Crystal structures of 4-bromo-2-formyl-1-tosyl-1H-pyrrole, (E)-4-bromo-2-(2-nitro­vin­yl)-1-tosyl-1H-pyrrole and 6-(4-bromo-1-tosyl­pyrrol-2-yl)-4,4-dimethyl-5-nitro­hexan-2-one

Crystal structures of three substituted N-tosyl­pyrrole compounds are reported; these compounds show a variety of `weak' inter­molecular inter­actions owing to different substitution patterns and supra­molecular arrangements. The benefits of collecting crystal structure data to extreme resolution (0.5 Å) are discussed.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.021
• wR factor = 0.045
• Data-to-parameter ratio = 24.2

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.142
• Data-to-parameter ratio = 13.7

Structure: 3

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.027
• wR factor = 0.076
• Data-to-parameter ratio = 71.7

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z > Si, NonCentro ....     Please Do !

Alert level G
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: 2


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         21 Report

Author Response: Reflections unmeasured.

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 3


Alert level C
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Author Response: Reflection 3 0 2

PLAT977_ALERT_2_C Check Negative Difference Density on H5               -0.33 eA-3

Author Response: Atom is near the midpoint between the S and Br atoms - while assigned correctly, e- density is affected by fourier issues.

Alert level G
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.61 mm
PLAT793_ALERT_4_G Model has Chirality at C7          (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         15 Info

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

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

---

Computing details

For all structures, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: shelXle (Hübschle, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

4-Bromo-1-[(4-methylbenzene)sulfonyl]pyrrole-2-carbaldehyde (1)

Crystal data

C12H10BrNO3S	Dx = 1.744 Mg m^−3
Mr = 328.18	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9913 reflections
a = 4.8436 (5) Å	θ = 2.9–31.4°
b = 13.9149 (13) Å	µ = 3.45 mm^−1
c = 18.5479 (17) Å	T = 100 K
V = 1250.1 (2) Å^3	Rod, colourless
Z = 4	0.20 × 0.09 × 0.06 mm
F(000) = 656

Data collection

Bruker APEXII CCD diffractometer	3714 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.028
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 31.0°, θmin = 1.8°
Tmin = 0.616, Tmax = 0.746	h = −7→6
23296 measured reflections	k = −20→19
3972 independent reflections	l = −20→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.045	w = 1/[σ^2(Fo^2) + (0.0201P)^2 + 0.4002P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3972 reflections	Δρmax = 0.34 e Å^−3
164 parameters	Δρmin = −0.38 e Å^−3
0 restraints

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
Br1	1.03533 (5)	0.95495 (2)	0.67018 (2)	0.02243 (6)
N1	0.5067 (3)	0.73027 (11)	0.66274 (9)	0.0138 (3)
C2	0.5792 (4)	0.72511 (15)	0.73590 (11)	0.0167 (4)
C3	0.7636 (4)	0.79838 (15)	0.74892 (11)	0.0181 (4)
H3	0.847177	0.813140	0.793908	0.022*
C4	0.8059 (4)	0.84751 (15)	0.68338 (10)	0.0163 (4)
C5	0.6504 (4)	0.80452 (15)	0.63092 (11)	0.0153 (4)
H5	0.642846	0.822553	0.581559	0.018*
C6	0.4882 (5)	0.65241 (16)	0.78783 (11)	0.0226 (4)
H6	0.357430	0.605380	0.773252	0.027*
O7	0.5766 (4)	0.65095 (14)	0.84935 (8)	0.0334 (4)
S9	0.30100 (10)	0.65428 (4)	0.61513 (3)	0.01313 (9)
O10	0.2261 (3)	0.70813 (11)	0.55234 (7)	0.0167 (3)
O11	0.0978 (3)	0.62059 (10)	0.66500 (8)	0.0175 (3)
C12	0.5188 (4)	0.55963 (13)	0.59054 (10)	0.0135 (3)
C13	0.6698 (4)	0.56650 (15)	0.52637 (11)	0.0170 (4)
H13	0.653329	0.621364	0.496191	0.020*
C14	0.8442 (5)	0.49124 (16)	0.50790 (12)	0.0187 (4)
H14	0.947090	0.494838	0.464384	0.022*
C15	0.8716 (4)	0.41035 (16)	0.55192 (12)	0.0182 (4)
C16	0.7162 (5)	0.40561 (16)	0.61547 (12)	0.0189 (4)
H16	0.731639	0.350655	0.645586	0.023*
C17	0.5402 (5)	0.47959 (14)	0.63526 (11)	0.0168 (4)
H17	0.436014	0.475763	0.678556	0.020*
C18	1.0659 (5)	0.33074 (16)	0.53061 (12)	0.0236 (5)
H18A	1.020615	0.308589	0.481867	0.035*
H18B	1.047418	0.277176	0.564571	0.035*
H18C	1.256213	0.354656	0.531514	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02171 (10)	0.01959 (10)	0.02598 (10)	−0.00630 (9)	0.00443 (8)	−0.00624 (9)
N1	0.0142 (8)	0.0138 (7)	0.0134 (7)	−0.0004 (6)	−0.0005 (7)	−0.0014 (6)
C2	0.0185 (10)	0.0186 (10)	0.0128 (8)	0.0029 (8)	−0.0004 (7)	−0.0026 (7)
C3	0.0192 (10)	0.0193 (10)	0.0159 (9)	0.0014 (8)	−0.0004 (8)	−0.0050 (8)
C4	0.0146 (9)	0.0150 (9)	0.0194 (10)	−0.0004 (8)	0.0021 (7)	−0.0045 (7)
C5	0.0149 (9)	0.0155 (10)	0.0155 (9)	0.0010 (7)	0.0012 (7)	0.0009 (7)
C6	0.0289 (12)	0.0209 (10)	0.0182 (9)	−0.0009 (10)	−0.0002 (9)	−0.0004 (8)
O7	0.0507 (12)	0.0331 (9)	0.0166 (7)	−0.0048 (9)	−0.0060 (7)	0.0037 (7)
S9	0.0118 (2)	0.0141 (2)	0.0135 (2)	0.00034 (18)	−0.00095 (17)	−0.00007 (17)
O10	0.0166 (7)	0.0179 (7)	0.0154 (7)	0.0011 (6)	−0.0039 (5)	0.0015 (6)
O11	0.0135 (7)	0.0210 (7)	0.0181 (7)	−0.0011 (5)	0.0031 (6)	0.0006 (6)
C12	0.0123 (8)	0.0125 (9)	0.0156 (8)	0.0001 (7)	−0.0010 (7)	−0.0015 (6)
C13	0.0172 (10)	0.0170 (10)	0.0168 (9)	0.0011 (8)	−0.0007 (7)	0.0005 (7)
C14	0.0177 (10)	0.0218 (10)	0.0165 (9)	0.0008 (8)	0.0005 (8)	−0.0040 (8)
C15	0.0148 (9)	0.0182 (10)	0.0215 (10)	0.0007 (8)	−0.0070 (7)	−0.0068 (8)
C16	0.0191 (10)	0.0168 (10)	0.0208 (10)	0.0015 (8)	−0.0056 (8)	0.0012 (8)
C17	0.0166 (9)	0.0167 (9)	0.0170 (9)	−0.0011 (8)	−0.0015 (8)	0.0014 (7)
C18	0.0202 (11)	0.0226 (11)	0.0280 (11)	0.0045 (9)	−0.0076 (9)	−0.0094 (9)

Geometric parameters (Å, º)

Br1—C4	1.879 (2)	C12—C17	1.393 (3)
N1—C5	1.378 (3)	C12—C13	1.400 (3)
N1—C2	1.404 (2)	C13—C14	1.388 (3)
N1—S9	1.7002 (16)	C13—H13	0.9500
C2—C3	1.377 (3)	C14—C15	1.397 (3)
C2—C6	1.465 (3)	C14—H14	0.9500
C3—C4	1.410 (3)	C15—C16	1.400 (3)
C3—H3	0.9500	C15—C18	1.506 (3)
C4—C5	1.368 (3)	C16—C17	1.386 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—O7	1.219 (3)	C17—H17	0.9500
C6—H6	0.9500	C18—H18A	0.9800
S9—O11	1.4296 (15)	C18—H18B	0.9800
S9—O10	1.4316 (15)	C18—H18C	0.9800
S9—C12	1.7481 (19)
C5—N1—C2	109.04 (16)	C17—C12—C13	121.47 (18)
C5—N1—S9	122.66 (14)	C17—C12—S9	119.47 (15)
C2—N1—S9	128.08 (14)	C13—C12—S9	119.05 (15)
C3—C2—N1	107.09 (18)	C14—C13—C12	118.42 (19)
C3—C2—C6	126.25 (19)	C14—C13—H13	120.8
N1—C2—C6	126.58 (19)	C12—C13—H13	120.8
C2—C3—C4	107.59 (18)	C13—C14—C15	121.4 (2)
C2—C3—H3	126.2	C13—C14—H14	119.3
C4—C3—H3	126.2	C15—C14—H14	119.3
C5—C4—C3	108.74 (19)	C16—C15—C14	118.6 (2)
C5—C4—Br1	125.50 (16)	C16—C15—C18	121.5 (2)
C3—C4—Br1	125.75 (15)	C14—C15—C18	119.9 (2)
C4—C5—N1	107.52 (17)	C17—C16—C15	121.2 (2)
C4—C5—H5	126.2	C17—C16—H16	119.4
N1—C5—H5	126.2	C15—C16—H16	119.4
O7—C6—C2	121.4 (2)	C16—C17—C12	118.81 (19)
O7—C6—H6	119.3	C16—C17—H17	120.6
C2—C6—H6	119.3	C12—C17—H17	120.6
O11—S9—O10	121.57 (9)	C15—C18—H18A	109.5
O11—S9—N1	105.75 (9)	C15—C18—H18B	109.5
O10—S9—N1	104.20 (9)	H18A—C18—H18B	109.5
O11—S9—C12	109.72 (9)	C15—C18—H18C	109.5
O10—S9—C12	109.57 (9)	H18A—C18—H18C	109.5
N1—S9—C12	104.50 (9)	H18B—C18—H18C	109.5
C5—N1—C2—C3	1.4 (2)	C5—N1—S9—C12	90.92 (17)
S9—N1—C2—C3	176.08 (15)	C2—N1—S9—C12	−83.10 (19)
C5—N1—C2—C6	−175.5 (2)	O11—S9—C12—C17	−21.53 (19)
S9—N1—C2—C6	−0.8 (3)	O10—S9—C12—C17	−157.39 (16)
N1—C2—C3—C4	−0.7 (2)	N1—S9—C12—C17	91.45 (17)
C6—C2—C3—C4	176.3 (2)	O11—S9—C12—C13	158.96 (16)
C2—C3—C4—C5	−0.3 (2)	O10—S9—C12—C13	23.10 (19)
C2—C3—C4—Br1	179.24 (16)	N1—S9—C12—C13	−88.05 (17)
C3—C4—C5—N1	1.2 (2)	C17—C12—C13—C14	−0.2 (3)
Br1—C4—C5—N1	−178.37 (14)	S9—C12—C13—C14	179.33 (16)
C2—N1—C5—C4	−1.6 (2)	C12—C13—C14—C15	−0.3 (3)
S9—N1—C5—C4	−176.62 (14)	C13—C14—C15—C16	0.7 (3)
C3—C2—C6—O7	−0.9 (4)	C13—C14—C15—C18	−179.1 (2)
N1—C2—C6—O7	175.5 (2)	C14—C15—C16—C17	−0.6 (3)
C5—N1—S9—O11	−153.29 (16)	C18—C15—C16—C17	179.2 (2)
C2—N1—S9—O11	32.69 (19)	C15—C16—C17—C12	0.2 (3)
C5—N1—S9—O10	−24.06 (18)	C13—C12—C17—C16	0.2 (3)
C2—N1—S9—O10	161.93 (17)	S9—C12—C17—C16	−179.26 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O11	0.95	2.38	2.994 (3)	122
C5—H5···O10^i	0.95	2.55	3.423 (2)	153
C13—H13···O10^i	0.95	2.56	3.470 (3)	160

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

(E)-4-bromo-2-(2-nitrovinyl)-1-tosyl-1H-pyrrole (2)

Crystal data

C13H11BrN2O4S	Z = 2
Mr = 371.21	F(000) = 372
Triclinic, P1	Dx = 1.707 Mg m^−3
a = 6.8904 (4) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.3224 (4) Å	Cell parameters from 4853 reflections
c = 12.8763 (7) Å	θ = 3.5–68.2°
α = 83.423 (3)°	µ = 5.40 mm^−1
β = 80.393 (3)°	T = 100 K
γ = 85.693 (3)°	Plate, colourless
V = 722.06 (7) Å^3	0.08 × 0.06 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer	2378 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.042
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 68.2°, θmin = 3.5°
Tmin = 0.544, Tmax = 0.753	h = −6→8
7190 measured reflections	k = −9→9
2617 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.1118P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2617 reflections	Δρmax = 0.80 e Å^−3
191 parameters	Δρmin = −0.63 e Å^−3
0 restraints

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
Br1	0.78111 (5)	0.59378 (4)	0.35381 (3)	0.0425 (2)
N1	0.6292 (5)	0.7256 (3)	0.6502 (2)	0.0384 (6)
C2	0.4649 (5)	0.7946 (4)	0.6072 (3)	0.0358 (7)
C3	0.4914 (5)	0.7634 (4)	0.5026 (3)	0.0392 (7)
H3	0.405169	0.797263	0.452898	0.047*
C4	0.6723 (5)	0.6710 (4)	0.4840 (3)	0.0388 (7)
C5	0.7544 (6)	0.6478 (4)	0.5740 (3)	0.0397 (7)
H5	0.875264	0.589067	0.582710	0.048*
C6	0.3020 (5)	0.8827 (4)	0.6651 (3)	0.0381 (7)
H6	0.306219	0.898197	0.736623	0.046*
C7	0.1474 (6)	0.9425 (5)	0.6225 (3)	0.0437 (8)
H7	0.141618	0.927123	0.551082	0.052*
N8	−0.0128 (5)	1.0308 (4)	0.6821 (3)	0.0447 (7)
O9	−0.0096 (4)	1.0452 (4)	0.7764 (2)	0.0499 (6)
O10	−0.1458 (5)	1.0858 (5)	0.6356 (3)	0.0706 (10)
S11	0.66335 (12)	0.69881 (8)	0.77875 (6)	0.0366 (2)
O12	0.5680 (4)	0.8370 (3)	0.8260 (2)	0.0435 (6)
O13	0.8708 (4)	0.6635 (3)	0.7737 (2)	0.0429 (6)
C14	0.5375 (5)	0.5261 (4)	0.8327 (2)	0.0338 (6)
C15	0.3465 (6)	0.5434 (4)	0.8867 (3)	0.0469 (8)
H15	0.283748	0.647790	0.895024	0.056*
C16	0.2498 (6)	0.4049 (5)	0.9280 (3)	0.0503 (9)
H16	0.118816	0.415207	0.964877	0.060*
C17	0.3389 (6)	0.2510 (4)	0.9171 (3)	0.0408 (7)
C18	0.5283 (5)	0.2385 (4)	0.8610 (3)	0.0395 (7)
H18	0.589695	0.134135	0.851045	0.047*
C19	0.6306 (5)	0.3744 (4)	0.8189 (3)	0.0386 (7)
H19	0.761277	0.364040	0.781580	0.046*
C20	0.2280 (6)	0.1045 (4)	0.9648 (3)	0.0480 (9)
H20A	0.123086	0.091657	0.924079	0.072*
H20B	0.169992	0.118266	1.038312	0.072*
H20C	0.318724	0.007925	0.963164	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0488 (3)	0.0434 (3)	0.0347 (3)	−0.00224 (17)	−0.00398 (17)	−0.00571 (16)
N1	0.0524 (17)	0.0278 (13)	0.0348 (14)	−0.0006 (11)	−0.0084 (12)	−0.0016 (10)
C2	0.0443 (18)	0.0255 (14)	0.0371 (17)	−0.0049 (12)	−0.0072 (14)	0.0015 (12)
C3	0.0442 (18)	0.0341 (16)	0.0370 (17)	−0.0033 (13)	−0.0016 (14)	−0.0004 (12)
C4	0.0500 (19)	0.0289 (15)	0.0360 (16)	−0.0051 (13)	−0.0024 (14)	−0.0020 (12)
C5	0.0501 (19)	0.0293 (15)	0.0381 (17)	0.0016 (12)	−0.0031 (14)	−0.0046 (12)
C6	0.050 (2)	0.0284 (14)	0.0339 (16)	−0.0054 (13)	−0.0027 (14)	−0.0009 (12)
C7	0.0436 (19)	0.0496 (19)	0.0376 (18)	−0.0050 (15)	−0.0016 (14)	−0.0091 (14)
N8	0.0443 (17)	0.0466 (16)	0.0444 (18)	−0.0048 (13)	−0.0077 (14)	−0.0066 (13)
O9	0.0517 (15)	0.0545 (16)	0.0429 (15)	−0.0010 (12)	−0.0034 (12)	−0.0102 (11)
O10	0.0581 (19)	0.099 (3)	0.057 (2)	0.0186 (18)	−0.0181 (15)	−0.0192 (18)
S11	0.0507 (5)	0.0251 (4)	0.0345 (4)	−0.0034 (3)	−0.0070 (3)	−0.0042 (3)
O12	0.0654 (16)	0.0265 (11)	0.0396 (13)	−0.0012 (10)	−0.0100 (11)	−0.0060 (9)
O13	0.0526 (14)	0.0363 (12)	0.0413 (13)	−0.0081 (10)	−0.0100 (11)	−0.0034 (9)
C14	0.0437 (17)	0.0263 (14)	0.0310 (15)	−0.0010 (12)	−0.0031 (12)	−0.0058 (11)
C15	0.058 (2)	0.0318 (16)	0.0441 (19)	0.0063 (14)	0.0081 (16)	−0.0039 (13)
C16	0.048 (2)	0.0415 (19)	0.054 (2)	0.0007 (15)	0.0134 (17)	−0.0068 (15)
C17	0.053 (2)	0.0368 (17)	0.0328 (16)	−0.0071 (14)	−0.0052 (14)	−0.0055 (12)
C18	0.0484 (19)	0.0274 (15)	0.0425 (18)	−0.0015 (12)	−0.0042 (14)	−0.0074 (13)
C19	0.0405 (17)	0.0292 (15)	0.0460 (18)	0.0002 (12)	−0.0062 (14)	−0.0062 (13)
C20	0.061 (2)	0.0407 (18)	0.0410 (19)	−0.0146 (16)	−0.0006 (16)	−0.0045 (14)

Geometric parameters (Å, º)

Br1—C4	1.881 (3)	S11—O13	1.430 (3)
N1—C5	1.381 (4)	S11—C14	1.748 (3)
N1—C2	1.399 (4)	C14—C15	1.387 (5)
N1—S11	1.698 (3)	C14—C19	1.389 (4)
C2—C3	1.381 (5)	C15—C16	1.383 (6)
C2—C6	1.441 (5)	C15—H15	0.9500
C3—C4	1.414 (5)	C16—C17	1.390 (5)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.361 (5)	C17—C18	1.385 (5)
C5—H5	0.9500	C17—C20	1.503 (5)
C6—C7	1.318 (6)	C18—C19	1.386 (5)
C6—H6	0.9500	C18—H18	0.9500
C7—N8	1.439 (5)	C19—H19	0.9500
C7—H7	0.9500	C20—H20A	0.9800
N8—O10	1.210 (5)	C20—H20B	0.9800
N8—O9	1.237 (4)	C20—H20C	0.9800
S11—O12	1.428 (2)
C5—N1—C2	109.1 (3)	O12—S11—C14	109.60 (15)
C5—N1—S11	120.8 (2)	O13—S11—C14	109.53 (15)
C2—N1—S11	129.0 (2)	N1—S11—C14	104.67 (14)
C3—C2—N1	107.6 (3)	C15—C14—C19	121.5 (3)
C3—C2—C6	128.1 (3)	C15—C14—S11	119.5 (2)
N1—C2—C6	124.2 (3)	C19—C14—S11	119.0 (3)
C2—C3—C4	106.5 (3)	C16—C15—C14	118.3 (3)
C2—C3—H3	126.8	C16—C15—H15	120.8
C4—C3—H3	126.8	C14—C15—H15	120.8
C5—C4—C3	109.6 (3)	C15—C16—C17	121.9 (4)
C5—C4—Br1	125.7 (3)	C15—C16—H16	119.1
C3—C4—Br1	124.7 (3)	C17—C16—H16	119.1
C4—C5—N1	107.2 (3)	C18—C17—C16	118.1 (3)
C4—C5—H5	126.4	C18—C17—C20	122.2 (3)
N1—C5—H5	126.4	C16—C17—C20	119.7 (3)
C7—C6—C2	122.4 (4)	C17—C18—C19	121.7 (3)
C7—C6—H6	118.8	C17—C18—H18	119.1
C2—C6—H6	118.8	C19—C18—H18	119.1
C6—C7—N8	121.2 (4)	C18—C19—C14	118.4 (3)
C6—C7—H7	119.4	C18—C19—H19	120.8
N8—C7—H7	119.4	C14—C19—H19	120.8
O10—N8—O9	123.7 (3)	C17—C20—H20A	109.5
O10—N8—C7	116.7 (3)	C17—C20—H20B	109.5
O9—N8—C7	119.6 (3)	H20A—C20—H20B	109.5
O12—S11—O13	121.14 (15)	C17—C20—H20C	109.5
O12—S11—N1	106.10 (14)	H20A—C20—H20C	109.5
O13—S11—N1	104.39 (15)	H20B—C20—H20C	109.5
C5—N1—C2—C3	−1.8 (3)	C2—N1—S11—O13	−165.3 (3)
S11—N1—C2—C3	−169.3 (2)	C5—N1—S11—C14	−86.7 (3)
C5—N1—C2—C6	178.8 (3)	C2—N1—S11—C14	79.6 (3)
S11—N1—C2—C6	11.2 (5)	O12—S11—C14—C15	17.3 (3)
N1—C2—C3—C4	1.4 (3)	O13—S11—C14—C15	152.4 (3)
C6—C2—C3—C4	−179.2 (3)	N1—S11—C14—C15	−96.2 (3)
C2—C3—C4—C5	−0.5 (4)	O12—S11—C14—C19	−163.7 (3)
C2—C3—C4—Br1	179.7 (2)	O13—S11—C14—C19	−28.6 (3)
C3—C4—C5—N1	−0.5 (4)	N1—S11—C14—C19	82.9 (3)
Br1—C4—C5—N1	179.2 (2)	C19—C14—C15—C16	0.6 (6)
C2—N1—C5—C4	1.4 (4)	S11—C14—C15—C16	179.6 (3)
S11—N1—C5—C4	170.2 (2)	C14—C15—C16—C17	0.3 (7)
C3—C2—C6—C7	2.4 (6)	C15—C16—C17—C18	−1.5 (6)
N1—C2—C6—C7	−178.3 (3)	C15—C16—C17—C20	179.2 (4)
C2—C6—C7—N8	−179.7 (3)	C16—C17—C18—C19	1.9 (6)
C6—C7—N8—O10	177.7 (4)	C20—C17—C18—C19	−178.8 (3)
C6—C7—N8—O9	−3.0 (6)	C17—C18—C19—C14	−1.0 (5)
C5—N1—S11—O12	157.4 (3)	C15—C14—C19—C18	−0.2 (5)
C2—N1—S11—O12	−36.3 (3)	S11—C14—C19—C18	−179.2 (3)
C5—N1—S11—O13	28.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O10^i	0.95	2.37	3.297 (5)	166
C7—H7···O10^i	0.95	2.41	3.360 (5)	174
C6—H6···O12	0.95	2.29	2.963 (4)	127

Symmetry code: (i) −x, −y+2, −z+1.

6-(4-bromo-1-tosylpyrrol-2-yl)-4,4-dimethyl-5-nitrohexan-2-one (3)

Crystal data

C19H23BrN2O5S	F(000) = 968
Mr = 471.36	Dx = 1.513 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.7375 (2) Å	Cell parameters from 9692 reflections
b = 15.9728 (3) Å	θ = 2.8–46.1°
c = 16.7621 (3) Å	µ = 2.12 mm^−1
β = 93.055 (1)°	T = 100 K
V = 2068.68 (8) Å^3	Block, colorless
Z = 4	0.61 × 0.56 × 0.55 mm

Data collection

Bruker APEXII CCD diffractometer	15578 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.031
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 46.5°, θmin = 1.8°
Tmin = 0.669, Tmax = 0.749	h = −15→15
226885 measured reflections	k = −32→32
18433 independent reflections	l = −34→34

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0366P)^2 + 0.375P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.006
18433 reflections	Δρmax = 0.69 e Å^−3
257 parameters	Δρmin = −0.72 e Å^−3
0 restraints

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
Br1	0.22008 (2)	0.57357 (2)	0.01021 (2)	0.01695 (2)
N1	0.17070 (6)	0.42535 (3)	0.20251 (3)	0.01145 (6)
C3	0.37857 (7)	0.44721 (3)	0.11798 (3)	0.01261 (7)
H3	0.483498	0.444262	0.091152	0.015*
N8	0.44371 (8)	0.23904 (3)	0.11422 (3)	0.01693 (8)
C2	0.33880 (7)	0.40180 (3)	0.18381 (3)	0.01093 (6)
C4	0.23457 (7)	0.49959 (3)	0.09697 (3)	0.01208 (7)
O9	0.57359 (9)	0.27017 (4)	0.08769 (4)	0.02494 (10)
C5	0.10853 (7)	0.48676 (3)	0.14928 (3)	0.01247 (7)
H5	−0.000347	0.514227	0.149476	0.015*
C6	0.45096 (7)	0.33876 (3)	0.22754 (3)	0.01219 (7)
H6A	0.434437	0.344148	0.285479	0.015*
H6B	0.573549	0.351849	0.218744	0.015*
C7	0.41499 (7)	0.24784 (3)	0.20244 (3)	0.01148 (7)
H7	0.290618	0.235381	0.210853	0.014*
O10	0.33578 (10)	0.19916 (4)	0.07358 (3)	0.02730 (12)
C11	0.52787 (7)	0.18170 (3)	0.24936 (3)	0.01285 (7)
C12	0.51170 (9)	0.09560 (4)	0.20840 (4)	0.01678 (9)
H12A	0.566845	0.052934	0.243202	0.025*
H12B	0.568869	0.097269	0.157640	0.025*
H12C	0.389085	0.081793	0.198271	0.025*
C13	0.71998 (8)	0.20658 (4)	0.25676 (5)	0.01915 (10)
H13A	0.786783	0.161943	0.284110	0.029*
H13B	0.732997	0.258568	0.287538	0.029*
H13C	0.762620	0.215080	0.203347	0.029*
C14	0.46432 (8)	0.17737 (4)	0.33473 (3)	0.01491 (8)
H14A	0.542953	0.139094	0.365724	0.018*
H14B	0.479873	0.233710	0.358656	0.018*
C15	0.28132 (9)	0.14997 (4)	0.34817 (4)	0.01594 (8)
O16	0.18406 (7)	0.12067 (4)	0.29612 (3)	0.02047 (8)
C17	0.22683 (13)	0.16059 (6)	0.43234 (5)	0.02768 (15)
H17A	0.322919	0.145112	0.469905	0.042*
H17B	0.127148	0.124460	0.440913	0.042*
H17C	0.194909	0.219124	0.441078	0.042*
S18	0.05660 (2)	0.39646 (2)	0.28052 (2)	0.01139 (2)
O19	−0.11952 (6)	0.41232 (3)	0.25512 (3)	0.01581 (7)
O20	0.11448 (7)	0.31396 (3)	0.30178 (3)	0.01737 (7)
C21	0.11675 (7)	0.46504 (3)	0.35854 (3)	0.01230 (7)
C22	0.04515 (8)	0.54520 (4)	0.35859 (4)	0.01510 (8)
H22	−0.032923	0.562991	0.316297	0.018*
C23	0.09053 (9)	0.59848 (4)	0.42186 (4)	0.01861 (9)
H23	0.043057	0.653310	0.422446	0.022*
C24	0.20469 (9)	0.57294 (4)	0.48466 (4)	0.01888 (10)
C25	0.27117 (9)	0.49166 (5)	0.48363 (4)	0.01981 (10)
H25	0.346580	0.473194	0.526648	0.024*
C26	0.22901 (8)	0.43731 (4)	0.42083 (4)	0.01686 (9)
H26	0.275760	0.382327	0.420358	0.020*
C27	0.25660 (13)	0.63236 (6)	0.55124 (5)	0.02910 (16)
H27A	0.286189	0.600523	0.600043	0.044*
H27B	0.160185	0.670287	0.560580	0.044*
H27C	0.357263	0.665022	0.536490	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01729 (3)	0.02109 (3)	0.01259 (2)	0.00044 (2)	0.00191 (2)	0.00605 (2)
N1	0.01097 (14)	0.01251 (15)	0.01104 (14)	0.00102 (11)	0.00231 (11)	0.00178 (11)
C3	0.01252 (17)	0.01266 (16)	0.01295 (17)	0.00042 (13)	0.00361 (13)	0.00055 (13)
N8	0.0264 (2)	0.01156 (16)	0.01297 (17)	0.00279 (15)	0.00230 (16)	0.00011 (13)
C2	0.01090 (15)	0.00970 (15)	0.01232 (16)	0.00022 (12)	0.00189 (12)	−0.00041 (12)
C4	0.01302 (17)	0.01289 (17)	0.01043 (16)	−0.00009 (13)	0.00146 (13)	0.00130 (13)
O9	0.0316 (3)	0.0223 (2)	0.0222 (2)	0.00315 (19)	0.0137 (2)	0.00241 (17)
C5	0.01182 (16)	0.01417 (17)	0.01151 (17)	0.00155 (13)	0.00149 (13)	0.00201 (13)
C6	0.01206 (16)	0.00977 (15)	0.01461 (18)	0.00011 (12)	−0.00042 (13)	−0.00072 (13)
C7	0.01306 (16)	0.00962 (15)	0.01172 (16)	0.00006 (12)	0.00023 (13)	−0.00016 (12)
O10	0.0448 (3)	0.0210 (2)	0.01518 (19)	−0.0039 (2)	−0.0072 (2)	−0.00253 (16)
C11	0.01313 (17)	0.01012 (16)	0.01516 (19)	0.00026 (13)	−0.00073 (14)	0.00104 (13)
C12	0.0209 (2)	0.01018 (17)	0.0193 (2)	0.00159 (16)	0.00143 (18)	−0.00047 (15)
C13	0.01240 (18)	0.0166 (2)	0.0282 (3)	0.00095 (16)	−0.00065 (18)	0.00158 (19)
C14	0.0173 (2)	0.01399 (18)	0.01306 (18)	−0.00250 (15)	−0.00284 (15)	0.00117 (14)
C15	0.0216 (2)	0.01344 (18)	0.01275 (18)	−0.00542 (16)	0.00065 (16)	0.00065 (14)
O16	0.0214 (2)	0.0228 (2)	0.01716 (18)	−0.01001 (16)	0.00056 (15)	−0.00288 (15)
C17	0.0392 (4)	0.0296 (3)	0.0148 (2)	−0.0130 (3)	0.0068 (2)	−0.0009 (2)
S18	0.01086 (4)	0.01178 (4)	0.01174 (5)	−0.00151 (3)	0.00243 (3)	0.00137 (3)
O19	0.01000 (13)	0.02075 (17)	0.01676 (17)	−0.00281 (12)	0.00140 (12)	0.00022 (13)
O20	0.02110 (18)	0.01187 (14)	0.01957 (18)	0.00005 (13)	0.00506 (15)	0.00389 (13)
C21	0.01169 (16)	0.01488 (18)	0.01041 (16)	−0.00063 (13)	0.00135 (13)	0.00141 (13)
C22	0.01588 (19)	0.01612 (19)	0.01330 (18)	0.00146 (15)	0.00080 (15)	−0.00038 (15)
C23	0.0214 (2)	0.0188 (2)	0.0158 (2)	−0.00135 (19)	0.00307 (18)	−0.00325 (17)
C24	0.0201 (2)	0.0256 (3)	0.01121 (19)	−0.0081 (2)	0.00354 (16)	−0.00192 (17)
C25	0.0190 (2)	0.0281 (3)	0.01208 (19)	−0.0051 (2)	−0.00187 (17)	0.00301 (18)
C26	0.0164 (2)	0.0205 (2)	0.01350 (19)	0.00019 (17)	−0.00121 (16)	0.00393 (16)
C27	0.0358 (4)	0.0369 (4)	0.0150 (2)	−0.0168 (3)	0.0046 (2)	−0.0071 (2)

Geometric parameters (Å, º)

Br1—C4	1.8727 (5)	C13—H13C	0.9800
N1—C5	1.3942 (7)	C14—C15	1.5103 (9)
N1—C2	1.4054 (7)	C14—H14A	0.9900
N1—S18	1.6808 (5)	C14—H14B	0.9900
C3—C2	1.3692 (7)	C15—O16	1.2150 (8)
C3—C4	1.4226 (8)	C15—C17	1.5036 (10)
C3—H3	0.9500	C17—H17A	0.9800
N8—O9	1.2258 (9)	C17—H17B	0.9800
N8—O10	1.2275 (8)	C17—H17C	0.9800
N8—C7	1.5135 (7)	S18—O19	1.4285 (5)
C2—C6	1.4954 (7)	S18—O20	1.4307 (5)
C4—C5	1.3613 (8)	S18—C21	1.7499 (6)
C5—H5	0.9500	C21—C26	1.3944 (8)
C6—C7	1.5333 (7)	C21—C22	1.3951 (8)
C6—H6A	0.9900	C22—C23	1.3902 (9)
C6—H6B	0.9900	C22—H22	0.9500
C7—C11	1.5571 (7)	C23—C24	1.3984 (10)
C7—H7	1.0000	C23—H23	0.9500
C11—C13	1.5372 (8)	C24—C25	1.3970 (11)
C11—C12	1.5392 (8)	C24—C27	1.5033 (10)
C11—C14	1.5392 (8)	C25—C26	1.3898 (10)
C12—H12A	0.9800	C25—H25	0.9500
C12—H12B	0.9800	C26—H26	0.9500
C12—H12C	0.9800	C27—H27A	0.9800
C13—H13A	0.9800	C27—H27B	0.9800
C13—H13B	0.9800	C27—H27C	0.9800
C5—N1—C2	109.72 (4)	H13B—C13—H13C	109.5
C5—N1—S18	120.89 (4)	C15—C14—C11	120.01 (5)
C2—N1—S18	129.11 (4)	C15—C14—H14A	107.3
C2—C3—C4	107.72 (5)	C11—C14—H14A	107.3
C2—C3—H3	126.1	C15—C14—H14B	107.3
C4—C3—H3	126.1	C11—C14—H14B	107.3
O9—N8—O10	123.76 (6)	H14A—C14—H14B	106.9
O9—N8—C7	118.87 (6)	O16—C15—C17	121.55 (6)
O10—N8—C7	117.35 (6)	O16—C15—C14	123.66 (6)
C3—C2—N1	106.76 (4)	C17—C15—C14	114.78 (6)
C3—C2—C6	127.03 (5)	C15—C17—H17A	109.5
N1—C2—C6	126.21 (5)	C15—C17—H17B	109.5
C5—C4—C3	109.30 (5)	H17A—C17—H17B	109.5
C5—C4—Br1	125.45 (4)	C15—C17—H17C	109.5
C3—C4—Br1	125.24 (4)	H17A—C17—H17C	109.5
C4—C5—N1	106.47 (5)	H17B—C17—H17C	109.5
C4—C5—H5	126.8	O19—S18—O20	121.24 (3)
N1—C5—H5	126.8	O19—S18—N1	104.58 (3)
C2—C6—C7	114.27 (4)	O20—S18—N1	106.03 (3)
C2—C6—H6A	108.7	O19—S18—C21	108.85 (3)
C7—C6—H6A	108.7	O20—S18—C21	108.86 (3)
C2—C6—H6B	108.7	N1—S18—C21	106.24 (2)
C7—C6—H6B	108.7	C26—C21—C22	121.51 (5)
H6A—C6—H6B	107.6	C26—C21—S18	119.41 (5)
N8—C7—C6	108.79 (4)	C22—C21—S18	119.02 (4)
N8—C7—C11	108.84 (4)	C23—C22—C21	118.56 (6)
C6—C7—C11	114.54 (4)	C23—C22—H22	120.7
N8—C7—H7	108.2	C21—C22—H22	120.7
C6—C7—H7	108.2	C22—C23—C24	121.30 (6)
C11—C7—H7	108.2	C22—C23—H23	119.4
C13—C11—C12	108.80 (5)	C24—C23—H23	119.4
C13—C11—C14	106.98 (5)	C25—C24—C23	118.69 (6)
C12—C11—C14	110.62 (5)	C25—C24—C27	120.79 (7)
C13—C11—C7	112.29 (5)	C23—C24—C27	120.51 (7)
C12—C11—C7	110.53 (4)	C26—C25—C24	121.21 (6)
C14—C11—C7	107.56 (4)	C26—C25—H25	119.4
C11—C12—H12A	109.5	C24—C25—H25	119.4
C11—C12—H12B	109.5	C25—C26—C21	118.72 (6)
H12A—C12—H12B	109.5	C25—C26—H26	120.6
C11—C12—H12C	109.5	C21—C26—H26	120.6
H12A—C12—H12C	109.5	C24—C27—H27A	109.5
H12B—C12—H12C	109.5	C24—C27—H27B	109.5
C11—C13—H13A	109.5	H27A—C27—H27B	109.5
C11—C13—H13B	109.5	C24—C27—H27C	109.5
H13A—C13—H13B	109.5	H27A—C27—H27C	109.5
C11—C13—H13C	109.5	H27B—C27—H27C	109.5
H13A—C13—H13C	109.5
C4—C3—C2—N1	0.72 (6)	C12—C11—C14—C15	−58.53 (7)
C4—C3—C2—C6	−179.65 (5)	C7—C11—C14—C15	62.27 (6)
C5—N1—C2—C3	−1.40 (6)	C11—C14—C15—O16	9.44 (9)
S18—N1—C2—C3	−175.24 (4)	C11—C14—C15—C17	−171.28 (6)
C5—N1—C2—C6	178.97 (5)	C5—N1—S18—O19	27.62 (5)
S18—N1—C2—C6	5.13 (8)	C2—N1—S18—O19	−159.14 (5)
C2—C3—C4—C5	0.21 (7)	C5—N1—S18—O20	156.84 (5)
C2—C3—C4—Br1	−179.12 (4)	C2—N1—S18—O20	−29.92 (6)
C3—C4—C5—N1	−1.05 (6)	C5—N1—S18—C21	−87.44 (5)
Br1—C4—C5—N1	178.27 (4)	C2—N1—S18—C21	85.80 (5)
C2—N1—C5—C4	1.52 (6)	O19—S18—C21—C26	144.02 (5)
S18—N1—C5—C4	175.95 (4)	O20—S18—C21—C26	9.94 (6)
C3—C2—C6—C7	−96.18 (6)	N1—S18—C21—C26	−103.86 (5)
N1—C2—C6—C7	83.39 (7)	O19—S18—C21—C22	−33.26 (5)
O9—N8—C7—C6	45.57 (7)	O20—S18—C21—C22	−167.34 (5)
O10—N8—C7—C6	−135.92 (6)	N1—S18—C21—C22	78.86 (5)
O9—N8—C7—C11	−79.85 (6)	C26—C21—C22—C23	1.22 (9)
O10—N8—C7—C11	98.66 (6)	S18—C21—C22—C23	178.44 (5)
C2—C6—C7—N8	59.57 (6)	C21—C22—C23—C24	−0.29 (10)
C2—C6—C7—C11	−178.41 (5)	C22—C23—C24—C25	−1.06 (10)
N8—C7—C11—C13	76.03 (6)	C22—C23—C24—C27	178.05 (6)
C6—C7—C11—C13	−45.96 (7)	C23—C24—C25—C26	1.54 (10)
N8—C7—C11—C12	−45.66 (6)	C27—C24—C25—C26	−177.57 (7)
C6—C7—C11—C12	−167.66 (5)	C24—C25—C26—C21	−0.65 (10)
N8—C7—C11—C14	−166.52 (4)	C22—C21—C26—C25	−0.76 (9)
C6—C7—C11—C14	71.48 (6)	S18—C21—C26—C25	−177.96 (5)
C13—C11—C14—C15	−176.89 (5)