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The title compound, C30H31ClN2O4, crystallizes as discrete mol­ecules. Non-classical C—H...O hydrogen bonds link the mol­ecules in the crystal structure into a sheet parallel to (\overline 101).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005854/hg6138sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005854/hg61383sup2.hkl
Contains datablock 3

CCDC reference: 270429

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.102
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H241 .. O4 .. 2.62 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for N2 .. O4 .. 96.00 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku Corporation,1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure 3.6.0 (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick,1997); program(s) used to refine structure: CRYSTALS (Watkin et al.,1996); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: CrystalStructure 3.6.0.

(3) top
Crystal data top
C30H31ClN2O4F(000) = 1096.00
Mr = 519.04Dx = 1.278 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ynCell parameters from 13437 reflections
a = 14.7792 (3) Åθ = 2.2–27.5°
b = 16.7390 (2) ŵ = 0.18 mm1
c = 14.6920 (3) ÅT = 293 K
β = 132.0900 (5)°Block, colorless
V = 2697.24 (8) Å30.33 × 0.30 × 0.17 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5221 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.028
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1919
Tmin = 0.925, Tmax = 0.970k = 2121
25182 measured reflectionsl = 1919
6039 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0009Fo2 + σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.038(Δ/σ)max < 0.001
wR(F2) = 0.102Δρmax = 0.29 e Å3
S = 1.01Δρmin = 0.26 e Å3
5221 reflectionsExtinction correction: Larson (1970), equation 22
335 parametersExtinction coefficient: 231 (36)
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*/Ueq
Cl(1)0.02323 (4)0.48001 (3)0.25630 (4)0.0653 (1)
O(1)0.2652 (1)0.82569 (6)0.3288 (1)0.0467 (3)
O(2)0.2908 (1)0.63642 (6)0.4647 (1)0.0514 (3)
O(3)0.0352 (1)0.78008 (7)0.4021 (1)0.0532 (3)
O(4)0.55329 (9)0.58872 (7)0.4960 (1)0.0520 (3)
N(1)0.1832 (1)0.75266 (7)0.3907 (1)0.0402 (3)
N(2)0.3618 (1)0.65965 (7)0.2993 (1)0.0424 (4)
C(1)0.2453 (1)0.69213 (8)0.1902 (1)0.0363 (4)
C(2)0.1638 (1)0.70366 (9)0.2190 (1)0.0364 (4)
C(3)0.0346 (1)0.7323 (1)0.1074 (1)0.0514 (5)
C(4)0.2147 (1)0.76554 (9)0.3185 (1)0.0363 (4)
C(5)0.2186 (1)0.68110 (9)0.4538 (1)0.0415 (4)
C(6)0.1593 (1)0.66331 (9)0.5009 (1)0.0479 (5)
C(7)0.1882 (2)0.5940 (1)0.5688 (2)0.0644 (6)
C(8)0.1202 (3)0.5742 (1)0.5994 (2)0.0824 (8)
C(9)0.0243 (3)0.6219 (2)0.5611 (2)0.0865 (9)
C(10)0.0049 (2)0.6907 (1)0.4955 (2)0.0711 (7)
C(11)0.0644 (2)0.7120 (1)0.4670 (2)0.0520 (5)
C(12)0.1327 (1)0.81669 (9)0.4164 (1)0.0425 (4)
C(13)0.2304 (1)0.8492 (1)0.5455 (2)0.0498 (5)
C(14)0.1808 (2)0.9153 (1)0.5743 (2)0.0687 (7)
C(15)0.1189 (2)0.9809 (1)0.4792 (2)0.0711 (7)
C(16)0.0199 (2)0.9474 (1)0.3513 (2)0.0670 (6)
C(17)0.0716 (2)0.8835 (1)0.3225 (2)0.0569 (5)
C(18)0.4610 (1)0.65158 (8)0.3103 (1)0.0380 (4)
C(19)0.4656 (1)0.6792 (1)0.2247 (1)0.0476 (5)
C(20)0.5712 (2)0.6703 (1)0.2440 (2)0.0601 (6)
C(21)0.6717 (2)0.6327 (1)0.3471 (2)0.0636 (6)
C(22)0.6691 (1)0.6042 (1)0.4342 (2)0.0552 (5)
C(23)0.5661 (1)0.61303 (9)0.4167 (1)0.0422 (4)
C(24)0.6531 (2)0.5472 (1)0.6045 (1)0.0607 (5)
C(25)0.1825 (1)0.63793 (8)0.0788 (1)0.0369 (4)
C(26)0.1666 (1)0.55728 (9)0.0859 (1)0.0403 (4)
C(27)0.1034 (1)0.50865 (9)0.0162 (1)0.0428 (4)
C(28)0.0563 (1)0.54092 (9)0.1265 (1)0.0452 (4)
C(29)0.0717 (2)0.6203 (1)0.1361 (1)0.0581 (5)
C(30)0.1352 (2)0.6684 (1)0.0331 (1)0.0516 (5)
H(1)0.25970.74430.17170.040*
H(2)0.15730.65250.24680.042*
H(201)0.35630.64440.35510.051*
H(7)0.25580.55980.59480.075*
H(8)0.14040.52620.64810.102*
H(9)0.02440.60630.58130.118*
H(10)0.07330.72410.46930.094*
H(19)0.39400.70520.14970.059*
H(20)0.57360.69120.18330.081*
H(21)0.74500.62590.35920.081*
H(22)0.74110.57770.50820.063*
H(26)0.20070.53440.16480.050*
H(27)0.09230.45180.01000.054*
H(30)0.14690.72510.03960.058*
H(131)0.29640.87090.55370.063*
H(132)0.26100.80600.60370.063*
H(140)0.12230.89210.57660.091*
H(142)0.24800.93820.65370.091*
H(151)0.17921.00800.48250.098*
H(152)0.08281.01870.49690.098*
H(161)0.01450.99030.29200.086*
H(162)0.04340.92380.34610.086*
H(171)0.00560.86130.24200.071*
H(172)0.13110.90800.32240.071*
H(229)0.03790.64280.21510.063*
H(241)0.62360.51590.63480.065*
H(242)0.69080.51280.58600.064*
H(243)0.71190.58510.66590.065*
H(301)0.03780.78740.09170.057*
H(302)0.01770.72660.12410.058*
H(303)0.00370.70080.03700.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl(1)0.0691 (3)0.0595 (3)0.0491 (3)0.0123 (2)0.0321 (2)0.0176 (2)
O(1)0.0498 (6)0.0419 (6)0.0515 (7)0.0063 (5)0.0352 (6)0.0041 (5)
O(2)0.0550 (7)0.0449 (6)0.0500 (7)0.0119 (6)0.0335 (6)0.0078 (5)
O(3)0.0481 (7)0.0498 (7)0.0697 (8)0.0052 (5)0.0427 (6)0.0056 (6)
O(4)0.0450 (6)0.0584 (7)0.0447 (6)0.0144 (5)0.0268 (6)0.0125 (5)
N(1)0.0499 (7)0.0355 (7)0.0433 (7)0.0052 (6)0.0345 (7)0.0027 (6)
N(2)0.0348 (7)0.0585 (8)0.0339 (7)0.0079 (6)0.0230 (6)0.0061 (6)
C(1)0.0354 (8)0.0361 (8)0.0319 (7)0.0036 (6)0.0204 (7)0.0029 (6)
C(2)0.0339 (7)0.0367 (8)0.0350 (8)0.0011 (6)0.0215 (7)0.0009 (6)
C(3)0.0365 (9)0.060 (1)0.0453 (9)0.0035 (8)0.0222 (8)0.0040 (8)
C(4)0.0317 (7)0.0376 (8)0.0351 (8)0.0048 (7)0.0205 (7)0.0031 (6)
C(5)0.0447 (9)0.0376 (8)0.0359 (8)0.0032 (7)0.0244 (7)0.0030 (7)
C(6)0.055 (1)0.0458 (9)0.0415 (9)0.0124 (8)0.0317 (8)0.0074 (7)
C(7)0.082 (1)0.056 (1)0.050 (1)0.013 (1)0.042 (1)0.0010 (9)
C(8)0.109 (2)0.076 (1)0.071 (1)0.026 (1)0.064 (1)0.003 (1)
C(9)0.109 (2)0.095 (2)0.091 (2)0.041 (2)0.081 (2)0.020 (1)
C(10)0.075 (1)0.075 (1)0.086 (1)0.027 (1)0.063 (1)0.021 (1)
C(11)0.057 (1)0.053 (1)0.055 (1)0.0187 (9)0.0407 (9)0.0149 (8)
C(12)0.0447 (9)0.0406 (8)0.0530 (9)0.0003 (7)0.0371 (8)0.0033 (7)
C(13)0.056 (1)0.0471 (9)0.056 (1)0.0096 (8)0.0416 (9)0.0093 (8)
C(14)0.078 (1)0.069 (1)0.080 (1)0.018 (1)0.062 (1)0.029 (1)
C(15)0.082 (1)0.047 (1)0.115 (2)0.003 (1)0.079 (1)0.016 (1)
C(16)0.071 (1)0.051 (1)0.094 (2)0.013 (1)0.061 (1)0.003 (1)
C(17)0.065 (1)0.047 (1)0.066 (1)0.0145 (9)0.046 (1)0.0073 (9)
C(18)0.0364 (8)0.0350 (8)0.0406 (8)0.0021 (6)0.0250 (7)0.0066 (6)
C(19)0.049 (1)0.0486 (9)0.050 (1)0.0007 (8)0.0357 (9)0.0010 (8)
C(20)0.067 (1)0.060 (1)0.076 (1)0.006 (1)0.057 (1)0.003 (1)
C(21)0.051 (1)0.064 (1)0.088 (1)0.0005 (9)0.051 (1)0.005 (1)
C(22)0.0405 (9)0.051 (1)0.065 (1)0.0048 (8)0.0317 (9)0.0005 (9)
C(23)0.0389 (8)0.0368 (8)0.0460 (9)0.0007 (7)0.0265 (8)0.0038 (7)
C(24)0.057 (1)0.054 (1)0.048 (1)0.0161 (9)0.0254 (9)0.0096 (8)
C(25)0.0350 (8)0.0379 (8)0.0351 (8)0.0061 (6)0.0224 (7)0.0042 (6)
C(26)0.0447 (9)0.0414 (8)0.0398 (9)0.0064 (7)0.0303 (8)0.0058 (7)
C(27)0.0474 (9)0.0362 (8)0.0518 (9)0.0009 (7)0.0361 (8)0.0004 (7)
C(28)0.0429 (9)0.0445 (9)0.0407 (9)0.0001 (7)0.0250 (8)0.0050 (7)
C(29)0.073 (1)0.048 (1)0.0347 (9)0.0010 (9)0.0289 (9)0.0041 (7)
C(30)0.067 (1)0.0377 (9)0.0400 (9)0.0009 (8)0.0319 (8)0.0039 (7)
Geometric parameters (Å, º) top
Cl(1)—C(28)1.748 (2)C(25)—C(30)1.383 (3)
O(1)—C(4)1.201 (2)C(26)—C(27)1.381 (2)
O(2)—C(5)1.223 (3)C(27)—C(28)1.375 (3)
O(3)—C(11)1.357 (2)C(28)—C(29)1.372 (2)
O(3)—C(12)1.446 (3)C(29)—C(30)1.383 (2)
O(4)—C(23)1.361 (3)N(2)—H(201)0.9124
O(4)—C(24)1.431 (2)C(1)—H(1)0.9800
N(1)—C(4)1.432 (3)C(2)—H(2)0.9800
N(1)—C(5)1.385 (2)C(3)—H(301)0.9600
N(1)—C(12)1.493 (3)C(3)—H(302)0.9600
N(2)—C(1)1.460 (1)C(3)—H(303)0.9600
N(2)—C(18)1.370 (3)C(7)—H(7)0.9800
C(1)—C(2)1.533 (3)C(8)—H(8)0.9800
C(1)—C(25)1.525 (2)C(9)—H(9)0.9800
C(2)—C(3)1.538 (2)C(10)—H(10)0.9800
C(2)—C(4)1.517 (2)C(13)—H(131)0.9700
C(5)—C(6)1.465 (4)C(13)—H(132)0.9700
C(6)—C(7)1.398 (3)C(14)—H(140)0.9700
C(6)—C(11)1.394 (3)C(14)—H(142)0.9700
C(7)—C(8)1.387 (5)C(15)—H(151)0.9700
C(8)—C(9)1.376 (5)C(15)—H(152)0.9700
C(9)—C(10)1.373 (4)C(16)—H(161)0.9700
C(10)—C(11)1.387 (5)C(16)—H(162)0.9700
C(12)—C(13)1.519 (2)C(17)—H(171)0.9700
C(12)—C(17)1.517 (2)C(17)—H(172)0.9700
C(13)—C(14)1.534 (4)C(19)—H(19)0.9800
C(14)—C(15)1.511 (3)C(20)—H(20)0.9800
C(15)—C(16)1.517 (3)C(21)—H(21)0.9800
C(16)—C(17)1.530 (4)C(22)—H(22)0.9800
C(18)—C(19)1.384 (3)C(24)—H(241)0.9600
C(18)—C(23)1.420 (2)C(24)—H(242)0.9600
C(19)—C(20)1.394 (4)C(24)—H(243)0.9600
C(20)—C(21)1.371 (2)C(26)—H(26)0.9800
C(21)—C(22)1.390 (4)C(27)—H(27)0.9800
C(22)—C(23)1.372 (4)C(29)—H(229)0.9800
C(25)—C(26)1.386 (2)C(30)—H(30)0.9800
Cl(1)—C(28)—C(27)119.7 (1)H(201)—N(2)—C(18)126.8402
Cl(1)—C(28)—C(29)119.3 (1)H(1)—C(1)—C(2)108.7459
O(1)—C(4)—N(1)121.1 (2)C(1)—C(2)—H(2)108.5756
O(1)—C(4)—C(2)124.0 (2)H(1)—C(1)—C(25)108.7737
O(2)—C(5)—N(1)121.4 (2)H(2)—C(2)—C(3)108.6035
O(2)—C(5)—C(6)124.1 (2)C(2)—C(3)—H(301)109.3182
C(12)—O(3)—C(11)115.9 (1)C(2)—C(3)—H(302)109.4677
O(3)—C(11)—C(6)120.8 (2)C(2)—C(3)—H(303)109.3612
O(3)—C(11)—C(10)118.4 (2)H(2)—C(2)—C(4)108.5752
O(3)—C(12)—N(1)106.1 (1)H(302)—C(3)—H(301)109.5593
O(3)—C(12)—C(13)110.7 (2)H(303)—C(3)—H(301)109.4654
O(3)—C(12)—C(17)104.7 (1)H(303)—C(3)—H(302)109.6548
O(4)—C(23)—C(18)113.7 (2)C(6)—C(7)—H(7)120.4219
O(4)—C(23)—C(22)125.5 (1)H(7)—C(7)—C(8)120.3472
C(24)—O(4)—C(23)117.9 (2)C(7)—C(8)—H(8)119.9805
N(1)—C(4)—C(2)114.4 (1)H(8)—C(8)—C(9)119.9865
C(5)—N(1)—C(4)117.5 (2)C(8)—C(9)—H(9)119.1249
C(12)—N(1)—C(4)123.1 (1)C(9)—C(10)—H(10)120.6720
C(12)—N(1)—C(5)118.6 (2)H(9)—C(9)—C(10)119.1064
N(1)—C(5)—C(6)114.5 (2)H(10)—C(10)—C(11)120.7175
N(1)—C(12)—C(13)110.8 (1)C(12)—C(13)—H(131)108.8733
N(1)—C(12)—C(17)113.1 (2)C(12)—C(13)—H(132)108.8805
N(2)—C(1)—C(2)108.1 (1)C(12)—C(17)—H(171)108.9680
C(18)—N(2)—C(1)123.2 (2)C(12)—C(17)—H(172)109.0075
N(2)—C(1)—C(25)112.2 (1)H(131)—C(13)—C(14)108.8698
N(2)—C(18)—C(19)124.1 (1)H(132)—C(13)—C(14)108.8614
N(2)—C(18)—C(23)117.9 (2)C(13)—C(14)—H(140)108.8476
C(1)—C(2)—C(3)112.9 (2)C(13)—C(14)—H(142)108.8415
C(1)—C(2)—C(4)112.2 (1)H(132)—C(13)—H(131)109.4539
C(25)—C(1)—C(2)110.2 (1)H(140)—C(14)—C(15)108.8482
C(1)—C(25)—C(26)120.7 (2)H(142)—C(14)—C(15)108.8333
C(1)—C(25)—C(30)121.0 (1)C(14)—C(15)—H(151)109.0728
C(4)—C(2)—C(3)105.9 (1)C(14)—C(15)—H(152)109.0735
C(5)—C(6)—C(7)120.9 (2)H(142)—C(14)—H(140)109.4606
C(5)—C(6)—C(11)119.3 (2)C(15)—C(16)—H(162)109.1495
C(11)—C(6)—C(7)119.5 (3)H(151)—C(15)—C(16)109.0966
C(6)—C(7)—C(8)119.2 (2)C(15)—C(16)—H(161)109.1145
C(6)—C(11)—C(10)120.8 (2)H(152)—C(15)—C(16)109.0376
C(7)—C(8)—C(9)120.0 (3)H(152)—C(15)—H(151)109.4644
C(8)—C(9)—C(10)121.8 (4)C(16)—C(17)—H(171)108.9068
C(9)—C(10)—C(11)118.6 (3)C(16)—C(17)—H(172)109.0096
C(17)—C(12)—C(13)111.1 (1)H(162)—C(16)—C(17)109.1602
C(12)—C(13)—C(14)111.9 (1)H(161)—C(16)—C(17)109.1376
C(12)—C(17)—C(16)111.5 (2)H(162)—C(16)—H(161)109.4594
C(13)—C(14)—C(15)112.0 (3)H(172)—C(17)—H(171)109.4604
C(14)—C(15)—C(16)111.1 (2)C(18)—C(19)—H(19)119.6977
C(15)—C(16)—C(17)110.8 (2)H(19)—C(19)—C(20)119.6593
C(23)—C(18)—C(19)118.0 (2)C(19)—C(20)—H(20)119.6626
C(18)—C(19)—C(20)120.6 (2)H(20)—C(20)—C(21)119.7006
C(18)—C(23)—C(22)120.8 (2)C(20)—C(21)—H(21)120.1031
C(19)—C(20)—C(21)120.6 (3)C(21)—C(22)—H(22)119.8354
C(20)—C(21)—C(22)119.8 (3)H(21)—C(21)—C(22)120.1353
C(21)—C(22)—C(23)120.2 (2)H(22)—C(22)—C(23)119.9811
C(25)—C(26)—C(27)121.2 (2)H(242)—C(24)—H(241)109.4741
C(30)—C(25)—C(26)118.2 (1)H(243)—C(24)—H(241)109.4639
C(25)—C(30)—C(29)121.1 (2)H(243)—C(24)—H(242)109.3262
C(26)—C(27)—C(28)119.2 (2)C(25)—C(26)—H(26)119.4336
C(27)—C(28)—C(29)121.0 (2)C(25)—C(30)—H(30)119.4373
C(28)—C(29)—C(30)119.3 (2)C(26)—C(27)—H(27)120.3668
O(4)—C(24)—H(241)109.4369H(26)—C(26)—C(27)119.3886
O(4)—C(24)—H(242)109.6548H(27)—C(27)—C(28)120.4253
O(4)—C(24)—H(243)109.4712C(28)—C(29)—H(229)120.4107
N(2)—C(1)—H(1)108.7047H(229)—C(29)—C(30)120.3181
H(201)—N(2)—C(1)109.9252C(29)—C(30)—H(30)119.4185
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H201···O20.912.373.251 (3)161
N2—H201···O40.912.362.609 (1)96
C24—H243···O1i0.962.463.287 (2)144
C24—H241···O4ii0.962.623.259 (2)124
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x+1, y+1, z+1.
 

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