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In the structures of two title compounds, the 4H-chromene derivative mol­ecules are linked by N—H...O and N—H...N hydrogen bonds, forming double layers or ribbons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019013197/yk2126sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013197/yk2126Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013197/yk2126IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019013197/yk2126Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019013197/yk2126IIsup5.cml
Supplementary material

CCDC references: 1865757; 1865762

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Some non-H atoms missing
  • R factor = 0.044
  • wR factor = 0.121
  • Data-to-parameter ratio = 13.6
Structure: II
  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • Some non-H atoms missing
  • R factor = 0.033
  • wR factor = 0.081
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full ! Check PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ Please Check PLAT043_ALERT_1_C Calculated and Reported Mol. Weight Differ by .. 1.01 Check PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... Please Check PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors of C20 Check PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of O16 Check PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.4 Note PLAT260_ALERT_2_C Large Average Ueq of Residue Including O16 0.107 Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 ..CL2 . 2.87 Ang. PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.595 5 Report
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C20 H17 Cl2 N2 O4 Atom count from the _atom_site data: C20 H18 Cl2 N2 O4 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C20 H17 Cl2 N2 O4 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 80.00 80.00 0.00 H 68.00 72.00 -4.00 Cl 8.00 8.00 0.00 N 8.00 8.00 0.00 O 16.00 16.00 0.00 PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT398_ALERT_2_G Deviating C-O-C Angle From 120 for O19 109.9 Degree PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 3 Note PLAT793_ALERT_4_G Model has Chirality at C7 (Centro SPGR) S Verify PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 59% Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 4 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 5 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 10 ALERT level C = Check. Ensure it is not caused by an omission or oversight 15 ALERT level G = General information/check it is not something unexpected 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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
Datablock: II
Alert level C PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full ! Check PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ Please Check PLAT043_ALERT_1_C Calculated and Reported Mol. Weight Differ by .. 1.01 Check PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... Please Check PLAT420_ALERT_2_C D-H Without Acceptor N2 --HnA . Please Check PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 ..N1 . 3.10 Ang. 1+x,y,z = 1_655 Check PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 9 Note PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.595 20 Report PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 6 Note
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C16 H9 Cl2 N2 O2 Atom count from the _atom_site data: C16 H10 Cl2 N2 O2 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C16 H9 Cl2 N2 O2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 32.00 32.00 0.00 H 18.00 20.00 -2.00 Cl 4.00 4.00 0.00 N 4.00 4.00 0.00 O 4.00 4.00 0.00 PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 3 Note PLAT793_ALERT_4_G Model has Chirality at C7 (Centro SPGR) R Verify PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 81% Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 5 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 12 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 9 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: APEX3 (Bruker, 2018); cell refinement: APEX3 and SAINT (Bruker, 2018); data reduction: SAINT and XPREP (Bruker, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2007) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

2-Amino-3-cyano-4-(3,4-dichlorophenyl)-7-hydroxy-4H-benzo[1,2-b]pyran 1,4-dioxane monosolvate (I) top
Crystal data top
C16H9Cl2N2O2·C4H8O2Dx = 1.401 Mg m3
Mr = 420.25Melting point: 520 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.753 (9) ÅCell parameters from 9965 reflections
b = 6.665 (4) Åθ = 3.2–26.7°
c = 24.050 (14) ŵ = 0.36 mm1
β = 102.95 (3)°T = 294 K
V = 1992 (2) Å3Block, colourless
Z = 40.15 × 0.15 × 0.10 mm
F(000) = 868
Data collection top
Bruker Kappa APEX3 CMOS
diffractometer
3492 independent reflections
Radiation source: fine-focus sealed tube2885 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω and φ scanθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2018)
h = 1515
Tmin = 0.704, Tmax = 0.745k = 77
34682 measured reflectionsl = 2826
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0541P)2 + 1.1852P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
3492 reflectionsΔρmax = 0.26 e Å3
256 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0174 (18)
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.

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 > 2sigma(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
Cl10.60648 (5)0.18411 (11)0.42962 (4)0.0702 (3)
Cl20.52933 (5)0.63066 (11)0.40894 (4)0.0679 (3)
O10.12386 (15)0.8018 (3)0.63654 (6)0.0519 (5)
HO10.15450.73860.66480.074 (10)*
O20.07140 (12)0.8197 (2)0.43851 (6)0.0379 (4)
N20.01565 (18)0.8571 (3)0.34552 (8)0.0530 (6)
HNA0.00510.82070.31040.064*
HNB0.00320.97500.35400.064*
N10.0608 (2)0.3924 (4)0.28098 (9)0.0748 (8)
C30.47549 (17)0.2502 (4)0.42953 (10)0.0424 (6)
C40.40418 (19)0.1065 (4)0.43879 (12)0.0512 (6)
H40.42660.02600.44520.061*
C50.29931 (18)0.1579 (3)0.43861 (11)0.0439 (6)
H50.25160.05920.44480.053*
C60.26401 (16)0.3532 (3)0.42946 (8)0.0303 (5)
C70.14837 (15)0.4087 (3)0.43059 (8)0.0305 (5)
H70.10680.28410.42790.037*
C110.14231 (15)0.5105 (3)0.48595 (8)0.0292 (4)
C120.17291 (16)0.4127 (3)0.53832 (9)0.0358 (5)
H120.19800.28150.53910.043*
C130.16731 (17)0.5037 (4)0.58889 (9)0.0382 (5)
H130.18680.43370.62310.046*
C140.13242 (16)0.7003 (3)0.58846 (8)0.0354 (5)
C100.10667 (15)0.7052 (3)0.48756 (8)0.0291 (4)
C150.10195 (16)0.8023 (3)0.53756 (8)0.0337 (5)
H150.07860.93460.53690.040*
C90.06130 (16)0.7304 (3)0.38688 (8)0.0342 (5)
C80.09544 (16)0.5416 (3)0.38111 (8)0.0347 (5)
C220.07678 (19)0.4596 (4)0.32560 (10)0.0459 (6)
C10.33627 (17)0.4972 (3)0.42043 (9)0.0361 (5)
H10.31400.62980.41430.043*
C20.44144 (17)0.4463 (3)0.42042 (9)0.0380 (5)
O160.24114 (17)0.6481 (4)0.73252 (9)0.0769 (6)
C170.2288 (3)0.5035 (7)0.77295 (16)0.0937 (12)
H1710.15650.44910.76300.112*
H1720.23890.56590.81020.112*
C180.3066 (3)0.3413 (7)0.7754 (2)0.1008 (13)
H1810.29760.24500.80420.121*
H1820.29300.27270.73890.121*
O190.4122 (2)0.4128 (5)0.78824 (13)0.1129 (10)
C200.4249 (4)0.5602 (9)0.7484 (3)0.140 (2)
H2010.41590.49860.71110.169*
H2020.49740.61370.75900.169*
C210.3484 (3)0.7239 (7)0.7450 (2)0.1147 (16)
H2110.36220.79570.78100.138*
H2120.35730.81710.71540.138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0349 (3)0.0613 (5)0.1189 (7)0.0130 (3)0.0268 (4)0.0064 (4)
Cl20.0449 (4)0.0492 (4)0.1188 (7)0.0051 (3)0.0379 (4)0.0059 (4)
O10.0682 (12)0.0615 (11)0.0250 (8)0.0233 (9)0.0080 (8)0.0009 (8)
O20.0528 (9)0.0356 (8)0.0245 (7)0.0081 (7)0.0070 (6)0.0006 (6)
N20.0766 (15)0.0540 (13)0.0266 (10)0.0236 (11)0.0079 (9)0.0035 (9)
N10.100 (2)0.0820 (18)0.0351 (13)0.0287 (16)0.0006 (12)0.0151 (12)
C30.0294 (11)0.0424 (13)0.0557 (14)0.0061 (10)0.0105 (10)0.0031 (11)
C40.0408 (13)0.0324 (12)0.0819 (18)0.0077 (10)0.0171 (12)0.0016 (12)
C50.0362 (12)0.0333 (12)0.0634 (15)0.0015 (10)0.0138 (11)0.0009 (11)
C60.0300 (10)0.0334 (11)0.0273 (10)0.0020 (9)0.0059 (8)0.0045 (9)
C70.0258 (10)0.0325 (11)0.0328 (11)0.0011 (8)0.0062 (8)0.0046 (9)
C110.0220 (9)0.0354 (11)0.0305 (10)0.0020 (8)0.0062 (8)0.0008 (9)
C120.0333 (11)0.0346 (12)0.0394 (12)0.0048 (9)0.0082 (9)0.0041 (9)
C130.0374 (12)0.0481 (14)0.0285 (11)0.0053 (10)0.0060 (9)0.0080 (10)
C140.0305 (11)0.0481 (13)0.0275 (11)0.0035 (9)0.0065 (8)0.0018 (9)
C100.0244 (9)0.0370 (11)0.0253 (10)0.0007 (8)0.0042 (8)0.0035 (9)
C150.0323 (11)0.0377 (12)0.0306 (11)0.0046 (9)0.0061 (8)0.0010 (9)
C90.0317 (11)0.0455 (13)0.0261 (10)0.0020 (9)0.0079 (8)0.0005 (9)
C80.0284 (10)0.0474 (13)0.0274 (10)0.0041 (9)0.0043 (8)0.0054 (9)
C220.0459 (13)0.0541 (15)0.0347 (13)0.0145 (11)0.0028 (10)0.0041 (11)
C10.0344 (11)0.0306 (11)0.0450 (12)0.0042 (9)0.0126 (9)0.0021 (9)
C20.0320 (11)0.0395 (12)0.0439 (12)0.0026 (9)0.0115 (9)0.0032 (10)
O160.0632 (13)0.0935 (16)0.0644 (13)0.0044 (12)0.0062 (10)0.0279 (12)
C170.067 (2)0.126 (3)0.091 (2)0.018 (2)0.0234 (18)0.049 (2)
C180.082 (3)0.096 (3)0.126 (3)0.008 (2)0.027 (2)0.042 (2)
O190.0663 (16)0.131 (3)0.137 (2)0.0268 (17)0.0141 (15)0.043 (2)
C200.075 (3)0.139 (4)0.219 (6)0.007 (3)0.056 (3)0.052 (5)
C210.079 (3)0.108 (3)0.141 (4)0.018 (3)0.008 (2)0.034 (3)
Geometric parameters (Å, º) top
Cl1—C31.727 (2)C12—H120.9300
Cl2—C21.727 (2)C13—C141.383 (3)
O1—C141.365 (3)C13—H130.9300
O1—HO10.8200C14—C151.378 (3)
O2—C91.357 (3)C10—C151.379 (3)
O2—C101.393 (2)C15—H150.9300
N2—C91.335 (3)C9—C81.349 (3)
N2—HNA0.8600C8—C221.413 (3)
N2—HNB0.8600C1—C21.384 (3)
N1—C221.138 (3)C1—H10.9300
C3—C41.373 (3)O16—C171.403 (4)
C3—C21.379 (3)O16—C211.426 (5)
C4—C51.380 (3)C17—C181.459 (5)
C4—H40.9300C17—H1710.9700
C5—C61.379 (3)C17—H1720.9700
C5—H50.9300C18—O191.396 (5)
C6—C11.381 (3)C18—H1810.9700
C6—C71.527 (3)C18—H1820.9700
C7—C111.512 (3)O19—C201.406 (5)
C7—C81.515 (3)C20—C211.453 (7)
C7—H70.9800C20—H2010.9700
C11—C101.378 (3)C20—H2020.9700
C11—C121.394 (3)C21—H2110.9700
C12—C131.375 (3)C21—H2120.9700
C14—O1—HO1109.5C10—C15—H15120.5
C9—O2—C10118.75 (17)N2—C9—C8127.6 (2)
C9—N2—HNA120.0N2—C9—O2109.9 (2)
C9—N2—HNB120.0C8—C9—O2122.48 (19)
HNA—N2—HNB120.0C9—C8—C22117.9 (2)
C4—C3—C2119.4 (2)C9—C8—C7124.17 (18)
C4—C3—Cl1119.81 (19)C22—C8—C7117.8 (2)
C2—C3—Cl1120.80 (18)N1—C22—C8179.3 (3)
C3—C4—C5120.2 (2)C6—C1—C2120.7 (2)
C3—C4—H4119.9C6—C1—H1119.6
C5—C4—H4119.9C2—C1—H1119.6
C6—C5—C4121.1 (2)C3—C2—C1120.2 (2)
C6—C5—H5119.4C3—C2—Cl2120.48 (17)
C4—C5—H5119.4C1—C2—Cl2119.31 (18)
C5—C6—C1118.41 (19)C17—O16—C21110.4 (3)
C5—C6—C7120.53 (19)O16—C17—C18110.9 (3)
C1—C6—C7121.05 (19)O16—C17—H171109.5
C11—C7—C8109.13 (17)C18—C17—H171109.5
C11—C7—C6111.39 (16)O16—C17—H172109.5
C8—C7—C6112.94 (16)C18—C17—H172109.5
C11—C7—H7107.7H171—C17—H172108.1
C8—C7—H7107.7O19—C18—C17111.6 (4)
C6—C7—H7107.7O19—C18—H181109.3
C10—C11—C12116.24 (18)C17—C18—H181109.3
C10—C11—C7121.97 (18)O19—C18—H182109.3
C12—C11—C7121.79 (19)C17—C18—H182109.3
C13—C12—C11122.2 (2)H181—C18—H182108.0
C13—C12—H12118.9C18—O19—C20109.9 (3)
C11—C12—H12118.9O19—C20—C21112.6 (4)
C12—C13—C14119.5 (2)O19—C20—H201109.1
C12—C13—H13120.3C21—C20—H201109.1
C14—C13—H13120.3O19—C20—H202109.1
O1—C14—C15116.6 (2)C21—C20—H202109.1
O1—C14—C13123.34 (19)H201—C20—H202107.8
C15—C14—C13120.01 (19)O16—C21—C20110.2 (4)
C11—C10—C15123.07 (18)O16—C21—H211109.6
C11—C10—O2122.57 (17)C20—C21—H211109.6
C15—C10—O2114.36 (18)O16—C21—H212109.6
C14—C15—C10119.0 (2)C20—C21—H212109.6
C14—C15—H15120.5H211—C21—H212108.1
C2—C3—C4—C50.4 (4)C11—C10—C15—C141.1 (3)
Cl1—C3—C4—C5179.8 (2)O2—C10—C15—C14178.35 (18)
C3—C4—C5—C60.3 (4)C10—O2—C9—N2173.17 (18)
C4—C5—C6—C10.0 (3)C10—O2—C9—C87.7 (3)
C4—C5—C6—C7178.7 (2)N2—C9—C8—C223.7 (3)
C5—C6—C7—C11102.8 (2)O2—C9—C8—C22177.2 (2)
C1—C6—C7—C1175.9 (2)N2—C9—C8—C7178.9 (2)
C5—C6—C7—C8134.0 (2)O2—C9—C8—C70.1 (3)
C1—C6—C7—C847.3 (3)C11—C7—C8—C97.6 (3)
C8—C7—C11—C108.1 (2)C6—C7—C8—C9116.9 (2)
C6—C7—C11—C10117.2 (2)C11—C7—C8—C22169.73 (19)
C8—C7—C11—C12172.12 (18)C6—C7—C8—C2265.8 (2)
C6—C7—C11—C1262.5 (2)C5—C6—C1—C20.2 (3)
C10—C11—C12—C130.5 (3)C7—C6—C1—C2178.92 (19)
C7—C11—C12—C13179.75 (19)C4—C3—C2—C10.2 (4)
C11—C12—C13—C141.4 (3)Cl1—C3—C2—C1179.98 (18)
C12—C13—C14—O1179.6 (2)C4—C3—C2—Cl2179.7 (2)
C12—C13—C14—C151.1 (3)Cl1—C3—C2—Cl20.1 (3)
C12—C11—C10—C150.8 (3)C6—C1—C2—C30.1 (3)
C7—C11—C10—C15178.98 (18)C6—C1—C2—Cl2179.97 (16)
C12—C11—C10—O2178.63 (18)C21—O16—C17—C1856.6 (5)
C7—C11—C10—O21.6 (3)O16—C17—C18—O1957.7 (5)
C9—O2—C10—C116.9 (3)C17—C18—O19—C2056.0 (5)
C9—O2—C10—C15172.56 (18)C18—O19—C20—C2155.8 (6)
O1—C14—C15—C10178.52 (19)C17—O16—C21—C2055.5 (5)
C13—C14—C15—C100.1 (3)O19—C20—C21—O1655.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—HO1···O160.821.852.658 (3)167
N2—HNB···O1i0.862.192.978 (3)153
N2—HNA···N1ii0.862.222.989 (3)149
C4—H4···Cl2iii0.932.873.692 (3)148
Symmetry codes: (i) x, y+2, z+1; (ii) x, y+1/2, z+1/2; (iii) x, y1, z.
2-Amino-3-cyano-4-(2,6-dichlorophenyl)-7-hydroxy-4H-\ benzo[1,2-b]pyran (II) top
Crystal data top
C16H9Cl2N2O2F(000) = 338
Mr = 332.15Dx = 1.548 Mg m3
Triclinic, P1Melting point: 514 K
a = 6.271 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.697 (5) ÅCell parameters from 8750 reflections
c = 13.794 (7) Åθ = 3.1–30.4°
α = 107.06 (2)°µ = 0.46 mm1
β = 94.269 (17)°T = 294 K
γ = 95.00 (3)°Block, colourless
V = 712.5 (7) Å30.15 × 0.15 × 0.10 mm
Z = 2
Data collection top
Bruker Kappa APEX3 CMOS
diffractometer
2499 independent reflections
Radiation source: fine-focus sealed tube2239 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω and φ scanθmax = 25.0°, θmin = 3.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2018)
h = 77
Tmin = 0.704, Tmax = 0.746k = 1010
22289 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0263P)2 + 0.4717P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
2499 reflectionsΔρmax = 0.23 e Å3
204 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.080 (10)
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.

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 > 2sigma(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
Cl10.84692 (8)0.84534 (6)0.32241 (4)0.04703 (19)
Cl20.10752 (8)0.50064 (7)0.36100 (4)0.0536 (2)
O11.0482 (2)0.15972 (18)0.09764 (12)0.0484 (4)
HO11.058 (5)0.092 (4)0.130 (2)0.084 (10)*
O20.7394 (2)0.62001 (14)0.07971 (9)0.0331 (3)
N10.1786 (3)0.9314 (2)0.18547 (15)0.0538 (5)
N20.6119 (3)0.83118 (18)0.04811 (12)0.0372 (4)
HNB0.71280.82660.00870.045*
HNA0.52620.90460.05400.045*
C140.8930 (3)0.2578 (2)0.12922 (13)0.0314 (4)
C130.7476 (3)0.2339 (2)0.19616 (13)0.0327 (4)
H130.74980.14520.22070.039*
C120.6001 (3)0.3428 (2)0.22588 (13)0.0303 (4)
H120.50330.32580.27060.036*
C110.5912 (3)0.47743 (19)0.19116 (12)0.0252 (4)
C70.4337 (3)0.59914 (19)0.22777 (12)0.0244 (3)
H70.28920.53940.21310.029*
C60.4733 (3)0.67923 (19)0.34378 (12)0.0256 (4)
C10.3324 (3)0.6415 (2)0.40945 (13)0.0340 (4)
C20.3630 (4)0.7086 (3)0.51432 (15)0.0489 (5)
H20.26370.68080.55490.059*
C30.5406 (4)0.8159 (3)0.55754 (15)0.0545 (6)
H30.56230.86210.62800.065*
C80.4401 (3)0.7173 (2)0.16603 (12)0.0272 (4)
C220.2927 (3)0.8338 (2)0.17803 (13)0.0333 (4)
C90.5883 (3)0.72374 (19)0.10034 (12)0.0270 (4)
C100.7341 (3)0.49354 (19)0.12257 (12)0.0258 (4)
C150.8841 (3)0.3873 (2)0.09093 (13)0.0306 (4)
H150.97780.40280.04460.037*
C40.6873 (4)0.8561 (3)0.49742 (15)0.0482 (5)
H40.80940.92820.52690.058*
C50.6524 (3)0.7886 (2)0.39261 (13)0.0333 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0390 (3)0.0566 (3)0.0404 (3)0.0157 (2)0.0042 (2)0.0129 (2)
Cl20.0435 (3)0.0712 (4)0.0448 (3)0.0174 (2)0.0084 (2)0.0216 (3)
O10.0615 (10)0.0440 (8)0.0580 (9)0.0319 (7)0.0295 (7)0.0303 (7)
O20.0421 (7)0.0305 (6)0.0376 (7)0.0150 (5)0.0189 (5)0.0204 (5)
N10.0546 (11)0.0603 (12)0.0685 (12)0.0324 (10)0.0294 (9)0.0405 (10)
N20.0469 (9)0.0356 (8)0.0409 (9)0.0166 (7)0.0178 (7)0.0231 (7)
C140.0388 (10)0.0269 (8)0.0303 (9)0.0110 (7)0.0057 (7)0.0088 (7)
C130.0433 (10)0.0254 (8)0.0340 (9)0.0057 (7)0.0052 (8)0.0154 (7)
C120.0362 (9)0.0298 (9)0.0276 (8)0.0013 (7)0.0063 (7)0.0128 (7)
C110.0289 (8)0.0243 (8)0.0222 (8)0.0023 (6)0.0012 (6)0.0071 (6)
C70.0235 (8)0.0264 (8)0.0242 (8)0.0026 (6)0.0033 (6)0.0090 (6)
C60.0285 (8)0.0259 (8)0.0247 (8)0.0063 (7)0.0043 (6)0.0098 (7)
C10.0354 (10)0.0376 (10)0.0314 (9)0.0017 (8)0.0065 (7)0.0139 (8)
C20.0648 (14)0.0541 (12)0.0293 (10)0.0009 (11)0.0165 (9)0.0143 (9)
C30.0846 (17)0.0510 (13)0.0232 (9)0.0059 (12)0.0054 (10)0.0076 (9)
C80.0309 (9)0.0284 (8)0.0249 (8)0.0082 (7)0.0036 (7)0.0107 (7)
C220.0358 (9)0.0374 (10)0.0341 (9)0.0099 (8)0.0097 (7)0.0191 (8)
C90.0325 (9)0.0252 (8)0.0255 (8)0.0085 (7)0.0032 (7)0.0094 (7)
C100.0328 (9)0.0232 (8)0.0248 (8)0.0055 (7)0.0043 (7)0.0113 (6)
C150.0362 (9)0.0304 (9)0.0299 (9)0.0092 (7)0.0109 (7)0.0130 (7)
C40.0604 (13)0.0444 (11)0.0323 (10)0.0108 (10)0.0050 (9)0.0073 (9)
C50.0375 (10)0.0336 (9)0.0298 (9)0.0002 (7)0.0057 (7)0.0118 (7)
Geometric parameters (Å, º) top
Cl1—C51.7383 (19)C11—C71.515 (2)
Cl2—C11.736 (2)C7—C81.515 (2)
O1—C141.362 (2)C7—C61.538 (2)
O1—HO10.85 (3)C7—H70.9800
O2—C91.353 (2)C6—C51.394 (3)
O2—C101.392 (2)C6—C11.397 (2)
N1—C221.144 (2)C1—C21.383 (3)
N2—C91.342 (2)C2—C31.364 (3)
N2—HNB0.8600C2—H20.9300
N2—HNA0.8600C3—C41.373 (3)
C14—C151.381 (2)C3—H30.9300
C14—C131.390 (3)C8—C91.354 (2)
C13—C121.380 (3)C8—C221.413 (2)
C13—H130.9300C10—C151.380 (2)
C12—C111.392 (2)C15—H150.9300
C12—H120.9300C4—C51.384 (3)
C11—C101.378 (2)C4—H40.9300
C14—O1—HO1112 (2)C2—C1—Cl2116.30 (15)
C9—O2—C10118.64 (13)C6—C1—Cl2120.20 (14)
C9—N2—HNB120.0C3—C2—C1119.25 (19)
C9—N2—HNA120.0C3—C2—H2120.4
HNB—N2—HNA120.0C1—C2—H2120.4
O1—C14—C15116.39 (16)C2—C3—C4120.18 (19)
O1—C14—C13123.88 (16)C2—C3—H3119.9
C15—C14—C13119.73 (16)C4—C3—H3119.9
C12—C13—C14119.48 (15)C9—C8—C22115.95 (15)
C12—C13—H13120.3C9—C8—C7123.49 (14)
C14—C13—H13120.3C22—C8—C7120.51 (15)
C13—C12—C11122.22 (16)N1—C22—C8177.10 (19)
C13—C12—H12118.9N2—C9—O2110.03 (14)
C11—C12—H12118.9N2—C9—C8126.71 (15)
C10—C11—C12116.26 (15)O2—C9—C8123.25 (15)
C10—C11—C7122.30 (14)C11—C10—C15123.29 (15)
C12—C11—C7121.44 (15)C11—C10—O2122.40 (14)
C11—C7—C8109.10 (13)C15—C10—O2114.31 (14)
C11—C7—C6111.28 (13)C10—C15—C14118.96 (16)
C8—C7—C6114.32 (14)C10—C15—H15120.5
C11—C7—H7107.3C14—C15—H15120.5
C8—C7—H7107.3C3—C4—C5119.6 (2)
C6—C7—H7107.3C3—C4—H4120.2
C5—C6—C1114.50 (15)C5—C4—H4120.2
C5—C6—C7124.05 (14)C4—C5—C6123.02 (17)
C1—C6—C7121.41 (15)C4—C5—Cl1116.49 (15)
C2—C1—C6123.48 (18)C6—C5—Cl1120.49 (13)
O1—C14—C13—C12178.13 (17)C10—O2—C9—N2176.56 (14)
C15—C14—C13—C121.9 (3)C10—O2—C9—C84.5 (2)
C14—C13—C12—C110.1 (3)C22—C8—C9—N21.8 (3)
C13—C12—C11—C102.0 (2)C7—C8—C9—N2175.57 (16)
C13—C12—C11—C7177.63 (15)C22—C8—C9—O2179.42 (15)
C10—C11—C7—C88.4 (2)C7—C8—C9—O23.2 (3)
C12—C11—C7—C8172.08 (15)C12—C11—C10—C152.0 (2)
C10—C11—C7—C6118.71 (17)C7—C11—C10—C15177.61 (15)
C12—C11—C7—C660.9 (2)C12—C11—C10—O2178.39 (15)
C11—C7—C6—C570.1 (2)C7—C11—C10—O22.0 (2)
C8—C7—C6—C554.1 (2)C9—O2—C10—C115.0 (2)
C11—C7—C6—C1107.41 (18)C9—O2—C10—C15175.30 (15)
C8—C7—C6—C1128.44 (17)C11—C10—C15—C140.1 (3)
C5—C6—C1—C21.3 (3)O2—C10—C15—C14179.77 (15)
C7—C6—C1—C2179.01 (18)O1—C14—C15—C10178.14 (16)
C5—C6—C1—Cl2177.27 (13)C13—C14—C15—C101.9 (3)
C7—C6—C1—Cl20.4 (2)C2—C3—C4—C50.9 (4)
C6—C1—C2—C30.9 (3)C3—C4—C5—C60.3 (3)
Cl2—C1—C2—C3177.78 (18)C3—C4—C5—Cl1179.69 (18)
C1—C2—C3—C40.3 (4)C1—C6—C5—C40.7 (3)
C11—C7—C8—C99.1 (2)C7—C6—C5—C4178.35 (17)
C6—C7—C8—C9116.24 (18)C1—C6—C5—Cl1178.63 (13)
C11—C7—C8—C22173.69 (15)C7—C6—C5—Cl11.0 (2)
C6—C7—C8—C2261.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···Cl20.982.503.078 (3)117
N2—HNB···O1i0.862.193.048 (2)173
O1—HO1···N1ii0.85 (3)1.95 (3)2.762 (2)160 (3)
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y1, z.
 

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