B	109 (2)
S1—N1—C8—O3	3.0 (3)	C2—C3—C4—S1	178.07 (17)
S1—N1—C8—N2	−177.16 (15)	C2—C3—C4—C5	0.2 (3)
S1—C4—C5—C6	−177.36 (17)	C3—C4—C5—C6	0.5 (3)
O1—S1—N1—C8	172.84 (17)	C4—S1—N1—C8	58.0 (2)
O1—S1—C4—C3	−39.22 (19)	C4—C5—C6—C1	−1.0 (3)
O1—S1—C4—C5	138.67 (17)	C6—C1—C2—C3	0.0 (3)
O2—S1—N1—C8	−58.76 (19)	C7—C1—C2—C3	179.1 (2)
O2—S1—C4—C3	−171.75 (16)	C7—C1—C6—C5	−178.4 (2)
O2—S1—C4—C5	6.1 (2)	C8—N2—N3—C9	111.5 (2)
N1—S1—C4—C3	71.41 (19)	C8—N2—N3—C14	−119.3 (2)
N1—S1—C4—C5	−110.70 (18)	C9—N3—C14—C13	62.4 (3)
N2—N3—C9—C10A	73.6 (3)	C9—C10A—C11—C12	−73.5 (3)
N2—N3—C9—C10B	140.4 (4)	C9—C10B—C11—C12	76.7 (10)
N2—N3—C14—C13	−64.2 (3)	C10A—C11—C12—C13	17.9 (4)
N3—N2—C8—O3	−177.22 (18)	C10B—C11—C12—C13	−45.7 (4)
N3—N2—C8—N1	3.0 (3)	C11—C12—C13—C14	52.0 (3)
N3—C9—C10A—C11	73.7 (3)	C12—C13—C14—N3	−84.2 (3)
N3—C9—C10B—C11	−78.8 (10)	C14—N3—C9—C10A	−52.9 (3)
C1—C2—C3—C4	−0.5 (3)	C14—N3—C9—C10B	13.9 (4)
C2—C1—C6—C5	0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.83 (2)	2.08 (2)	2.909 (2)	175 (2)

Symmetry code: (i) −x, −y+1, −z+1.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_225)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.360 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.3186 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1502 (8) Å	Cell parameters from 4337 reflections
c = 13.4244 (11) Å	θ = 2.3–27.4°
α = 79.314 (7)°	µ = 0.23 mm^−1
β = 87.303 (7)°	T = 225 K
γ = 85.948 (7)°	Block, colourless
V = 760.32 (11) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3111 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2425 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 2.3°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.926, Tmax = 1.000	l = −16→16
12225 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.035P)^2 + 0.266P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3111 reflections	Δρmax = 0.27 e Å^−3
218 parameters	Δρmin = −0.29 e Å^−3
2 restraints

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	Occ. (<1)
S1	0.02064 (8)	0.26910 (5)	0.22470 (4)	0.03595 (16)
O1	0.1400 (2)	0.15506 (16)	0.18281 (11)	0.0477 (4)
O2	−0.2046 (2)	0.26908 (16)	0.23244 (11)	0.0468 (4)
O3	−0.0693 (2)	0.45636 (15)	0.38274 (10)	0.0384 (3)
N1	0.1134 (3)	0.2518 (2)	0.33898 (13)	0.0371 (4)
H1	0.211 (3)	0.197 (3)	0.3521 (17)	0.041 (7)*
N2	0.1619 (3)	0.3191 (2)	0.49142 (13)	0.0403 (4)
H2	0.141 (3)	0.378 (2)	0.5305 (16)	0.039 (6)*
N3	0.3167 (3)	0.19950 (18)	0.50980 (12)	0.0376 (4)
C1	0.2042 (3)	0.7193 (2)	0.05232 (14)	0.0366 (5)
C2	0.3547 (3)	0.6034 (3)	0.07830 (17)	0.0454 (5)
H2A	0.4961	0.6183	0.0592	0.055*
C3	0.3022 (3)	0.4659 (2)	0.13183 (16)	0.0430 (5)
H3	0.4064	0.3894	0.1484	0.052*
C4	0.0927 (3)	0.4443 (2)	0.16025 (14)	0.0309 (4)
C5	−0.0612 (3)	0.5579 (2)	0.13603 (16)	0.0405 (5)
H5	−0.2021	0.5431	0.1562	0.049*
C6	−0.0052 (3)	0.6942 (2)	0.08150 (16)	0.0438 (5)
H6	−0.1099	0.7702	0.0642	0.053*
C7	0.2654 (4)	0.8690 (3)	−0.00424 (18)	0.0535 (6)
H7A	0.4035	0.8587	−0.0362	0.080*
H7B	0.2683	0.9367	0.0423	0.080*
H7C	0.1635	0.9071	−0.0550	0.080*
C8	0.0604 (3)	0.3506 (2)	0.40424 (14)	0.0318 (4)
C9	0.5286 (3)	0.2557 (3)	0.51235 (16)	0.0474 (5)
H9AA	0.5454	0.3329	0.4529	0.057*	0.838 (5)
H9AB	0.6322	0.1748	0.5048	0.057*	0.838 (5)
H9BC	0.5984	0.2575	0.4463	0.057*	0.162 (5)
H9BD	0.5107	0.3578	0.5232	0.057*	0.162 (5)
C10A	0.5872 (4)	0.3173 (3)	0.60146 (19)	0.0431 (8)	0.838 (5)
H10A	0.4734	0.3871	0.6172	0.052*	0.838 (5)
H10B	0.7133	0.3724	0.5834	0.052*	0.838 (5)
C10B	0.6699 (16)	0.1716 (14)	0.5894 (4)	0.053 (5)	0.162 (5)
H10C	0.8149	0.1941	0.5686	0.064*	0.162 (5)
H10D	0.6584	0.0662	0.5904	0.064*	0.162 (5)
C11	0.6298 (4)	0.2002 (3)	0.69633 (17)	0.0537 (6)
H11A	0.7234	0.1210	0.6766	0.064*	0.838 (5)
H11B	0.7067	0.2458	0.7422	0.064*	0.838 (5)
H11C	0.7559	0.1651	0.7345	0.064*	0.162 (5)
H11D	0.6115	0.3071	0.6932	0.064*	0.162 (5)
C12	0.4417 (3)	0.1300 (3)	0.75479 (16)	0.0494 (6)
H12A	0.4154	0.1750	0.8145	0.059*
H12B	0.4812	0.0253	0.7781	0.059*
C13	0.2353 (3)	0.1408 (2)	0.70054 (15)	0.0405 (5)
H13A	0.1786	0.2436	0.6897	0.049*
H13B	0.1343	0.0815	0.7442	0.050 (6)*
C14	0.2540 (4)	0.0894 (3)	0.59933 (17)	0.0455 (5)
H14A	0.359 (4)	0.004 (3)	0.6023 (17)	0.058 (7)*
H14B	0.120 (4)	0.059 (2)	0.5849 (16)	0.047 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0461 (3)	0.0299 (3)	0.0325 (3)	−0.0010 (2)	−0.0089 (2)	−0.0061 (2)
O1	0.0707 (10)	0.0336 (8)	0.0411 (9)	0.0074 (7)	−0.0109 (7)	−0.0146 (7)
O2	0.0445 (8)	0.0437 (9)	0.0517 (9)	−0.0103 (7)	−0.0102 (7)	−0.0023 (7)
O3	0.0447 (8)	0.0350 (8)	0.0341 (8)	0.0062 (7)	−0.0026 (6)	−0.0054 (6)
N1	0.0480 (11)	0.0318 (10)	0.0307 (9)	0.0076 (8)	−0.0087 (8)	−0.0059 (7)
N2	0.0552 (11)	0.0343 (10)	0.0319 (10)	0.0106 (8)	−0.0086 (8)	−0.0107 (8)
N3	0.0455 (10)	0.0333 (9)	0.0329 (9)	0.0053 (8)	−0.0084 (7)	−0.0048 (7)
C1	0.0451 (12)	0.0396 (12)	0.0265 (10)	−0.0072 (10)	−0.0052 (9)	−0.0069 (9)
C2	0.0332 (11)	0.0538 (14)	0.0490 (13)	−0.0068 (10)	0.0014 (9)	−0.0077 (11)
C3	0.0364 (11)	0.0410 (13)	0.0496 (13)	0.0071 (9)	−0.0048 (9)	−0.0059 (10)
C4	0.0362 (10)	0.0307 (10)	0.0261 (9)	0.0008 (8)	−0.0042 (8)	−0.0068 (8)
C5	0.0322 (10)	0.0399 (12)	0.0449 (12)	0.0025 (9)	−0.0009 (9)	0.0025 (10)
C6	0.0425 (12)	0.0381 (12)	0.0456 (13)	0.0076 (10)	−0.0042 (10)	0.0025 (10)
C7	0.0641 (15)	0.0484 (14)	0.0470 (14)	−0.0156 (12)	−0.0085 (11)	0.0001 (11)
C8	0.0378 (11)	0.0283 (10)	0.0285 (10)	−0.0052 (9)	0.0023 (8)	−0.0030 (8)
C9	0.0494 (13)	0.0515 (14)	0.0389 (12)	−0.0016 (11)	−0.0014 (10)	−0.0025 (10)
C10A	0.0383 (14)	0.0412 (16)	0.0514 (17)	−0.0083 (11)	0.0035 (12)	−0.0112 (12)
C10B	0.033 (7)	0.072 (11)	0.049 (9)	0.000 (7)	0.003 (6)	0.004 (8)
C11	0.0442 (13)	0.0742 (17)	0.0439 (13)	−0.0045 (12)	−0.0104 (10)	−0.0118 (12)
C12	0.0490 (13)	0.0605 (15)	0.0354 (12)	0.0039 (11)	−0.0045 (10)	−0.0018 (11)
C13	0.0417 (11)	0.0388 (12)	0.0372 (11)	−0.0054 (9)	0.0016 (9)	0.0035 (9)
C14	0.0561 (15)	0.0336 (12)	0.0472 (13)	−0.0075 (11)	−0.0116 (11)	−0.0040 (10)

Geometric parameters (Å, º)

S1—O1	1.4283 (15)	C9—H9AA	0.9700
S1—O2	1.4218 (15)	C9—H9AB	0.9700
S1—N1	1.6442 (18)	C9—H9BC	0.9700
S1—C4	1.7542 (19)	C9—H9BD	0.9700
O3—C8	1.224 (2)	C9—C10A	1.486 (3)
N1—H1	0.77 (2)	C9—C10B	1.467 (6)
N1—C8	1.386 (3)	C10A—H10A	0.9700
N2—H2	0.82 (2)	C10A—H10B	0.9700
N2—N3	1.409 (2)	C10A—C11	1.526 (3)
N2—C8	1.335 (3)	C10B—H10C	0.9700
N3—C9	1.472 (3)	C10B—H10D	0.9700
N3—C14	1.476 (3)	C10B—C11	1.513 (6)
C1—C2	1.379 (3)	C11—H11A	0.9700
C1—C6	1.385 (3)	C11—H11B	0.9700
C1—C7	1.504 (3)	C11—H11C	0.9700
C2—H2A	0.9300	C11—H11D	0.9700
C2—C3	1.382 (3)	C11—C12	1.508 (3)
C3—H3	0.9300	C12—H12A	0.9700
C3—C4	1.378 (3)	C12—H12B	0.9700
C4—C5	1.376 (3)	C12—C13	1.512 (3)
C5—H5	0.9300	C13—H13A	0.9700
C5—C6	1.385 (3)	C13—H13B	0.9700
C6—H6	0.9300	C13—C14	1.515 (3)
C7—H7A	0.9600	C14—H14A	0.98 (3)
C7—H7B	0.9600	C14—H14B	0.95 (2)
C7—H7C	0.9600
O1—S1—N1	103.50 (9)	H9BC—C9—H9BD	107.4
O1—S1—C4	109.43 (9)	C10A—C9—H9AA	107.4
O2—S1—O1	119.67 (9)	C10A—C9—H9AB	107.4
O2—S1—N1	109.00 (9)	C10B—C9—N3	116.2 (6)
O2—S1—C4	108.91 (9)	C10B—C9—H9BC	108.2
N1—S1—C4	105.34 (9)	C10B—C9—H9BD	108.2
S1—N1—H1	117.6 (17)	C9—C10A—H10A	108.7
C8—N1—S1	124.09 (15)	C9—C10A—H10B	108.7
C8—N1—H1	116.6 (17)	C9—C10A—C11	114.4 (2)
N3—N2—H2	121.4 (15)	H10A—C10A—H10B	107.6
C8—N2—H2	117.1 (15)	C11—C10A—H10A	108.7
C8—N2—N3	121.12 (17)	C11—C10A—H10B	108.7
N2—N3—C9	110.35 (16)	C9—C10B—H10C	108.2
N2—N3—C14	110.62 (17)	C9—C10B—H10D	108.2
C9—N3—C14	115.46 (17)	C9—C10B—C11	116.2 (4)
C2—C1—C6	117.79 (19)	H10C—C10B—H10D	107.4
C2—C1—C7	121.25 (19)	C11—C10B—H10C	108.2
C6—C1—C7	121.0 (2)	C11—C10B—H10D	108.2
C1—C2—H2A	118.9	C10A—C11—H11A	107.8
C1—C2—C3	122.12 (19)	C10A—C11—H11B	107.8
C3—C2—H2A	118.9	C10B—C11—H11C	108.1
C2—C3—H3	120.6	C10B—C11—H11D	108.1
C4—C3—C2	118.86 (19)	H11A—C11—H11B	107.2
C4—C3—H3	120.6	H11C—C11—H11D	107.3
C3—C4—S1	119.76 (15)	C12—C11—C10A	117.89 (19)
C5—C4—S1	119.73 (14)	C12—C11—C10B	116.7 (6)
C5—C4—C3	120.48 (18)	C12—C11—H11A	107.8
C4—C5—H5	120.2	C12—C11—H11B	107.8
C4—C5—C6	119.66 (18)	C12—C11—H11C	108.1
C6—C5—H5	120.2	C12—C11—H11D	108.1
C1—C6—H6	119.5	C11—C12—H12A	107.9
C5—C6—C1	121.08 (19)	C11—C12—H12B	107.9
C5—C6—H6	119.5	C11—C12—C13	117.71 (18)
C1—C7—H7A	109.5	H12A—C12—H12B	107.2
C1—C7—H7B	109.5	C13—C12—H12A	107.9
C1—C7—H7C	109.5	C13—C12—H12B	107.9
H7A—C7—H7B	109.5	C12—C13—H13A	108.6
H7A—C7—H7C	109.5	C12—C13—H13B	108.6
H7B—C7—H7C	109.5	C12—C13—C14	114.55 (19)
O3—C8—N1	122.08 (18)	H13A—C13—H13B	107.6
O3—C8—N2	123.83 (18)	C14—C13—H13A	108.6
N2—C8—N1	114.09 (18)	C14—C13—H13B	108.6
N3—C9—H9AA	107.4	N3—C14—C13	117.15 (17)
N3—C9—H9AB	107.4	N3—C14—H14A	106.1 (14)
N3—C9—H9BC	108.2	N3—C14—H14B	105.8 (13)
N3—C9—H9BD	108.2	C13—C14—H14A	110.1 (14)
N3—C9—C10A	119.81 (18)	C13—C14—H14B	108.7 (13)
H9AA—C9—H9AB	106.9	H14A—C14—H14B	108.6 (19)
S1—N1—C8—O3	3.4 (3)	C2—C3—C4—S1	177.97 (16)
S1—N1—C8—N2	−176.96 (14)	C2—C3—C4—C5	−0.3 (3)
S1—C4—C5—C6	−177.35 (16)	C3—C4—C5—C6	0.9 (3)
O1—S1—N1—C8	172.54 (16)	C4—S1—N1—C8	57.67 (18)
O1—S1—C4—C3	−39.22 (18)	C4—C5—C6—C1	−1.2 (3)
O1—S1—C4—C5	139.02 (16)	C6—C1—C2—C3	−0.1 (3)
O2—S1—N1—C8	−59.07 (18)	C7—C1—C2—C3	178.82 (19)
O2—S1—C4—C3	−171.72 (16)	C7—C1—C6—C5	−178.2 (2)
O2—S1—C4—C5	6.52 (19)	C8—N2—N3—C9	111.5 (2)
N1—S1—C4—C3	71.48 (18)	C8—N2—N3—C14	−119.5 (2)
N1—S1—C4—C5	−110.28 (17)	C9—N3—C14—C13	62.5 (3)
N2—N3—C9—C10A	74.0 (2)	C9—C10A—C11—C12	−74.8 (3)
N2—N3—C9—C10B	140.6 (4)	C9—C10B—C11—C12	75.9 (10)
N2—N3—C14—C13	−63.7 (2)	C10A—C11—C12—C13	19.2 (3)
N3—N2—C8—O3	−177.07 (17)	C10B—C11—C12—C13	−44.9 (4)
N3—N2—C8—N1	3.3 (3)	C11—C12—C13—C14	51.8 (3)
N3—C9—C10A—C11	73.5 (3)	C12—C13—C14—N3	−85.1 (3)
N3—C9—C10B—C11	−78.9 (10)	C14—N3—C9—C10A	−52.3 (3)
C1—C2—C3—C4	−0.1 (3)	C14—N3—C9—C10B	14.2 (4)
C2—C1—C6—C5	0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.82 (2)	2.09 (2)	2.906 (2)	174 (2)

Symmetry code: (i) −x, −y+1, −z+1.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_200)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.368 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.3064 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1298 (7) Å	Cell parameters from 4645 reflections
c = 13.3984 (11) Å	θ = 2.3–27.5°
α = 79.397 (7)°	µ = 0.23 mm^−1
β = 87.344 (7)°	T = 200 K
γ = 85.986 (6)°	Block, colourless
V = 755.95 (11) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3090 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2455 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 2.3°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.893, Tmax = 1.000	l = −16→16
12156 measured reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.035P)^2 + 0.314P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3090 reflections	Δρmax = 0.32 e Å^−3
218 parameters	Δρmin = −0.32 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	Occ. (<1)
S1	0.02035 (8)	0.26832 (5)	0.22422 (3)	0.03102 (15)
O1	0.1403 (2)	0.15420 (15)	0.18212 (10)	0.0416 (4)
O2	−0.2054 (2)	0.26795 (15)	0.23202 (11)	0.0408 (4)
O3	−0.0705 (2)	0.45561 (14)	0.38268 (9)	0.0333 (3)
N1	0.1133 (3)	0.25089 (19)	0.33872 (12)	0.0326 (4)
H1	0.211 (3)	0.195 (2)	0.3524 (16)	0.034 (6)*
N2	0.1613 (3)	0.31804 (19)	0.49204 (13)	0.0352 (4)
H2	0.141 (3)	0.376 (2)	0.5319 (16)	0.036 (6)*
N3	0.3181 (3)	0.19895 (18)	0.50988 (12)	0.0333 (4)
C1	0.2033 (3)	0.7202 (2)	0.05218 (13)	0.0313 (4)
C2	0.3546 (3)	0.6041 (2)	0.07783 (15)	0.0382 (5)
H2A	0.4961	0.6192	0.0586	0.046*
C3	0.3025 (3)	0.4661 (2)	0.13121 (15)	0.0374 (5)
H3	0.4070	0.3894	0.1474	0.045*
C4	0.0924 (3)	0.4444 (2)	0.16000 (13)	0.0270 (4)
C5	−0.0626 (3)	0.5580 (2)	0.13624 (15)	0.0362 (5)
H5	−0.2035	0.5431	0.1567	0.043*
C6	−0.0065 (3)	0.6948 (2)	0.08148 (15)	0.0372 (5)
H6	−0.1115	0.7708	0.0641	0.045*
C7	0.2648 (4)	0.8701 (2)	−0.00409 (16)	0.0458 (5)
H7A	0.4045	0.8603	−0.0347	0.069*
H7B	0.2644	0.9384	0.0425	0.069*
H7C	0.1647	0.9073	−0.0560	0.069*
C8	0.0601 (3)	0.3498 (2)	0.40443 (13)	0.0287 (4)
C9	0.5296 (3)	0.2567 (2)	0.51205 (15)	0.0411 (5)
H9AA	0.5446	0.3347	0.4528	0.049*	0.854 (5)
H9AB	0.6343	0.1765	0.5036	0.049*	0.854 (5)
H9BC	0.5111	0.3585	0.5240	0.049*	0.146 (5)
H9BD	0.5990	0.2598	0.4456	0.049*	0.146 (5)
C10A	0.5886 (4)	0.3180 (3)	0.60185 (18)	0.0377 (7)	0.854 (5)
H10A	0.4741	0.3872	0.6182	0.045*	0.854 (5)
H10B	0.7143	0.3739	0.5839	0.045*	0.854 (5)
C10B	0.6716 (16)	0.1705 (13)	0.5890 (4)	0.042 (5)	0.146 (5)
H10C	0.8171	0.1918	0.5680	0.050*	0.146 (5)
H10D	0.6578	0.0651	0.5900	0.050*	0.146 (5)
C11	0.6327 (3)	0.1997 (3)	0.69638 (16)	0.0450 (5)
H11A	0.7244	0.1199	0.6758	0.054*	0.854 (5)
H11B	0.7122	0.2443	0.7421	0.054*	0.854 (5)
H11C	0.7592	0.1640	0.7343	0.054*	0.146 (5)
H11D	0.6157	0.3069	0.6931	0.054*	0.146 (5)
C12	0.4436 (3)	0.1305 (3)	0.75573 (15)	0.0426 (5)
H12A	0.4171	0.1772	0.8149	0.051*
H12B	0.4827	0.0258	0.7801	0.051*
C13	0.2367 (3)	0.1404 (2)	0.70079 (14)	0.0345 (5)
H13A	0.1355	0.0809	0.7444	0.041*
H13B	0.1794	0.2433	0.6897	0.041 (6)*
C14	0.2561 (4)	0.0885 (2)	0.59945 (16)	0.0391 (5)
H14A	0.361 (4)	0.004 (3)	0.6033 (17)	0.052 (7)*
H14B	0.121 (4)	0.054 (2)	0.5847 (16)	0.049 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0396 (3)	0.0255 (3)	0.0284 (3)	−0.0006 (2)	−0.0078 (2)	−0.00499 (19)
O1	0.0606 (9)	0.0301 (8)	0.0360 (8)	0.0061 (7)	−0.0098 (7)	−0.0125 (6)
O2	0.0395 (8)	0.0372 (8)	0.0452 (8)	−0.0093 (6)	−0.0079 (6)	−0.0022 (7)
O3	0.0382 (7)	0.0307 (7)	0.0295 (7)	0.0058 (6)	−0.0024 (6)	−0.0044 (6)
N1	0.0424 (10)	0.0283 (9)	0.0264 (9)	0.0076 (8)	−0.0085 (7)	−0.0045 (7)
N2	0.0495 (10)	0.0300 (9)	0.0268 (9)	0.0095 (8)	−0.0071 (8)	−0.0096 (8)
N3	0.0413 (9)	0.0285 (9)	0.0293 (9)	0.0058 (7)	−0.0082 (7)	−0.0040 (7)
C1	0.0389 (11)	0.0336 (11)	0.0227 (9)	−0.0052 (9)	−0.0042 (8)	−0.0061 (8)
C2	0.0290 (10)	0.0431 (12)	0.0418 (12)	−0.0046 (9)	0.0015 (9)	−0.0053 (10)
C3	0.0319 (10)	0.0362 (11)	0.0425 (12)	0.0064 (9)	−0.0030 (9)	−0.0053 (9)
C4	0.0328 (10)	0.0252 (9)	0.0229 (9)	0.0020 (8)	−0.0050 (7)	−0.0049 (7)
C5	0.0287 (10)	0.0375 (12)	0.0393 (11)	0.0013 (9)	−0.0017 (8)	0.0003 (9)
C6	0.0366 (11)	0.0325 (11)	0.0384 (11)	0.0073 (9)	−0.0039 (9)	0.0015 (9)
C7	0.0545 (13)	0.0407 (13)	0.0413 (12)	−0.0130 (11)	−0.0065 (10)	0.0003 (10)
C8	0.0334 (10)	0.0259 (10)	0.0261 (10)	−0.0058 (8)	0.0032 (8)	−0.0022 (8)
C9	0.0438 (12)	0.0433 (12)	0.0341 (11)	−0.0020 (10)	−0.0010 (9)	−0.0018 (9)
C10A	0.0346 (13)	0.0366 (15)	0.0431 (15)	−0.0066 (10)	0.0035 (10)	−0.0098 (11)
C10B	0.028 (7)	0.066 (11)	0.027 (8)	−0.009 (7)	−0.001 (6)	0.001 (7)
C11	0.0372 (11)	0.0600 (15)	0.0386 (12)	−0.0016 (10)	−0.0087 (9)	−0.0102 (11)
C12	0.0419 (12)	0.0520 (14)	0.0308 (11)	0.0047 (10)	−0.0034 (9)	−0.0016 (10)
C13	0.0351 (10)	0.0331 (11)	0.0320 (11)	−0.0044 (9)	0.0012 (8)	0.0026 (8)
C14	0.0506 (13)	0.0267 (11)	0.0397 (12)	−0.0059 (10)	−0.0123 (10)	−0.0010 (9)

Geometric parameters (Å, º)

S1—O1	1.4291 (14)	C9—H9AA	0.9700
S1—O2	1.4231 (14)	C9—H9AB	0.9700
S1—N1	1.6441 (17)	C9—H9BC	0.9700
S1—C4	1.7575 (19)	C9—H9BD	0.9700
O3—C8	1.226 (2)	C9—C10A	1.489 (3)
N1—H1	0.78 (2)	C9—C10B	1.474 (6)
N1—C8	1.388 (2)	C10A—H10A	0.9700
N2—H2	0.82 (2)	C10A—H10B	0.9700
N2—N3	1.412 (2)	C10A—C11	1.528 (3)
N2—C8	1.337 (2)	C10B—H10C	0.9700
N3—C9	1.472 (3)	C10B—H10D	0.9700
N3—C14	1.475 (3)	C10B—C11	1.516 (6)
C1—C2	1.381 (3)	C11—H11A	0.9700
C1—C6	1.385 (3)	C11—H11B	0.9700
C1—C7	1.503 (3)	C11—H11C	0.9700
C2—H2A	0.9300	C11—H11D	0.9700
C2—C3	1.382 (3)	C11—C12	1.512 (3)
C3—H3	0.9300	C12—H12A	0.9700
C3—C4	1.380 (3)	C12—H12B	0.9700
C4—C5	1.377 (3)	C12—C13	1.517 (3)
C5—H5	0.9300	C13—H13A	0.9700
C5—C6	1.387 (3)	C13—H13B	0.9700
C6—H6	0.9300	C13—C14	1.516 (3)
C7—H7A	0.9600	C14—H14A	0.97 (2)
C7—H7B	0.9600	C14—H14B	0.97 (2)
C7—H7C	0.9600
O1—S1—N1	103.45 (9)	H9AA—C9—H9AB	106.9
O1—S1—C4	109.48 (9)	H9BC—C9—H9BD	107.5
O2—S1—O1	119.71 (9)	C10A—C9—H9AA	107.4
O2—S1—N1	108.97 (9)	C10A—C9—H9AB	107.4
O2—S1—C4	108.95 (9)	C10B—C9—H9BC	108.4
N1—S1—C4	105.26 (8)	C10B—C9—H9BD	108.4
S1—N1—H1	117.7 (16)	C9—C10A—H10A	108.7
C8—N1—S1	124.13 (15)	C9—C10A—H10B	108.7
C8—N1—H1	116.7 (16)	C9—C10A—C11	114.25 (19)
N3—N2—H2	120.4 (15)	H10A—C10A—H10B	107.6
C8—N2—H2	118.1 (15)	C11—C10A—H10A	108.7
C8—N2—N3	120.97 (16)	C11—C10A—H10B	108.7
N2—N3—C9	110.30 (15)	C9—C10B—H10C	108.3
N2—N3—C14	110.32 (16)	C9—C10B—H10D	108.3
C9—N3—C14	115.72 (16)	C9—C10B—C11	115.9 (4)
C2—C1—C6	117.85 (18)	H10C—C10B—H10D	107.4
C2—C1—C7	121.05 (18)	C11—C10B—H10C	108.3
C6—C1—C7	121.09 (19)	C11—C10B—H10D	108.3
C1—C2—H2A	118.9	C10A—C11—H11A	107.9
C1—C2—C3	122.11 (18)	C10A—C11—H11B	107.9
C3—C2—H2A	118.9	C10B—C11—H11C	108.1
C2—C3—H3	120.6	C10B—C11—H11D	108.1
C4—C3—C2	118.75 (18)	H11A—C11—H11B	107.2
C4—C3—H3	120.6	H11C—C11—H11D	107.3
C3—C4—S1	119.70 (15)	C12—C11—C10A	117.59 (18)
C5—C4—S1	119.55 (14)	C12—C11—C10B	117.0 (5)
C5—C4—C3	120.71 (18)	C12—C11—H11A	107.9
C4—C5—H5	120.3	C12—C11—H11B	107.9
C4—C5—C6	119.41 (17)	C12—C11—H11C	108.1
C6—C5—H5	120.3	C12—C11—H11D	108.1
C1—C6—C5	121.15 (18)	C11—C12—H12A	108.0
C1—C6—H6	119.4	C11—C12—H12B	108.0
C5—C6—H6	119.4	C11—C12—C13	117.39 (17)
C1—C7—H7A	109.5	H12A—C12—H12B	107.2
C1—C7—H7B	109.5	C13—C12—H12A	108.0
C1—C7—H7C	109.5	C13—C12—H12B	108.0
H7A—C7—H7B	109.5	C12—C13—H13A	108.6
H7A—C7—H7C	109.5	C12—C13—H13B	108.6
H7B—C7—H7C	109.5	H13A—C13—H13B	107.6
O3—C8—N1	121.79 (17)	C14—C13—C12	114.69 (18)
O3—C8—N2	124.00 (17)	C14—C13—H13A	108.6
N2—C8—N1	114.21 (17)	C14—C13—H13B	108.6
N3—C9—H9AA	107.4	N3—C14—C13	117.02 (16)
N3—C9—H9AB	107.4	N3—C14—H14A	106.6 (13)
N3—C9—H9BC	108.4	N3—C14—H14B	106.4 (13)
N3—C9—H9BD	108.4	C13—C14—H14A	109.5 (13)
N3—C9—C10A	119.72 (17)	C13—C14—H14B	109.3 (13)
N3—C9—C10B	115.4 (6)	H14A—C14—H14B	107.6 (18)
S1—N1—C8—O3	3.5 (3)	C2—C3—C4—S1	177.89 (15)
S1—N1—C8—N2	−177.18 (14)	C2—C3—C4—C5	−0.1 (3)
S1—C4—C5—C6	−177.07 (15)	C3—C4—C5—C6	0.9 (3)
O1—S1—N1—C8	172.53 (15)	C4—S1—N1—C8	57.66 (17)
O1—S1—C4—C3	−38.82 (18)	C4—C5—C6—C1	−1.4 (3)
O1—S1—C4—C5	139.22 (15)	C6—C1—C2—C3	−0.2 (3)
O2—S1—N1—C8	−59.08 (17)	C7—C1—C2—C3	178.77 (18)
O2—S1—C4—C3	−171.45 (15)	C7—C1—C6—C5	−177.93 (18)
O2—S1—C4—C5	6.59 (18)	C8—N2—N3—C9	110.86 (19)
N1—S1—C4—C3	71.80 (17)	C8—N2—N3—C14	−120.05 (18)
N1—S1—C4—C5	−110.16 (16)	C9—N3—C14—C13	62.6 (2)
N2—N3—C9—C10A	74.4 (2)	C9—C10A—C11—C12	−75.9 (3)
N2—N3—C9—C10B	141.1 (3)	C9—C10B—C11—C12	76.3 (10)
N2—N3—C14—C13	−63.5 (2)	C10A—C11—C12—C13	20.7 (3)
N3—N2—C8—O3	−176.64 (16)	C10B—C11—C12—C13	−43.9 (4)
N3—N2—C8—N1	4.0 (2)	C11—C12—C13—C14	51.0 (3)
N3—C9—C10A—C11	73.2 (3)	C12—C13—C14—N3	−85.3 (2)
N3—C9—C10B—C11	−80.0 (9)	C14—N3—C9—C10A	−51.7 (3)
C1—C2—C3—C4	−0.3 (3)	C14—N3—C9—C10B	15.0 (4)
C2—C1—C6—C5	1.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.82 (2)	2.09 (2)	2.905 (2)	172 (2)

Symmetry code: (i) −x, −y+1, −z+1.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_175)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.380 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.2891 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0960 (4) Å	Cell parameters from 4856 reflections
c = 13.3659 (5) Å	θ = 2.3–28.2°
α = 79.436 (4)°	µ = 0.23 mm^−1
β = 87.381 (3)°	T = 175 K
γ = 86.026 (4)°	Block, colourless
V = 749.41 (6) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3064 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2504 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.851, Tmax = 1.000	l = −16→16
12090 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0373P)^2 + 0.3174P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3064 reflections	Δρmax = 0.33 e Å^−3
218 parameters	Δρmin = −0.35 e Å^−3
2 restraints

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	Occ. (<1)
S1	0.02002 (7)	0.26779 (5)	0.22385 (3)	0.02655 (14)
O1	0.1405 (2)	0.15383 (14)	0.18145 (10)	0.0354 (3)
O2	−0.2064 (2)	0.26729 (15)	0.23153 (10)	0.0345 (3)
O3	−0.07128 (19)	0.45497 (14)	0.38284 (9)	0.0285 (3)
N1	0.1134 (3)	0.24982 (18)	0.33884 (12)	0.0281 (4)
H1	0.211 (3)	0.197 (2)	0.3511 (16)	0.032 (6)*
N2	0.1607 (3)	0.31714 (18)	0.49256 (12)	0.0307 (4)
H2	0.141 (3)	0.380 (3)	0.5315 (16)	0.038 (6)*
N3	0.3190 (2)	0.19847 (17)	0.50973 (11)	0.0290 (4)
C1	0.2026 (3)	0.7208 (2)	0.05212 (13)	0.0270 (4)
C2	0.3549 (3)	0.6044 (2)	0.07748 (14)	0.0321 (4)
H2A	0.4967	0.6197	0.0581	0.038*
C3	0.3027 (3)	0.4658 (2)	0.13083 (15)	0.0315 (4)
H3	0.4074	0.3888	0.1470	0.038*
C4	0.0918 (3)	0.44428 (19)	0.15965 (13)	0.0232 (4)
C5	−0.0636 (3)	0.5583 (2)	0.13620 (14)	0.0303 (4)
H5	−0.2048	0.5431	0.1569	0.036*
C6	−0.0079 (3)	0.6953 (2)	0.08171 (14)	0.0321 (4)
H6	−0.1133	0.7716	0.0646	0.039*
C7	0.2633 (3)	0.8713 (2)	−0.00396 (15)	0.0385 (5)
H7A	0.4032	0.8618	−0.0349	0.058*
H7B	0.2632	0.9396	0.0429	0.058*
H7C	0.1625	0.9086	−0.0558	0.058*
C8	0.0594 (3)	0.34913 (19)	0.40446 (13)	0.0236 (4)
C9	0.5309 (3)	0.2571 (2)	0.51145 (15)	0.0356 (5)
H9AA	0.5451	0.3357	0.4522	0.043*	0.869 (5)
H9AB	0.6363	0.1771	0.5027	0.043*	0.869 (5)
H9BC	0.5126	0.3590	0.5241	0.043*	0.131 (5)
H9BD	0.6003	0.2607	0.4448	0.043*	0.131 (5)
C10A	0.5897 (3)	0.3186 (2)	0.60211 (17)	0.0318 (7)	0.869 (5)
H10A	0.4741	0.3871	0.6190	0.038*	0.869 (5)
H10B	0.7149	0.3757	0.5842	0.038*	0.869 (5)
C10B	0.6723 (16)	0.1684 (14)	0.5888 (4)	0.038 (5)	0.131 (5)
H10C	0.8189	0.1872	0.5675	0.045*	0.131 (5)
H10D	0.6546	0.0629	0.5902	0.045*	0.131 (5)
C11	0.6358 (3)	0.1992 (2)	0.69625 (15)	0.0376 (5)
H11A	0.7254	0.1187	0.6748	0.045*	0.869 (5)
H11B	0.7181	0.2431	0.7417	0.045*	0.869 (5)
H11C	0.6202	0.3069	0.6925	0.045*	0.131 (5)
H11D	0.7629	0.1631	0.7340	0.045*	0.131 (5)
C12	0.4453 (3)	0.1310 (2)	0.75679 (15)	0.0362 (5)
H12A	0.4838	0.0262	0.7824	0.043*
H12B	0.4187	0.1797	0.8153	0.043*
C13	0.2385 (3)	0.1403 (2)	0.70126 (14)	0.0297 (4)
H13A	0.1809	0.2435	0.6899	0.036*
H13B	0.1368	0.0807	0.7449	0.042 (6)*
C14	0.2586 (4)	0.0875 (2)	0.59955 (15)	0.0337 (5)
H14A	0.364 (3)	0.003 (3)	0.6040 (15)	0.038 (6)*
H14B	0.123 (3)	0.053 (2)	0.5850 (16)	0.041 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0336 (3)	0.0221 (2)	0.0243 (2)	−0.00045 (18)	−0.00668 (18)	−0.00444 (18)
O1	0.0525 (8)	0.0252 (7)	0.0300 (7)	0.0056 (6)	−0.0083 (6)	−0.0105 (6)
O2	0.0330 (7)	0.0309 (8)	0.0389 (8)	−0.0073 (6)	−0.0067 (6)	−0.0014 (6)
O3	0.0326 (7)	0.0265 (7)	0.0255 (7)	0.0047 (6)	−0.0019 (5)	−0.0047 (5)
N1	0.0353 (9)	0.0237 (9)	0.0246 (8)	0.0068 (7)	−0.0071 (7)	−0.0044 (7)
N2	0.0419 (9)	0.0265 (9)	0.0243 (8)	0.0081 (7)	−0.0060 (7)	−0.0088 (7)
N3	0.0352 (9)	0.0249 (8)	0.0261 (8)	0.0052 (7)	−0.0069 (7)	−0.0040 (6)
C1	0.0332 (10)	0.0294 (10)	0.0194 (9)	−0.0051 (8)	−0.0033 (7)	−0.0053 (7)
C2	0.0242 (9)	0.0377 (11)	0.0342 (11)	−0.0040 (8)	0.0021 (8)	−0.0064 (9)
C3	0.0270 (10)	0.0307 (11)	0.0359 (11)	0.0058 (8)	−0.0033 (8)	−0.0057 (9)
C4	0.0280 (9)	0.0227 (9)	0.0196 (8)	0.0005 (7)	−0.0045 (7)	−0.0053 (7)
C5	0.0231 (9)	0.0318 (11)	0.0330 (10)	0.0011 (8)	−0.0001 (8)	0.0005 (8)
C6	0.0306 (10)	0.0279 (10)	0.0343 (11)	0.0056 (8)	−0.0026 (8)	0.0012 (8)
C7	0.0456 (12)	0.0348 (12)	0.0345 (11)	−0.0106 (9)	−0.0045 (9)	−0.0007 (9)
C8	0.0276 (9)	0.0206 (9)	0.0222 (9)	−0.0030 (7)	0.0031 (7)	−0.0029 (7)
C9	0.0374 (11)	0.0377 (12)	0.0299 (10)	−0.0030 (9)	−0.0006 (8)	−0.0015 (9)
C10A	0.0287 (12)	0.0301 (13)	0.0376 (13)	−0.0047 (9)	0.0031 (9)	−0.0083 (10)
C10B	0.017 (7)	0.062 (12)	0.028 (8)	−0.006 (7)	−0.003 (6)	0.010 (7)
C11	0.0305 (10)	0.0497 (13)	0.0334 (11)	−0.0017 (9)	−0.0073 (8)	−0.0086 (10)
C12	0.0353 (11)	0.0448 (12)	0.0263 (10)	0.0038 (9)	−0.0031 (8)	−0.0028 (9)
C13	0.0296 (10)	0.0274 (10)	0.0290 (10)	−0.0035 (8)	0.0006 (8)	0.0030 (8)
C14	0.0424 (12)	0.0236 (10)	0.0357 (11)	−0.0050 (9)	−0.0096 (9)	−0.0037 (8)

Geometric parameters (Å, º)

S1—O1	1.4273 (14)	C9—H9AA	0.9700
S1—O2	1.4236 (13)	C9—H9AB	0.9700
S1—N1	1.6464 (16)	C9—H9BC	0.9700
S1—C4	1.7543 (18)	C9—H9BD	0.9700
O3—C8	1.223 (2)	C9—C10A	1.495 (3)
N1—H1	0.76 (2)	C9—C10B	1.480 (5)
N1—C8	1.386 (2)	C10A—H10A	0.9700
N2—H2	0.84 (2)	C10A—H10B	0.9700
N2—N3	1.411 (2)	C10A—C11	1.528 (3)
N2—C8	1.339 (2)	C10B—H10C	0.9700
N3—C9	1.472 (2)	C10B—H10D	0.9700
N3—C14	1.474 (2)	C10B—C11	1.517 (6)
C1—C2	1.382 (3)	C11—H11A	0.9700
C1—C6	1.387 (2)	C11—H11B	0.9700
C1—C7	1.500 (3)	C11—H11C	0.9700
C2—H2A	0.9300	C11—H11D	0.9700
C2—C3	1.382 (3)	C11—C12	1.519 (3)
C3—H3	0.9300	C12—H12A	0.9700
C3—C4	1.381 (2)	C12—H12B	0.9700
C4—C5	1.377 (3)	C12—C13	1.516 (3)
C5—H5	0.9300	C13—H13A	0.9700
C5—C6	1.383 (3)	C13—H13B	0.9700
C6—H6	0.9300	C13—C14	1.520 (3)
C7—H7A	0.9600	C14—H14A	0.98 (2)
C7—H7B	0.9600	C14—H14B	0.97 (2)
C7—H7C	0.9600
O1—S1—N1	103.40 (8)	H9AA—C9—H9AB	107.0
O1—S1—C4	109.33 (8)	H9BC—C9—H9BD	107.6
O2—S1—O1	119.78 (8)	C10A—C9—H9AA	107.5
O2—S1—N1	109.02 (8)	C10A—C9—H9AB	107.5
O2—S1—C4	108.88 (8)	C10B—C9—H9BC	108.7
N1—S1—C4	105.44 (8)	C10B—C9—H9BD	108.7
S1—N1—H1	117.2 (16)	C9—C10A—H10A	108.7
C8—N1—S1	123.79 (14)	C9—C10A—H10B	108.7
C8—N1—H1	117.2 (16)	C9—C10A—C11	114.09 (18)
N3—N2—H2	122.0 (15)	H10A—C10A—H10B	107.6
C8—N2—H2	116.4 (15)	C11—C10A—H10A	108.7
C8—N2—N3	120.74 (15)	C11—C10A—H10B	108.7
N2—N3—C9	110.48 (15)	C9—C10B—H10C	108.4
N2—N3—C14	110.16 (15)	C9—C10B—H10D	108.4
C9—N3—C14	115.63 (15)	C9—C10B—C11	115.7 (4)
C2—C1—C6	118.02 (17)	H10C—C10B—H10D	107.4
C2—C1—C7	121.11 (17)	C11—C10B—H10C	108.4
C6—C1—C7	120.86 (18)	C11—C10B—H10D	108.4
C1—C2—H2A	119.0	C10A—C11—H11A	108.0
C1—C2—C3	121.97 (17)	C10A—C11—H11B	108.0
C3—C2—H2A	119.0	C10B—C11—H11C	108.1
C2—C3—H3	120.7	C10B—C11—H11D	108.1
C4—C3—C2	118.60 (17)	C10B—C11—C12	116.8 (6)
C4—C3—H3	120.7	H11A—C11—H11B	107.3
C3—C4—S1	119.52 (14)	H11C—C11—H11D	107.3
C5—C4—S1	119.56 (13)	C12—C11—C10A	117.15 (17)
C5—C4—C3	120.89 (17)	C12—C11—H11A	108.0
C4—C5—H5	120.3	C12—C11—H11B	108.0
C4—C5—C6	119.47 (16)	C12—C11—H11C	108.1
C6—C5—H5	120.3	C12—C11—H11D	108.1
C1—C6—H6	119.5	C11—C12—H12A	108.1
C5—C6—C1	121.03 (17)	C11—C12—H12B	108.1
C5—C6—H6	119.5	H12A—C12—H12B	107.3
C1—C7—H7A	109.5	C13—C12—C11	116.96 (16)
C1—C7—H7B	109.5	C13—C12—H12A	108.1
C1—C7—H7C	109.5	C13—C12—H12B	108.1
H7A—C7—H7B	109.5	C12—C13—H13A	108.6
H7A—C7—H7C	109.5	C12—C13—H13B	108.6
H7B—C7—H7C	109.5	C12—C13—C14	114.85 (16)
O3—C8—N1	122.06 (16)	H13A—C13—H13B	107.5
O3—C8—N2	123.92 (16)	C14—C13—H13A	108.6
N2—C8—N1	114.02 (16)	C14—C13—H13B	108.6
N3—C9—H9AA	107.5	N3—C14—C13	116.92 (15)
N3—C9—H9AB	107.5	N3—C14—H14A	107.1 (12)
N3—C9—H9BC	108.7	N3—C14—H14B	106.2 (13)
N3—C9—H9BD	108.7	C13—C14—H14A	109.3 (12)
N3—C9—C10A	119.37 (16)	C13—C14—H14B	109.0 (12)
N3—C9—C10B	114.3 (6)	H14A—C14—H14B	107.9 (17)
S1—N1—C8—O3	3.5 (2)	C2—C3—C4—S1	177.97 (14)
S1—N1—C8—N2	−177.23 (13)	C2—C3—C4—C5	−0.2 (3)
S1—C4—C5—C6	−177.19 (14)	C3—C4—C5—C6	1.0 (3)
O1—S1—N1—C8	172.42 (15)	C4—S1—N1—C8	57.66 (17)
O1—S1—C4—C3	−38.80 (17)	C4—C5—C6—C1	−1.4 (3)
O1—S1—C4—C5	139.44 (14)	C6—C1—C2—C3	−0.1 (3)
O2—S1—N1—C8	−59.11 (17)	C7—C1—C2—C3	178.73 (17)
O2—S1—C4—C3	−171.35 (14)	C7—C1—C6—C5	−177.94 (17)
O2—S1—C4—C5	6.88 (17)	C8—N2—N3—C9	110.31 (18)
N1—S1—C4—C3	71.79 (16)	C8—N2—N3—C14	−120.71 (17)
N1—S1—C4—C5	−109.98 (15)	C9—N3—C14—C13	63.1 (2)
N2—N3—C9—C10A	74.3 (2)	C9—C10A—C11—C12	−77.4 (2)
N2—N3—C9—C10B	141.2 (3)	C9—C10B—C11—C12	77.2 (10)
N2—N3—C14—C13	−63.1 (2)	C10A—C11—C12—C13	22.3 (3)
N3—N2—C8—O3	−176.13 (16)	C10B—C11—C12—C13	−43.1 (4)
N3—N2—C8—N1	4.6 (2)	C11—C12—C13—C14	50.2 (2)
N3—C9—C10A—C11	73.5 (2)	C12—C13—C14—N3	−85.9 (2)
N3—C9—C10B—C11	−81.4 (10)	C14—N3—C9—C10A	−51.6 (2)
C1—C2—C3—C4	−0.2 (3)	C14—N3—C9—C10B	15.2 (4)
C2—C1—C6—C5	0.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.84 (2)	2.06 (2)	2.899 (2)	174 (2)

Symmetry code: (i) −x, −y+1, −z+1.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_150)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.388 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.2738 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0824 (4) Å	Cell parameters from 5119 reflections
c = 13.3414 (5) Å	θ = 2.3–28.8°
α = 79.449 (4)°	µ = 0.23 mm^−1
β = 87.415 (3)°	T = 150 K
γ = 86.013 (4)°	Block, colourless
V = 745.14 (6) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3045 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2540 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.927, Tmax = 1.000	l = −16→16
12009 measured reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0382P)^2 + 0.2704P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3045 reflections	Δρmax = 0.43 e Å^−3
218 parameters	Δρmin = −0.39 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	Occ. (<1)
S1	0.98036 (7)	0.73262 (5)	0.77641 (3)	0.02242 (13)
O1	0.8593 (2)	0.84664 (14)	0.81909 (9)	0.0297 (3)
O2	1.20715 (19)	0.73324 (14)	0.76890 (9)	0.0292 (3)
O3	1.07216 (18)	0.54545 (13)	0.61691 (9)	0.0242 (3)
N1	0.8871 (3)	0.75066 (17)	0.66118 (11)	0.0237 (3)
H1	0.790 (3)	0.805 (2)	0.6486 (16)	0.029 (6)*
N2	0.8400 (2)	0.68383 (17)	0.50685 (12)	0.0260 (3)
H2	0.859 (3)	0.623 (2)	0.4672 (16)	0.030 (5)*
N3	0.6802 (2)	0.80220 (16)	0.49024 (11)	0.0244 (3)
C1	0.7980 (3)	0.2788 (2)	0.94811 (12)	0.0228 (4)
C2	0.6452 (3)	0.3953 (2)	0.92270 (14)	0.0272 (4)
H2A	0.5031	0.3798	0.9420	0.033*
C3	0.6972 (3)	0.5341 (2)	0.86946 (14)	0.0262 (4)
H3	0.5923	0.6113	0.8535	0.031*
C4	0.9088 (3)	0.55568 (19)	0.84036 (12)	0.0200 (4)
C5	1.0651 (3)	0.4413 (2)	0.86356 (13)	0.0257 (4)
H5	1.2066	0.4564	0.8427	0.031*
C6	1.0091 (3)	0.3040 (2)	0.91813 (13)	0.0267 (4)
H6	1.1146	0.2274	0.9350	0.032*
C7	0.7372 (3)	0.1277 (2)	1.00388 (14)	0.0322 (4)
H7A	0.5978	0.1373	1.0357	0.048*
H7B	0.8394	0.0894	1.0551	0.048*
H7C	0.7354	0.0600	0.9565	0.048*
C8	0.9412 (3)	0.65192 (18)	0.59529 (12)	0.0201 (4)
C9	0.4679 (3)	0.7426 (2)	0.48880 (14)	0.0300 (4)
H9AA	0.3616	0.8224	0.4976	0.036*	0.894 (5)
H9AB	0.4544	0.6638	0.5481	0.036*	0.894 (5)
H9BC	0.3988	0.7381	0.5557	0.036*	0.106 (5)
H9BD	0.4864	0.6409	0.4755	0.036*	0.106 (5)
C10A	0.4096 (3)	0.6805 (2)	0.39756 (15)	0.0268 (6)	0.894 (5)
H10A	0.2851	0.6223	0.4155	0.032*	0.894 (5)
H10B	0.5265	0.6131	0.3803	0.032*	0.894 (5)
C10B	0.325 (2)	0.8331 (16)	0.4112 (4)	0.039 (6)	0.106 (5)
H10C	0.3444	0.9386	0.4096	0.047*	0.106 (5)
H10D	0.1779	0.8152	0.4327	0.047*	0.106 (5)
C11	0.3613 (3)	0.8007 (2)	0.30379 (14)	0.0307 (4)
H11A	0.2770	0.7575	0.2587	0.037*	0.894 (5)
H11B	0.2731	0.8816	0.3259	0.037*	0.894 (5)
H11C	0.2338	0.8364	0.2659	0.037*	0.106 (5)
H11D	0.3768	0.6927	0.3082	0.037*	0.106 (5)
C12	0.5528 (3)	0.8683 (2)	0.24229 (14)	0.0300 (4)
H12A	0.5795	0.8182	0.1842	0.036*
H12B	0.5143	0.9730	0.2158	0.036*
C13	0.7605 (3)	0.8598 (2)	0.29827 (13)	0.0246 (4)
H13A	0.8624	0.9194	0.2545	0.030*
H13B	0.8186	0.7566	0.3102	0.031 (5)*
C14	0.7391 (3)	0.9139 (2)	0.39992 (14)	0.0282 (4)
H14A	0.632 (3)	0.995 (2)	0.3970 (15)	0.031 (5)*
H14B	0.875 (3)	0.951 (2)	0.4164 (15)	0.034 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0280 (2)	0.0189 (2)	0.0207 (2)	−0.00046 (17)	−0.00564 (17)	−0.00375 (17)
O1	0.0437 (8)	0.0216 (7)	0.0251 (7)	0.0051 (6)	−0.0074 (6)	−0.0087 (5)
O2	0.0284 (7)	0.0263 (7)	0.0323 (7)	−0.0062 (5)	−0.0059 (5)	−0.0008 (6)
O3	0.0279 (6)	0.0215 (7)	0.0221 (6)	0.0039 (5)	−0.0015 (5)	−0.0031 (5)
N1	0.0301 (8)	0.0202 (8)	0.0200 (8)	0.0063 (7)	−0.0062 (6)	−0.0033 (6)
N2	0.0344 (9)	0.0225 (8)	0.0216 (8)	0.0070 (7)	−0.0045 (6)	−0.0079 (7)
N3	0.0280 (8)	0.0221 (8)	0.0224 (8)	0.0044 (6)	−0.0069 (6)	−0.0030 (6)
C1	0.0284 (9)	0.0247 (9)	0.0166 (8)	−0.0040 (7)	−0.0030 (7)	−0.0057 (7)
C2	0.0206 (9)	0.0322 (11)	0.0290 (10)	−0.0041 (7)	0.0017 (7)	−0.0056 (8)
C3	0.0229 (9)	0.0249 (10)	0.0299 (10)	0.0058 (7)	−0.0027 (7)	−0.0048 (8)
C4	0.0248 (9)	0.0194 (9)	0.0162 (8)	0.0000 (7)	−0.0032 (7)	−0.0044 (7)
C5	0.0209 (9)	0.0266 (10)	0.0275 (10)	0.0006 (7)	−0.0011 (7)	−0.0002 (8)
C6	0.0258 (9)	0.0239 (10)	0.0275 (10)	0.0057 (7)	−0.0030 (7)	0.0005 (8)
C7	0.0376 (11)	0.0294 (11)	0.0289 (10)	−0.0088 (8)	−0.0034 (8)	−0.0006 (8)
C8	0.0236 (8)	0.0177 (9)	0.0182 (8)	−0.0026 (7)	0.0026 (7)	−0.0014 (7)
C9	0.0313 (10)	0.0312 (10)	0.0260 (10)	−0.0001 (8)	−0.0007 (8)	−0.0021 (8)
C10A	0.0238 (11)	0.0254 (12)	0.0321 (12)	−0.0049 (8)	0.0025 (8)	−0.0071 (9)
C10B	0.018 (9)	0.063 (15)	0.030 (11)	−0.007 (9)	0.002 (7)	0.011 (9)
C11	0.0245 (9)	0.0407 (12)	0.0283 (10)	−0.0002 (8)	−0.0051 (8)	−0.0092 (9)
C12	0.0296 (10)	0.0375 (11)	0.0214 (9)	0.0031 (8)	−0.0022 (7)	−0.0027 (8)
C13	0.0242 (9)	0.0234 (10)	0.0238 (9)	−0.0031 (7)	−0.0002 (7)	0.0026 (7)
C14	0.0350 (11)	0.0206 (10)	0.0294 (10)	−0.0032 (8)	−0.0090 (8)	−0.0025 (8)

Geometric parameters (Å, º)

S1—O1	1.4288 (13)	C9—H9AA	0.9700
S1—O2	1.4222 (13)	C9—H9AB	0.9700
S1—N1	1.6456 (15)	C9—H9BC	0.9700
S1—C4	1.7537 (17)	C9—H9BD	0.9700
O3—C8	1.226 (2)	C9—C10A	1.501 (3)
N1—H1	0.76 (2)	C9—C10B	1.490 (6)
N1—C8	1.383 (2)	C10A—H10A	0.9700
N2—H2	0.83 (2)	C10A—H10B	0.9700
N2—N3	1.412 (2)	C10A—C11	1.529 (3)
N2—C8	1.340 (2)	C10B—H10C	0.9700
N3—C9	1.475 (2)	C10B—H10D	0.9700
N3—C14	1.477 (2)	C10B—C11	1.519 (6)
C1—C2	1.383 (3)	C11—H11A	0.9700
C1—C6	1.388 (2)	C11—H11B	0.9700
C1—C7	1.501 (2)	C11—H11C	0.9700
C2—H2A	0.9300	C11—H11D	0.9700
C2—C3	1.381 (3)	C11—C12	1.524 (2)
C3—H3	0.9300	C12—H12A	0.9700
C3—C4	1.383 (2)	C12—H12B	0.9700
C4—C5	1.380 (2)	C12—C13	1.521 (2)
C5—H5	0.9300	C13—H13A	0.9700
C5—C6	1.384 (2)	C13—H13B	0.9700
C6—H6	0.9300	C13—C14	1.522 (3)
C7—H7A	0.9600	C14—H14A	0.96 (2)
C7—H7B	0.9600	C14—H14B	0.99 (2)
C7—H7C	0.9600
O1—S1—N1	103.50 (8)	H9AA—C9—H9AB	107.0
O1—S1—C4	109.38 (8)	H9BC—C9—H9BD	107.7
O2—S1—O1	119.76 (8)	C10A—C9—H9AA	107.5
O2—S1—N1	108.99 (8)	C10A—C9—H9AB	107.5
O2—S1—C4	108.83 (8)	C10B—C9—H9BC	108.8
N1—S1—C4	105.39 (8)	C10B—C9—H9BD	108.8
S1—N1—H1	117.1 (16)	C9—C10A—H10A	108.8
C8—N1—S1	124.01 (13)	C9—C10A—H10B	108.8
C8—N1—H1	117.2 (16)	C9—C10A—C11	113.79 (16)
N3—N2—H2	121.1 (14)	H10A—C10A—H10B	107.7
C8—N2—H2	117.6 (14)	C11—C10A—H10A	108.8
C8—N2—N3	120.41 (14)	C11—C10A—H10B	108.8
N2—N3—C9	110.48 (14)	C9—C10B—H10C	108.5
N2—N3—C14	110.10 (14)	C9—C10B—H10D	108.5
C9—N3—C14	115.52 (14)	C9—C10B—C11	115.0 (4)
C2—C1—C6	118.08 (16)	H10C—C10B—H10D	107.5
C2—C1—C7	121.10 (16)	C11—C10B—H10C	108.5
C6—C1—C7	120.80 (16)	C11—C10B—H10D	108.5
C1—C2—H2A	119.0	C10A—C11—H11A	108.1
C3—C2—C1	122.00 (16)	C10A—C11—H11B	108.1
C3—C2—H2A	119.0	C10B—C11—H11C	108.0
C2—C3—H3	120.7	C10B—C11—H11D	108.0
C2—C3—C4	118.57 (16)	C10B—C11—C12	117.0 (7)
C4—C3—H3	120.7	H11A—C11—H11B	107.3
C3—C4—S1	119.45 (13)	H11C—C11—H11D	107.3
C5—C4—S1	119.57 (12)	C12—C11—C10A	116.78 (16)
C5—C4—C3	120.94 (16)	C12—C11—H11A	108.1
C4—C5—H5	120.3	C12—C11—H11B	108.1
C4—C5—C6	119.32 (15)	C12—C11—H11C	108.0
C6—C5—H5	120.3	C12—C11—H11D	108.0
C1—C6—H6	119.5	C11—C12—H12A	108.1
C5—C6—C1	121.08 (16)	C11—C12—H12B	108.1
C5—C6—H6	119.5	H12A—C12—H12B	107.3
C1—C7—H7A	109.5	C13—C12—C11	116.71 (15)
C1—C7—H7B	109.5	C13—C12—H12A	108.1
C1—C7—H7C	109.5	C13—C12—H12B	108.1
H7A—C7—H7B	109.5	C12—C13—H13A	108.6
H7A—C7—H7C	109.5	C12—C13—H13B	108.6
H7B—C7—H7C	109.5	C12—C13—C14	114.74 (15)
O3—C8—N1	122.01 (15)	H13A—C13—H13B	107.6
O3—C8—N2	123.68 (15)	C14—C13—H13A	108.6
N2—C8—N1	114.31 (15)	C14—C13—H13B	108.6
N3—C9—H9AA	107.5	N3—C14—C13	116.65 (15)
N3—C9—H9AB	107.5	N3—C14—H14A	105.8 (12)
N3—C9—H9BC	108.8	N3—C14—H14B	105.3 (12)
N3—C9—H9BD	108.8	C13—C14—H14A	110.4 (12)
N3—C9—C10A	119.13 (15)	C13—C14—H14B	110.6 (11)
N3—C9—C10B	113.9 (7)	H14A—C14—H14B	107.6 (16)
S1—N1—C8—O3	−3.3 (2)	C2—C3—C4—S1	−177.89 (13)
S1—N1—C8—N2	177.23 (12)	C2—C3—C4—C5	0.2 (3)
S1—C4—C5—C6	177.05 (13)	C3—C4—C5—C6	−1.0 (3)
O1—S1—N1—C8	−172.43 (14)	C4—S1—N1—C8	−57.59 (16)
O1—S1—C4—C3	38.55 (16)	C4—C5—C6—C1	1.2 (3)
O1—S1—C4—C5	−139.55 (14)	C6—C1—C2—C3	−0.3 (3)
O2—S1—N1—C8	59.07 (16)	C7—C1—C2—C3	−178.55 (16)
O2—S1—C4—C3	171.07 (13)	C7—C1—C6—C5	177.68 (16)
O2—S1—C4—C5	−7.03 (16)	C8—N2—N3—C9	−109.99 (17)
N1—S1—C4—C3	−72.15 (15)	C8—N2—N3—C14	121.22 (16)
N1—S1—C4—C5	109.74 (15)	C9—N3—C14—C13	−63.6 (2)
N2—N3—C9—C10A	−74.0 (2)	C9—C10A—C11—C12	78.6 (2)
N2—N3—C9—C10B	−141.4 (3)	C9—C10B—C11—C12	−77.7 (12)
N2—N3—C14—C13	62.4 (2)	C10A—C11—C12—C13	−23.5 (2)
N3—N2—C8—O3	175.57 (15)	C10B—C11—C12—C13	42.9 (4)
N3—N2—C8—N1	−5.0 (2)	C11—C12—C13—C14	−49.7 (2)
N3—C9—C10A—C11	−73.9 (2)	C12—C13—C14—N3	86.5 (2)
N3—C9—C10B—C11	82.2 (12)	C14—N3—C9—C10A	51.7 (2)
C1—C2—C3—C4	0.5 (3)	C14—N3—C9—C10B	−15.6 (4)
C2—C1—C6—C5	−0.6 (3)

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_125)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.394 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.2586 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0748 (4) Å	Cell parameters from 5366 reflections
c = 13.3249 (5) Å	θ = 2.3–28.8°
α = 79.432 (3)°	µ = 0.23 mm^−1
β = 87.442 (3)°	T = 125 K
γ = 85.975 (3)°	Block, colourless
V = 741.73 (5) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3037 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2585 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.894, Tmax = 1.000	l = −16→16
11961 measured reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0337P)^2 + 0.3459P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3037 reflections	Δρmax = 0.40 e Å^−3
213 parameters	Δρmin = −0.38 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	Occ. (<1)
S1	0.01918 (6)	0.26706 (4)	0.22345 (3)	0.01862 (12)
O1	0.14089 (19)	0.15310 (13)	0.18063 (9)	0.0250 (3)
O2	−0.20835 (18)	0.26633 (13)	0.23096 (9)	0.0246 (3)
O3	−0.07315 (17)	0.45398 (12)	0.38331 (8)	0.0202 (3)
N1	0.1130 (2)	0.24858 (16)	0.33886 (11)	0.0201 (3)
H1	0.211 (3)	0.191 (2)	0.3536 (15)	0.028 (6)*
N2	0.1595 (2)	0.31515 (16)	0.49372 (11)	0.0217 (3)
H2	0.142 (3)	0.379 (2)	0.5331 (15)	0.029 (5)*
N3	0.3205 (2)	0.19704 (15)	0.50985 (10)	0.0204 (3)
C1	0.2010 (3)	0.72212 (19)	0.05164 (12)	0.0195 (3)
C2	0.3549 (3)	0.6050 (2)	0.07675 (13)	0.0225 (4)
H2A	0.4972	0.6205	0.0571	0.027*
C3	0.3030 (3)	0.46608 (19)	0.13018 (13)	0.0219 (4)
H3	0.4083	0.3888	0.1461	0.026*
C4	0.0908 (2)	0.44445 (18)	0.15951 (12)	0.0170 (3)
C5	−0.0663 (3)	0.55888 (19)	0.13637 (13)	0.0215 (4)
H5	−0.2081	0.5436	0.1572	0.026*
C6	−0.0105 (3)	0.69659 (19)	0.08185 (13)	0.0226 (4)
H6	−0.1165	0.7733	0.0652	0.027*
C7	0.2622 (3)	0.8732 (2)	−0.00399 (13)	0.0265 (4)
H7A	0.4033	0.8640	−0.0344	0.040*
H7B	0.2607	0.9415	0.0432	0.040*
H7C	0.1616	0.9108	−0.0564	0.040*
C8	0.0581 (2)	0.34786 (18)	0.40502 (12)	0.0179 (3)
C9	0.5333 (3)	0.2569 (2)	0.51079 (13)	0.0243 (4)
H9AA	0.5465	0.3355	0.4512	0.029*	0.927 (5)
H9AB	0.6401	0.1770	0.5023	0.029*	0.927 (5)
H9BC	0.5146	0.3585	0.5243	0.029*	0.073 (5)
H9BD	0.6016	0.2617	0.4436	0.029*	0.073 (5)
C10A	0.5911 (3)	0.3199 (2)	0.60256 (14)	0.0222 (5)	0.927 (5)
H10A	0.4728	0.3864	0.6202	0.027*	0.927 (5)
H10B	0.7147	0.3793	0.5846	0.027*	0.927 (5)
C10B	0.679 (3)	0.165 (2)	0.5886 (6)	0.034 (8)*	0.073 (5)
H10C	0.8264	0.1836	0.5669	0.040*	0.073 (5)
H10D	0.6599	0.0598	0.5906	0.040*	0.073 (5)
C11	0.6418 (3)	0.1993 (2)	0.69612 (13)	0.0255 (4)
H11A	0.7286	0.1180	0.6735	0.031*	0.927 (5)
H11B	0.7281	0.2422	0.7408	0.031*	0.927 (5)
H11C	0.6263	0.3075	0.6909	0.031*	0.073 (5)
H11D	0.7696	0.1641	0.7342	0.031*	0.073 (5)
C12	0.4494 (3)	0.1327 (2)	0.75867 (13)	0.0250 (4)
H12A	0.4882	0.0282	0.7864	0.030*
H12B	0.4225	0.1845	0.8160	0.030*
C13	0.2412 (3)	0.13973 (19)	0.70238 (12)	0.0207 (4)
H13A	0.1398	0.0795	0.7462	0.025*
H13B	0.1815	0.2428	0.6904	0.024 (5)*
C14	0.2636 (3)	0.0855 (2)	0.60060 (13)	0.0233 (4)
H14A	0.371 (3)	0.004 (2)	0.6037 (13)	0.022 (5)*
H14B	0.129 (3)	0.047 (2)	0.5862 (14)	0.025 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0234 (2)	0.0156 (2)	0.0170 (2)	−0.00040 (16)	−0.00456 (16)	−0.00297 (16)
O1	0.0360 (7)	0.0189 (6)	0.0213 (6)	0.0036 (5)	−0.0061 (5)	−0.0074 (5)
O2	0.0242 (6)	0.0219 (6)	0.0273 (7)	−0.0048 (5)	−0.0049 (5)	−0.0012 (5)
O3	0.0228 (6)	0.0182 (6)	0.0189 (6)	0.0034 (5)	−0.0020 (5)	−0.0027 (5)
N1	0.0253 (8)	0.0169 (7)	0.0173 (7)	0.0046 (6)	−0.0058 (6)	−0.0025 (6)
N2	0.0286 (8)	0.0187 (8)	0.0180 (7)	0.0062 (6)	−0.0041 (6)	−0.0064 (6)
N3	0.0234 (7)	0.0185 (7)	0.0188 (7)	0.0037 (6)	−0.0051 (6)	−0.0030 (6)
C1	0.0243 (8)	0.0214 (9)	0.0137 (8)	−0.0030 (7)	−0.0029 (6)	−0.0047 (7)
C2	0.0170 (8)	0.0271 (10)	0.0239 (9)	−0.0032 (7)	0.0018 (7)	−0.0059 (7)
C3	0.0192 (8)	0.0224 (9)	0.0239 (9)	0.0044 (7)	−0.0030 (7)	−0.0047 (7)
C4	0.0213 (8)	0.0169 (8)	0.0128 (8)	0.0002 (6)	−0.0033 (6)	−0.0029 (6)
C5	0.0170 (8)	0.0238 (9)	0.0224 (9)	0.0002 (7)	−0.0011 (7)	−0.0012 (7)
C6	0.0217 (8)	0.0207 (9)	0.0233 (9)	0.0042 (7)	−0.0025 (7)	−0.0005 (7)
C7	0.0291 (9)	0.0247 (10)	0.0250 (9)	−0.0058 (8)	−0.0025 (7)	−0.0005 (7)
C8	0.0202 (8)	0.0158 (8)	0.0168 (8)	−0.0032 (7)	0.0020 (6)	−0.0004 (6)
C9	0.0254 (9)	0.0251 (9)	0.0211 (9)	−0.0006 (7)	0.0002 (7)	−0.0012 (7)
C10A	0.0191 (9)	0.0216 (10)	0.0264 (11)	−0.0035 (7)	0.0013 (7)	−0.0054 (8)
C11	0.0197 (8)	0.0339 (10)	0.0237 (9)	0.0004 (7)	−0.0050 (7)	−0.0071 (8)
C12	0.0250 (9)	0.0303 (10)	0.0184 (9)	0.0030 (7)	−0.0022 (7)	−0.0027 (7)
C13	0.0205 (8)	0.0192 (9)	0.0206 (9)	−0.0015 (7)	−0.0001 (7)	0.0012 (7)
C14	0.0282 (9)	0.0167 (9)	0.0253 (9)	−0.0034 (8)	−0.0060 (7)	−0.0029 (7)

Geometric parameters (Å, º)

S1—O1	1.4291 (12)	C9—H9AA	0.9700
S1—O2	1.4235 (12)	C9—H9AB	0.9700
S1—N1	1.6461 (14)	C9—H9BC	0.9700
S1—C4	1.7556 (16)	C9—H9BD	0.9700
O3—C8	1.2222 (19)	C9—C10A	1.509 (2)
N1—H1	0.79 (2)	C9—C10B	1.503 (6)
N1—C8	1.388 (2)	C10A—H10A	0.9700
N2—H2	0.85 (2)	C10A—H10B	0.9700
N2—N3	1.4121 (19)	C10A—C11	1.529 (3)
N2—C8	1.341 (2)	C10B—H10C	0.9700
N3—C9	1.474 (2)	C10B—H10D	0.9700
N3—C14	1.476 (2)	C10B—C11	1.523 (6)
C1—C2	1.387 (2)	C11—H11A	0.9700
C1—C6	1.389 (2)	C11—H11B	0.9700
C1—C7	1.501 (2)	C11—H11C	0.9700
C2—H2A	0.9300	C11—H11D	0.9700
C2—C3	1.382 (2)	C11—C12	1.529 (2)
C3—H3	0.9300	C12—H12A	0.9700
C3—C4	1.384 (2)	C12—H12B	0.9700
C4—C5	1.381 (2)	C12—C13	1.524 (2)
C5—H5	0.9300	C13—H13A	0.9700
C5—C6	1.384 (2)	C13—H13B	0.9700
C6—H6	0.9300	C13—C14	1.523 (2)
C7—H7A	0.9600	C14—H14A	0.958 (19)
C7—H7B	0.9600	C14—H14B	0.976 (18)
C7—H7C	0.9600
O1—S1—N1	103.40 (7)	H9AA—C9—H9AB	107.1
O1—S1—C4	109.34 (7)	H9BC—C9—H9BD	107.7
O2—S1—O1	119.79 (7)	C10A—C9—H9AA	107.6
O2—S1—N1	109.04 (7)	C10A—C9—H9AB	107.6
O2—S1—C4	108.88 (7)	C10B—C9—H9BC	108.8
N1—S1—C4	105.40 (7)	C10B—C9—H9BD	108.8
S1—N1—H1	118.3 (15)	C9—C10A—H10A	108.9
C8—N1—S1	123.78 (12)	C9—C10A—H10B	108.9
C8—N1—H1	116.7 (15)	C9—C10A—C11	113.52 (15)
N3—N2—H2	121.7 (14)	H10A—C10A—H10B	107.7
C8—N2—H2	116.7 (14)	C11—C10A—H10A	108.9
C8—N2—N3	120.38 (14)	C11—C10A—H10B	108.9
N2—N3—C9	110.62 (13)	C9—C10B—H10C	108.7
N2—N3—C14	110.04 (13)	C9—C10B—H10D	108.7
C9—N3—C14	115.25 (13)	C9—C10B—C11	114.2 (4)
C2—C1—C6	118.07 (15)	H10C—C10B—H10D	107.6
C2—C1—C7	120.93 (15)	C11—C10B—H10C	108.7
C6—C1—C7	120.98 (15)	C11—C10B—H10D	108.7
C1—C2—H2A	119.0	C10A—C11—H11A	108.2
C3—C2—C1	121.91 (15)	C10A—C11—H11B	108.2
C3—C2—H2A	119.0	C10B—C11—H11C	107.9
C2—C3—H3	120.7	C10B—C11—H11D	107.9
C2—C3—C4	118.59 (16)	C10B—C11—C12	117.5 (10)
C4—C3—H3	120.7	H11A—C11—H11B	107.4
C3—C4—S1	119.48 (13)	H11C—C11—H11D	107.2
C5—C4—S1	119.48 (12)	C12—C11—C10A	116.33 (14)
C5—C4—C3	121.00 (15)	C12—C11—H11A	108.2
C4—C5—H5	120.3	C12—C11—H11B	108.2
C4—C5—C6	119.32 (15)	C12—C11—H11C	107.9
C6—C5—H5	120.3	C12—C11—H11D	107.9
C1—C6—H6	119.5	C11—C12—H12A	108.2
C5—C6—C1	121.09 (16)	C11—C12—H12B	108.2
C5—C6—H6	119.5	H12A—C12—H12B	107.3
C1—C7—H7A	109.5	C13—C12—C11	116.50 (14)
C1—C7—H7B	109.5	C13—C12—H12A	108.2
C1—C7—H7C	109.5	C13—C12—H12B	108.2
H7A—C7—H7B	109.5	C12—C13—H13A	108.6
H7A—C7—H7C	109.5	C12—C13—H13B	108.6
H7B—C7—H7C	109.5	H13A—C13—H13B	107.5
O3—C8—N1	122.01 (15)	C14—C13—C12	114.83 (14)
O3—C8—N2	123.97 (15)	C14—C13—H13A	108.6
N2—C8—N1	114.02 (15)	C14—C13—H13B	108.6
N3—C9—H9AA	107.6	N3—C14—C13	116.91 (14)
N3—C9—H9AB	107.6	N3—C14—H14A	106.2 (11)
N3—C9—H9BC	108.8	N3—C14—H14B	106.5 (11)
N3—C9—H9BD	108.8	C13—C14—H14A	110.4 (11)
N3—C9—C10A	118.75 (14)	C13—C14—H14B	109.5 (11)
N3—C9—C10B	113.9 (10)	H14A—C14—H14B	106.8 (15)
S1—N1—C8—O3	3.3 (2)	C2—C3—C4—S1	177.74 (12)
S1—N1—C8—N2	−177.45 (11)	C2—C3—C4—C5	−0.2 (2)
S1—C4—C5—C6	−177.06 (12)	C3—C4—C5—C6	0.8 (2)
O1—S1—N1—C8	172.42 (13)	C4—S1—N1—C8	57.66 (15)
O1—S1—C4—C3	−38.35 (15)	C4—C5—C6—C1	−1.1 (2)
O1—S1—C4—C5	139.59 (13)	C6—C1—C2—C3	0.0 (2)
O2—S1—N1—C8	−59.09 (15)	C7—C1—C2—C3	178.37 (15)
O2—S1—C4—C3	−170.91 (12)	C7—C1—C6—C5	−177.67 (15)
O2—S1—C4—C5	7.03 (15)	C8—N2—N3—C9	109.40 (16)
N1—S1—C4—C3	72.23 (14)	C8—N2—N3—C14	−122.11 (15)
N1—S1—C4—C5	−109.83 (14)	C9—N3—C14—C13	64.2 (2)
N2—N3—C9—C10A	73.62 (19)	C9—C10A—C11—C12	−79.85 (19)
N2—N3—C9—C10B	141.4 (3)	C9—C10B—C11—C12	77.6 (17)
N2—N3—C14—C13	−61.73 (19)	C10A—C11—C12—C13	24.9 (2)
N3—N2—C8—O3	−175.31 (14)	C10B—C11—C12—C13	−42.5 (4)
N3—N2—C8—N1	5.5 (2)	C11—C12—C13—C14	48.7 (2)
N3—C9—C10A—C11	74.5 (2)	C12—C13—C14—N3	−86.64 (19)
N3—C9—C10B—C11	−82.3 (16)	C14—N3—C9—C10A	−52.0 (2)
C1—C2—C3—C4	−0.3 (2)	C14—N3—C9—C10B	15.8 (4)
C2—C1—C6—C5	0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.85 (2)	2.05 (2)	2.8961 (18)	173.4 (19)

Symmetry code: (i) −x, −y+1, −z+1.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_100)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.400 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.2433 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0724 (4) Å	Cell parameters from 5559 reflections
c = 13.3119 (5) Å	θ = 2.3–29.0°
α = 79.359 (4)°	µ = 0.23 mm^−1
β = 87.461 (3)°	T = 100 K
γ = 85.933 (3)°	Block, colourless
V = 738.80 (5) Å^3	0.4 × 0.1 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3021 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2604 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.934, Tmax = 1.000	l = −16→16
11890 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 0.3817P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3021 reflections	Δρmax = 0.44 e Å^−3
208 parameters	Δρmin = −0.40 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
S1	0.01861 (6)	0.26687 (4)	0.22346 (3)	0.01516 (12)
O1	0.14105 (19)	0.15283 (13)	0.18048 (9)	0.0204 (3)
O2	−0.20987 (18)	0.26621 (13)	0.23085 (9)	0.0200 (3)
O3	−0.07370 (17)	0.45367 (12)	0.38361 (8)	0.0167 (3)
N1	0.1127 (2)	0.24786 (16)	0.33920 (10)	0.0162 (3)
H1	0.213 (3)	0.193 (2)	0.3511 (14)	0.019 (5)*
N2	0.1591 (2)	0.31406 (16)	0.49428 (11)	0.0173 (3)
H2	0.143 (3)	0.376 (2)	0.5328 (15)	0.020 (5)*
N3	0.3212 (2)	0.19597 (15)	0.51034 (10)	0.0163 (3)
C1	0.2002 (3)	0.72260 (18)	0.05139 (12)	0.0164 (3)
C2	0.3551 (3)	0.60528 (19)	0.07648 (12)	0.0182 (4)
H2A	0.4978	0.6208	0.0568	0.022*
C3	0.3031 (3)	0.46589 (19)	0.12991 (12)	0.0183 (4)
H3	0.4086	0.3883	0.1456	0.022*
C4	0.0901 (2)	0.44457 (18)	0.15961 (11)	0.0140 (3)
C5	−0.0676 (3)	0.55928 (19)	0.13686 (12)	0.0177 (4)
H5	−0.2096	0.5441	0.1581	0.021*
C6	−0.0119 (3)	0.69707 (19)	0.08208 (12)	0.0184 (4)
H6	−0.1182	0.7739	0.0655	0.022*
C7	0.2614 (3)	0.87395 (19)	−0.00417 (13)	0.0216 (4)
H7A	0.4033	0.8650	−0.0342	0.032*
H7B	0.2588	0.9422	0.0431	0.032*
H7C	0.1612	0.9114	−0.0570	0.032*
C8	0.0576 (2)	0.34693 (18)	0.40537 (12)	0.0145 (3)
C9	0.5343 (3)	0.25590 (19)	0.51034 (13)	0.0192 (4)
H9A	0.5472	0.3340	0.4503	0.023*
H9B	0.6415	0.1758	0.5023	0.023*
C10	0.5917 (3)	0.32049 (19)	0.60253 (13)	0.0209 (4)
H10A	0.4722	0.3862	0.6202	0.025*
H10B	0.7147	0.3807	0.5843	0.025*
C11	0.6442 (3)	0.1997 (2)	0.69586 (13)	0.0202 (4)
H11A	0.7323	0.2422	0.7401	0.024*
H11B	0.7299	0.1181	0.6729	0.024*
C12	0.4515 (3)	0.1338 (2)	0.75942 (12)	0.0199 (4)
H12A	0.4907	0.0297	0.7883	0.024*
H12B	0.4243	0.1871	0.8160	0.024*
C13	0.2424 (3)	0.13928 (19)	0.70317 (12)	0.0169 (3)
H13A	0.1415	0.0787	0.7473	0.020*
H13B	0.1814	0.2421	0.6907	0.022 (5)*
C14	0.2657 (3)	0.08411 (19)	0.60146 (13)	0.0184 (4)
H14A	0.374 (3)	0.002 (2)	0.6061 (14)	0.020 (5)*
H14B	0.131 (3)	0.0457 (19)	0.5867 (13)	0.015 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0187 (2)	0.0129 (2)	0.0140 (2)	−0.00021 (15)	−0.00386 (15)	−0.00245 (15)
O1	0.0284 (6)	0.0163 (6)	0.0177 (6)	0.0021 (5)	−0.0038 (5)	−0.0066 (5)
O2	0.0189 (6)	0.0183 (6)	0.0226 (6)	−0.0039 (5)	−0.0036 (5)	−0.0013 (5)
O3	0.0179 (6)	0.0156 (6)	0.0159 (6)	0.0024 (5)	−0.0008 (4)	−0.0024 (5)
N1	0.0187 (7)	0.0148 (7)	0.0145 (7)	0.0041 (6)	−0.0045 (6)	−0.0024 (6)
N2	0.0224 (7)	0.0149 (7)	0.0153 (7)	0.0049 (6)	−0.0032 (6)	−0.0062 (6)
N3	0.0177 (7)	0.0150 (7)	0.0157 (7)	0.0032 (5)	−0.0037 (5)	−0.0026 (6)
C1	0.0205 (8)	0.0181 (8)	0.0115 (8)	−0.0033 (7)	−0.0025 (6)	−0.0041 (6)
C2	0.0147 (8)	0.0217 (9)	0.0185 (9)	−0.0024 (7)	0.0007 (6)	−0.0045 (7)
C3	0.0158 (8)	0.0197 (9)	0.0190 (9)	0.0042 (7)	−0.0027 (6)	−0.0044 (7)
C4	0.0184 (8)	0.0140 (8)	0.0101 (7)	−0.0003 (6)	−0.0020 (6)	−0.0029 (6)
C5	0.0142 (8)	0.0200 (9)	0.0180 (8)	0.0003 (7)	−0.0003 (6)	−0.0014 (7)
C6	0.0173 (8)	0.0167 (9)	0.0195 (9)	0.0046 (7)	−0.0023 (7)	−0.0007 (7)
C7	0.0247 (9)	0.0193 (9)	0.0202 (9)	−0.0049 (7)	−0.0023 (7)	−0.0005 (7)
C8	0.0152 (8)	0.0138 (8)	0.0140 (8)	−0.0037 (6)	0.0025 (6)	−0.0010 (6)
C9	0.0194 (8)	0.0193 (9)	0.0178 (8)	−0.0002 (7)	0.0009 (7)	−0.0013 (7)
C10	0.0181 (8)	0.0210 (9)	0.0243 (9)	−0.0029 (7)	0.0017 (7)	−0.0060 (7)
C11	0.0154 (8)	0.0271 (10)	0.0190 (9)	0.0003 (7)	−0.0037 (7)	−0.0065 (7)
C12	0.0201 (8)	0.0240 (9)	0.0147 (8)	0.0024 (7)	−0.0014 (7)	−0.0023 (7)
C13	0.0161 (8)	0.0156 (8)	0.0173 (8)	−0.0010 (6)	0.0013 (6)	0.0008 (7)
C14	0.0211 (9)	0.0143 (8)	0.0197 (9)	−0.0019 (7)	−0.0049 (7)	−0.0013 (7)

Geometric parameters (Å, º)

S1—O1	1.4317 (12)	C6—H6	0.9300
S1—O2	1.4258 (12)	C7—H7A	0.9600
S1—N1	1.6481 (14)	C7—H7B	0.9600
S1—C4	1.7557 (16)	C7—H7C	0.9600
O3—C8	1.2242 (19)	C9—H9A	0.9700
N1—H1	0.78 (2)	C9—H9B	0.9700
N1—C8	1.387 (2)	C9—C10	1.521 (2)
N2—H2	0.83 (2)	C10—H10A	0.9700
N2—N3	1.4139 (19)	C10—H10B	0.9700
N2—C8	1.342 (2)	C10—C11	1.528 (2)
N3—C9	1.472 (2)	C11—H11A	0.9700
N3—C14	1.476 (2)	C11—H11B	0.9700
C1—C2	1.390 (2)	C11—C12	1.532 (2)
C1—C6	1.391 (2)	C12—H12A	0.9700
C1—C7	1.501 (2)	C12—H12B	0.9700
C2—H2A	0.9300	C12—C13	1.526 (2)
C2—C3	1.384 (2)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C3—C4	1.387 (2)	C13—C14	1.526 (2)
C4—C5	1.382 (2)	C14—H14A	0.96 (2)
C5—H5	0.9300	C14—H14B	0.976 (17)
C5—C6	1.385 (2)
O1—S1—N1	103.36 (7)	O3—C8—N1	122.14 (15)
O1—S1—C4	109.38 (7)	O3—C8—N2	123.79 (15)
O2—S1—O1	119.81 (7)	N2—C8—N1	114.06 (14)
O2—S1—N1	109.07 (7)	N3—C9—H9A	107.7
O2—S1—C4	108.81 (7)	N3—C9—H9B	107.7
N1—S1—C4	105.43 (7)	N3—C9—C10	118.26 (13)
S1—N1—H1	116.4 (14)	H9A—C9—H9B	107.1
C8—N1—S1	123.71 (12)	C10—C9—H9A	107.7
C8—N1—H1	118.0 (14)	C10—C9—H9B	107.7
N3—N2—H2	121.3 (13)	C9—C10—H10A	109.0
C8—N2—H2	117.0 (14)	C9—C10—H10B	109.0
C8—N2—N3	120.31 (14)	C9—C10—C11	113.05 (14)
N2—N3—C9	110.70 (12)	H10A—C10—H10B	107.8
N2—N3—C14	110.19 (12)	C11—C10—H10A	109.0
C9—N3—C14	115.29 (13)	C11—C10—H10B	109.0
C2—C1—C6	118.10 (15)	C10—C11—H11A	108.3
C2—C1—C7	120.87 (14)	C10—C11—H11B	108.3
C6—C1—C7	121.00 (15)	C10—C11—C12	116.08 (14)
C1—C2—H2A	119.1	H11A—C11—H11B	107.4
C3—C2—C1	121.85 (15)	C12—C11—H11A	108.3
C3—C2—H2A	119.1	C12—C11—H11B	108.3
C2—C3—H3	120.8	C11—C12—H12A	108.2
C2—C3—C4	118.50 (15)	C11—C12—H12B	108.2
C4—C3—H3	120.8	H12A—C12—H12B	107.3
C3—C4—S1	119.34 (13)	C13—C12—C11	116.41 (14)
C5—C4—S1	119.49 (12)	C13—C12—H12A	108.2
C5—C4—C3	121.14 (15)	C13—C12—H12B	108.2
C4—C5—H5	120.4	C12—C13—H13A	108.6
C4—C5—C6	119.26 (14)	C12—C13—H13B	108.6
C6—C5—H5	120.4	H13A—C13—H13B	107.5
C1—C6—H6	119.4	C14—C13—C12	114.79 (14)
C5—C6—C1	121.14 (15)	C14—C13—H13A	108.6
C5—C6—H6	119.4	C14—C13—H13B	108.6
C1—C7—H7A	109.5	N3—C14—C13	116.73 (13)
C1—C7—H7B	109.5	N3—C14—H14A	107.1 (11)
C1—C7—H7C	109.5	N3—C14—H14B	105.8 (10)
H7A—C7—H7B	109.5	C13—C14—H14A	109.6 (11)
H7A—C7—H7C	109.5	C13—C14—H14B	109.6 (10)
H7B—C7—H7C	109.5	H14A—C14—H14B	107.5 (14)
S1—N1—C8—O3	3.1 (2)	C2—C1—C6—C5	0.6 (2)
S1—N1—C8—N2	−177.43 (11)	C2—C3—C4—S1	177.75 (12)
S1—C4—C5—C6	−176.85 (12)	C2—C3—C4—C5	−0.1 (2)
O1—S1—N1—C8	172.36 (13)	C3—C4—C5—C6	1.0 (2)
O1—S1—C4—C3	−38.04 (15)	C4—S1—N1—C8	57.57 (14)
O1—S1—C4—C5	139.86 (13)	C4—C5—C6—C1	−1.2 (2)
O2—S1—N1—C8	−59.12 (14)	C6—C1—C2—C3	0.4 (2)
O2—S1—C4—C3	−170.60 (12)	C7—C1—C2—C3	178.37 (15)
O2—S1—C4—C5	7.29 (15)	C7—C1—C6—C5	−177.44 (15)
N1—S1—C4—C3	72.53 (14)	C8—N2—N3—C9	108.76 (16)
N1—S1—C4—C5	−109.58 (13)	C8—N2—N3—C14	−122.52 (15)
N2—N3—C9—C10	73.30 (18)	C9—N3—C14—C13	64.96 (19)
N2—N3—C14—C13	−61.22 (18)	C9—C10—C11—C12	−80.88 (18)
N3—N2—C8—O3	−174.91 (14)	C10—C11—C12—C13	26.0 (2)
N3—N2—C8—N1	5.7 (2)	C11—C12—C13—C14	48.0 (2)
N3—C9—C10—C11	75.08 (19)	C12—C13—C14—N3	−86.73 (18)
C1—C2—C3—C4	−0.6 (2)	C14—N3—C9—C10	−52.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.83 (2)	2.07 (2)	2.8975 (18)	172.9 (19)

Symmetry code: (i) −x, −y+1, −z+1.

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_II_295)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.325 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.4948 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0520 (4) Å	Cell parameters from 4126 reflections
c = 13.4605 (6) Å	θ = 3.8–25.7°
α = 82.467 (4)°	µ = 0.22 mm^−1
β = 85.251 (4)°	T = 295 K
γ = 85.836 (4)°	Plate, colourless
V = 780.31 (6) Å^3	0.45 × 0.3 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3189 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2335 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 3.4°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −11→11
Tmin = 0.949, Tmax = 1.000	l = −16→16
12592 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.1546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3189 reflections	Δρmax = 0.20 e Å^−3
218 parameters	Δρmin = −0.28 e Å^−3
3 restraints

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	Occ. (<1)
S1	0.25229 (8)	0.97193 (5)	0.39243 (4)	0.03985 (18)
O3	0.0634 (2)	0.67313 (16)	0.41245 (11)	0.0514 (4)
N1	0.2532 (3)	0.83253 (19)	0.48202 (13)	0.0397 (4)
N3	0.2865 (3)	0.64152 (19)	0.64517 (12)	0.0415 (4)
O1	0.3453 (2)	1.08737 (15)	0.43255 (11)	0.0498 (4)
O2	0.0517 (2)	1.00085 (17)	0.35695 (12)	0.0524 (4)
C8	0.1568 (3)	0.7003 (2)	0.48233 (15)	0.0390 (5)
C4	0.4216 (3)	0.9122 (2)	0.29466 (14)	0.0393 (5)
N2	0.1798 (3)	0.6048 (2)	0.56578 (14)	0.0538 (5)
C5	0.6253 (3)	0.8690 (2)	0.31221 (16)	0.0445 (5)
H5	0.6713	0.8667	0.3760	0.053*
C3	0.3526 (4)	0.9165 (3)	0.19988 (16)	0.0513 (6)
H3	0.2154	0.9455	0.1885	0.062*
C1	0.6949 (4)	0.8344 (3)	0.13806 (17)	0.0548 (6)
C6	0.7592 (4)	0.8295 (3)	0.23391 (17)	0.0525 (6)
H6	0.8958	0.7990	0.2457	0.063*
C2	0.4894 (4)	0.8774 (3)	0.12254 (16)	0.0591 (7)
H2A	0.4432	0.8798	0.0587	0.071*
C14	0.4723 (4)	0.5409 (3)	0.65574 (19)	0.0603 (6)
H14A	0.5743	0.5765	0.6030	0.072*	0.474 (7)
H14B	0.4367	0.4439	0.6416	0.072*	0.474 (7)
H14C	0.5478	0.5408	0.5905	0.072*	0.526 (7)
H14D	0.4307	0.4403	0.6776	0.072*	0.526 (7)
C9	0.1446 (4)	0.6451 (3)	0.73508 (17)	0.0577 (6)
H9A	0.1303	0.5438	0.7676	0.069*
H9B	0.0093	0.6849	0.7152	0.069*
C10	0.2141 (5)	0.7372 (3)	0.8090 (2)	0.0790 (9)
H10A	0.2599	0.8298	0.7721	0.095*
H10B	0.0946	0.7627	0.8531	0.095*
C7	0.8445 (5)	0.7908 (4)	0.0531 (2)	0.0848 (9)
H7A	0.7964	0.8367	−0.0099	0.127*
H7B	0.8533	0.6842	0.0546	0.127*
H7C	0.9788	0.8239	0.0608	0.127*
C11	0.3805 (6)	0.6716 (5)	0.8724 (2)	0.1079 (13)
H11C	0.3137	0.6308	0.9363	0.129*	0.526 (7)
H11D	0.4578	0.7537	0.8858	0.129*	0.526 (7)
H11A	0.3426	0.5754	0.9070	0.129*	0.474 (7)
H11B	0.3989	0.7362	0.9226	0.129*	0.474 (7)
C13A	0.5765 (13)	0.5165 (7)	0.7509 (5)	0.061 (2)	0.474 (7)
H13A	0.7176	0.4783	0.7362	0.073*	0.474 (7)
H13B	0.5075	0.4394	0.7956	0.073*	0.474 (7)
C12A	0.5835 (8)	0.6521 (7)	0.8073 (5)	0.0622 (19)	0.474 (7)
H12A	0.6026	0.7410	0.7596	0.075*	0.474 (7)
H12B	0.6993	0.6380	0.8494	0.075*	0.474 (7)
C13B	0.6125 (10)	0.5816 (9)	0.7281 (4)	0.073 (2)	0.526 (7)
H13C	0.6343	0.6872	0.7124	0.088*	0.526 (7)
H13D	0.7455	0.5277	0.7175	0.088*	0.526 (7)
C12B	0.5396 (11)	0.5508 (7)	0.8398 (4)	0.099 (3)	0.526 (7)
H12C	0.4787	0.4548	0.8524	0.119*	0.526 (7)
H12D	0.6581	0.5457	0.8798	0.119*	0.526 (7)
H1	0.315 (3)	0.836 (2)	0.5303 (17)	0.048 (7)*
H2	0.126 (4)	0.526 (3)	0.5721 (17)	0.054 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0459 (3)	0.0346 (3)	0.0401 (3)	−0.0066 (2)	−0.0070 (2)	−0.0037 (2)
O3	0.0651 (10)	0.0462 (9)	0.0468 (9)	−0.0152 (7)	−0.0187 (8)	−0.0051 (7)
N1	0.0475 (11)	0.0400 (10)	0.0334 (9)	−0.0123 (8)	−0.0079 (8)	−0.0033 (8)
N3	0.0452 (10)	0.0445 (10)	0.0364 (9)	−0.0100 (8)	−0.0082 (8)	−0.0034 (8)
O1	0.0656 (10)	0.0352 (8)	0.0511 (9)	−0.0123 (7)	−0.0077 (7)	−0.0079 (7)
O2	0.0481 (9)	0.0511 (9)	0.0585 (9)	0.0006 (7)	−0.0126 (7)	−0.0050 (7)
C8	0.0428 (12)	0.0376 (11)	0.0380 (11)	−0.0089 (9)	−0.0035 (9)	−0.0066 (9)
C4	0.0482 (12)	0.0348 (10)	0.0361 (11)	−0.0143 (9)	−0.0052 (9)	−0.0009 (8)
N2	0.0762 (14)	0.0423 (11)	0.0468 (11)	−0.0270 (10)	−0.0222 (10)	0.0039 (9)
C5	0.0476 (13)	0.0494 (12)	0.0386 (11)	−0.0118 (10)	−0.0056 (9)	−0.0063 (10)
C3	0.0544 (14)	0.0590 (14)	0.0413 (12)	−0.0121 (11)	−0.0106 (10)	−0.0005 (11)
C1	0.0640 (16)	0.0559 (14)	0.0453 (13)	−0.0211 (12)	0.0087 (11)	−0.0083 (11)
C6	0.0481 (14)	0.0561 (14)	0.0551 (14)	−0.0114 (11)	−0.0010 (11)	−0.0107 (11)
C2	0.0739 (18)	0.0721 (16)	0.0335 (12)	−0.0182 (14)	−0.0054 (11)	−0.0065 (11)
C14	0.0594 (15)	0.0566 (14)	0.0660 (16)	0.0037 (12)	−0.0081 (12)	−0.0145 (12)
C9	0.0477 (14)	0.0713 (16)	0.0505 (14)	−0.0030 (12)	−0.0005 (11)	0.0032 (12)
C10	0.101 (2)	0.0784 (19)	0.0587 (16)	0.0002 (17)	0.0091 (16)	−0.0268 (15)
C7	0.092 (2)	0.105 (2)	0.0595 (17)	−0.0225 (18)	0.0209 (16)	−0.0256 (16)
C11	0.117 (3)	0.150 (4)	0.068 (2)	−0.014 (3)	−0.024 (2)	−0.041 (2)
C13A	0.058 (4)	0.049 (4)	0.074 (5)	0.002 (3)	−0.018 (3)	−0.001 (3)
C12A	0.064 (4)	0.070 (4)	0.058 (4)	−0.012 (3)	−0.014 (3)	−0.017 (3)
C13B	0.053 (4)	0.061 (5)	0.107 (5)	−0.008 (3)	−0.031 (4)	0.005 (4)
C12B	0.150 (7)	0.072 (5)	0.079 (5)	−0.004 (5)	−0.060 (5)	0.005 (4)

Geometric parameters (Å, º)

S1—N1	1.6272 (18)	C14—C13A	1.481 (5)
S1—O1	1.4291 (14)	C14—C13B	1.484 (5)
S1—O2	1.4197 (15)	C9—H9A	0.9700
S1—C4	1.759 (2)	C9—H9B	0.9700
O3—C8	1.221 (2)	C9—C10	1.495 (4)
N1—C8	1.390 (2)	C10—H10A	0.9700
N1—H1	0.79 (2)	C10—H10B	0.9700
N3—N2	1.408 (2)	C10—C11	1.475 (5)
N3—C14	1.463 (3)	C7—H7A	0.9600
N3—C9	1.462 (3)	C7—H7B	0.9600
C8—N2	1.336 (3)	C7—H7C	0.9600
C4—C5	1.382 (3)	C11—H11C	0.9700
C4—C3	1.382 (3)	C11—H11D	0.9700
N2—H2	0.81 (2)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C5—C6	1.377 (3)	C11—C12A	1.535 (6)
C3—H3	0.9300	C11—C12B	1.531 (6)
C3—C2	1.377 (3)	C13A—H13A	0.9700
C1—C6	1.383 (3)	C13A—H13B	0.9700
C1—C2	1.388 (3)	C13A—C12A	1.531 (5)
C1—C7	1.512 (3)	C12A—H12A	0.9700
C6—H6	0.9300	C12A—H12B	0.9700
C2—H2A	0.9300	C13B—H13C	0.9700
C14—H14A	0.9700	C13B—H13D	0.9700
C14—H14B	0.9700	C13B—C12B	1.535 (6)
C14—H14C	0.9700	C12B—H12C	0.9700
C14—H14D	0.9700	C12B—H12D	0.9700
N1—S1—C4	105.36 (9)	H9A—C9—H9B	107.7
O1—S1—N1	104.51 (9)	C10—C9—H9A	108.9
O1—S1—C4	108.23 (9)	C10—C9—H9B	108.9
O2—S1—N1	110.37 (9)	C9—C10—H10A	107.9
O2—S1—O1	119.15 (9)	C9—C10—H10B	107.9
O2—S1—C4	108.37 (10)	H10A—C10—H10B	107.2
S1—N1—H1	120.1 (16)	C11—C10—C9	117.7 (3)
C8—N1—S1	125.60 (15)	C11—C10—H10A	107.9
C8—N1—H1	114.3 (16)	C11—C10—H10B	107.9
N2—N3—C14	108.75 (17)	C1—C7—H7A	109.5
N2—N3—C9	109.58 (16)	C1—C7—H7B	109.5
C9—N3—C14	116.07 (18)	C1—C7—H7C	109.5
O3—C8—N1	123.25 (19)	H7A—C7—H7B	109.5
O3—C8—N2	123.34 (18)	H7A—C7—H7C	109.5
N2—C8—N1	113.39 (18)	H7B—C7—H7C	109.5
C5—C4—S1	119.58 (15)	C10—C11—H11C	106.8
C3—C4—S1	119.63 (18)	C10—C11—H11D	106.8
C3—C4—C5	120.7 (2)	C10—C11—H11A	109.7
N3—N2—H2	119.1 (17)	C10—C11—H11B	109.7
C8—N2—N3	121.47 (17)	C10—C11—C12A	110.0 (3)
C8—N2—H2	119.3 (17)	C10—C11—C12B	122.3 (3)
C4—C5—H5	120.4	H11C—C11—H11D	106.6
C6—C5—C4	119.1 (2)	H11A—C11—H11B	108.2
C6—C5—H5	120.4	C12A—C11—H11A	109.7
C4—C3—H3	120.4	C12A—C11—H11B	109.7
C2—C3—C4	119.2 (2)	C12B—C11—H11C	106.8
C2—C3—H3	120.4	C12B—C11—H11D	106.8
C6—C1—C2	118.3 (2)	C14—C13A—H13A	108.1
C6—C1—C7	120.6 (2)	C14—C13A—H13B	108.1
C2—C1—C7	121.1 (2)	C14—C13A—C12A	116.8 (4)
C5—C6—C1	121.4 (2)	H13A—C13A—H13B	107.3
C5—C6—H6	119.3	C12A—C13A—H13A	108.1
C1—C6—H6	119.3	C12A—C13A—H13B	108.1
C3—C2—C1	121.2 (2)	C11—C12A—H12A	109.8
C3—C2—H2A	119.4	C11—C12A—H12B	109.8
C1—C2—H2A	119.4	C13A—C12A—C11	109.5 (5)
N3—C14—H14A	107.1	C13A—C12A—H12A	109.8
N3—C14—H14B	107.1	C13A—C12A—H12B	109.8
N3—C14—H14C	108.8	H12A—C12A—H12B	108.2
N3—C14—H14D	108.8	C14—C13B—H13C	108.2
N3—C14—C13A	120.9 (3)	C14—C13B—H13D	108.2
N3—C14—C13B	113.7 (4)	C14—C13B—C12B	116.3 (5)
H14A—C14—H14B	106.8	H13C—C13B—H13D	107.4
H14C—C14—H14D	107.7	C12B—C13B—H13C	108.2
C13A—C14—H14A	107.1	C12B—C13B—H13D	108.2
C13A—C14—H14B	107.1	C11—C12B—C13B	112.1 (5)
C13B—C14—H14C	108.8	C11—C12B—H12C	109.2
C13B—C14—H14D	108.8	C11—C12B—H12D	109.2
N3—C9—H9A	108.9	C13B—C12B—H12C	109.2
N3—C9—H9B	108.9	C13B—C12B—H12D	109.2
N3—C9—C10	113.3 (2)	H12C—C12B—H12D	107.9
S1—N1—C8—O3	1.9 (3)	N2—N3—C14—C13A	−159.2 (4)
S1—N1—C8—N2	−179.31 (16)	N2—N3—C14—C13B	172.2 (3)
S1—C4—C5—C6	−176.81 (16)	N2—N3—C9—C10	−157.6 (2)
S1—C4—C3—C2	176.45 (17)	C5—C4—C3—C2	−0.1 (3)
O3—C8—N2—N3	−179.2 (2)	C3—C4—C5—C6	−0.3 (3)
N1—S1—C4—C5	−58.35 (17)	C6—C1—C2—C3	0.9 (3)
N1—S1—C4—C3	125.08 (17)	C2—C1—C6—C5	−1.3 (3)
N1—C8—N2—N3	2.1 (3)	C14—N3—N2—C8	−115.4 (2)
N3—C14—C13A—C12A	−37.4 (8)	C14—N3—C9—C10	78.7 (3)
N3—C14—C13B—C12B	73.0 (7)	C14—C13A—C12A—C11	83.8 (8)
N3—C9—C10—C11	−77.3 (3)	C14—C13B—C12B—C11	−79.8 (9)
O1—S1—N1—C8	172.19 (17)	C9—N3—N2—C8	116.8 (2)
O1—S1—C4—C5	52.99 (18)	C9—N3—C14—C13A	−35.1 (5)
O1—S1—C4—C3	−123.58 (17)	C9—N3—C14—C13B	−63.7 (4)
O2—S1—N1—C8	42.9 (2)	C9—C10—C11—C12A	66.6 (4)
O2—S1—C4—C5	−176.49 (15)	C9—C10—C11—C12B	25.6 (6)
O2—S1—C4—C3	6.94 (19)	C10—C11—C12A—C13A	−76.4 (5)
C4—S1—N1—C8	−73.84 (19)	C10—C11—C12B—C13B	40.8 (8)
C4—C5—C6—C1	1.0 (3)	C7—C1—C6—C5	179.9 (2)
C4—C3—C2—C1	−0.3 (3)	C7—C1—C2—C3	179.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.79 (2)	2.47 (2)	3.105 (2)	138 (2)
N2—H2···O3^ii	0.81 (2)	2.23 (2)	3.036 (2)	172 (2)

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

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_II_250)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.339 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.4468 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0141 (5) Å	Cell parameters from 3177 reflections
c = 13.4850 (7) Å	θ = 3.4–24.7°
α = 82.360 (4)°	µ = 0.22 mm^−1
β = 85.368 (4)°	T = 250 K
γ = 85.553 (4)°	Plate, colourless
V = 772.38 (7) Å^3	0.45 × 0.3 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3154 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2336 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 3.4°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −11→11
Tmin = 0.837, Tmax = 1.000	l = −16→16
11517 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 0.0711P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.23 e Å^−3
3154 reflections	Δρmin = −0.41 e Å^−3
219 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.181 (10)
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
S1	0.25134 (8)	0.97358 (6)	0.39261 (4)	0.0295 (2)
O3	0.0624 (2)	0.67355 (17)	0.41274 (11)	0.0394 (4)
N1	0.2531 (3)	0.8333 (2)	0.48198 (14)	0.0302 (4)
N3	0.2886 (3)	0.6404 (2)	0.64546 (13)	0.0316 (4)
O1	0.3450 (2)	1.08930 (16)	0.43256 (12)	0.0383 (4)
O2	0.0484 (2)	1.00303 (17)	0.35714 (12)	0.0401 (4)
C8	0.1571 (3)	0.7008 (2)	0.48266 (16)	0.0295 (5)
C4	0.4212 (3)	0.9133 (2)	0.29460 (15)	0.0293 (5)
N2	0.1811 (3)	0.6040 (2)	0.56577 (14)	0.0418 (5)
C5	0.6261 (3)	0.8678 (2)	0.31261 (17)	0.0343 (5)
H5	0.6725	0.8641	0.3765	0.041*
C3	0.3512 (4)	0.9198 (3)	0.20008 (17)	0.0384 (6)
H3	0.2132	0.9507	0.1886	0.046*
C1	0.6953 (4)	0.8345 (3)	0.13850 (17)	0.0409 (6)
C6	0.7603 (4)	0.8280 (3)	0.23401 (18)	0.0400 (6)
H6	0.8978	0.7961	0.2458	0.048*
C2	0.4885 (4)	0.8797 (3)	0.12263 (18)	0.0456 (6)
H2A	0.4418	0.8831	0.0588	0.055*
C14	0.4793 (4)	0.5401 (3)	0.6543 (2)	0.0460 (6)
H14A	0.5827	0.5795	0.6034	0.055*	0.569 (7)
H14B	0.4476	0.4432	0.6378	0.055*	0.569 (7)
H14C	0.5578	0.5453	0.5896	0.055*	0.431 (7)
H14D	0.4411	0.4377	0.6731	0.055*	0.431 (7)
C9	0.1459 (4)	0.6421 (3)	0.73549 (18)	0.0445 (6)
H9A	0.1364	0.5403	0.7686	0.053*
H9B	0.0080	0.6793	0.7159	0.053*
C10	0.2144 (5)	0.7380 (3)	0.8082 (2)	0.0595 (8)
H10A	0.2589	0.8306	0.7702	0.071*
H10B	0.0936	0.7641	0.8517	0.071*
C7	0.8445 (5)	0.7890 (4)	0.0540 (2)	0.0659 (9)
H7A	0.8042	0.8434	−0.0084	0.099*
H7B	0.8408	0.6833	0.0515	0.099*
H7C	0.9832	0.8113	0.0652	0.099*
C11	0.3837 (5)	0.6742 (5)	0.8724 (2)	0.0808 (11)
H11C	0.3182	0.6378	0.9375	0.097*	0.431 (7)
H11D	0.4648	0.7566	0.8823	0.097*	0.431 (7)
H11A	0.3449	0.5795	0.9095	0.097*	0.569 (7)
H11B	0.4035	0.7421	0.9204	0.097*	0.569 (7)
C13A	0.5791 (10)	0.5139 (5)	0.7522 (4)	0.0450 (16)	0.569 (7)
H13A	0.7204	0.4717	0.7400	0.054*	0.569 (7)
H13B	0.5042	0.4387	0.7962	0.054*	0.569 (7)
C12A	0.5889 (6)	0.6491 (6)	0.8081 (4)	0.0489 (16)	0.569 (7)
H12A	0.6120	0.7377	0.7603	0.059*	0.569 (7)
H12B	0.7047	0.6326	0.8509	0.059*	0.569 (7)
C13B	0.6147 (11)	0.5805 (10)	0.7306 (4)	0.055 (2)	0.431 (7)
H13C	0.6345	0.6870	0.7162	0.066*	0.431 (7)
H13D	0.7505	0.5278	0.7213	0.066*	0.431 (7)
C12B	0.5390 (12)	0.5476 (7)	0.8409 (5)	0.077 (3)	0.431 (7)
H12C	0.6574	0.5375	0.8820	0.092*	0.431 (7)
H12D	0.4721	0.4535	0.8519	0.092*	0.431 (7)
H1	0.311 (3)	0.838 (2)	0.5275 (17)	0.025 (6)*
H2	0.124 (4)	0.527 (3)	0.5730 (19)	0.044 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0345 (3)	0.0254 (3)	0.0295 (3)	−0.0047 (2)	−0.0048 (2)	−0.0032 (2)
O3	0.0494 (10)	0.0357 (9)	0.0363 (9)	−0.0122 (8)	−0.0140 (8)	−0.0049 (7)
N1	0.0364 (10)	0.0323 (10)	0.0237 (10)	−0.0109 (8)	−0.0058 (8)	−0.0033 (8)
N3	0.0344 (10)	0.0352 (10)	0.0267 (10)	−0.0092 (8)	−0.0059 (8)	−0.0034 (8)
O1	0.0512 (9)	0.0266 (8)	0.0393 (9)	−0.0096 (7)	−0.0065 (7)	−0.0060 (7)
O2	0.0367 (9)	0.0388 (9)	0.0451 (10)	0.0021 (7)	−0.0106 (7)	−0.0042 (7)
C8	0.0318 (11)	0.0283 (11)	0.0296 (12)	−0.0060 (9)	−0.0020 (9)	−0.0057 (9)
C4	0.0355 (11)	0.0267 (11)	0.0258 (11)	−0.0089 (9)	−0.0038 (9)	0.0008 (9)
N2	0.0599 (13)	0.0319 (11)	0.0371 (12)	−0.0222 (10)	−0.0168 (10)	0.0023 (9)
C5	0.0376 (12)	0.0373 (12)	0.0295 (12)	−0.0103 (10)	−0.0033 (10)	−0.0044 (10)
C3	0.0402 (13)	0.0433 (14)	0.0320 (13)	−0.0095 (11)	−0.0075 (10)	0.0006 (10)
C1	0.0489 (14)	0.0399 (14)	0.0346 (13)	−0.0146 (12)	0.0058 (11)	−0.0053 (10)
C6	0.0349 (12)	0.0430 (14)	0.0432 (14)	−0.0085 (11)	0.0005 (10)	−0.0080 (11)
C2	0.0597 (16)	0.0534 (16)	0.0251 (12)	−0.0133 (13)	−0.0051 (11)	−0.0037 (11)
C14	0.0464 (14)	0.0416 (14)	0.0515 (16)	0.0026 (12)	−0.0075 (12)	−0.0120 (12)
C9	0.0367 (13)	0.0562 (16)	0.0378 (14)	−0.0034 (12)	0.0006 (10)	0.0026 (12)
C10	0.0760 (19)	0.0582 (18)	0.0440 (16)	−0.0001 (15)	0.0111 (14)	−0.0172 (14)
C7	0.0738 (19)	0.079 (2)	0.0450 (17)	−0.0130 (17)	0.0166 (15)	−0.0174 (15)
C11	0.088 (2)	0.111 (3)	0.052 (2)	−0.008 (2)	−0.0177 (17)	−0.033 (2)
C13A	0.043 (3)	0.035 (3)	0.057 (4)	−0.001 (3)	−0.014 (3)	0.000 (2)
C12A	0.046 (3)	0.056 (4)	0.049 (3)	−0.007 (2)	−0.010 (2)	−0.016 (3)
C13B	0.036 (4)	0.041 (5)	0.085 (6)	−0.003 (4)	−0.025 (4)	0.010 (4)
C12B	0.119 (7)	0.051 (5)	0.063 (5)	−0.002 (5)	−0.052 (5)	0.005 (4)

Geometric parameters (Å, º)

S1—N1	1.6266 (19)	C14—C13A	1.498 (4)
S1—O1	1.4290 (14)	C14—C13B	1.499 (5)
S1—O2	1.4226 (16)	C9—H9A	0.9700
S1—C4	1.762 (2)	C9—H9B	0.9700
O3—C8	1.224 (2)	C9—C10	1.502 (4)
N1—C8	1.386 (3)	C10—H10A	0.9700
N1—H1	0.75 (2)	C10—H10B	0.9700
N3—N2	1.411 (2)	C10—C11	1.482 (5)
N3—C14	1.472 (3)	C7—H7A	0.9600
N3—C9	1.464 (3)	C7—H7B	0.9600
C8—N2	1.337 (3)	C7—H7C	0.9600
C4—C5	1.383 (3)	C11—H11C	0.9700
C4—C3	1.379 (3)	C11—H11D	0.9700
N2—H2	0.80 (3)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C5—C6	1.381 (3)	C11—C12A	1.541 (5)
C3—H3	0.9300	C11—C12B	1.539 (6)
C3—C2	1.381 (3)	C13A—H13A	0.9700
C1—C6	1.379 (3)	C13A—H13B	0.9700
C1—C2	1.389 (3)	C13A—C12A	1.524 (5)
C1—C7	1.509 (3)	C12A—H12A	0.9700
C6—H6	0.9300	C12A—H12B	0.9700
C2—H2A	0.9300	C13B—H13C	0.9700
C14—H14A	0.9700	C13B—H13D	0.9700
C14—H14B	0.9700	C13B—C12B	1.526 (6)
C14—H14C	0.9700	C12B—H12C	0.9700
C14—H14D	0.9700	C12B—H12D	0.9700
N1—S1—C4	105.39 (10)	H9A—C9—H9B	107.8
O1—S1—N1	104.58 (9)	C10—C9—H9A	109.1
O1—S1—C4	108.36 (9)	C10—C9—H9B	109.1
O2—S1—N1	110.32 (9)	C9—C10—H10A	107.9
O2—S1—O1	119.18 (10)	C9—C10—H10B	107.9
O2—S1—C4	108.16 (10)	H10A—C10—H10B	107.2
S1—N1—H1	118.9 (17)	C11—C10—C9	117.5 (3)
C8—N1—S1	125.85 (16)	C11—C10—H10A	107.9
C8—N1—H1	115.2 (17)	C11—C10—H10B	107.9
N2—N3—C14	108.44 (18)	C1—C7—H7A	109.5
N2—N3—C9	109.61 (16)	C1—C7—H7B	109.5
C9—N3—C14	116.68 (19)	C1—C7—H7C	109.5
O3—C8—N1	123.1 (2)	H7A—C7—H7B	109.5
O3—C8—N2	123.05 (18)	H7A—C7—H7C	109.5
N2—C8—N1	113.84 (18)	H7B—C7—H7C	109.5
C5—C4—S1	119.29 (16)	C10—C11—H11C	107.1
C3—C4—S1	119.61 (18)	C10—C11—H11D	107.1
C3—C4—C5	121.0 (2)	C10—C11—H11A	109.5
N3—N2—H2	119.0 (18)	C10—C11—H11B	109.5
C8—N2—N3	121.39 (18)	C10—C11—C12A	110.5 (3)
C8—N2—H2	119.4 (18)	C10—C11—C12B	121.0 (3)
C4—C5—H5	120.6	H11C—C11—H11D	106.8
C6—C5—C4	118.8 (2)	H11A—C11—H11B	108.1
C6—C5—H5	120.6	C12A—C11—H11A	109.5
C4—C3—H3	120.4	C12A—C11—H11B	109.5
C4—C3—C2	119.2 (2)	C12B—C11—H11C	107.1
C2—C3—H3	120.4	C12B—C11—H11D	107.1
C6—C1—C2	118.5 (2)	C14—C13A—H13A	108.0
C6—C1—C7	120.6 (2)	C14—C13A—H13B	108.0
C2—C1—C7	120.9 (2)	C14—C13A—C12A	117.2 (4)
C5—C6—H6	119.2	H13A—C13A—H13B	107.2
C1—C6—C5	121.6 (2)	C12A—C13A—H13A	108.0
C1—C6—H6	119.2	C12A—C13A—H13B	108.0
C3—C2—C1	121.0 (2)	C11—C12A—H12A	109.6
C3—C2—H2A	119.5	C11—C12A—H12B	109.6
C1—C2—H2A	119.5	C13A—C12A—C11	110.1 (4)
N3—C14—H14A	107.6	C13A—C12A—H12A	109.6
N3—C14—H14B	107.6	C13A—C12A—H12B	109.6
N3—C14—H14C	109.2	H12A—C12A—H12B	108.1
N3—C14—H14D	109.2	C14—C13B—H13C	107.9
N3—C14—C13A	119.1 (3)	C14—C13B—H13D	107.9
N3—C14—C13B	112.2 (4)	C14—C13B—C12B	117.6 (5)
H14A—C14—H14B	107.0	H13C—C13B—H13D	107.2
H14C—C14—H14D	107.9	C12B—C13B—H13C	107.9
C13A—C14—H14A	107.6	C12B—C13B—H13D	107.9
C13A—C14—H14B	107.6	C11—C12B—H12C	109.5
C13B—C14—H14C	109.2	C11—C12B—H12D	109.5
C13B—C14—H14D	109.2	C13B—C12B—C11	110.8 (6)
N3—C9—H9A	109.1	C13B—C12B—H12C	109.5
N3—C9—H9B	109.1	C13B—C12B—H12D	109.5
N3—C9—C10	112.70 (19)	H12C—C12B—H12D	108.1
S1—N1—C8—O3	1.9 (3)	N2—N3—C14—C13A	−157.5 (3)
S1—N1—C8—N2	−179.47 (17)	N2—N3—C14—C13B	174.3 (3)
S1—C4—C5—C6	−176.80 (16)	N2—N3—C9—C10	−156.1 (2)
S1—C4—C3—C2	176.63 (17)	C5—C4—C3—C2	0.1 (3)
O3—C8—N2—N3	−179.0 (2)	C3—C4—C5—C6	−0.3 (3)
N1—S1—C4—C5	−57.69 (18)	C6—C1—C2—C3	1.0 (3)
N1—S1—C4—C3	125.74 (17)	C2—C1—C6—C5	−1.2 (3)
N1—C8—N2—N3	2.3 (3)	C14—N3—N2—C8	−114.4 (2)
N3—C14—C13A—C12A	−41.1 (6)	C14—N3—C9—C10	80.2 (3)
N3—C14—C13B—C12B	71.6 (7)	C14—C13A—C12A—C11	84.9 (6)
N3—C9—C10—C11	−78.5 (3)	C14—C13B—C12B—C11	−83.1 (9)
O1—S1—N1—C8	172.25 (18)	C9—N3—N2—C8	117.2 (2)
O1—S1—C4—C5	53.81 (18)	C9—N3—C14—C13A	−33.2 (4)
O1—S1—C4—C3	−122.77 (17)	C9—N3—C14—C13B	−61.4 (4)
O2—S1—N1—C8	42.9 (2)	C9—C10—C11—C12A	65.1 (4)
O2—S1—C4—C5	−175.68 (15)	C9—C10—C11—C12B	23.2 (6)
O2—S1—C4—C3	7.7 (2)	C10—C11—C12A—C13A	−74.0 (5)
C4—S1—N1—C8	−73.6 (2)	C10—C11—C12B—C13B	44.8 (7)
C4—C5—C6—C1	0.8 (3)	C7—C1—C6—C5	−179.4 (2)
C4—C3—C2—C1	−0.5 (3)	C7—C1—C2—C3	179.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.75 (2)	2.48 (2)	3.083 (2)	139 (2)
N2—H2···O3^ii	0.80 (3)	2.22 (3)	3.025 (2)	174 (3)

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

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_II_200)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.352 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.3939 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9809 (4) Å	Cell parameters from 3525 reflections
c = 13.5213 (7) Å	θ = 3.5–28.1°
α = 82.129 (4)°	µ = 0.23 mm^−1
β = 85.602 (4)°	T = 200 K
γ = 85.341 (4)°	Plate, colourless
V = 764.89 (6) Å^3	0.45 × 0.3 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3115 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2445 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 3.5°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −11→11
Tmin = 0.805, Tmax = 1.000	l = −16→16
11396 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.2748P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.113	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.31 e Å^−3
3115 reflections	Δρmin = −0.39 e Å^−3
219 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.204 (10)
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
S1	0.25003 (8)	0.97551 (5)	0.39271 (4)	0.02195 (18)
O3	0.0614 (2)	0.67424 (16)	0.41253 (11)	0.0293 (4)
N1	0.2539 (3)	0.83399 (19)	0.48239 (13)	0.0230 (4)
N3	0.2901 (3)	0.63872 (19)	0.64548 (12)	0.0239 (4)
O1	0.3451 (2)	1.09162 (15)	0.43245 (11)	0.0284 (4)
O2	0.0444 (2)	1.00584 (16)	0.35743 (11)	0.0298 (4)
C8	0.1571 (3)	0.7010 (2)	0.48257 (15)	0.0230 (4)
C4	0.4199 (3)	0.9149 (2)	0.29486 (14)	0.0219 (4)
N2	0.1829 (3)	0.6027 (2)	0.56549 (14)	0.0317 (5)
C5	0.6271 (3)	0.8667 (2)	0.31273 (16)	0.0259 (5)
H5	0.6746	0.8616	0.3765	0.031*
C3	0.3473 (3)	0.9234 (2)	0.20016 (15)	0.0279 (5)
H3	0.2083	0.9557	0.1888	0.033*
C1	0.6940 (3)	0.8350 (2)	0.13837 (16)	0.0310 (5)
C6	0.7616 (3)	0.8264 (2)	0.23425 (17)	0.0302 (5)
H6	0.9001	0.7928	0.2459	0.036*
C2	0.4856 (4)	0.8829 (3)	0.12266 (16)	0.0329 (5)
H2A	0.4380	0.8878	0.0589	0.039*
C14	0.4860 (4)	0.5399 (3)	0.65347 (18)	0.0342 (5)
H14A	0.5905	0.5834	0.6045	0.041*	0.725 (7)
H14B	0.4585	0.4434	0.6344	0.041*	0.725 (7)
H14C	0.5676	0.5506	0.5897	0.041*	0.275 (7)
H14D	0.4513	0.4357	0.6689	0.041*	0.275 (7)
C9	0.1465 (3)	0.6377 (3)	0.73567 (16)	0.0328 (5)
H9A	0.1432	0.5353	0.7694	0.039*
H9B	0.0056	0.6708	0.7161	0.039*
C10	0.2100 (4)	0.7378 (3)	0.80741 (18)	0.0420 (6)
H10A	0.2487	0.8319	0.7689	0.050*
H10B	0.0876	0.7609	0.8511	0.050*
C7	0.8432 (4)	0.7892 (3)	0.0541 (2)	0.0498 (7)
H7A	0.7999	0.8425	−0.0083	0.075*
H7B	0.8417	0.6827	0.0527	0.075*
H7C	0.9828	0.8133	0.0644	0.075*
C11	0.3866 (5)	0.6779 (4)	0.8716 (2)	0.0527 (7)
H11C	0.3255	0.6489	0.9387	0.063*	0.275 (7)
H11D	0.4730	0.7607	0.8750	0.063*	0.275 (7)
H11A	0.3484	0.5854	0.9125	0.063*	0.725 (7)
H11B	0.4084	0.7504	0.9161	0.063*	0.725 (7)
C13A	0.5821 (7)	0.5103 (4)	0.7531 (3)	0.0337 (10)	0.725 (7)
H13A	0.7239	0.4652	0.7428	0.040*	0.725 (7)
H13B	0.5025	0.4363	0.7960	0.040*	0.725 (7)
C12A	0.5932 (5)	0.6462 (4)	0.8090 (3)	0.0385 (11)	0.725 (7)
H12A	0.6210	0.7342	0.7611	0.046*	0.725 (7)
H12B	0.7085	0.6273	0.8527	0.046*	0.725 (7)
C13B	0.6160 (14)	0.5780 (14)	0.7336 (5)	0.040 (3)	0.275 (7)
H13C	0.6363	0.6850	0.7202	0.048*	0.275 (7)
H13D	0.7535	0.5251	0.7261	0.048*	0.275 (7)
C12B	0.5347 (15)	0.5439 (9)	0.8431 (7)	0.058 (4)	0.275 (7)
H12C	0.6520	0.5279	0.8857	0.070*	0.275 (7)
H12D	0.4595	0.4529	0.8524	0.070*	0.275 (7)
H1	0.310 (4)	0.843 (3)	0.5265 (18)	0.021 (6)*
H2	0.124 (4)	0.521 (3)	0.5725 (18)	0.032 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0257 (3)	0.0191 (3)	0.0214 (3)	−0.00313 (19)	−0.00344 (19)	−0.00231 (19)
O3	0.0365 (9)	0.0270 (8)	0.0266 (8)	−0.0077 (7)	−0.0107 (7)	−0.0042 (6)
N1	0.0287 (10)	0.0239 (9)	0.0182 (9)	−0.0075 (7)	−0.0051 (8)	−0.0036 (7)
N3	0.0272 (9)	0.0264 (9)	0.0191 (9)	−0.0062 (7)	−0.0045 (7)	−0.0029 (7)
O1	0.0380 (8)	0.0200 (7)	0.0286 (8)	−0.0064 (6)	−0.0042 (6)	−0.0044 (6)
O2	0.0283 (8)	0.0295 (8)	0.0315 (8)	0.0018 (6)	−0.0067 (6)	−0.0036 (6)
C8	0.0241 (10)	0.0224 (10)	0.0232 (10)	−0.0038 (8)	−0.0005 (8)	−0.0047 (8)
C4	0.0270 (10)	0.0196 (10)	0.0193 (10)	−0.0070 (8)	−0.0013 (8)	−0.0004 (8)
N2	0.0458 (12)	0.0232 (10)	0.0288 (10)	−0.0159 (9)	−0.0128 (8)	0.0004 (8)
C5	0.0285 (11)	0.0268 (11)	0.0233 (11)	−0.0060 (9)	−0.0033 (8)	−0.0034 (8)
C3	0.0309 (11)	0.0287 (11)	0.0239 (11)	−0.0041 (9)	−0.0063 (9)	0.0009 (9)
C1	0.0367 (12)	0.0303 (12)	0.0265 (12)	−0.0116 (10)	0.0053 (9)	−0.0040 (9)
C6	0.0271 (11)	0.0317 (12)	0.0321 (12)	−0.0058 (9)	0.0008 (9)	−0.0049 (9)
C2	0.0447 (14)	0.0357 (12)	0.0197 (11)	−0.0102 (11)	−0.0040 (9)	−0.0030 (9)
C14	0.0357 (12)	0.0311 (12)	0.0366 (13)	0.0011 (10)	−0.0036 (10)	−0.0084 (10)
C9	0.0275 (11)	0.0419 (13)	0.0270 (12)	−0.0031 (10)	0.0003 (9)	0.0019 (10)
C10	0.0522 (15)	0.0408 (14)	0.0323 (13)	0.0016 (12)	0.0072 (11)	−0.0111 (11)
C7	0.0543 (16)	0.0620 (18)	0.0334 (14)	−0.0087 (14)	0.0125 (12)	−0.0126 (13)
C11	0.0591 (17)	0.0666 (19)	0.0380 (15)	−0.0055 (15)	−0.0086 (13)	−0.0231 (14)
C13A	0.031 (2)	0.027 (2)	0.044 (2)	−0.0008 (17)	−0.0090 (16)	−0.0023 (16)
C12A	0.0355 (19)	0.044 (2)	0.039 (2)	−0.0081 (16)	−0.0081 (15)	−0.0097 (17)
C13B	0.029 (5)	0.030 (6)	0.060 (7)	−0.005 (5)	−0.021 (5)	0.007 (5)
C12B	0.080 (8)	0.046 (7)	0.052 (7)	−0.009 (6)	−0.037 (6)	0.002 (5)

Geometric parameters (Å, º)

S1—N1	1.6321 (18)	C14—C13A	1.506 (4)
S1—O1	1.4324 (14)	C14—C13B	1.506 (5)
S1—O2	1.4260 (15)	C9—H9A	0.9700
S1—C4	1.763 (2)	C9—H9B	0.9700
O3—C8	1.227 (2)	C9—C10	1.508 (3)
N1—C8	1.388 (2)	C10—H10A	0.9700
N1—H1	0.74 (2)	C10—H10B	0.9700
N3—N2	1.411 (2)	C10—C11	1.497 (4)
N3—C14	1.477 (3)	C7—H7A	0.9600
N3—C9	1.469 (3)	C7—H7B	0.9600
C8—N2	1.341 (3)	C7—H7C	0.9600
C4—C5	1.388 (3)	C11—H11C	0.9700
C4—C3	1.385 (3)	C11—H11D	0.9700
N2—H2	0.84 (2)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C5—C6	1.383 (3)	C11—C12A	1.541 (4)
C3—H3	0.9300	C11—C12B	1.543 (6)
C3—C2	1.387 (3)	C13A—H13A	0.9700
C1—C6	1.388 (3)	C13A—H13B	0.9700
C1—C2	1.389 (3)	C13A—C12A	1.530 (4)
C1—C7	1.508 (3)	C12A—H12A	0.9700
C6—H6	0.9300	C12A—H12B	0.9700
C2—H2A	0.9300	C13B—H13C	0.9700
C14—H14A	0.9700	C13B—H13D	0.9700
C14—H14B	0.9700	C13B—C12B	1.530 (6)
C14—H14C	0.9700	C12B—H12C	0.9700
C14—H14D	0.9700	C12B—H12D	0.9700
N1—S1—C4	105.32 (9)	H9A—C9—H9B	107.8
O1—S1—N1	104.43 (9)	C10—C9—H9A	109.1
O1—S1—C4	108.46 (9)	C10—C9—H9B	109.1
O2—S1—N1	110.52 (9)	C9—C10—H10A	108.0
O2—S1—O1	119.11 (9)	C9—C10—H10B	108.0
O2—S1—C4	108.16 (9)	H10A—C10—H10B	107.3
S1—N1—H1	116.5 (18)	C11—C10—C9	117.1 (2)
C8—N1—S1	125.34 (15)	C11—C10—H10A	108.0
C8—N1—H1	118.1 (18)	C11—C10—H10B	108.0
N2—N3—C14	108.30 (16)	C1—C7—H7A	109.5
N2—N3—C9	109.80 (16)	C1—C7—H7B	109.5
C9—N3—C14	116.96 (17)	C1—C7—H7C	109.5
O3—C8—N1	123.29 (19)	H7A—C7—H7B	109.5
O3—C8—N2	123.02 (18)	H7A—C7—H7C	109.5
N2—C8—N1	113.67 (17)	H7B—C7—H7C	109.5
C5—C4—S1	119.46 (15)	C10—C11—H11C	107.4
C3—C4—S1	119.37 (16)	C10—C11—H11D	107.4
C3—C4—C5	121.1 (2)	C10—C11—H11A	109.2
N3—N2—H2	118.8 (16)	C10—C11—H11B	109.2
C8—N2—N3	121.41 (17)	C10—C11—C12A	112.1 (2)
C8—N2—H2	119.5 (16)	C10—C11—C12B	119.7 (4)
C4—C5—H5	120.5	H11C—C11—H11D	106.9
C6—C5—C4	119.0 (2)	H11A—C11—H11B	107.9
C6—C5—H5	120.5	C12A—C11—H11A	109.2
C4—C3—H3	120.6	C12A—C11—H11B	109.2
C4—C3—C2	118.8 (2)	C12B—C11—H11C	107.4
C2—C3—H3	120.6	C12B—C11—H11D	107.4
C6—C1—C2	118.6 (2)	C14—C13A—H13A	108.1
C6—C1—C7	120.3 (2)	C14—C13A—H13B	108.1
C2—C1—C7	121.1 (2)	C14—C13A—C12A	116.8 (3)
C5—C6—C1	121.3 (2)	H13A—C13A—H13B	107.3
C5—C6—H6	119.4	C12A—C13A—H13A	108.1
C1—C6—H6	119.4	C12A—C13A—H13B	108.1
C3—C2—C1	121.3 (2)	C11—C12A—H12A	109.3
C3—C2—H2A	119.4	C11—C12A—H12B	109.3
C1—C2—H2A	119.4	C13A—C12A—C11	111.5 (3)
N3—C14—H14A	107.8	C13A—C12A—H12A	109.3
N3—C14—H14B	107.8	C13A—C12A—H12B	109.3
N3—C14—H14C	109.3	H12A—C12A—H12B	108.0
N3—C14—H14D	109.3	C14—C13B—H13C	107.6
N3—C14—C13A	118.1 (2)	C14—C13B—H13D	107.6
N3—C14—C13B	111.4 (5)	C14—C13B—C12B	118.7 (7)
H14A—C14—H14B	107.1	H13C—C13B—H13D	107.1
H14C—C14—H14D	108.0	C12B—C13B—H13C	107.6
C13A—C14—H14A	107.8	C12B—C13B—H13D	107.6
C13A—C14—H14B	107.8	C11—C12B—H12C	109.9
C13B—C14—H14C	109.3	C11—C12B—H12D	109.9
C13B—C14—H14D	109.3	C13B—C12B—C11	109.1 (7)
N3—C9—H9A	109.1	C13B—C12B—H12C	109.9
N3—C9—H9B	109.1	C13B—C12B—H12D	109.9
N3—C9—C10	112.65 (17)	H12C—C12B—H12D	108.3
S1—N1—C8—O3	2.0 (3)	N2—N3—C14—C13A	−155.8 (2)
S1—N1—C8—N2	−179.65 (16)	N2—N3—C14—C13B	176.6 (4)
S1—C4—C5—C6	−176.87 (15)	N2—N3—C9—C10	−154.20 (19)
S1—C4—C3—C2	176.63 (15)	C5—C4—C3—C2	0.0 (3)
O3—C8—N2—N3	−178.61 (19)	C3—C4—C5—C6	−0.2 (3)
N1—S1—C4—C5	−56.79 (17)	C6—C1—C2—C3	0.9 (3)
N1—S1—C4—C3	126.50 (16)	C2—C1—C6—C5	−1.1 (3)
N1—C8—N2—N3	3.1 (3)	C14—N3—N2—C8	−113.7 (2)
N3—C14—C13A—C12A	−44.3 (4)	C14—N3—C9—C10	81.9 (2)
N3—C14—C13B—C12B	69.2 (9)	C14—C13A—C12A—C11	85.2 (4)
N3—C9—C10—C11	−78.3 (3)	C14—C13B—C12B—C11	−86.3 (11)
O1—S1—N1—C8	172.44 (17)	C9—N3—N2—C8	117.5 (2)
O1—S1—C4—C5	54.55 (17)	C9—N3—C14—C13A	−31.1 (3)
O1—S1—C4—C3	−122.17 (16)	C9—N3—C14—C13B	−58.8 (4)
O2—S1—N1—C8	43.2 (2)	C9—C10—C11—C12A	61.2 (3)
O2—S1—C4—C5	−174.97 (14)	C9—C10—C11—C12B	17.3 (6)
O2—S1—C4—C3	8.31 (19)	C10—C11—C12A—C13A	−70.4 (4)
C4—S1—N1—C8	−73.39 (18)	C10—C11—C12B—C13B	51.2 (8)
C4—C5—C6—C1	0.8 (3)	C7—C1—C6—C5	−179.5 (2)
C4—C3—C2—C1	−0.3 (3)	C7—C1—C2—C3	179.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.74 (2)	2.45 (2)	3.048 (2)	140 (2)
N2—H2···O3^ii	0.84 (2)	2.17 (3)	3.011 (2)	173 (2)

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

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_II_150)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.367 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.3358 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9455 (11) Å	Cell parameters from 2355 reflections
c = 13.5482 (15) Å	θ = 3.5–27.8°
α = 81.976 (10)°	µ = 0.23 mm^−1
β = 85.919 (10)°	T = 150 K
γ = 85.273 (10)°	Plate, colourless
V = 756.38 (15) Å^3	0.45 × 0.3 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3073 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2345 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 3.5°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −11→11
Tmin = 0.949, Tmax = 1.000	l = −16→16
10897 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.3381P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.127	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.31 e Å^−3
3073 reflections	Δρmin = −0.47 e Å^−3
209 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.122 (7)
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
S1	0.24890 (9)	0.97737 (6)	0.39267 (4)	0.0186 (2)
O3	0.0600 (3)	0.67520 (18)	0.41208 (13)	0.0238 (4)
N1	0.2543 (3)	0.8355 (2)	0.48205 (16)	0.0193 (5)
N3	0.2923 (3)	0.6364 (2)	0.64536 (15)	0.0201 (5)
O1	0.3453 (3)	1.09391 (18)	0.43196 (13)	0.0235 (4)
O2	0.0407 (3)	1.00828 (18)	0.35765 (13)	0.0238 (4)
C8	0.1574 (4)	0.7010 (3)	0.48249 (18)	0.0187 (5)
C4	0.4182 (4)	0.9163 (2)	0.29485 (18)	0.0184 (5)
N2	0.1842 (4)	0.6016 (2)	0.56488 (16)	0.0254 (5)
C5	0.6273 (4)	0.8658 (3)	0.31301 (19)	0.0215 (5)
H5	0.6761	0.8594	0.3767	0.026*
C3	0.3439 (4)	0.9271 (3)	0.20033 (18)	0.0223 (6)
H3	0.2040	0.9615	0.1890	0.027*
C1	0.6921 (4)	0.8355 (3)	0.13836 (19)	0.0250 (6)
C6	0.7612 (4)	0.8253 (3)	0.23417 (19)	0.0242 (6)
H6	0.9008	0.7903	0.2458	0.029*
C2	0.4824 (4)	0.8856 (3)	0.12238 (19)	0.0253 (6)
H2A	0.4335	0.8916	0.0587	0.030*
C14	0.4928 (4)	0.5390 (3)	0.6529 (2)	0.0257 (6)
H14A	0.5982	0.5856	0.6057	0.031*	0.904 (7)
H14B	0.4688	0.4426	0.6321	0.031*	0.904 (7)
H14C	0.5775	0.5536	0.5903	0.031*	0.096 (7)
H14D	0.4619	0.4334	0.6666	0.031*	0.096 (7)
C9	0.1465 (4)	0.6327 (3)	0.73527 (19)	0.0253 (6)
H9A	0.1475	0.5298	0.7693	0.030*
H9B	0.0035	0.6630	0.7154	0.030*
C10	0.2061 (4)	0.7360 (3)	0.8070 (2)	0.0301 (6)
H10A	0.2396	0.8318	0.7685	0.036*
H10B	0.0825	0.7560	0.8510	0.036*
C7	0.8416 (5)	0.7887 (3)	0.0541 (2)	0.0369 (7)
H7A	0.7904	0.8354	−0.0087	0.055*
H7B	0.8490	0.6806	0.0566	0.055*
H7C	0.9804	0.8203	0.0610	0.055*
C11	0.3899 (5)	0.6793 (3)	0.8710 (2)	0.0356 (7)
H11C	0.3339	0.6566	0.9395	0.043*	0.096 (7)
H11D	0.4822	0.7611	0.8688	0.043*	0.096 (7)
H11A	0.3524	0.5888	0.9147	0.043*	0.904 (7)
H11B	0.4133	0.7554	0.9127	0.043*	0.904 (7)
C13A	0.5849 (5)	0.5079 (4)	0.7538 (2)	0.0274 (8)	0.904 (7)
H13A	0.7274	0.4609	0.7453	0.033*	0.904 (7)
H13B	0.5015	0.4345	0.7955	0.033*	0.904 (7)
C12A	0.5968 (5)	0.6431 (3)	0.8104 (2)	0.0310 (9)	0.904 (7)
H12A	0.6291	0.7311	0.7631	0.037*	0.904 (7)
H12B	0.7116	0.6217	0.8552	0.037*	0.904 (7)
C13B	0.614 (4)	0.580 (4)	0.7359 (12)	0.026 (8)*	0.096 (7)
H13C	0.6267	0.6882	0.7242	0.031*	0.096 (7)
H13D	0.7560	0.5314	0.7304	0.031*	0.096 (7)
C12B	0.525 (4)	0.5397 (17)	0.8434 (17)	0.033 (9)*	0.096 (7)
H12C	0.6403	0.5142	0.8879	0.040*	0.096 (7)
H12D	0.4397	0.4536	0.8486	0.040*	0.096 (7)
H1	0.311 (5)	0.841 (3)	0.529 (2)	0.029 (8)*
H2	0.129 (4)	0.521 (3)	0.571 (2)	0.030 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0228 (3)	0.0136 (3)	0.0200 (3)	−0.0030 (2)	−0.0025 (2)	−0.0029 (2)
O3	0.0294 (10)	0.0205 (9)	0.0237 (10)	−0.0070 (8)	−0.0064 (8)	−0.0047 (7)
N1	0.0246 (11)	0.0171 (11)	0.0183 (11)	−0.0075 (9)	−0.0041 (9)	−0.0041 (8)
N3	0.0213 (10)	0.0212 (11)	0.0191 (11)	−0.0051 (9)	−0.0015 (8)	−0.0052 (8)
O1	0.0326 (10)	0.0139 (8)	0.0254 (10)	−0.0062 (7)	−0.0036 (8)	−0.0040 (7)
O2	0.0233 (9)	0.0211 (9)	0.0271 (10)	0.0010 (7)	−0.0041 (7)	−0.0038 (7)
C8	0.0199 (12)	0.0146 (12)	0.0222 (13)	−0.0015 (10)	0.0007 (10)	−0.0051 (10)
C4	0.0225 (12)	0.0117 (11)	0.0206 (13)	−0.0050 (10)	−0.0011 (10)	0.0008 (9)
N2	0.0378 (13)	0.0168 (11)	0.0239 (12)	−0.0120 (10)	−0.0091 (10)	−0.0012 (9)
C5	0.0252 (13)	0.0181 (12)	0.0220 (13)	−0.0063 (10)	−0.0024 (10)	−0.0024 (10)
C3	0.0245 (13)	0.0190 (12)	0.0233 (14)	−0.0046 (10)	−0.0047 (10)	0.0007 (10)
C1	0.0302 (14)	0.0182 (13)	0.0267 (14)	−0.0082 (11)	0.0046 (11)	−0.0030 (10)
C6	0.0235 (13)	0.0206 (13)	0.0290 (14)	−0.0044 (11)	0.0001 (11)	−0.0040 (11)
C2	0.0350 (15)	0.0248 (13)	0.0172 (13)	−0.0086 (12)	−0.0027 (11)	−0.0021 (10)
C14	0.0278 (14)	0.0219 (13)	0.0289 (14)	−0.0030 (11)	−0.0013 (11)	−0.0077 (11)
C9	0.0231 (13)	0.0276 (14)	0.0246 (14)	−0.0043 (11)	−0.0003 (10)	−0.0012 (11)
C10	0.0335 (15)	0.0280 (14)	0.0289 (15)	0.0006 (12)	0.0028 (12)	−0.0082 (11)
C7	0.0414 (17)	0.0422 (17)	0.0266 (15)	−0.0029 (14)	0.0070 (13)	−0.0082 (13)
C11	0.0406 (16)	0.0396 (17)	0.0297 (16)	−0.0049 (14)	−0.0050 (13)	−0.0133 (13)
C13A	0.0235 (16)	0.0214 (17)	0.0369 (19)	0.0007 (14)	−0.0061 (13)	−0.0012 (13)
C12A	0.0298 (17)	0.0321 (18)	0.0335 (19)	−0.0038 (14)	−0.0085 (13)	−0.0084 (14)

Geometric parameters (Å, º)

S1—N1	1.627 (2)	C14—C13A	1.506 (4)
S1—O1	1.4316 (16)	C14—C13B	1.506 (6)
S1—O2	1.4259 (18)	C9—H9A	0.9700
S1—C4	1.763 (3)	C9—H9B	0.9700
O3—C8	1.230 (3)	C9—C10	1.518 (4)
N1—C8	1.395 (3)	C10—H10A	0.9700
N1—H1	0.76 (3)	C10—H10B	0.9700
N3—N2	1.411 (3)	C10—C11	1.513 (4)
N3—C14	1.481 (3)	C7—H7A	0.9600
N3—C9	1.474 (3)	C7—H7B	0.9600
C8—N2	1.338 (3)	C7—H7C	0.9600
C4—C5	1.391 (3)	C11—H11C	0.9700
C4—C3	1.384 (3)	C11—H11D	0.9700
N2—H2	0.82 (3)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C5—C6	1.386 (3)	C11—C12A	1.532 (4)
C3—H3	0.9300	C11—C12B	1.532 (6)
C3—C2	1.395 (4)	C13A—H13A	0.9700
C1—C6	1.388 (4)	C13A—H13B	0.9700
C1—C2	1.389 (4)	C13A—C12A	1.529 (4)
C1—C7	1.513 (4)	C12A—H12A	0.9700
C6—H6	0.9300	C12A—H12B	0.9700
C2—H2A	0.9300	C13B—H13C	0.9700
C14—H14A	0.9700	C13B—H13D	0.9700
C14—H14B	0.9700	C13B—C12B	1.528 (6)
C14—H14C	0.9700	C12B—H12C	0.9700
C14—H14D	0.9700	C12B—H12D	0.9700
N1—S1—C4	105.29 (11)	H9A—C9—H9B	107.8
O1—S1—N1	104.48 (10)	C10—C9—H9A	109.1
O1—S1—C4	108.61 (10)	C10—C9—H9B	109.1
O2—S1—N1	110.59 (10)	C9—C10—H10A	108.1
O2—S1—O1	118.97 (10)	C9—C10—H10B	108.1
O2—S1—C4	108.07 (11)	H10A—C10—H10B	107.3
S1—N1—H1	120 (2)	C11—C10—C9	116.7 (2)
C8—N1—S1	125.48 (18)	C11—C10—H10A	108.1
C8—N1—H1	115 (2)	C11—C10—H10B	108.1
N2—N3—C14	108.65 (18)	C1—C7—H7A	109.5
N2—N3—C9	109.51 (18)	C1—C7—H7B	109.5
C9—N3—C14	117.3 (2)	C1—C7—H7C	109.5
O3—C8—N1	122.6 (2)	H7A—C7—H7B	109.5
O3—C8—N2	123.2 (2)	H7A—C7—H7C	109.5
N2—C8—N1	114.2 (2)	H7B—C7—H7C	109.5
C5—C4—S1	119.30 (18)	C10—C11—H11C	108.1
C3—C4—S1	119.32 (19)	C10—C11—H11D	108.1
C3—C4—C5	121.3 (2)	C10—C11—H11A	108.9
N3—N2—H2	119 (2)	C10—C11—H11B	108.9
C8—N2—N3	121.7 (2)	C10—C11—C12A	113.5 (2)
C8—N2—H2	119 (2)	C10—C11—C12B	117.0 (11)
C4—C5—H5	120.7	H11C—C11—H11D	107.3
C6—C5—C4	118.6 (2)	H11A—C11—H11B	107.7
C6—C5—H5	120.7	C12A—C11—H11A	108.9
C4—C3—H3	120.6	C12A—C11—H11B	108.9
C4—C3—C2	118.9 (2)	C12B—C11—H11C	108.1
C2—C3—H3	120.6	C12B—C11—H11D	108.1
C6—C1—C2	118.6 (2)	C14—C13A—H13A	108.0
C6—C1—C7	120.3 (2)	C14—C13A—H13B	108.0
C2—C1—C7	121.1 (2)	C14—C13A—C12A	117.2 (3)
C5—C6—C1	121.6 (2)	H13A—C13A—H13B	107.2
C5—C6—H6	119.2	C12A—C13A—H13A	108.0
C1—C6—H6	119.2	C12A—C13A—H13B	108.0
C3—C2—H2A	119.5	C11—C12A—H12A	109.1
C1—C2—C3	121.0 (2)	C11—C12A—H12B	109.1
C1—C2—H2A	119.5	C13A—C12A—C11	112.6 (2)
N3—C14—H14A	108.1	C13A—C12A—H12A	109.1
N3—C14—H14B	108.1	C13A—C12A—H12B	109.1
N3—C14—H14C	109.9	H12A—C12A—H12B	107.8
N3—C14—H14D	109.9	C14—C13B—H13C	107.7
N3—C14—C13A	116.9 (2)	C14—C13B—H13D	107.7
N3—C14—C13B	109.1 (13)	C14—C13B—C12B	118.3 (17)
H14A—C14—H14B	107.3	H13C—C13B—H13D	107.1
H14C—C14—H14D	108.3	C12B—C13B—H13C	107.7
C13A—C14—H14A	108.1	C12B—C13B—H13D	107.7
C13A—C14—H14B	108.1	C11—C12B—H12C	110.4
C13B—C14—H14C	109.9	C11—C12B—H12D	110.4
C13B—C14—H14D	109.9	C13B—C12B—C11	106.8 (16)
N3—C9—H9A	109.1	C13B—C12B—H12C	110.4
N3—C9—H9B	109.1	C13B—C12B—H12D	110.4
N3—C9—C10	112.45 (19)	H12C—C12B—H12D	108.6
S1—N1—C8—O3	1.7 (3)	N2—N3—C14—C13A	−154.8 (2)
S1—N1—C8—N2	−179.79 (18)	N2—N3—C14—C13B	177.7 (11)
S1—C4—C5—C6	−176.84 (17)	N2—N3—C9—C10	−152.5 (2)
S1—C4—C3—C2	176.79 (17)	C5—C4—C3—C2	0.3 (3)
O3—C8—N2—N3	−178.4 (2)	C3—C4—C5—C6	−0.4 (3)
N1—S1—C4—C5	−56.1 (2)	C6—C1—C2—C3	0.9 (3)
N1—S1—C4—C3	127.41 (18)	C2—C1—C6—C5	−1.0 (3)
N1—C8—N2—N3	3.2 (3)	C14—N3—N2—C8	−112.8 (3)
N3—C14—C13A—C12A	−46.6 (4)	C14—N3—C9—C10	83.1 (3)
N3—C14—C13B—C12B	70 (2)	C14—C13A—C12A—C11	85.3 (4)
N3—C9—C10—C11	−77.5 (3)	C14—C13B—C12B—C11	−94 (3)
O1—S1—N1—C8	172.8 (2)	C9—N3—N2—C8	117.8 (3)
O1—S1—C4—C5	55.4 (2)	C9—N3—C14—C13A	−30.0 (3)
O1—S1—C4—C3	−121.15 (18)	C9—N3—C14—C13B	−57.5 (11)
O2—S1—N1—C8	43.7 (2)	C9—C10—C11—C12A	57.9 (3)
O2—S1—C4—C5	−174.27 (17)	C9—C10—C11—C12B	11.8 (11)
O2—S1—C4—C3	9.2 (2)	C10—C11—C12A—C13A	−66.9 (3)
C4—S1—N1—C8	−72.8 (2)	C10—C11—C12B—C13B	58.7 (18)
C4—C5—C6—C1	0.7 (3)	C7—C1—C6—C5	−179.3 (2)
C4—C3—C2—C1	−0.6 (3)	C7—C1—C2—C3	179.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.76 (3)	2.41 (3)	3.013 (3)	137 (3)
N2—H2···O3^ii	0.82 (3)	2.18 (3)	2.995 (3)	172 (3)

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

1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_II_100)

Crystal data

C14H21N3O3S	F(000) = 332
Mr = 311.40	Dx = 1.373 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 6.3091 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9270 (15) Å	Cell parameters from 1573 reflections
c = 13.576 (3) Å	θ = 3.5–28.6°
α = 81.882 (16)°	µ = 0.23 mm^−1
β = 86.073 (16)°	T = 100 K
γ = 85.167 (13)°	Plate, colourless
V = 753.0 (2) Å^3	0.45 × 0.3 × 0.05 mm
Z = 2

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3057 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2081 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 3.5°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −11→11
Tmin = 0.753, Tmax = 1.000	l = −16→16
10088 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.069	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 0.2853P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.173	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.47 e Å^−3
3057 reflections	Δρmin = −0.63 e Å^−3
200 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.054 (6)
Primary atom site location: structure-invariant direct methods

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
S1	0.24796 (13)	0.97848 (9)	0.39256 (6)	0.0193 (3)
O3	0.0587 (3)	0.6762 (2)	0.41186 (17)	0.0220 (6)
N1	0.2545 (4)	0.8362 (3)	0.4822 (2)	0.0178 (7)
N3	0.2938 (4)	0.6344 (3)	0.6454 (2)	0.0201 (7)
O1	0.3462 (3)	1.0952 (2)	0.43185 (17)	0.0210 (6)
O2	0.0397 (3)	1.0102 (2)	0.35772 (18)	0.0226 (6)
C8	0.1579 (5)	0.7009 (4)	0.4825 (3)	0.0200 (8)
C4	0.4168 (5)	0.9174 (3)	0.2949 (2)	0.0176 (7)
N2	0.1844 (5)	0.6006 (3)	0.5649 (2)	0.0222 (7)
C5	0.6262 (5)	0.8655 (3)	0.3129 (3)	0.0202 (8)
H5	0.6753	0.8580	0.3766	0.024*
C3	0.3423 (5)	0.9291 (4)	0.2002 (3)	0.0206 (8)
H3	0.2019	0.9641	0.1888	0.025*
C1	0.6918 (5)	0.8360 (4)	0.1380 (3)	0.0230 (8)
C6	0.7617 (5)	0.8247 (4)	0.2337 (3)	0.0239 (8)
H6	0.9018	0.7892	0.2453	0.029*
C2	0.4798 (5)	0.8878 (4)	0.1225 (3)	0.0234 (8)
H2A	0.4299	0.8948	0.0590	0.028*
C14	0.4970 (5)	0.5378 (4)	0.6527 (3)	0.0240 (8)
H14A	0.6026	0.5861	0.6063	0.029*
H14B	0.4751	0.4415	0.6310	0.029*
C9	0.1481 (5)	0.6295 (4)	0.7354 (3)	0.0217 (8)
H9A	0.1506	0.5261	0.7692	0.026*
H9B	0.0040	0.6593	0.7157	0.026*
C10	0.2070 (5)	0.7335 (4)	0.8079 (3)	0.0259 (8)
H10A	0.2370	0.8305	0.7698	0.031*
H10B	0.0832	0.7514	0.8523	0.031*
C7	0.8410 (6)	0.7885 (4)	0.0541 (3)	0.0321 (9)
H7A	0.8045	0.8490	−0.0074	0.048*
H7B	0.8283	0.6834	0.0492	0.048*
H7C	0.9850	0.8028	0.0673	0.048*
C11	0.3933 (6)	0.6791 (4)	0.8708 (3)	0.0285 (9)
H11A	0.3572	0.5891	0.9156	0.034*
H11B	0.4170	0.7567	0.9112	0.034*
C13	0.5881 (5)	0.5058 (4)	0.7545 (3)	0.0242 (8)
H13A	0.7308	0.4576	0.7468	0.029*
H13B	0.5029	0.4330	0.7958	0.029*
C12	0.6003 (5)	0.6417 (4)	0.8107 (3)	0.0268 (9)
H12A	0.7156	0.6201	0.8556	0.032*
H12B	0.6330	0.7297	0.7633	0.032*
H1	0.317 (6)	0.839 (4)	0.530 (3)	0.028 (11)*
H2	0.131 (6)	0.516 (5)	0.566 (3)	0.032 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0216 (5)	0.0104 (4)	0.0270 (5)	−0.0015 (3)	−0.0028 (4)	−0.0049 (3)
O3	0.0248 (13)	0.0146 (12)	0.0283 (14)	−0.0036 (10)	−0.0058 (11)	−0.0053 (10)
N1	0.0217 (15)	0.0096 (14)	0.0238 (17)	−0.0032 (12)	−0.0057 (13)	−0.0040 (12)
N3	0.0193 (14)	0.0154 (15)	0.0274 (17)	−0.0014 (12)	−0.0034 (12)	−0.0088 (12)
O1	0.0256 (12)	0.0078 (11)	0.0306 (14)	−0.0026 (10)	−0.0039 (10)	−0.0040 (9)
O2	0.0216 (12)	0.0138 (12)	0.0326 (15)	0.0011 (10)	−0.0032 (10)	−0.0047 (10)
C8	0.0175 (17)	0.0131 (17)	0.030 (2)	0.0020 (14)	−0.0033 (15)	−0.0053 (15)
C4	0.0204 (17)	0.0061 (15)	0.0260 (19)	−0.0026 (14)	−0.0013 (14)	−0.0001 (13)
N2	0.0299 (17)	0.0120 (15)	0.0269 (17)	−0.0069 (13)	−0.0076 (13)	−0.0046 (12)
C5	0.0242 (18)	0.0101 (16)	0.027 (2)	−0.0054 (14)	−0.0041 (15)	−0.0017 (13)
C3	0.0231 (18)	0.0098 (16)	0.028 (2)	−0.0016 (14)	−0.0027 (15)	0.0000 (14)
C1	0.0239 (18)	0.0109 (16)	0.035 (2)	−0.0045 (15)	0.0008 (16)	−0.0055 (14)
C6	0.0206 (18)	0.0144 (18)	0.038 (2)	−0.0031 (15)	−0.0025 (16)	−0.0058 (15)
C2	0.033 (2)	0.0171 (18)	0.0216 (19)	−0.0049 (16)	−0.0030 (16)	−0.0042 (14)
C14	0.0249 (18)	0.0168 (18)	0.033 (2)	−0.0028 (15)	0.0000 (16)	−0.0120 (15)
C9	0.0205 (17)	0.0148 (17)	0.030 (2)	−0.0014 (14)	−0.0022 (15)	−0.0034 (14)
C10	0.0272 (19)	0.0203 (19)	0.032 (2)	−0.0018 (16)	0.0018 (16)	−0.0107 (15)
C7	0.036 (2)	0.031 (2)	0.031 (2)	−0.0045 (18)	0.0048 (17)	−0.0098 (17)
C11	0.030 (2)	0.024 (2)	0.034 (2)	−0.0023 (16)	−0.0042 (17)	−0.0125 (16)
C13	0.0208 (18)	0.0156 (18)	0.036 (2)	−0.0002 (15)	−0.0039 (16)	−0.0037 (15)
C12	0.0217 (18)	0.0245 (19)	0.037 (2)	0.0007 (16)	−0.0073 (16)	−0.0115 (16)

Geometric parameters (Å, º)

S1—N1	1.630 (3)	C2—H2A	0.9300
S1—O1	1.437 (2)	C14—H14A	0.9700
S1—O2	1.420 (2)	C14—H14B	0.9700
S1—C4	1.761 (3)	C14—C13	1.514 (5)
O3—C8	1.235 (4)	C9—H9A	0.9700
N1—C8	1.398 (4)	C9—H9B	0.9700
N1—H1	0.78 (4)	C9—C10	1.528 (5)
N3—N2	1.411 (4)	C10—H10A	0.9700
N3—C14	1.485 (4)	C10—H10B	0.9700
N3—C9	1.477 (4)	C10—C11	1.507 (5)
C8—N2	1.341 (4)	C7—H7A	0.9600
C4—C5	1.388 (5)	C7—H7B	0.9600
C4—C3	1.387 (5)	C7—H7C	0.9600
N2—H2	0.85 (4)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C5—C6	1.398 (5)	C11—C12	1.530 (5)
C3—H3	0.9300	C13—H13A	0.9700
C3—C2	1.390 (5)	C13—H13B	0.9700
C1—C6	1.388 (5)	C13—C12	1.532 (5)
C1—C2	1.398 (5)	C12—H12A	0.9700
C1—C7	1.512 (5)	C12—H12B	0.9700
C6—H6	0.9300
N1—S1—C4	105.42 (15)	H14A—C14—H14B	107.3
O1—S1—N1	104.20 (14)	C13—C14—H14A	108.2
O1—S1—C4	108.49 (14)	C13—C14—H14B	108.2
O2—S1—N1	110.89 (14)	N3—C9—H9A	109.0
O2—S1—O1	118.99 (14)	N3—C9—H9B	109.0
O2—S1—C4	108.02 (15)	N3—C9—C10	112.7 (2)
S1—N1—H1	121 (3)	H9A—C9—H9B	107.8
C8—N1—S1	125.3 (2)	C10—C9—H9A	109.0
C8—N1—H1	114 (3)	C10—C9—H9B	109.0
N2—N3—C14	109.1 (3)	C9—C10—H10A	108.0
N2—N3—C9	109.5 (2)	C9—C10—H10B	108.0
C9—N3—C14	117.3 (3)	H10A—C10—H10B	107.3
O3—C8—N1	122.3 (3)	C11—C10—C9	117.1 (3)
O3—C8—N2	123.3 (3)	C11—C10—H10A	108.0
N2—C8—N1	114.5 (3)	C11—C10—H10B	108.0
C5—C4—S1	119.4 (3)	C1—C7—H7A	109.5
C3—C4—S1	119.6 (3)	C1—C7—H7B	109.5
C3—C4—C5	121.0 (3)	C1—C7—H7C	109.5
N3—N2—H2	122 (3)	H7A—C7—H7B	109.5
C8—N2—N3	121.7 (3)	H7A—C7—H7C	109.5
C8—N2—H2	116 (3)	H7B—C7—H7C	109.5
C4—C5—H5	120.6	C10—C11—H11A	108.7
C4—C5—C6	118.8 (3)	C10—C11—H11B	108.7
C6—C5—H5	120.6	C10—C11—C12	114.1 (3)
C4—C3—H3	120.4	H11A—C11—H11B	107.6
C4—C3—C2	119.2 (3)	C12—C11—H11A	108.7
C2—C3—H3	120.4	C12—C11—H11B	108.7
C6—C1—C2	118.3 (3)	C14—C13—H13A	108.0
C6—C1—C7	120.3 (3)	C14—C13—H13B	108.0
C2—C1—C7	121.4 (3)	C14—C13—C12	117.0 (3)
C5—C6—H6	119.3	H13A—C13—H13B	107.3
C1—C6—C5	121.5 (3)	C12—C13—H13A	108.0
C1—C6—H6	119.3	C12—C13—H13B	108.0
C3—C2—C1	121.2 (3)	C11—C12—C13	112.8 (3)
C3—C2—H2A	119.4	C11—C12—H12A	109.0
C1—C2—H2A	119.4	C11—C12—H12B	109.0
N3—C14—H14A	108.2	C13—C12—H12A	109.0
N3—C14—H14B	108.2	C13—C12—H12B	109.0
N3—C14—C13	116.4 (3)	H12A—C12—H12B	107.8
S1—N1—C8—O3	1.1 (5)	C4—C5—C6—C1	0.4 (5)
S1—N1—C8—N2	−179.7 (3)	C4—C3—C2—C1	−0.5 (5)
S1—C4—C5—C6	−176.8 (2)	N2—N3—C14—C13	−154.4 (3)
S1—C4—C3—C2	176.8 (2)	N2—N3—C9—C10	−152.0 (3)
O3—C8—N2—N3	−178.2 (3)	C5—C4—C3—C2	0.1 (4)
N1—S1—C4—C5	−55.4 (3)	C3—C4—C5—C6	−0.1 (4)
N1—S1—C4—C3	127.9 (2)	C6—C1—C2—C3	0.9 (5)
N1—C8—N2—N3	2.5 (5)	C2—C1—C6—C5	−0.8 (5)
N3—C14—C13—C12	−48.0 (4)	C14—N3—N2—C8	−111.9 (4)
N3—C9—C10—C11	−76.8 (4)	C14—N3—C9—C10	82.9 (3)
O1—S1—N1—C8	173.3 (3)	C14—C13—C12—C11	85.8 (4)
O1—S1—C4—C5	55.8 (3)	C9—N3—N2—C8	118.5 (3)
O1—S1—C4—C3	−121.0 (2)	C9—N3—C14—C13	−29.1 (4)
O2—S1—N1—C8	44.2 (3)	C9—C10—C11—C12	56.2 (4)
O2—S1—C4—C5	−174.0 (2)	C10—C11—C12—C13	−65.9 (4)
O2—S1—C4—C3	9.3 (3)	C7—C1—C6—C5	−178.9 (3)
C4—S1—N1—C8	−72.5 (3)	C7—C1—C2—C3	178.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.78 (4)	2.37 (4)	2.991 (3)	137 (4)
N2—H2···O3^ii	0.85 (4)	2.15 (4)	2.985 (3)	168 (4)

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