





Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616015145/su4057sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2414314616015145/su4057Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616015145/su4057Isup3.cml |
CCDC reference: 1506723
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean
(C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.049
- wR factor = 0.150
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density 0 Note
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 7 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 6 Report PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 5 Report PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT301_ALERT_3_G Main Residue Disorder ............ Percentage = 18 Note PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 8 Note PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note H2 O PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 90 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 39 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 12 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Data collection: SAINT (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C10H16ClN5S·H2O | F(000) = 616 |
Mr = 291.80 | Dx = 1.252 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.494 (4) Å | Cell parameters from 5524 reflections |
b = 17.665 (10) Å | θ = 2.3–24.9° |
c = 13.508 (8) Å | µ = 0.38 mm−1 |
β = 92.402 (9)° | T = 300 K |
V = 1548.2 (16) Å3 | Block, yellow |
Z = 4 | 0.3 × 0.2 × 0.14 mm |
Bruker SMART CCD area detector diffractometer | 2347 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
phi and ω scans | θmax = 26.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −8→8 |
Tmin = 0.895, Tmax = 0.949 | k = −22→21 |
15205 measured reflections | l = −16→16 |
3151 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: mixed |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0896P)2 + 0.1249P] where P = (Fo2 + 2Fc2)/3 |
3151 reflections | (Δ/σ)max = 0.001 |
192 parameters | Δρmax = 0.23 e Å−3 |
90 restraints | Δρmin = −0.31 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H,H) groups 2. Restrained distances C9A-C10A = C9-C10 = C9-C8 = C9A-C8A = C8-C7 = C8A-C7 1.54 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints C8 ~C8A ~C9 ~C9A ~C10 ~C10A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.02 4. Rigid body (RIGU) restrains C8, C8A, C9, C9A, C10, C10A with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5. Others Sof(H7BC)=Sof(H7BD)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)= Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1) Sof(H7AA)=Sof(H7AB)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=Sof(H9B)= Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1) 6.a Riding coordinates: O1(H1D,H1E) 6.b Secondary CH2 refined with riding coordinates: C7(H7AA,H7AB), C7(H7BC,H7BD), C8(H8A,H8B), C8A(H8AA,H8AB), C9(H9A,H9B), C9A(H9AA,H9AB) 6.c Me refined with riding coordinates: C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F) 6.d Aromatic/amide H refined with riding coordinates: N1(H1), N4(H4), N5(H5), C3(H3) 6.e Idealised Me refined as rotating group: C1(H1A,H1B,H1C) |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 1.09917 (13) | 0.28647 (5) | 1.33664 (5) | 0.1203 (3) | |
S1 | 1.40870 (8) | 0.50705 (3) | 0.84042 (4) | 0.0775 (2) | |
N1 | 0.7716 (2) | 0.30301 (9) | 1.09668 (13) | 0.0680 (4) | |
H1 | 0.7390 | 0.3177 | 1.0374 | 0.082* | |
N2 | 0.7516 (3) | 0.24365 (10) | 1.23866 (15) | 0.0803 (5) | |
N3 | 1.0786 (2) | 0.39480 (9) | 1.02455 (12) | 0.0676 (4) | |
N4 | 1.2297 (2) | 0.43919 (9) | 0.98710 (13) | 0.0713 (4) | |
H4 | 1.3325 | 0.4541 | 1.0243 | 0.086* | |
N5 | 1.0461 (3) | 0.43806 (11) | 0.84178 (13) | 0.0777 (5) | |
H5 | 0.9546 | 0.4141 | 0.8737 | 0.093* | |
C1 | 1.0031 (4) | 0.45223 (17) | 0.73736 (19) | 0.1025 (8) | |
H1A | 0.9799 | 0.5054 | 0.7270 | 0.154* | |
H1B | 0.8824 | 0.4245 | 0.7155 | 0.154* | |
H1C | 1.1184 | 0.4362 | 0.7004 | 0.154* | |
C2 | 1.2143 (3) | 0.45908 (10) | 0.89093 (15) | 0.0650 (5) | |
C3 | 1.0989 (3) | 0.37222 (11) | 1.11367 (16) | 0.0689 (5) | |
H3 | 1.2117 | 0.3870 | 1.1538 | 0.083* | |
C4 | 0.9444 (3) | 0.32364 (11) | 1.15086 (14) | 0.0668 (5) | |
C5 | 0.9271 (3) | 0.28602 (12) | 1.23801 (17) | 0.0776 (6) | |
C6 | 0.6607 (3) | 0.25575 (11) | 1.15151 (18) | 0.0726 (5) | |
C7 | 0.4665 (4) | 0.21935 (15) | 1.1134 (2) | 0.0981 (8) | |
H7AA | 0.3930 | 0.2024 | 1.1704 | 0.118* | 0.491 (9) |
H7AB | 0.3830 | 0.2585 | 1.0812 | 0.118* | 0.491 (9) |
H7BC | 0.4113 | 0.2473 | 1.0565 | 0.118* | 0.509 (9) |
H7BD | 0.3654 | 0.2206 | 1.1642 | 0.118* | 0.509 (9) |
C8 | 0.4739 (19) | 0.1576 (8) | 1.0468 (9) | 0.138 (4) | 0.491 (9) |
H8A | 0.4192 | 0.1769 | 0.9838 | 0.166* | 0.491 (9) |
H8B | 0.3732 | 0.1216 | 1.0692 | 0.166* | 0.491 (9) |
C8A | 0.5058 (15) | 0.1367 (5) | 1.0833 (7) | 0.101 (2) | 0.509 (9) |
H8AA | 0.3772 | 0.1097 | 1.0707 | 0.122* | 0.509 (9) |
H8AB | 0.5871 | 0.1102 | 1.1343 | 0.122* | 0.509 (9) |
C9 | 0.6576 (17) | 0.1117 (7) | 1.0227 (7) | 0.141 (3) | 0.491 (9) |
H9A | 0.6684 | 0.0647 | 1.0598 | 0.169* | 0.491 (9) |
H9B | 0.7858 | 0.1398 | 1.0288 | 0.169* | 0.491 (9) |
C9A | 0.6316 (17) | 0.1452 (5) | 0.9831 (7) | 0.130 (3) | 0.509 (9) |
H9AA | 0.5431 | 0.1671 | 0.9310 | 0.157* | 0.509 (9) |
H9AB | 0.7488 | 0.1785 | 0.9949 | 0.157* | 0.509 (9) |
C10 | 0.5775 (17) | 0.1002 (7) | 0.9120 (6) | 0.157 (3) | 0.491 (9) |
H10A | 0.6748 | 0.0702 | 0.8776 | 0.235* | 0.491 (9) |
H10B | 0.4467 | 0.0747 | 0.9108 | 0.235* | 0.491 (9) |
H10C | 0.5621 | 0.1486 | 0.8803 | 0.235* | 0.491 (9) |
C10A | 0.708 (2) | 0.0645 (5) | 0.9501 (9) | 0.173 (4) | 0.509 (9) |
H10D | 0.7830 | 0.0693 | 0.8906 | 0.259* | 0.509 (9) |
H10E | 0.7966 | 0.0433 | 1.0016 | 0.259* | 0.509 (9) |
H10F | 0.5915 | 0.0319 | 0.9379 | 0.259* | 0.509 (9) |
O1 | 0.6591 (2) | 0.15312 (9) | 1.40012 (11) | 0.0909 (5) | |
H1D | 0.6078 | 0.1117 | 1.3785 | 0.136* | |
H1E | 0.6784 | 0.1808 | 1.3499 | 0.136* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1252 (6) | 0.1591 (8) | 0.0757 (5) | −0.0300 (5) | −0.0068 (4) | 0.0263 (4) |
S1 | 0.0773 (4) | 0.0824 (4) | 0.0740 (4) | −0.0057 (2) | 0.0155 (3) | 0.0169 (3) |
N1 | 0.0741 (9) | 0.0658 (9) | 0.0648 (10) | 0.0046 (7) | 0.0131 (8) | 0.0015 (8) |
N2 | 0.0886 (11) | 0.0791 (11) | 0.0750 (13) | −0.0082 (9) | 0.0248 (10) | 0.0076 (9) |
N3 | 0.0701 (9) | 0.0660 (9) | 0.0678 (11) | −0.0028 (7) | 0.0160 (7) | 0.0061 (8) |
N4 | 0.0708 (9) | 0.0766 (10) | 0.0671 (11) | −0.0081 (8) | 0.0091 (8) | 0.0110 (8) |
N5 | 0.0788 (11) | 0.0886 (12) | 0.0664 (11) | −0.0083 (9) | 0.0103 (9) | 0.0075 (9) |
C1 | 0.1038 (17) | 0.132 (2) | 0.0707 (16) | −0.0195 (16) | −0.0034 (13) | 0.0140 (15) |
C2 | 0.0692 (11) | 0.0610 (11) | 0.0656 (12) | 0.0053 (8) | 0.0138 (9) | 0.0047 (9) |
C3 | 0.0759 (11) | 0.0653 (11) | 0.0661 (13) | −0.0026 (9) | 0.0101 (9) | 0.0034 (9) |
C4 | 0.0760 (11) | 0.0633 (11) | 0.0619 (12) | −0.0017 (9) | 0.0146 (9) | 0.0001 (9) |
C5 | 0.0891 (14) | 0.0808 (13) | 0.0636 (13) | −0.0051 (11) | 0.0133 (10) | 0.0068 (10) |
C6 | 0.0743 (11) | 0.0682 (12) | 0.0771 (15) | 0.0021 (9) | 0.0231 (10) | −0.0008 (10) |
C7 | 0.0727 (13) | 0.0956 (17) | 0.127 (2) | −0.0029 (12) | 0.0189 (13) | 0.0024 (16) |
C8 | 0.123 (6) | 0.180 (8) | 0.110 (7) | −0.019 (5) | −0.016 (5) | −0.040 (6) |
C8A | 0.086 (4) | 0.115 (5) | 0.101 (5) | −0.017 (3) | −0.013 (4) | −0.027 (4) |
C9 | 0.173 (5) | 0.138 (7) | 0.111 (6) | 0.018 (5) | −0.001 (5) | −0.024 (5) |
C9A | 0.165 (6) | 0.119 (5) | 0.109 (6) | −0.019 (4) | 0.027 (5) | −0.041 (4) |
C10 | 0.182 (7) | 0.172 (7) | 0.115 (5) | 0.007 (6) | 0.003 (5) | −0.018 (5) |
C10A | 0.227 (8) | 0.136 (6) | 0.159 (7) | −0.014 (5) | 0.057 (6) | −0.057 (5) |
O1 | 0.1094 (11) | 0.0934 (10) | 0.0699 (10) | −0.0319 (9) | 0.0023 (8) | 0.0073 (8) |
Cl1—C5 | 1.703 (3) | C7—H7BD | 0.9700 |
S1—C2 | 1.688 (2) | C7—C8 | 1.415 (11) |
N1—H1 | 0.8600 | C7—C8A | 1.540 (9) |
N1—C4 | 1.363 (3) | C8—H8A | 0.9700 |
N1—C6 | 1.345 (3) | C8—H8B | 0.9700 |
N2—C5 | 1.364 (3) | C8—C9 | 1.490 (13) |
N2—C6 | 1.312 (3) | C8A—H8AA | 0.9700 |
N3—N4 | 1.370 (2) | C8A—H8AB | 0.9700 |
N3—C3 | 1.270 (3) | C8A—C9A | 1.617 (12) |
N4—H4 | 0.8600 | C9—H9A | 0.9700 |
N4—C2 | 1.345 (3) | C9—H9B | 0.9700 |
N5—H5 | 0.8600 | C9—C10 | 1.575 (12) |
N5—C1 | 1.448 (3) | C9A—H9AA | 0.9700 |
N5—C2 | 1.308 (3) | C9A—H9AB | 0.9700 |
C1—H1A | 0.9600 | C9A—C10A | 1.580 (12) |
C1—H1B | 0.9600 | C10—H10A | 0.9600 |
C1—H1C | 0.9600 | C10—H10B | 0.9600 |
C3—H3 | 0.9300 | C10—H10C | 0.9600 |
C3—C4 | 1.428 (3) | C10A—H10D | 0.9600 |
C4—C5 | 1.361 (3) | C10A—H10E | 0.9600 |
C6—C7 | 1.488 (3) | C10A—H10F | 0.9600 |
C7—H7AA | 0.9700 | O1—H1D | 0.8500 |
C7—H7AB | 0.9700 | O1—H1E | 0.8500 |
C7—H7BC | 0.9700 | ||
C4—N1—H1 | 125.7 | C8—C7—H7AB | 107.3 |
C6—N1—H1 | 125.7 | C8A—C7—H7BC | 109.5 |
C6—N1—C4 | 108.54 (19) | C8A—C7—H7BD | 109.5 |
C6—N2—C5 | 104.44 (17) | C7—C8—H8A | 105.5 |
C3—N3—N4 | 118.86 (17) | C7—C8—H8B | 105.5 |
N3—N4—H4 | 120.6 | C7—C8—C9 | 127.4 (10) |
C2—N4—N3 | 118.74 (17) | H8A—C8—H8B | 106.0 |
C2—N4—H4 | 120.6 | C9—C8—H8A | 105.5 |
C1—N5—H5 | 117.7 | C9—C8—H8B | 105.5 |
C2—N5—H5 | 117.7 | C7—C8A—H8AA | 111.1 |
C2—N5—C1 | 124.62 (18) | C7—C8A—H8AB | 111.1 |
N5—C1—H1A | 109.5 | C7—C8A—C9A | 103.1 (7) |
N5—C1—H1B | 109.5 | H8AA—C8A—H8AB | 109.1 |
N5—C1—H1C | 109.5 | C9A—C8A—H8AA | 111.1 |
H1A—C1—H1B | 109.5 | C9A—C8A—H8AB | 111.1 |
H1A—C1—H1C | 109.5 | C8—C9—H9A | 113.2 |
H1B—C1—H1C | 109.5 | C8—C9—H9B | 113.2 |
N4—C2—S1 | 119.65 (16) | C8—C9—C10 | 92.4 (10) |
N5—C2—S1 | 124.06 (17) | H9A—C9—H9B | 110.6 |
N5—C2—N4 | 116.27 (17) | C10—C9—H9A | 113.2 |
N3—C3—H3 | 120.8 | C10—C9—H9B | 113.2 |
N3—C3—C4 | 118.4 (2) | C8A—C9A—H9AA | 109.8 |
C4—C3—H3 | 120.8 | C8A—C9A—H9AB | 109.8 |
N1—C4—C3 | 123.13 (19) | H9AA—C9A—H9AB | 108.3 |
C5—C4—N1 | 103.76 (18) | C10A—C9A—C8A | 109.2 (9) |
C5—C4—C3 | 133.1 (2) | C10A—C9A—H9AA | 109.8 |
N2—C5—Cl1 | 121.25 (17) | C10A—C9A—H9AB | 109.8 |
C4—C5—Cl1 | 126.82 (18) | C9—C10—H10A | 109.5 |
C4—C5—N2 | 111.9 (2) | C9—C10—H10B | 109.5 |
N1—C6—C7 | 122.9 (2) | C9—C10—H10C | 109.5 |
N2—C6—N1 | 111.4 (2) | H10A—C10—H10B | 109.5 |
N2—C6—C7 | 125.6 (2) | H10A—C10—H10C | 109.5 |
C6—C7—H7AA | 107.3 | H10B—C10—H10C | 109.5 |
C6—C7—H7AB | 107.3 | C9A—C10A—H10D | 109.5 |
C6—C7—H7BC | 109.5 | C9A—C10A—H10E | 109.5 |
C6—C7—H7BD | 109.5 | C9A—C10A—H10F | 109.5 |
C6—C7—C8A | 110.7 (4) | H10D—C10A—H10E | 109.5 |
H7AA—C7—H7AB | 106.9 | H10D—C10A—H10F | 109.5 |
H7BC—C7—H7BD | 108.1 | H10E—C10A—H10F | 109.5 |
C8—C7—C6 | 120.1 (5) | H1D—O1—H1E | 106.8 |
C8—C7—H7AA | 107.3 | ||
N1—C4—C5—Cl1 | 178.29 (17) | C3—C4—C5—N2 | −177.9 (2) |
N1—C4—C5—N2 | 0.0 (2) | C4—N1—C6—N2 | −0.4 (2) |
N1—C6—C7—C8 | 75.8 (8) | C4—N1—C6—C7 | −177.11 (19) |
N1—C6—C7—C8A | 101.2 (4) | C5—N2—C6—N1 | 0.4 (2) |
N2—C6—C7—C8 | −100.3 (8) | C5—N2—C6—C7 | 177.0 (2) |
N2—C6—C7—C8A | −75.0 (5) | C6—N1—C4—C3 | 178.42 (17) |
N3—N4—C2—S1 | −174.50 (13) | C6—N1—C4—C5 | 0.2 (2) |
N3—N4—C2—N5 | 4.4 (3) | C6—N2—C5—Cl1 | −178.66 (17) |
N3—C3—C4—N1 | −3.0 (3) | C6—N2—C5—C4 | −0.3 (2) |
N3—C3—C4—C5 | 174.6 (2) | C6—C7—C8—C9 | 13 (2) |
N4—N3—C3—C4 | −177.68 (16) | C6—C7—C8A—C9A | −72.0 (8) |
C1—N5—C2—S1 | 0.5 (3) | C7—C8—C9—C10 | −146.0 (13) |
C1—N5—C2—N4 | −178.3 (2) | C7—C8A—C9A—C10A | 172.9 (8) |
C3—N3—N4—C2 | 175.86 (17) | C8—C7—C8A—C9A | 45.5 (17) |
C3—C4—C5—Cl1 | 0.4 (4) | C8A—C7—C8—C9 | −60.1 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1E···N2 | 0.85 | 1.94 | 2.790 (3) | 174 |
N1—H1···O1i | 0.86 | 1.97 | 2.832 (3) | 177 |
N5—H5···O1i | 0.86 | 2.30 | 3.114 (3) | 159 |
O1—H1D···S1ii | 0.85 | 2.51 | 3.345 (2) | 169 |
N4—H4···S1iii | 0.86 | 2.52 | 3.374 (2) | 169 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z+1/2; (iii) −x+3, −y+1, −z+2. |