Crystal structure and Hirshfeld surface analysis of N-(2-chloro­phenyl­carbamo­thio­yl)-4-fluoro­benzamide and N-(4-bromo­phenyl­carbamo­thio­yl)-4-fluoro­benzamide

The title compounds, C₁₄H₁₀ClFN₂OS (1) and C₁₄H₁₀BrFN₂OS (2), were synthesized by two-step reactions·In the crystal of 1, inversion dimers linked by pairs of N—H...S hydrogen bonds generate (8) loops. The extended structure of 2 features the same motif but an additional weak C—H...S inter­action links the inversion dimers into [100] double columns

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.025
• wR factor = 0.069
• Data-to-parameter ratio = 12.5

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.025
• wR factor = 0.110
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1       --C8       .        6.5 s.u.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         43 Report

Alert level G
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl       ..F1               3.12 Ang.
                                           1-x,-1/2+y,1/2-z  =      2_645 Check
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 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
   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         33 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          9 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  S1       ..C1               3.26 Ang.
                                                 1-x,1-y,-z  =      2_665 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br1      ..Br1              3.38 Ang.
                                                -1-x,-y,1-z  =      2_456 Check
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Info

   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

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

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

N-(2-Chlorophenylcarbamothioyl)-4-fluorobenzamide (1)

Crystal data

C14H10ClFN2OS	F(000) = 632
Mr = 308.75	Dx = 1.563 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 8.0785 (2) Å	Cell parameters from 9977 reflections
b = 12.4230 (3) Å	θ = 4.9–68.3°
c = 13.0772 (3) Å	µ = 4.15 mm^−1
β = 90.551 (1)°	T = 100 K
V = 1312.36 (5) Å^3	Prism, colourless
Z = 4	0.11 × 0.07 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer	2269 reflections with I > 2σ(I)
ω scans	Rint = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2000)	θmax = 68.3°, θmin = 4.9°
Tmin = 0.682, Tmax = 0.895	h = −9→9
18686 measured reflections	k = −14→14
2362 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0347P)^2 + 0.7594P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2362 reflections	Δρmax = 0.22 e Å^−3
189 parameters	Δρmin = −0.24 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
S1	0.73325 (5)	0.47025 (3)	0.56374 (3)	0.02331 (12)
Cl	0.83162 (5)	0.03157 (3)	0.58416 (3)	0.02495 (11)
F1	0.18907 (12)	0.30493 (8)	0.01782 (7)	0.0314 (2)
O1	0.54889 (12)	0.15637 (8)	0.42244 (7)	0.0192 (2)
N1	0.56777 (15)	0.33824 (10)	0.44484 (9)	0.0179 (3)
N2	0.70992 (14)	0.25311 (9)	0.57516 (9)	0.0157 (2)
C1	0.43467 (17)	0.36712 (11)	0.24179 (10)	0.0177 (3)
H1	0.493438	0.425890	0.271153	0.021*
C2	0.35330 (18)	0.38022 (12)	0.14870 (11)	0.0206 (3)
H2	0.355095	0.447218	0.113699	0.025*
C3	0.26979 (18)	0.29291 (12)	0.10866 (10)	0.0211 (3)
C4	0.26446 (18)	0.19359 (12)	0.15557 (11)	0.0224 (3)
H4	0.206152	0.135158	0.125243	0.027*
C5	0.34669 (18)	0.18165 (11)	0.24822 (11)	0.0199 (3)
H5	0.345811	0.113881	0.281860	0.024*
C6	0.43099 (16)	0.26820 (11)	0.29281 (10)	0.0156 (3)
C7	0.51917 (16)	0.24761 (11)	0.39152 (10)	0.0160 (3)
C8	0.67071 (16)	0.34671 (11)	0.53083 (10)	0.0162 (3)
C9	0.80473 (16)	0.23264 (11)	0.66453 (10)	0.0148 (3)
C10	0.83157 (17)	0.30697 (11)	0.74300 (10)	0.0184 (3)
H10	0.789298	0.378033	0.736600	0.022*
C11	0.91962 (17)	0.27772 (12)	0.83031 (11)	0.0213 (3)
H11	0.938625	0.329427	0.882642	0.026*
C12	0.98017 (18)	0.17407 (12)	0.84215 (11)	0.0224 (3)
H12	1.040289	0.154849	0.902214	0.027*
C13	0.95246 (18)	0.09856 (12)	0.76576 (11)	0.0217 (3)
H13	0.992398	0.027057	0.773432	0.026*
C14	0.86603 (17)	0.12824 (11)	0.67813 (10)	0.0170 (3)
H1B	0.672 (2)	0.1970 (16)	0.5432 (14)	0.028 (5)*
H1A	0.528 (2)	0.3988 (16)	0.4260 (14)	0.031 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0331 (2)	0.01172 (18)	0.0249 (2)	−0.00054 (13)	−0.01311 (15)	−0.00095 (12)
Cl	0.0406 (2)	0.01417 (18)	0.01996 (19)	0.00501 (14)	−0.00550 (15)	−0.00194 (12)
F1	0.0374 (5)	0.0388 (5)	0.0178 (4)	0.0005 (4)	−0.0147 (4)	0.0016 (4)
O1	0.0267 (5)	0.0138 (5)	0.0170 (5)	−0.0006 (4)	−0.0048 (4)	0.0011 (4)
N1	0.0248 (6)	0.0126 (6)	0.0161 (6)	0.0039 (5)	−0.0079 (5)	−0.0007 (4)
N2	0.0206 (6)	0.0125 (6)	0.0141 (6)	0.0000 (5)	−0.0046 (4)	−0.0015 (4)
C1	0.0208 (7)	0.0165 (6)	0.0158 (7)	0.0002 (5)	−0.0008 (5)	−0.0019 (5)
C2	0.0257 (7)	0.0196 (7)	0.0166 (7)	0.0034 (6)	−0.0016 (6)	0.0024 (5)
C3	0.0209 (7)	0.0304 (8)	0.0119 (7)	0.0041 (6)	−0.0042 (5)	−0.0015 (6)
C4	0.0241 (7)	0.0243 (8)	0.0188 (7)	−0.0040 (6)	−0.0045 (6)	−0.0048 (6)
C5	0.0240 (7)	0.0170 (7)	0.0187 (7)	−0.0012 (6)	−0.0017 (5)	−0.0007 (5)
C6	0.0158 (6)	0.0171 (7)	0.0137 (6)	0.0017 (5)	−0.0004 (5)	−0.0012 (5)
C7	0.0171 (6)	0.0152 (7)	0.0158 (7)	0.0000 (5)	−0.0002 (5)	−0.0011 (5)
C8	0.0184 (6)	0.0150 (6)	0.0152 (6)	0.0020 (5)	−0.0023 (5)	−0.0010 (5)
C9	0.0139 (6)	0.0169 (6)	0.0135 (6)	−0.0009 (5)	−0.0008 (5)	0.0022 (5)
C10	0.0208 (7)	0.0169 (7)	0.0175 (7)	−0.0002 (5)	−0.0020 (5)	−0.0003 (5)
C11	0.0221 (7)	0.0250 (7)	0.0167 (7)	−0.0030 (6)	−0.0034 (5)	−0.0019 (6)
C12	0.0211 (7)	0.0292 (8)	0.0169 (7)	0.0001 (6)	−0.0055 (5)	0.0048 (6)
C13	0.0226 (7)	0.0211 (7)	0.0215 (7)	0.0039 (6)	−0.0024 (6)	0.0053 (6)
C14	0.0189 (6)	0.0160 (7)	0.0161 (6)	0.0000 (5)	−0.0001 (5)	−0.0007 (5)

Geometric parameters (Å, º)

S1—C8	1.6709 (14)	C4—C5	1.384 (2)
Cl—C14	1.7387 (14)	C4—H4	0.9500
F1—C3	1.3579 (16)	C5—C6	1.3972 (19)
O1—C7	1.2264 (17)	C5—H5	0.9500
N1—C7	1.3794 (18)	C6—C7	1.4904 (18)
N1—C8	1.3961 (17)	C9—C10	1.3959 (19)
N1—H1A	0.85 (2)	C9—C14	1.3990 (19)
N2—C8	1.3360 (18)	C10—C11	1.3879 (19)
N2—C9	1.4141 (17)	C10—H10	0.9500
N2—H1B	0.87 (2)	C11—C12	1.385 (2)
C1—C2	1.3875 (19)	C11—H11	0.9500
C1—C6	1.3987 (19)	C12—C13	1.387 (2)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.378 (2)	C13—C14	1.3860 (19)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.379 (2)
C7—N1—C8	129.28 (12)	O1—C7—N1	122.26 (12)
C7—N1—H1A	117.8 (13)	O1—C7—C6	122.32 (12)
C8—N1—H1A	112.8 (13)	N1—C7—C6	115.41 (12)
C8—N2—C9	129.75 (12)	N2—C8—N1	114.89 (12)
C8—N2—H1B	114.1 (12)	N2—C8—S1	128.15 (10)
C9—N2—H1B	116.1 (12)	N1—C8—S1	116.94 (10)
C2—C1—C6	120.64 (13)	C10—C9—C14	117.87 (12)
C2—C1—H1	119.7	C10—C9—N2	124.58 (12)
C6—C1—H1	119.7	C14—C9—N2	117.39 (12)
C3—C2—C1	117.84 (13)	C11—C10—C9	120.42 (13)
C3—C2—H2	121.1	C11—C10—H10	119.8
C1—C2—H2	121.1	C9—C10—H10	119.8
F1—C3—C2	118.37 (13)	C12—C11—C10	120.86 (13)
F1—C3—C4	118.09 (13)	C12—C11—H11	119.6
C2—C3—C4	123.54 (13)	C10—C11—H11	119.6
C3—C4—C5	117.94 (13)	C11—C12—C13	119.58 (13)
C3—C4—H4	121.0	C11—C12—H12	120.2
C5—C4—H4	121.0	C13—C12—H12	120.2
C4—C5—C6	120.72 (13)	C14—C13—C12	119.47 (13)
C4—C5—H5	119.6	C14—C13—H13	120.3
C6—C5—H5	119.6	C12—C13—H13	120.3
C5—C6—C1	119.30 (12)	C13—C14—C9	121.78 (13)
C5—C6—C7	117.15 (12)	C13—C14—Cl	118.45 (11)
C1—C6—C7	123.49 (12)	C9—C14—Cl	119.76 (10)
C6—C1—C2—C3	−0.1 (2)	C9—N2—C8—S1	4.5 (2)
C1—C2—C3—F1	179.70 (12)	C7—N1—C8—N2	−9.6 (2)
C1—C2—C3—C4	−0.7 (2)	C7—N1—C8—S1	168.84 (11)
F1—C3—C4—C5	−179.92 (12)	C8—N2—C9—C10	22.4 (2)
C2—C3—C4—C5	0.5 (2)	C8—N2—C9—C14	−162.20 (13)
C3—C4—C5—C6	0.6 (2)	C14—C9—C10—C11	1.4 (2)
C4—C5—C6—C1	−1.3 (2)	N2—C9—C10—C11	176.73 (13)
C4—C5—C6—C7	−178.72 (13)	C9—C10—C11—C12	−1.1 (2)
C2—C1—C6—C5	1.1 (2)	C10—C11—C12—C13	0.0 (2)
C2—C1—C6—C7	178.32 (13)	C11—C12—C13—C14	0.7 (2)
C8—N1—C7—O1	8.6 (2)	C12—C13—C14—C9	−0.3 (2)
C8—N1—C7—C6	−170.22 (13)	C12—C13—C14—Cl	−179.45 (11)
C5—C6—C7—O1	15.54 (19)	C10—C9—C14—C13	−0.7 (2)
C1—C6—C7—O1	−161.73 (13)	N2—C9—C14—C13	−176.39 (12)
C5—C6—C7—N1	−165.60 (12)	C10—C9—C14—Cl	178.42 (10)
C1—C6—C7—N1	17.14 (19)	N2—C9—C14—Cl	2.72 (17)
C9—N2—C8—N1	−177.23 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···S1	0.95	2.57	3.1945 (14)	124
N2—H1B···Cl	0.87 (2)	2.482 (19)	2.9246 (12)	112.3 (14)
N2—H1B···O1	0.87 (2)	1.924 (19)	2.6600 (14)	141.6 (17)
N1—H1A···S1^i	0.85 (2)	2.67 (2)	3.4031 (13)	145.2 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

N-(4-Bromophenylcarbamothioyl)-4-fluorobenzamide (2)

Crystal data

C14H10BrFN2OS	Z = 2
Mr = 353.19	F(000) = 348
Triclinic, P1	Dx = 1.771 Mg m^−3
a = 3.8733 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 13.0776 (5) Å	Cell parameters from 9945 reflections
c = 13.2628 (6) Å	θ = 3.4–68.2°
α = 98.817 (1)°	µ = 5.83 mm^−1
β = 94.714 (1)°	T = 100 K
γ = 94.727 (1)°	Plate, colourless
V = 658.54 (5) Å^3	0.35 × 0.05 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer	2381 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.025
Absorption correction: multi-scan (SADABS; Bruker, 2000)	θmax = 68.2°, θmin = 3.4°
Tmin = 0.612, Tmax = 0.946	h = −4→4
20701 measured reflections	k = −15→15
2384 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
2384 reflections	Δρmax = 0.45 e Å^−3
181 parameters	Δρmin = −1.46 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	−0.39350 (4)	0.11758 (2)	0.46689 (2)	0.01272 (16)
O1	0.4560 (4)	0.66092 (11)	0.32207 (10)	0.0175 (3)
N1	0.3835 (4)	0.58122 (12)	0.15534 (11)	0.0106 (3)
H1A	0.419261	0.590591	0.092584	0.013*
N2	0.1544 (4)	0.47331 (12)	0.26027 (11)	0.0111 (3)
H1B	0.187274	0.531645	0.304308	0.013*
F1	0.9679 (3)	1.04344 (9)	0.12214 (9)	0.0205 (3)
S1	0.18617 (10)	0.38973 (3)	0.06266 (3)	0.00989 (18)
C1	0.5195 (4)	0.78724 (14)	0.09959 (14)	0.0092 (4)
H1	0.376290	0.737919	0.050359	0.011*
C2	0.6398 (5)	0.88103 (14)	0.07394 (14)	0.0129 (4)
H2	0.581012	0.896819	0.007460	0.016*
C3	0.8466 (5)	0.95143 (15)	0.14634 (15)	0.0146 (4)
C4	0.9345 (5)	0.93323 (14)	0.24544 (14)	0.0137 (4)
H4	1.074144	0.983856	0.294279	0.016*
C5	0.8117 (5)	0.83897 (14)	0.27036 (14)	0.0116 (4)
H5	0.866416	0.824564	0.337592	0.014*
C6	0.6063 (5)	0.76392 (14)	0.19744 (13)	0.0101 (4)
C7	0.4782 (5)	0.66558 (14)	0.23084 (14)	0.0105 (4)
C9	0.0233 (4)	0.38653 (13)	0.30136 (13)	0.0086 (4)
C8	0.2378 (4)	0.48253 (14)	0.16562 (13)	0.0085 (4)
C10	−0.1837 (5)	0.30056 (14)	0.24536 (13)	0.0115 (4)
H10	−0.240925	0.296827	0.173769	0.014*
C11	−0.3051 (4)	0.22064 (14)	0.29513 (13)	0.0105 (4)
H11	−0.444455	0.161739	0.257544	0.013*
C12	−0.2224 (5)	0.22707 (13)	0.39998 (14)	0.0102 (4)
C13	−0.0217 (5)	0.31221 (13)	0.45694 (13)	0.0109 (4)
H13	0.031180	0.315998	0.528723	0.013*
C14	0.0999 (5)	0.39136 (15)	0.40755 (14)	0.0114 (4)
H14	0.237633	0.450144	0.445916	0.014*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0169 (2)	0.0096 (2)	0.0125 (2)	−0.00227 (13)	0.00215 (13)	0.00588 (13)
O1	0.0312 (8)	0.0122 (7)	0.0076 (7)	−0.0065 (6)	0.0033 (6)	0.0011 (5)
N1	0.0154 (8)	0.0108 (8)	0.0057 (7)	0.0005 (6)	0.0007 (6)	0.0022 (6)
N2	0.0170 (8)	0.0073 (7)	0.0090 (7)	−0.0001 (6)	0.0021 (6)	0.0019 (6)
F1	0.0328 (7)	0.0078 (6)	0.0213 (7)	−0.0054 (5)	0.0078 (5)	0.0051 (5)
S1	0.0140 (3)	0.0082 (3)	0.0069 (3)	−0.00094 (19)	0.00084 (19)	0.00050 (19)
C1	0.0092 (8)	0.0080 (9)	0.0102 (8)	−0.0004 (6)	0.0023 (6)	0.0005 (7)
C2	0.0161 (9)	0.0103 (9)	0.0133 (9)	0.0022 (7)	0.0031 (7)	0.0031 (7)
C3	0.0197 (9)	0.0068 (9)	0.0194 (10)	0.0022 (7)	0.0119 (8)	0.0033 (7)
C4	0.0149 (9)	0.0097 (9)	0.0148 (9)	−0.0026 (7)	0.0020 (7)	−0.0021 (7)
C5	0.0144 (8)	0.0095 (9)	0.0093 (8)	−0.0016 (7)	−0.0006 (7)	−0.0012 (7)
C6	0.0106 (8)	0.0103 (9)	0.0089 (9)	−0.0002 (7)	0.0008 (6)	0.0008 (7)
C7	0.0118 (8)	0.0104 (9)	0.0098 (9)	−0.0013 (7)	0.0013 (6)	0.0037 (7)
C9	0.0120 (8)	0.0070 (9)	0.0086 (8)	0.0005 (7)	0.0048 (6)	0.0047 (6)
C8	0.0103 (8)	0.0086 (8)	0.0071 (8)	0.0020 (7)	−0.0002 (6)	0.0026 (6)
C10	0.0137 (8)	0.0120 (9)	0.0088 (8)	0.0001 (7)	−0.0005 (7)	0.0028 (6)
C11	0.0116 (8)	0.0092 (9)	0.0097 (8)	−0.0028 (6)	0.0007 (6)	0.0004 (6)
C12	0.0128 (8)	0.0080 (9)	0.0112 (8)	0.0005 (6)	0.0023 (7)	0.0056 (6)
C13	0.0138 (8)	0.0132 (9)	0.0067 (8)	−0.0003 (7)	0.0018 (7)	0.0048 (6)
C14	0.0130 (8)	0.0092 (9)	0.0112 (9)	−0.0007 (6)	0.0011 (7)	0.0002 (6)

Geometric parameters (Å, º)

Br1—C12	1.8991 (17)	C4—C5	1.382 (3)
O1—C7	1.230 (2)	C4—H4	0.9500
N1—C7	1.374 (2)	C5—C6	1.409 (2)
N1—C8	1.396 (2)	C5—H5	0.9500
N1—H1A	0.8800	C6—C7	1.484 (3)
N2—C8	1.342 (2)	C9—C10	1.399 (2)
N2—C9	1.408 (2)	C9—C14	1.406 (3)
N2—H1B	0.8800	C10—C11	1.390 (3)
F1—C3	1.350 (2)	C10—H10	0.9500
S1—C8	1.6687 (18)	C11—C12	1.389 (2)
C1—C2	1.377 (3)	C11—H11	0.9500
C1—C6	1.399 (3)	C12—C13	1.385 (3)
C1—H1	0.9500	C13—C14	1.379 (3)
C2—C3	1.375 (3)	C13—H13	0.9500
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.391 (3)
C7—N1—C8	128.20 (16)	O1—C7—N1	122.08 (17)
C7—N1—H1A	115.9	O1—C7—C6	121.00 (17)
C8—N1—H1A	115.9	N1—C7—C6	116.92 (16)
C8—N2—C9	131.19 (16)	C10—C9—C14	119.30 (16)
C8—N2—H1B	114.4	C10—C9—N2	124.87 (15)
C9—N2—H1B	114.4	C14—C9—N2	115.78 (16)
C2—C1—C6	120.62 (17)	N2—C8—N1	114.66 (16)
C2—C1—H1	119.7	N2—C8—S1	126.92 (15)
C6—C1—H1	119.7	N1—C8—S1	118.43 (13)
C3—C2—C1	118.79 (17)	C11—C10—C9	119.57 (16)
C3—C2—H2	120.6	C11—C10—H10	120.2
C1—C2—H2	120.6	C9—C10—H10	120.2
F1—C3—C2	119.46 (18)	C12—C11—C10	119.85 (16)
F1—C3—C4	117.55 (18)	C12—C11—H11	120.1
C2—C3—C4	122.98 (18)	C10—C11—H11	120.1
C5—C4—C3	117.70 (18)	C13—C12—C11	121.42 (16)
C5—C4—H4	121.1	C13—C12—Br1	119.31 (13)
C3—C4—H4	121.1	C11—C12—Br1	119.27 (13)
C4—C5—C6	120.91 (18)	C14—C13—C12	118.76 (16)
C4—C5—H5	119.5	C14—C13—H13	120.6
C6—C5—H5	119.5	C12—C13—H13	120.6
C1—C6—C5	118.97 (17)	C13—C14—C9	121.10 (17)
C1—C6—C7	123.33 (17)	C13—C14—H14	119.5
C5—C6—C7	117.62 (16)	C9—C14—H14	119.5
C6—C1—C2—C3	−0.1 (3)	C8—N2—C9—C10	−28.7 (3)
C1—C2—C3—F1	179.66 (16)	C8—N2—C9—C14	154.04 (18)
C1—C2—C3—C4	−1.4 (3)	C9—N2—C8—N1	−175.93 (16)
F1—C3—C4—C5	−179.80 (16)	C9—N2—C8—S1	3.8 (3)
C2—C3—C4—C5	1.2 (3)	C7—N1—C8—N2	6.3 (3)
C3—C4—C5—C6	0.4 (3)	C7—N1—C8—S1	−173.53 (14)
C2—C1—C6—C5	1.6 (3)	C14—C9—C10—C11	−1.1 (3)
C2—C1—C6—C7	178.38 (16)	N2—C9—C10—C11	−178.32 (16)
C4—C5—C6—C1	−1.8 (3)	C9—C10—C11—C12	0.5 (3)
C4—C5—C6—C7	−178.72 (16)	C10—C11—C12—C13	0.4 (3)
C8—N1—C7—O1	3.4 (3)	C10—C11—C12—Br1	179.54 (13)
C8—N1—C7—C6	−176.01 (16)	C11—C12—C13—C14	−0.6 (3)
C1—C6—C7—O1	−154.97 (17)	Br1—C12—C13—C14	−179.76 (13)
C5—C6—C7—O1	21.9 (3)	C12—C13—C14—C9	0.0 (3)
C1—C6—C7—N1	24.4 (2)	C10—C9—C14—C13	0.9 (3)
C5—C6—C7—N1	−158.75 (16)	N2—C9—C14—C13	178.36 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1^i	0.88	2.69	3.5081 (15)	154
N2—H1B···O1	0.88	1.88	2.610 (2)	139
C10—H10···S1	0.95	2.65	3.2319 (18)	120
C1—H1···S1^ii	0.95	2.81	3.7312 (18)	165

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