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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619005217/ku3243sup1.cif
Contains datablocks TZA_I_295, 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, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_295sup2.hkl
Contains datablock TZA_I_295

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_275sup3.hkl
Contains datablock TZA_I_275

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_250sup4.hkl
Contains datablock TZA_I_250

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_225sup5.hkl
Contains datablock TZA_I_225

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_200sup6.hkl
Contains datablock TZA_I_200

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_175sup7.hkl
Contains datablock TZA_I_175

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_150sup8.hkl
Contains datablock TZA_I_150

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_125sup9.hkl
Contains datablock TZA_I_125

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_100sup10.hkl
Contains datablock TZA_I_100

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_295sup11.hkl
Contains datablock TZA_II_295

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_250sup12.hkl
Contains datablock TZA_II_250

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_200sup13.hkl
Contains datablock TZA_II_200

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_150sup14.hkl
Contains datablock TZA_II_150

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_100sup15.hkl
Contains datablock TZA_II_100

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_295sup16.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619005217/ku3243sup17.pdf
Supplementary material

CCDC references: 1910360; 1910359; 1910358; 1910357; 1910356; 1910355; 1910354; 1910353; 1910352; 1910351; 1910350; 1910349; 1910348; 1910347

Computing details top

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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.336 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.3506 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.2241 (9) ÅCell parameters from 3538 reflections
c = 13.4984 (13) Åθ = 2.3–24.0°
α = 79.091 (8)°µ = 0.22 mm1
β = 87.215 (8)°T = 295 K
γ = 85.815 (8)°Block, colourless
V = 773.87 (13) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3157 independent reflections
Radiation source: Enhance (Mo) X-ray Source2134 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 1.5°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.912, Tmax = 1.000l = 1616
12448 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0469P)2 + 0.175P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3157 reflectionsΔρmax = 0.32 e Å3
218 parametersΔρmin = 0.26 e Å3
2 restraints
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.02120 (10)0.27197 (6)0.22617 (5)0.0525 (2)
O10.1381 (3)0.15808 (18)0.18513 (13)0.0697 (5)
O20.2030 (3)0.27333 (19)0.23401 (14)0.0681 (5)
O30.0662 (3)0.45843 (17)0.38256 (12)0.0541 (4)
N10.1136 (4)0.2549 (2)0.33948 (15)0.0535 (5)
H10.210 (4)0.196 (3)0.3526 (19)0.052 (8)*
N20.1636 (4)0.3207 (2)0.49094 (16)0.0556 (6)
H20.137 (4)0.378 (3)0.5288 (19)0.055 (8)*
N30.3141 (3)0.2000 (2)0.51011 (14)0.0520 (5)
C10.2067 (4)0.7173 (3)0.05245 (18)0.0547 (6)
C20.3548 (4)0.6027 (3)0.0791 (2)0.0672 (7)
H2A0.49560.61700.06020.081*
C30.3020 (4)0.4662 (3)0.1333 (2)0.0633 (7)
H30.40570.39020.15060.076*
C40.0939 (4)0.4452 (2)0.16108 (16)0.0443 (5)
C50.0569 (4)0.5579 (3)0.1357 (2)0.0607 (7)
H50.19760.54410.15510.073*
C60.0003 (4)0.6929 (3)0.0807 (2)0.0640 (7)
H60.10360.76840.06270.077*
C70.2679 (5)0.8658 (3)0.0051 (2)0.0802 (9)
H7A0.40930.85640.03260.120*
H7B0.26060.93550.03970.120*
H7C0.17250.89990.05890.120*
C80.0612 (4)0.3526 (2)0.40410 (17)0.0457 (6)
C90.5260 (4)0.2532 (3)0.5135 (2)0.0666 (7)
H9AA0.62750.17120.50760.080*0.826 (6)
H9AB0.54590.32840.45360.080*0.826 (6)
H9BC0.59660.25220.44820.080*0.174 (6)
H9BD0.50870.35550.52190.080*0.174 (6)
C10A0.5835 (5)0.3148 (3)0.6004 (2)0.0624 (11)0.826 (6)
H10A0.47170.38650.61410.075*0.826 (6)
H10B0.71080.36730.58220.075*0.826 (6)
C10B0.6665 (17)0.1744 (15)0.5905 (5)0.061 (5)0.174 (6)
H10C0.80960.20050.57040.074*0.174 (6)
H10D0.66160.06910.59180.074*0.174 (6)
C110.6209 (5)0.2021 (4)0.6964 (2)0.0847 (9)
H11A0.72050.12480.67960.102*0.826 (6)
H11B0.68970.25060.74260.102*0.826 (6)
H11C0.74580.16960.73530.102*0.174 (6)
H11D0.59750.30800.69310.102*0.174 (6)
C120.4373 (4)0.1291 (4)0.7522 (2)0.0750 (8)
H12A0.41000.17020.81300.090*
H12B0.47930.02500.77340.090*
C130.2322 (4)0.1397 (3)0.69923 (19)0.0604 (7)
H13A0.13320.07950.74280.072*
H13B0.17430.24140.68960.068 (8)*
C140.2479 (5)0.0918 (3)0.5987 (2)0.0635 (7)
H14A0.352 (4)0.006 (3)0.608 (2)0.080 (9)*
H14B0.109 (4)0.062 (3)0.5863 (19)0.065 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0685 (4)0.0432 (3)0.0473 (4)0.0016 (3)0.0136 (3)0.0098 (3)
O10.1059 (15)0.0490 (10)0.0580 (11)0.0109 (10)0.0181 (10)0.0219 (9)
O20.0626 (11)0.0631 (11)0.0773 (13)0.0158 (9)0.0156 (9)0.0020 (10)
O30.0624 (11)0.0487 (9)0.0485 (10)0.0116 (8)0.0043 (8)0.0071 (8)
N10.0707 (15)0.0443 (12)0.0448 (12)0.0121 (11)0.0122 (10)0.0098 (10)
N20.0750 (15)0.0491 (12)0.0427 (12)0.0135 (11)0.0097 (11)0.0129 (10)
N30.0628 (13)0.0450 (11)0.0466 (12)0.0074 (10)0.0106 (10)0.0069 (9)
C10.0659 (17)0.0583 (15)0.0410 (13)0.0107 (13)0.0091 (12)0.0076 (12)
C20.0502 (15)0.0775 (19)0.0725 (19)0.0101 (14)0.0013 (13)0.0092 (16)
C30.0507 (16)0.0614 (16)0.0745 (18)0.0110 (13)0.0073 (13)0.0082 (14)
C40.0517 (14)0.0434 (12)0.0386 (12)0.0018 (11)0.0088 (10)0.0097 (10)
C50.0482 (14)0.0607 (16)0.0663 (17)0.0026 (13)0.0041 (12)0.0035 (13)
C60.0650 (18)0.0538 (15)0.0653 (17)0.0077 (13)0.0055 (14)0.0055 (13)
C70.103 (2)0.0696 (19)0.0662 (19)0.0273 (18)0.0117 (17)0.0016 (15)
C80.0556 (14)0.0407 (12)0.0391 (13)0.0061 (11)0.0017 (11)0.0030 (10)
C90.0669 (18)0.0758 (18)0.0544 (16)0.0037 (15)0.0021 (13)0.0067 (14)
C10A0.056 (2)0.060 (2)0.072 (2)0.0103 (16)0.0008 (16)0.0126 (17)
C10B0.047 (9)0.081 (12)0.048 (9)0.015 (8)0.007 (7)0.000 (8)
C110.0695 (19)0.119 (3)0.068 (2)0.0093 (19)0.0161 (16)0.0166 (19)
C120.0702 (19)0.096 (2)0.0536 (17)0.0036 (16)0.0092 (14)0.0022 (16)
C130.0629 (16)0.0559 (16)0.0569 (16)0.0083 (13)0.0042 (13)0.0034 (13)
C140.078 (2)0.0474 (15)0.0642 (18)0.0132 (15)0.0135 (15)0.0028 (13)
Geometric parameters (Å, º) top
S1—O11.4241 (18)C9—H9AA0.9700
S1—O21.4221 (18)C9—H9AB0.9700
S1—N11.640 (2)C9—H9BC0.9700
S1—C41.754 (2)C9—H9BD0.9700
O3—C81.222 (3)C9—C10A1.468 (4)
N1—H10.79 (2)C9—C10B1.454 (6)
N1—C81.382 (3)C10A—H10A0.9700
N2—H20.81 (2)C10A—H10B0.9700
N2—N31.407 (3)C10A—C111.517 (4)
N2—C81.341 (3)C10B—H10C0.9700
N3—C91.471 (3)C10B—H10D0.9700
N3—C141.471 (3)C10B—C111.511 (6)
C1—C21.369 (4)C11—H11A0.9700
C1—C61.370 (3)C11—H11B0.9700
C1—C71.508 (4)C11—H11C0.9700
C2—H2A0.9300C11—H11D0.9700
C2—C31.387 (4)C11—C121.489 (4)
C3—H30.9300C12—H12A0.9700
C3—C41.373 (3)C12—H12B0.9700
C4—C51.367 (3)C12—C131.505 (4)
C5—H50.9300C13—H13A0.9700
C5—C61.386 (3)C13—H13B0.9700
C6—H60.9300C13—C141.501 (4)
C7—H7A0.9600C14—H14A0.99 (3)
C7—H7B0.9600C14—H14B0.98 (3)
C7—H7C0.9600
O1—S1—N1103.56 (11)C10A—C9—N3120.1 (2)
O1—S1—C4109.54 (11)C10A—C9—H9AA107.3
O2—S1—O1119.57 (12)C10A—C9—H9AB107.3
O2—S1—N1109.05 (12)C10B—C9—N3118.3 (6)
O2—S1—C4108.78 (11)C10B—C9—H9BC107.7
N1—S1—C4105.38 (11)C10B—C9—H9BD107.7
S1—N1—H1116.1 (19)C9—C10A—H10A108.5
C8—N1—S1124.20 (19)C9—C10A—H10B108.5
C8—N1—H1118.6 (19)C9—C10A—C11115.1 (3)
N3—N2—H2123.5 (19)H10A—C10A—H10B107.5
C8—N2—H2115.1 (19)C11—C10A—H10A108.5
C8—N2—N3121.3 (2)C11—C10A—H10B108.5
N2—N3—C9110.09 (19)C9—C10B—H10C108.2
N2—N3—C14110.7 (2)C9—C10B—H10D108.2
C14—N3—C9115.6 (2)C9—C10B—C11116.3 (5)
C2—C1—C6117.6 (2)H10C—C10B—H10D107.4
C2—C1—C7121.5 (2)C11—C10B—H10C108.2
C6—C1—C7120.9 (3)C11—C10B—H10D108.2
C1—C2—H2A118.9C10A—C11—H11A107.6
C1—C2—C3122.3 (2)C10A—C11—H11B107.6
C3—C2—H2A118.9C10B—C11—H11C108.2
C2—C3—H3120.6C10B—C11—H11D108.2
C4—C3—C2118.8 (2)H11A—C11—H11B107.0
C4—C3—H3120.6H11C—C11—H11D107.4
C3—C4—S1119.85 (19)C12—C11—C10A119.1 (3)
C5—C4—S1120.04 (18)C12—C11—C10B116.3 (6)
C5—C4—C3120.1 (2)C12—C11—H11A107.6
C4—C5—H5120.1C12—C11—H11B107.6
C4—C5—C6119.8 (2)C12—C11—H11C108.2
C6—C5—H5120.1C12—C11—H11D108.2
C1—C6—C5121.4 (2)C11—C12—H12A107.7
C1—C6—H6119.3C11—C12—H12B107.7
C5—C6—H6119.3C11—C12—C13118.5 (2)
C1—C7—H7A109.5H12A—C12—H12B107.1
C1—C7—H7B109.5C13—C12—H12A107.7
C1—C7—H7C109.5C13—C12—H12B107.7
H7A—C7—H7B109.5C12—C13—H13A108.5
H7A—C7—H7C109.5C12—C13—H13B108.5
H7B—C7—H7C109.5H13A—C13—H13B107.5
O3—C8—N1122.2 (2)C14—C13—C12115.1 (2)
O3—C8—N2123.9 (2)C14—C13—H13A108.5
N2—C8—N1113.9 (2)C14—C13—H13B108.5
N3—C9—H9AA107.3N3—C14—C13117.8 (2)
N3—C9—H9AB107.3N3—C14—H14A108.8 (16)
N3—C9—H9BC107.7N3—C14—H14B107.8 (15)
N3—C9—H9BD107.7C13—C14—H14A104.7 (17)
H9AA—C9—H9AB106.9C13—C14—H14B107.1 (15)
H9BC—C9—H9BD107.1H14A—C14—H14B111 (2)
S1—N1—C8—O32.6 (3)C2—C3—C4—S1178.0 (2)
S1—N1—C8—N2176.90 (17)C2—C3—C4—C50.3 (4)
S1—C4—C5—C6177.4 (2)C3—C4—C5—C60.8 (4)
O1—S1—N1—C8173.1 (2)C4—S1—N1—C858.1 (2)
O1—S1—C4—C340.0 (2)C4—C5—C6—C11.1 (4)
O1—S1—C4—C5138.3 (2)C6—C1—C2—C30.4 (4)
O2—S1—N1—C858.5 (2)C7—C1—C2—C3179.0 (2)
O2—S1—C4—C3172.3 (2)C7—C1—C6—C5178.5 (2)
O2—S1—C4—C55.9 (2)C8—N2—N3—C9112.7 (2)
N1—S1—C4—C370.9 (2)C8—N2—N3—C14118.3 (2)
N1—S1—C4—C5110.9 (2)C9—N3—C14—C1361.3 (3)
N2—N3—C9—C10A73.1 (3)C9—C10A—C11—C1271.0 (4)
N2—N3—C9—C10B139.2 (4)C9—C10B—C11—C1275.4 (11)
N2—N3—C14—C1364.7 (3)C10A—C11—C12—C1315.2 (4)
N3—N2—C8—O3177.8 (2)C10B—C11—C12—C1347.2 (5)
N3—N2—C8—N11.7 (3)C11—C12—C13—C1453.0 (4)
N3—C9—C10A—C1173.3 (4)C12—C13—C14—N382.9 (3)
N3—C9—C10B—C1176.0 (11)C14—N3—C9—C10A53.2 (3)
C1—C2—C3—C40.1 (4)C14—N3—C9—C10B12.8 (5)
C2—C1—C6—C51.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.81 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.343 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.3453 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1929 (5) ÅCell parameters from 3671 reflections
c = 13.4917 (7) Åθ = 2.3–24.1°
α = 79.103 (5)°µ = 0.22 mm1
β = 87.266 (4)°T = 275 K
γ = 85.857 (5)°Block, colourless
V = 770.32 (7) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3149 independent reflections
Radiation source: Enhance (Mo) X-ray Source2245 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 2.3°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.915, Tmax = 1.000l = 1616
12387 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0426P)2 + 0.2182P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3149 reflectionsΔρmax = 0.27 e Å3
218 parametersΔρmin = 0.21 e Å3
2 restraints
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.02093 (10)0.27106 (6)0.22573 (4)0.0475 (2)
O10.1389 (3)0.15700 (18)0.18456 (12)0.0631 (5)
O20.2033 (3)0.27213 (19)0.23364 (13)0.0613 (5)
O30.0672 (2)0.45771 (17)0.38254 (11)0.0497 (4)
N10.1136 (4)0.2539 (2)0.33936 (14)0.0483 (5)
H10.209 (4)0.197 (3)0.3532 (18)0.045 (7)*
N20.1624 (3)0.3204 (2)0.49105 (15)0.0505 (5)
H20.135 (4)0.377 (3)0.5321 (19)0.059 (8)*
N30.3147 (3)0.2001 (2)0.51007 (13)0.0470 (5)
C10.2058 (4)0.7178 (3)0.05262 (16)0.0495 (6)
C20.3544 (4)0.6027 (3)0.0789 (2)0.0605 (7)
H2A0.49530.61710.05980.073*
C30.3020 (4)0.4660 (3)0.13291 (19)0.0571 (6)
H30.40580.38980.15010.068*
C40.0938 (3)0.4449 (2)0.16077 (15)0.0401 (5)
C50.0580 (4)0.5579 (3)0.13584 (18)0.0539 (6)
H50.19870.54370.15560.065*
C60.0013 (4)0.6932 (3)0.08114 (18)0.0570 (6)
H60.10540.76900.06330.068*
C70.2670 (5)0.8665 (3)0.0046 (2)0.0715 (8)
H7A0.40690.85660.03400.107*
H7B0.26430.93560.04070.107*
H7C0.16890.90230.05710.107*
C80.0616 (3)0.3523 (2)0.40436 (16)0.0413 (5)
C90.5267 (4)0.2536 (3)0.51312 (19)0.0614 (7)
H9AA0.54610.32900.45320.074*0.823 (6)
H9AB0.62830.17150.50710.074*0.823 (6)
H9BC0.59690.25280.44780.074*0.177 (6)
H9BD0.50950.35630.52170.074*0.177 (6)
C10A0.5847 (5)0.3160 (3)0.6003 (2)0.0560 (10)0.823 (6)
H10A0.47270.38770.61430.067*0.823 (6)
H10B0.71180.36900.58200.067*0.823 (6)
C10B0.6676 (16)0.1740 (14)0.5903 (4)0.063 (5)0.177 (6)
H10C0.81100.19970.57000.076*0.177 (6)
H10D0.66180.06850.59160.076*0.177 (6)
C110.6231 (4)0.2020 (4)0.6965 (2)0.0750 (8)
H11A0.72130.12400.67920.090*0.823 (6)
H11B0.69370.25000.74260.090*0.823 (6)
H11C0.74820.16870.73530.090*0.177 (6)
H11D0.60100.30830.69320.090*0.177 (6)
C120.4384 (4)0.1297 (3)0.75282 (19)0.0671 (7)
H12A0.41130.17170.81330.081*
H12B0.47970.02520.77460.081*
C130.2326 (4)0.1402 (3)0.69950 (18)0.0537 (6)
H13A0.13320.08010.74310.064*
H13B0.17500.24230.68940.068 (8)*
C140.2492 (5)0.0911 (3)0.5988 (2)0.0578 (7)
H14A0.352 (4)0.006 (3)0.6056 (19)0.068 (8)*
H14B0.115 (4)0.063 (3)0.5847 (18)0.064 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0617 (4)0.0393 (3)0.0426 (3)0.0013 (3)0.0118 (3)0.0088 (3)
O10.0952 (13)0.0441 (10)0.0531 (10)0.0097 (9)0.0157 (9)0.0193 (8)
O20.0571 (10)0.0563 (11)0.0694 (11)0.0149 (8)0.0139 (8)0.0018 (9)
O30.0576 (10)0.0461 (10)0.0430 (9)0.0092 (8)0.0036 (7)0.0068 (7)
N10.0652 (13)0.0387 (11)0.0404 (11)0.0097 (10)0.0130 (10)0.0080 (9)
N20.0681 (13)0.0444 (12)0.0390 (11)0.0121 (10)0.0083 (9)0.0126 (9)
N30.0563 (12)0.0408 (11)0.0423 (11)0.0068 (9)0.0081 (9)0.0062 (8)
C10.0609 (15)0.0531 (15)0.0362 (12)0.0105 (12)0.0075 (11)0.0084 (11)
C20.0443 (14)0.0713 (19)0.0650 (16)0.0115 (13)0.0024 (12)0.0088 (14)
C30.0468 (14)0.0542 (16)0.0680 (17)0.0077 (12)0.0052 (12)0.0090 (13)
C40.0453 (12)0.0415 (12)0.0339 (11)0.0016 (10)0.0066 (9)0.0088 (9)
C50.0433 (13)0.0533 (15)0.0590 (15)0.0033 (11)0.0030 (11)0.0033 (12)
C60.0570 (15)0.0462 (15)0.0607 (16)0.0094 (12)0.0055 (12)0.0040 (12)
C70.091 (2)0.0610 (18)0.0608 (17)0.0212 (15)0.0116 (15)0.0025 (14)
C80.0497 (13)0.0362 (12)0.0364 (12)0.0043 (10)0.0010 (10)0.0026 (10)
C90.0626 (16)0.0694 (18)0.0494 (15)0.0041 (13)0.0006 (12)0.0051 (13)
C10A0.0498 (17)0.054 (2)0.066 (2)0.0104 (15)0.0038 (14)0.0148 (16)
C10B0.046 (8)0.088 (13)0.051 (9)0.009 (8)0.007 (7)0.001 (8)
C110.0616 (17)0.107 (2)0.0581 (17)0.0091 (16)0.0131 (14)0.0149 (17)
C120.0651 (17)0.084 (2)0.0473 (15)0.0035 (15)0.0063 (13)0.0026 (14)
C130.0550 (14)0.0489 (15)0.0523 (15)0.0070 (11)0.0024 (11)0.0033 (11)
C140.0723 (19)0.0414 (15)0.0593 (16)0.0095 (14)0.0142 (14)0.0026 (12)
Geometric parameters (Å, º) top
S1—O11.4268 (17)C9—H9AA0.9700
S1—O21.4215 (17)C9—H9AB0.9700
S1—N11.644 (2)C9—H9BC0.9700
S1—C41.753 (2)C9—H9BD0.9700
O3—C81.222 (3)C9—C10A1.475 (4)
N1—H10.78 (2)C9—C10B1.458 (6)
N1—C81.388 (3)C10A—H10A0.9700
N2—H20.84 (3)C10A—H10B0.9700
N2—N31.409 (3)C10A—C111.524 (4)
N2—C81.333 (3)C10B—H10C0.9700
N3—C91.470 (3)C10B—H10D0.9700
N3—C141.473 (3)C10B—C111.514 (6)
C1—C21.371 (4)C11—H11A0.9700
C1—C61.374 (3)C11—H11B0.9700
C1—C71.506 (3)C11—H11C0.9700
C2—H2A0.9300C11—H11D0.9700
C2—C31.382 (3)C11—C121.493 (4)
C3—H30.9300C12—H12A0.9700
C3—C41.373 (3)C12—H12B0.9700
C4—C51.369 (3)C12—C131.509 (3)
C5—H50.9300C13—H13A0.9700
C5—C61.384 (3)C13—H13B0.9700
C6—H60.9300C13—C141.507 (4)
C7—H7A0.9600C14—H14A0.98 (3)
C7—H7B0.9600C14—H14B0.94 (3)
C7—H7C0.9600
O1—S1—N1103.49 (11)H9BC—C9—H9BD107.2
O1—S1—C4109.34 (10)C10A—C9—H9AA107.3
O2—S1—O1119.79 (11)C10A—C9—H9AB107.3
O2—S1—N1108.96 (11)C10B—C9—N3118.0 (6)
O2—S1—C4108.91 (10)C10B—C9—H9BC107.8
N1—S1—C4105.35 (10)C10B—C9—H9BD107.8
S1—N1—H1117.5 (18)C9—C10A—H10A108.6
C8—N1—S1124.33 (18)C9—C10A—H10B108.6
C8—N1—H1116.9 (18)C9—C10A—C11114.8 (2)
N3—N2—H2121.8 (18)H10A—C10A—H10B107.6
C8—N2—H2116.9 (18)C11—C10A—H10A108.6
C8—N2—N3121.21 (19)C11—C10A—H10B108.6
N2—N3—C9110.50 (18)C9—C10B—H10C108.2
N2—N3—C14110.53 (19)C9—C10B—H10D108.2
C9—N3—C14115.6 (2)C9—C10B—C11116.4 (5)
C2—C1—C6117.7 (2)H10C—C10B—H10D107.3
C2—C1—C7121.3 (2)C11—C10B—H10C108.2
C6—C1—C7121.0 (2)C11—C10B—H10D108.2
C1—C2—H2A118.9C10A—C11—H11A107.6
C1—C2—C3122.2 (2)C10A—C11—H11B107.6
C3—C2—H2A118.9C10B—C11—H11C108.2
C2—C3—H3120.6C10B—C11—H11D108.2
C4—C3—C2118.8 (2)H11A—C11—H11B107.0
C4—C3—H3120.6H11C—C11—H11D107.3
C3—C4—S1119.91 (18)C12—C11—C10A118.8 (2)
C5—C4—S1119.75 (16)C12—C11—C10B116.5 (6)
C5—C4—C3120.3 (2)C12—C11—H11A107.6
C4—C5—H5120.2C12—C11—H11B107.6
C4—C5—C6119.7 (2)C12—C11—H11C108.2
C6—C5—H5120.2C12—C11—H11D108.2
C1—C6—C5121.3 (2)C11—C12—H12A107.7
C1—C6—H6119.4C11—C12—H12B107.7
C5—C6—H6119.4C11—C12—C13118.4 (2)
C1—C7—H7A109.5H12A—C12—H12B107.1
C1—C7—H7B109.5C13—C12—H12A107.7
C1—C7—H7C109.5C13—C12—H12B107.7
H7A—C7—H7B109.5C12—C13—H13A108.5
H7A—C7—H7C109.5C12—C13—H13B108.5
H7B—C7—H7C109.5H13A—C13—H13B107.5
O3—C8—N1121.7 (2)C14—C13—C12114.9 (2)
O3—C8—N2124.1 (2)C14—C13—H13A108.5
N2—C8—N1114.2 (2)C14—C13—H13B108.5
N3—C9—H9AA107.3N3—C14—C13117.5 (2)
N3—C9—H9AB107.3N3—C14—H14A107.8 (15)
N3—C9—H9BC107.8N3—C14—H14B106.0 (16)
N3—C9—H9BD107.8C13—C14—H14A106.7 (15)
N3—C9—C10A120.0 (2)C13—C14—H14B108.3 (15)
H9AA—C9—H9AB106.9H14A—C14—H14B110 (2)
S1—N1—C8—O33.3 (3)C2—C3—C4—S1177.93 (18)
S1—N1—C8—N2177.16 (16)C2—C3—C4—C50.4 (3)
S1—C4—C5—C6177.48 (18)C3—C4—C5—C60.9 (3)
O1—S1—N1—C8172.74 (19)C4—S1—N1—C858.0 (2)
O1—S1—C4—C339.6 (2)C4—C5—C6—C11.2 (4)
O1—S1—C4—C5138.71 (19)C6—C1—C2—C30.5 (4)
O2—S1—N1—C858.8 (2)C7—C1—C2—C3178.9 (2)
O2—S1—C4—C3172.24 (18)C7—C1—C6—C5178.5 (2)
O2—S1—C4—C56.1 (2)C8—N2—N3—C9111.9 (2)
N1—S1—C4—C371.0 (2)C8—N2—N3—C14118.9 (2)
N1—S1—C4—C5110.6 (2)C9—N3—C14—C1361.9 (3)
N2—N3—C9—C10A73.1 (3)C9—C10A—C11—C1271.8 (3)
N2—N3—C9—C10B139.2 (4)C9—C10B—C11—C1275.2 (11)
N2—N3—C14—C1364.6 (3)C10A—C11—C12—C1316.1 (4)
N3—N2—C8—O3177.74 (19)C10B—C11—C12—C1346.6 (5)
N3—N2—C8—N12.7 (3)C11—C12—C13—C1452.8 (3)
N3—C9—C10A—C1173.4 (3)C12—C13—C14—N383.4 (3)
N3—C9—C10B—C1176.3 (11)C14—N3—C9—C10A53.4 (3)
C1—C2—C3—C40.2 (4)C14—N3—C9—C10B12.8 (4)
C2—C1—C6—C51.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.84 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.351 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.3346 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1641 (5) ÅCell parameters from 4017 reflections
c = 13.4642 (7) Åθ = 2.3–26.5°
α = 79.222 (4)°µ = 0.23 mm1
β = 87.305 (4)°T = 250 K
γ = 85.936 (4)°Block, colourless
V = 765.43 (7) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3131 independent reflections
Radiation source: Enhance (Mo) X-ray Source2355 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 2.3°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.919, Tmax = 1.000l = 1616
12313 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0434P)2 + 0.1936P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3131 reflectionsΔρmax = 0.30 e Å3
218 parametersΔρmin = 0.22 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.02087 (9)0.27000 (6)0.22520 (4)0.04136 (18)
O10.1394 (3)0.15591 (17)0.18364 (11)0.0553 (4)
O20.2039 (2)0.27037 (17)0.23306 (12)0.0539 (4)
O30.0680 (2)0.45699 (16)0.38256 (10)0.0432 (4)
N10.1140 (3)0.2527 (2)0.33923 (13)0.0429 (5)
H10.208 (4)0.196 (3)0.3532 (18)0.048 (7)*
N20.1619 (3)0.3197 (2)0.49126 (14)0.0450 (5)
H20.138 (3)0.380 (3)0.5300 (17)0.049 (7)*
N30.3157 (3)0.19975 (19)0.51009 (13)0.0426 (4)
C10.2052 (3)0.7188 (2)0.05231 (15)0.0424 (5)
C20.3545 (4)0.6032 (3)0.07873 (18)0.0516 (6)
H2A0.49560.61800.05990.062*
C30.3022 (3)0.4660 (3)0.13218 (17)0.0496 (6)
H30.40610.38940.14870.060*
C40.0934 (3)0.4446 (2)0.16062 (14)0.0353 (5)
C50.0600 (3)0.5578 (3)0.13592 (17)0.0470 (5)
H50.20070.54320.15570.056*
C60.0030 (4)0.6937 (3)0.08124 (17)0.0498 (6)
H60.10730.76970.06370.060*
C70.2667 (4)0.8675 (3)0.00456 (19)0.0625 (7)
H7A0.40630.85730.03450.094*
H7B0.26540.93640.04120.094*
H7C0.16780.90390.05670.094*
C80.0609 (3)0.3512 (2)0.40422 (14)0.0369 (5)
C90.5277 (4)0.2545 (3)0.51281 (17)0.0537 (6)
H9AA0.54600.33080.45310.064*0.834 (6)
H9AB0.63020.17280.50610.064*0.834 (6)
H9BC0.59760.25550.44700.064*0.166 (6)
H9BD0.51080.35670.52310.064*0.166 (6)
C10A0.5858 (4)0.3166 (3)0.6007 (2)0.0488 (9)0.834 (6)
H10A0.47270.38720.61560.059*0.834 (6)
H10B0.71220.37090.58250.059*0.834 (6)
C10B0.6675 (16)0.1709 (14)0.5897 (4)0.056 (5)0.166 (6)
H10C0.81230.19280.56900.067*0.166 (6)
H10D0.65530.06560.59130.067*0.166 (6)
C110.6267 (4)0.2009 (3)0.69647 (18)0.0629 (7)
H11A0.72230.12210.67800.075*0.834 (6)
H11B0.70080.24780.74230.075*0.834 (6)
H11C0.75240.16680.73480.075*0.166 (6)
H11D0.60690.30770.69280.075*0.166 (6)
C120.4405 (4)0.1301 (3)0.75386 (18)0.0573 (6)
H12A0.41380.17410.81370.069*
H12B0.48070.02550.77670.069*
C130.2340 (3)0.1404 (3)0.69991 (16)0.0460 (5)
H13A0.13390.08060.74350.055*
H13B0.17660.24290.68950.050 (6)*
C140.2517 (5)0.0903 (3)0.59926 (18)0.0511 (6)
H14A0.357 (4)0.003 (3)0.6037 (17)0.058 (7)*
H14B0.121 (4)0.061 (3)0.5850 (17)0.054 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0533 (3)0.0342 (3)0.0374 (3)0.0007 (2)0.0102 (2)0.0073 (2)
O10.0819 (11)0.0393 (9)0.0477 (9)0.0081 (8)0.0126 (8)0.0175 (7)
O20.0507 (9)0.0498 (10)0.0604 (10)0.0131 (7)0.0115 (7)0.0021 (8)
O30.0509 (9)0.0387 (9)0.0383 (8)0.0079 (7)0.0039 (6)0.0059 (7)
N10.0561 (12)0.0368 (11)0.0353 (10)0.0080 (9)0.0099 (9)0.0070 (8)
N20.0611 (12)0.0389 (11)0.0354 (10)0.0113 (9)0.0082 (9)0.0120 (9)
N30.0526 (11)0.0368 (10)0.0375 (10)0.0052 (8)0.0082 (8)0.0060 (8)
C10.0522 (13)0.0448 (13)0.0316 (11)0.0082 (11)0.0059 (9)0.0078 (9)
C20.0394 (12)0.0616 (16)0.0538 (14)0.0090 (11)0.0026 (10)0.0094 (12)
C30.0399 (12)0.0478 (14)0.0588 (14)0.0073 (10)0.0046 (10)0.0067 (11)
C40.0412 (11)0.0361 (11)0.0289 (10)0.0021 (9)0.0068 (8)0.0073 (8)
C50.0374 (11)0.0472 (14)0.0505 (13)0.0014 (10)0.0021 (10)0.0050 (11)
C60.0503 (13)0.0412 (13)0.0522 (14)0.0068 (10)0.0056 (11)0.0032 (11)
C70.0765 (17)0.0551 (16)0.0546 (15)0.0193 (13)0.0095 (13)0.0003 (12)
C80.0455 (12)0.0327 (11)0.0315 (11)0.0050 (9)0.0025 (9)0.0032 (9)
C90.0547 (14)0.0592 (15)0.0446 (13)0.0024 (12)0.0002 (11)0.0035 (11)
C10A0.0448 (15)0.0454 (18)0.0573 (18)0.0085 (13)0.0024 (13)0.0115 (13)
C10B0.036 (8)0.082 (12)0.042 (8)0.003 (7)0.001 (6)0.005 (7)
C110.0522 (14)0.087 (2)0.0510 (15)0.0072 (13)0.0098 (11)0.0147 (14)
C120.0561 (14)0.0677 (17)0.0439 (14)0.0052 (12)0.0061 (11)0.0020 (12)
C130.0481 (12)0.0421 (13)0.0436 (13)0.0053 (10)0.0024 (10)0.0029 (10)
C140.0640 (16)0.0383 (14)0.0508 (14)0.0103 (12)0.0135 (12)0.0018 (11)
Geometric parameters (Å, º) top
S1—O11.4275 (16)C9—H9AA0.9700
S1—O21.4229 (16)C9—H9AB0.9700
S1—N11.6465 (19)C9—H9BC0.9700
S1—C41.753 (2)C9—H9BD0.9700
O3—C81.223 (2)C9—C10A1.477 (3)
N1—H10.77 (2)C9—C10B1.462 (6)
N1—C81.385 (3)C10A—H10A0.9700
N2—H20.83 (2)C10A—H10B0.9700
N2—N31.411 (2)C10A—C111.528 (4)
N2—C81.336 (3)C10B—H10C0.9700
N3—C91.471 (3)C10B—H10D0.9700
N3—C141.475 (3)C10B—C111.520 (6)
C1—C21.375 (3)C11—H11A0.9700
C1—C61.380 (3)C11—H11B0.9700
C1—C71.501 (3)C11—H11C0.9700
C2—H2A0.9300C11—H11D0.9700
C2—C31.381 (3)C11—C121.498 (3)
C3—H30.9300C12—H12A0.9700
C3—C41.377 (3)C12—H12B0.9700
C4—C51.374 (3)C12—C131.515 (3)
C5—H50.9300C13—H13A0.9700
C5—C61.386 (3)C13—H13B0.9700
C6—H60.9300C13—C141.507 (3)
C7—H7A0.9600C14—H14A1.00 (3)
C7—H7B0.9600C14—H14B0.92 (2)
C7—H7C0.9600
O1—S1—N1103.47 (10)H9BC—C9—H9BD107.3
O1—S1—C4109.39 (10)C10A—C9—H9AA107.4
O2—S1—O1119.69 (10)C10A—C9—H9AB107.4
O2—S1—N1109.02 (10)C10B—C9—N3116.5 (6)
O2—S1—C4108.96 (10)C10B—C9—H9BC108.2
N1—S1—C4105.31 (9)C10B—C9—H9BD108.2
S1—N1—H1117.8 (18)C9—C10A—H10A108.6
C8—N1—S1124.03 (17)C9—C10A—H10B108.6
C8—N1—H1117.0 (18)C9—C10A—C11114.6 (2)
N3—N2—H2122.6 (16)H10A—C10A—H10B107.6
C8—N2—H2115.9 (16)C11—C10A—H10A108.6
C8—N2—N3121.16 (18)C11—C10A—H10B108.6
N2—N3—C9110.60 (17)C9—C10B—H10C108.3
N2—N3—C14110.56 (18)C9—C10B—H10D108.3
C9—N3—C14115.49 (18)C9—C10B—C11116.0 (4)
C2—C1—C6117.6 (2)H10C—C10B—H10D107.4
C2—C1—C7121.2 (2)C11—C10B—H10C108.3
C6—C1—C7121.2 (2)C11—C10B—H10D108.3
C1—C2—H2A118.8C10A—C11—H11A107.7
C1—C2—C3122.3 (2)C10A—C11—H11B107.7
C3—C2—H2A118.8C10B—C11—H11C108.3
C2—C3—H3120.6C10B—C11—H11D108.3
C4—C3—C2118.8 (2)H11A—C11—H11B107.1
C4—C3—H3120.6H11C—C11—H11D107.4
C3—C4—S1119.86 (16)C12—C11—C10A118.2 (2)
C5—C4—S1119.60 (15)C12—C11—C10B116.1 (6)
C5—C4—C3120.5 (2)C12—C11—H11A107.7
C4—C5—H5120.3C12—C11—H11B107.7
C4—C5—C6119.39 (19)C12—C11—H11C108.3
C6—C5—H5120.3C12—C11—H11D108.3
C1—C6—C5121.4 (2)C11—C12—H12A107.8
C1—C6—H6119.3C11—C12—H12B107.8
C5—C6—H6119.3C11—C12—C13118.1 (2)
C1—C7—H7A109.5H12A—C12—H12B107.1
C1—C7—H7B109.5C13—C12—H12A107.8
C1—C7—H7C109.5C13—C12—H12B107.8
H7A—C7—H7B109.5C12—C13—H13A108.6
H7A—C7—H7C109.5C12—C13—H13B108.6
H7B—C7—H7C109.5H13A—C13—H13B107.6
O3—C8—N1122.08 (19)C14—C13—C12114.7 (2)
O3—C8—N2123.79 (19)C14—C13—H13A108.6
N2—C8—N1114.12 (19)C14—C13—H13B108.6
N3—C9—H9AA107.4N3—C14—C13117.40 (19)
N3—C9—H9AB107.4N3—C14—H14A106.7 (13)
N3—C9—H9BC108.2N3—C14—H14B105.7 (15)
N3—C9—H9BD108.2C13—C14—H14A108.9 (14)
N3—C9—C10A119.82 (19)C13—C14—H14B108.8 (14)
H9AA—C9—H9AB106.9H14A—C14—H14B109 (2)
S1—N1—C8—O33.0 (3)C2—C3—C4—S1178.07 (17)
S1—N1—C8—N2177.16 (15)C2—C3—C4—C50.2 (3)
S1—C4—C5—C6177.36 (17)C3—C4—C5—C60.5 (3)
O1—S1—N1—C8172.84 (17)C4—S1—N1—C858.0 (2)
O1—S1—C4—C339.22 (19)C4—C5—C6—C11.0 (3)
O1—S1—C4—C5138.67 (17)C6—C1—C2—C30.0 (3)
O2—S1—N1—C858.76 (19)C7—C1—C2—C3179.1 (2)
O2—S1—C4—C3171.75 (16)C7—C1—C6—C5178.4 (2)
O2—S1—C4—C56.1 (2)C8—N2—N3—C9111.5 (2)
N1—S1—C4—C371.41 (19)C8—N2—N3—C14119.3 (2)
N1—S1—C4—C5110.70 (18)C9—N3—C14—C1362.4 (3)
N2—N3—C9—C10A73.6 (3)C9—C10A—C11—C1273.5 (3)
N2—N3—C9—C10B140.4 (4)C9—C10B—C11—C1276.7 (10)
N2—N3—C14—C1364.2 (3)C10A—C11—C12—C1317.9 (4)
N3—N2—C8—O3177.22 (18)C10B—C11—C12—C1345.7 (4)
N3—N2—C8—N13.0 (3)C11—C12—C13—C1452.0 (3)
N3—C9—C10A—C1173.7 (3)C12—C13—C14—N384.2 (3)
N3—C9—C10B—C1178.8 (10)C14—N3—C9—C10A52.9 (3)
C1—C2—C3—C40.5 (3)C14—N3—C9—C10B13.9 (4)
C2—C1—C6—C50.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.83 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.360 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.3186 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1502 (8) ÅCell parameters from 4337 reflections
c = 13.4244 (11) Åθ = 2.3–27.4°
α = 79.314 (7)°µ = 0.23 mm1
β = 87.303 (7)°T = 225 K
γ = 85.948 (7)°Block, colourless
V = 760.32 (11) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3111 independent reflections
Radiation source: Enhance (Mo) X-ray Source2425 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 2.3°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.926, Tmax = 1.000l = 1616
12225 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.035P)2 + 0.266P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3111 reflectionsΔρmax = 0.27 e Å3
218 parametersΔρmin = 0.29 e Å3
2 restraints
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.02064 (8)0.26910 (5)0.22470 (4)0.03595 (16)
O10.1400 (2)0.15506 (16)0.18281 (11)0.0477 (4)
O20.2046 (2)0.26908 (16)0.23244 (11)0.0468 (4)
O30.0693 (2)0.45636 (15)0.38274 (10)0.0384 (3)
N10.1134 (3)0.2518 (2)0.33898 (13)0.0371 (4)
H10.211 (3)0.197 (3)0.3521 (17)0.041 (7)*
N20.1619 (3)0.3191 (2)0.49142 (13)0.0403 (4)
H20.141 (3)0.378 (2)0.5305 (16)0.039 (6)*
N30.3167 (3)0.19950 (18)0.50980 (12)0.0376 (4)
C10.2042 (3)0.7193 (2)0.05232 (14)0.0366 (5)
C20.3547 (3)0.6034 (3)0.07830 (17)0.0454 (5)
H2A0.49610.61830.05920.055*
C30.3022 (3)0.4659 (2)0.13183 (16)0.0430 (5)
H30.40640.38940.14840.052*
C40.0927 (3)0.4443 (2)0.16025 (14)0.0309 (4)
C50.0612 (3)0.5579 (2)0.13603 (16)0.0405 (5)
H50.20210.54310.15620.049*
C60.0052 (3)0.6942 (2)0.08150 (16)0.0438 (5)
H60.10990.77020.06420.053*
C70.2654 (4)0.8690 (3)0.00424 (18)0.0535 (6)
H7A0.40350.85870.03620.080*
H7B0.26830.93670.04230.080*
H7C0.16350.90710.05500.080*
C80.0604 (3)0.3506 (2)0.40424 (14)0.0318 (4)
C90.5286 (3)0.2557 (3)0.51235 (16)0.0474 (5)
H9AA0.54540.33290.45290.057*0.838 (5)
H9AB0.63220.17480.50480.057*0.838 (5)
H9BC0.59840.25750.44630.057*0.162 (5)
H9BD0.51070.35780.52320.057*0.162 (5)
C10A0.5872 (4)0.3173 (3)0.60146 (19)0.0431 (8)0.838 (5)
H10A0.47340.38710.61720.052*0.838 (5)
H10B0.71330.37240.58340.052*0.838 (5)
C10B0.6699 (16)0.1716 (14)0.5894 (4)0.053 (5)0.162 (5)
H10C0.81490.19410.56860.064*0.162 (5)
H10D0.65840.06620.59040.064*0.162 (5)
C110.6298 (4)0.2002 (3)0.69633 (17)0.0537 (6)
H11A0.72340.12100.67660.064*0.838 (5)
H11B0.70670.24580.74220.064*0.838 (5)
H11C0.75590.16510.73450.064*0.162 (5)
H11D0.61150.30710.69320.064*0.162 (5)
C120.4417 (3)0.1300 (3)0.75479 (16)0.0494 (6)
H12A0.41540.17500.81450.059*
H12B0.48120.02530.77810.059*
C130.2353 (3)0.1408 (2)0.70054 (15)0.0405 (5)
H13A0.17860.24360.68970.049*
H13B0.13430.08150.74420.050 (6)*
C140.2540 (4)0.0894 (3)0.59933 (17)0.0455 (5)
H14A0.359 (4)0.004 (3)0.6023 (17)0.058 (7)*
H14B0.120 (4)0.059 (2)0.5849 (16)0.047 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0461 (3)0.0299 (3)0.0325 (3)0.0010 (2)0.0089 (2)0.0061 (2)
O10.0707 (10)0.0336 (8)0.0411 (9)0.0074 (7)0.0109 (7)0.0146 (7)
O20.0445 (8)0.0437 (9)0.0517 (9)0.0103 (7)0.0102 (7)0.0023 (7)
O30.0447 (8)0.0350 (8)0.0341 (8)0.0062 (7)0.0026 (6)0.0054 (6)
N10.0480 (11)0.0318 (10)0.0307 (9)0.0076 (8)0.0087 (8)0.0059 (7)
N20.0552 (11)0.0343 (10)0.0319 (10)0.0106 (8)0.0086 (8)0.0107 (8)
N30.0455 (10)0.0333 (9)0.0329 (9)0.0053 (8)0.0084 (7)0.0048 (7)
C10.0451 (12)0.0396 (12)0.0265 (10)0.0072 (10)0.0052 (9)0.0069 (9)
C20.0332 (11)0.0538 (14)0.0490 (13)0.0068 (10)0.0014 (9)0.0077 (11)
C30.0364 (11)0.0410 (13)0.0496 (13)0.0071 (9)0.0048 (9)0.0059 (10)
C40.0362 (10)0.0307 (10)0.0261 (9)0.0008 (8)0.0042 (8)0.0068 (8)
C50.0322 (10)0.0399 (12)0.0449 (12)0.0025 (9)0.0009 (9)0.0025 (10)
C60.0425 (12)0.0381 (12)0.0456 (13)0.0076 (10)0.0042 (10)0.0025 (10)
C70.0641 (15)0.0484 (14)0.0470 (14)0.0156 (12)0.0085 (11)0.0001 (11)
C80.0378 (11)0.0283 (10)0.0285 (10)0.0052 (9)0.0023 (8)0.0030 (8)
C90.0494 (13)0.0515 (14)0.0389 (12)0.0016 (11)0.0014 (10)0.0025 (10)
C10A0.0383 (14)0.0412 (16)0.0514 (17)0.0083 (11)0.0035 (12)0.0112 (12)
C10B0.033 (7)0.072 (11)0.049 (9)0.000 (7)0.003 (6)0.004 (8)
C110.0442 (13)0.0742 (17)0.0439 (13)0.0045 (12)0.0104 (10)0.0118 (12)
C120.0490 (13)0.0605 (15)0.0354 (12)0.0039 (11)0.0045 (10)0.0018 (11)
C130.0417 (11)0.0388 (12)0.0372 (11)0.0054 (9)0.0016 (9)0.0035 (9)
C140.0561 (15)0.0336 (12)0.0472 (13)0.0075 (11)0.0116 (11)0.0040 (10)
Geometric parameters (Å, º) top
S1—O11.4283 (15)C9—H9AA0.9700
S1—O21.4218 (15)C9—H9AB0.9700
S1—N11.6442 (18)C9—H9BC0.9700
S1—C41.7542 (19)C9—H9BD0.9700
O3—C81.224 (2)C9—C10A1.486 (3)
N1—H10.77 (2)C9—C10B1.467 (6)
N1—C81.386 (3)C10A—H10A0.9700
N2—H20.82 (2)C10A—H10B0.9700
N2—N31.409 (2)C10A—C111.526 (3)
N2—C81.335 (3)C10B—H10C0.9700
N3—C91.472 (3)C10B—H10D0.9700
N3—C141.476 (3)C10B—C111.513 (6)
C1—C21.379 (3)C11—H11A0.9700
C1—C61.385 (3)C11—H11B0.9700
C1—C71.504 (3)C11—H11C0.9700
C2—H2A0.9300C11—H11D0.9700
C2—C31.382 (3)C11—C121.508 (3)
C3—H30.9300C12—H12A0.9700
C3—C41.378 (3)C12—H12B0.9700
C4—C51.376 (3)C12—C131.512 (3)
C5—H50.9300C13—H13A0.9700
C5—C61.385 (3)C13—H13B0.9700
C6—H60.9300C13—C141.515 (3)
C7—H7A0.9600C14—H14A0.98 (3)
C7—H7B0.9600C14—H14B0.95 (2)
C7—H7C0.9600
O1—S1—N1103.50 (9)H9BC—C9—H9BD107.4
O1—S1—C4109.43 (9)C10A—C9—H9AA107.4
O2—S1—O1119.67 (9)C10A—C9—H9AB107.4
O2—S1—N1109.00 (9)C10B—C9—N3116.2 (6)
O2—S1—C4108.91 (9)C10B—C9—H9BC108.2
N1—S1—C4105.34 (9)C10B—C9—H9BD108.2
S1—N1—H1117.6 (17)C9—C10A—H10A108.7
C8—N1—S1124.09 (15)C9—C10A—H10B108.7
C8—N1—H1116.6 (17)C9—C10A—C11114.4 (2)
N3—N2—H2121.4 (15)H10A—C10A—H10B107.6
C8—N2—H2117.1 (15)C11—C10A—H10A108.7
C8—N2—N3121.12 (17)C11—C10A—H10B108.7
N2—N3—C9110.35 (16)C9—C10B—H10C108.2
N2—N3—C14110.62 (17)C9—C10B—H10D108.2
C9—N3—C14115.46 (17)C9—C10B—C11116.2 (4)
C2—C1—C6117.79 (19)H10C—C10B—H10D107.4
C2—C1—C7121.25 (19)C11—C10B—H10C108.2
C6—C1—C7121.0 (2)C11—C10B—H10D108.2
C1—C2—H2A118.9C10A—C11—H11A107.8
C1—C2—C3122.12 (19)C10A—C11—H11B107.8
C3—C2—H2A118.9C10B—C11—H11C108.1
C2—C3—H3120.6C10B—C11—H11D108.1
C4—C3—C2118.86 (19)H11A—C11—H11B107.2
C4—C3—H3120.6H11C—C11—H11D107.3
C3—C4—S1119.76 (15)C12—C11—C10A117.89 (19)
C5—C4—S1119.73 (14)C12—C11—C10B116.7 (6)
C5—C4—C3120.48 (18)C12—C11—H11A107.8
C4—C5—H5120.2C12—C11—H11B107.8
C4—C5—C6119.66 (18)C12—C11—H11C108.1
C6—C5—H5120.2C12—C11—H11D108.1
C1—C6—H6119.5C11—C12—H12A107.9
C5—C6—C1121.08 (19)C11—C12—H12B107.9
C5—C6—H6119.5C11—C12—C13117.71 (18)
C1—C7—H7A109.5H12A—C12—H12B107.2
C1—C7—H7B109.5C13—C12—H12A107.9
C1—C7—H7C109.5C13—C12—H12B107.9
H7A—C7—H7B109.5C12—C13—H13A108.6
H7A—C7—H7C109.5C12—C13—H13B108.6
H7B—C7—H7C109.5C12—C13—C14114.55 (19)
O3—C8—N1122.08 (18)H13A—C13—H13B107.6
O3—C8—N2123.83 (18)C14—C13—H13A108.6
N2—C8—N1114.09 (18)C14—C13—H13B108.6
N3—C9—H9AA107.4N3—C14—C13117.15 (17)
N3—C9—H9AB107.4N3—C14—H14A106.1 (14)
N3—C9—H9BC108.2N3—C14—H14B105.8 (13)
N3—C9—H9BD108.2C13—C14—H14A110.1 (14)
N3—C9—C10A119.81 (18)C13—C14—H14B108.7 (13)
H9AA—C9—H9AB106.9H14A—C14—H14B108.6 (19)
S1—N1—C8—O33.4 (3)C2—C3—C4—S1177.97 (16)
S1—N1—C8—N2176.96 (14)C2—C3—C4—C50.3 (3)
S1—C4—C5—C6177.35 (16)C3—C4—C5—C60.9 (3)
O1—S1—N1—C8172.54 (16)C4—S1—N1—C857.67 (18)
O1—S1—C4—C339.22 (18)C4—C5—C6—C11.2 (3)
O1—S1—C4—C5139.02 (16)C6—C1—C2—C30.1 (3)
O2—S1—N1—C859.07 (18)C7—C1—C2—C3178.82 (19)
O2—S1—C4—C3171.72 (16)C7—C1—C6—C5178.2 (2)
O2—S1—C4—C56.52 (19)C8—N2—N3—C9111.5 (2)
N1—S1—C4—C371.48 (18)C8—N2—N3—C14119.5 (2)
N1—S1—C4—C5110.28 (17)C9—N3—C14—C1362.5 (3)
N2—N3—C9—C10A74.0 (2)C9—C10A—C11—C1274.8 (3)
N2—N3—C9—C10B140.6 (4)C9—C10B—C11—C1275.9 (10)
N2—N3—C14—C1363.7 (2)C10A—C11—C12—C1319.2 (3)
N3—N2—C8—O3177.07 (17)C10B—C11—C12—C1344.9 (4)
N3—N2—C8—N13.3 (3)C11—C12—C13—C1451.8 (3)
N3—C9—C10A—C1173.5 (3)C12—C13—C14—N385.1 (3)
N3—C9—C10B—C1178.9 (10)C14—N3—C9—C10A52.3 (3)
C1—C2—C3—C40.1 (3)C14—N3—C9—C10B14.2 (4)
C2—C1—C6—C50.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.82 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.368 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.3064 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1298 (7) ÅCell parameters from 4645 reflections
c = 13.3984 (11) Åθ = 2.3–27.5°
α = 79.397 (7)°µ = 0.23 mm1
β = 87.344 (7)°T = 200 K
γ = 85.986 (6)°Block, colourless
V = 755.95 (11) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3090 independent reflections
Radiation source: Enhance (Mo) X-ray Source2455 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 2.3°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.893, Tmax = 1.000l = 1616
12156 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.035P)2 + 0.314P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3090 reflectionsΔρmax = 0.32 e Å3
218 parametersΔρmin = 0.32 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.02035 (8)0.26832 (5)0.22422 (3)0.03102 (15)
O10.1403 (2)0.15420 (15)0.18212 (10)0.0416 (4)
O20.2054 (2)0.26795 (15)0.23202 (11)0.0408 (4)
O30.0705 (2)0.45561 (14)0.38268 (9)0.0333 (3)
N10.1133 (3)0.25089 (19)0.33872 (12)0.0326 (4)
H10.211 (3)0.195 (2)0.3524 (16)0.034 (6)*
N20.1613 (3)0.31804 (19)0.49204 (13)0.0352 (4)
H20.141 (3)0.376 (2)0.5319 (16)0.036 (6)*
N30.3181 (3)0.19895 (18)0.50988 (12)0.0333 (4)
C10.2033 (3)0.7202 (2)0.05218 (13)0.0313 (4)
C20.3546 (3)0.6041 (2)0.07783 (15)0.0382 (5)
H2A0.49610.61920.05860.046*
C30.3025 (3)0.4661 (2)0.13121 (15)0.0374 (5)
H30.40700.38940.14740.045*
C40.0924 (3)0.4444 (2)0.16000 (13)0.0270 (4)
C50.0626 (3)0.5580 (2)0.13624 (15)0.0362 (5)
H50.20350.54310.15670.043*
C60.0065 (3)0.6948 (2)0.08148 (15)0.0372 (5)
H60.11150.77080.06410.045*
C70.2648 (4)0.8701 (2)0.00409 (16)0.0458 (5)
H7A0.40450.86030.03470.069*
H7B0.26440.93840.04250.069*
H7C0.16470.90730.05600.069*
C80.0601 (3)0.3498 (2)0.40443 (13)0.0287 (4)
C90.5296 (3)0.2567 (2)0.51205 (15)0.0411 (5)
H9AA0.54460.33470.45280.049*0.854 (5)
H9AB0.63430.17650.50360.049*0.854 (5)
H9BC0.51110.35850.52400.049*0.146 (5)
H9BD0.59900.25980.44560.049*0.146 (5)
C10A0.5886 (4)0.3180 (3)0.60185 (18)0.0377 (7)0.854 (5)
H10A0.47410.38720.61820.045*0.854 (5)
H10B0.71430.37390.58390.045*0.854 (5)
C10B0.6716 (16)0.1705 (13)0.5890 (4)0.042 (5)0.146 (5)
H10C0.81710.19180.56800.050*0.146 (5)
H10D0.65780.06510.59000.050*0.146 (5)
C110.6327 (3)0.1997 (3)0.69638 (16)0.0450 (5)
H11A0.72440.11990.67580.054*0.854 (5)
H11B0.71220.24430.74210.054*0.854 (5)
H11C0.75920.16400.73430.054*0.146 (5)
H11D0.61570.30690.69310.054*0.146 (5)
C120.4436 (3)0.1305 (3)0.75573 (15)0.0426 (5)
H12A0.41710.17720.81490.051*
H12B0.48270.02580.78010.051*
C130.2367 (3)0.1404 (2)0.70079 (14)0.0345 (5)
H13A0.13550.08090.74440.041*
H13B0.17940.24330.68970.041 (6)*
C140.2561 (4)0.0885 (2)0.59945 (16)0.0391 (5)
H14A0.361 (4)0.004 (3)0.6033 (17)0.052 (7)*
H14B0.121 (4)0.054 (2)0.5847 (16)0.049 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0396 (3)0.0255 (3)0.0284 (3)0.0006 (2)0.0078 (2)0.00499 (19)
O10.0606 (9)0.0301 (8)0.0360 (8)0.0061 (7)0.0098 (7)0.0125 (6)
O20.0395 (8)0.0372 (8)0.0452 (8)0.0093 (6)0.0079 (6)0.0022 (7)
O30.0382 (7)0.0307 (7)0.0295 (7)0.0058 (6)0.0024 (6)0.0044 (6)
N10.0424 (10)0.0283 (9)0.0264 (9)0.0076 (8)0.0085 (7)0.0045 (7)
N20.0495 (10)0.0300 (9)0.0268 (9)0.0095 (8)0.0071 (8)0.0096 (8)
N30.0413 (9)0.0285 (9)0.0293 (9)0.0058 (7)0.0082 (7)0.0040 (7)
C10.0389 (11)0.0336 (11)0.0227 (9)0.0052 (9)0.0042 (8)0.0061 (8)
C20.0290 (10)0.0431 (12)0.0418 (12)0.0046 (9)0.0015 (9)0.0053 (10)
C30.0319 (10)0.0362 (11)0.0425 (12)0.0064 (9)0.0030 (9)0.0053 (9)
C40.0328 (10)0.0252 (9)0.0229 (9)0.0020 (8)0.0050 (7)0.0049 (7)
C50.0287 (10)0.0375 (12)0.0393 (11)0.0013 (9)0.0017 (8)0.0003 (9)
C60.0366 (11)0.0325 (11)0.0384 (11)0.0073 (9)0.0039 (9)0.0015 (9)
C70.0545 (13)0.0407 (13)0.0413 (12)0.0130 (11)0.0065 (10)0.0003 (10)
C80.0334 (10)0.0259 (10)0.0261 (10)0.0058 (8)0.0032 (8)0.0022 (8)
C90.0438 (12)0.0433 (12)0.0341 (11)0.0020 (10)0.0010 (9)0.0018 (9)
C10A0.0346 (13)0.0366 (15)0.0431 (15)0.0066 (10)0.0035 (10)0.0098 (11)
C10B0.028 (7)0.066 (11)0.027 (8)0.009 (7)0.001 (6)0.001 (7)
C110.0372 (11)0.0600 (15)0.0386 (12)0.0016 (10)0.0087 (9)0.0102 (11)
C120.0419 (12)0.0520 (14)0.0308 (11)0.0047 (10)0.0034 (9)0.0016 (10)
C130.0351 (10)0.0331 (11)0.0320 (11)0.0044 (9)0.0012 (8)0.0026 (8)
C140.0506 (13)0.0267 (11)0.0397 (12)0.0059 (10)0.0123 (10)0.0010 (9)
Geometric parameters (Å, º) top
S1—O11.4291 (14)C9—H9AA0.9700
S1—O21.4231 (14)C9—H9AB0.9700
S1—N11.6441 (17)C9—H9BC0.9700
S1—C41.7575 (19)C9—H9BD0.9700
O3—C81.226 (2)C9—C10A1.489 (3)
N1—H10.78 (2)C9—C10B1.474 (6)
N1—C81.388 (2)C10A—H10A0.9700
N2—H20.82 (2)C10A—H10B0.9700
N2—N31.412 (2)C10A—C111.528 (3)
N2—C81.337 (2)C10B—H10C0.9700
N3—C91.472 (3)C10B—H10D0.9700
N3—C141.475 (3)C10B—C111.516 (6)
C1—C21.381 (3)C11—H11A0.9700
C1—C61.385 (3)C11—H11B0.9700
C1—C71.503 (3)C11—H11C0.9700
C2—H2A0.9300C11—H11D0.9700
C2—C31.382 (3)C11—C121.512 (3)
C3—H30.9300C12—H12A0.9700
C3—C41.380 (3)C12—H12B0.9700
C4—C51.377 (3)C12—C131.517 (3)
C5—H50.9300C13—H13A0.9700
C5—C61.387 (3)C13—H13B0.9700
C6—H60.9300C13—C141.516 (3)
C7—H7A0.9600C14—H14A0.97 (2)
C7—H7B0.9600C14—H14B0.97 (2)
C7—H7C0.9600
O1—S1—N1103.45 (9)H9AA—C9—H9AB106.9
O1—S1—C4109.48 (9)H9BC—C9—H9BD107.5
O2—S1—O1119.71 (9)C10A—C9—H9AA107.4
O2—S1—N1108.97 (9)C10A—C9—H9AB107.4
O2—S1—C4108.95 (9)C10B—C9—H9BC108.4
N1—S1—C4105.26 (8)C10B—C9—H9BD108.4
S1—N1—H1117.7 (16)C9—C10A—H10A108.7
C8—N1—S1124.13 (15)C9—C10A—H10B108.7
C8—N1—H1116.7 (16)C9—C10A—C11114.25 (19)
N3—N2—H2120.4 (15)H10A—C10A—H10B107.6
C8—N2—H2118.1 (15)C11—C10A—H10A108.7
C8—N2—N3120.97 (16)C11—C10A—H10B108.7
N2—N3—C9110.30 (15)C9—C10B—H10C108.3
N2—N3—C14110.32 (16)C9—C10B—H10D108.3
C9—N3—C14115.72 (16)C9—C10B—C11115.9 (4)
C2—C1—C6117.85 (18)H10C—C10B—H10D107.4
C2—C1—C7121.05 (18)C11—C10B—H10C108.3
C6—C1—C7121.09 (19)C11—C10B—H10D108.3
C1—C2—H2A118.9C10A—C11—H11A107.9
C1—C2—C3122.11 (18)C10A—C11—H11B107.9
C3—C2—H2A118.9C10B—C11—H11C108.1
C2—C3—H3120.6C10B—C11—H11D108.1
C4—C3—C2118.75 (18)H11A—C11—H11B107.2
C4—C3—H3120.6H11C—C11—H11D107.3
C3—C4—S1119.70 (15)C12—C11—C10A117.59 (18)
C5—C4—S1119.55 (14)C12—C11—C10B117.0 (5)
C5—C4—C3120.71 (18)C12—C11—H11A107.9
C4—C5—H5120.3C12—C11—H11B107.9
C4—C5—C6119.41 (17)C12—C11—H11C108.1
C6—C5—H5120.3C12—C11—H11D108.1
C1—C6—C5121.15 (18)C11—C12—H12A108.0
C1—C6—H6119.4C11—C12—H12B108.0
C5—C6—H6119.4C11—C12—C13117.39 (17)
C1—C7—H7A109.5H12A—C12—H12B107.2
C1—C7—H7B109.5C13—C12—H12A108.0
C1—C7—H7C109.5C13—C12—H12B108.0
H7A—C7—H7B109.5C12—C13—H13A108.6
H7A—C7—H7C109.5C12—C13—H13B108.6
H7B—C7—H7C109.5H13A—C13—H13B107.6
O3—C8—N1121.79 (17)C14—C13—C12114.69 (18)
O3—C8—N2124.00 (17)C14—C13—H13A108.6
N2—C8—N1114.21 (17)C14—C13—H13B108.6
N3—C9—H9AA107.4N3—C14—C13117.02 (16)
N3—C9—H9AB107.4N3—C14—H14A106.6 (13)
N3—C9—H9BC108.4N3—C14—H14B106.4 (13)
N3—C9—H9BD108.4C13—C14—H14A109.5 (13)
N3—C9—C10A119.72 (17)C13—C14—H14B109.3 (13)
N3—C9—C10B115.4 (6)H14A—C14—H14B107.6 (18)
S1—N1—C8—O33.5 (3)C2—C3—C4—S1177.89 (15)
S1—N1—C8—N2177.18 (14)C2—C3—C4—C50.1 (3)
S1—C4—C5—C6177.07 (15)C3—C4—C5—C60.9 (3)
O1—S1—N1—C8172.53 (15)C4—S1—N1—C857.66 (17)
O1—S1—C4—C338.82 (18)C4—C5—C6—C11.4 (3)
O1—S1—C4—C5139.22 (15)C6—C1—C2—C30.2 (3)
O2—S1—N1—C859.08 (17)C7—C1—C2—C3178.77 (18)
O2—S1—C4—C3171.45 (15)C7—C1—C6—C5177.93 (18)
O2—S1—C4—C56.59 (18)C8—N2—N3—C9110.86 (19)
N1—S1—C4—C371.80 (17)C8—N2—N3—C14120.05 (18)
N1—S1—C4—C5110.16 (16)C9—N3—C14—C1362.6 (2)
N2—N3—C9—C10A74.4 (2)C9—C10A—C11—C1275.9 (3)
N2—N3—C9—C10B141.1 (3)C9—C10B—C11—C1276.3 (10)
N2—N3—C14—C1363.5 (2)C10A—C11—C12—C1320.7 (3)
N3—N2—C8—O3176.64 (16)C10B—C11—C12—C1343.9 (4)
N3—N2—C8—N14.0 (2)C11—C12—C13—C1451.0 (3)
N3—C9—C10A—C1173.2 (3)C12—C13—C14—N385.3 (2)
N3—C9—C10B—C1180.0 (9)C14—N3—C9—C10A51.7 (3)
C1—C2—C3—C40.3 (3)C14—N3—C9—C10B15.0 (4)
C2—C1—C6—C51.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.82 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.380 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.2891 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0960 (4) ÅCell parameters from 4856 reflections
c = 13.3659 (5) Åθ = 2.3–28.2°
α = 79.436 (4)°µ = 0.23 mm1
β = 87.381 (3)°T = 175 K
γ = 86.026 (4)°Block, colourless
V = 749.41 (6) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3064 independent reflections
Radiation source: Enhance (Mo) X-ray Source2504 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 1.6°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.851, Tmax = 1.000l = 1616
12090 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0373P)2 + 0.3174P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3064 reflectionsΔρmax = 0.33 e Å3
218 parametersΔρmin = 0.35 e Å3
2 restraints
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.02002 (7)0.26779 (5)0.22385 (3)0.02655 (14)
O10.1405 (2)0.15383 (14)0.18145 (10)0.0354 (3)
O20.2064 (2)0.26729 (15)0.23153 (10)0.0345 (3)
O30.07128 (19)0.45497 (14)0.38284 (9)0.0285 (3)
N10.1134 (3)0.24982 (18)0.33884 (12)0.0281 (4)
H10.211 (3)0.197 (2)0.3511 (16)0.032 (6)*
N20.1607 (3)0.31714 (18)0.49256 (12)0.0307 (4)
H20.141 (3)0.380 (3)0.5315 (16)0.038 (6)*
N30.3190 (2)0.19847 (17)0.50973 (11)0.0290 (4)
C10.2026 (3)0.7208 (2)0.05212 (13)0.0270 (4)
C20.3549 (3)0.6044 (2)0.07748 (14)0.0321 (4)
H2A0.49670.61970.05810.038*
C30.3027 (3)0.4658 (2)0.13083 (15)0.0315 (4)
H30.40740.38880.14700.038*
C40.0918 (3)0.44428 (19)0.15965 (13)0.0232 (4)
C50.0636 (3)0.5583 (2)0.13620 (14)0.0303 (4)
H50.20480.54310.15690.036*
C60.0079 (3)0.6953 (2)0.08171 (14)0.0321 (4)
H60.11330.77160.06460.039*
C70.2633 (3)0.8713 (2)0.00396 (15)0.0385 (5)
H7A0.40320.86180.03490.058*
H7B0.26320.93960.04290.058*
H7C0.16250.90860.05580.058*
C80.0594 (3)0.34913 (19)0.40446 (13)0.0236 (4)
C90.5309 (3)0.2571 (2)0.51145 (15)0.0356 (5)
H9AA0.54510.33570.45220.043*0.869 (5)
H9AB0.63630.17710.50270.043*0.869 (5)
H9BC0.51260.35900.52410.043*0.131 (5)
H9BD0.60030.26070.44480.043*0.131 (5)
C10A0.5897 (3)0.3186 (2)0.60211 (17)0.0318 (7)0.869 (5)
H10A0.47410.38710.61900.038*0.869 (5)
H10B0.71490.37570.58420.038*0.869 (5)
C10B0.6723 (16)0.1684 (14)0.5888 (4)0.038 (5)0.131 (5)
H10C0.81890.18720.56750.045*0.131 (5)
H10D0.65460.06290.59020.045*0.131 (5)
C110.6358 (3)0.1992 (2)0.69625 (15)0.0376 (5)
H11A0.72540.11870.67480.045*0.869 (5)
H11B0.71810.24310.74170.045*0.869 (5)
H11C0.62020.30690.69250.045*0.131 (5)
H11D0.76290.16310.73400.045*0.131 (5)
C120.4453 (3)0.1310 (2)0.75679 (15)0.0362 (5)
H12A0.48380.02620.78240.043*
H12B0.41870.17970.81530.043*
C130.2385 (3)0.1403 (2)0.70126 (14)0.0297 (4)
H13A0.18090.24350.68990.036*
H13B0.13680.08070.74490.042 (6)*
C140.2586 (4)0.0875 (2)0.59955 (15)0.0337 (5)
H14A0.364 (3)0.003 (3)0.6040 (15)0.038 (6)*
H14B0.123 (3)0.053 (2)0.5850 (16)0.041 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0336 (3)0.0221 (2)0.0243 (2)0.00045 (18)0.00668 (18)0.00444 (18)
O10.0525 (8)0.0252 (7)0.0300 (7)0.0056 (6)0.0083 (6)0.0105 (6)
O20.0330 (7)0.0309 (8)0.0389 (8)0.0073 (6)0.0067 (6)0.0014 (6)
O30.0326 (7)0.0265 (7)0.0255 (7)0.0047 (6)0.0019 (5)0.0047 (5)
N10.0353 (9)0.0237 (9)0.0246 (8)0.0068 (7)0.0071 (7)0.0044 (7)
N20.0419 (9)0.0265 (9)0.0243 (8)0.0081 (7)0.0060 (7)0.0088 (7)
N30.0352 (9)0.0249 (8)0.0261 (8)0.0052 (7)0.0069 (7)0.0040 (6)
C10.0332 (10)0.0294 (10)0.0194 (9)0.0051 (8)0.0033 (7)0.0053 (7)
C20.0242 (9)0.0377 (11)0.0342 (11)0.0040 (8)0.0021 (8)0.0064 (9)
C30.0270 (10)0.0307 (11)0.0359 (11)0.0058 (8)0.0033 (8)0.0057 (9)
C40.0280 (9)0.0227 (9)0.0196 (8)0.0005 (7)0.0045 (7)0.0053 (7)
C50.0231 (9)0.0318 (11)0.0330 (10)0.0011 (8)0.0001 (8)0.0005 (8)
C60.0306 (10)0.0279 (10)0.0343 (11)0.0056 (8)0.0026 (8)0.0012 (8)
C70.0456 (12)0.0348 (12)0.0345 (11)0.0106 (9)0.0045 (9)0.0007 (9)
C80.0276 (9)0.0206 (9)0.0222 (9)0.0030 (7)0.0031 (7)0.0029 (7)
C90.0374 (11)0.0377 (12)0.0299 (10)0.0030 (9)0.0006 (8)0.0015 (9)
C10A0.0287 (12)0.0301 (13)0.0376 (13)0.0047 (9)0.0031 (9)0.0083 (10)
C10B0.017 (7)0.062 (12)0.028 (8)0.006 (7)0.003 (6)0.010 (7)
C110.0305 (10)0.0497 (13)0.0334 (11)0.0017 (9)0.0073 (8)0.0086 (10)
C120.0353 (11)0.0448 (12)0.0263 (10)0.0038 (9)0.0031 (8)0.0028 (9)
C130.0296 (10)0.0274 (10)0.0290 (10)0.0035 (8)0.0006 (8)0.0030 (8)
C140.0424 (12)0.0236 (10)0.0357 (11)0.0050 (9)0.0096 (9)0.0037 (8)
Geometric parameters (Å, º) top
S1—O11.4273 (14)C9—H9AA0.9700
S1—O21.4236 (13)C9—H9AB0.9700
S1—N11.6464 (16)C9—H9BC0.9700
S1—C41.7543 (18)C9—H9BD0.9700
O3—C81.223 (2)C9—C10A1.495 (3)
N1—H10.76 (2)C9—C10B1.480 (5)
N1—C81.386 (2)C10A—H10A0.9700
N2—H20.84 (2)C10A—H10B0.9700
N2—N31.411 (2)C10A—C111.528 (3)
N2—C81.339 (2)C10B—H10C0.9700
N3—C91.472 (2)C10B—H10D0.9700
N3—C141.474 (2)C10B—C111.517 (6)
C1—C21.382 (3)C11—H11A0.9700
C1—C61.387 (2)C11—H11B0.9700
C1—C71.500 (3)C11—H11C0.9700
C2—H2A0.9300C11—H11D0.9700
C2—C31.382 (3)C11—C121.519 (3)
C3—H30.9300C12—H12A0.9700
C3—C41.381 (2)C12—H12B0.9700
C4—C51.377 (3)C12—C131.516 (3)
C5—H50.9300C13—H13A0.9700
C5—C61.383 (3)C13—H13B0.9700
C6—H60.9300C13—C141.520 (3)
C7—H7A0.9600C14—H14A0.98 (2)
C7—H7B0.9600C14—H14B0.97 (2)
C7—H7C0.9600
O1—S1—N1103.40 (8)H9AA—C9—H9AB107.0
O1—S1—C4109.33 (8)H9BC—C9—H9BD107.6
O2—S1—O1119.78 (8)C10A—C9—H9AA107.5
O2—S1—N1109.02 (8)C10A—C9—H9AB107.5
O2—S1—C4108.88 (8)C10B—C9—H9BC108.7
N1—S1—C4105.44 (8)C10B—C9—H9BD108.7
S1—N1—H1117.2 (16)C9—C10A—H10A108.7
C8—N1—S1123.79 (14)C9—C10A—H10B108.7
C8—N1—H1117.2 (16)C9—C10A—C11114.09 (18)
N3—N2—H2122.0 (15)H10A—C10A—H10B107.6
C8—N2—H2116.4 (15)C11—C10A—H10A108.7
C8—N2—N3120.74 (15)C11—C10A—H10B108.7
N2—N3—C9110.48 (15)C9—C10B—H10C108.4
N2—N3—C14110.16 (15)C9—C10B—H10D108.4
C9—N3—C14115.63 (15)C9—C10B—C11115.7 (4)
C2—C1—C6118.02 (17)H10C—C10B—H10D107.4
C2—C1—C7121.11 (17)C11—C10B—H10C108.4
C6—C1—C7120.86 (18)C11—C10B—H10D108.4
C1—C2—H2A119.0C10A—C11—H11A108.0
C1—C2—C3121.97 (17)C10A—C11—H11B108.0
C3—C2—H2A119.0C10B—C11—H11C108.1
C2—C3—H3120.7C10B—C11—H11D108.1
C4—C3—C2118.60 (17)C10B—C11—C12116.8 (6)
C4—C3—H3120.7H11A—C11—H11B107.3
C3—C4—S1119.52 (14)H11C—C11—H11D107.3
C5—C4—S1119.56 (13)C12—C11—C10A117.15 (17)
C5—C4—C3120.89 (17)C12—C11—H11A108.0
C4—C5—H5120.3C12—C11—H11B108.0
C4—C5—C6119.47 (16)C12—C11—H11C108.1
C6—C5—H5120.3C12—C11—H11D108.1
C1—C6—H6119.5C11—C12—H12A108.1
C5—C6—C1121.03 (17)C11—C12—H12B108.1
C5—C6—H6119.5H12A—C12—H12B107.3
C1—C7—H7A109.5C13—C12—C11116.96 (16)
C1—C7—H7B109.5C13—C12—H12A108.1
C1—C7—H7C109.5C13—C12—H12B108.1
H7A—C7—H7B109.5C12—C13—H13A108.6
H7A—C7—H7C109.5C12—C13—H13B108.6
H7B—C7—H7C109.5C12—C13—C14114.85 (16)
O3—C8—N1122.06 (16)H13A—C13—H13B107.5
O3—C8—N2123.92 (16)C14—C13—H13A108.6
N2—C8—N1114.02 (16)C14—C13—H13B108.6
N3—C9—H9AA107.5N3—C14—C13116.92 (15)
N3—C9—H9AB107.5N3—C14—H14A107.1 (12)
N3—C9—H9BC108.7N3—C14—H14B106.2 (13)
N3—C9—H9BD108.7C13—C14—H14A109.3 (12)
N3—C9—C10A119.37 (16)C13—C14—H14B109.0 (12)
N3—C9—C10B114.3 (6)H14A—C14—H14B107.9 (17)
S1—N1—C8—O33.5 (2)C2—C3—C4—S1177.97 (14)
S1—N1—C8—N2177.23 (13)C2—C3—C4—C50.2 (3)
S1—C4—C5—C6177.19 (14)C3—C4—C5—C61.0 (3)
O1—S1—N1—C8172.42 (15)C4—S1—N1—C857.66 (17)
O1—S1—C4—C338.80 (17)C4—C5—C6—C11.4 (3)
O1—S1—C4—C5139.44 (14)C6—C1—C2—C30.1 (3)
O2—S1—N1—C859.11 (17)C7—C1—C2—C3178.73 (17)
O2—S1—C4—C3171.35 (14)C7—C1—C6—C5177.94 (17)
O2—S1—C4—C56.88 (17)C8—N2—N3—C9110.31 (18)
N1—S1—C4—C371.79 (16)C8—N2—N3—C14120.71 (17)
N1—S1—C4—C5109.98 (15)C9—N3—C14—C1363.1 (2)
N2—N3—C9—C10A74.3 (2)C9—C10A—C11—C1277.4 (2)
N2—N3—C9—C10B141.2 (3)C9—C10B—C11—C1277.2 (10)
N2—N3—C14—C1363.1 (2)C10A—C11—C12—C1322.3 (3)
N3—N2—C8—O3176.13 (16)C10B—C11—C12—C1343.1 (4)
N3—N2—C8—N14.6 (2)C11—C12—C13—C1450.2 (2)
N3—C9—C10A—C1173.5 (2)C12—C13—C14—N385.9 (2)
N3—C9—C10B—C1181.4 (10)C14—N3—C9—C10A51.6 (2)
C1—C2—C3—C40.2 (3)C14—N3—C9—C10B15.2 (4)
C2—C1—C6—C50.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.84 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.388 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.2738 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0824 (4) ÅCell parameters from 5119 reflections
c = 13.3414 (5) Åθ = 2.3–28.8°
α = 79.449 (4)°µ = 0.23 mm1
β = 87.415 (3)°T = 150 K
γ = 86.013 (4)°Block, colourless
V = 745.14 (6) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3045 independent reflections
Radiation source: Enhance (Mo) X-ray Source2540 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 1.6°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.927, Tmax = 1.000l = 1616
12009 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0382P)2 + 0.2704P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3045 reflectionsΔρmax = 0.43 e Å3
218 parametersΔρmin = 0.39 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.98036 (7)0.73262 (5)0.77641 (3)0.02242 (13)
O10.8593 (2)0.84664 (14)0.81909 (9)0.0297 (3)
O21.20715 (19)0.73324 (14)0.76890 (9)0.0292 (3)
O31.07216 (18)0.54545 (13)0.61691 (9)0.0242 (3)
N10.8871 (3)0.75066 (17)0.66118 (11)0.0237 (3)
H10.790 (3)0.805 (2)0.6486 (16)0.029 (6)*
N20.8400 (2)0.68383 (17)0.50685 (12)0.0260 (3)
H20.859 (3)0.623 (2)0.4672 (16)0.030 (5)*
N30.6802 (2)0.80220 (16)0.49024 (11)0.0244 (3)
C10.7980 (3)0.2788 (2)0.94811 (12)0.0228 (4)
C20.6452 (3)0.3953 (2)0.92270 (14)0.0272 (4)
H2A0.50310.37980.94200.033*
C30.6972 (3)0.5341 (2)0.86946 (14)0.0262 (4)
H30.59230.61130.85350.031*
C40.9088 (3)0.55568 (19)0.84036 (12)0.0200 (4)
C51.0651 (3)0.4413 (2)0.86356 (13)0.0257 (4)
H51.20660.45640.84270.031*
C61.0091 (3)0.3040 (2)0.91813 (13)0.0267 (4)
H61.11460.22740.93500.032*
C70.7372 (3)0.1277 (2)1.00388 (14)0.0322 (4)
H7A0.59780.13731.03570.048*
H7B0.83940.08941.05510.048*
H7C0.73540.06000.95650.048*
C80.9412 (3)0.65192 (18)0.59529 (12)0.0201 (4)
C90.4679 (3)0.7426 (2)0.48880 (14)0.0300 (4)
H9AA0.36160.82240.49760.036*0.894 (5)
H9AB0.45440.66380.54810.036*0.894 (5)
H9BC0.39880.73810.55570.036*0.106 (5)
H9BD0.48640.64090.47550.036*0.106 (5)
C10A0.4096 (3)0.6805 (2)0.39756 (15)0.0268 (6)0.894 (5)
H10A0.28510.62230.41550.032*0.894 (5)
H10B0.52650.61310.38030.032*0.894 (5)
C10B0.325 (2)0.8331 (16)0.4112 (4)0.039 (6)0.106 (5)
H10C0.34440.93860.40960.047*0.106 (5)
H10D0.17790.81520.43270.047*0.106 (5)
C110.3613 (3)0.8007 (2)0.30379 (14)0.0307 (4)
H11A0.27700.75750.25870.037*0.894 (5)
H11B0.27310.88160.32590.037*0.894 (5)
H11C0.23380.83640.26590.037*0.106 (5)
H11D0.37680.69270.30820.037*0.106 (5)
C120.5528 (3)0.8683 (2)0.24229 (14)0.0300 (4)
H12A0.57950.81820.18420.036*
H12B0.51430.97300.21580.036*
C130.7605 (3)0.8598 (2)0.29827 (13)0.0246 (4)
H13A0.86240.91940.25450.030*
H13B0.81860.75660.31020.031 (5)*
C140.7391 (3)0.9139 (2)0.39992 (14)0.0282 (4)
H14A0.632 (3)0.995 (2)0.3970 (15)0.031 (5)*
H14B0.875 (3)0.951 (2)0.4164 (15)0.034 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0280 (2)0.0189 (2)0.0207 (2)0.00046 (17)0.00564 (17)0.00375 (17)
O10.0437 (8)0.0216 (7)0.0251 (7)0.0051 (6)0.0074 (6)0.0087 (5)
O20.0284 (7)0.0263 (7)0.0323 (7)0.0062 (5)0.0059 (5)0.0008 (6)
O30.0279 (6)0.0215 (7)0.0221 (6)0.0039 (5)0.0015 (5)0.0031 (5)
N10.0301 (8)0.0202 (8)0.0200 (8)0.0063 (7)0.0062 (6)0.0033 (6)
N20.0344 (9)0.0225 (8)0.0216 (8)0.0070 (7)0.0045 (6)0.0079 (7)
N30.0280 (8)0.0221 (8)0.0224 (8)0.0044 (6)0.0069 (6)0.0030 (6)
C10.0284 (9)0.0247 (9)0.0166 (8)0.0040 (7)0.0030 (7)0.0057 (7)
C20.0206 (9)0.0322 (11)0.0290 (10)0.0041 (7)0.0017 (7)0.0056 (8)
C30.0229 (9)0.0249 (10)0.0299 (10)0.0058 (7)0.0027 (7)0.0048 (8)
C40.0248 (9)0.0194 (9)0.0162 (8)0.0000 (7)0.0032 (7)0.0044 (7)
C50.0209 (9)0.0266 (10)0.0275 (10)0.0006 (7)0.0011 (7)0.0002 (8)
C60.0258 (9)0.0239 (10)0.0275 (10)0.0057 (7)0.0030 (7)0.0005 (8)
C70.0376 (11)0.0294 (11)0.0289 (10)0.0088 (8)0.0034 (8)0.0006 (8)
C80.0236 (8)0.0177 (9)0.0182 (8)0.0026 (7)0.0026 (7)0.0014 (7)
C90.0313 (10)0.0312 (10)0.0260 (10)0.0001 (8)0.0007 (8)0.0021 (8)
C10A0.0238 (11)0.0254 (12)0.0321 (12)0.0049 (8)0.0025 (8)0.0071 (9)
C10B0.018 (9)0.063 (15)0.030 (11)0.007 (9)0.002 (7)0.011 (9)
C110.0245 (9)0.0407 (12)0.0283 (10)0.0002 (8)0.0051 (8)0.0092 (9)
C120.0296 (10)0.0375 (11)0.0214 (9)0.0031 (8)0.0022 (7)0.0027 (8)
C130.0242 (9)0.0234 (10)0.0238 (9)0.0031 (7)0.0002 (7)0.0026 (7)
C140.0350 (11)0.0206 (10)0.0294 (10)0.0032 (8)0.0090 (8)0.0025 (8)
Geometric parameters (Å, º) top
S1—O11.4288 (13)C9—H9AA0.9700
S1—O21.4222 (13)C9—H9AB0.9700
S1—N11.6456 (15)C9—H9BC0.9700
S1—C41.7537 (17)C9—H9BD0.9700
O3—C81.226 (2)C9—C10A1.501 (3)
N1—H10.76 (2)C9—C10B1.490 (6)
N1—C81.383 (2)C10A—H10A0.9700
N2—H20.83 (2)C10A—H10B0.9700
N2—N31.412 (2)C10A—C111.529 (3)
N2—C81.340 (2)C10B—H10C0.9700
N3—C91.475 (2)C10B—H10D0.9700
N3—C141.477 (2)C10B—C111.519 (6)
C1—C21.383 (3)C11—H11A0.9700
C1—C61.388 (2)C11—H11B0.9700
C1—C71.501 (2)C11—H11C0.9700
C2—H2A0.9300C11—H11D0.9700
C2—C31.381 (3)C11—C121.524 (2)
C3—H30.9300C12—H12A0.9700
C3—C41.383 (2)C12—H12B0.9700
C4—C51.380 (2)C12—C131.521 (2)
C5—H50.9300C13—H13A0.9700
C5—C61.384 (2)C13—H13B0.9700
C6—H60.9300C13—C141.522 (3)
C7—H7A0.9600C14—H14A0.96 (2)
C7—H7B0.9600C14—H14B0.99 (2)
C7—H7C0.9600
O1—S1—N1103.50 (8)H9AA—C9—H9AB107.0
O1—S1—C4109.38 (8)H9BC—C9—H9BD107.7
O2—S1—O1119.76 (8)C10A—C9—H9AA107.5
O2—S1—N1108.99 (8)C10A—C9—H9AB107.5
O2—S1—C4108.83 (8)C10B—C9—H9BC108.8
N1—S1—C4105.39 (8)C10B—C9—H9BD108.8
S1—N1—H1117.1 (16)C9—C10A—H10A108.8
C8—N1—S1124.01 (13)C9—C10A—H10B108.8
C8—N1—H1117.2 (16)C9—C10A—C11113.79 (16)
N3—N2—H2121.1 (14)H10A—C10A—H10B107.7
C8—N2—H2117.6 (14)C11—C10A—H10A108.8
C8—N2—N3120.41 (14)C11—C10A—H10B108.8
N2—N3—C9110.48 (14)C9—C10B—H10C108.5
N2—N3—C14110.10 (14)C9—C10B—H10D108.5
C9—N3—C14115.52 (14)C9—C10B—C11115.0 (4)
C2—C1—C6118.08 (16)H10C—C10B—H10D107.5
C2—C1—C7121.10 (16)C11—C10B—H10C108.5
C6—C1—C7120.80 (16)C11—C10B—H10D108.5
C1—C2—H2A119.0C10A—C11—H11A108.1
C3—C2—C1122.00 (16)C10A—C11—H11B108.1
C3—C2—H2A119.0C10B—C11—H11C108.0
C2—C3—H3120.7C10B—C11—H11D108.0
C2—C3—C4118.57 (16)C10B—C11—C12117.0 (7)
C4—C3—H3120.7H11A—C11—H11B107.3
C3—C4—S1119.45 (13)H11C—C11—H11D107.3
C5—C4—S1119.57 (12)C12—C11—C10A116.78 (16)
C5—C4—C3120.94 (16)C12—C11—H11A108.1
C4—C5—H5120.3C12—C11—H11B108.1
C4—C5—C6119.32 (15)C12—C11—H11C108.0
C6—C5—H5120.3C12—C11—H11D108.0
C1—C6—H6119.5C11—C12—H12A108.1
C5—C6—C1121.08 (16)C11—C12—H12B108.1
C5—C6—H6119.5H12A—C12—H12B107.3
C1—C7—H7A109.5C13—C12—C11116.71 (15)
C1—C7—H7B109.5C13—C12—H12A108.1
C1—C7—H7C109.5C13—C12—H12B108.1
H7A—C7—H7B109.5C12—C13—H13A108.6
H7A—C7—H7C109.5C12—C13—H13B108.6
H7B—C7—H7C109.5C12—C13—C14114.74 (15)
O3—C8—N1122.01 (15)H13A—C13—H13B107.6
O3—C8—N2123.68 (15)C14—C13—H13A108.6
N2—C8—N1114.31 (15)C14—C13—H13B108.6
N3—C9—H9AA107.5N3—C14—C13116.65 (15)
N3—C9—H9AB107.5N3—C14—H14A105.8 (12)
N3—C9—H9BC108.8N3—C14—H14B105.3 (12)
N3—C9—H9BD108.8C13—C14—H14A110.4 (12)
N3—C9—C10A119.13 (15)C13—C14—H14B110.6 (11)
N3—C9—C10B113.9 (7)H14A—C14—H14B107.6 (16)
S1—N1—C8—O33.3 (2)C2—C3—C4—S1177.89 (13)
S1—N1—C8—N2177.23 (12)C2—C3—C4—C50.2 (3)
S1—C4—C5—C6177.05 (13)C3—C4—C5—C61.0 (3)
O1—S1—N1—C8172.43 (14)C4—S1—N1—C857.59 (16)
O1—S1—C4—C338.55 (16)C4—C5—C6—C11.2 (3)
O1—S1—C4—C5139.55 (14)C6—C1—C2—C30.3 (3)
O2—S1—N1—C859.07 (16)C7—C1—C2—C3178.55 (16)
O2—S1—C4—C3171.07 (13)C7—C1—C6—C5177.68 (16)
O2—S1—C4—C57.03 (16)C8—N2—N3—C9109.99 (17)
N1—S1—C4—C372.15 (15)C8—N2—N3—C14121.22 (16)
N1—S1—C4—C5109.74 (15)C9—N3—C14—C1363.6 (2)
N2—N3—C9—C10A74.0 (2)C9—C10A—C11—C1278.6 (2)
N2—N3—C9—C10B141.4 (3)C9—C10B—C11—C1277.7 (12)
N2—N3—C14—C1362.4 (2)C10A—C11—C12—C1323.5 (2)
N3—N2—C8—O3175.57 (15)C10B—C11—C12—C1342.9 (4)
N3—N2—C8—N15.0 (2)C11—C12—C13—C1449.7 (2)
N3—C9—C10A—C1173.9 (2)C12—C13—C14—N386.5 (2)
N3—C9—C10B—C1182.2 (12)C14—N3—C9—C10A51.7 (2)
C1—C2—C3—C40.5 (3)C14—N3—C9—C10B15.6 (4)
C2—C1—C6—C50.6 (3)
1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide (TZA_I_125) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.394 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.2586 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0748 (4) ÅCell parameters from 5366 reflections
c = 13.3249 (5) Åθ = 2.3–28.8°
α = 79.432 (3)°µ = 0.23 mm1
β = 87.442 (3)°T = 125 K
γ = 85.975 (3)°Block, colourless
V = 741.73 (5) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3037 independent reflections
Radiation source: Enhance (Mo) X-ray Source2585 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 1.6°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.894, Tmax = 1.000l = 1616
11961 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0337P)2 + 0.3459P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3037 reflectionsΔρmax = 0.40 e Å3
213 parametersΔρmin = 0.38 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.01918 (6)0.26706 (4)0.22345 (3)0.01862 (12)
O10.14089 (19)0.15310 (13)0.18063 (9)0.0250 (3)
O20.20835 (18)0.26633 (13)0.23096 (9)0.0246 (3)
O30.07315 (17)0.45398 (12)0.38331 (8)0.0202 (3)
N10.1130 (2)0.24858 (16)0.33886 (11)0.0201 (3)
H10.211 (3)0.191 (2)0.3536 (15)0.028 (6)*
N20.1595 (2)0.31515 (16)0.49372 (11)0.0217 (3)
H20.142 (3)0.379 (2)0.5331 (15)0.029 (5)*
N30.3205 (2)0.19704 (15)0.50985 (10)0.0204 (3)
C10.2010 (3)0.72212 (19)0.05164 (12)0.0195 (3)
C20.3549 (3)0.6050 (2)0.07675 (13)0.0225 (4)
H2A0.49720.62050.05710.027*
C30.3030 (3)0.46608 (19)0.13018 (13)0.0219 (4)
H30.40830.38880.14610.026*
C40.0908 (2)0.44445 (18)0.15951 (12)0.0170 (3)
C50.0663 (3)0.55888 (19)0.13637 (13)0.0215 (4)
H50.20810.54360.15720.026*
C60.0105 (3)0.69659 (19)0.08185 (13)0.0226 (4)
H60.11650.77330.06520.027*
C70.2622 (3)0.8732 (2)0.00399 (13)0.0265 (4)
H7A0.40330.86400.03440.040*
H7B0.26070.94150.04320.040*
H7C0.16160.91080.05640.040*
C80.0581 (2)0.34786 (18)0.40502 (12)0.0179 (3)
C90.5333 (3)0.2569 (2)0.51079 (13)0.0243 (4)
H9AA0.54650.33550.45120.029*0.927 (5)
H9AB0.64010.17700.50230.029*0.927 (5)
H9BC0.51460.35850.52430.029*0.073 (5)
H9BD0.60160.26170.44360.029*0.073 (5)
C10A0.5911 (3)0.3199 (2)0.60256 (14)0.0222 (5)0.927 (5)
H10A0.47280.38640.62020.027*0.927 (5)
H10B0.71470.37930.58460.027*0.927 (5)
C10B0.679 (3)0.165 (2)0.5886 (6)0.034 (8)*0.073 (5)
H10C0.82640.18360.56690.040*0.073 (5)
H10D0.65990.05980.59060.040*0.073 (5)
C110.6418 (3)0.1993 (2)0.69612 (13)0.0255 (4)
H11A0.72860.11800.67350.031*0.927 (5)
H11B0.72810.24220.74080.031*0.927 (5)
H11C0.62630.30750.69090.031*0.073 (5)
H11D0.76960.16410.73420.031*0.073 (5)
C120.4494 (3)0.1327 (2)0.75867 (13)0.0250 (4)
H12A0.48820.02820.78640.030*
H12B0.42250.18450.81600.030*
C130.2412 (3)0.13973 (19)0.70238 (12)0.0207 (4)
H13A0.13980.07950.74620.025*
H13B0.18150.24280.69040.024 (5)*
C140.2636 (3)0.0855 (2)0.60060 (13)0.0233 (4)
H14A0.371 (3)0.004 (2)0.6037 (13)0.022 (5)*
H14B0.129 (3)0.047 (2)0.5862 (14)0.025 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0234 (2)0.0156 (2)0.0170 (2)0.00040 (16)0.00456 (16)0.00297 (16)
O10.0360 (7)0.0189 (6)0.0213 (6)0.0036 (5)0.0061 (5)0.0074 (5)
O20.0242 (6)0.0219 (6)0.0273 (7)0.0048 (5)0.0049 (5)0.0012 (5)
O30.0228 (6)0.0182 (6)0.0189 (6)0.0034 (5)0.0020 (5)0.0027 (5)
N10.0253 (8)0.0169 (7)0.0173 (7)0.0046 (6)0.0058 (6)0.0025 (6)
N20.0286 (8)0.0187 (8)0.0180 (7)0.0062 (6)0.0041 (6)0.0064 (6)
N30.0234 (7)0.0185 (7)0.0188 (7)0.0037 (6)0.0051 (6)0.0030 (6)
C10.0243 (8)0.0214 (9)0.0137 (8)0.0030 (7)0.0029 (6)0.0047 (7)
C20.0170 (8)0.0271 (10)0.0239 (9)0.0032 (7)0.0018 (7)0.0059 (7)
C30.0192 (8)0.0224 (9)0.0239 (9)0.0044 (7)0.0030 (7)0.0047 (7)
C40.0213 (8)0.0169 (8)0.0128 (8)0.0002 (6)0.0033 (6)0.0029 (6)
C50.0170 (8)0.0238 (9)0.0224 (9)0.0002 (7)0.0011 (7)0.0012 (7)
C60.0217 (8)0.0207 (9)0.0233 (9)0.0042 (7)0.0025 (7)0.0005 (7)
C70.0291 (9)0.0247 (10)0.0250 (9)0.0058 (8)0.0025 (7)0.0005 (7)
C80.0202 (8)0.0158 (8)0.0168 (8)0.0032 (7)0.0020 (6)0.0004 (6)
C90.0254 (9)0.0251 (9)0.0211 (9)0.0006 (7)0.0002 (7)0.0012 (7)
C10A0.0191 (9)0.0216 (10)0.0264 (11)0.0035 (7)0.0013 (7)0.0054 (8)
C110.0197 (8)0.0339 (10)0.0237 (9)0.0004 (7)0.0050 (7)0.0071 (8)
C120.0250 (9)0.0303 (10)0.0184 (9)0.0030 (7)0.0022 (7)0.0027 (7)
C130.0205 (8)0.0192 (9)0.0206 (9)0.0015 (7)0.0001 (7)0.0012 (7)
C140.0282 (9)0.0167 (9)0.0253 (9)0.0034 (8)0.0060 (7)0.0029 (7)
Geometric parameters (Å, º) top
S1—O11.4291 (12)C9—H9AA0.9700
S1—O21.4235 (12)C9—H9AB0.9700
S1—N11.6461 (14)C9—H9BC0.9700
S1—C41.7556 (16)C9—H9BD0.9700
O3—C81.2222 (19)C9—C10A1.509 (2)
N1—H10.79 (2)C9—C10B1.503 (6)
N1—C81.388 (2)C10A—H10A0.9700
N2—H20.85 (2)C10A—H10B0.9700
N2—N31.4121 (19)C10A—C111.529 (3)
N2—C81.341 (2)C10B—H10C0.9700
N3—C91.474 (2)C10B—H10D0.9700
N3—C141.476 (2)C10B—C111.523 (6)
C1—C21.387 (2)C11—H11A0.9700
C1—C61.389 (2)C11—H11B0.9700
C1—C71.501 (2)C11—H11C0.9700
C2—H2A0.9300C11—H11D0.9700
C2—C31.382 (2)C11—C121.529 (2)
C3—H30.9300C12—H12A0.9700
C3—C41.384 (2)C12—H12B0.9700
C4—C51.381 (2)C12—C131.524 (2)
C5—H50.9300C13—H13A0.9700
C5—C61.384 (2)C13—H13B0.9700
C6—H60.9300C13—C141.523 (2)
C7—H7A0.9600C14—H14A0.958 (19)
C7—H7B0.9600C14—H14B0.976 (18)
C7—H7C0.9600
O1—S1—N1103.40 (7)H9AA—C9—H9AB107.1
O1—S1—C4109.34 (7)H9BC—C9—H9BD107.7
O2—S1—O1119.79 (7)C10A—C9—H9AA107.6
O2—S1—N1109.04 (7)C10A—C9—H9AB107.6
O2—S1—C4108.88 (7)C10B—C9—H9BC108.8
N1—S1—C4105.40 (7)C10B—C9—H9BD108.8
S1—N1—H1118.3 (15)C9—C10A—H10A108.9
C8—N1—S1123.78 (12)C9—C10A—H10B108.9
C8—N1—H1116.7 (15)C9—C10A—C11113.52 (15)
N3—N2—H2121.7 (14)H10A—C10A—H10B107.7
C8—N2—H2116.7 (14)C11—C10A—H10A108.9
C8—N2—N3120.38 (14)C11—C10A—H10B108.9
N2—N3—C9110.62 (13)C9—C10B—H10C108.7
N2—N3—C14110.04 (13)C9—C10B—H10D108.7
C9—N3—C14115.25 (13)C9—C10B—C11114.2 (4)
C2—C1—C6118.07 (15)H10C—C10B—H10D107.6
C2—C1—C7120.93 (15)C11—C10B—H10C108.7
C6—C1—C7120.98 (15)C11—C10B—H10D108.7
C1—C2—H2A119.0C10A—C11—H11A108.2
C3—C2—C1121.91 (15)C10A—C11—H11B108.2
C3—C2—H2A119.0C10B—C11—H11C107.9
C2—C3—H3120.7C10B—C11—H11D107.9
C2—C3—C4118.59 (16)C10B—C11—C12117.5 (10)
C4—C3—H3120.7H11A—C11—H11B107.4
C3—C4—S1119.48 (13)H11C—C11—H11D107.2
C5—C4—S1119.48 (12)C12—C11—C10A116.33 (14)
C5—C4—C3121.00 (15)C12—C11—H11A108.2
C4—C5—H5120.3C12—C11—H11B108.2
C4—C5—C6119.32 (15)C12—C11—H11C107.9
C6—C5—H5120.3C12—C11—H11D107.9
C1—C6—H6119.5C11—C12—H12A108.2
C5—C6—C1121.09 (16)C11—C12—H12B108.2
C5—C6—H6119.5H12A—C12—H12B107.3
C1—C7—H7A109.5C13—C12—C11116.50 (14)
C1—C7—H7B109.5C13—C12—H12A108.2
C1—C7—H7C109.5C13—C12—H12B108.2
H7A—C7—H7B109.5C12—C13—H13A108.6
H7A—C7—H7C109.5C12—C13—H13B108.6
H7B—C7—H7C109.5H13A—C13—H13B107.5
O3—C8—N1122.01 (15)C14—C13—C12114.83 (14)
O3—C8—N2123.97 (15)C14—C13—H13A108.6
N2—C8—N1114.02 (15)C14—C13—H13B108.6
N3—C9—H9AA107.6N3—C14—C13116.91 (14)
N3—C9—H9AB107.6N3—C14—H14A106.2 (11)
N3—C9—H9BC108.8N3—C14—H14B106.5 (11)
N3—C9—H9BD108.8C13—C14—H14A110.4 (11)
N3—C9—C10A118.75 (14)C13—C14—H14B109.5 (11)
N3—C9—C10B113.9 (10)H14A—C14—H14B106.8 (15)
S1—N1—C8—O33.3 (2)C2—C3—C4—S1177.74 (12)
S1—N1—C8—N2177.45 (11)C2—C3—C4—C50.2 (2)
S1—C4—C5—C6177.06 (12)C3—C4—C5—C60.8 (2)
O1—S1—N1—C8172.42 (13)C4—S1—N1—C857.66 (15)
O1—S1—C4—C338.35 (15)C4—C5—C6—C11.1 (2)
O1—S1—C4—C5139.59 (13)C6—C1—C2—C30.0 (2)
O2—S1—N1—C859.09 (15)C7—C1—C2—C3178.37 (15)
O2—S1—C4—C3170.91 (12)C7—C1—C6—C5177.67 (15)
O2—S1—C4—C57.03 (15)C8—N2—N3—C9109.40 (16)
N1—S1—C4—C372.23 (14)C8—N2—N3—C14122.11 (15)
N1—S1—C4—C5109.83 (14)C9—N3—C14—C1364.2 (2)
N2—N3—C9—C10A73.62 (19)C9—C10A—C11—C1279.85 (19)
N2—N3—C9—C10B141.4 (3)C9—C10B—C11—C1277.6 (17)
N2—N3—C14—C1361.73 (19)C10A—C11—C12—C1324.9 (2)
N3—N2—C8—O3175.31 (14)C10B—C11—C12—C1342.5 (4)
N3—N2—C8—N15.5 (2)C11—C12—C13—C1448.7 (2)
N3—C9—C10A—C1174.5 (2)C12—C13—C14—N386.64 (19)
N3—C9—C10B—C1182.3 (16)C14—N3—C9—C10A52.0 (2)
C1—C2—C3—C40.3 (2)C14—N3—C9—C10B15.8 (4)
C2—C1—C6—C50.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.85 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.400 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.2433 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0724 (4) ÅCell parameters from 5559 reflections
c = 13.3119 (5) Åθ = 2.3–29.0°
α = 79.359 (4)°µ = 0.23 mm1
β = 87.461 (3)°T = 100 K
γ = 85.933 (3)°Block, colourless
V = 738.80 (5) Å30.4 × 0.1 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3021 independent reflections
Radiation source: Enhance (Mo) X-ray Source2604 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 1.6°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.934, Tmax = 1.000l = 1616
11890 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.034P)2 + 0.3817P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3021 reflectionsΔρmax = 0.44 e Å3
208 parametersΔρmin = 0.40 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.01861 (6)0.26687 (4)0.22346 (3)0.01516 (12)
O10.14105 (19)0.15283 (13)0.18048 (9)0.0204 (3)
O20.20987 (18)0.26621 (13)0.23085 (9)0.0200 (3)
O30.07370 (17)0.45367 (12)0.38361 (8)0.0167 (3)
N10.1127 (2)0.24786 (16)0.33920 (10)0.0162 (3)
H10.213 (3)0.193 (2)0.3511 (14)0.019 (5)*
N20.1591 (2)0.31406 (16)0.49428 (11)0.0173 (3)
H20.143 (3)0.376 (2)0.5328 (15)0.020 (5)*
N30.3212 (2)0.19597 (15)0.51034 (10)0.0163 (3)
C10.2002 (3)0.72260 (18)0.05139 (12)0.0164 (3)
C20.3551 (3)0.60528 (19)0.07648 (12)0.0182 (4)
H2A0.49780.62080.05680.022*
C30.3031 (3)0.46589 (19)0.12991 (12)0.0183 (4)
H30.40860.38830.14560.022*
C40.0901 (2)0.44457 (18)0.15961 (11)0.0140 (3)
C50.0676 (3)0.55928 (19)0.13686 (12)0.0177 (4)
H50.20960.54410.15810.021*
C60.0119 (3)0.69707 (19)0.08208 (12)0.0184 (4)
H60.11820.77390.06550.022*
C70.2614 (3)0.87395 (19)0.00417 (13)0.0216 (4)
H7A0.40330.86500.03420.032*
H7B0.25880.94220.04310.032*
H7C0.16120.91140.05700.032*
C80.0576 (2)0.34693 (18)0.40537 (12)0.0145 (3)
C90.5343 (3)0.25590 (19)0.51034 (13)0.0192 (4)
H9A0.54720.33400.45030.023*
H9B0.64150.17580.50230.023*
C100.5917 (3)0.32049 (19)0.60253 (13)0.0209 (4)
H10A0.47220.38620.62020.025*
H10B0.71470.38070.58430.025*
C110.6442 (3)0.1997 (2)0.69586 (13)0.0202 (4)
H11A0.73230.24220.74010.024*
H11B0.72990.11810.67290.024*
C120.4515 (3)0.1338 (2)0.75942 (12)0.0199 (4)
H12A0.49070.02970.78830.024*
H12B0.42430.18710.81600.024*
C130.2424 (3)0.13928 (19)0.70317 (12)0.0169 (3)
H13A0.14150.07870.74730.020*
H13B0.18140.24210.69070.022 (5)*
C140.2657 (3)0.08411 (19)0.60146 (13)0.0184 (4)
H14A0.374 (3)0.002 (2)0.6061 (14)0.020 (5)*
H14B0.131 (3)0.0457 (19)0.5867 (13)0.015 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0187 (2)0.0129 (2)0.0140 (2)0.00021 (15)0.00386 (15)0.00245 (15)
O10.0284 (6)0.0163 (6)0.0177 (6)0.0021 (5)0.0038 (5)0.0066 (5)
O20.0189 (6)0.0183 (6)0.0226 (6)0.0039 (5)0.0036 (5)0.0013 (5)
O30.0179 (6)0.0156 (6)0.0159 (6)0.0024 (5)0.0008 (4)0.0024 (5)
N10.0187 (7)0.0148 (7)0.0145 (7)0.0041 (6)0.0045 (6)0.0024 (6)
N20.0224 (7)0.0149 (7)0.0153 (7)0.0049 (6)0.0032 (6)0.0062 (6)
N30.0177 (7)0.0150 (7)0.0157 (7)0.0032 (5)0.0037 (5)0.0026 (6)
C10.0205 (8)0.0181 (8)0.0115 (8)0.0033 (7)0.0025 (6)0.0041 (6)
C20.0147 (8)0.0217 (9)0.0185 (9)0.0024 (7)0.0007 (6)0.0045 (7)
C30.0158 (8)0.0197 (9)0.0190 (9)0.0042 (7)0.0027 (6)0.0044 (7)
C40.0184 (8)0.0140 (8)0.0101 (7)0.0003 (6)0.0020 (6)0.0029 (6)
C50.0142 (8)0.0200 (9)0.0180 (8)0.0003 (7)0.0003 (6)0.0014 (7)
C60.0173 (8)0.0167 (9)0.0195 (9)0.0046 (7)0.0023 (7)0.0007 (7)
C70.0247 (9)0.0193 (9)0.0202 (9)0.0049 (7)0.0023 (7)0.0005 (7)
C80.0152 (8)0.0138 (8)0.0140 (8)0.0037 (6)0.0025 (6)0.0010 (6)
C90.0194 (8)0.0193 (9)0.0178 (8)0.0002 (7)0.0009 (7)0.0013 (7)
C100.0181 (8)0.0210 (9)0.0243 (9)0.0029 (7)0.0017 (7)0.0060 (7)
C110.0154 (8)0.0271 (10)0.0190 (9)0.0003 (7)0.0037 (7)0.0065 (7)
C120.0201 (8)0.0240 (9)0.0147 (8)0.0024 (7)0.0014 (7)0.0023 (7)
C130.0161 (8)0.0156 (8)0.0173 (8)0.0010 (6)0.0013 (6)0.0008 (7)
C140.0211 (9)0.0143 (8)0.0197 (9)0.0019 (7)0.0049 (7)0.0013 (7)
Geometric parameters (Å, º) top
S1—O11.4317 (12)C6—H60.9300
S1—O21.4258 (12)C7—H7A0.9600
S1—N11.6481 (14)C7—H7B0.9600
S1—C41.7557 (16)C7—H7C0.9600
O3—C81.2242 (19)C9—H9A0.9700
N1—H10.78 (2)C9—H9B0.9700
N1—C81.387 (2)C9—C101.521 (2)
N2—H20.83 (2)C10—H10A0.9700
N2—N31.4139 (19)C10—H10B0.9700
N2—C81.342 (2)C10—C111.528 (2)
N3—C91.472 (2)C11—H11A0.9700
N3—C141.476 (2)C11—H11B0.9700
C1—C21.390 (2)C11—C121.532 (2)
C1—C61.391 (2)C12—H12A0.9700
C1—C71.501 (2)C12—H12B0.9700
C2—H2A0.9300C12—C131.526 (2)
C2—C31.384 (2)C13—H13A0.9700
C3—H30.9300C13—H13B0.9700
C3—C41.387 (2)C13—C141.526 (2)
C4—C51.382 (2)C14—H14A0.96 (2)
C5—H50.9300C14—H14B0.976 (17)
C5—C61.385 (2)
O1—S1—N1103.36 (7)O3—C8—N1122.14 (15)
O1—S1—C4109.38 (7)O3—C8—N2123.79 (15)
O2—S1—O1119.81 (7)N2—C8—N1114.06 (14)
O2—S1—N1109.07 (7)N3—C9—H9A107.7
O2—S1—C4108.81 (7)N3—C9—H9B107.7
N1—S1—C4105.43 (7)N3—C9—C10118.26 (13)
S1—N1—H1116.4 (14)H9A—C9—H9B107.1
C8—N1—S1123.71 (12)C10—C9—H9A107.7
C8—N1—H1118.0 (14)C10—C9—H9B107.7
N3—N2—H2121.3 (13)C9—C10—H10A109.0
C8—N2—H2117.0 (14)C9—C10—H10B109.0
C8—N2—N3120.31 (14)C9—C10—C11113.05 (14)
N2—N3—C9110.70 (12)H10A—C10—H10B107.8
N2—N3—C14110.19 (12)C11—C10—H10A109.0
C9—N3—C14115.29 (13)C11—C10—H10B109.0
C2—C1—C6118.10 (15)C10—C11—H11A108.3
C2—C1—C7120.87 (14)C10—C11—H11B108.3
C6—C1—C7121.00 (15)C10—C11—C12116.08 (14)
C1—C2—H2A119.1H11A—C11—H11B107.4
C3—C2—C1121.85 (15)C12—C11—H11A108.3
C3—C2—H2A119.1C12—C11—H11B108.3
C2—C3—H3120.8C11—C12—H12A108.2
C2—C3—C4118.50 (15)C11—C12—H12B108.2
C4—C3—H3120.8H12A—C12—H12B107.3
C3—C4—S1119.34 (13)C13—C12—C11116.41 (14)
C5—C4—S1119.49 (12)C13—C12—H12A108.2
C5—C4—C3121.14 (15)C13—C12—H12B108.2
C4—C5—H5120.4C12—C13—H13A108.6
C4—C5—C6119.26 (14)C12—C13—H13B108.6
C6—C5—H5120.4H13A—C13—H13B107.5
C1—C6—H6119.4C14—C13—C12114.79 (14)
C5—C6—C1121.14 (15)C14—C13—H13A108.6
C5—C6—H6119.4C14—C13—H13B108.6
C1—C7—H7A109.5N3—C14—C13116.73 (13)
C1—C7—H7B109.5N3—C14—H14A107.1 (11)
C1—C7—H7C109.5N3—C14—H14B105.8 (10)
H7A—C7—H7B109.5C13—C14—H14A109.6 (11)
H7A—C7—H7C109.5C13—C14—H14B109.6 (10)
H7B—C7—H7C109.5H14A—C14—H14B107.5 (14)
S1—N1—C8—O33.1 (2)C2—C1—C6—C50.6 (2)
S1—N1—C8—N2177.43 (11)C2—C3—C4—S1177.75 (12)
S1—C4—C5—C6176.85 (12)C2—C3—C4—C50.1 (2)
O1—S1—N1—C8172.36 (13)C3—C4—C5—C61.0 (2)
O1—S1—C4—C338.04 (15)C4—S1—N1—C857.57 (14)
O1—S1—C4—C5139.86 (13)C4—C5—C6—C11.2 (2)
O2—S1—N1—C859.12 (14)C6—C1—C2—C30.4 (2)
O2—S1—C4—C3170.60 (12)C7—C1—C2—C3178.37 (15)
O2—S1—C4—C57.29 (15)C7—C1—C6—C5177.44 (15)
N1—S1—C4—C372.53 (14)C8—N2—N3—C9108.76 (16)
N1—S1—C4—C5109.58 (13)C8—N2—N3—C14122.52 (15)
N2—N3—C9—C1073.30 (18)C9—N3—C14—C1364.96 (19)
N2—N3—C14—C1361.22 (18)C9—C10—C11—C1280.88 (18)
N3—N2—C8—O3174.91 (14)C10—C11—C12—C1326.0 (2)
N3—N2—C8—N15.7 (2)C11—C12—C13—C1448.0 (2)
N3—C9—C10—C1175.08 (19)C12—C13—C14—N386.73 (18)
C1—C2—C3—C40.6 (2)C14—N3—C9—C1052.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.83 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.325 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.4948 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0520 (4) ÅCell parameters from 4126 reflections
c = 13.4605 (6) Åθ = 3.8–25.7°
α = 82.467 (4)°µ = 0.22 mm1
β = 85.251 (4)°T = 295 K
γ = 85.836 (4)°Plate, colourless
V = 780.31 (6) Å30.45 × 0.3 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3189 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2335 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 3.4°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1111
Tmin = 0.949, Tmax = 1.000l = 1616
12592 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.051P)2 + 0.1546P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3189 reflectionsΔρmax = 0.20 e Å3
218 parametersΔρmin = 0.28 e Å3
3 restraints
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.25229 (8)0.97193 (5)0.39243 (4)0.03985 (18)
O30.0634 (2)0.67313 (16)0.41245 (11)0.0514 (4)
N10.2532 (3)0.83253 (19)0.48202 (13)0.0397 (4)
N30.2865 (3)0.64152 (19)0.64517 (12)0.0415 (4)
O10.3453 (2)1.08737 (15)0.43255 (11)0.0498 (4)
O20.0517 (2)1.00085 (17)0.35695 (12)0.0524 (4)
C80.1568 (3)0.7003 (2)0.48233 (15)0.0390 (5)
C40.4216 (3)0.9122 (2)0.29466 (14)0.0393 (5)
N20.1798 (3)0.6048 (2)0.56578 (14)0.0538 (5)
C50.6253 (3)0.8690 (2)0.31221 (16)0.0445 (5)
H50.67130.86670.37600.053*
C30.3526 (4)0.9165 (3)0.19988 (16)0.0513 (6)
H30.21540.94550.18850.062*
C10.6949 (4)0.8344 (3)0.13806 (17)0.0548 (6)
C60.7592 (4)0.8295 (3)0.23391 (17)0.0525 (6)
H60.89580.79900.24570.063*
C20.4894 (4)0.8774 (3)0.12254 (16)0.0591 (7)
H2A0.44320.87980.05870.071*
C140.4723 (4)0.5409 (3)0.65574 (19)0.0603 (6)
H14A0.57430.57650.60300.072*0.474 (7)
H14B0.43670.44390.64160.072*0.474 (7)
H14C0.54780.54080.59050.072*0.526 (7)
H14D0.43070.44030.67760.072*0.526 (7)
C90.1446 (4)0.6451 (3)0.73508 (17)0.0577 (6)
H9A0.13030.54380.76760.069*
H9B0.00930.68490.71520.069*
C100.2141 (5)0.7372 (3)0.8090 (2)0.0790 (9)
H10A0.25990.82980.77210.095*
H10B0.09460.76270.85310.095*
C70.8445 (5)0.7908 (4)0.0531 (2)0.0848 (9)
H7A0.79640.83670.00990.127*
H7B0.85330.68420.05460.127*
H7C0.97880.82390.06080.127*
C110.3805 (6)0.6716 (5)0.8724 (2)0.1079 (13)
H11C0.31370.63080.93630.129*0.526 (7)
H11D0.45780.75370.88580.129*0.526 (7)
H11A0.34260.57540.90700.129*0.474 (7)
H11B0.39890.73620.92260.129*0.474 (7)
C13A0.5765 (13)0.5165 (7)0.7509 (5)0.061 (2)0.474 (7)
H13A0.71760.47830.73620.073*0.474 (7)
H13B0.50750.43940.79560.073*0.474 (7)
C12A0.5835 (8)0.6521 (7)0.8073 (5)0.0622 (19)0.474 (7)
H12A0.60260.74100.75960.075*0.474 (7)
H12B0.69930.63800.84940.075*0.474 (7)
C13B0.6125 (10)0.5816 (9)0.7281 (4)0.073 (2)0.526 (7)
H13C0.63430.68720.71240.088*0.526 (7)
H13D0.74550.52770.71750.088*0.526 (7)
C12B0.5396 (11)0.5508 (7)0.8398 (4)0.099 (3)0.526 (7)
H12C0.47870.45480.85240.119*0.526 (7)
H12D0.65810.54570.87980.119*0.526 (7)
H10.315 (3)0.836 (2)0.5303 (17)0.048 (7)*
H20.126 (4)0.526 (3)0.5721 (17)0.054 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0459 (3)0.0346 (3)0.0401 (3)0.0066 (2)0.0070 (2)0.0037 (2)
O30.0651 (10)0.0462 (9)0.0468 (9)0.0152 (7)0.0187 (8)0.0051 (7)
N10.0475 (11)0.0400 (10)0.0334 (9)0.0123 (8)0.0079 (8)0.0033 (8)
N30.0452 (10)0.0445 (10)0.0364 (9)0.0100 (8)0.0082 (8)0.0034 (8)
O10.0656 (10)0.0352 (8)0.0511 (9)0.0123 (7)0.0077 (7)0.0079 (7)
O20.0481 (9)0.0511 (9)0.0585 (9)0.0006 (7)0.0126 (7)0.0050 (7)
C80.0428 (12)0.0376 (11)0.0380 (11)0.0089 (9)0.0035 (9)0.0066 (9)
C40.0482 (12)0.0348 (10)0.0361 (11)0.0143 (9)0.0052 (9)0.0009 (8)
N20.0762 (14)0.0423 (11)0.0468 (11)0.0270 (10)0.0222 (10)0.0039 (9)
C50.0476 (13)0.0494 (12)0.0386 (11)0.0118 (10)0.0056 (9)0.0063 (10)
C30.0544 (14)0.0590 (14)0.0413 (12)0.0121 (11)0.0106 (10)0.0005 (11)
C10.0640 (16)0.0559 (14)0.0453 (13)0.0211 (12)0.0087 (11)0.0083 (11)
C60.0481 (14)0.0561 (14)0.0551 (14)0.0114 (11)0.0010 (11)0.0107 (11)
C20.0739 (18)0.0721 (16)0.0335 (12)0.0182 (14)0.0054 (11)0.0065 (11)
C140.0594 (15)0.0566 (14)0.0660 (16)0.0037 (12)0.0081 (12)0.0145 (12)
C90.0477 (14)0.0713 (16)0.0505 (14)0.0030 (12)0.0005 (11)0.0032 (12)
C100.101 (2)0.0784 (19)0.0587 (16)0.0002 (17)0.0091 (16)0.0268 (15)
C70.092 (2)0.105 (2)0.0595 (17)0.0225 (18)0.0209 (16)0.0256 (16)
C110.117 (3)0.150 (4)0.068 (2)0.014 (3)0.024 (2)0.041 (2)
C13A0.058 (4)0.049 (4)0.074 (5)0.002 (3)0.018 (3)0.001 (3)
C12A0.064 (4)0.070 (4)0.058 (4)0.012 (3)0.014 (3)0.017 (3)
C13B0.053 (4)0.061 (5)0.107 (5)0.008 (3)0.031 (4)0.005 (4)
C12B0.150 (7)0.072 (5)0.079 (5)0.004 (5)0.060 (5)0.005 (4)
Geometric parameters (Å, º) top
S1—N11.6272 (18)C14—C13A1.481 (5)
S1—O11.4291 (14)C14—C13B1.484 (5)
S1—O21.4197 (15)C9—H9A0.9700
S1—C41.759 (2)C9—H9B0.9700
O3—C81.221 (2)C9—C101.495 (4)
N1—C81.390 (2)C10—H10A0.9700
N1—H10.79 (2)C10—H10B0.9700
N3—N21.408 (2)C10—C111.475 (5)
N3—C141.463 (3)C7—H7A0.9600
N3—C91.462 (3)C7—H7B0.9600
C8—N21.336 (3)C7—H7C0.9600
C4—C51.382 (3)C11—H11C0.9700
C4—C31.382 (3)C11—H11D0.9700
N2—H20.81 (2)C11—H11A0.9700
C5—H50.9300C11—H11B0.9700
C5—C61.377 (3)C11—C12A1.535 (6)
C3—H30.9300C11—C12B1.531 (6)
C3—C21.377 (3)C13A—H13A0.9700
C1—C61.383 (3)C13A—H13B0.9700
C1—C21.388 (3)C13A—C12A1.531 (5)
C1—C71.512 (3)C12A—H12A0.9700
C6—H60.9300C12A—H12B0.9700
C2—H2A0.9300C13B—H13C0.9700
C14—H14A0.9700C13B—H13D0.9700
C14—H14B0.9700C13B—C12B1.535 (6)
C14—H14C0.9700C12B—H12C0.9700
C14—H14D0.9700C12B—H12D0.9700
N1—S1—C4105.36 (9)H9A—C9—H9B107.7
O1—S1—N1104.51 (9)C10—C9—H9A108.9
O1—S1—C4108.23 (9)C10—C9—H9B108.9
O2—S1—N1110.37 (9)C9—C10—H10A107.9
O2—S1—O1119.15 (9)C9—C10—H10B107.9
O2—S1—C4108.37 (10)H10A—C10—H10B107.2
S1—N1—H1120.1 (16)C11—C10—C9117.7 (3)
C8—N1—S1125.60 (15)C11—C10—H10A107.9
C8—N1—H1114.3 (16)C11—C10—H10B107.9
N2—N3—C14108.75 (17)C1—C7—H7A109.5
N2—N3—C9109.58 (16)C1—C7—H7B109.5
C9—N3—C14116.07 (18)C1—C7—H7C109.5
O3—C8—N1123.25 (19)H7A—C7—H7B109.5
O3—C8—N2123.34 (18)H7A—C7—H7C109.5
N2—C8—N1113.39 (18)H7B—C7—H7C109.5
C5—C4—S1119.58 (15)C10—C11—H11C106.8
C3—C4—S1119.63 (18)C10—C11—H11D106.8
C3—C4—C5120.7 (2)C10—C11—H11A109.7
N3—N2—H2119.1 (17)C10—C11—H11B109.7
C8—N2—N3121.47 (17)C10—C11—C12A110.0 (3)
C8—N2—H2119.3 (17)C10—C11—C12B122.3 (3)
C4—C5—H5120.4H11C—C11—H11D106.6
C6—C5—C4119.1 (2)H11A—C11—H11B108.2
C6—C5—H5120.4C12A—C11—H11A109.7
C4—C3—H3120.4C12A—C11—H11B109.7
C2—C3—C4119.2 (2)C12B—C11—H11C106.8
C2—C3—H3120.4C12B—C11—H11D106.8
C6—C1—C2118.3 (2)C14—C13A—H13A108.1
C6—C1—C7120.6 (2)C14—C13A—H13B108.1
C2—C1—C7121.1 (2)C14—C13A—C12A116.8 (4)
C5—C6—C1121.4 (2)H13A—C13A—H13B107.3
C5—C6—H6119.3C12A—C13A—H13A108.1
C1—C6—H6119.3C12A—C13A—H13B108.1
C3—C2—C1121.2 (2)C11—C12A—H12A109.8
C3—C2—H2A119.4C11—C12A—H12B109.8
C1—C2—H2A119.4C13A—C12A—C11109.5 (5)
N3—C14—H14A107.1C13A—C12A—H12A109.8
N3—C14—H14B107.1C13A—C12A—H12B109.8
N3—C14—H14C108.8H12A—C12A—H12B108.2
N3—C14—H14D108.8C14—C13B—H13C108.2
N3—C14—C13A120.9 (3)C14—C13B—H13D108.2
N3—C14—C13B113.7 (4)C14—C13B—C12B116.3 (5)
H14A—C14—H14B106.8H13C—C13B—H13D107.4
H14C—C14—H14D107.7C12B—C13B—H13C108.2
C13A—C14—H14A107.1C12B—C13B—H13D108.2
C13A—C14—H14B107.1C11—C12B—C13B112.1 (5)
C13B—C14—H14C108.8C11—C12B—H12C109.2
C13B—C14—H14D108.8C11—C12B—H12D109.2
N3—C9—H9A108.9C13B—C12B—H12C109.2
N3—C9—H9B108.9C13B—C12B—H12D109.2
N3—C9—C10113.3 (2)H12C—C12B—H12D107.9
S1—N1—C8—O31.9 (3)N2—N3—C14—C13A159.2 (4)
S1—N1—C8—N2179.31 (16)N2—N3—C14—C13B172.2 (3)
S1—C4—C5—C6176.81 (16)N2—N3—C9—C10157.6 (2)
S1—C4—C3—C2176.45 (17)C5—C4—C3—C20.1 (3)
O3—C8—N2—N3179.2 (2)C3—C4—C5—C60.3 (3)
N1—S1—C4—C558.35 (17)C6—C1—C2—C30.9 (3)
N1—S1—C4—C3125.08 (17)C2—C1—C6—C51.3 (3)
N1—C8—N2—N32.1 (3)C14—N3—N2—C8115.4 (2)
N3—C14—C13A—C12A37.4 (8)C14—N3—C9—C1078.7 (3)
N3—C14—C13B—C12B73.0 (7)C14—C13A—C12A—C1183.8 (8)
N3—C9—C10—C1177.3 (3)C14—C13B—C12B—C1179.8 (9)
O1—S1—N1—C8172.19 (17)C9—N3—N2—C8116.8 (2)
O1—S1—C4—C552.99 (18)C9—N3—C14—C13A35.1 (5)
O1—S1—C4—C3123.58 (17)C9—N3—C14—C13B63.7 (4)
O2—S1—N1—C842.9 (2)C9—C10—C11—C12A66.6 (4)
O2—S1—C4—C5176.49 (15)C9—C10—C11—C12B25.6 (6)
O2—S1—C4—C36.94 (19)C10—C11—C12A—C13A76.4 (5)
C4—S1—N1—C873.84 (19)C10—C11—C12B—C13B40.8 (8)
C4—C5—C6—C11.0 (3)C7—C1—C6—C5179.9 (2)
C4—C3—C2—C10.3 (3)C7—C1—C2—C3179.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.79 (2)2.47 (2)3.105 (2)138 (2)
N2—H2···O3ii0.81 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.339 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.4468 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0141 (5) ÅCell parameters from 3177 reflections
c = 13.4850 (7) Åθ = 3.4–24.7°
α = 82.360 (4)°µ = 0.22 mm1
β = 85.368 (4)°T = 250 K
γ = 85.553 (4)°Plate, colourless
V = 772.38 (7) Å30.45 × 0.3 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3154 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2336 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 3.4°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1111
Tmin = 0.837, Tmax = 1.000l = 1616
11517 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.0565P)2 + 0.0711P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.23 e Å3
3154 reflectionsΔρmin = 0.41 e Å3
219 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.181 (10)
Primary atom site location: structure-invariant direct methods
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.25134 (8)0.97358 (6)0.39261 (4)0.0295 (2)
O30.0624 (2)0.67355 (17)0.41274 (11)0.0394 (4)
N10.2531 (3)0.8333 (2)0.48198 (14)0.0302 (4)
N30.2886 (3)0.6404 (2)0.64546 (13)0.0316 (4)
O10.3450 (2)1.08930 (16)0.43256 (12)0.0383 (4)
O20.0484 (2)1.00303 (17)0.35714 (12)0.0401 (4)
C80.1571 (3)0.7008 (2)0.48266 (16)0.0295 (5)
C40.4212 (3)0.9133 (2)0.29460 (15)0.0293 (5)
N20.1811 (3)0.6040 (2)0.56577 (14)0.0418 (5)
C50.6261 (3)0.8678 (2)0.31261 (17)0.0343 (5)
H50.67250.86410.37650.041*
C30.3512 (4)0.9198 (3)0.20008 (17)0.0384 (6)
H30.21320.95070.18860.046*
C10.6953 (4)0.8345 (3)0.13850 (17)0.0409 (6)
C60.7603 (4)0.8280 (3)0.23401 (18)0.0400 (6)
H60.89780.79610.24580.048*
C20.4885 (4)0.8797 (3)0.12263 (18)0.0456 (6)
H2A0.44180.88310.05880.055*
C140.4793 (4)0.5401 (3)0.6543 (2)0.0460 (6)
H14A0.58270.57950.60340.055*0.569 (7)
H14B0.44760.44320.63780.055*0.569 (7)
H14C0.55780.54530.58960.055*0.431 (7)
H14D0.44110.43770.67310.055*0.431 (7)
C90.1459 (4)0.6421 (3)0.73549 (18)0.0445 (6)
H9A0.13640.54030.76860.053*
H9B0.00800.67930.71590.053*
C100.2144 (5)0.7380 (3)0.8082 (2)0.0595 (8)
H10A0.25890.83060.77020.071*
H10B0.09360.76410.85170.071*
C70.8445 (5)0.7890 (4)0.0540 (2)0.0659 (9)
H7A0.80420.84340.00840.099*
H7B0.84080.68330.05150.099*
H7C0.98320.81130.06520.099*
C110.3837 (5)0.6742 (5)0.8724 (2)0.0808 (11)
H11C0.31820.63780.93750.097*0.431 (7)
H11D0.46480.75660.88230.097*0.431 (7)
H11A0.34490.57950.90950.097*0.569 (7)
H11B0.40350.74210.92040.097*0.569 (7)
C13A0.5791 (10)0.5139 (5)0.7522 (4)0.0450 (16)0.569 (7)
H13A0.72040.47170.74000.054*0.569 (7)
H13B0.50420.43870.79620.054*0.569 (7)
C12A0.5889 (6)0.6491 (6)0.8081 (4)0.0489 (16)0.569 (7)
H12A0.61200.73770.76030.059*0.569 (7)
H12B0.70470.63260.85090.059*0.569 (7)
C13B0.6147 (11)0.5805 (10)0.7306 (4)0.055 (2)0.431 (7)
H13C0.63450.68700.71620.066*0.431 (7)
H13D0.75050.52780.72130.066*0.431 (7)
C12B0.5390 (12)0.5476 (7)0.8409 (5)0.077 (3)0.431 (7)
H12C0.65740.53750.88200.092*0.431 (7)
H12D0.47210.45350.85190.092*0.431 (7)
H10.311 (3)0.838 (2)0.5275 (17)0.025 (6)*
H20.124 (4)0.527 (3)0.5730 (19)0.044 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0345 (3)0.0254 (3)0.0295 (3)0.0047 (2)0.0048 (2)0.0032 (2)
O30.0494 (10)0.0357 (9)0.0363 (9)0.0122 (8)0.0140 (8)0.0049 (7)
N10.0364 (10)0.0323 (10)0.0237 (10)0.0109 (8)0.0058 (8)0.0033 (8)
N30.0344 (10)0.0352 (10)0.0267 (10)0.0092 (8)0.0059 (8)0.0034 (8)
O10.0512 (9)0.0266 (8)0.0393 (9)0.0096 (7)0.0065 (7)0.0060 (7)
O20.0367 (9)0.0388 (9)0.0451 (10)0.0021 (7)0.0106 (7)0.0042 (7)
C80.0318 (11)0.0283 (11)0.0296 (12)0.0060 (9)0.0020 (9)0.0057 (9)
C40.0355 (11)0.0267 (11)0.0258 (11)0.0089 (9)0.0038 (9)0.0008 (9)
N20.0599 (13)0.0319 (11)0.0371 (12)0.0222 (10)0.0168 (10)0.0023 (9)
C50.0376 (12)0.0373 (12)0.0295 (12)0.0103 (10)0.0033 (10)0.0044 (10)
C30.0402 (13)0.0433 (14)0.0320 (13)0.0095 (11)0.0075 (10)0.0006 (10)
C10.0489 (14)0.0399 (14)0.0346 (13)0.0146 (12)0.0058 (11)0.0053 (10)
C60.0349 (12)0.0430 (14)0.0432 (14)0.0085 (11)0.0005 (10)0.0080 (11)
C20.0597 (16)0.0534 (16)0.0251 (12)0.0133 (13)0.0051 (11)0.0037 (11)
C140.0464 (14)0.0416 (14)0.0515 (16)0.0026 (12)0.0075 (12)0.0120 (12)
C90.0367 (13)0.0562 (16)0.0378 (14)0.0034 (12)0.0006 (10)0.0026 (12)
C100.0760 (19)0.0582 (18)0.0440 (16)0.0001 (15)0.0111 (14)0.0172 (14)
C70.0738 (19)0.079 (2)0.0450 (17)0.0130 (17)0.0166 (15)0.0174 (15)
C110.088 (2)0.111 (3)0.052 (2)0.008 (2)0.0177 (17)0.033 (2)
C13A0.043 (3)0.035 (3)0.057 (4)0.001 (3)0.014 (3)0.000 (2)
C12A0.046 (3)0.056 (4)0.049 (3)0.007 (2)0.010 (2)0.016 (3)
C13B0.036 (4)0.041 (5)0.085 (6)0.003 (4)0.025 (4)0.010 (4)
C12B0.119 (7)0.051 (5)0.063 (5)0.002 (5)0.052 (5)0.005 (4)
Geometric parameters (Å, º) top
S1—N11.6266 (19)C14—C13A1.498 (4)
S1—O11.4290 (14)C14—C13B1.499 (5)
S1—O21.4226 (16)C9—H9A0.9700
S1—C41.762 (2)C9—H9B0.9700
O3—C81.224 (2)C9—C101.502 (4)
N1—C81.386 (3)C10—H10A0.9700
N1—H10.75 (2)C10—H10B0.9700
N3—N21.411 (2)C10—C111.482 (5)
N3—C141.472 (3)C7—H7A0.9600
N3—C91.464 (3)C7—H7B0.9600
C8—N21.337 (3)C7—H7C0.9600
C4—C51.383 (3)C11—H11C0.9700
C4—C31.379 (3)C11—H11D0.9700
N2—H20.80 (3)C11—H11A0.9700
C5—H50.9300C11—H11B0.9700
C5—C61.381 (3)C11—C12A1.541 (5)
C3—H30.9300C11—C12B1.539 (6)
C3—C21.381 (3)C13A—H13A0.9700
C1—C61.379 (3)C13A—H13B0.9700
C1—C21.389 (3)C13A—C12A1.524 (5)
C1—C71.509 (3)C12A—H12A0.9700
C6—H60.9300C12A—H12B0.9700
C2—H2A0.9300C13B—H13C0.9700
C14—H14A0.9700C13B—H13D0.9700
C14—H14B0.9700C13B—C12B1.526 (6)
C14—H14C0.9700C12B—H12C0.9700
C14—H14D0.9700C12B—H12D0.9700
N1—S1—C4105.39 (10)H9A—C9—H9B107.8
O1—S1—N1104.58 (9)C10—C9—H9A109.1
O1—S1—C4108.36 (9)C10—C9—H9B109.1
O2—S1—N1110.32 (9)C9—C10—H10A107.9
O2—S1—O1119.18 (10)C9—C10—H10B107.9
O2—S1—C4108.16 (10)H10A—C10—H10B107.2
S1—N1—H1118.9 (17)C11—C10—C9117.5 (3)
C8—N1—S1125.85 (16)C11—C10—H10A107.9
C8—N1—H1115.2 (17)C11—C10—H10B107.9
N2—N3—C14108.44 (18)C1—C7—H7A109.5
N2—N3—C9109.61 (16)C1—C7—H7B109.5
C9—N3—C14116.68 (19)C1—C7—H7C109.5
O3—C8—N1123.1 (2)H7A—C7—H7B109.5
O3—C8—N2123.05 (18)H7A—C7—H7C109.5
N2—C8—N1113.84 (18)H7B—C7—H7C109.5
C5—C4—S1119.29 (16)C10—C11—H11C107.1
C3—C4—S1119.61 (18)C10—C11—H11D107.1
C3—C4—C5121.0 (2)C10—C11—H11A109.5
N3—N2—H2119.0 (18)C10—C11—H11B109.5
C8—N2—N3121.39 (18)C10—C11—C12A110.5 (3)
C8—N2—H2119.4 (18)C10—C11—C12B121.0 (3)
C4—C5—H5120.6H11C—C11—H11D106.8
C6—C5—C4118.8 (2)H11A—C11—H11B108.1
C6—C5—H5120.6C12A—C11—H11A109.5
C4—C3—H3120.4C12A—C11—H11B109.5
C4—C3—C2119.2 (2)C12B—C11—H11C107.1
C2—C3—H3120.4C12B—C11—H11D107.1
C6—C1—C2118.5 (2)C14—C13A—H13A108.0
C6—C1—C7120.6 (2)C14—C13A—H13B108.0
C2—C1—C7120.9 (2)C14—C13A—C12A117.2 (4)
C5—C6—H6119.2H13A—C13A—H13B107.2
C1—C6—C5121.6 (2)C12A—C13A—H13A108.0
C1—C6—H6119.2C12A—C13A—H13B108.0
C3—C2—C1121.0 (2)C11—C12A—H12A109.6
C3—C2—H2A119.5C11—C12A—H12B109.6
C1—C2—H2A119.5C13A—C12A—C11110.1 (4)
N3—C14—H14A107.6C13A—C12A—H12A109.6
N3—C14—H14B107.6C13A—C12A—H12B109.6
N3—C14—H14C109.2H12A—C12A—H12B108.1
N3—C14—H14D109.2C14—C13B—H13C107.9
N3—C14—C13A119.1 (3)C14—C13B—H13D107.9
N3—C14—C13B112.2 (4)C14—C13B—C12B117.6 (5)
H14A—C14—H14B107.0H13C—C13B—H13D107.2
H14C—C14—H14D107.9C12B—C13B—H13C107.9
C13A—C14—H14A107.6C12B—C13B—H13D107.9
C13A—C14—H14B107.6C11—C12B—H12C109.5
C13B—C14—H14C109.2C11—C12B—H12D109.5
C13B—C14—H14D109.2C13B—C12B—C11110.8 (6)
N3—C9—H9A109.1C13B—C12B—H12C109.5
N3—C9—H9B109.1C13B—C12B—H12D109.5
N3—C9—C10112.70 (19)H12C—C12B—H12D108.1
S1—N1—C8—O31.9 (3)N2—N3—C14—C13A157.5 (3)
S1—N1—C8—N2179.47 (17)N2—N3—C14—C13B174.3 (3)
S1—C4—C5—C6176.80 (16)N2—N3—C9—C10156.1 (2)
S1—C4—C3—C2176.63 (17)C5—C4—C3—C20.1 (3)
O3—C8—N2—N3179.0 (2)C3—C4—C5—C60.3 (3)
N1—S1—C4—C557.69 (18)C6—C1—C2—C31.0 (3)
N1—S1—C4—C3125.74 (17)C2—C1—C6—C51.2 (3)
N1—C8—N2—N32.3 (3)C14—N3—N2—C8114.4 (2)
N3—C14—C13A—C12A41.1 (6)C14—N3—C9—C1080.2 (3)
N3—C14—C13B—C12B71.6 (7)C14—C13A—C12A—C1184.9 (6)
N3—C9—C10—C1178.5 (3)C14—C13B—C12B—C1183.1 (9)
O1—S1—N1—C8172.25 (18)C9—N3—N2—C8117.2 (2)
O1—S1—C4—C553.81 (18)C9—N3—C14—C13A33.2 (4)
O1—S1—C4—C3122.77 (17)C9—N3—C14—C13B61.4 (4)
O2—S1—N1—C842.9 (2)C9—C10—C11—C12A65.1 (4)
O2—S1—C4—C5175.68 (15)C9—C10—C11—C12B23.2 (6)
O2—S1—C4—C37.7 (2)C10—C11—C12A—C13A74.0 (5)
C4—S1—N1—C873.6 (2)C10—C11—C12B—C13B44.8 (7)
C4—C5—C6—C10.8 (3)C7—C1—C6—C5179.4 (2)
C4—C3—C2—C10.5 (3)C7—C1—C2—C3179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.75 (2)2.48 (2)3.083 (2)139 (2)
N2—H2···O3ii0.80 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.352 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.3939 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9809 (4) ÅCell parameters from 3525 reflections
c = 13.5213 (7) Åθ = 3.5–28.1°
α = 82.129 (4)°µ = 0.23 mm1
β = 85.602 (4)°T = 200 K
γ = 85.341 (4)°Plate, colourless
V = 764.89 (6) Å30.45 × 0.3 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3115 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2445 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 3.5°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1111
Tmin = 0.805, Tmax = 1.000l = 1616
11396 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.051P)2 + 0.2748P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.31 e Å3
3115 reflectionsΔρmin = 0.39 e Å3
219 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.204 (10)
Primary atom site location: structure-invariant direct methods
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.25003 (8)0.97551 (5)0.39271 (4)0.02195 (18)
O30.0614 (2)0.67424 (16)0.41253 (11)0.0293 (4)
N10.2539 (3)0.83399 (19)0.48239 (13)0.0230 (4)
N30.2901 (3)0.63872 (19)0.64548 (12)0.0239 (4)
O10.3451 (2)1.09162 (15)0.43245 (11)0.0284 (4)
O20.0444 (2)1.00584 (16)0.35743 (11)0.0298 (4)
C80.1571 (3)0.7010 (2)0.48257 (15)0.0230 (4)
C40.4199 (3)0.9149 (2)0.29486 (14)0.0219 (4)
N20.1829 (3)0.6027 (2)0.56549 (14)0.0317 (5)
C50.6271 (3)0.8667 (2)0.31273 (16)0.0259 (5)
H50.67460.86160.37650.031*
C30.3473 (3)0.9234 (2)0.20016 (15)0.0279 (5)
H30.20830.95570.18880.033*
C10.6940 (3)0.8350 (2)0.13837 (16)0.0310 (5)
C60.7616 (3)0.8264 (2)0.23425 (17)0.0302 (5)
H60.90010.79280.24590.036*
C20.4856 (4)0.8829 (3)0.12266 (16)0.0329 (5)
H2A0.43800.88780.05890.039*
C140.4860 (4)0.5399 (3)0.65347 (18)0.0342 (5)
H14A0.59050.58340.60450.041*0.725 (7)
H14B0.45850.44340.63440.041*0.725 (7)
H14C0.56760.55060.58970.041*0.275 (7)
H14D0.45130.43570.66890.041*0.275 (7)
C90.1465 (3)0.6377 (3)0.73567 (16)0.0328 (5)
H9A0.14320.53530.76940.039*
H9B0.00560.67080.71610.039*
C100.2100 (4)0.7378 (3)0.80741 (18)0.0420 (6)
H10A0.24870.83190.76890.050*
H10B0.08760.76090.85110.050*
C70.8432 (4)0.7892 (3)0.0541 (2)0.0498 (7)
H7A0.79990.84250.00830.075*
H7B0.84170.68270.05270.075*
H7C0.98280.81330.06440.075*
C110.3866 (5)0.6779 (4)0.8716 (2)0.0527 (7)
H11C0.32550.64890.93870.063*0.275 (7)
H11D0.47300.76070.87500.063*0.275 (7)
H11A0.34840.58540.91250.063*0.725 (7)
H11B0.40840.75040.91610.063*0.725 (7)
C13A0.5821 (7)0.5103 (4)0.7531 (3)0.0337 (10)0.725 (7)
H13A0.72390.46520.74280.040*0.725 (7)
H13B0.50250.43630.79600.040*0.725 (7)
C12A0.5932 (5)0.6462 (4)0.8090 (3)0.0385 (11)0.725 (7)
H12A0.62100.73420.76110.046*0.725 (7)
H12B0.70850.62730.85270.046*0.725 (7)
C13B0.6160 (14)0.5780 (14)0.7336 (5)0.040 (3)0.275 (7)
H13C0.63630.68500.72020.048*0.275 (7)
H13D0.75350.52510.72610.048*0.275 (7)
C12B0.5347 (15)0.5439 (9)0.8431 (7)0.058 (4)0.275 (7)
H12C0.65200.52790.88570.070*0.275 (7)
H12D0.45950.45290.85240.070*0.275 (7)
H10.310 (4)0.843 (3)0.5265 (18)0.021 (6)*
H20.124 (4)0.521 (3)0.5725 (18)0.032 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0257 (3)0.0191 (3)0.0214 (3)0.00313 (19)0.00344 (19)0.00231 (19)
O30.0365 (9)0.0270 (8)0.0266 (8)0.0077 (7)0.0107 (7)0.0042 (6)
N10.0287 (10)0.0239 (9)0.0182 (9)0.0075 (7)0.0051 (8)0.0036 (7)
N30.0272 (9)0.0264 (9)0.0191 (9)0.0062 (7)0.0045 (7)0.0029 (7)
O10.0380 (8)0.0200 (7)0.0286 (8)0.0064 (6)0.0042 (6)0.0044 (6)
O20.0283 (8)0.0295 (8)0.0315 (8)0.0018 (6)0.0067 (6)0.0036 (6)
C80.0241 (10)0.0224 (10)0.0232 (10)0.0038 (8)0.0005 (8)0.0047 (8)
C40.0270 (10)0.0196 (10)0.0193 (10)0.0070 (8)0.0013 (8)0.0004 (8)
N20.0458 (12)0.0232 (10)0.0288 (10)0.0159 (9)0.0128 (8)0.0004 (8)
C50.0285 (11)0.0268 (11)0.0233 (11)0.0060 (9)0.0033 (8)0.0034 (8)
C30.0309 (11)0.0287 (11)0.0239 (11)0.0041 (9)0.0063 (9)0.0009 (9)
C10.0367 (12)0.0303 (12)0.0265 (12)0.0116 (10)0.0053 (9)0.0040 (9)
C60.0271 (11)0.0317 (12)0.0321 (12)0.0058 (9)0.0008 (9)0.0049 (9)
C20.0447 (14)0.0357 (12)0.0197 (11)0.0102 (11)0.0040 (9)0.0030 (9)
C140.0357 (12)0.0311 (12)0.0366 (13)0.0011 (10)0.0036 (10)0.0084 (10)
C90.0275 (11)0.0419 (13)0.0270 (12)0.0031 (10)0.0003 (9)0.0019 (10)
C100.0522 (15)0.0408 (14)0.0323 (13)0.0016 (12)0.0072 (11)0.0111 (11)
C70.0543 (16)0.0620 (18)0.0334 (14)0.0087 (14)0.0125 (12)0.0126 (13)
C110.0591 (17)0.0666 (19)0.0380 (15)0.0055 (15)0.0086 (13)0.0231 (14)
C13A0.031 (2)0.027 (2)0.044 (2)0.0008 (17)0.0090 (16)0.0023 (16)
C12A0.0355 (19)0.044 (2)0.039 (2)0.0081 (16)0.0081 (15)0.0097 (17)
C13B0.029 (5)0.030 (6)0.060 (7)0.005 (5)0.021 (5)0.007 (5)
C12B0.080 (8)0.046 (7)0.052 (7)0.009 (6)0.037 (6)0.002 (5)
Geometric parameters (Å, º) top
S1—N11.6321 (18)C14—C13A1.506 (4)
S1—O11.4324 (14)C14—C13B1.506 (5)
S1—O21.4260 (15)C9—H9A0.9700
S1—C41.763 (2)C9—H9B0.9700
O3—C81.227 (2)C9—C101.508 (3)
N1—C81.388 (2)C10—H10A0.9700
N1—H10.74 (2)C10—H10B0.9700
N3—N21.411 (2)C10—C111.497 (4)
N3—C141.477 (3)C7—H7A0.9600
N3—C91.469 (3)C7—H7B0.9600
C8—N21.341 (3)C7—H7C0.9600
C4—C51.388 (3)C11—H11C0.9700
C4—C31.385 (3)C11—H11D0.9700
N2—H20.84 (2)C11—H11A0.9700
C5—H50.9300C11—H11B0.9700
C5—C61.383 (3)C11—C12A1.541 (4)
C3—H30.9300C11—C12B1.543 (6)
C3—C21.387 (3)C13A—H13A0.9700
C1—C61.388 (3)C13A—H13B0.9700
C1—C21.389 (3)C13A—C12A1.530 (4)
C1—C71.508 (3)C12A—H12A0.9700
C6—H60.9300C12A—H12B0.9700
C2—H2A0.9300C13B—H13C0.9700
C14—H14A0.9700C13B—H13D0.9700
C14—H14B0.9700C13B—C12B1.530 (6)
C14—H14C0.9700C12B—H12C0.9700
C14—H14D0.9700C12B—H12D0.9700
N1—S1—C4105.32 (9)H9A—C9—H9B107.8
O1—S1—N1104.43 (9)C10—C9—H9A109.1
O1—S1—C4108.46 (9)C10—C9—H9B109.1
O2—S1—N1110.52 (9)C9—C10—H10A108.0
O2—S1—O1119.11 (9)C9—C10—H10B108.0
O2—S1—C4108.16 (9)H10A—C10—H10B107.3
S1—N1—H1116.5 (18)C11—C10—C9117.1 (2)
C8—N1—S1125.34 (15)C11—C10—H10A108.0
C8—N1—H1118.1 (18)C11—C10—H10B108.0
N2—N3—C14108.30 (16)C1—C7—H7A109.5
N2—N3—C9109.80 (16)C1—C7—H7B109.5
C9—N3—C14116.96 (17)C1—C7—H7C109.5
O3—C8—N1123.29 (19)H7A—C7—H7B109.5
O3—C8—N2123.02 (18)H7A—C7—H7C109.5
N2—C8—N1113.67 (17)H7B—C7—H7C109.5
C5—C4—S1119.46 (15)C10—C11—H11C107.4
C3—C4—S1119.37 (16)C10—C11—H11D107.4
C3—C4—C5121.1 (2)C10—C11—H11A109.2
N3—N2—H2118.8 (16)C10—C11—H11B109.2
C8—N2—N3121.41 (17)C10—C11—C12A112.1 (2)
C8—N2—H2119.5 (16)C10—C11—C12B119.7 (4)
C4—C5—H5120.5H11C—C11—H11D106.9
C6—C5—C4119.0 (2)H11A—C11—H11B107.9
C6—C5—H5120.5C12A—C11—H11A109.2
C4—C3—H3120.6C12A—C11—H11B109.2
C4—C3—C2118.8 (2)C12B—C11—H11C107.4
C2—C3—H3120.6C12B—C11—H11D107.4
C6—C1—C2118.6 (2)C14—C13A—H13A108.1
C6—C1—C7120.3 (2)C14—C13A—H13B108.1
C2—C1—C7121.1 (2)C14—C13A—C12A116.8 (3)
C5—C6—C1121.3 (2)H13A—C13A—H13B107.3
C5—C6—H6119.4C12A—C13A—H13A108.1
C1—C6—H6119.4C12A—C13A—H13B108.1
C3—C2—C1121.3 (2)C11—C12A—H12A109.3
C3—C2—H2A119.4C11—C12A—H12B109.3
C1—C2—H2A119.4C13A—C12A—C11111.5 (3)
N3—C14—H14A107.8C13A—C12A—H12A109.3
N3—C14—H14B107.8C13A—C12A—H12B109.3
N3—C14—H14C109.3H12A—C12A—H12B108.0
N3—C14—H14D109.3C14—C13B—H13C107.6
N3—C14—C13A118.1 (2)C14—C13B—H13D107.6
N3—C14—C13B111.4 (5)C14—C13B—C12B118.7 (7)
H14A—C14—H14B107.1H13C—C13B—H13D107.1
H14C—C14—H14D108.0C12B—C13B—H13C107.6
C13A—C14—H14A107.8C12B—C13B—H13D107.6
C13A—C14—H14B107.8C11—C12B—H12C109.9
C13B—C14—H14C109.3C11—C12B—H12D109.9
C13B—C14—H14D109.3C13B—C12B—C11109.1 (7)
N3—C9—H9A109.1C13B—C12B—H12C109.9
N3—C9—H9B109.1C13B—C12B—H12D109.9
N3—C9—C10112.65 (17)H12C—C12B—H12D108.3
S1—N1—C8—O32.0 (3)N2—N3—C14—C13A155.8 (2)
S1—N1—C8—N2179.65 (16)N2—N3—C14—C13B176.6 (4)
S1—C4—C5—C6176.87 (15)N2—N3—C9—C10154.20 (19)
S1—C4—C3—C2176.63 (15)C5—C4—C3—C20.0 (3)
O3—C8—N2—N3178.61 (19)C3—C4—C5—C60.2 (3)
N1—S1—C4—C556.79 (17)C6—C1—C2—C30.9 (3)
N1—S1—C4—C3126.50 (16)C2—C1—C6—C51.1 (3)
N1—C8—N2—N33.1 (3)C14—N3—N2—C8113.7 (2)
N3—C14—C13A—C12A44.3 (4)C14—N3—C9—C1081.9 (2)
N3—C14—C13B—C12B69.2 (9)C14—C13A—C12A—C1185.2 (4)
N3—C9—C10—C1178.3 (3)C14—C13B—C12B—C1186.3 (11)
O1—S1—N1—C8172.44 (17)C9—N3—N2—C8117.5 (2)
O1—S1—C4—C554.55 (17)C9—N3—C14—C13A31.1 (3)
O1—S1—C4—C3122.17 (16)C9—N3—C14—C13B58.8 (4)
O2—S1—N1—C843.2 (2)C9—C10—C11—C12A61.2 (3)
O2—S1—C4—C5174.97 (14)C9—C10—C11—C12B17.3 (6)
O2—S1—C4—C38.31 (19)C10—C11—C12A—C13A70.4 (4)
C4—S1—N1—C873.39 (18)C10—C11—C12B—C13B51.2 (8)
C4—C5—C6—C10.8 (3)C7—C1—C6—C5179.5 (2)
C4—C3—C2—C10.3 (3)C7—C1—C2—C3179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.74 (2)2.45 (2)3.048 (2)140 (2)
N2—H2···O3ii0.84 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.367 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.3358 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9455 (11) ÅCell parameters from 2355 reflections
c = 13.5482 (15) Åθ = 3.5–27.8°
α = 81.976 (10)°µ = 0.23 mm1
β = 85.919 (10)°T = 150 K
γ = 85.273 (10)°Plate, colourless
V = 756.38 (15) Å30.45 × 0.3 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3073 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2345 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 3.5°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1111
Tmin = 0.949, Tmax = 1.000l = 1616
10897 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0527P)2 + 0.3381P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.127(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.31 e Å3
3073 reflectionsΔρmin = 0.47 e Å3
209 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.122 (7)
Primary atom site location: structure-invariant direct methods
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.24890 (9)0.97737 (6)0.39267 (4)0.0186 (2)
O30.0600 (3)0.67520 (18)0.41208 (13)0.0238 (4)
N10.2543 (3)0.8355 (2)0.48205 (16)0.0193 (5)
N30.2923 (3)0.6364 (2)0.64536 (15)0.0201 (5)
O10.3453 (3)1.09391 (18)0.43196 (13)0.0235 (4)
O20.0407 (3)1.00828 (18)0.35765 (13)0.0238 (4)
C80.1574 (4)0.7010 (3)0.48249 (18)0.0187 (5)
C40.4182 (4)0.9163 (2)0.29485 (18)0.0184 (5)
N20.1842 (4)0.6016 (2)0.56488 (16)0.0254 (5)
C50.6273 (4)0.8658 (3)0.31301 (19)0.0215 (5)
H50.67610.85940.37670.026*
C30.3439 (4)0.9271 (3)0.20033 (18)0.0223 (6)
H30.20400.96150.18900.027*
C10.6921 (4)0.8355 (3)0.13836 (19)0.0250 (6)
C60.7612 (4)0.8253 (3)0.23417 (19)0.0242 (6)
H60.90080.79030.24580.029*
C20.4824 (4)0.8856 (3)0.12238 (19)0.0253 (6)
H2A0.43350.89160.05870.030*
C140.4928 (4)0.5390 (3)0.6529 (2)0.0257 (6)
H14A0.59820.58560.60570.031*0.904 (7)
H14B0.46880.44260.63210.031*0.904 (7)
H14C0.57750.55360.59030.031*0.096 (7)
H14D0.46190.43340.66660.031*0.096 (7)
C90.1465 (4)0.6327 (3)0.73527 (19)0.0253 (6)
H9A0.14750.52980.76930.030*
H9B0.00350.66300.71540.030*
C100.2061 (4)0.7360 (3)0.8070 (2)0.0301 (6)
H10A0.23960.83180.76850.036*
H10B0.08250.75600.85100.036*
C70.8416 (5)0.7887 (3)0.0541 (2)0.0369 (7)
H7A0.79040.83540.00870.055*
H7B0.84900.68060.05660.055*
H7C0.98040.82030.06100.055*
C110.3899 (5)0.6793 (3)0.8710 (2)0.0356 (7)
H11C0.33390.65660.93950.043*0.096 (7)
H11D0.48220.76110.86880.043*0.096 (7)
H11A0.35240.58880.91470.043*0.904 (7)
H11B0.41330.75540.91270.043*0.904 (7)
C13A0.5849 (5)0.5079 (4)0.7538 (2)0.0274 (8)0.904 (7)
H13A0.72740.46090.74530.033*0.904 (7)
H13B0.50150.43450.79550.033*0.904 (7)
C12A0.5968 (5)0.6431 (3)0.8104 (2)0.0310 (9)0.904 (7)
H12A0.62910.73110.76310.037*0.904 (7)
H12B0.71160.62170.85520.037*0.904 (7)
C13B0.614 (4)0.580 (4)0.7359 (12)0.026 (8)*0.096 (7)
H13C0.62670.68820.72420.031*0.096 (7)
H13D0.75600.53140.73040.031*0.096 (7)
C12B0.525 (4)0.5397 (17)0.8434 (17)0.033 (9)*0.096 (7)
H12C0.64030.51420.88790.040*0.096 (7)
H12D0.43970.45360.84860.040*0.096 (7)
H10.311 (5)0.841 (3)0.529 (2)0.029 (8)*
H20.129 (4)0.521 (3)0.571 (2)0.030 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0228 (3)0.0136 (3)0.0200 (3)0.0030 (2)0.0025 (2)0.0029 (2)
O30.0294 (10)0.0205 (9)0.0237 (10)0.0070 (8)0.0064 (8)0.0047 (7)
N10.0246 (11)0.0171 (11)0.0183 (11)0.0075 (9)0.0041 (9)0.0041 (8)
N30.0213 (10)0.0212 (11)0.0191 (11)0.0051 (9)0.0015 (8)0.0052 (8)
O10.0326 (10)0.0139 (8)0.0254 (10)0.0062 (7)0.0036 (8)0.0040 (7)
O20.0233 (9)0.0211 (9)0.0271 (10)0.0010 (7)0.0041 (7)0.0038 (7)
C80.0199 (12)0.0146 (12)0.0222 (13)0.0015 (10)0.0007 (10)0.0051 (10)
C40.0225 (12)0.0117 (11)0.0206 (13)0.0050 (10)0.0011 (10)0.0008 (9)
N20.0378 (13)0.0168 (11)0.0239 (12)0.0120 (10)0.0091 (10)0.0012 (9)
C50.0252 (13)0.0181 (12)0.0220 (13)0.0063 (10)0.0024 (10)0.0024 (10)
C30.0245 (13)0.0190 (12)0.0233 (14)0.0046 (10)0.0047 (10)0.0007 (10)
C10.0302 (14)0.0182 (13)0.0267 (14)0.0082 (11)0.0046 (11)0.0030 (10)
C60.0235 (13)0.0206 (13)0.0290 (14)0.0044 (11)0.0001 (11)0.0040 (11)
C20.0350 (15)0.0248 (13)0.0172 (13)0.0086 (12)0.0027 (11)0.0021 (10)
C140.0278 (14)0.0219 (13)0.0289 (14)0.0030 (11)0.0013 (11)0.0077 (11)
C90.0231 (13)0.0276 (14)0.0246 (14)0.0043 (11)0.0003 (10)0.0012 (11)
C100.0335 (15)0.0280 (14)0.0289 (15)0.0006 (12)0.0028 (12)0.0082 (11)
C70.0414 (17)0.0422 (17)0.0266 (15)0.0029 (14)0.0070 (13)0.0082 (13)
C110.0406 (16)0.0396 (17)0.0297 (16)0.0049 (14)0.0050 (13)0.0133 (13)
C13A0.0235 (16)0.0214 (17)0.0369 (19)0.0007 (14)0.0061 (13)0.0012 (13)
C12A0.0298 (17)0.0321 (18)0.0335 (19)0.0038 (14)0.0085 (13)0.0084 (14)
Geometric parameters (Å, º) top
S1—N11.627 (2)C14—C13A1.506 (4)
S1—O11.4316 (16)C14—C13B1.506 (6)
S1—O21.4259 (18)C9—H9A0.9700
S1—C41.763 (3)C9—H9B0.9700
O3—C81.230 (3)C9—C101.518 (4)
N1—C81.395 (3)C10—H10A0.9700
N1—H10.76 (3)C10—H10B0.9700
N3—N21.411 (3)C10—C111.513 (4)
N3—C141.481 (3)C7—H7A0.9600
N3—C91.474 (3)C7—H7B0.9600
C8—N21.338 (3)C7—H7C0.9600
C4—C51.391 (3)C11—H11C0.9700
C4—C31.384 (3)C11—H11D0.9700
N2—H20.82 (3)C11—H11A0.9700
C5—H50.9300C11—H11B0.9700
C5—C61.386 (3)C11—C12A1.532 (4)
C3—H30.9300C11—C12B1.532 (6)
C3—C21.395 (4)C13A—H13A0.9700
C1—C61.388 (4)C13A—H13B0.9700
C1—C21.389 (4)C13A—C12A1.529 (4)
C1—C71.513 (4)C12A—H12A0.9700
C6—H60.9300C12A—H12B0.9700
C2—H2A0.9300C13B—H13C0.9700
C14—H14A0.9700C13B—H13D0.9700
C14—H14B0.9700C13B—C12B1.528 (6)
C14—H14C0.9700C12B—H12C0.9700
C14—H14D0.9700C12B—H12D0.9700
N1—S1—C4105.29 (11)H9A—C9—H9B107.8
O1—S1—N1104.48 (10)C10—C9—H9A109.1
O1—S1—C4108.61 (10)C10—C9—H9B109.1
O2—S1—N1110.59 (10)C9—C10—H10A108.1
O2—S1—O1118.97 (10)C9—C10—H10B108.1
O2—S1—C4108.07 (11)H10A—C10—H10B107.3
S1—N1—H1120 (2)C11—C10—C9116.7 (2)
C8—N1—S1125.48 (18)C11—C10—H10A108.1
C8—N1—H1115 (2)C11—C10—H10B108.1
N2—N3—C14108.65 (18)C1—C7—H7A109.5
N2—N3—C9109.51 (18)C1—C7—H7B109.5
C9—N3—C14117.3 (2)C1—C7—H7C109.5
O3—C8—N1122.6 (2)H7A—C7—H7B109.5
O3—C8—N2123.2 (2)H7A—C7—H7C109.5
N2—C8—N1114.2 (2)H7B—C7—H7C109.5
C5—C4—S1119.30 (18)C10—C11—H11C108.1
C3—C4—S1119.32 (19)C10—C11—H11D108.1
C3—C4—C5121.3 (2)C10—C11—H11A108.9
N3—N2—H2119 (2)C10—C11—H11B108.9
C8—N2—N3121.7 (2)C10—C11—C12A113.5 (2)
C8—N2—H2119 (2)C10—C11—C12B117.0 (11)
C4—C5—H5120.7H11C—C11—H11D107.3
C6—C5—C4118.6 (2)H11A—C11—H11B107.7
C6—C5—H5120.7C12A—C11—H11A108.9
C4—C3—H3120.6C12A—C11—H11B108.9
C4—C3—C2118.9 (2)C12B—C11—H11C108.1
C2—C3—H3120.6C12B—C11—H11D108.1
C6—C1—C2118.6 (2)C14—C13A—H13A108.0
C6—C1—C7120.3 (2)C14—C13A—H13B108.0
C2—C1—C7121.1 (2)C14—C13A—C12A117.2 (3)
C5—C6—C1121.6 (2)H13A—C13A—H13B107.2
C5—C6—H6119.2C12A—C13A—H13A108.0
C1—C6—H6119.2C12A—C13A—H13B108.0
C3—C2—H2A119.5C11—C12A—H12A109.1
C1—C2—C3121.0 (2)C11—C12A—H12B109.1
C1—C2—H2A119.5C13A—C12A—C11112.6 (2)
N3—C14—H14A108.1C13A—C12A—H12A109.1
N3—C14—H14B108.1C13A—C12A—H12B109.1
N3—C14—H14C109.9H12A—C12A—H12B107.8
N3—C14—H14D109.9C14—C13B—H13C107.7
N3—C14—C13A116.9 (2)C14—C13B—H13D107.7
N3—C14—C13B109.1 (13)C14—C13B—C12B118.3 (17)
H14A—C14—H14B107.3H13C—C13B—H13D107.1
H14C—C14—H14D108.3C12B—C13B—H13C107.7
C13A—C14—H14A108.1C12B—C13B—H13D107.7
C13A—C14—H14B108.1C11—C12B—H12C110.4
C13B—C14—H14C109.9C11—C12B—H12D110.4
C13B—C14—H14D109.9C13B—C12B—C11106.8 (16)
N3—C9—H9A109.1C13B—C12B—H12C110.4
N3—C9—H9B109.1C13B—C12B—H12D110.4
N3—C9—C10112.45 (19)H12C—C12B—H12D108.6
S1—N1—C8—O31.7 (3)N2—N3—C14—C13A154.8 (2)
S1—N1—C8—N2179.79 (18)N2—N3—C14—C13B177.7 (11)
S1—C4—C5—C6176.84 (17)N2—N3—C9—C10152.5 (2)
S1—C4—C3—C2176.79 (17)C5—C4—C3—C20.3 (3)
O3—C8—N2—N3178.4 (2)C3—C4—C5—C60.4 (3)
N1—S1—C4—C556.1 (2)C6—C1—C2—C30.9 (3)
N1—S1—C4—C3127.41 (18)C2—C1—C6—C51.0 (3)
N1—C8—N2—N33.2 (3)C14—N3—N2—C8112.8 (3)
N3—C14—C13A—C12A46.6 (4)C14—N3—C9—C1083.1 (3)
N3—C14—C13B—C12B70 (2)C14—C13A—C12A—C1185.3 (4)
N3—C9—C10—C1177.5 (3)C14—C13B—C12B—C1194 (3)
O1—S1—N1—C8172.8 (2)C9—N3—N2—C8117.8 (3)
O1—S1—C4—C555.4 (2)C9—N3—C14—C13A30.0 (3)
O1—S1—C4—C3121.15 (18)C9—N3—C14—C13B57.5 (11)
O2—S1—N1—C843.7 (2)C9—C10—C11—C12A57.9 (3)
O2—S1—C4—C5174.27 (17)C9—C10—C11—C12B11.8 (11)
O2—S1—C4—C39.2 (2)C10—C11—C12A—C13A66.9 (3)
C4—S1—N1—C872.8 (2)C10—C11—C12B—C13B58.7 (18)
C4—C5—C6—C10.7 (3)C7—C1—C6—C5179.3 (2)
C4—C3—C2—C10.6 (3)C7—C1—C2—C3179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.76 (3)2.41 (3)3.013 (3)137 (3)
N2—H2···O3ii0.82 (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) top
Crystal data top
C14H21N3O3SF(000) = 332
Mr = 311.40Dx = 1.373 Mg m3
Triclinic, P1Melting point: 444 K
a = 6.3091 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9270 (15) ÅCell parameters from 1573 reflections
c = 13.576 (3) Åθ = 3.5–28.6°
α = 81.882 (16)°µ = 0.23 mm1
β = 86.073 (16)°T = 100 K
γ = 85.167 (13)°Plate, colourless
V = 753.0 (2) Å30.45 × 0.3 × 0.05 mm
Z = 2
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3057 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2081 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.094
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 3.5°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1111
Tmin = 0.753, Tmax = 1.000l = 1616
10088 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.069 w = 1/[σ2(Fo2) + (0.0721P)2 + 0.2853P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.173(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.47 e Å3
3057 reflectionsΔρmin = 0.63 e Å3
200 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.054 (6)
Primary atom site location: structure-invariant direct methods
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.24796 (13)0.97848 (9)0.39256 (6)0.0193 (3)
O30.0587 (3)0.6762 (2)0.41186 (17)0.0220 (6)
N10.2545 (4)0.8362 (3)0.4822 (2)0.0178 (7)
N30.2938 (4)0.6344 (3)0.6454 (2)0.0201 (7)
O10.3462 (3)1.0952 (2)0.43185 (17)0.0210 (6)
O20.0397 (3)1.0102 (2)0.35772 (18)0.0226 (6)
C80.1579 (5)0.7009 (4)0.4825 (3)0.0200 (8)
C40.4168 (5)0.9174 (3)0.2949 (2)0.0176 (7)
N20.1844 (5)0.6006 (3)0.5649 (2)0.0222 (7)
C50.6262 (5)0.8655 (3)0.3129 (3)0.0202 (8)
H50.67530.85800.37660.024*
C30.3423 (5)0.9291 (4)0.2002 (3)0.0206 (8)
H30.20190.96410.18880.025*
C10.6918 (5)0.8360 (4)0.1380 (3)0.0230 (8)
C60.7617 (5)0.8247 (4)0.2337 (3)0.0239 (8)
H60.90180.78920.24530.029*
C20.4798 (5)0.8878 (4)0.1225 (3)0.0234 (8)
H2A0.42990.89480.05900.028*
C140.4970 (5)0.5378 (4)0.6527 (3)0.0240 (8)
H14A0.60260.58610.60630.029*
H14B0.47510.44150.63100.029*
C90.1481 (5)0.6295 (4)0.7354 (3)0.0217 (8)
H9A0.15060.52610.76920.026*
H9B0.00400.65930.71570.026*
C100.2070 (5)0.7335 (4)0.8079 (3)0.0259 (8)
H10A0.23700.83050.76980.031*
H10B0.08320.75140.85230.031*
C70.8410 (6)0.7885 (4)0.0541 (3)0.0321 (9)
H7A0.80450.84900.00740.048*
H7B0.82830.68340.04920.048*
H7C0.98500.80280.06730.048*
C110.3933 (6)0.6791 (4)0.8708 (3)0.0285 (9)
H11A0.35720.58910.91560.034*
H11B0.41700.75670.91120.034*
C130.5881 (5)0.5058 (4)0.7545 (3)0.0242 (8)
H13A0.73080.45760.74680.029*
H13B0.50290.43300.79580.029*
C120.6003 (5)0.6417 (4)0.8107 (3)0.0268 (9)
H12A0.71560.62010.85560.032*
H12B0.63300.72970.76330.032*
H10.317 (6)0.839 (4)0.530 (3)0.028 (11)*
H20.131 (6)0.516 (5)0.566 (3)0.032 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0216 (5)0.0104 (4)0.0270 (5)0.0015 (3)0.0028 (4)0.0049 (3)
O30.0248 (13)0.0146 (12)0.0283 (14)0.0036 (10)0.0058 (11)0.0053 (10)
N10.0217 (15)0.0096 (14)0.0238 (17)0.0032 (12)0.0057 (13)0.0040 (12)
N30.0193 (14)0.0154 (15)0.0274 (17)0.0014 (12)0.0034 (12)0.0088 (12)
O10.0256 (12)0.0078 (11)0.0306 (14)0.0026 (10)0.0039 (10)0.0040 (9)
O20.0216 (12)0.0138 (12)0.0326 (15)0.0011 (10)0.0032 (10)0.0047 (10)
C80.0175 (17)0.0131 (17)0.030 (2)0.0020 (14)0.0033 (15)0.0053 (15)
C40.0204 (17)0.0061 (15)0.0260 (19)0.0026 (14)0.0013 (14)0.0001 (13)
N20.0299 (17)0.0120 (15)0.0269 (17)0.0069 (13)0.0076 (13)0.0046 (12)
C50.0242 (18)0.0101 (16)0.027 (2)0.0054 (14)0.0041 (15)0.0017 (13)
C30.0231 (18)0.0098 (16)0.028 (2)0.0016 (14)0.0027 (15)0.0000 (14)
C10.0239 (18)0.0109 (16)0.035 (2)0.0045 (15)0.0008 (16)0.0055 (14)
C60.0206 (18)0.0144 (18)0.038 (2)0.0031 (15)0.0025 (16)0.0058 (15)
C20.033 (2)0.0171 (18)0.0216 (19)0.0049 (16)0.0030 (16)0.0042 (14)
C140.0249 (18)0.0168 (18)0.033 (2)0.0028 (15)0.0000 (16)0.0120 (15)
C90.0205 (17)0.0148 (17)0.030 (2)0.0014 (14)0.0022 (15)0.0034 (14)
C100.0272 (19)0.0203 (19)0.032 (2)0.0018 (16)0.0018 (16)0.0107 (15)
C70.036 (2)0.031 (2)0.031 (2)0.0045 (18)0.0048 (17)0.0098 (17)
C110.030 (2)0.024 (2)0.034 (2)0.0023 (16)0.0042 (17)0.0125 (16)
C130.0208 (18)0.0156 (18)0.036 (2)0.0002 (15)0.0039 (16)0.0037 (15)
C120.0217 (18)0.0245 (19)0.037 (2)0.0007 (16)0.0073 (16)0.0115 (16)
Geometric parameters (Å, º) top
S1—N11.630 (3)C2—H2A0.9300
S1—O11.437 (2)C14—H14A0.9700
S1—O21.420 (2)C14—H14B0.9700
S1—C41.761 (3)C14—C131.514 (5)
O3—C81.235 (4)C9—H9A0.9700
N1—C81.398 (4)C9—H9B0.9700
N1—H10.78 (4)C9—C101.528 (5)
N3—N21.411 (4)C10—H10A0.9700
N3—C141.485 (4)C10—H10B0.9700
N3—C91.477 (4)C10—C111.507 (5)
C8—N21.341 (4)C7—H7A0.9600
C4—C51.388 (5)C7—H7B0.9600
C4—C31.387 (5)C7—H7C0.9600
N2—H20.85 (4)C11—H11A0.9700
C5—H50.9300C11—H11B0.9700
C5—C61.398 (5)C11—C121.530 (5)
C3—H30.9300C13—H13A0.9700
C3—C21.390 (5)C13—H13B0.9700
C1—C61.388 (5)C13—C121.532 (5)
C1—C21.398 (5)C12—H12A0.9700
C1—C71.512 (5)C12—H12B0.9700
C6—H60.9300
N1—S1—C4105.42 (15)H14A—C14—H14B107.3
O1—S1—N1104.20 (14)C13—C14—H14A108.2
O1—S1—C4108.49 (14)C13—C14—H14B108.2
O2—S1—N1110.89 (14)N3—C9—H9A109.0
O2—S1—O1118.99 (14)N3—C9—H9B109.0
O2—S1—C4108.02 (15)N3—C9—C10112.7 (2)
S1—N1—H1121 (3)H9A—C9—H9B107.8
C8—N1—S1125.3 (2)C10—C9—H9A109.0
C8—N1—H1114 (3)C10—C9—H9B109.0
N2—N3—C14109.1 (3)C9—C10—H10A108.0
N2—N3—C9109.5 (2)C9—C10—H10B108.0
C9—N3—C14117.3 (3)H10A—C10—H10B107.3
O3—C8—N1122.3 (3)C11—C10—C9117.1 (3)
O3—C8—N2123.3 (3)C11—C10—H10A108.0
N2—C8—N1114.5 (3)C11—C10—H10B108.0
C5—C4—S1119.4 (3)C1—C7—H7A109.5
C3—C4—S1119.6 (3)C1—C7—H7B109.5
C3—C4—C5121.0 (3)C1—C7—H7C109.5
N3—N2—H2122 (3)H7A—C7—H7B109.5
C8—N2—N3121.7 (3)H7A—C7—H7C109.5
C8—N2—H2116 (3)H7B—C7—H7C109.5
C4—C5—H5120.6C10—C11—H11A108.7
C4—C5—C6118.8 (3)C10—C11—H11B108.7
C6—C5—H5120.6C10—C11—C12114.1 (3)
C4—C3—H3120.4H11A—C11—H11B107.6
C4—C3—C2119.2 (3)C12—C11—H11A108.7
C2—C3—H3120.4C12—C11—H11B108.7
C6—C1—C2118.3 (3)C14—C13—H13A108.0
C6—C1—C7120.3 (3)C14—C13—H13B108.0
C2—C1—C7121.4 (3)C14—C13—C12117.0 (3)
C5—C6—H6119.3H13A—C13—H13B107.3
C1—C6—C5121.5 (3)C12—C13—H13A108.0
C1—C6—H6119.3C12—C13—H13B108.0
C3—C2—C1121.2 (3)C11—C12—C13112.8 (3)
C3—C2—H2A119.4C11—C12—H12A109.0
C1—C2—H2A119.4C11—C12—H12B109.0
N3—C14—H14A108.2C13—C12—H12A109.0
N3—C14—H14B108.2C13—C12—H12B109.0
N3—C14—C13116.4 (3)H12A—C12—H12B107.8
S1—N1—C8—O31.1 (5)C4—C5—C6—C10.4 (5)
S1—N1—C8—N2179.7 (3)C4—C3—C2—C10.5 (5)
S1—C4—C5—C6176.8 (2)N2—N3—C14—C13154.4 (3)
S1—C4—C3—C2176.8 (2)N2—N3—C9—C10152.0 (3)
O3—C8—N2—N3178.2 (3)C5—C4—C3—C20.1 (4)
N1—S1—C4—C555.4 (3)C3—C4—C5—C60.1 (4)
N1—S1—C4—C3127.9 (2)C6—C1—C2—C30.9 (5)
N1—C8—N2—N32.5 (5)C2—C1—C6—C50.8 (5)
N3—C14—C13—C1248.0 (4)C14—N3—N2—C8111.9 (4)
N3—C9—C10—C1176.8 (4)C14—N3—C9—C1082.9 (3)
O1—S1—N1—C8173.3 (3)C14—C13—C12—C1185.8 (4)
O1—S1—C4—C555.8 (3)C9—N3—N2—C8118.5 (3)
O1—S1—C4—C3121.0 (2)C9—N3—C14—C1329.1 (4)
O2—S1—N1—C844.2 (3)C9—C10—C11—C1256.2 (4)
O2—S1—C4—C5174.0 (2)C10—C11—C12—C1365.9 (4)
O2—S1—C4—C39.3 (3)C7—C1—C6—C5178.9 (3)
C4—S1—N1—C872.5 (3)C7—C1—C2—C3178.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.78 (4)2.37 (4)2.991 (3)137 (4)
N2—H2···O3ii0.85 (4)2.15 (4)2.985 (3)168 (4)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+1, z+1.
 

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