The threshold expression of em F /em 2 ( em F /em 2) is used limited to calculating em R /em -elements(gt) em etc /em . and isn’t relevant to the decision of reflections for refinement. em R /em -elements predicated on em F /em 2 are statistically about doubly large as those predicated on em F /em , and em R /em – points predicated on ALL data will be even larger. Open in another window Fractional atomic coordinates and isotropic or similar isotropic displacement parameters (?2) em x /em em con /em em z /em em U /em iso*/ em U /em eqC20.2640 (2)?0.3204 (3)0.32882 (13)0.0425 (5)C30.21718 (19)?0.1773 (3)0.26133 (17)0.0490 (5)H3A0.1398?0.12960.27730.059*H3B0.2121?0.24380.20580.059*C40.3027 (2)?0.0043 (4)0.25750 (16)0.0590 (6)H4A0.26260.12270.26700.071*H4B0.34090.00030.20170.071*C50.3932 (2)?0.0428 (3)0.32948 (15)0.0466 (5)H50.4708?0.05780.30330.056*C60.40010 (17)0.1156 (3)0.40092 (13)0.0400 (4)H60.43400.23930.37710.048*C70.47970 (18)0.0382 (3)0.47386 (13)0.0421 (5)H70.55580.00750.44780.051*C80.4309 (2)?0.1608 (3)0.50890 (16)0.0514 (6)H8A0.4814?0.21000.55450.062*H8B0.3537?0.13780.53320.062*C90.4226 (2)?0.3184 (3)0.43821 (15)0.0557 (6)H9A0.5006?0.35690.41970.067*H9B0.3832?0.43750.46000.067*C100.50152 (16)0.1935 (3)0.54318 (14)0.0407 (5)C110.42606 (19)0.2235 (4)0.61193 (16)0.0507 (5)H110.35820.14640.61590.061*C120.4494 (2)0.3654 (4)0.67466 (16)0.0580 (6)H120.39760.38330.72030.070*C130.5498 (2)0.4808 (4)0.66972 (17)0.0599 (7)H130.56620.57540.71220.072*C140.6248 (2)0.4553 (4)0.60216 (17)0.0623 (7)H140.69190.53430.59820.075*C150.60156 (19)0.3120 (4)0.53928 (16)0.0501 (5)H150.65380.29510.49380.060*N10.35736 (17)?0.2359 (3)0.36550 (12)0.0473 (4)O10.22237 (14)?0.4869 (2)0.34724 (11)0.0545 (5)O20.28771 (12)0.1598 (2)0.43433 (11)0.0496 (4)H20.26470.26730.41460.074* Open in another window Atomic displacement parameters (?2) em U /em 11 em U /em 22 em U /em 33 em U /em 12 em U /em 13 em U /em 23C20.0503 (12)0.0381 (10)0.0391 (11)0.0064 (9)0.0004 (9)?0.0066 (9)C30.0507 (13)0.0483 (11)0.0480 (12)0.0040 (9)?0.0032 (10)0.0014 (10)C40.0858 (18)0.0477 (12)0.0436 (12)?0.0088 (11)?0.0148 (13)0.0042 (10)C50.0585 (13)0.0404 (10)0.0408 (10)?0.0013 (9)?0.0015 (10)0.0023 (9)C60.0488 (11)0.0331 (10)0.0382 (10)?0.0015 (8)0.0012 (9)0.0038 (8)C70.0395 (10)0.0449 (12)0.0419 (11)0.0035 (8)?0.0023 (9)?0.0003 (9)C80.0681 (15)0.0384 (11)0.0478 (11)0.0032 (10)?0.0163 (11)0.0054 (9)C90.0736 (15)0.0366 (11)0.0570 (14)0.0078 (9)?0.0211 (12)0.0039 (10)C100.0405 (10)0.0417 (11)0.0397 (10)0.0017 (8)?0.0059 (9)0.0024 (8)C110.0523 (11)0.0496 (12)0.0501 (12)0.0022 (9)0.0080 (11)?0.0004 (10)C120.0783 (16)0.0509 (12)0.0447 (12)0.0132 (12)0.0045 (12)?0.0045 (11)C130.0818 (17)0.0480 (12)0.0500 (13)0.0058 (11)?0.0209 (13)?0.0055 (11)C140.0621 (14)0.0556 (14)0.0693 (16)?0.0098 (11)?0.0195 (14)0.0004 (12)C150.0453 (11)0.0587 (13)0.0464 (12)?0.0024 (10)?0.0031 (10)0.0035 (10)N10.0593 (11)0.0359 (9)0.0465 (9)0.0005 (8)?0.0100 (8)0.0014 (8)O10.0640 (11)0.0413 (8)0.0582 (11)?0.0047 (6)?0.0065 (8)0.0027 (7)O20.0456 (8)0.0486 (8)0.0546 (9)0.0083 (6)0.0023 (7)0.0085 (7) Open in another window Geometric parameters (?, ) C2O11.237?(2)C8C91.518?(3)C2N11.332?(3)C8H8A0.9700C2C31.511?(3)C8H8B0.9700C3C41.508?(3)C9N11.458?(3)C3H3A0.9700C9H9A0.9700C3H3B0.9700C9H9B0.9700C4C51.542?(3)C10C111.385?(3)C4H4A0.9700C10C151.388?(3)C4H4B0.9700C11C121.380?(3)C5N11.457?(3)C11H110.9300C5C61.530?(3)C12C131.380?(4)C5H50.9800C12H120.9300C6O21.414?(2)C13C141.364?(4)C6C71.540?(3)C13H130.9300C6H60.9800C14C151.388?(3)C7C101.510?(3)C14H140.9300C7C81.533?(3)C15H150.9300C7H70.9800O2H20.8200O1C2N1125.78?(19)C9C8H8A109.4O1C2C3125.9?(2)C7C8H8A109.4N1C2C3108.33?(17)C9C8H8B109.4C2C3C4106.09?(18)C7C8H8B109.4C2C3H3A110.5H8AC8H8B108.0C4C3H3A110.5N1C9C8109.40?(16)C2C3H3B110.5N1C9H9A109.8C4C3H3B110.5C8C9H9A109.8H3AC3H3B108.7N1C9H9B109.8C3C4C5106.18?(18)C8C9H9B109.8C3C4H4A110.5H9AC9H9B108.2C5C4H4A110.5C11C10C15117.7?(2)C3C4H4B110.5C11C10C7122.92?(19)C5C4H4B110.5C15C10C7119.4?(2)H4AC4H4B108.7C10C11C12121.4?(2)N1C5C6109.98?(17)C10C11H11119.3N1C5C4103.63?(18)C12C11H11119.3C6C5C4116.45?(19)C13C12C11120.0?(2)N1C5H5108.8C13C12H12120.0C6C5H5108.8C11C12H12120.0C4C5H5108.8C14C13C12119.7?(2)O2C6C5111.15?(17)C14C13H13120.2O2C6C7109.59?(16)C12C13H13120.2C5C6C7109.49?(16)C13C14C15120.3?(2)O2C6H6108.9C13C14H14119.9C5C6H6108.9C15C14H14119.9C7C6H6108.9C10C15C14121.0?(2)C10C7C6113.12?(15)C10C15H15119.5C10C7C8113.31?(18)C14C15H15119.5C6C7C8109.48?(17)C2N1C5115.52?(17)C10C7H7106.8C2N1C9125.54?(18)C6C7H7106.8C5N1C9118.92?(18)C8C7H7106.8C6O2H2109.5C9C8C7111.1?(2)O1C2C3C4?175.3?(2)C8C7C10C15139.5?(2)N1C2C3C45.1?(2)C15C10C11C12?0.3?(3)C2C3C4C5?4.7?(2)C7C10C11C12179.3?(2)C3C4C5N12.8?(2)C10C11C12C13?0.1?(4)C3C4C5C6?118.0?(2)C11C12C13C140.7?(4)N1C5C6O2?67.5?(2)C12C13C14C15?1.0?(4)C4C5C6O250.0?(2)C11C10C15C140.0?(3)N1C5C6C753.7?(2)C7C10C15C14?179.6?(2)C4C5C6C7171.18?(18)C13C14C15C100.6?(3)O2C6C7C10?63.7?(2)O1C2N1C5176.9?(2)C5C6C7C10174.18?(17)C3C2N1C5?3.5?(2)O2C6C7C863.7?(2)O1C2N1C9?4.6?(3)C5C6C7C8?58.4?(2)C3C2N1C9175.0?(2)C10C7C8C9?174.06?(18)C6C5N1C2125.53?(19)C6C7C8C958.6?(2)C4C5N1C20.4?(2)C7C8C9N1?52.9?(3)C6C5N1C9?53.1?(3)C6C7C10C1185.3?(2)C4C5N1C9?178.2?(2)C8C7C10C11?40.0?(3)C8C9N1C2?126.4?(2)C6C7C10C15?95.1?(2)C8C9N1C552.1?(3) Open in another window Hydrogen-bond geometry (?, ) em D /em H em A Vilazodone /em em D /em HH em A /em em D /em em A /em em D /em H em A /em O2H2O1we0.822.002.807?(2)170 Open in another window Symmetry rules: (i actually) em x /em , em /em +1 y, em z /em . Footnotes Supplementary data and figures because of this paper can be found in the IUCr digital archives (Guide: BG2260).. Gupta (2003 ?); Rosseels (1982 ?); Oslund (2008 ?); Ostby (2000 ?). For synthesis of indolizines, find: Chuprakov & Gevorgyan (2007 ?); Yan & Liu (2007 ?). For the synthesis Vilazodone strategies used, find: ?af? (2009 ?). For buildings linked to the name substance, see: ?vorc (2009 ?). Vilazodone For evaluation of mol-ecular variables, find: Camus (2003 ?); Lokaj (1999 ?); Dark brown & Corbridge (1954 ?); Pedersen (1967 ?). For an over-all evaluation of puckering, find: Cremer & Pople (1975 ?). Experimental Crystal data C14H17NO2 = 231.29 Orthorhombic, = 11.4164 (3) ? = 6.6372 (2) ? = 15.5118 (4) ? = 1175.38 (6) ?3 = 4 Mo = 298 K 0.60 0.56 0.13 mm Data collection Oxford Diffraction Gemini R CCD diffractometer Absorption modification: analytical (Clark & Reid, 1995 ?) 2(= 1.03 1632 reflections 157 variables 1 restraint H-atom variables constrained max = 0.17 e ??3 min = ?0.12 e ??3 Data collection: (Oxford Diffraction, 2006 ?); cell refinement: (Oxford Diffraction, 2006 ?); data decrease: (Sheldrick, 2008 ?); plan(s) utilized to refine framework: (Sheldrick, 2008 ?); molecular images: (Brandenburg, 2001 ?); software program used to get ready materials for publication: (Allen axis (Fig. 2) and help stabilize the crystal framework of the substance. Bond measures and sides in the indolizine band program are in great agreement with beliefs from the books (Camus = 231.29= 11.4164 (3) ? = 3.3C29.4= 6.6372 (2) ? = 0.09 mm?1= 15.5118 (4) ?= 298 K= 1175.38 (6) ?3Block, light= 40.60 0.56 0.13 mm Open up in another screen Data collection Oxford Diffraction Gemini R CCD diffractometer1632 separate reflectionsRadiation supply: fine-focus sealed pipe1128 reflections with 2(= ?1515Absorption correction: analytical (Clark & Reid, 1995)= ?99= ?202126298 measured reflections Open up in another window Refinement Refinement on = 1/[2(= (= 1.03(/)max 0.0011632 reflectionsmax = 0.17 e ??3157 parametersmin = ?0.12 e ??31 restraintExtinction correction: (Sheldrick, 2008), Fc*=kFc[1+0.001xFc23/sin(2)]-1/4Primary atom site location: structure-invariant immediate methodsExtinction coefficient: 0.014 (4) Open up in another window Special information Experimental. face-indexed (and goodness of suit derive from derive from place to zero for detrimental em F /em 2. The threshold appearance of em F /em 2 ( em F /em 2) can be used only for determining em R /em -elements(gt) em etc /em . and isn’t relevant to the decision of reflections for refinement. em R /em -elements predicated on em F /em 2 are statistically about doubly huge as those predicated on em F /em , and em R /em – elements predicated on ALL data will be even bigger. Open up in another screen Fractional atomic coordinates and equal or isotropic isotropic displacement variables (?2) em x /em em con /em em z /em em U /em iso*/ em U /em eqC20.2640 (2)?0.3204 (3)0.32882 (13)0.0425 (5)C30.21718 (19)?0.1773 (3)0.26133 (17)0.0490 (5)H3A0.1398?0.12960.27730.059*H3B0.2121?0.24380.20580.059*C40.3027 (2)?0.0043 (4)0.25750 (16)0.0590 (6)H4A0.26260.12270.26700.071*H4B0.34090.00030.20170.071*C50.3932 (2)?0.0428 (3)0.32948 (15)0.0466 (5)H50.4708?0.05780.30330.056*C60.40010 (17)0.1156 (3)0.40092 (13)0.0400 (4)H60.43400.23930.37710.048*C70.47970 (18)0.0382 (3)0.47386 (13)0.0421 (5)H70.55580.00750.44780.051*C80.4309 (2)?0.1608 (3)0.50890 (16)0.0514 (6)H8A0.4814?0.21000.55450.062*H8B0.3537?0.13780.53320.062*C90.4226 (2)?0.3184 (3)0.43821 (15)0.0557 (6)H9A0.5006?0.35690.41970.067*H9B0.3832?0.43750.46000.067*C100.50152 (16)0.1935 (3)0.54318 (14)0.0407 (5)C110.42606 (19)0.2235 (4)0.61193 (16)0.0507 (5)H110.35820.14640.61590.061*C120.4494 (2)0.3654 (4)0.67466 (16)0.0580 (6)H120.39760.38330.72030.070*C130.5498 (2)0.4808 (4)0.66972 (17)0.0599 (7)H130.56620.57540.71220.072*C140.6248 (2)0.4553 (4)0.60216 (17)0.0623 (7)H140.69190.53430.59820.075*C150.60156 (19)0.3120 (4)0.53928 (16)0.0501 (5)H150.65380.29510.49380.060*N10.35736 (17)?0.2359 (3)0.36550 (12)0.0473 (4)O10.22237 (14)?0.4869 (2)0.34724 (11)0.0545 (5)O20.28771 (12)0.1598 (2)0.43433 (11)0.0496 (4)H20.26470.26730.41460.074* Open up in another screen Atomic displacement parameters (?2) em U /em 11 em U /em 22 em U /em 33 em U /em 12 em U /em 13 em U /em 23C20.0503 (12)0.0381 (10)0.0391 (11)0.0064 (9)0.0004 (9)?0.0066 (9)C30.0507 (13)0.0483 (11)0.0480 (12)0.0040 (9)?0.0032 (10)0.0014 (10)C40.0858 (18)0.0477 (12)0.0436 (12)?0.0088 (11)?0.0148 (13)0.0042 (10)C50.0585 (13)0.0404 (10)0.0408 (10)?0.0013 (9)?0.0015 (10)0.0023 (9)C60.0488 (11)0.0331 (10)0.0382 (10)?0.0015 (8)0.0012 (9)0.0038 (8)C70.0395 (10)0.0449 (12)0.0419 (11)0.0035 (8)?0.0023 (9)?0.0003 (9)C80.0681 (15)0.0384 (11)0.0478 (11)0.0032 (10)?0.0163 (11)0.0054 (9)C90.0736 (15)0.0366 (11)0.0570 Nkx2-1 (14)0.0078 (9)?0.0211 (12)0.0039 (10)C100.0405 (10)0.0417 (11)0.0397 (10)0.0017 (8)?0.0059 (9)0.0024 (8)C110.0523 (11)0.0496 (12)0.0501 (12)0.0022 (9)0.0080 (11)?0.0004 (10)C120.0783 (16)0.0509 (12)0.0447 (12)0.0132 (12)0.0045 (12)?0.0045 (11)C130.0818 (17)0.0480 (12)0.0500 (13)0.0058 (11)?0.0209 (13)?0.0055 (11)C140.0621 (14)0.0556 (14)0.0693 (16)?0.0098 (11)?0.0195 (14)0.0004 (12)C150.0453 (11)0.0587 (13)0.0464 (12)?0.0024 (10)?0.0031 (10)0.0035 (10)N10.0593 (11)0.0359 (9)0.0465 (9)0.0005 (8)?0.0100 (8)0.0014 (8)O10.0640 (11)0.0413 (8)0.0582 (11)?0.0047 (6)?0.0065 (8)0.0027 (7)O20.0456 (8)0.0486 (8)0.0546 (9)0.0083 (6)0.0023 (7)0.0085 (7) Open up in another window Geometric variables (?, ) C2O11.237?(2)C8C91.518?(3)C2N11.332?(3)C8H8A0.9700C2C31.511?(3)C8H8B0.9700C3C41.508?(3)C9N11.458?(3)C3H3A0.9700C9H9A0.9700C3H3B0.9700C9H9B0.9700C4C51.542?(3)C10C111.385?(3)C4H4A0.9700C10C151.388?(3)C4H4B0.9700C11C121.380?(3)C5N11.457?(3)C11H110.9300C5C61.530?(3)C12C131.380?(4)C5H50.9800C12H120.9300C6O21.414?(2)C13C141.364?(4)C6C71.540?(3)C13H130.9300C6H60.9800C14C151.388?(3)C7C101.510?(3)C14H140.9300C7C81.533?(3)C15H150.9300C7H70.9800O2H20.8200O1C2N1125.78?(19)C9C8H8A109.4O1C2C3125.9?(2)C7C8H8A109.4N1C2C3108.33?(17)C9C8H8B109.4C2C3C4106.09?(18)C7C8H8B109.4C2C3H3A110.5H8AC8H8B108.0C4C3H3A110.5N1C9C8109.40?(16)C2C3H3B110.5N1C9H9A109.8C4C3H3B110.5C8C9H9A109.8H3AC3H3B108.7N1C9H9B109.8C3C4C5106.18?(18)C8C9H9B109.8C3C4H4A110.5H9AC9H9B108.2C5C4H4A110.5C11C10C15117.7?(2)C3C4H4B110.5C11C10C7122.92?(19)C5C4H4B110.5C15C10C7119.4?(2)H4AC4H4B108.7C10C11C12121.4?(2)N1C5C6109.98?(17)C10C11H11119.3N1C5C4103.63?(18)C12C11H11119.3C6C5C4116.45?(19)C13C12C11120.0?(2)N1C5H5108.8C13C12H12120.0C6C5H5108.8C11C12H12120.0C4C5H5108.8C14C13C12119.7?(2)O2C6C5111.15?(17)C14C13H13120.2O2C6C7109.59?(16)C12C13H13120.2C5C6C7109.49?(16)C13C14C15120.3?(2)O2C6H6108.9C13C14H14119.9C5C6H6108.9C15C14H14119.9C7C6H6108.9C10C15C14121.0?(2)C10C7C6113.12?(15)C10C15H15119.5C10C7C8113.31?(18)C14C15H15119.5C6C7C8109.48?(17)C2N1C5115.52?(17)C10C7H7106.8C2N1C9125.54?(18)C6C7H7106.8C5N1C9118.92?(18)C8C7H7106.8C6O2H2109.5C9C8C7111.1?(2)O1C2C3C4?175.3?(2)C8C7C10C15139.5?(2)N1C2C3C45.1?(2)C15C10C11C12?0.3?(3)C2C3C4C5?4.7?(2)C7C10C11C12179.3?(2)C3C4C5N12.8?(2)C10C11C12C13?0.1?(4)C3C4C5C6?118.0?(2)C11C12C13C140.7?(4)N1C5C6O2?67.5?(2)C12C13C14C15?1.0?(4)C4C5C6O250.0?(2)C11C10C15C140.0?(3)N1C5C6C753.7?(2)C7C10C15C14?179.6?(2)C4C5C6C7171.18?(18)C13C14C15C100.6?(3)O2C6C7C10?63.7?(2)O1C2N1C5176.9?(2)C5C6C7C10174.18?(17)C3C2N1C5?3.5?(2)O2C6C7C863.7?(2)O1C2N1C9?4.6?(3)C5C6C7C8?58.4?(2)C3C2N1C9175.0?(2)C10C7C8C9?174.06?(18)C6C5N1C2125.53?(19)C6C7C8C958.6?(2)C4C5N1C20.4?(2)C7C8C9N1?52.9?(3)C6C5N1C9?53.1?(3)C6C7C10C1185.3?(2)C4C5N1C9?178.2?(2)C8C7C10C11?40.0?(3)C8C9N1C2?126.4?(2)C6C7C10C15?95.1?(2)C8C9N1C552.1?(3) Open up in another screen Hydrogen-bond geometry (?, ) em D /em H em A /em em D /em HH em A /em em D /em em A /em em D /em H em A /em O2H2O1we0.822.002.807?(2)170 Open up in another window Symmetry rules: (i actually) em x /em , em con /em +1, em z /em . Footnotes Supplementary data and statistics because of this paper can be found in the IUCr digital archives (Guide: BG2260)..For comparison of mol-ecular variables, see: Camus (2003 ?); Lokaj (1999 ?); Dark brown & Corbridge (1954 ?); Pedersen (1967 ?). Molyneux & Adam (1982 ?); Harrell (1970 ?); Ruprecht (1989 ?); Liu (2007 ?); Smith (2007 ?); Gupta (2003 ?); Rosseels (1982 ?); Oslund (2008 ?); Ostby (2000 ?). For synthesis of indolizines, find: Chuprakov & Gevorgyan (2007 ?); Yan & Liu (2007 ?). For the synthesis strategies used, find: ?af? (2009 ?). For buildings linked to the name substance, see: ?vorc (2009 ?). For evaluation of mol-ecular variables, find: Camus (2003 ?); Lokaj (1999 ?); Dark brown & Corbridge (1954 ?); Pedersen (1967 ?). For an over-all evaluation of puckering, find: Cremer & Pople (1975 ?). Experimental Crystal data C14H17NO2 = 231.29 Orthorhombic, = 11.4164 (3) ? = 6.6372 (2) ? = 15.5118 (4) ? = 1175.38 (6) ?3 = 4 Mo = 298 K 0.60 0.56 0.13 mm Data collection Oxford Diffraction Gemini R CCD diffractometer Absorption modification: analytical (Clark & Reid, 1995 ?) 2(= 1.03 1632 reflections 157 variables 1 restraint H-atom variables constrained max = 0.17 e ??3 min = ?0.12 e ??3 Data collection: (Oxford Diffraction, 2006 ?); cell refinement: (Oxford Diffraction, 2006 ?); data decrease: (Sheldrick, 2008 ?); plan(s) utilized to refine framework: (Sheldrick, 2008 ?); molecular images: (Brandenburg, 2001 ?); software program used to get ready materials for publication: (Allen axis (Fig. 2) and help stabilize the crystal framework of the substance. Bond measures and sides in the indolizine band program are in great agreement with beliefs from the books (Camus = 231.29= Vilazodone 11.4164 (3) ? = 3.3C29.4= 6.6372 (2) ? = 0.09 mm?1= 15.5118 (4) ?= 298 K= 1175.38 (6) ?3Block, light= 40.60 0.56 0.13 mm Open up in another screen Data collection Oxford Diffraction Gemini R CCD diffractometer1632 separate reflectionsRadiation supply: fine-focus sealed pipe1128 reflections with 2(= ?1515Absorption correction: analytical (Clark & Reid, 1995)= ?99= ?202126298 measured reflections Open up in another window Refinement Refinement on = 1/[2(= (= 1.03(/)max 0.0011632 reflectionsmax = 0.17 e ??3157 parametersmin = ?0.12 e ??31 restraintExtinction correction: (Sheldrick, 2008), Fc*=kFc[1+0.001xFc23/sin(2)]-1/4Primary atom site location: structure-invariant immediate methodsExtinction coefficient: 0.014 (4) Open up in another window Special information Experimental. face-indexed (and goodness of suit derive from derive from place to zero for detrimental em F /em 2. The threshold appearance of em F /em 2 ( em F /em 2) can be used only for determining em R /em -elements(gt) em etc /em . and isn’t relevant to the decision of reflections for refinement. em R /em -elements predicated on em F /em 2 are statistically about doubly huge as those predicated on em F /em , and em R /em – elements predicated on ALL data will end up being even bigger. Open in a separate windows Fractional atomic coordinates and isotropic or comparative isotropic displacement guidelines (?2) em x /em em y /em em z /em em U /em iso*/ em U /em eqC20.2640 (2)?0.3204 (3)0.32882 (13)0.0425 (5)C30.21718 (19)?0.1773 (3)0.26133 (17)0.0490 (5)H3A0.1398?0.12960.27730.059*H3B0.2121?0.24380.20580.059*C40.3027 (2)?0.0043 (4)0.25750 (16)0.0590 (6)H4A0.26260.12270.26700.071*H4B0.34090.00030.20170.071*C50.3932 (2)?0.0428 (3)0.32948 (15)0.0466 (5)H50.4708?0.05780.30330.056*C60.40010 (17)0.1156 (3)0.40092 (13)0.0400 (4)H60.43400.23930.37710.048*C70.47970 (18)0.0382 (3)0.47386 (13)0.0421 (5)H70.55580.00750.44780.051*C80.4309 (2)?0.1608 (3)0.50890 (16)0.0514 (6)H8A0.4814?0.21000.55450.062*H8B0.3537?0.13780.53320.062*C90.4226 (2)?0.3184 (3)0.43821 Vilazodone (15)0.0557 (6)H9A0.5006?0.35690.41970.067*H9B0.3832?0.43750.46000.067*C100.50152 (16)0.1935 (3)0.54318 (14)0.0407 (5)C110.42606 (19)0.2235 (4)0.61193 (16)0.0507 (5)H110.35820.14640.61590.061*C120.4494 (2)0.3654 (4)0.67466 (16)0.0580 (6)H120.39760.38330.72030.070*C130.5498 (2)0.4808 (4)0.66972 (17)0.0599 (7)H130.56620.57540.71220.072*C140.6248 (2)0.4553 (4)0.60216 (17)0.0623 (7)H140.69190.53430.59820.075*C150.60156 (19)0.3120 (4)0.53928 (16)0.0501 (5)H150.65380.29510.49380.060*N10.35736 (17)?0.2359 (3)0.36550 (12)0.0473 (4)O10.22237 (14)?0.4869 (2)0.34724 (11)0.0545 (5)O20.28771 (12)0.1598 (2)0.43433 (11)0.0496 (4)H20.26470.26730.41460.074* Open in a separate windows Atomic displacement parameters (?2) em U /em 11 em U /em 22 em U /em 33 em U /em 12 em U /em 13 em U /em 23C20.0503 (12)0.0381 (10)0.0391 (11)0.0064 (9)0.0004 (9)?0.0066 (9)C30.0507 (13)0.0483 (11)0.0480 (12)0.0040 (9)?0.0032 (10)0.0014 (10)C40.0858 (18)0.0477 (12)0.0436 (12)?0.0088 (11)?0.0148 (13)0.0042 (10)C50.0585 (13)0.0404 (10)0.0408 (10)?0.0013 (9)?0.0015 (10)0.0023 (9)C60.0488 (11)0.0331 (10)0.0382 (10)?0.0015 (8)0.0012 (9)0.0038 (8)C70.0395 (10)0.0449 (12)0.0419 (11)0.0035 (8)?0.0023 (9)?0.0003 (9)C80.0681 (15)0.0384 (11)0.0478 (11)0.0032 (10)?0.0163 (11)0.0054 (9)C90.0736 (15)0.0366 (11)0.0570 (14)0.0078 (9)?0.0211 (12)0.0039 (10)C100.0405 (10)0.0417 (11)0.0397 (10)0.0017 (8)?0.0059 (9)0.0024 (8)C110.0523 (11)0.0496 (12)0.0501 (12)0.0022 (9)0.0080 (11)?0.0004 (10)C120.0783 (16)0.0509 (12)0.0447 (12)0.0132 (12)0.0045 (12)?0.0045 (11)C130.0818 (17)0.0480 (12)0.0500 (13)0.0058 (11)?0.0209 (13)?0.0055 (11)C140.0621 (14)0.0556 (14)0.0693 (16)?0.0098 (11)?0.0195 (14)0.0004 (12)C150.0453 (11)0.0587 (13)0.0464 (12)?0.0024 (10)?0.0031 (10)0.0035 (10)N10.0593 (11)0.0359 (9)0.0465 (9)0.0005 (8)?0.0100 (8)0.0014 (8)O10.0640 (11)0.0413 (8)0.0582 (11)?0.0047 (6)?0.0065 (8)0.0027 (7)O20.0456 (8)0.0486 (8)0.0546 (9)0.0083 (6)0.0023 (7)0.0085 (7) Open in a separate window Geometric guidelines (?, ) C2O11.237?(2)C8C91.518?(3)C2N11.332?(3)C8H8A0.9700C2C31.511?(3)C8H8B0.9700C3C41.508?(3)C9N11.458?(3)C3H3A0.9700C9H9A0.9700C3H3B0.9700C9H9B0.9700C4C51.542?(3)C10C111.385?(3)C4H4A0.9700C10C151.388?(3)C4H4B0.9700C11C121.380?(3)C5N11.457?(3)C11H110.9300C5C61.530?(3)C12C131.380?(4)C5H50.9800C12H120.9300C6O21.414?(2)C13C141.364?(4)C6C71.540?(3)C13H130.9300C6H60.9800C14C151.388?(3)C7C101.510?(3)C14H140.9300C7C81.533?(3)C15H150.9300C7H70.9800O2H20.8200O1C2N1125.78?(19)C9C8H8A109.4O1C2C3125.9?(2)C7C8H8A109.4N1C2C3108.33?(17)C9C8H8B109.4C2C3C4106.09?(18)C7C8H8B109.4C2C3H3A110.5H8AC8H8B108.0C4C3H3A110.5N1C9C8109.40?(16)C2C3H3B110.5N1C9H9A109.8C4C3H3B110.5C8C9H9A109.8H3AC3H3B108.7N1C9H9B109.8C3C4C5106.18?(18)C8C9H9B109.8C3C4H4A110.5H9AC9H9B108.2C5C4H4A110.5C11C10C15117.7?(2)C3C4H4B110.5C11C10C7122.92?(19)C5C4H4B110.5C15C10C7119.4?(2)H4AC4H4B108.7C10C11C12121.4?(2)N1C5C6109.98?(17)C10C11H11119.3N1C5C4103.63?(18)C12C11H11119.3C6C5C4116.45?(19)C13C12C11120.0?(2)N1C5H5108.8C13C12H12120.0C6C5H5108.8C11C12H12120.0C4C5H5108.8C14C13C12119.7?(2)O2C6C5111.15?(17)C14C13H13120.2O2C6C7109.59?(16)C12C13H13120.2C5C6C7109.49?(16)C13C14C15120.3?(2)O2C6H6108.9C13C14H14119.9C5C6H6108.9C15C14H14119.9C7C6H6108.9C10C15C14121.0?(2)C10C7C6113.12?(15)C10C15H15119.5C10C7C8113.31?(18)C14C15H15119.5C6C7C8109.48?(17)C2N1C5115.52?(17)C10C7H7106.8C2N1C9125.54?(18)C6C7H7106.8C5N1C9118.92?(18)C8C7H7106.8C6O2H2109.5C9C8C7111.1?(2)O1C2C3C4?175.3?(2)C8C7C10C15139.5?(2)N1C2C3C45.1?(2)C15C10C11C12?0.3?(3)C2C3C4C5?4.7?(2)C7C10C11C12179.3?(2)C3C4C5N12.8?(2)C10C11C12C13?0.1?(4)C3C4C5C6?118.0?(2)C11C12C13C140.7?(4)N1C5C6O2?67.5?(2)C12C13C14C15?1.0?(4)C4C5C6O250.0?(2)C11C10C15C140.0?(3)N1C5C6C753.7?(2)C7C10C15C14?179.6?(2)C4C5C6C7171.18?(18)C13C14C15C100.6?(3)O2C6C7C10?63.7?(2)O1C2N1C5176.9?(2)C5C6C7C10174.18?(17)C3C2N1C5?3.5?(2)O2C6C7C863.7?(2)O1C2N1C9?4.6?(3)C5C6C7C8?58.4?(2)C3C2N1C9175.0?(2)C10C7C8C9?174.06?(18)C6C5N1C2125.53?(19)C6C7C8C958.6?(2)C4C5N1C20.4?(2)C7C8C9N1?52.9?(3)C6C5N1C9?53.1?(3)C6C7C10C1185.3?(2)C4C5N1C9?178.2?(2)C8C7C10C11?40.0?(3)C8C9N1C2?126.4?(2)C6C7C10C15?95.1?(2)C8C9N1C552.1?(3) Open in a separate windows Hydrogen-bond geometry (?, ) em D /em H em A /em em D /em HH em A /em em D /em em A /em em D /em H em A /em O2H2O1i0.822.002.807?(2)170 Open in a separate window Symmetry codes: (we) em x /em , em y /em +1, em z /em . Footnotes Supplementary data and numbers for this paper are available from your IUCr electronic archives (Research: BG2260)..