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In the mol­ecule of the title compound, C16H16BrNO4, the dihedral angle between the planes of the two rings is 16.6 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014486/jh2009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014486/jh2009Isup2.hkl
Contains datablock I

CCDC reference: 608429

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.038
  • wR factor = 0.090
  • Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 2107 Count of symmetry unique reflns 2112 Completeness (_total/calc) 99.76% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97; program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: please provide; software used to prepare material for publication: CrystalStructure.

4-Bromo-N-(3,4,5-trimethoxyphenyl)benzamide top
Crystal data top
C16H16BrNO4F(000) = 744.00
Mr = 366.21Dx = 1.537 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2abCell parameters from 11047 reflections
a = 7.121 (3) Åθ = 3.1–27.5°
b = 8.492 (3) ŵ = 2.62 mm1
c = 26.171 (7) ÅT = 296 K
V = 1582.6 (9) Å3Block, colorless
Z = 40.30 × 0.30 × 0.28 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1154 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.060
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.456, Tmax = 0.480k = 1011
15633 measured reflectionsl = 3233
2107 independent reflections
Refinement top
Refinement on F2 w = 1/[1.0900σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.038(Δ/σ)max < 0.001
wR(F2) = 0.090Δρmax = 0.55 e Å3
S = 1.00Δρmin = 0.51 e Å3
2107 reflectionsExtinction correction: Larson (1970), equation 22
209 parametersExtinction coefficient: 168 (28)
H-atom parameters constrained
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.44284 (10)0.66745 (6)0.46801 (2)0.1003 (2)
O110.324 (2)0.2189 (8)0.4192 (4)0.076 (3)0.50
O20.6756 (5)0.2287 (3)0.19741 (9)0.0681 (10)
O30.9146 (5)0.0488 (3)0.24860 (11)0.0601 (10)
O40.9066 (5)0.0348 (3)0.35116 (11)0.0778 (12)
O120.375 (2)0.2747 (12)0.4326 (4)0.084 (3)0.50
N10.3647 (5)0.3834 (4)0.35329 (12)0.0576 (12)
C10.2871 (8)0.3487 (5)0.39889 (17)0.0709 (18)
C20.5122 (7)0.3017 (4)0.32860 (14)0.0534 (14)
C30.5218 (6)0.3113 (4)0.27546 (12)0.0488 (12)
C40.6580 (6)0.2315 (5)0.25006 (13)0.0476 (13)
C50.7865 (6)0.1386 (5)0.27545 (14)0.0478 (13)
C60.7742 (7)0.1319 (5)0.32864 (17)0.0565 (15)
C70.6403 (7)0.2123 (5)0.35534 (14)0.0539 (14)
C80.5862 (9)0.3466 (5)0.16953 (16)0.091 (2)
C91.0932 (8)0.1228 (6)0.24731 (19)0.082 (2)
C100.9055 (9)0.0219 (5)0.40477 (17)0.087 (2)
C110.1135 (7)0.4332 (5)0.41397 (14)0.0556 (14)
C120.0431 (8)0.4052 (5)0.46224 (13)0.0685 (16)
C130.1210 (8)0.4754 (5)0.47798 (14)0.0673 (17)
C140.2183 (7)0.5713 (5)0.44556 (16)0.0655 (16)
C150.1497 (9)0.6000 (6)0.39740 (17)0.0766 (18)
C160.0152 (8)0.5299 (6)0.38222 (16)0.0762 (19)
H30.43630.37380.25790.059*
H130.16840.45700.51050.081*
H120.10960.33970.48420.082*
H160.06240.55090.34980.092*
H150.21670.66590.37560.092*
H70.63560.20690.39080.065*
H830.62340.33780.13440.109*
H911.13970.13670.28140.098*
H1031.01990.02640.41630.105*
H810.45260.33420.17210.109*
H820.62160.44820.18240.109*
H921.17920.05840.22830.099*
H931.08150.22360.23100.099*
H1020.89410.12480.41960.105*
H1010.80050.04170.41500.105*
H1110.31330.45460.33590.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0921 (5)0.1292 (5)0.0797 (3)0.0341 (5)0.0358 (3)0.0096 (3)
O110.089 (10)0.070 (6)0.069 (7)0.026 (6)0.038 (5)0.032 (5)
O20.082 (2)0.077 (2)0.0454 (15)0.019 (2)0.0049 (17)0.0001 (15)
O30.051 (2)0.0523 (18)0.0774 (19)0.011 (2)0.011 (2)0.0070 (15)
O40.082 (3)0.083 (2)0.0683 (19)0.021 (2)0.002 (2)0.0085 (17)
O120.093 (10)0.100 (7)0.058 (5)0.031 (8)0.004 (4)0.011 (6)
N10.070 (3)0.053 (2)0.0501 (19)0.007 (2)0.015 (2)0.0114 (16)
C10.076 (4)0.074 (3)0.063 (3)0.014 (3)0.012 (2)0.018 (2)
C20.059 (3)0.048 (2)0.053 (2)0.001 (2)0.009 (2)0.005 (2)
C30.048 (3)0.052 (2)0.046 (2)0.004 (2)0.002 (2)0.0052 (19)
C40.045 (2)0.050 (2)0.048 (2)0.006 (2)0.009 (2)0.005 (2)
C50.047 (3)0.047 (2)0.050 (2)0.005 (2)0.002 (2)0.004 (2)
C60.057 (3)0.052 (2)0.060 (2)0.006 (3)0.006 (2)0.001 (2)
C70.056 (3)0.061 (3)0.045 (2)0.006 (2)0.002 (2)0.005 (2)
C80.115 (5)0.106 (4)0.051 (2)0.009 (5)0.012 (3)0.000 (2)
C90.071 (4)0.091 (4)0.085 (3)0.018 (4)0.013 (3)0.014 (3)
C100.106 (5)0.089 (3)0.068 (2)0.001 (4)0.035 (3)0.018 (2)
C110.060 (3)0.058 (2)0.049 (2)0.007 (2)0.013 (2)0.005 (2)
C120.079 (4)0.075 (3)0.051 (2)0.017 (3)0.016 (2)0.008 (2)
C130.085 (4)0.070 (3)0.047 (2)0.009 (3)0.016 (2)0.002 (2)
C140.076 (4)0.065 (3)0.056 (2)0.003 (3)0.014 (2)0.001 (2)
C150.084 (4)0.088 (3)0.058 (2)0.025 (3)0.016 (3)0.018 (2)
C160.079 (4)0.094 (4)0.055 (2)0.025 (3)0.026 (2)0.015 (2)
Geometric parameters (Å, º) top
Br1—C141.889 (5)C12—C131.375 (7)
O11—O120.693 (18)C13—C141.365 (6)
O11—C11.251 (10)C14—C151.374 (6)
O2—C41.384 (4)C15—C161.375 (8)
O2—C81.392 (6)N1—H1110.841
O3—C51.381 (5)C3—H30.930
O3—C91.419 (7)C7—H70.930
O4—C61.384 (6)C8—H830.960
O4—C101.407 (5)C8—H810.960
O12—C11.250 (14)C8—H820.960
N1—C11.348 (5)C9—H910.960
N1—C21.415 (6)C9—H920.960
C1—C111.483 (7)C9—H930.960
C2—C31.395 (5)C10—H1030.960
C2—C71.378 (6)C10—H1020.960
C3—C41.357 (6)C10—H1010.960
C4—C51.379 (6)C12—H120.930
C5—C61.396 (5)C13—H130.930
C6—C71.365 (6)C15—H150.930
C11—C121.380 (5)C16—H160.930
C11—C161.362 (6)
Br1···C133.578 (4)H12···H132.977
O11···C103.438 (16)H12···H73.299
O11···C133.181 (11)H12···H1022.923
O2···N13.232 (4)H12···H1023.245
O2···C163.470 (6)H12···H1013.427
O3···C163.464 (5)H16···O22.699
O12···C123.368 (13)H16···O32.580
O12···C133.161 (12)H16···C53.529
N1···O23.232 (4)H16···C83.580
C3···C93.524 (7)H16···C92.839
C6···C83.530 (7)H16···H833.333
C7···C83.560 (7)H16···H922.672
C8···C63.530 (7)H16···H932.770
C8···C73.560 (7)H15···O43.316
C9···C33.524 (7)H15···C83.267
C9···C163.565 (6)H15···C93.355
C10···O113.438 (16)H15···C103.237
C12···O123.368 (13)H15···H833.254
C13···Br13.578 (4)H15···H1033.286
C13···O113.181 (11)H15···H812.535
C13···O123.161 (12)H15···H922.881
C16···O23.470 (6)H15···H932.993
C16···O33.464 (5)H15···H1012.692
C16···C93.565 (6)H7···C143.565
Br1···H833.306H7···H123.299
Br1···H1033.268H7···H823.442
Br1···H1013.321H83···Br13.306
O11···H132.369H83···O113.548
O11···H123.283H83···H163.333
O11···H833.548H83···H153.254
O11···H1033.005H83···H1033.089
O11···H823.536H83···H1013.440
O11···H1023.162H83···H1113.376
O2···H33.330H91···N13.239
O2···H162.699H91···C23.244
O2···H923.562H91···C33.103
O2···H1112.487H91···C83.395
O3···H32.913H91···H32.983
O3···H162.580H91···H822.520
O3···H932.813H91···H1113.293
O3···H1112.858H103···Br13.268
O4···H153.316H103···O113.005
O4···H813.132H103···C153.430
O4···H823.550H103···H132.991
O4···H933.408H103···H153.286
O12···H132.486H103···H833.089
O12···H122.911H81···O43.132
N1···H913.239H81···C53.385
C1···H133.529H81···C62.999
C1···H1023.426H81···C73.356
C2···H913.244H81···C153.452
C2···H823.162H81···H152.535
C2···H923.434H81···H923.382
C3···H913.103H81···H933.200
C3···H823.430H81···H1013.092
C3···H923.477H82···O113.536
C3···H922.991H82···O43.550
C3···H933.426H82···C23.162
C4···H33.118H82···C33.430
C4···H823.588H82···C43.588
C4···H923.061H82···C53.504
C4···H1113.261H82···C63.234
C5···H32.887H82···C73.079
C5···H163.529H82···C93.116
C5···H813.385H82···H73.442
C5···H823.504H82···H912.520
C5···H923.574H82···H922.890
C5···H1113.382H92···O23.562
C6···H33.489H92···C23.434
C6···H812.999H92···C33.477
C6···H823.234H92···C32.991
C7···H813.356H92···C43.061
C7···H823.079H92···C53.574
C8···H163.580H92···C153.315
C8···H153.267H92···C163.215
C8···H913.395H92···H33.336
C8···H1113.408H92···H33.176
C9···H33.254H92···H162.672
C9···H162.839H92···H152.881
C9···H153.355H92···H813.382
C9···H823.116H92···H822.890
C10···H153.237H92···H933.558
C11···H1023.053H93···O32.813
C12···H1022.836H93···O43.408
C13···H123.438H93···C33.426
C13···H1023.348H93···C153.554
C14···H73.565H93···C163.458
C14···H1013.385H93···H32.916
C15···H1033.430H93···H162.770
C15···H813.452H93···H152.993
C15···H923.315H93···H813.200
C15···H933.554H93···H923.558
C15···H1013.097H102···O113.162
C16···H923.215H102···C13.426
C16···H933.458H102···C113.053
H3···O23.330H102···C122.836
H3···O32.913H102···C133.348
H3···C43.118H102···H122.923
H3···C52.887H102···H123.245
H3···C63.489H101···Br13.321
H3···C93.254H101···C143.385
H3···H912.983H101···C153.097
H3···H923.336H101···H123.427
H3···H923.176H101···H152.692
H3···H932.916H101···H833.440
H13···O112.369H101···H813.092
H13···O122.486H111···O22.487
H13···C13.529H111···O32.858
H13···H122.977H111···C43.261
H13···H1032.991H111···C53.382
H12···O113.283H111···C83.408
H12···O122.911H111···H833.376
H12···C133.438H111···H913.293
O12—O11—C173.9 (12)C11—C16—C15121.6 (4)
C4—O2—C8117.9 (3)C1—N1—H111117.3
C5—O3—C9111.1 (3)C2—N1—H111115.4
C6—O4—C10117.8 (3)C2—C3—H3119.7
O11—O12—C174.0 (15)C4—C3—H3120.7
C1—N1—C2127.0 (3)C2—C7—H7120.7
O11—C1—N1118.9 (7)C6—C7—H7120.8
O11—C1—C11119.2 (8)O2—C8—H83108.6
O12—C1—N1121.9 (8)O2—C8—H81109.7
O12—C1—C11118.2 (8)O2—C8—H82110.0
N1—C1—C11118.1 (4)H83—C8—H81109.5
N1—C2—C3117.6 (3)H83—C8—H82109.5
N1—C2—C7122.0 (3)H81—C8—H82109.5
C3—C2—C7120.4 (4)O3—C9—H91109.9
C2—C3—C4119.6 (3)O3—C9—H92109.4
O2—C4—C3124.1 (3)O3—C9—H93109.1
O2—C4—C5114.2 (3)H91—C9—H92109.5
C3—C4—C5121.6 (3)H91—C9—H93109.5
O3—C5—C4120.6 (3)H92—C9—H93109.5
O3—C5—C6121.8 (3)O4—C10—H103109.9
C4—C5—C6117.5 (4)O4—C10—H102109.4
O4—C6—C5114.0 (4)O4—C10—H101109.0
O4—C6—C7123.8 (3)H103—C10—H102109.5
C5—C6—C7122.3 (4)H103—C10—H101109.5
C2—C7—C6118.5 (3)H102—C10—H101109.5
C1—C11—C12117.6 (4)C11—C12—H12119.0
C1—C11—C16123.9 (3)C13—C12—H12120.4
C12—C11—C16118.4 (4)C12—C13—H13120.7
C11—C12—C13120.5 (4)C14—C13—H13119.1
C12—C13—C14120.3 (3)C14—C15—H15119.1
Br1—C14—C13119.6 (3)C16—C15—H15121.4
Br1—C14—C15120.7 (3)C11—C16—H16119.1
C13—C14—C15119.7 (4)C15—C16—H16119.3
C14—C15—C16119.5 (4)
O12—O11—C1—N1104.9 (17)C7—C2—C3—C40.2 (5)
O12—O11—C1—C1197.4 (19)C2—C3—C4—O2177.6 (4)
C8—O2—C4—C319.1 (6)C2—C3—C4—C51.0 (6)
C8—O2—C4—C5164.1 (4)O2—C4—C5—O32.0 (6)
C9—O3—C5—C4100.5 (4)O2—C4—C5—C6178.2 (3)
C9—O3—C5—C683.4 (5)C3—C4—C5—O3174.9 (4)
C10—O4—C6—C5179.5 (4)C3—C4—C5—C61.3 (6)
C10—O4—C6—C71.7 (6)O3—C5—C6—O43.1 (6)
O11—O12—C1—N194.5 (19)O3—C5—C6—C7175.7 (4)
O11—O12—C1—C11100.7 (17)C4—C5—C6—O4179.3 (4)
C1—N1—C2—C3154.2 (4)C4—C5—C6—C70.5 (6)
C1—N1—C2—C724.3 (7)O4—C6—C7—C2178.0 (4)
C2—N1—C1—O1112.2 (10)C5—C6—C7—C20.7 (7)
C2—N1—C1—O1225.1 (9)C1—C11—C12—C13177.7 (4)
C2—N1—C1—C11170.1 (4)C1—C11—C16—C15177.1 (4)
O11—C1—C11—C1226.8 (9)C12—C11—C16—C150.6 (7)
O11—C1—C11—C16149.7 (8)C16—C11—C12—C131.0 (7)
O12—C1—C11—C1210.0 (9)C11—C12—C13—C141.4 (7)
O12—C1—C11—C16173.5 (8)C12—C13—C14—Br1179.7 (3)
N1—C1—C11—C12175.4 (4)C12—C13—C14—C151.3 (7)
N1—C1—C11—C168.1 (7)Br1—C14—C15—C16179.3 (4)
N1—C2—C3—C4178.3 (3)C13—C14—C15—C160.9 (7)
N1—C2—C7—C6177.4 (4)C14—C15—C16—C110.6 (8)
C3—C2—C7—C61.0 (6)
 

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