For reference bond-length data, see: Allen (1987 ?)

For reference bond-length data, see: Allen (1987 ?). Experimental Crystal data C28H22ClFN6O2 = 528.97 Monoclinic, = 9.9221 (3) ? = 21.3339 (7) ? = 12.7201 (4) ? = 111.629 (1) = 2502.97 (14) ?3 = 4 Mo = 100 K 0.36 0.26 0.08 mm Data collection Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan ( 2(= 1.07 5660 reflections 347 guidelines H atoms treated by a mixture of independent and constrained refinement maximum = 0.26 e ??3 min = ?0.35 e ??3 Data collection: (Bruker, 2009 ?); cell refinement: (Bruker, 2009 ?); data reduction: (Sheldrick, 2008 ?); system(s) used to refine structure: and (Spek, 2009 ?). ? Table 1 Hydrogen-bond geometry (?, ) aircraft. Experimental The compound has been synthesized using a method reported in the literature (Ragavan = 485.3C486 K. Refinement Atom H1N5 was located in a difference Fourier map and was processed freely [NH = 0.87 (3) ?]. The remaining H atoms were situated geometrically [CH = 0.93 or 0.97 ?] and were processed using a using model, with = 528.97= 9.9221 (3) ? = 2.4C27.3= 21.3339 (7) ? = 0.20 mm?1= 12.7201 (4) ?= 100 K = 111.629 (1)Plate, colourless= 2502.97 (14) ?30.36 0.26 0.08 mm= 4 Open in a separate window Data collection Bruker SMART APEXII CCD area-detector diffractometer5660 independent reflectionsRadiation resource: fine-focus sealed tube4272 reflections with 2(= ?1211= ?272419192 measured reflections= ?1416 Open in a separate window Refinement Refinement on = 1.07= 1/[2(= (and goodness of fit are based on are based on set to zero for bad em F /em 2. The threshold manifestation of em F /em 2 ( em F /em 2) is used only for calculating em R /em -factors(gt) em etc /em . and is not relevant to the choice of reflections for refinement. em R /em -factors based on em F /em 2 are statistically about twice as large as those based on em F /em , and em R /em – factors based on ALL data will become even larger. Open in a separate windowpane Fractional atomic coordinates and isotropic or equal isotropic displacement guidelines (?2) em x /em em y /em em z /em em U /em iso*/ em U /em eqCl10.47534 (7)0.60803 (3)0.78980 (5)0.03029 (16)F10.48142 (15)0.22562 (7)0.89619 (12)0.0304 (3)N10.81146 (19)0.34593 (9)0.69103 (14)0.0161 (4)N20.89747 (19)0.31063 (9)0.65254 (14)0.0164 (4)N31.04762 (19)0.34908 (9)0.44459 (14)0.0174 (4)N41.0136 (2)0.35012 (9)0.21385 (15)0.0203 (4)N51.1177 (2)0.35113 (10)0.07780 (16)0.0194 (4)N61.2635 (2)0.45747 (11)?0.37105 (17)0.0335 (5)O11.14153 (16)0.28689 (7)0.59902 (12)0.0193 (3)O20.91589 (17)0.41027 (8)0.05706 (13)0.0236 (4)C10.7918 (2)0.29390 (11)0.85563 (18)0.0197 (5)H1A0.89050.29990.89480.024*C20.7083 (2)0.26399 (11)0.90742 (19)0.0220 (5)H2A0.74930.25030.98190.026*C30.5637 (2)0.25525 (11)0.84547 (19)0.0216 (5)C40.4962 (2)0.27504 (11)0.73509 (19)0.0228 (5)H4A0.39780.26810.69590.027*C50.5800 (2)0.30562 (11)0.68465 (18)0.0203 (5)H5A0.53800.32000.61060.024*C60.7266 (2)0.31466 (10)0.74509 (18)0.0163 (5)C70.7134 (2)0.45597 (11)0.79798 (18)0.0209 (5)H7A0.75930.42460.84940.025*C80.6372 (2)0.50256 (11)0.82822 (19)0.0227 (5)H8A0.63030.50210.89920.027*C90.5715 (2)0.54962 (11)0.75187 (19)0.0213 (5)C100.5806 (2)0.55132 (11)0.64628 (19)0.0218 (5)H10A0.53650.58350.59610.026*C110.6562 (2)0.50443 (11)0.61567 (18)0.0194 (5)H11A0.66290.50540.54470.023*C120.7220 (2)0.45589 (11)0.69021 (18)0.0177 (5)C130.8020 (2)0.40700 (11)0.65574 (17)0.0166 (5)C140.8854 (2)0.41079 (11)0.58986 (17)0.0176 (5)H14A0.90070.44600.55260.021*C150.9423 (2)0.35043 (11)0.59080 (17)0.0163 (5)C161.0502 (2)0.32613 (10)0.54447 (17)0.0157 (4)C171.1727 (2)0.33981 (11)0.41143 (18)0.0192 (5)H17A1.24160.31200.46520.023*H17B1.22040.37970.41340.023*C181.1283 Rabbit polyclonal to AFF3 (2)0.31192 (11)0.29329 (17)0.0205 (5)H18A1.21120.31070.27030.025*H18B1.09390.26940.29340.025*C190.8884 (2)0.35880 (11)0.24632 (18)0.0202 (5)H19A0.84190.31870.24490.024*H19B0.81890.38610.19210.024*C200.9325 (2)0.38715 (11)0.36402 (17)0.0195 (5)H20A0.96680.42970.36340.023*H20B0.84930.38860.38670.023*C211.0089 (2)0.37302 (11)0.11281 (18)0.0179 (5)C221.1497 (2)0.37577 (11)?0.01271 (17)0.0185 (5)C231.2352 (3)0.33979 (11)?0.05514 (19)0.0235 (5)H23A1.26880.3009?0.02300.028*C241.2707 (3)0.36094 (12)?0.1441 (2)0.0261 (5)H24A1.32680.3361?0.17220.031*C251.2229 (2)0.41924 (11)?0.19194 (18)0.0204 (5)C261.1417 (3)0.45604 (12)?0.1474 (2)0.0255 (5)H26A1.11150.4956?0.17750.031*C271.1050 (3)0.43481 (11)?0.0591 (2)0.0247 (5)H27A1.05020.4600?0.03040.030*C281.2494 (3)0.44038 (12)?0.29033 (19)0.0242 (5)H1N51.148 (3)0.3133 (14)0.098 (2)0.033 (8)* Open in a separate windowpane Atomic displacement guidelines (?2) em U /em 11 em U /em 22 em U /em 33 em U /em 12 em U /em 13 em U /em 23Cl10.0278 (3)0.0295 (4)0.0347 (3)0.0067 (3)0.0129 (3)?0.0071 (3)F10.0281 (8)0.0372 (9)0.0311 (8)?0.0038 (7)0.0170 (6)0.0075 (7)N10.0167 (9)0.0172 (10)0.0156 (9)0.0006 (8)0.0074 (7)0.0003 (8)N20.0161 (9)0.0184 (10)0.0156 (9)?0.0001 (8)0.0069 (7)?0.0017 (8)N30.0154 (9)0.0217 (10)0.0151 (9)0.0004 (8)0.0056 (7)0.0006 (8)N40.0192 (10)0.0268 (11)0.0163 (9)0.0060 (8)0.0081 (7)0.0040 (8)N50.0244 (11)0.0174 (11)0.0190 (9)0.0042 (9)0.0110 (8)0.0024 (8)N60.0404 (13)0.0391 (14)0.0255 (11)?0.0110 (11)0.0175 (10)?0.0008 (10)O10.0193 (8)0.0207 (9)0.0175 (8)0.0024 (7)0.0063 (6)0.0022 (7)O20.0264 (9)0.0278 (10)0.0190 (8)0.0088 (7)0.0111 (7)0.0068 (7)C10.0176 (11)0.0217 (13)0.0187 (11)0.0025 (9)0.0055 (9)0.0024 (9)C20.0236 (12)0.0258 (14)0.0167 (11)0.0039 (10)0.0076 (9)0.0062 (10)C30.0255 (13)0.0209 (13)0.0237 (11)?0.0025 (10)0.0153 (10)0.0007 (10)C40.0152 (11)0.0278 (14)0.0241 (12)?0.0018 (10)0.0058 (9)?0.0017 (10)C50.0214 (12)0.0241 (13)0.0148 (10)0.0016 (10)0.0060 (9)0.0011 (10)C60.0191 (11)0.0147 (11)0.0176 (10)0.0008 (9)0.0096 (9)?0.0004 (9)C70.0233 (12)0.0220 (13)0.0165 (10)0.0017 (10)0.0062 (9)?0.0002 (10)C80.0253 (12)0.0255 (13)0.0190 (11)?0.0005 (10)0.0102 (9)?0.0040 (10)C90.0162 (11)0.0194 (12)0.0279 (12)?0.0015 (9)0.0076 (9)?0.0064 (10)C100.0188 (12)0.0188 (13)0.0262 (12)0.0011 (10)0.0063 (9)0.0028 (10)C110.0179 (11)0.0211 (13)0.0189 (10)?0.0033 (9)0.0064 (8)?0.0005 (9)C120.0167 (11)0.0170 (12)0.0198 (10)?0.0033 (9)0.0073 (8)?0.0043 (9)C130.0172 (11)0.0173 (12)0.0131 (10)?0.0010 (9)0.0030 (8)?0.0008 (9)C140.0192 (11)0.0181 (12)0.0163 (10)?0.0030 (9)0.0076 (9)?0.0009 (9)C150.0167 (11)0.0185 (12)0.0124 (10)?0.0027 (9)0.0038 (8)?0.0016 (9)C160.0160 (11)0.0164 (12)0.0139 (10)?0.0046 (9)0.0045 (8)?0.0041 (9)C170.0164 (11)0.0245 (13)0.0170 (10)?0.0016 (9)0.0066 (9)0.0003 (10)C180.0201 (12)0.0274 (13)0.0154 (10)0.0049 (10)0.0083 (9)0.0025 (10)C190.0177 (11)0.0265 (13)0.0165 (10)0.0026 (10)0.0064 (9)0.0027 (10)C200.0192 (11)0.0226 (13)0.0176 (10)0.0035 (10)0.0080 (9)0.0020 (9)C210.0185 (11)0.0184 (12)0.0164 (10)?0.0021 (9)0.0060 (9)?0.0023 (9)C220.0207 (12)0.0224 (13)0.0119 (10)?0.0030 (10)0.0056 (8)?0.0028 (9)C230.0296 (13)0.0205 (13)0.0227.The threshold expression of em F /em 2 ( em F /em 2) is used only for 4-Methylumbelliferone (4-MU) calculating em R /em -factors(gt) em etc /em . and is not relevant to the choice of reflections for refinement. em R /em -factors based on em F /em 2 are statistically about twice as large as those based on em F /em , and em R /em – reasons based on ALL data will be even larger. Open in a separate window Fractional atomic coordinates and isotropic or equal isotropic displacement parameters (?2) em x /em em y /em em z /em em U /em iso*/ em U /em eqCl10.47534 (7)0.60803 (3)0.78980 (5)0.03029 (16)F10.48142 (15)0.22562 (7)0.89619 (12)0.0304 (3)N10.81146 (19)0.34593 (9)0.69103 (14)0.0161 (4)N20.89747 (19)0.31063 (9)0.65254 (14)0.0164 (4)N31.04762 (19)0.34908 (9)0.44459 (14)0.0174 (4)N41.0136 (2)0.35012 (9)0.21385 (15)0.0203 (4)N51.1177 (2)0.35113 (10)0.07780 (16)0.0194 (4)N61.2635 (2)0.45747 (11)?0.37105 (17)0.0335 (5)O11.14153 (16)0.28689 (7)0.59902 (12)0.0193 (3)O20.91589 (17)0.41027 (8)0.05706 (13)0.0236 (4)C10.7918 (2)0.29390 (11)0.85563 (18)0.0197 (5)H1A0.89050.29990.89480.024*C20.7083 (2)0.26399 (11)0.90742 (19)0.0220 (5)H2A0.74930.25030.98190.026*C30.5637 (2)0.25525 (11)0.84547 (19)0.0216 (5)C40.4962 (2)0.27504 (11)0.73509 (19)0.0228 (5)H4A0.39780.26810.69590.027*C50.5800 (2)0.30562 (11)0.68465 (18)0.0203 (5)H5A0.53800.32000.61060.024*C60.7266 (2)0.31466 (10)0.74509 (18)0.0163 (5)C70.7134 (2)0.45597 (11)0.79798 (18)0.0209 (5)H7A0.75930.42460.84940.025*C80.6372 (2)0.50256 (11)0.82822 (19)0.0227 (5)H8A0.63030.50210.89920.027*C90.5715 (2)0.54962 (11)0.75187 (19)0.0213 (5)C100.5806 (2)0.55132 (11)0.64628 (19)0.0218 (5)H10A0.53650.58350.59610.026*C110.6562 (2)0.50443 (11)0.61567 (18)0.0194 (5)H11A0.66290.50540.54470.023*C120.7220 (2)0.45589 (11)0.69021 (18)0.0177 (5)C130.8020 (2)0.40700 (11)0.65574 (17)0.0166 (5)C140.8854 (2)0.41079 (11)0.58986 (17)0.0176 (5)H14A0.90070.44600.55260.021*C150.9423 (2)0.35043 (11)0.59080 (17)0.0163 (5)C161.0502 (2)0.32613 (10)0.54447 (17)0.0157 (4)C171.1727 (2)0.33981 (11)0.41143 (18)0.0192 (5)H17A1.24160.31200.46520.023*H17B1.22040.37970.41340.023*C181.1283 (2)0.31192 (11)0.29329 (17)0.0205 (5)H18A1.21120.31070.27030.025*H18B1.09390.26940.29340.025*C190.8884 (2)0.35880 (11)0.24632 (18)0.0202 (5)H19A0.84190.31870.24490.024*H19B0.81890.38610.19210.024*C200.9325 (2)0.38715 (11)0.36402 (17)0.0195 (5)H20A0.96680.42970.36340.023*H20B0.84930.38860.38670.023*C211.0089 (2)0.37302 (11)0.11281 (18)0.0179 (5)C221.1497 (2)0.37577 (11)?0.01271 (17)0.0185 (5)C231.2352 (3)0.33979 (11)?0.05514 (19)0.0235 (5)H23A1.26880.3009?0.02300.028*C241.2707 (3)0.36094 (12)?0.1441 (2)0.0261 (5)H24A1.32680.3361?0.17220.031*C251.2229 (2)0.41924 (11)?0.19194 (18)0.0204 (5)C261.1417 (3)0.45604 (12)?0.1474 (2)0.0255 (5)H26A1.11150.4956?0.17750.031*C271.1050 (3)0.43481 (11)?0.0591 (2)0.0247 (5)H27A1.05020.4600?0.03040.030*C281.2494 (3)0.44038 (12)?0.29033 (19)0.0242 (5)H1N51.148 (3)0.3133 (14)0.098 (2)0.033 (8)* Open in a separate 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 23Cl10.0278 (3)0.0295 (4)0.0347 (3)0.0067 (3)0.0129 (3)?0.0071 (3)F10.0281 (8)0.0372 (9)0.0311 (8)?0.0038 (7)0.0170 (6)0.0075 (7)N10.0167 (9)0.0172 (10)0.0156 (9)0.0006 (8)0.0074 (7)0.0003 (8)N20.0161 (9)0.0184 (10)0.0156 (9)?0.0001 (8)0.0069 (7)?0.0017 (8)N30.0154 (9)0.0217 (10)0.0151 (9)0.0004 (8)0.0056 (7)0.0006 (8)N40.0192 (10)0.0268 (11)0.0163 (9)0.0060 (8)0.0081 (7)0.0040 (8)N50.0244 (11)0.0174 (11)0.0190 (9)0.0042 (9)0.0110 (8)0.0024 (8)N60.0404 (13)0.0391 (14)0.0255 (11)?0.0110 (11)0.0175 (10)?0.0008 (10)O10.0193 (8)0.0207 (9)0.0175 (8)0.0024 (7)0.0063 (6)0.0022 (7)O20.0264 (9)0.0278 (10)0.0190 (8)0.0088 (7)0.0111 (7)0.0068 (7)C10.0176 (11)0.0217 (13)0.0187 (11)0.0025 (9)0.0055 (9)0.0024 (9)C20.0236 (12)0.0258 (14)0.0167 (11)0.0039 (10)0.0076 (9)0.0062 (10)C30.0255 (13)0.0209 (13)0.0237 (11)?0.0025 (10)0.0153 (10)0.0007 (10)C40.0152 (11)0.0278 (14)0.0241 (12)?0.0018 (10)0.0058 (9)?0.0017 (10)C50.0214 (12)0.0241 (13)0.0148 (10)0.0016 (10)0.0060 (9)0.0011 (10)C60.0191 (11)0.0147 (11)0.0176 (10)0.0008 (9)0.0096 (9)?0.0004 (9)C70.0233 (12)0.0220 (13)0.0165 (10)0.0017 (10)0.0062 (9)?0.0002 (10)C80.0253 (12)0.0255 (13)0.0190 (11)?0.0005 (10)0.0102 (9)?0.0040 (10)C90.0162 (11)0.0194 (12)0.0279 (12)?0.0015 (9)0.0076 (9)?0.0064 (10)C100.0188 (12)0.0188 (13)0.0262 (12)0.0011 (10)0.0063 (9)0.0028 (10)C110.0179 (11)0.0211 (13)0.0189 (10)?0.0033 (9)0.0064 (8)?0.0005 (9)C120.0167 (11)0.0170 (12)0.0198 (10)?0.0033 (9)0.0073 (8)?0.0043 (9)C130.0172 (11)0.0173 (12)0.0131 (10)?0.0010 (9)0.0030 (8)?0.0008 (9)C140.0192 (11)0.0181 (12)0.0163 (10)?0.0030 (9)0.0076 (9)?0.0009 (9)C150.0167 (11)0.0185 (12)0.0124 (10)?0.0027 (9)0.0038 (8)?0.0016 (9)C160.0160 (11)0.0164 (12)0.0139 (10)?0.0046 (9)0.0045 (8)?0.0041 (9)C170.0164 (11)0.0245 (13)0.0170 (10)?0.0016 (9)0.0066 (9)0.0003 (10)C180.0201 (12)0.0274 (13)0.0154 (10)0.0049 (10)0.0083 (9)0.0025 (10)C190.0177 (11)0.0265 (13)0.0165 (10)0.0026 (10)0.0064 (9)0.0027 (10)C200.0192 (11)0.0226 (13)0.0176 (10)0.0035 (10)0.0080 (9)0.0020 (9)C210.0185 (11)0.0184 (12)0.0164 (10)?0.0021 (9)0.0060 (9)?0.0023 (9)C220.0207 (12)0.0224 (13)0.0119 (10)?0.0030 (10)0.0056 (8)?0.0028 (9)C230.0296 (13)0.0205 (13)0.0227 (11)0.0054 (10)0.0124 (10)0.0034 (10)C240.0289 (13)0.0304 (15)0.0233 (12)0.0052 (11)0.0146 (10)?0.0003 (11)C250.0220 (12)0.0234 (13)0.0161 (10)?0.0040 (10)0.0076 (9)?0.0015 (9)C260.0349 (14)0.0199 (13)0.0250 (12)0.0020 (11)0.0150 (10)0.0028 (10)C270.0339 (14)0.0200 (13)0.0259 (12)0.0034 (11)0.0179 (11)0.0004 (10)C280.0252 (13)0.0265 (14)0.0203 (12)?0.0063 (10)0.0077 (10)?0.0034 (10) Open in a separate window Geometric parameters (?, ) Cl1C91.742?(2)C8H8A0.9300F1C31.367?(2)C9C101.379?(3)N1N21.358?(2)C10C111.389?(3)N1C131.370?(3)C10H10A0.9300N1C61.433?(3)C11C121.393?(3)N2C151.339?(3)C11H11A0.9300N3C161.353?(3)C12C131.472?(3)N3C171.464?(3)C13C141.380?(3)N3C201.467?(3)C14C151.405?(3)N4C211.360?(3)C14H14A0.9300N4C191.458?(3)C15C161.492?(3)N4C181.460?(3)C17C181.523?(3)N5C211.392?(3)C17H17A0.9700N5C221.404?(3)C17H17B0.9700N5H1N50.87?(3)C18H18A0.9700N6C281.146?(3)C18H18B0.9700O1C161.241?(3)C19C201.522?(3)O2C211.226?(3)C19H19A0.9700C1C61.386?(3)C19H19B0.9700C1C21.389?(3)C20H20A0.9700C1H1A0.9300C20H20B0.9700C2C31.372?(3)C22C231.392?(3)C2H2A0.9300C22C271.392?(3)C3C41.380?(3)C23C241.380?(3)C4C51.386?(3)C23H23A0.9300C4H4A0.9300C24C251.389?(3)C5C61.386?(3)C24H24A0.9300C5H5A0.9300C25C261.387?(3)C7C81.387?(3)C25C281.443?(3)C7C121.404?(3)C26C271.378?(3)C7H7A0.9300C26H26A0.9300C8C91.382?(3)C27H27A0.9300N2N1C13112.69?(17)C15C14H14A127.2N2N1C6118.25?(17)N2C15C14111.51?(18)C13N1C6128.21?(18)N2C15C16116.95?(19)C15N2N1104.40?(17)C14C15C16131.30?(19)C16N3C17119.79?(18)O1C16N3121.78?(19)C16N3C20126.63?(18)O1C16C15119.71?(18)C17N3C20113.48?(17)N3C16C15118.49?(19)C21N4C19119.10?(18)N3C17C18111.66?(17)C21N4C18126.94?(18)N3C17H17A109.3C19N4C18113.76?(17)C18C17H17A109.3C21N5C22125.0?(2)N3C17H17B109.3C21N5H1N5116.6?(18)C18C17H17B109.3C22N5H1N5115.4?(18)H17AC17H17B108.0C6C1C2119.4?(2)N4C18C17109.47?(18)C6C1H1A120.3N4C18H18A109.8C2C1H1A120.3C17C18H18A109.8C3C2C1118.1?(2)N4C18H18B109.8C3C2H2A121.0C17C18H18B109.8C1C2H2A121.0H18AC18H18B108.2F1C3C2118.2?(2)N4C19C20111.31?(18)F1C3C4118.1?(2)N4C19H19A109.4C2C3C4123.7?(2)C20C19H19A109.4C3C4C5117.8?(2)N4C19H19B109.4C3C4H4A121.1C20C19H19B109.4C5C4H4A121.1H19AC19H19B108.0C6C5C4119.7?(2)N3C20C19109.55?(18)C6C5H5A120.2N3C20H20A109.8C4C5H5A120.2C19C20H20A109.8C5C6C1121.3?(2)N3C20H20B109.8C5C6N1118.75?(19)C19C20H20B109.8C1C6N1119.91?(19)H20AC20H20B108.2C8C7C12120.5?(2)O2C21N4122.4?(2)C8C7H7A119.8O2C21N5122.7?(2)C12C7H7A119.8N4C21N5114.94?(19)C9C8C7119.3?(2)C23C22C27118.6?(2)C9C8H8A120.3C23C22N5117.7?(2)C7C8H8A120.3C27C22N5123.6?(2)C10C9C8121.4?(2)C24C23C22121.0?(2)C10C9Cl1119.32?(18)C24C23H23A119.5C8C9Cl1119.31?(18)C22C23H23A119.5C9C10C11119.3?(2)C23C24C25120.2?(2)C9C10H10A120.3C23C24H24A119.9C11C10H10A120.3C25C24H24A119.9C10C11C12120.7?(2)C26C25C24119.0?(2)C10C11H11A119.7C26C25C28119.8?(2)C12C11H11A119.7C24C25C28121.2?(2)C11C12C7118.8?(2)C27C26C25121.0?(2)C11C12C13119.52?(19)C27C26H26A119.5C7C12C13121.7?(2)C25C26H26A119.5N1C13C14105.71?(19)C26C27C22120.3?(2)N1C13C12123.74?(19)C26C27H27A119.9C14C13C12130.5?(2)C22C27H27A119.9C13C14C15105.69?(19)N6C28C25176.8?(3)C13C14H14A127.2C13N1N2C15?0.5?(2)C13C14C15N20.4?(2)C6N1N2C15169.86?(18)C13C14C15C16?173.7?(2)C6C1C2C31.1?(3)C17N3C16O1?14.7?(3)C1C2C3F1179.8?(2)C20N3C16O1169.2?(2)C1C2C3C4?0.7?(4)C17N3C16C15163.51?(19)F1C3C4C5179.3?(2)C20N3C16C15?12.6?(3)C2C3C4C5?0.2?(4)N2C15C16O1?33.1?(3)C3C4C5C60.7?(3)C14C15C16O1140.7?(2)C4C5C6C1?0.2?(3)N2C15C16N3148.6?(2)C4C5C6N1179.5?(2)C14C15C16N3?37.6?(3)C2C1C6C5?0.7?(3)C16N3C17C18128.3?(2)C2C1C6N1179.6?(2)C20N3C17C18?55.1?(3)N2N1C6C5?102.4?(2)C21N4C18C17130.4?(2)C13N1C6C566.2?(3)C19N4C18C17?54.9?(2)N2N1C6C177.3?(3)N3C17C18N453.1?(2)C13N1C6C1?114.1?(2)C21N4C19C20?128.6?(2)C12C7C8C9?1.1?(3)C18N4C19C2056.3?(3)C7C8C9C10?0.2?(4)C16N3C20C19?129.4?(2)C7C8C9Cl1179.84?(18)C17N3C20C1954.4?(2)C8C9C10C110.6?(3)N4C19C20N3?53.7?(2)Cl1C9C10C11?179.42?(17)C19N4C21O213.6?(3)C9C10C11C120.3?(3)C18N4C21O2?172.0?(2)C10C11C12C7?1.5?(3)C19N4C21N5?166.6?(2)C10C11C12C13?179.7?(2)C18N4C21N57.9?(3)C8C7C12C111.9?(3)C22N5C21O211.2?(3)C8C7C12C13?179.9?(2)C22N5C21N4?168.7?(2)N2N1C13C140.7?(2)C21N5C22C23?164.2?(2)C6N1C13C14?168.42?(19)C21N5C22C2718.1?(3)N2N1C13C12?176.73?(18)C27C22C23C24?2.4?(4)C6N1C13C1214.1?(3)N5C22C23C24179.8?(2)C11C12C13N1?148.1?(2)C22C23C24C250.9?(4)C7C12C13N133.7?(3)C23C24C25C261.2?(4)C11C12C13C1435.1?(3)C23C24C25C28?175.3?(2)C7C12C13C14?143.0?(2)C24C25C26C27?1.8?(4)N1C13C14C15?0.6?(2)C28C25C26C27174.8?(2)C12C13C14C15176.6?(2)C25C26C27C220.2?(4)N1N2C15C140.0?(2)C23C22C27C261.8?(3)N1N2C15C16175.01?(17)N5C22C27C26179.4?(2) Open in a separate window 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 N5H1N5O1i0.87?(3)2.14?(3)2.958?(3)157?(2)C2H2AN2ii0.932.493.386?(3)161C4H4AO1iii0.932.423.310?(3)161C7H7AO2iv0.932.543.312?(3)140 Open in a separate window Symmetry codes: (we) em x /em , ? em y /em +1/2, em z /em ?1/2; (ii) em x /em , ? em y /em +1/2, em z /em +1/2; (iii) em x /em ?1, em y /em , em z /em ; (iv) em x /em , em y /em , em z /em +1. Footnotes Supplementary data and figures for this paper are available from your IUCr electronic archives (Research: WN2409).. data, observe: Allen (1987 ?). For related constructions, observe: Fun (2010 ?); Shahani (2010 ?). For the stability of the temp controller used in the data collection, observe: Cosier & Glazer (1986 ?). Experimental Crystal data C28H22ClFN6O2 = 528.97 Monoclinic, = 9.9221 (3) ? = 21.3339 (7) ? = 12.7201 (4) ? = 111.629 (1) = 2502.97 (14) ?3 = 4 Mo = 100 K 0.36 0.26 0.08 mm Data collection Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan ( 2(= 1.07 5660 reflections 347 guidelines H atoms treated by a mixture of independent and constrained refinement maximum = 0.26 e ??3 min = ?0.35 e ??3 Data collection: (Bruker, 2009 ?); cell refinement: (Bruker, 2009 ?); data reduction: (Sheldrick, 2008 ?); system(s) used to refine structure: and (Spek, 2009 ?). ? Table 1 4-Methylumbelliferone (4-MU) Hydrogen-bond geometry (?, ) aircraft. Experimental The compound has been synthesized using a method reported in the literature (Ragavan = 485.3C486 K. Refinement Atom H1N5 was located in a difference Fourier map and was processed freely [NH = 0.87 (3) ?]. The remaining H atoms were situated geometrically [CH = 0.93 or 0.97 ?] and were processed using a operating model, with = 528.97= 9.9221 (3) ? = 2.4C27.3= 21.3339 (7) ? = 0.20 mm?1= 12.7201 (4) ?= 100 K = 111.629 (1)Dish, colourless= 2502.97 (14) ?30.36 0.26 0.08 mm= 4 Open up in another window Data collection Bruker SMART APEXII CCD area-detector diffractometer5660 independent reflectionsRadiation supply: fine-focus covered pipe4272 reflections with 2(= ?1211= ?272419192 measured reflections= ?1416 Open up in another window Refinement Refinement on = 1.07= 1/[2(= (and goodness of in shape derive from derive from set to no for harmful 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 4-Methylumbelliferone (4-MU) those predicated on em F /em , and em R /em – elements predicated on ALL data will be even bigger. Open in another home window Fractional atomic coordinates and isotropic or comparable isotropic displacement variables (?2) em x /em em con /em em z /em em U /em iso*/ em U /em eqCl10.47534 (7)0.60803 (3)0.78980 (5)0.03029 (16)F10.48142 (15)0.22562 (7)0.89619 (12)0.0304 (3)N10.81146 (19)0.34593 (9)0.69103 (14)0.0161 (4)N20.89747 (19)0.31063 (9)0.65254 (14)0.0164 (4)N31.04762 (19)0.34908 (9)0.44459 (14)0.0174 (4)N41.0136 (2)0.35012 (9)0.21385 (15)0.0203 (4)N51.1177 (2)0.35113 (10)0.07780 (16)0.0194 (4)N61.2635 (2)0.45747 (11)?0.37105 (17)0.0335 (5)O11.14153 (16)0.28689 (7)0.59902 (12)0.0193 (3)O20.91589 (17)0.41027 (8)0.05706 (13)0.0236 (4)C10.7918 (2)0.29390 (11)0.85563 (18)0.0197 (5)H1A0.89050.29990.89480.024*C20.7083 (2)0.26399 (11)0.90742 (19)0.0220 (5)H2A0.74930.25030.98190.026*C30.5637 (2)0.25525 (11)0.84547 (19)0.0216 (5)C40.4962 (2)0.27504 (11)0.73509 (19)0.0228 (5)H4A0.39780.26810.69590.027*C50.5800 (2)0.30562 (11)0.68465 (18)0.0203 (5)H5A0.53800.32000.61060.024*C60.7266 (2)0.31466 (10)0.74509 (18)0.0163 (5)C70.7134 (2)0.45597 (11)0.79798 (18)0.0209 (5)H7A0.75930.42460.84940.025*C80.6372 (2)0.50256 (11)0.82822 (19)0.0227 (5)H8A0.63030.50210.89920.027*C90.5715 (2)0.54962 (11)0.75187 (19)0.0213 (5)C100.5806 (2)0.55132 (11)0.64628 (19)0.0218 (5)H10A0.53650.58350.59610.026*C110.6562 (2)0.50443 (11)0.61567 (18)0.0194 (5)H11A0.66290.50540.54470.023*C120.7220 (2)0.45589 (11)0.69021 (18)0.0177 (5)C130.8020 (2)0.40700 (11)0.65574 (17)0.0166 (5)C140.8854 (2)0.41079 (11)0.58986 (17)0.0176 (5)H14A0.90070.44600.55260.021*C150.9423 (2)0.35043 (11)0.59080 (17)0.0163 (5)C161.0502 (2)0.32613 (10)0.54447 (17)0.0157 (4)C171.1727 (2)0.33981 (11)0.41143 (18)0.0192 (5)H17A1.24160.31200.46520.023*H17B1.22040.37970.41340.023*C181.1283 (2)0.31192 (11)0.29329 (17)0.0205 (5)H18A1.21120.31070.27030.025*H18B1.09390.26940.29340.025*C190.8884 (2)0.35880 (11)0.24632 (18)0.0202 (5)H19A0.84190.31870.24490.024*H19B0.81890.38610.19210.024*C200.9325 (2)0.38715 (11)0.36402 (17)0.0195 (5)H20A0.96680.42970.36340.023*H20B0.84930.38860.38670.023*C211.0089 (2)0.37302 (11)0.11281 (18)0.0179 (5)C221.1497 (2)0.37577 (11)?0.01271 (17)0.0185 (5)C231.2352 (3)0.33979 (11)?0.05514 (19)0.0235 (5)H23A1.26880.3009?0.02300.028*C241.2707 (3)0.36094 (12)?0.1441 (2)0.0261 (5)H24A1.32680.3361?0.17220.031*C251.2229 (2)0.41924 (11)?0.19194 (18)0.0204 (5)C261.1417 (3)0.45604 (12)?0.1474 (2)0.0255 (5)H26A1.11150.4956?0.17750.031*C271.1050 (3)0.43481 (11)?0.0591 (2)0.0247 (5)H27A1.05020.4600?0.03040.030*C281.2494 (3)0.44038 (12)?0.29033 (19)0.0242 (5)H1N51.148 (3)0.3133 (14)0.098 (2)0.033 (8)* Open up in another home window Atomic displacement variables (?2) em U /em 11 em U /em 22 em U /em 33 em U /em 12 em U /em 13 em U /em 23Cl10.0278 (3)0.0295 (4)0.0347 (3)0.0067 (3)0.0129 (3)?0.0071 (3)F10.0281 (8)0.0372 (9)0.0311 (8)?0.0038 (7)0.0170 (6)0.0075 (7)N10.0167 (9)0.0172 (10)0.0156 (9)0.0006 (8)0.0074 (7)0.0003 (8)N20.0161 (9)0.0184 (10)0.0156 (9)?0.0001 (8)0.0069 (7)?0.0017 (8)N30.0154 (9)0.0217 (10)0.0151 (9)0.0004 (8)0.0056 (7)0.0006 (8)N40.0192 (10)0.0268 (11)0.0163 (9)0.0060 (8)0.0081 (7)0.0040 (8)N50.0244 (11)0.0174 (11)0.0190 (9)0.0042 (9)0.0110 (8)0.0024 (8)N60.0404 (13)0.0391 (14)0.0255 (11)?0.0110 (11)0.0175 (10)?0.0008 (10)O10.0193 (8)0.0207 (9)0.0175 (8)0.0024 (7)0.0063 (6)0.0022 (7)O20.0264 (9)0.0278 (10)0.0190 (8)0.0088 (7)0.0111 (7)0.0068 (7)C10.0176 (11)0.0217 (13)0.0187 (11)0.0025 (9)0.0055 (9)0.0024 (9)C20.0236 (12)0.0258 (14)0.0167 (11)0.0039 (10)0.0076 (9)0.0062 (10)C30.0255 (13)0.0209 (13)0.0237 (11)?0.0025 (10)0.0153 (10)0.0007 (10)C40.0152 (11)0.0278 (14)0.0241 (12)?0.0018 (10)0.0058 (9)?0.0017 (10)C50.0214 (12)0.0241 (13)0.0148 (10)0.0016 (10)0.0060 (9)0.0011 (10)C60.0191 (11)0.0147 (11)0.0176 (10)0.0008 (9)0.0096 (9)?0.0004 (9)C70.0233 (12)0.0220 (13)0.0165 (10)0.0017 (10)0.0062 (9)?0.0002 (10)C80.0253 (12)0.0255 (13)0.0190 (11)?0.0005 (10)0.0102 (9)?0.0040 (10)C90.0162 (11)0.0194 (12)0.0279 (12)?0.0015 (9)0.0076 (9)?0.0064 (10)C100.0188 (12)0.0188 (13)0.0262 (12)0.0011 (10)0.0063 (9)0.0028 (10)C110.0179 (11)0.0211 (13)0.0189 (10)?0.0033 (9)0.0064 (8)?0.0005 (9)C120.0167 (11)0.0170 (12)0.0198 (10)?0.0033 (9)0.0073 (8)?0.0043 (9)C130.0172 (11)0.0173 (12)0.0131 (10)?0.0010 (9)0.0030 (8)?0.0008 (9)C140.0192 (11)0.0181 (12)0.0163 (10)?0.0030 (9)0.0076 (9)?0.0009 (9)C150.0167 (11)0.0185 (12)0.0124 (10)?0.0027 (9)0.0038 (8)?0.0016 (9)C160.0160 (11)0.0164 (12)0.0139 (10)?0.0046 (9)0.0045 (8)?0.0041 (9)C170.0164 (11)0.0245 (13)0.0170 (10)?0.0016 (9)0.0066 (9)0.0003 (10)C180.0201 (12)0.0274 (13)0.0154 (10)0.0049 (10)0.0083 (9)0.0025 (10)C190.0177 (11)0.0265 (13)0.0165 (10)0.0026 (10)0.0064 (9)0.0027 (10)C200.0192 (11)0.0226 (13)0.0176 (10)0.0035 (10)0.0080 (9)0.0020 (9)C210.0185.