2-(2-Chloro­benzo­yl)-1-(3,4-di­meth­oxy­phen­yl)-3-iodo­quinolin-4(1H)-one

In the title compound C₂₄H₁₇ClINO₄, the iodo­quinolinyl moiety (r.m.s. deviation = 0.044 Å) makes dihedral angles of 87.44 (10) and 88.64 (10)° with the chloro- and meth­oxy-substituted benzene rings, respectively. The meth­oxy groups are present in synperiplanar and anti­periplanar conformations with respect to the benzene ring they are bound to, as indicated by the C—C—O—C torsion angle values of −16.2 (3) and 177.6 (2)°, respectively. The crystal structure features relatively strong meth­oxy­benzene-C—H...O(quinolin­yl) hydrogen bonds, leading to helical supra­molecular chains along the a-axis direction. Additional C—H...O inter­actions along with π-stacking [inter-centroid distance = 3.6070 (16) Å between quinolyl-NC₅ and C₆ rings] consolidate the three-dimensional mol­ecular packing.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.024
• wR factor = 0.060
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT369_ALERT_2_C Long    C(sp2)-C(sp2) Bond  C9     -   C18    ..       1.53 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C24 H17 Cl I N O4
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       6.39 Why ?
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          84 % Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

2-(2-Chlorobenzoyl)-1-(3,4-dimethoxyphenyl)-3-iodoquinolin-4(1H)-one

Crystal data

C24H17ClINO4	F(000) = 2160
Mr = 545.74	Dx = 1.648 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3874 reflections
a = 8.7884 (19) Å	θ = 2.5–25.0°
b = 16.863 (3) Å	µ = 1.61 mm^−1
c = 29.686 (6) Å	T = 296 K
V = 4399.4 (15) Å^3	Block, light-yellow
Z = 8	0.28 × 0.25 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	3593 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.046
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
Detector resolution: 18.4 pixels mm^-1	h = −10→10
ω and φ scans	k = −20→19
56765 measured reflections	l = −35→35
3874 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0219P)^2 + 6.3895P] where P = (Fo^2 + 2Fc^2)/3
3874 reflections	(Δ/σ)max = 0.004
282 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all 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 observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq
I1	−0.39094 (2)	1.04870 (1)	0.21059 (1)	0.0231 (1)
Cl1	−0.27999 (11)	1.03024 (5)	0.03373 (2)	0.0477 (3)
O1	0.1757 (2)	0.74428 (11)	0.01813 (5)	0.0259 (5)
O2	0.29338 (19)	0.86211 (10)	0.06210 (5)	0.0236 (5)
O3	−0.2765 (2)	0.94436 (11)	0.29303 (5)	0.0272 (6)
O4	−0.3203 (2)	0.91957 (11)	0.10683 (6)	0.0261 (6)
N1	−0.1004 (2)	0.84994 (11)	0.17668 (6)	0.0153 (5)
C1	0.1169 (3)	0.67708 (18)	−0.00627 (10)	0.0376 (10)
C2	0.0991 (3)	0.76620 (15)	0.05630 (8)	0.0213 (7)
C3	0.1650 (3)	0.83057 (14)	0.08001 (8)	0.0179 (7)
C4	0.0980 (3)	0.85657 (14)	0.11953 (7)	0.0169 (7)
C5	−0.0345 (3)	0.82028 (14)	0.13488 (8)	0.0180 (7)
C6	−0.1004 (3)	0.75814 (16)	0.11208 (9)	0.0253 (8)
C7	−0.0321 (3)	0.73079 (15)	0.07250 (9)	0.0269 (8)
C8	0.3381 (3)	0.93844 (16)	0.07906 (8)	0.0258 (8)
C9	−0.1894 (2)	0.91661 (13)	0.17572 (7)	0.0134 (6)
C10	−0.2502 (3)	0.94889 (13)	0.21374 (7)	0.0158 (7)
C11	−0.2200 (3)	0.91699 (14)	0.25809 (8)	0.0185 (7)
C12	−0.1132 (3)	0.84990 (15)	0.25812 (8)	0.0195 (7)
C13	−0.0577 (3)	0.81681 (14)	0.21792 (8)	0.0173 (7)
C14	0.0431 (3)	0.75209 (15)	0.21921 (9)	0.0237 (8)
C15	0.0889 (3)	0.72195 (16)	0.26027 (10)	0.0317 (9)
C16	0.0356 (3)	0.75544 (18)	0.30039 (10)	0.0332 (9)
C17	−0.0641 (3)	0.81755 (17)	0.29940 (9)	0.0273 (8)
C18	−0.2210 (3)	0.95053 (13)	0.12885 (7)	0.0168 (7)
C19	−0.1243 (3)	1.01877 (14)	0.11448 (8)	0.0181 (7)
C20	−0.0077 (3)	1.04505 (14)	0.14276 (8)	0.0203 (7)
C21	0.0893 (3)	1.10621 (16)	0.13033 (9)	0.0289 (8)
C22	0.0687 (4)	1.14313 (17)	0.08892 (10)	0.0389 (10)
C23	−0.0457 (4)	1.11858 (17)	0.06040 (9)	0.0404 (10)
C24	−0.1404 (3)	1.05705 (15)	0.07267 (9)	0.0287 (9)
H0AA	0.11530	0.63150	0.01310	0.0560*
H0AB	0.18070	0.66650	−0.03180	0.0560*
H0AC	0.01540	0.68840	−0.01630	0.0560*
H4	0.14130	0.89800	0.13570	0.0200*
H9	0.00530	1.02090	0.17070	0.0240*
H10	0.16710	1.12230	0.14950	0.0350*
H11	0.13240	1.18460	0.08040	0.0470*
H12A	0.25530	0.97510	0.07580	0.0390*
H12B	0.42450	0.95730	0.06240	0.0390*
H12C	0.36450	0.93390	0.11030	0.0390*
H17	0.07860	0.72970	0.19260	0.0280*
H18	0.15560	0.67920	0.26130	0.0380*
H19	0.06820	0.73530	0.32790	0.0400*
H20	−0.10010	0.83870	0.32630	0.0330*
H21	−0.05910	1.14360	0.03280	0.0480*
H23	−0.18900	0.73470	0.12280	0.0300*
H24	−0.07510	0.68850	0.05690	0.0320*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0177 (1)	0.0161 (1)	0.0353 (1)	0.0008 (1)	0.0069 (1)	−0.0030 (1)
Cl1	0.0770 (6)	0.0408 (4)	0.0252 (3)	−0.0120 (4)	−0.0219 (4)	0.0116 (3)
O1	0.0287 (10)	0.0306 (10)	0.0183 (8)	0.0073 (8)	−0.0009 (7)	−0.0131 (7)
O2	0.0202 (9)	0.0291 (9)	0.0215 (8)	0.0003 (8)	0.0054 (7)	−0.0056 (7)
O3	0.0298 (11)	0.0336 (11)	0.0182 (9)	−0.0089 (8)	0.0098 (7)	−0.0048 (7)
O4	0.0249 (10)	0.0317 (10)	0.0218 (9)	−0.0061 (8)	−0.0079 (8)	0.0022 (8)
N1	0.0142 (10)	0.0157 (9)	0.0159 (9)	0.0000 (8)	0.0011 (7)	−0.0008 (8)
C1	0.0441 (18)	0.0394 (17)	0.0294 (15)	0.0029 (14)	−0.0004 (13)	−0.0220 (13)
C2	0.0197 (13)	0.0261 (13)	0.0181 (12)	0.0090 (10)	−0.0037 (10)	−0.0087 (10)
C3	0.0138 (12)	0.0216 (12)	0.0182 (11)	0.0042 (10)	−0.0027 (9)	−0.0014 (9)
C4	0.0153 (12)	0.0201 (12)	0.0152 (11)	0.0029 (9)	−0.0041 (9)	−0.0036 (9)
C5	0.0157 (12)	0.0195 (12)	0.0187 (11)	0.0039 (9)	0.0004 (9)	−0.0041 (9)
C6	0.0179 (13)	0.0262 (13)	0.0318 (14)	−0.0028 (11)	0.0021 (11)	−0.0088 (11)
C7	0.0234 (14)	0.0255 (14)	0.0318 (14)	−0.0003 (11)	−0.0036 (11)	−0.0164 (11)
C8	0.0233 (13)	0.0341 (15)	0.0201 (12)	−0.0065 (12)	0.0023 (11)	−0.0030 (11)
C9	0.0122 (11)	0.0122 (10)	0.0158 (11)	−0.0031 (9)	−0.0009 (9)	0.0002 (9)
C10	0.0136 (12)	0.0138 (11)	0.0199 (12)	−0.0024 (9)	0.0014 (9)	−0.0004 (9)
C11	0.0163 (12)	0.0208 (12)	0.0185 (12)	−0.0102 (10)	0.0030 (9)	−0.0013 (10)
C12	0.0171 (12)	0.0217 (12)	0.0198 (12)	−0.0099 (10)	−0.0010 (9)	0.0057 (10)
C13	0.0128 (11)	0.0160 (12)	0.0230 (12)	−0.0069 (10)	−0.0031 (10)	0.0044 (9)
C14	0.0179 (13)	0.0174 (12)	0.0358 (14)	−0.0045 (10)	−0.0044 (11)	0.0030 (10)
C15	0.0202 (13)	0.0206 (13)	0.0544 (19)	−0.0074 (11)	−0.0128 (12)	0.0150 (13)
C16	0.0273 (15)	0.0382 (16)	0.0342 (15)	−0.0153 (13)	−0.0141 (12)	0.0221 (13)
C17	0.0220 (14)	0.0385 (16)	0.0214 (12)	−0.0128 (12)	−0.0035 (11)	0.0110 (11)
C18	0.0172 (12)	0.0184 (12)	0.0149 (11)	0.0029 (10)	0.0005 (9)	−0.0016 (9)
C19	0.0223 (13)	0.0156 (11)	0.0163 (11)	0.0027 (10)	0.0034 (9)	−0.0007 (9)
C20	0.0197 (12)	0.0190 (12)	0.0221 (12)	0.0014 (10)	0.0037 (10)	−0.0001 (10)
C21	0.0255 (14)	0.0256 (14)	0.0355 (15)	−0.0066 (11)	0.0096 (12)	−0.0070 (12)
C22	0.0500 (19)	0.0256 (14)	0.0411 (17)	−0.0143 (14)	0.0201 (15)	0.0021 (13)
C23	0.069 (2)	0.0289 (15)	0.0234 (14)	−0.0103 (15)	0.0088 (15)	0.0075 (12)
C24	0.0431 (17)	0.0231 (14)	0.0199 (13)	−0.0010 (12)	−0.0008 (12)	0.0009 (10)

Geometric parameters (Å, º)

I1—C10	2.091 (2)	C16—C17	1.366 (4)
Cl1—C24	1.745 (3)	C18—C19	1.493 (3)
O1—C1	1.441 (3)	C19—C20	1.397 (4)
O1—C2	1.369 (3)	C19—C24	1.406 (4)
O2—C3	1.356 (3)	C20—C21	1.388 (4)
O2—C8	1.437 (3)	C21—C22	1.390 (4)
O3—C11	1.239 (3)	C22—C23	1.378 (5)
O4—C18	1.209 (3)	C23—C24	1.379 (4)
N1—C5	1.458 (3)	C1—H0AA	0.9600
N1—C9	1.370 (3)	C1—H0AB	0.9600
N1—C13	1.397 (3)	C1—H0AC	0.9600
C2—C3	1.417 (3)	C4—H4	0.9300
C2—C7	1.385 (4)	C6—H23	0.9300
C3—C4	1.384 (3)	C7—H24	0.9300
C4—C5	1.392 (4)	C8—H12A	0.9600
C5—C6	1.375 (4)	C8—H12B	0.9600
C6—C7	1.398 (4)	C8—H12C	0.9600
C9—C10	1.362 (3)	C14—H17	0.9300
C9—C18	1.530 (3)	C15—H18	0.9300
C10—C11	1.447 (3)	C16—H19	0.9300
C11—C12	1.470 (4)	C17—H20	0.9300
C12—C13	1.405 (3)	C20—H9	0.9300
C12—C17	1.409 (4)	C21—H10	0.9300
C13—C14	1.406 (4)	C22—H11	0.9300
C14—C15	1.381 (4)	C23—H21	0.9300
C15—C16	1.399 (4)
C1—O1—C2	116.9 (2)	C19—C20—C21	121.8 (2)
C3—O2—C8	116.20 (18)	C20—C21—C22	119.2 (3)
C5—N1—C9	119.39 (18)	C21—C22—C23	120.3 (3)
C5—N1—C13	120.13 (19)	C22—C23—C24	120.3 (3)
C9—N1—C13	119.99 (18)	Cl1—C24—C19	122.4 (2)
O1—C2—C3	114.6 (2)	Cl1—C24—C23	116.4 (2)
O1—C2—C7	125.5 (2)	C19—C24—C23	121.2 (2)
C3—C2—C7	119.9 (2)	O1—C1—H0AA	110.00
O2—C3—C2	116.5 (2)	O1—C1—H0AB	109.00
O2—C3—C4	124.2 (2)	O1—C1—H0AC	109.00
C2—C3—C4	119.3 (2)	H0AA—C1—H0AB	109.00
C3—C4—C5	119.6 (2)	H0AA—C1—H0AC	109.00
N1—C5—C4	117.4 (2)	H0AB—C1—H0AC	110.00
N1—C5—C6	120.9 (2)	C3—C4—H4	120.00
C4—C5—C6	121.7 (2)	C5—C4—H4	120.00
C5—C6—C7	119.0 (2)	C5—C6—H23	121.00
C2—C7—C6	120.5 (2)	C7—C6—H23	120.00
N1—C9—C10	122.3 (2)	C2—C7—H24	120.00
N1—C9—C18	115.43 (18)	C6—C7—H24	120.00
C10—C9—C18	122.21 (19)	O2—C8—H12A	110.00
I1—C10—C9	121.11 (16)	O2—C8—H12B	109.00
I1—C10—C11	116.65 (16)	O2—C8—H12C	109.00
C9—C10—C11	122.2 (2)	H12A—C8—H12B	110.00
O3—C11—C10	123.4 (2)	H12A—C8—H12C	109.00
O3—C11—C12	122.8 (2)	H12B—C8—H12C	109.00
C10—C11—C12	113.8 (2)	C13—C14—H17	120.00
C11—C12—C13	121.8 (2)	C15—C14—H17	120.00
C11—C12—C17	119.6 (2)	C14—C15—H18	120.00
C13—C12—C17	118.6 (2)	C16—C15—H18	120.00
N1—C13—C12	119.5 (2)	C15—C16—H19	120.00
N1—C13—C14	120.2 (2)	C17—C16—H19	120.00
C12—C13—C14	120.3 (2)	C12—C17—H20	120.00
C13—C14—C15	119.6 (2)	C16—C17—H20	120.00
C14—C15—C16	120.4 (2)	C19—C20—H9	119.00
C15—C16—C17	120.4 (3)	C21—C20—H9	119.00
C12—C17—C16	120.8 (3)	C20—C21—H10	120.00
O4—C18—C9	117.5 (2)	C22—C21—H10	120.00
O4—C18—C19	126.1 (2)	C21—C22—H11	120.00
C9—C18—C19	116.41 (19)	C23—C22—H11	120.00
C18—C19—C20	119.4 (2)	C22—C23—H21	120.00
C18—C19—C24	123.3 (2)	C24—C23—H21	120.00
C20—C19—C24	117.3 (2)
C1—O1—C2—C3	177.6 (2)	C10—C9—C18—C19	83.6 (3)
C1—O1—C2—C7	−2.1 (4)	I1—C10—C11—O3	2.2 (3)
C8—O2—C3—C2	164.8 (2)	I1—C10—C11—C12	−176.55 (17)
C8—O2—C3—C4	−16.2 (3)	C9—C10—C11—O3	−178.5 (2)
C9—N1—C5—C4	81.4 (3)	C9—C10—C11—C12	2.8 (3)
C9—N1—C5—C6	−99.5 (3)	O3—C11—C12—C13	176.1 (2)
C13—N1—C5—C4	−90.5 (3)	O3—C11—C12—C17	−4.1 (4)
C13—N1—C5—C6	88.6 (3)	C10—C11—C12—C13	−5.1 (4)
C5—N1—C9—C10	−177.8 (2)	C10—C11—C12—C17	174.7 (2)
C5—N1—C9—C18	4.5 (3)	C11—C12—C13—N1	2.3 (4)
C13—N1—C9—C10	−5.9 (3)	C11—C12—C13—C14	−179.3 (2)
C13—N1—C9—C18	176.4 (2)	C17—C12—C13—N1	−177.6 (2)
C5—N1—C13—C12	175.2 (2)	C17—C12—C13—C14	0.8 (4)
C5—N1—C13—C14	−3.2 (3)	C11—C12—C17—C16	−179.7 (3)
C9—N1—C13—C12	3.3 (3)	C13—C12—C17—C16	0.1 (4)
C9—N1—C13—C14	−175.1 (2)	N1—C13—C14—C15	177.5 (2)
O1—C2—C3—O2	0.3 (3)	C12—C13—C14—C15	−0.9 (4)
O1—C2—C3—C4	−178.9 (2)	C13—C14—C15—C16	0.0 (4)
C7—C2—C3—O2	180.0 (2)	C14—C15—C16—C17	1.0 (4)
C7—C2—C3—C4	0.8 (4)	C15—C16—C17—C12	−1.1 (4)
O1—C2—C7—C6	179.8 (2)	O4—C18—C19—C20	−176.2 (2)
C3—C2—C7—C6	0.1 (4)	O4—C18—C19—C24	1.4 (4)
O2—C3—C4—C5	179.7 (2)	C9—C18—C19—C20	3.2 (3)
C2—C3—C4—C5	−1.3 (4)	C9—C18—C19—C24	−179.2 (2)
C3—C4—C5—N1	180.0 (2)	C18—C19—C20—C21	177.5 (2)
C3—C4—C5—C6	0.9 (4)	C24—C19—C20—C21	−0.3 (4)
N1—C5—C6—C7	−179.0 (2)	C18—C19—C24—Cl1	2.0 (4)
C4—C5—C6—C7	0.1 (4)	C18—C19—C24—C23	−178.3 (3)
C5—C6—C7—C2	−0.6 (4)	C20—C19—C24—Cl1	179.58 (19)
N1—C9—C10—I1	−178.10 (15)	C20—C19—C24—C23	−0.7 (4)
N1—C9—C10—C11	2.6 (3)	C19—C20—C21—C22	0.9 (4)
C18—C9—C10—I1	−0.5 (3)	C20—C21—C22—C23	−0.7 (4)
C18—C9—C10—C11	−179.8 (2)	C21—C22—C23—C24	−0.2 (5)
N1—C9—C18—O4	80.7 (3)	C22—C23—C24—Cl1	−179.4 (2)
N1—C9—C18—C19	−98.7 (2)	C22—C23—C24—C19	0.9 (4)
C10—C9—C18—O4	−97.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H0AC···O2^i	0.96	2.53	3.357 (3)	145
C4—H4···O3^ii	0.93	2.37	3.185 (3)	147
C20—H9···O3^ii	0.93	2.55	3.263 (3)	134

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, y, −z+1/2.