In the structures of two title compounds, the 4
H-chromene derivative molecules are linked by N—H

O and N—H

N hydrogen bonds, forming double layers or ribbons.
Supporting information
CCDC references: 1865757; 1865762
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 294 K
- Mean
(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
(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
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-4
H-benzo[1,2-
b]pyran 1,4-dioxane monosolvate (I)
top
Crystal data top
C16H9Cl2N2O2·C4H8O2 | Dx = 1.401 Mg m−3 |
Mr = 420.25 | Melting point: 520 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.753 (9) Å | Cell parameters from 9965 reflections |
b = 6.665 (4) Å | θ = 3.2–26.7° |
c = 24.050 (14) Å | µ = 0.36 mm−1 |
β = 102.95 (3)° | T = 294 K |
V = 1992 (2) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.15 × 0.10 mm |
F(000) = 868 | |
Data collection top
Bruker Kappa APEX3 CMOS diffractometer | 3492 independent reflections |
Radiation source: fine-focus sealed tube | 2885 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and φ scan | θmax = 25.0°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2018) | h = −15→15 |
Tmin = 0.704, Tmax = 0.745 | k = −7→7 |
34682 measured reflections | l = −28→26 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | H 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 reflections | Δρmax = 0.26 e Å−3 |
256 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.60648 (5) | 0.18411 (11) | 0.42962 (4) | 0.0702 (3) | |
Cl2 | 0.52933 (5) | 0.63066 (11) | 0.40894 (4) | 0.0679 (3) | |
O1 | 0.12386 (15) | 0.8018 (3) | 0.63654 (6) | 0.0519 (5) | |
HO1 | 0.1545 | 0.7386 | 0.6648 | 0.074 (10)* | |
O2 | 0.07140 (12) | 0.8197 (2) | 0.43851 (6) | 0.0379 (4) | |
N2 | 0.01565 (18) | 0.8571 (3) | 0.34552 (8) | 0.0530 (6) | |
HNA | 0.0051 | 0.8207 | 0.3104 | 0.064* | |
HNB | −0.0032 | 0.9750 | 0.3540 | 0.064* | |
N1 | 0.0608 (2) | 0.3924 (4) | 0.28098 (9) | 0.0748 (8) | |
C3 | 0.47549 (17) | 0.2502 (4) | 0.42953 (10) | 0.0424 (6) | |
C4 | 0.40418 (19) | 0.1065 (4) | 0.43879 (12) | 0.0512 (6) | |
H4 | 0.4266 | −0.0260 | 0.4452 | 0.061* | |
C5 | 0.29931 (18) | 0.1579 (3) | 0.43861 (11) | 0.0439 (6) | |
H5 | 0.2516 | 0.0592 | 0.4448 | 0.053* | |
C6 | 0.26401 (16) | 0.3532 (3) | 0.42946 (8) | 0.0303 (5) | |
C7 | 0.14837 (15) | 0.4087 (3) | 0.43059 (8) | 0.0305 (5) | |
H7 | 0.1068 | 0.2841 | 0.4279 | 0.037* | |
C11 | 0.14231 (15) | 0.5105 (3) | 0.48595 (8) | 0.0292 (4) | |
C12 | 0.17291 (16) | 0.4127 (3) | 0.53832 (9) | 0.0358 (5) | |
H12 | 0.1980 | 0.2815 | 0.5391 | 0.043* | |
C13 | 0.16731 (17) | 0.5037 (4) | 0.58889 (9) | 0.0382 (5) | |
H13 | 0.1868 | 0.4337 | 0.6231 | 0.046* | |
C14 | 0.13242 (16) | 0.7003 (3) | 0.58846 (8) | 0.0354 (5) | |
C10 | 0.10667 (15) | 0.7052 (3) | 0.48756 (8) | 0.0291 (4) | |
C15 | 0.10195 (16) | 0.8023 (3) | 0.53756 (8) | 0.0337 (5) | |
H15 | 0.0786 | 0.9346 | 0.5369 | 0.040* | |
C9 | 0.06130 (16) | 0.7304 (3) | 0.38688 (8) | 0.0342 (5) | |
C8 | 0.09544 (16) | 0.5416 (3) | 0.38111 (8) | 0.0347 (5) | |
C22 | 0.07678 (19) | 0.4596 (4) | 0.32560 (10) | 0.0459 (6) | |
C1 | 0.33627 (17) | 0.4972 (3) | 0.42043 (9) | 0.0361 (5) | |
H1 | 0.3140 | 0.6298 | 0.4143 | 0.043* | |
C2 | 0.44144 (17) | 0.4463 (3) | 0.42042 (9) | 0.0380 (5) | |
O16 | 0.24114 (17) | 0.6481 (4) | 0.73252 (9) | 0.0769 (6) | |
C17 | 0.2288 (3) | 0.5035 (7) | 0.77295 (16) | 0.0937 (12) | |
H171 | 0.1565 | 0.4491 | 0.7630 | 0.112* | |
H172 | 0.2389 | 0.5659 | 0.8102 | 0.112* | |
C18 | 0.3066 (3) | 0.3413 (7) | 0.7754 (2) | 0.1008 (13) | |
H181 | 0.2976 | 0.2450 | 0.8042 | 0.121* | |
H182 | 0.2930 | 0.2727 | 0.7389 | 0.121* | |
O19 | 0.4122 (2) | 0.4128 (5) | 0.78824 (13) | 0.1129 (10) | |
C20 | 0.4249 (4) | 0.5602 (9) | 0.7484 (3) | 0.140 (2) | |
H201 | 0.4159 | 0.4986 | 0.7111 | 0.169* | |
H202 | 0.4974 | 0.6137 | 0.7590 | 0.169* | |
C21 | 0.3484 (3) | 0.7239 (7) | 0.7450 (2) | 0.1147 (16) | |
H211 | 0.3622 | 0.7957 | 0.7810 | 0.138* | |
H212 | 0.3573 | 0.8171 | 0.7154 | 0.138* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0349 (3) | 0.0613 (5) | 0.1189 (7) | 0.0130 (3) | 0.0268 (4) | 0.0064 (4) |
Cl2 | 0.0449 (4) | 0.0492 (4) | 0.1188 (7) | −0.0051 (3) | 0.0379 (4) | 0.0059 (4) |
O1 | 0.0682 (12) | 0.0615 (11) | 0.0250 (8) | 0.0233 (9) | 0.0080 (8) | −0.0009 (8) |
O2 | 0.0528 (9) | 0.0356 (8) | 0.0245 (7) | 0.0081 (7) | 0.0070 (6) | 0.0006 (6) |
N2 | 0.0766 (15) | 0.0540 (13) | 0.0266 (10) | 0.0236 (11) | 0.0079 (9) | 0.0035 (9) |
N1 | 0.100 (2) | 0.0820 (18) | 0.0351 (13) | 0.0287 (16) | −0.0006 (12) | −0.0151 (12) |
C3 | 0.0294 (11) | 0.0424 (13) | 0.0557 (14) | 0.0061 (10) | 0.0105 (10) | −0.0031 (11) |
C4 | 0.0408 (13) | 0.0324 (12) | 0.0819 (18) | 0.0077 (10) | 0.0171 (12) | 0.0016 (12) |
C5 | 0.0362 (12) | 0.0333 (12) | 0.0634 (15) | −0.0015 (10) | 0.0138 (11) | −0.0009 (11) |
C6 | 0.0300 (10) | 0.0334 (11) | 0.0273 (10) | 0.0020 (9) | 0.0059 (8) | −0.0045 (9) |
C7 | 0.0258 (10) | 0.0325 (11) | 0.0328 (11) | −0.0011 (8) | 0.0062 (8) | −0.0046 (9) |
C11 | 0.0220 (9) | 0.0354 (11) | 0.0305 (10) | −0.0020 (8) | 0.0062 (8) | −0.0008 (9) |
C12 | 0.0333 (11) | 0.0346 (12) | 0.0394 (12) | 0.0048 (9) | 0.0082 (9) | 0.0041 (9) |
C13 | 0.0374 (12) | 0.0481 (14) | 0.0285 (11) | 0.0053 (10) | 0.0060 (9) | 0.0080 (10) |
C14 | 0.0305 (11) | 0.0481 (13) | 0.0275 (11) | 0.0035 (9) | 0.0065 (8) | −0.0018 (9) |
C10 | 0.0244 (9) | 0.0370 (11) | 0.0253 (10) | −0.0007 (8) | 0.0042 (8) | 0.0035 (9) |
C15 | 0.0323 (11) | 0.0377 (12) | 0.0306 (11) | 0.0046 (9) | 0.0061 (8) | −0.0010 (9) |
C9 | 0.0317 (11) | 0.0455 (13) | 0.0261 (10) | 0.0020 (9) | 0.0079 (8) | 0.0005 (9) |
C8 | 0.0284 (10) | 0.0474 (13) | 0.0274 (10) | 0.0041 (9) | 0.0043 (8) | −0.0054 (9) |
C22 | 0.0459 (13) | 0.0541 (15) | 0.0347 (13) | 0.0145 (11) | 0.0028 (10) | −0.0041 (11) |
C1 | 0.0344 (11) | 0.0306 (11) | 0.0450 (12) | 0.0042 (9) | 0.0126 (9) | −0.0021 (9) |
C2 | 0.0320 (11) | 0.0395 (12) | 0.0439 (12) | −0.0026 (9) | 0.0115 (9) | −0.0032 (10) |
O16 | 0.0632 (13) | 0.0935 (16) | 0.0644 (13) | 0.0044 (12) | −0.0062 (10) | 0.0279 (12) |
C17 | 0.067 (2) | 0.126 (3) | 0.091 (2) | 0.018 (2) | 0.0234 (18) | 0.049 (2) |
C18 | 0.082 (3) | 0.096 (3) | 0.126 (3) | 0.008 (2) | 0.027 (2) | 0.042 (2) |
O19 | 0.0663 (16) | 0.131 (3) | 0.137 (2) | 0.0268 (17) | 0.0141 (15) | 0.043 (2) |
C20 | 0.075 (3) | 0.139 (4) | 0.219 (6) | 0.007 (3) | 0.056 (3) | 0.052 (5) |
C21 | 0.079 (3) | 0.108 (3) | 0.141 (4) | −0.018 (3) | −0.008 (2) | 0.034 (3) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.727 (2) | C12—H12 | 0.9300 |
Cl2—C2 | 1.727 (2) | C13—C14 | 1.383 (3) |
O1—C14 | 1.365 (3) | C13—H13 | 0.9300 |
O1—HO1 | 0.8200 | C14—C15 | 1.378 (3) |
O2—C9 | 1.357 (3) | C10—C15 | 1.379 (3) |
O2—C10 | 1.393 (2) | C15—H15 | 0.9300 |
N2—C9 | 1.335 (3) | C9—C8 | 1.349 (3) |
N2—HNA | 0.8600 | C8—C22 | 1.413 (3) |
N2—HNB | 0.8600 | C1—C2 | 1.384 (3) |
N1—C22 | 1.138 (3) | C1—H1 | 0.9300 |
C3—C4 | 1.373 (3) | O16—C17 | 1.403 (4) |
C3—C2 | 1.379 (3) | O16—C21 | 1.426 (5) |
C4—C5 | 1.380 (3) | C17—C18 | 1.459 (5) |
C4—H4 | 0.9300 | C17—H171 | 0.9700 |
C5—C6 | 1.379 (3) | C17—H172 | 0.9700 |
C5—H5 | 0.9300 | C18—O19 | 1.396 (5) |
C6—C1 | 1.381 (3) | C18—H181 | 0.9700 |
C6—C7 | 1.527 (3) | C18—H182 | 0.9700 |
C7—C11 | 1.512 (3) | O19—C20 | 1.406 (5) |
C7—C8 | 1.515 (3) | C20—C21 | 1.453 (7) |
C7—H7 | 0.9800 | C20—H201 | 0.9700 |
C11—C10 | 1.378 (3) | C20—H202 | 0.9700 |
C11—C12 | 1.394 (3) | C21—H211 | 0.9700 |
C12—C13 | 1.375 (3) | C21—H212 | 0.9700 |
| | | |
C14—O1—HO1 | 109.5 | C10—C15—H15 | 120.5 |
C9—O2—C10 | 118.75 (17) | N2—C9—C8 | 127.6 (2) |
C9—N2—HNA | 120.0 | N2—C9—O2 | 109.9 (2) |
C9—N2—HNB | 120.0 | C8—C9—O2 | 122.48 (19) |
HNA—N2—HNB | 120.0 | C9—C8—C22 | 117.9 (2) |
C4—C3—C2 | 119.4 (2) | C9—C8—C7 | 124.17 (18) |
C4—C3—Cl1 | 119.81 (19) | C22—C8—C7 | 117.8 (2) |
C2—C3—Cl1 | 120.80 (18) | N1—C22—C8 | 179.3 (3) |
C3—C4—C5 | 120.2 (2) | C6—C1—C2 | 120.7 (2) |
C3—C4—H4 | 119.9 | C6—C1—H1 | 119.6 |
C5—C4—H4 | 119.9 | C2—C1—H1 | 119.6 |
C6—C5—C4 | 121.1 (2) | C3—C2—C1 | 120.2 (2) |
C6—C5—H5 | 119.4 | C3—C2—Cl2 | 120.48 (17) |
C4—C5—H5 | 119.4 | C1—C2—Cl2 | 119.31 (18) |
C5—C6—C1 | 118.41 (19) | C17—O16—C21 | 110.4 (3) |
C5—C6—C7 | 120.53 (19) | O16—C17—C18 | 110.9 (3) |
C1—C6—C7 | 121.05 (19) | O16—C17—H171 | 109.5 |
C11—C7—C8 | 109.13 (17) | C18—C17—H171 | 109.5 |
C11—C7—C6 | 111.39 (16) | O16—C17—H172 | 109.5 |
C8—C7—C6 | 112.94 (16) | C18—C17—H172 | 109.5 |
C11—C7—H7 | 107.7 | H171—C17—H172 | 108.1 |
C8—C7—H7 | 107.7 | O19—C18—C17 | 111.6 (4) |
C6—C7—H7 | 107.7 | O19—C18—H181 | 109.3 |
C10—C11—C12 | 116.24 (18) | C17—C18—H181 | 109.3 |
C10—C11—C7 | 121.97 (18) | O19—C18—H182 | 109.3 |
C12—C11—C7 | 121.79 (19) | C17—C18—H182 | 109.3 |
C13—C12—C11 | 122.2 (2) | H181—C18—H182 | 108.0 |
C13—C12—H12 | 118.9 | C18—O19—C20 | 109.9 (3) |
C11—C12—H12 | 118.9 | O19—C20—C21 | 112.6 (4) |
C12—C13—C14 | 119.5 (2) | O19—C20—H201 | 109.1 |
C12—C13—H13 | 120.3 | C21—C20—H201 | 109.1 |
C14—C13—H13 | 120.3 | O19—C20—H202 | 109.1 |
O1—C14—C15 | 116.6 (2) | C21—C20—H202 | 109.1 |
O1—C14—C13 | 123.34 (19) | H201—C20—H202 | 107.8 |
C15—C14—C13 | 120.01 (19) | O16—C21—C20 | 110.2 (4) |
C11—C10—C15 | 123.07 (18) | O16—C21—H211 | 109.6 |
C11—C10—O2 | 122.57 (17) | C20—C21—H211 | 109.6 |
C15—C10—O2 | 114.36 (18) | O16—C21—H212 | 109.6 |
C14—C15—C10 | 119.0 (2) | C20—C21—H212 | 109.6 |
C14—C15—H15 | 120.5 | H211—C21—H212 | 108.1 |
| | | |
C2—C3—C4—C5 | 0.4 (4) | C11—C10—C15—C14 | −1.1 (3) |
Cl1—C3—C4—C5 | −179.8 (2) | O2—C10—C15—C14 | 178.35 (18) |
C3—C4—C5—C6 | −0.3 (4) | C10—O2—C9—N2 | 173.17 (18) |
C4—C5—C6—C1 | 0.0 (3) | C10—O2—C9—C8 | −7.7 (3) |
C4—C5—C6—C7 | −178.7 (2) | N2—C9—C8—C22 | −3.7 (3) |
C5—C6—C7—C11 | 102.8 (2) | O2—C9—C8—C22 | 177.2 (2) |
C1—C6—C7—C11 | −75.9 (2) | N2—C9—C8—C7 | 178.9 (2) |
C5—C6—C7—C8 | −134.0 (2) | O2—C9—C8—C7 | −0.1 (3) |
C1—C6—C7—C8 | 47.3 (3) | C11—C7—C8—C9 | 7.6 (3) |
C8—C7—C11—C10 | −8.1 (2) | C6—C7—C8—C9 | −116.9 (2) |
C6—C7—C11—C10 | 117.2 (2) | C11—C7—C8—C22 | −169.73 (19) |
C8—C7—C11—C12 | 172.12 (18) | C6—C7—C8—C22 | 65.8 (2) |
C6—C7—C11—C12 | −62.5 (2) | C5—C6—C1—C2 | 0.2 (3) |
C10—C11—C12—C13 | 0.5 (3) | C7—C6—C1—C2 | 178.92 (19) |
C7—C11—C12—C13 | −179.75 (19) | C4—C3—C2—C1 | −0.2 (4) |
C11—C12—C13—C14 | −1.4 (3) | Cl1—C3—C2—C1 | 179.98 (18) |
C12—C13—C14—O1 | 179.6 (2) | C4—C3—C2—Cl2 | 179.7 (2) |
C12—C13—C14—C15 | 1.1 (3) | Cl1—C3—C2—Cl2 | −0.1 (3) |
C12—C11—C10—C15 | 0.8 (3) | C6—C1—C2—C3 | −0.1 (3) |
C7—C11—C10—C15 | −178.98 (18) | C6—C1—C2—Cl2 | 179.97 (16) |
C12—C11—C10—O2 | −178.63 (18) | C21—O16—C17—C18 | −56.6 (5) |
C7—C11—C10—O2 | 1.6 (3) | O16—C17—C18—O19 | 57.7 (5) |
C9—O2—C10—C11 | 6.9 (3) | C17—C18—O19—C20 | −56.0 (5) |
C9—O2—C10—C15 | −172.56 (18) | C18—O19—C20—C21 | 55.8 (6) |
O1—C14—C15—C10 | −178.52 (19) | C17—O16—C21—C20 | 55.5 (5) |
C13—C14—C15—C10 | 0.1 (3) | O19—C20—C21—O16 | −55.7 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—HO1···O16 | 0.82 | 1.85 | 2.658 (3) | 167 |
N2—HNB···O1i | 0.86 | 2.19 | 2.978 (3) | 153 |
N2—HNA···N1ii | 0.86 | 2.22 | 2.989 (3) | 149 |
C4—H4···Cl2iii | 0.93 | 2.87 | 3.692 (3) | 148 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, y+1/2, −z+1/2; (iii) x, y−1, z. |
2-Amino-3-cyano-4-(2,6-dichlorophenyl)-7-hydroxy-4
H-\
benzo[1,2-
b]pyran (II)
top
Crystal data top
C16H9Cl2N2O2 | F(000) = 338 |
Mr = 332.15 | Dx = 1.548 Mg m−3 |
Triclinic, P1 | Melting point: 514 K |
a = 6.271 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.697 (5) Å | Cell parameters from 8750 reflections |
c = 13.794 (7) Å | θ = 3.1–30.4° |
α = 107.06 (2)° | µ = 0.46 mm−1 |
β = 94.269 (17)° | T = 294 K |
γ = 95.00 (3)° | Block, colourless |
V = 712.5 (7) Å3 | 0.15 × 0.15 × 0.10 mm |
Z = 2 | |
Data collection top
Bruker Kappa APEX3 CMOS diffractometer | 2499 independent reflections |
Radiation source: fine-focus sealed tube | 2239 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω and φ scan | θmax = 25.0°, θmin = 3.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2018) | h = −7→7 |
Tmin = 0.704, Tmax = 0.746 | k = −10→10 |
22289 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.033 | H 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 reflections | Δρmax = 0.23 e Å−3 |
204 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.84692 (8) | 0.84534 (6) | 0.32241 (4) | 0.04703 (19) | |
Cl2 | 0.10752 (8) | 0.50064 (7) | 0.36100 (4) | 0.0536 (2) | |
O1 | 1.0482 (2) | 0.15972 (18) | 0.09764 (12) | 0.0484 (4) | |
HO1 | 1.058 (5) | 0.092 (4) | 0.130 (2) | 0.084 (10)* | |
O2 | 0.7394 (2) | 0.62001 (14) | 0.07971 (9) | 0.0331 (3) | |
N1 | 0.1786 (3) | 0.9314 (2) | 0.18547 (15) | 0.0538 (5) | |
N2 | 0.6119 (3) | 0.83118 (18) | 0.04811 (12) | 0.0372 (4) | |
HNB | 0.7128 | 0.8266 | 0.0087 | 0.045* | |
HNA | 0.5262 | 0.9046 | 0.0540 | 0.045* | |
C14 | 0.8930 (3) | 0.2578 (2) | 0.12922 (13) | 0.0314 (4) | |
C13 | 0.7476 (3) | 0.2339 (2) | 0.19616 (13) | 0.0327 (4) | |
H13 | 0.7498 | 0.1452 | 0.2207 | 0.039* | |
C12 | 0.6001 (3) | 0.3428 (2) | 0.22588 (13) | 0.0303 (4) | |
H12 | 0.5033 | 0.3258 | 0.2706 | 0.036* | |
C11 | 0.5912 (3) | 0.47743 (19) | 0.19116 (12) | 0.0252 (4) | |
C7 | 0.4337 (3) | 0.59914 (19) | 0.22777 (12) | 0.0244 (3) | |
H7 | 0.2892 | 0.5394 | 0.2131 | 0.029* | |
C6 | 0.4733 (3) | 0.67923 (19) | 0.34378 (12) | 0.0256 (4) | |
C1 | 0.3324 (3) | 0.6415 (2) | 0.40945 (13) | 0.0340 (4) | |
C2 | 0.3630 (4) | 0.7086 (3) | 0.51432 (15) | 0.0489 (5) | |
H2 | 0.2637 | 0.6808 | 0.5549 | 0.059* | |
C3 | 0.5406 (4) | 0.8159 (3) | 0.55754 (15) | 0.0545 (6) | |
H3 | 0.5623 | 0.8621 | 0.6280 | 0.065* | |
C8 | 0.4401 (3) | 0.7173 (2) | 0.16603 (12) | 0.0272 (4) | |
C22 | 0.2927 (3) | 0.8338 (2) | 0.17803 (13) | 0.0333 (4) | |
C9 | 0.5883 (3) | 0.72374 (19) | 0.10034 (12) | 0.0270 (4) | |
C10 | 0.7341 (3) | 0.49354 (19) | 0.12257 (12) | 0.0258 (4) | |
C15 | 0.8841 (3) | 0.3873 (2) | 0.09093 (13) | 0.0306 (4) | |
H15 | 0.9778 | 0.4028 | 0.0446 | 0.037* | |
C4 | 0.6873 (4) | 0.8561 (3) | 0.49742 (15) | 0.0482 (5) | |
H4 | 0.8094 | 0.9282 | 0.5269 | 0.058* | |
C5 | 0.6524 (3) | 0.7886 (2) | 0.39261 (13) | 0.0333 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0390 (3) | 0.0566 (3) | 0.0404 (3) | −0.0157 (2) | 0.0042 (2) | 0.0129 (2) |
Cl2 | 0.0435 (3) | 0.0712 (4) | 0.0448 (3) | −0.0174 (2) | 0.0084 (2) | 0.0216 (3) |
O1 | 0.0615 (10) | 0.0440 (8) | 0.0580 (9) | 0.0319 (7) | 0.0295 (7) | 0.0303 (7) |
O2 | 0.0421 (7) | 0.0305 (6) | 0.0376 (7) | 0.0150 (5) | 0.0189 (5) | 0.0204 (5) |
N1 | 0.0546 (11) | 0.0603 (12) | 0.0685 (12) | 0.0324 (10) | 0.0294 (9) | 0.0405 (10) |
N2 | 0.0469 (9) | 0.0356 (8) | 0.0409 (9) | 0.0166 (7) | 0.0178 (7) | 0.0231 (7) |
C14 | 0.0388 (10) | 0.0269 (8) | 0.0303 (9) | 0.0110 (7) | 0.0057 (7) | 0.0088 (7) |
C13 | 0.0433 (10) | 0.0254 (8) | 0.0340 (9) | 0.0057 (7) | 0.0052 (8) | 0.0154 (7) |
C12 | 0.0362 (9) | 0.0298 (9) | 0.0276 (8) | 0.0013 (7) | 0.0063 (7) | 0.0128 (7) |
C11 | 0.0289 (8) | 0.0243 (8) | 0.0222 (8) | 0.0023 (6) | 0.0012 (6) | 0.0071 (6) |
C7 | 0.0235 (8) | 0.0264 (8) | 0.0242 (8) | 0.0026 (6) | 0.0033 (6) | 0.0090 (6) |
C6 | 0.0285 (8) | 0.0259 (8) | 0.0247 (8) | 0.0063 (7) | 0.0043 (6) | 0.0098 (7) |
C1 | 0.0354 (10) | 0.0376 (10) | 0.0314 (9) | 0.0017 (8) | 0.0065 (7) | 0.0139 (8) |
C2 | 0.0648 (14) | 0.0541 (12) | 0.0293 (10) | −0.0009 (11) | 0.0165 (9) | 0.0143 (9) |
C3 | 0.0846 (17) | 0.0510 (13) | 0.0232 (9) | −0.0059 (12) | 0.0054 (10) | 0.0076 (9) |
C8 | 0.0309 (9) | 0.0284 (8) | 0.0249 (8) | 0.0082 (7) | 0.0036 (7) | 0.0107 (7) |
C22 | 0.0358 (9) | 0.0374 (10) | 0.0341 (9) | 0.0099 (8) | 0.0097 (7) | 0.0191 (8) |
C9 | 0.0325 (9) | 0.0252 (8) | 0.0255 (8) | 0.0085 (7) | 0.0032 (7) | 0.0094 (7) |
C10 | 0.0328 (9) | 0.0232 (8) | 0.0248 (8) | 0.0055 (7) | 0.0043 (7) | 0.0113 (6) |
C15 | 0.0362 (9) | 0.0304 (9) | 0.0299 (9) | 0.0092 (7) | 0.0109 (7) | 0.0130 (7) |
C4 | 0.0604 (13) | 0.0444 (11) | 0.0323 (10) | −0.0108 (10) | −0.0050 (9) | 0.0073 (9) |
C5 | 0.0375 (10) | 0.0336 (9) | 0.0298 (9) | 0.0002 (7) | 0.0057 (7) | 0.0118 (7) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.7383 (19) | C11—C7 | 1.515 (2) |
Cl2—C1 | 1.736 (2) | C7—C8 | 1.515 (2) |
O1—C14 | 1.362 (2) | C7—C6 | 1.538 (2) |
O1—HO1 | 0.85 (3) | C7—H7 | 0.9800 |
O2—C9 | 1.353 (2) | C6—C5 | 1.394 (3) |
O2—C10 | 1.392 (2) | C6—C1 | 1.397 (2) |
N1—C22 | 1.144 (2) | C1—C2 | 1.383 (3) |
N2—C9 | 1.342 (2) | C2—C3 | 1.364 (3) |
N2—HNB | 0.8600 | C2—H2 | 0.9300 |
N2—HNA | 0.8600 | C3—C4 | 1.373 (3) |
C14—C15 | 1.381 (2) | C3—H3 | 0.9300 |
C14—C13 | 1.390 (3) | C8—C9 | 1.354 (2) |
C13—C12 | 1.380 (3) | C8—C22 | 1.413 (2) |
C13—H13 | 0.9300 | C10—C15 | 1.380 (2) |
C12—C11 | 1.392 (2) | C15—H15 | 0.9300 |
C12—H12 | 0.9300 | C4—C5 | 1.384 (3) |
C11—C10 | 1.378 (2) | C4—H4 | 0.9300 |
| | | |
C14—O1—HO1 | 112 (2) | C2—C1—Cl2 | 116.30 (15) |
C9—O2—C10 | 118.64 (13) | C6—C1—Cl2 | 120.20 (14) |
C9—N2—HNB | 120.0 | C3—C2—C1 | 119.25 (19) |
C9—N2—HNA | 120.0 | C3—C2—H2 | 120.4 |
HNB—N2—HNA | 120.0 | C1—C2—H2 | 120.4 |
O1—C14—C15 | 116.39 (16) | C2—C3—C4 | 120.18 (19) |
O1—C14—C13 | 123.88 (16) | C2—C3—H3 | 119.9 |
C15—C14—C13 | 119.73 (16) | C4—C3—H3 | 119.9 |
C12—C13—C14 | 119.48 (15) | C9—C8—C22 | 115.95 (15) |
C12—C13—H13 | 120.3 | C9—C8—C7 | 123.49 (14) |
C14—C13—H13 | 120.3 | C22—C8—C7 | 120.51 (15) |
C13—C12—C11 | 122.22 (16) | N1—C22—C8 | 177.10 (19) |
C13—C12—H12 | 118.9 | N2—C9—O2 | 110.03 (14) |
C11—C12—H12 | 118.9 | N2—C9—C8 | 126.71 (15) |
C10—C11—C12 | 116.26 (15) | O2—C9—C8 | 123.25 (15) |
C10—C11—C7 | 122.30 (14) | C11—C10—C15 | 123.29 (15) |
C12—C11—C7 | 121.44 (15) | C11—C10—O2 | 122.40 (14) |
C11—C7—C8 | 109.10 (13) | C15—C10—O2 | 114.31 (14) |
C11—C7—C6 | 111.28 (13) | C10—C15—C14 | 118.96 (16) |
C8—C7—C6 | 114.32 (14) | C10—C15—H15 | 120.5 |
C11—C7—H7 | 107.3 | C14—C15—H15 | 120.5 |
C8—C7—H7 | 107.3 | C3—C4—C5 | 119.6 (2) |
C6—C7—H7 | 107.3 | C3—C4—H4 | 120.2 |
C5—C6—C1 | 114.50 (15) | C5—C4—H4 | 120.2 |
C5—C6—C7 | 124.05 (14) | C4—C5—C6 | 123.02 (17) |
C1—C6—C7 | 121.41 (15) | C4—C5—Cl1 | 116.49 (15) |
C2—C1—C6 | 123.48 (18) | C6—C5—Cl1 | 120.49 (13) |
| | | |
O1—C14—C13—C12 | 178.13 (17) | C10—O2—C9—N2 | −176.56 (14) |
C15—C14—C13—C12 | −1.9 (3) | C10—O2—C9—C8 | 4.5 (2) |
C14—C13—C12—C11 | −0.1 (3) | C22—C8—C9—N2 | 1.8 (3) |
C13—C12—C11—C10 | 2.0 (2) | C7—C8—C9—N2 | −175.57 (16) |
C13—C12—C11—C7 | −177.63 (15) | C22—C8—C9—O2 | −179.42 (15) |
C10—C11—C7—C8 | 8.4 (2) | C7—C8—C9—O2 | 3.2 (3) |
C12—C11—C7—C8 | −172.08 (15) | C12—C11—C10—C15 | −2.0 (2) |
C10—C11—C7—C6 | −118.71 (17) | C7—C11—C10—C15 | 177.61 (15) |
C12—C11—C7—C6 | 60.9 (2) | C12—C11—C10—O2 | 178.39 (15) |
C11—C7—C6—C5 | 70.1 (2) | C7—C11—C10—O2 | −2.0 (2) |
C8—C7—C6—C5 | −54.1 (2) | C9—O2—C10—C11 | −5.0 (2) |
C11—C7—C6—C1 | −107.41 (18) | C9—O2—C10—C15 | 175.30 (15) |
C8—C7—C6—C1 | 128.44 (17) | C11—C10—C15—C14 | 0.1 (3) |
C5—C6—C1—C2 | 1.3 (3) | O2—C10—C15—C14 | 179.77 (15) |
C7—C6—C1—C2 | 179.01 (18) | O1—C14—C15—C10 | −178.14 (16) |
C5—C6—C1—Cl2 | −177.27 (13) | C13—C14—C15—C10 | 1.9 (3) |
C7—C6—C1—Cl2 | 0.4 (2) | C2—C3—C4—C5 | 0.9 (4) |
C6—C1—C2—C3 | −0.9 (3) | C3—C4—C5—C6 | −0.3 (3) |
Cl2—C1—C2—C3 | 177.78 (18) | C3—C4—C5—Cl1 | −179.69 (18) |
C1—C2—C3—C4 | −0.3 (4) | C1—C6—C5—C4 | −0.7 (3) |
C11—C7—C8—C9 | −9.1 (2) | C7—C6—C5—C4 | −178.35 (17) |
C6—C7—C8—C9 | 116.24 (18) | C1—C6—C5—Cl1 | 178.63 (13) |
C11—C7—C8—C22 | 173.69 (15) | C7—C6—C5—Cl1 | 1.0 (2) |
C6—C7—C8—C22 | −61.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cl2 | 0.98 | 2.50 | 3.078 (3) | 117 |
N2—HNB···O1i | 0.86 | 2.19 | 3.048 (2) | 173 |
O1—HO1···N1ii | 0.85 (3) | 1.95 (3) | 2.762 (2) | 160 (3) |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y−1, z. |