Crystal structures of two new carbazole derivatives: ethyl 9-(benzene­sulfon­yl)-2-(4-fluoro-2-nitro­phen­yl)-6-meth­oxy-9H-carbazole-3-carboxyl­ate and 12-(benzene­sulfon­yl)-12H-quinolino­[4,3-b]carbazole

The crystal structures of two benzene­sulfonyl-carbazole derivatives are described and the inter­molecular contacts in the crystals analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.150
• Data-to-parameter ratio = 14.7

Structure: II

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.161
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT431_ALERT_2_C Short Inter HL..A Contact  F1       ..O2       .       2.88 Ang.
                                                   x,-1+y,z  =      1_545 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.362 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=    0.600          9 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          8 Note
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       53.0 Degree
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
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00433 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.591 Report
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT480_ALERT_4_G Long H...A H-Bond Reported H21      ..N2       .       2.64 Ang.
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          7 Note
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       54.0 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: APEX3/SAINT (Bruker, 2016); data reduction: SAINT/XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2020).

Ethyl 9-(benzenesulfonyl)-2-(4-fluoro-2-nitrophenyl)-6-methoxy-9H-carbazole-3-carboxylate (I)

Crystal data

C28H21FN2O7S	Z = 2
Mr = 548.53	F(000) = 568
Triclinic, P1	Dx = 1.450 Mg m^−3
a = 8.1589 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2053 (13) Å	Cell parameters from 9133 reflections
c = 12.9129 (13) Å	θ = 2.9–20.6°
α = 101.569 (4)°	µ = 0.19 mm^−1
β = 93.086 (4)°	T = 298 K
γ = 92.481 (4)°	Solid, pale yellow
V = 1256.0 (2) Å^3	0.31 × 0.24 × 0.13 mm

Data collection

Bruker D8 Venture diffractometer with Photon II detector	5194 independent reflections
Radiation source: fine-focus sealed tube	4176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω and φ scan	θmax = 26.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
Tmin = 0.923, Tmax = 0.965	k = −15→15
31739 measured reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.9577P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
5194 reflections	Δρmax = 0.28 e Å^−3
354 parameters	Δρmin = −0.38 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5947 (3)	0.82807 (19)	0.33841 (19)	0.0432 (5)
C2	0.5905 (4)	0.9424 (2)	0.3415 (2)	0.0547 (7)
H2	0.534951	0.969581	0.287941	0.066*
C3	0.6708 (4)	1.0137 (2)	0.4262 (2)	0.0602 (8)
H3	0.670280	1.090490	0.429413	0.072*
C4	0.7534 (4)	0.9746 (2)	0.5077 (2)	0.0550 (7)
C5	0.7536 (3)	0.8609 (2)	0.5069 (2)	0.0484 (6)
H5	0.805234	0.834352	0.562212	0.058*
C6	0.6741 (3)	0.78757 (18)	0.42037 (19)	0.0413 (5)
C7	0.6522 (3)	0.66650 (18)	0.39461 (18)	0.0384 (5)
C8	0.7000 (3)	0.58302 (18)	0.44653 (18)	0.0382 (5)
H8	0.760023	0.601797	0.511504	0.046*
C9	0.6584 (3)	0.47101 (18)	0.40159 (18)	0.0369 (5)
C10	0.5673 (3)	0.44179 (18)	0.30303 (18)	0.0369 (5)
C11	0.5192 (3)	0.52566 (19)	0.25104 (19)	0.0411 (5)
H11	0.458835	0.507465	0.186175	0.049*
C12	0.5621 (3)	0.63664 (18)	0.29683 (19)	0.0390 (5)
C13	0.4990 (3)	0.32669 (18)	0.25064 (17)	0.0359 (5)
C14	0.5846 (3)	0.23731 (19)	0.19937 (19)	0.0397 (5)
C15	0.5085 (3)	0.1383 (2)	0.1430 (2)	0.0461 (6)
H15	0.569368	0.080494	0.109286	0.055*
C16	0.3402 (3)	0.1284 (2)	0.1385 (2)	0.0479 (6)
C17	0.2487 (3)	0.2110 (2)	0.1896 (2)	0.0508 (6)
H17	0.134812	0.201332	0.187587	0.061*
C18	0.3288 (3)	0.3093 (2)	0.2444 (2)	0.0441 (5)
H18	0.266421	0.366080	0.278478	0.053*
C19	0.7117 (3)	0.38165 (19)	0.45764 (19)	0.0422 (5)
C20	0.6890 (3)	0.7300 (2)	0.0857 (2)	0.0506 (6)
C21	0.7943 (4)	0.8241 (3)	0.1038 (2)	0.0722 (9)
H21	0.761507	0.893146	0.138596	0.087*
C22	0.9537 (6)	0.8117 (5)	0.0674 (3)	0.1089 (18)
H22	1.029701	0.872575	0.079031	0.131*
C23	0.9955 (6)	0.7078 (7)	0.0144 (3)	0.120 (2)
H23	1.101471	0.699221	−0.008005	0.143*
C24	0.8868 (7)	0.6181 (5)	−0.0060 (3)	0.1110 (17)
H24	0.916615	0.550314	−0.045527	0.133*
C25	0.7336 (5)	0.6269 (3)	0.0313 (3)	0.0739 (9)
H25	0.660166	0.564583	0.020359	0.089*
C26	0.9088 (6)	1.0250 (3)	0.6723 (3)	0.0956 (14)
H26A	0.830154	0.991505	0.711004	0.143*
H26B	0.962806	1.089934	0.717734	0.143*
H26C	0.988796	0.971938	0.647947	0.143*
C27	0.8536 (4)	0.3375 (2)	0.6062 (2)	0.0535 (7)
H27A	0.934315	0.294924	0.565185	0.064*
H27B	0.764671	0.286048	0.616283	0.064*
C28	0.9307 (4)	0.3968 (3)	0.7108 (2)	0.0673 (8)
H28A	1.013542	0.451088	0.700178	0.101*
H28B	0.980023	0.343642	0.746679	0.101*
H28C	0.848189	0.434050	0.752872	0.101*
N1	0.5207 (3)	0.73549 (16)	0.26146 (17)	0.0445 (5)
N2	0.7653 (3)	0.2432 (2)	0.2032 (2)	0.0580 (6)
O1	0.3949 (3)	0.64184 (17)	0.08549 (17)	0.0671 (6)
O2	0.4347 (3)	0.84684 (17)	0.12977 (17)	0.0676 (6)
O3	0.8282 (3)	1.05644 (16)	0.58552 (18)	0.0792 (7)
O4	0.6862 (3)	0.28366 (15)	0.42290 (17)	0.0798 (8)
O5	0.7909 (2)	0.42120 (13)	0.55099 (14)	0.0494 (4)
O6	0.8380 (3)	0.33442 (19)	0.2187 (2)	0.0800 (7)
O7	0.8334 (3)	0.1550 (2)	0.1902 (3)	0.0957 (9)
S1	0.49241 (8)	0.73975 (5)	0.13348 (5)	0.0483 (2)
F1	0.2637 (2)	0.03387 (13)	0.08098 (16)	0.0748 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0559 (15)	0.0285 (11)	0.0468 (13)	0.0031 (10)	0.0074 (11)	0.0106 (10)
C2	0.0776 (19)	0.0340 (13)	0.0562 (16)	0.0105 (12)	0.0076 (14)	0.0156 (11)
C3	0.093 (2)	0.0257 (12)	0.0631 (17)	0.0059 (13)	0.0135 (16)	0.0100 (11)
C4	0.079 (2)	0.0314 (13)	0.0523 (15)	−0.0046 (12)	0.0100 (14)	0.0029 (11)
C5	0.0657 (17)	0.0318 (12)	0.0465 (14)	−0.0009 (11)	0.0030 (12)	0.0058 (10)
C6	0.0529 (14)	0.0288 (11)	0.0435 (13)	0.0018 (10)	0.0076 (10)	0.0096 (9)
C7	0.0481 (13)	0.0276 (11)	0.0405 (12)	0.0004 (9)	0.0048 (10)	0.0092 (9)
C8	0.0482 (13)	0.0292 (11)	0.0376 (11)	0.0007 (9)	0.0017 (10)	0.0086 (9)
C9	0.0443 (12)	0.0296 (11)	0.0385 (12)	0.0012 (9)	0.0044 (9)	0.0104 (9)
C10	0.0420 (12)	0.0292 (11)	0.0401 (12)	−0.0001 (9)	0.0052 (9)	0.0081 (9)
C11	0.0480 (13)	0.0348 (12)	0.0404 (12)	−0.0019 (10)	−0.0029 (10)	0.0099 (9)
C12	0.0456 (13)	0.0305 (11)	0.0439 (12)	0.0007 (9)	0.0023 (10)	0.0154 (9)
C13	0.0411 (12)	0.0292 (11)	0.0385 (11)	−0.0011 (9)	0.0011 (9)	0.0107 (9)
C14	0.0394 (12)	0.0350 (12)	0.0443 (12)	−0.0005 (9)	0.0022 (10)	0.0078 (9)
C15	0.0554 (15)	0.0312 (12)	0.0497 (14)	0.0025 (10)	−0.0027 (11)	0.0048 (10)
C16	0.0517 (15)	0.0316 (12)	0.0585 (15)	−0.0067 (10)	−0.0146 (12)	0.0110 (11)
C17	0.0379 (13)	0.0437 (14)	0.0729 (18)	−0.0046 (11)	−0.0077 (12)	0.0214 (13)
C18	0.0414 (13)	0.0374 (12)	0.0554 (14)	0.0046 (10)	0.0038 (11)	0.0135 (11)
C19	0.0546 (14)	0.0307 (12)	0.0427 (13)	0.0006 (10)	0.0019 (11)	0.0113 (9)
C20	0.0607 (16)	0.0537 (15)	0.0379 (13)	0.0025 (12)	−0.0091 (11)	0.0141 (11)
C21	0.074 (2)	0.091 (2)	0.0472 (16)	−0.0215 (18)	−0.0042 (15)	0.0091 (16)
C22	0.081 (3)	0.191 (5)	0.052 (2)	−0.043 (3)	−0.0110 (19)	0.033 (3)
C23	0.078 (3)	0.235 (7)	0.050 (2)	0.042 (4)	−0.001 (2)	0.035 (3)
C24	0.122 (4)	0.153 (5)	0.064 (2)	0.075 (4)	0.005 (3)	0.023 (3)
C25	0.098 (3)	0.071 (2)	0.0551 (18)	0.0295 (19)	−0.0012 (17)	0.0137 (15)
C26	0.144 (4)	0.065 (2)	0.068 (2)	−0.032 (2)	−0.022 (2)	0.0060 (18)
C27	0.0665 (17)	0.0436 (14)	0.0554 (16)	0.0101 (12)	−0.0020 (13)	0.0220 (12)
C28	0.076 (2)	0.072 (2)	0.0559 (17)	0.0126 (16)	−0.0095 (15)	0.0197 (15)
N1	0.0546 (12)	0.0305 (10)	0.0508 (12)	0.0017 (9)	−0.0021 (9)	0.0155 (9)
N2	0.0448 (13)	0.0518 (14)	0.0717 (16)	−0.0017 (11)	0.0119 (11)	−0.0023 (11)
O1	0.0753 (14)	0.0557 (12)	0.0692 (13)	−0.0174 (10)	−0.0300 (11)	0.0238 (10)
O2	0.0830 (15)	0.0528 (12)	0.0743 (14)	0.0187 (10)	−0.0081 (11)	0.0302 (10)
O3	0.128 (2)	0.0355 (10)	0.0670 (14)	−0.0149 (11)	−0.0070 (13)	0.0004 (9)
O4	0.142 (2)	0.0282 (10)	0.0659 (13)	−0.0011 (11)	−0.0335 (13)	0.0130 (9)
O5	0.0695 (12)	0.0319 (8)	0.0475 (10)	0.0026 (8)	−0.0100 (8)	0.0134 (7)
O6	0.0534 (12)	0.0631 (14)	0.1118 (19)	−0.0173 (11)	0.0258 (12)	−0.0109 (13)
O7	0.0493 (13)	0.0665 (15)	0.163 (3)	0.0153 (11)	0.0119 (15)	−0.0009 (16)
S1	0.0555 (4)	0.0389 (3)	0.0527 (4)	0.0009 (3)	−0.0122 (3)	0.0189 (3)
F1	0.0759 (12)	0.0370 (8)	0.1018 (14)	−0.0127 (8)	−0.0333 (10)	0.0047 (8)

Geometric parameters (Å, º)

C1—C2	1.390 (3)	C17—H17	0.9300
C1—C6	1.396 (3)	C18—H18	0.9300
C1—N1	1.434 (3)	C19—O4	1.195 (3)
C2—C3	1.369 (4)	C19—O5	1.326 (3)
C2—H2	0.9300	C20—C21	1.377 (4)
C3—C4	1.395 (4)	C20—C25	1.387 (4)
C3—H3	0.9300	C20—S1	1.749 (3)
C4—O3	1.363 (3)	C21—C22	1.411 (6)
C4—C5	1.386 (3)	C21—H21	0.9300
C5—C6	1.393 (3)	C22—C23	1.381 (8)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.449 (3)	C23—C24	1.352 (7)
C7—C8	1.386 (3)	C23—H23	0.9300
C7—C12	1.400 (3)	C24—C25	1.365 (6)
C8—C9	1.393 (3)	C24—H24	0.9300
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.412 (3)	C26—O3	1.397 (4)
C9—C19	1.492 (3)	C26—H26A	0.9600
C10—C11	1.391 (3)	C26—H26B	0.9600
C10—C13	1.501 (3)	C26—H26C	0.9600
C11—C12	1.387 (3)	C27—O5	1.454 (3)
C11—H11	0.9300	C27—C28	1.490 (4)
C12—N1	1.421 (3)	C27—H27A	0.9700
C13—C18	1.392 (3)	C27—H27B	0.9700
C13—C14	1.393 (3)	C28—H28A	0.9600
C14—C15	1.381 (3)	C28—H28B	0.9600
C14—N2	1.471 (3)	C28—H28C	0.9600
C15—C16	1.371 (4)	N1—S1	1.668 (2)
C15—H15	0.9300	N2—O6	1.213 (3)
C16—F1	1.348 (3)	N2—O7	1.219 (3)
C16—C17	1.363 (4)	O1—S1	1.419 (2)
C17—C18	1.382 (3)	O2—S1	1.4172 (19)
C2—C1—C6	121.1 (2)	O4—C19—O5	122.6 (2)
C2—C1—N1	129.8 (2)	O4—C19—C9	124.0 (2)
C6—C1—N1	109.12 (19)	O5—C19—C9	113.48 (19)
C3—C2—C1	117.7 (3)	C21—C20—C25	122.3 (3)
C3—C2—H2	121.1	C21—C20—S1	119.3 (2)
C1—C2—H2	121.1	C25—C20—S1	118.5 (3)
C2—C3—C4	121.9 (2)	C20—C21—C22	117.5 (4)
C2—C3—H3	119.0	C20—C21—H21	121.3
C4—C3—H3	119.0	C22—C21—H21	121.3
O3—C4—C5	124.8 (3)	C23—C22—C21	119.1 (4)
O3—C4—C3	114.5 (2)	C23—C22—H22	120.5
C5—C4—C3	120.7 (3)	C21—C22—H22	120.5
C4—C5—C6	117.8 (2)	C24—C23—C22	122.0 (5)
C4—C5—H5	121.1	C24—C23—H23	119.0
C6—C5—H5	121.1	C22—C23—H23	119.0
C5—C6—C1	120.8 (2)	C23—C24—C25	120.1 (5)
C5—C6—C7	131.9 (2)	C23—C24—H24	119.9
C1—C6—C7	107.3 (2)	C25—C24—H24	119.9
C8—C7—C12	119.1 (2)	C24—C25—C20	119.0 (4)
C8—C7—C6	133.2 (2)	C24—C25—H25	120.5
C12—C7—C6	107.7 (2)	C20—C25—H25	120.5
C7—C8—C9	120.1 (2)	O3—C26—H26A	109.5
C7—C8—H8	119.9	O3—C26—H26B	109.5
C9—C8—H8	119.9	H26A—C26—H26B	109.5
C8—C9—C10	120.3 (2)	O3—C26—H26C	109.5
C8—C9—C19	119.7 (2)	H26A—C26—H26C	109.5
C10—C9—C19	120.0 (2)	H26B—C26—H26C	109.5
C11—C10—C9	119.5 (2)	O5—C27—C28	108.0 (2)
C11—C10—C13	114.0 (2)	O5—C27—H27A	110.1
C9—C10—C13	126.16 (19)	C28—C27—H27A	110.1
C12—C11—C10	119.4 (2)	O5—C27—H27B	110.1
C12—C11—H11	120.3	C28—C27—H27B	110.1
C10—C11—H11	120.3	H27A—C27—H27B	108.4
C11—C12—C7	121.5 (2)	C27—C28—H28A	109.5
C11—C12—N1	129.3 (2)	C27—C28—H28B	109.5
C7—C12—N1	109.07 (19)	H28A—C28—H28B	109.5
C18—C13—C14	115.5 (2)	C27—C28—H28C	109.5
C18—C13—C10	116.5 (2)	H28A—C28—H28C	109.5
C14—C13—C10	127.7 (2)	H28B—C28—H28C	109.5
C15—C14—C13	123.4 (2)	C12—N1—C1	106.72 (19)
C15—C14—N2	115.6 (2)	C12—N1—S1	122.61 (17)
C13—C14—N2	121.0 (2)	C1—N1—S1	122.44 (16)
C16—C15—C14	117.6 (2)	O6—N2—O7	123.7 (2)
C16—C15—H15	121.2	O6—N2—C14	118.9 (2)
C14—C15—H15	121.2	O7—N2—C14	117.4 (2)
F1—C16—C17	119.4 (2)	C4—O3—C26	118.4 (2)
F1—C16—C15	118.4 (2)	C19—O5—C27	115.66 (19)
C17—C16—C15	122.1 (2)	O2—S1—O1	119.94 (13)
C16—C17—C18	118.6 (2)	O2—S1—N1	106.24 (12)
C16—C17—H17	120.7	O1—S1—N1	106.37 (11)
C18—C17—H17	120.7	O2—S1—C20	109.43 (14)
C17—C18—C13	122.6 (2)	O1—S1—C20	109.01 (14)
C17—C18—H18	118.7	N1—S1—C20	104.74 (11)
C13—C18—H18	118.7
C6—C1—C2—C3	1.9 (4)	C15—C16—C17—C18	2.4 (4)
N1—C1—C2—C3	178.9 (3)	C16—C17—C18—C13	−0.9 (4)
C1—C2—C3—C4	−0.6 (5)	C14—C13—C18—C17	−1.1 (3)
C2—C3—C4—O3	179.4 (3)	C10—C13—C18—C17	173.7 (2)
C2—C3—C4—C5	−1.5 (5)	C8—C9—C19—O4	−177.3 (3)
O3—C4—C5—C6	−178.7 (3)	C10—C9—C19—O4	2.2 (4)
C3—C4—C5—C6	2.3 (4)	C8—C9—C19—O5	2.9 (3)
C4—C5—C6—C1	−1.0 (4)	C10—C9—C19—O5	−177.6 (2)
C4—C5—C6—C7	179.7 (3)	C25—C20—C21—C22	−1.9 (4)
C2—C1—C6—C5	−1.1 (4)	S1—C20—C21—C22	177.6 (2)
N1—C1—C6—C5	−178.7 (2)	C20—C21—C22—C23	1.2 (5)
C2—C1—C6—C7	178.4 (2)	C21—C22—C23—C24	1.6 (6)
N1—C1—C6—C7	0.8 (3)	C22—C23—C24—C25	−3.8 (7)
C5—C6—C7—C8	0.9 (5)	C23—C24—C25—C20	3.1 (6)
C1—C6—C7—C8	−178.5 (3)	C21—C20—C25—C24	−0.2 (5)
C5—C6—C7—C12	−179.8 (3)	S1—C20—C25—C24	−179.7 (3)
C1—C6—C7—C12	0.9 (3)	C11—C12—N1—C1	179.3 (2)
C12—C7—C8—C9	−0.1 (4)	C7—C12—N1—C1	2.6 (3)
C6—C7—C8—C9	179.2 (2)	C11—C12—N1—S1	−31.7 (4)
C7—C8—C9—C10	0.0 (3)	C7—C12—N1—S1	151.62 (18)
C7—C8—C9—C19	179.5 (2)	C2—C1—N1—C12	−179.4 (3)
C8—C9—C10—C11	0.0 (3)	C6—C1—N1—C12	−2.1 (3)
C19—C9—C10—C11	−179.5 (2)	C2—C1—N1—S1	31.5 (4)
C8—C9—C10—C13	−173.3 (2)	C6—C1—N1—S1	−151.14 (19)
C19—C9—C10—C13	7.2 (4)	C15—C14—N2—O6	155.8 (3)
C9—C10—C11—C12	0.2 (4)	C13—C14—N2—O6	−24.6 (4)
C13—C10—C11—C12	174.2 (2)	C15—C14—N2—O7	−24.1 (4)
C10—C11—C12—C7	−0.3 (4)	C13—C14—N2—O7	155.5 (3)
C10—C11—C12—N1	−176.7 (2)	C5—C4—O3—C26	−1.4 (5)
C8—C7—C12—C11	0.2 (4)	C3—C4—O3—C26	177.7 (3)
C6—C7—C12—C11	−179.2 (2)	O4—C19—O5—C27	3.4 (4)
C8—C7—C12—N1	177.3 (2)	C9—C19—O5—C27	−176.7 (2)
C6—C7—C12—N1	−2.2 (3)	C28—C27—O5—C19	−177.3 (2)
C11—C10—C13—C18	−62.6 (3)	C12—N1—S1—O2	173.3 (2)
C9—C10—C13—C18	110.9 (3)	C1—N1—S1—O2	−42.4 (2)
C11—C10—C13—C14	111.5 (3)	C12—N1—S1—O1	44.5 (2)
C9—C10—C13—C14	−75.0 (3)	C1—N1—S1—O1	−171.3 (2)
C18—C13—C14—C15	1.8 (3)	C12—N1—S1—C20	−70.9 (2)
C10—C13—C14—C15	−172.4 (2)	C1—N1—S1—C20	73.4 (2)
C18—C13—C14—N2	−177.8 (2)	C21—C20—S1—O2	33.8 (3)
C10—C13—C14—N2	8.1 (4)	C25—C20—S1—O2	−146.8 (2)
C13—C14—C15—C16	−0.4 (4)	C21—C20—S1—O1	166.7 (2)
N2—C14—C15—C16	179.1 (2)	C25—C20—S1—O1	−13.8 (2)
C14—C15—C16—F1	177.9 (2)	C21—C20—S1—N1	−79.8 (2)
C14—C15—C16—C17	−1.7 (4)	C25—C20—S1—N1	99.7 (2)
F1—C16—C17—C18	−177.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.36	2.945 (4)	121
C3—H3···O4^i	0.93	2.37	3.301 (3)	174
C11—H11···O1	0.93	2.35	2.952 (3)	123
C17—H17···O7^ii	0.93	2.50	3.428 (3)	173

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

12-(Benzenesulfonyl)-12H-quinolino[4,3-b]carbazole (II)

Crystal data

C25H16N2O2S	F(000) = 848
Mr = 408.46	Dx = 1.410 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.142 (1) Å	Cell parameters from 9986 reflections
b = 12.097 (1) Å	θ = 2.7–29.5°
c = 16.2218 (15) Å	µ = 0.19 mm^−1
β = 104.846 (4)°	T = 296 K
V = 1923.8 (3) Å^3	Solid, colourless
Z = 4	0.40 × 0.35 × 0.25 mm

Data collection

Bruker D8 Venture diffractometer with Photon II detector	4185 independent reflections
Radiation source: fine-focus sealed tube	3488 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω and φ scan	θmax = 27.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −12→12
Tmin = 0.867, Tmax = 0.957	k = −15→15
60289 measured reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.161	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 2.5552P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
4185 reflections	Δρmax = 0.32 e Å^−3
271 parameters	Δρmin = −0.44 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8659 (3)	0.1951 (2)	0.62473 (17)	0.0405 (6)
C2	0.8576 (3)	0.1281 (3)	0.69302 (19)	0.0518 (7)
H2	0.796204	0.142990	0.725444	0.062*
C3	0.9447 (3)	0.0387 (3)	0.7104 (2)	0.0592 (8)
H3	0.941923	−0.007334	0.755800	0.071*
C4	1.0364 (3)	0.0151 (3)	0.6623 (2)	0.0576 (8)
H4	1.094393	−0.045445	0.676287	0.069*
C5	1.0418 (3)	0.0807 (2)	0.5943 (2)	0.0515 (7)
H5	1.102062	0.064446	0.561328	0.062*
C6	0.9560 (3)	0.1717 (2)	0.57542 (16)	0.0391 (5)
C7	0.9415 (2)	0.2576 (2)	0.51200 (16)	0.0368 (5)
C8	1.0084 (3)	0.2769 (2)	0.44958 (17)	0.0427 (6)
H8	1.075496	0.228451	0.441961	0.051*
C9	0.9744 (3)	0.3705 (2)	0.39769 (16)	0.0392 (6)
C10	0.8736 (2)	0.4456 (2)	0.40903 (15)	0.0340 (5)
C11	0.8069 (3)	0.4262 (2)	0.47373 (15)	0.0363 (5)
H11	0.741028	0.474851	0.482689	0.044*
C12	0.8418 (2)	0.3330 (2)	0.52353 (15)	0.0340 (5)
C13	0.8459 (2)	0.5400 (2)	0.35213 (15)	0.0372 (5)
C14	0.7505 (3)	0.6228 (2)	0.35608 (18)	0.0457 (6)
H14	0.701230	0.617974	0.397050	0.055*
C15	0.7285 (3)	0.7109 (3)	0.3006 (2)	0.0543 (7)
H15	0.664791	0.764658	0.304288	0.065*
C16	0.8013 (3)	0.7197 (3)	0.2390 (2)	0.0562 (8)
H16	0.786655	0.779570	0.201767	0.067*
C17	0.8941 (3)	0.6405 (3)	0.2332 (2)	0.0533 (7)
H17	0.941880	0.646462	0.191462	0.064*
C18	0.9187 (3)	0.5501 (2)	0.28923 (17)	0.0432 (6)
C19	1.0408 (3)	0.3910 (3)	0.33103 (19)	0.0523 (7)
H19	1.107016	0.340809	0.324773	0.063*
C20	0.5258 (3)	0.2476 (3)	0.54943 (17)	0.0464 (6)
C21	0.4892 (3)	0.1494 (3)	0.5817 (2)	0.0557 (8)
H21	0.529794	0.128664	0.637693	0.067*
C22	0.3916 (4)	0.0826 (3)	0.5298 (3)	0.0770 (11)
H22	0.364572	0.017708	0.551609	0.092*
C23	0.3347 (4)	0.1110 (5)	0.4470 (3)	0.0920 (16)
H23	0.270298	0.064956	0.412217	0.110*
C24	0.3727 (4)	0.2082 (5)	0.4147 (3)	0.0880 (15)
H24	0.333913	0.226625	0.358053	0.106*
C25	0.4677 (3)	0.2788 (4)	0.4653 (2)	0.0656 (9)
H25	0.491861	0.344837	0.443700	0.079*
N1	0.7952 (2)	0.29582 (18)	0.59462 (14)	0.0400 (5)
N2	1.0159 (3)	0.4741 (2)	0.27880 (17)	0.0562 (7)
O1	0.6239 (2)	0.44428 (18)	0.58737 (15)	0.0610 (6)
O2	0.6604 (2)	0.30363 (18)	0.70130 (12)	0.0553 (5)
S1	0.64894 (7)	0.33247 (6)	0.61490 (4)	0.0440 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0408 (13)	0.0378 (13)	0.0409 (13)	0.0012 (11)	0.0070 (11)	0.0004 (10)
C2	0.0532 (17)	0.0534 (17)	0.0502 (16)	0.0005 (14)	0.0156 (13)	0.0084 (13)
C3	0.0629 (19)	0.0517 (18)	0.0594 (18)	−0.0013 (15)	0.0089 (15)	0.0174 (15)
C4	0.0558 (18)	0.0442 (16)	0.067 (2)	0.0085 (14)	0.0056 (15)	0.0108 (14)
C5	0.0474 (16)	0.0465 (16)	0.0583 (17)	0.0119 (13)	0.0097 (13)	0.0023 (13)
C6	0.0380 (13)	0.0377 (13)	0.0392 (13)	0.0019 (10)	0.0056 (10)	−0.0006 (10)
C7	0.0323 (12)	0.0378 (13)	0.0386 (12)	0.0026 (10)	0.0061 (10)	−0.0032 (10)
C8	0.0375 (13)	0.0437 (14)	0.0492 (15)	0.0108 (11)	0.0156 (11)	−0.0018 (11)
C9	0.0358 (13)	0.0451 (14)	0.0386 (13)	0.0029 (11)	0.0131 (10)	−0.0029 (11)
C10	0.0328 (11)	0.0337 (12)	0.0344 (12)	−0.0022 (9)	0.0064 (9)	−0.0052 (9)
C11	0.0374 (12)	0.0339 (12)	0.0393 (13)	0.0030 (10)	0.0129 (10)	−0.0036 (10)
C12	0.0325 (11)	0.0363 (12)	0.0336 (11)	0.0011 (10)	0.0093 (9)	−0.0038 (9)
C13	0.0360 (12)	0.0379 (13)	0.0361 (12)	−0.0052 (10)	0.0061 (10)	−0.0041 (10)
C14	0.0477 (15)	0.0428 (14)	0.0475 (15)	0.0013 (12)	0.0138 (12)	0.0013 (12)
C15	0.0539 (17)	0.0420 (15)	0.0649 (19)	0.0036 (13)	0.0114 (14)	0.0058 (14)
C16	0.0565 (18)	0.0482 (17)	0.0610 (19)	−0.0062 (14)	0.0096 (14)	0.0149 (14)
C17	0.0498 (16)	0.0584 (18)	0.0536 (17)	−0.0098 (14)	0.0169 (13)	0.0094 (14)
C18	0.0402 (14)	0.0464 (15)	0.0437 (14)	−0.0050 (11)	0.0118 (11)	0.0009 (11)
C19	0.0480 (16)	0.0606 (18)	0.0554 (17)	0.0123 (14)	0.0263 (13)	0.0040 (14)
C20	0.0378 (13)	0.0620 (18)	0.0432 (14)	0.0135 (12)	0.0174 (11)	−0.0015 (13)
C21	0.0441 (16)	0.0581 (18)	0.068 (2)	0.0082 (14)	0.0211 (14)	−0.0037 (15)
C22	0.051 (2)	0.070 (2)	0.111 (3)	−0.0021 (17)	0.024 (2)	−0.020 (2)
C23	0.0415 (19)	0.116 (4)	0.112 (4)	0.010 (2)	0.008 (2)	−0.048 (3)
C24	0.049 (2)	0.148 (5)	0.059 (2)	0.032 (3)	−0.0014 (16)	−0.021 (3)
C25	0.0470 (17)	0.098 (3)	0.0527 (18)	0.0202 (18)	0.0141 (14)	0.0052 (18)
N1	0.0420 (12)	0.0391 (11)	0.0415 (11)	0.0061 (9)	0.0155 (9)	0.0025 (9)
N2	0.0544 (15)	0.0668 (17)	0.0552 (15)	0.0032 (13)	0.0283 (12)	0.0068 (13)
O1	0.0772 (15)	0.0467 (12)	0.0726 (14)	0.0203 (11)	0.0439 (12)	0.0080 (10)
O2	0.0696 (14)	0.0626 (13)	0.0396 (10)	0.0056 (11)	0.0249 (10)	−0.0039 (9)
S1	0.0508 (4)	0.0455 (4)	0.0419 (4)	0.0091 (3)	0.0230 (3)	0.0002 (3)

Geometric parameters (Å, º)

C1—C6	1.389 (4)	C14—H14	0.9300
C1—C2	1.392 (4)	C15—C16	1.390 (5)
C1—N1	1.435 (3)	C15—H15	0.9300
C2—C3	1.379 (4)	C16—C17	1.364 (5)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.387 (5)	C17—C18	1.403 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.372 (4)	C18—N2	1.390 (4)
C4—H4	0.9300	C19—N2	1.297 (4)
C5—C6	1.388 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.387 (4)
C6—C7	1.444 (4)	C20—C25	1.393 (4)
C7—C8	1.376 (4)	C20—S1	1.750 (3)
C7—C12	1.409 (3)	C21—C22	1.384 (5)
C8—C9	1.400 (4)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.364 (6)
C9—C10	1.415 (3)	C22—H22	0.9300
C9—C19	1.435 (4)	C23—C24	1.381 (7)
C10—C11	1.407 (3)	C23—H23	0.9300
C10—C13	1.450 (3)	C24—C25	1.388 (6)
C11—C12	1.379 (3)	C24—H24	0.9300
C11—H11	0.9300	C25—H25	0.9300
C12—N1	1.426 (3)	N1—S1	1.660 (2)
C13—C14	1.405 (4)	O1—S1	1.427 (2)
C13—C18	1.409 (4)	O2—S1	1.420 (2)
C14—C15	1.375 (4)
C6—C1—C2	121.5 (3)	C14—C15—H15	119.9
C6—C1—N1	108.8 (2)	C16—C15—H15	119.9
C2—C1—N1	129.7 (3)	C17—C16—C15	119.9 (3)
C3—C2—C1	116.9 (3)	C17—C16—H16	120.0
C3—C2—H2	121.6	C15—C16—H16	120.0
C1—C2—H2	121.6	C16—C17—C18	120.9 (3)
C2—C3—C4	122.2 (3)	C16—C17—H17	119.5
C2—C3—H3	118.9	C18—C17—H17	119.5
C4—C3—H3	118.9	N2—C18—C17	116.7 (3)
C5—C4—C3	120.2 (3)	N2—C18—C13	123.4 (2)
C5—C4—H4	119.9	C17—C18—C13	119.9 (3)
C3—C4—H4	119.9	N2—C19—C9	125.2 (3)
C4—C5—C6	118.9 (3)	N2—C19—H19	117.4
C4—C5—H5	120.5	C9—C19—H19	117.4
C6—C5—H5	120.5	C21—C20—C25	121.0 (3)
C5—C6—C1	120.2 (3)	C21—C20—S1	119.5 (2)
C5—C6—C7	132.2 (3)	C25—C20—S1	119.5 (3)
C1—C6—C7	107.5 (2)	C22—C21—C20	119.3 (4)
C8—C7—C12	119.6 (2)	C22—C21—H21	120.4
C8—C7—C6	131.9 (2)	C20—C21—H21	120.4
C12—C7—C6	108.5 (2)	C23—C22—C21	120.6 (4)
C7—C8—C9	119.2 (2)	C23—C22—H22	119.7
C7—C8—H8	120.4	C21—C22—H22	119.7
C9—C8—H8	120.4	C22—C23—C24	119.9 (4)
C8—C9—C10	121.1 (2)	C22—C23—H23	120.0
C8—C9—C19	120.2 (2)	C24—C23—H23	120.0
C10—C9—C19	118.8 (2)	C23—C24—C25	121.3 (4)
C11—C10—C9	119.4 (2)	C23—C24—H24	119.4
C11—C10—C13	123.7 (2)	C25—C24—H24	119.4
C9—C10—C13	116.9 (2)	C24—C25—C20	117.9 (4)
C12—C11—C10	118.3 (2)	C24—C25—H25	121.1
C12—C11—H11	120.9	C20—C25—H25	121.1
C10—C11—H11	120.9	C12—N1—C1	107.6 (2)
C11—C12—C7	122.4 (2)	C12—N1—S1	125.03 (17)
C11—C12—N1	130.0 (2)	C1—N1—S1	123.60 (18)
C7—C12—N1	107.5 (2)	C19—N2—C18	117.3 (2)
C14—C13—C18	117.8 (2)	O2—S1—O1	120.34 (13)
C14—C13—C10	123.8 (2)	O2—S1—N1	106.19 (12)
C18—C13—C10	118.5 (2)	O1—S1—N1	106.70 (12)
C15—C14—C13	121.3 (3)	O2—S1—C20	108.65 (14)
C15—C14—H14	119.3	O1—S1—C20	108.92 (15)
C13—C14—H14	119.3	N1—S1—C20	104.97 (12)
C14—C15—C16	120.2 (3)
C6—C1—C2—C3	1.1 (4)	C16—C17—C18—N2	−179.5 (3)
N1—C1—C2—C3	−176.1 (3)	C16—C17—C18—C13	0.5 (4)
C1—C2—C3—C4	−0.3 (5)	C14—C13—C18—N2	179.8 (3)
C2—C3—C4—C5	−0.8 (5)	C10—C13—C18—N2	0.0 (4)
C3—C4—C5—C6	1.1 (5)	C14—C13—C18—C17	−0.2 (4)
C4—C5—C6—C1	−0.3 (4)	C10—C13—C18—C17	180.0 (2)
C4—C5—C6—C7	176.9 (3)	C8—C9—C19—N2	179.1 (3)
C2—C1—C6—C5	−0.9 (4)	C10—C9—C19—N2	−0.2 (5)
N1—C1—C6—C5	176.9 (2)	C25—C20—C21—C22	−1.2 (4)
C2—C1—C6—C7	−178.7 (3)	S1—C20—C21—C22	179.9 (2)
N1—C1—C6—C7	−0.9 (3)	C20—C21—C22—C23	2.0 (5)
C5—C6—C7—C8	0.0 (5)	C21—C22—C23—C24	−1.1 (6)
C1—C6—C7—C8	177.4 (3)	C22—C23—C24—C25	−0.5 (6)
C5—C6—C7—C12	−177.5 (3)	C23—C24—C25—C20	1.2 (5)
C1—C6—C7—C12	0.0 (3)	C21—C20—C25—C24	−0.4 (4)
C12—C7—C8—C9	−1.1 (4)	S1—C20—C25—C24	178.5 (2)
C6—C7—C8—C9	−178.3 (3)	C11—C12—N1—C1	−178.7 (2)
C7—C8—C9—C10	0.6 (4)	C7—C12—N1—C1	−1.4 (3)
C7—C8—C9—C19	−178.7 (3)	C11—C12—N1—S1	22.5 (4)
C8—C9—C10—C11	0.2 (4)	C7—C12—N1—S1	−160.13 (18)
C19—C9—C10—C11	179.6 (2)	C6—C1—N1—C12	1.4 (3)
C8—C9—C10—C13	179.9 (2)	C2—C1—N1—C12	179.0 (3)
C19—C9—C10—C13	−0.8 (4)	C6—C1—N1—S1	160.52 (19)
C9—C10—C11—C12	−0.7 (4)	C2—C1—N1—S1	−21.9 (4)
C13—C10—C11—C12	179.7 (2)	C9—C19—N2—C18	1.1 (5)
C10—C11—C12—C7	0.2 (4)	C17—C18—N2—C19	179.1 (3)
C10—C11—C12—N1	177.2 (2)	C13—C18—N2—C19	−0.9 (4)
C8—C7—C12—C11	0.6 (4)	C12—N1—S1—O2	−163.8 (2)
C6—C7—C12—C11	178.5 (2)	C1—N1—S1—O2	40.7 (2)
C8—C7—C12—N1	−176.9 (2)	C12—N1—S1—O1	−34.3 (3)
C6—C7—C12—N1	0.9 (3)	C1—N1—S1—O1	170.2 (2)
C11—C10—C13—C14	0.7 (4)	C12—N1—S1—C20	81.2 (2)
C9—C10—C13—C14	−179.0 (2)	C1—N1—S1—C20	−74.3 (2)
C11—C10—C13—C18	−179.5 (2)	C21—C20—S1—O2	−19.3 (3)
C9—C10—C13—C18	0.9 (3)	C25—C20—S1—O2	161.8 (2)
C18—C13—C14—C15	0.0 (4)	C21—C20—S1—O1	−152.1 (2)
C10—C13—C14—C15	179.8 (3)	C25—C20—S1—O1	29.0 (3)
C13—C14—C15—C16	−0.1 (5)	C21—C20—S1—N1	94.0 (2)
C14—C15—C16—C17	0.4 (5)	C25—C20—S1—N1	−84.9 (2)
C15—C16—C17—C18	−0.6 (5)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of ring C13–C18 and Cg2 is the centroid of ring C7–C12.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.36	2.944 (4)	121
C11—H11···O1	0.93	2.34	2.940 (3)	122
C21—H21···N2^i	0.93	2.64	3.476 (4)	150
C4—H4···Cg1^ii	0.93	2.80	3.605 (4)	145
C16—H16···Cg3^iii	0.93	2.99	3.747 (3)	139

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