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The title complex, C7H6N2S·C17H13NO3, consists of donor and acceptor π-stacks in the alternating ADD′–A′ pattern, through parallel displaced interactions, with a mean interplanar distance of 3.50 (3) Å. The complete three-dimensional supramolecular arrangement is achieved by both N—H...O and C—H...X (X = O, aryl) hydrogen-bonding interactions, which define an A...D...D...A′ hydrogen-bonded tetramer, among other supramolecular structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302155X/su6036sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302155X/su6036Isup2.hkl
Contains datablock I

CCDC reference: 199529

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.150
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C3 = 7.01 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 - C15 = 7.46 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C16 - C17 = 16.42 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C18 - C19 = 16.86 su PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C18 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C14 PLAT331_ALERT_2_B Small Av. Phenyl C-C Dist. C14 - C19 = 1.35 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.34 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.10 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C2 = 5.08 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C10 = 5.04 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C13 PLAT322_ALERT_2_C Check Hybridisation of S21 in Main Residue . ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C17 H13 N O3
0 ALERT level A = In general: serious problem 7 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 12 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 and WinGX2003 (Farrugia, 1999).

2-aminobenzothiazole–N-benzyl-2-oxo-2H-1-benzopyran-3-carboxamide (1/1) top
Crystal data top
C7H6N2S·C17H13NO3Z = 2
Mr = 429.49F(000) = 448
Triclinic, P1Dx = 1.357 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.833 (2) ÅCell parameters from 600 reflections
b = 12.526 (4) Åθ = 20.0–25.0°
c = 12.786 (4) ŵ = 0.19 mm1
α = 104.903 (5)°T = 293 K
β = 93.392 (5)°Needless, yellow
γ = 94.425 (5)°0.38 × 0.20 × 0.17 mm
V = 1050.9 (6) Å3
Data collection top
Bruker SMART area-detector
diffractometer
2251 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.946, Tmax = 0.967k = 1616
11581 measured reflectionsl = 1616
4674 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0722P)2]
where P = (Fo2 + 2Fc2)/3
4674 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. IR (KBr) ν/cm-1: 3330 (N—H), 1705 (C O lactone), 1652 (C O amide), 741 (C—S). 1H NMR δ(p.p.m.): 9.11 (t, 1H, NH), 8.87 (s, 1H, H4), 7.97 (d, 1H, H5), 7.73 (dd, 1H, H7), 7.62 (d, 1H, H24), 7.49 (d, 1H, H8), 7.44 (s, 2H, NH2), 7.42 (dd, 1H, H6), 7.35–7.22 (m, 5H, Ph), 7.30 (dd, 1H, H27), 7.17 (dd, 1H, H26), 6.97 (dd, 1H, H25), 4.52 (d, 1H, CH2); 13C NMR δ(p.p.m.): 166.4 (C22), 161.3 (C11), 160.3 (C2), 153.9 (C9), 152.8 (C29), 147.5 (C4), 138.9 (Ci), 134.1 (C7), 130.9 (C28), 130.2 (C5), 128.4 (Co), 127.4 (Cm), 126.9 (Cp), 125.4 (C25), 125.1 (C6), 120.8 (C24), 120.8 (C26), 119.1 (C3), 118.5 (C10), 117.1 (C27), 116.1 (C8), 42.7 (CH2).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C20.3709 (4)0.51277 (19)0.85583 (19)0.0623 (6)
C30.1953 (3)0.48262 (17)0.79946 (17)0.0548 (5)
C40.0188 (3)0.53273 (18)0.84417 (17)0.0592 (6)
H4A0.09250.51200.80850.071*
C50.1846 (3)0.6723 (2)0.9937 (2)0.0711 (7)
H5A0.30000.65420.96100.085*
C60.1931 (4)0.7527 (2)1.0889 (2)0.0807 (8)
H6A0.31340.79081.12010.097*
C70.0213 (4)0.7778 (2)1.1393 (2)0.0850 (8)
H7A0.02760.83211.20480.102*
C80.1560 (4)0.7236 (2)1.0936 (2)0.0768 (7)
H8A0.27060.74021.12760.092*
C90.1630 (3)0.64414 (19)0.99680 (18)0.0597 (6)
C100.0046 (3)0.61681 (18)0.94456 (17)0.0554 (5)
C110.2060 (4)0.39340 (19)0.69482 (19)0.0660 (6)
C130.4141 (5)0.2411 (2)0.5674 (2)0.0970 (9)
H13A0.28870.21920.54170.116*
H13B0.49040.25890.50880.116*
C140.5218 (4)0.14762 (18)0.59939 (17)0.0606 (6)
C150.4194 (4)0.0776 (2)0.6407 (2)0.0865 (8)
H15A0.28250.08770.64660.104*
C160.5097 (9)0.0069 (3)0.6738 (3)0.1375 (16)
H16A0.43710.05350.70330.165*
C170.6997 (8)0.0204 (4)0.6631 (4)0.165 (3)
H17A0.75880.07910.68570.198*
C180.8210 (6)0.0410 (6)0.6228 (4)0.183 (3)
H18A0.95740.02700.61620.220*
C190.7186 (5)0.1309 (3)0.5908 (3)0.1153 (12)
H19A0.79150.17870.56330.138*
C220.2421 (3)0.38882 (19)0.4329 (2)0.0603 (6)
C240.4941 (4)0.2560 (2)0.2090 (2)0.0748 (7)
H24A0.62120.29130.21810.090*
C250.4373 (5)0.1674 (2)0.1208 (2)0.0914 (9)
H25A0.52820.14210.07110.110*
C260.2468 (5)0.1147 (2)0.1044 (2)0.0978 (9)
H26A0.21090.05590.04340.117*
C270.1122 (5)0.1498 (2)0.1783 (2)0.0883 (8)
H27A0.01510.11470.16810.106*
C280.1679 (4)0.2381 (2)0.26842 (19)0.0678 (6)
C290.3585 (4)0.29227 (19)0.28433 (19)0.0613 (6)
N120.3809 (3)0.33853 (16)0.66013 (16)0.0803 (6)
H12A0.48070.36160.69420.096*
N220.2329 (3)0.46278 (16)0.52844 (16)0.0754 (6)
H22A0.33400.50820.55760.090*
H22B0.12580.46490.56070.090*
N230.3972 (3)0.37869 (15)0.37741 (15)0.0611 (5)
O10.3445 (2)0.59201 (13)0.95274 (12)0.0666 (4)
O20.5393 (2)0.47538 (14)0.82585 (14)0.0827 (5)
O110.0557 (3)0.37227 (14)0.64813 (14)0.0871 (5)
S210.03307 (9)0.29719 (5)0.37472 (6)0.0759 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0667 (16)0.0599 (15)0.0601 (15)0.0020 (12)0.0086 (13)0.0161 (13)
C30.0592 (14)0.0536 (13)0.0556 (13)0.0066 (11)0.0154 (11)0.0191 (11)
C40.0597 (14)0.0654 (15)0.0605 (15)0.0140 (12)0.0192 (12)0.0255 (12)
C50.0568 (15)0.0915 (18)0.0675 (17)0.0044 (13)0.0097 (13)0.0250 (15)
C60.0659 (17)0.097 (2)0.0725 (18)0.0072 (14)0.0012 (14)0.0158 (16)
C70.084 (2)0.095 (2)0.0669 (17)0.0087 (16)0.0057 (15)0.0049 (15)
C80.0666 (17)0.0935 (19)0.0635 (16)0.0122 (14)0.0115 (13)0.0059 (15)
C90.0534 (14)0.0680 (15)0.0586 (15)0.0075 (11)0.0094 (12)0.0168 (12)
C100.0546 (14)0.0613 (14)0.0531 (13)0.0064 (11)0.0084 (11)0.0189 (11)
C110.0872 (19)0.0570 (15)0.0581 (15)0.0032 (14)0.0139 (14)0.0218 (12)
C130.150 (3)0.0694 (18)0.0643 (17)0.0125 (18)0.0115 (17)0.0108 (15)
C140.0740 (17)0.0534 (14)0.0488 (13)0.0045 (12)0.0052 (11)0.0059 (11)
C150.100 (2)0.0809 (19)0.0718 (18)0.0119 (17)0.0120 (15)0.0110 (16)
C160.264 (6)0.068 (2)0.087 (2)0.015 (3)0.017 (3)0.0311 (19)
C170.177 (5)0.142 (4)0.133 (4)0.092 (4)0.083 (4)0.028 (3)
C180.076 (3)0.244 (7)0.157 (5)0.029 (3)0.043 (3)0.073 (5)
C190.070 (2)0.129 (3)0.127 (3)0.023 (2)0.003 (2)0.005 (2)
C220.0618 (15)0.0570 (14)0.0643 (15)0.0007 (11)0.0040 (12)0.0219 (12)
C240.0857 (18)0.0749 (17)0.0673 (17)0.0066 (14)0.0145 (14)0.0235 (15)
C250.123 (3)0.085 (2)0.0725 (19)0.0177 (18)0.0312 (18)0.0241 (17)
C260.133 (3)0.081 (2)0.0704 (19)0.0044 (19)0.0118 (19)0.0067 (16)
C270.103 (2)0.0790 (19)0.0739 (19)0.0127 (16)0.0013 (17)0.0117 (16)
C280.0754 (17)0.0625 (15)0.0657 (16)0.0011 (12)0.0034 (13)0.0201 (13)
C290.0724 (16)0.0585 (14)0.0580 (15)0.0052 (12)0.0073 (12)0.0242 (12)
N120.1044 (17)0.0568 (12)0.0717 (14)0.0077 (12)0.0150 (12)0.0054 (11)
N220.0609 (12)0.0816 (14)0.0747 (14)0.0060 (10)0.0133 (10)0.0064 (12)
N230.0584 (12)0.0659 (12)0.0604 (12)0.0008 (9)0.0073 (10)0.0204 (10)
O10.0515 (9)0.0776 (11)0.0667 (11)0.0073 (8)0.0137 (8)0.0094 (9)
O20.0579 (10)0.0907 (13)0.0888 (12)0.0081 (9)0.0089 (9)0.0081 (10)
O110.0994 (13)0.0873 (12)0.0725 (11)0.0116 (10)0.0358 (11)0.0103 (10)
S210.0644 (4)0.0759 (5)0.0809 (5)0.0087 (3)0.0071 (3)0.0128 (4)
Geometric parameters (Å, º) top
C2—O21.209 (3)C15—H15A0.9300
C2—O11.366 (3)C16—C171.291 (6)
C2—C31.461 (3)C16—H16A0.9300
C3—C41.339 (3)C17—C181.339 (8)
C3—C111.500 (3)C17—H17A0.9300
C4—C101.427 (3)C18—C191.440 (7)
C4—H4A0.9300C18—H18A0.9300
C5—C61.361 (3)C19—H19A0.9300
C5—C101.394 (3)C22—N231.306 (3)
C5—H5A0.9300C22—N221.338 (3)
C6—C71.391 (3)C22—S211.759 (2)
C6—H6A0.9300C24—C251.375 (4)
C7—C81.362 (3)C24—C291.392 (3)
C7—H7A0.9300C24—H24A0.9300
C8—C91.370 (3)C25—C261.392 (4)
C8—H8A0.9300C25—H25A0.9300
C9—O11.372 (2)C26—C271.373 (4)
C9—C101.382 (3)C26—H26A0.9300
C11—O111.231 (3)C27—C281.387 (3)
C11—N121.323 (3)C27—H27A0.9300
C13—N121.458 (3)C28—C291.400 (3)
C13—C141.494 (3)C28—S211.726 (3)
C13—H13A0.9700C29—N231.384 (3)
C13—H13B0.9700N12—H12A0.8600
C14—C191.338 (4)N22—H22A0.8600
C14—C151.351 (3)N22—H22B0.8600
C15—C161.357 (4)
O2—C2—O1115.8 (2)C17—C16—C15117.8 (4)
O2—C2—C3127.0 (2)C17—C16—H16A121.1
O1—C2—C3117.2 (2)C15—C16—H16A121.1
C4—C3—C2119.3 (2)C16—C17—C18127.0 (6)
C4—C3—C11118.8 (2)C16—C17—H17A116.5
C2—C3—C11121.8 (2)C18—C17—H17A116.5
C3—C4—C10122.4 (2)C17—C18—C19113.2 (4)
C3—C4—H4A118.8C17—C18—H18A123.4
C10—C4—H4A118.8C19—C18—H18A123.4
C6—C5—C10120.6 (2)C14—C19—C18122.0 (4)
C6—C5—H5A119.7C14—C19—H19A119.0
C10—C5—H5A119.7C18—C19—H19A119.0
C5—C6—C7119.8 (2)N23—C22—N22124.8 (2)
C5—C6—H6A120.1N23—C22—S21115.98 (18)
C7—C6—H6A120.1N22—C22—S21119.18 (18)
C8—C7—C6120.6 (3)C25—C24—C29119.0 (3)
C8—C7—H7A119.7C25—C24—H24A120.5
C6—C7—H7A119.7C29—C24—H24A120.5
C7—C8—C9119.0 (2)C24—C25—C26121.6 (3)
C7—C8—H8A120.5C24—C25—H25A119.2
C9—C8—H8A120.5C26—C25—H25A119.2
C8—C9—O1117.4 (2)C27—C26—C25119.8 (3)
C8—C9—C10121.9 (2)C27—C26—H26A120.1
O1—C9—C10120.7 (2)C25—C26—H26A120.1
C9—C10—C5118.0 (2)C26—C27—C28119.3 (3)
C9—C10—C4117.5 (2)C26—C27—H27A120.3
C5—C10—C4124.5 (2)C28—C27—H27A120.3
O11—C11—N12123.6 (2)C27—C28—C29120.9 (2)
O11—C11—C3120.0 (2)C27—C28—S21129.3 (2)
N12—C11—C3116.4 (2)C29—C28—S21109.78 (18)
N12—C13—C14110.0 (2)N23—C29—C24125.0 (2)
N12—C13—H13A109.7N23—C29—C28115.6 (2)
C14—C13—H13A109.7C24—C29—C28119.4 (2)
N12—C13—H13B109.7C11—N12—C13123.8 (2)
C14—C13—H13B109.7C11—N12—H12A118.1
H13A—C13—H13B108.2C13—N12—H12A118.1
C19—C14—C15117.8 (3)C22—N22—H22A120.0
C19—C14—C13122.5 (3)C22—N22—H22B120.0
C15—C14—C13119.6 (3)H22A—N22—H22B120.0
C14—C15—C16122.2 (3)C22—N23—C29109.9 (2)
C14—C15—H15A118.9C2—O1—C9122.87 (18)
C16—C15—H15A118.9C28—S21—C2288.64 (12)
O2—C2—C3—C4179.8 (2)C15—C14—C19—C180.7 (5)
O1—C2—C3—C40.1 (3)C13—C14—C19—C18179.4 (3)
O2—C2—C3—C112.9 (4)C17—C18—C19—C141.3 (7)
O1—C2—C3—C11177.45 (18)C29—C24—C25—C261.2 (4)
C2—C3—C4—C101.3 (3)C24—C25—C26—C271.3 (4)
C11—C3—C4—C10178.75 (18)C25—C26—C27—C280.4 (4)
C10—C5—C6—C71.8 (4)C26—C27—C28—C290.5 (4)
C5—C6—C7—C80.8 (4)C26—C27—C28—S21178.4 (2)
C6—C7—C8—C90.3 (4)C25—C24—C29—N23178.7 (2)
C7—C8—C9—O1179.4 (2)C25—C24—C29—C280.3 (3)
C7—C8—C9—C100.5 (4)C27—C28—C29—N23179.6 (2)
C8—C9—C10—C50.4 (3)S21—C28—C29—N230.5 (3)
O1—C9—C10—C5179.69 (19)C27—C28—C29—C240.6 (3)
C8—C9—C10—C4179.9 (2)S21—C28—C29—C24178.56 (17)
O1—C9—C10—C40.2 (3)O11—C11—N12—C135.0 (4)
C6—C5—C10—C91.5 (3)C3—C11—N12—C13172.6 (2)
C6—C5—C10—C4179.0 (2)C14—C13—N12—C11127.0 (3)
C3—C4—C10—C91.4 (3)N22—C22—N23—C29178.2 (2)
C3—C4—C10—C5179.2 (2)S21—C22—N23—C292.0 (2)
C4—C3—C11—O114.6 (3)C24—C29—N23—C22177.4 (2)
C2—C3—C11—O11178.1 (2)C28—C29—N23—C221.6 (3)
C4—C3—C11—N12173.1 (2)O2—C2—O1—C9178.64 (19)
C2—C3—C11—N124.3 (3)C3—C2—O1—C91.1 (3)
N12—C13—C14—C1990.3 (3)C8—C9—O1—C2178.9 (2)
N12—C13—C14—C1588.4 (3)C10—C9—O1—C21.0 (3)
C19—C14—C15—C160.6 (4)C27—C28—S21—C22178.5 (2)
C13—C14—C15—C16178.2 (3)C29—C28—S21—C220.50 (17)
C14—C15—C16—C171.2 (5)N23—C22—S21—C281.51 (18)
C15—C16—C17—C180.5 (8)N22—C22—S21—C28178.70 (19)
C16—C17—C18—C190.7 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H12A···O20.861.992.700 (3)139
N22—H22A···N23i0.862.213.069 (3)176
N22—H22B···O110.862.182.902 (3)142
C4—H4A···O2ii0.932.603.417 (3)147
C4—H4A···O110.932.432.764 (3)101
C13—H13A···O110.972.452.823 (4)103
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z.
 

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