data_2012327 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1356 _journal_page_last 1358 _publ_section_title ; 4-(4-Chlorophenyl)-3,7,7-trimethyl-1-[2-(4-nitrobenzoyl)ethyl]-4,7,8,9- tetrahydro-1H-pyrazolo[3,4-b]quinolin-5(6H)-one-ethanol (1/1) ; loop_ _publ_author_name 'Low, John Nicolson' 'Cobo, Justo' 'Nogueras, Manuel' "S\'anchez, Adolfo" 'Quiroga, Jairo' "Mej\'ia, Diana" _chemical_formula_moiety 'C28 H27 Cl N4 O4 , C2 H6 O' _chemical_formula_sum 'C30 H33 Cl N4 O5' _chemical_formula_iupac 'C28 H27 Cl N4 O4 , C2 H6 O' _chemical_formula_weight 565.05 _chemical_melting_point 466 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 23.6298(6) _cell_length_b 9.6215(3) _cell_length_c 14.2657(4) _cell_angle_alpha 90 _cell_angle_beta 120.2930(16) _cell_angle_gamma 90 _cell_volume 2800.51(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(10) _exptl_crystal_density_diffrn 1.34 _diffrn_ambient_temperature 150.0(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 .89438(9) .20346(19) .84225(14) .0202(4) Uani d . 1 . . N C11 .89995(12) .1996(2) .94874(18) .0216(5) Uani d . 1 . . C C12 .85271(12) .3010(2) .95531(18) .0228(5) Uani d . 1 . . C C13 .85921(11) .3050(2) 1.06560(17) .0206(5) Uani d . 1 . . C O133 .89835(8) .23116(17) 1.13971(13) .0274(4) Uani d . 1 . . O C131 .81675(12) .4049(2) 1.08372(18) .0217(5) Uani d . 1 . . C C132 .82133(13) .4052(2) 1.18466(19) .0263(6) Uani d . 1 . . C C133 .78476(13) .4981(3) 1.20700(18) .0281(6) Uani d . 1 . . C C134 .74471(12) .5915(2) 1.12706(19) .0240(5) Uani d . 1 . . C N13 .70767(10) .6933(2) 1.15138(17) .0305(5) Uani d . 1 . . N O11 .68257(9) .79102(19) 1.08941(16) .0369(4) Uani d . 1 . . O O12 .70387(9) .6748(2) 1.23412(14) .0409(5) Uani d . 1 . . O C135 .73805(13) .5915(3) 1.0259(2) .0274(6) Uani d . 1 . . C C136 .77391(12) .4964(3) 1.00400(18) .0257(5) Uani d . 1 . . C N2 .85070(9) .1171(2) .76075(15) .0206(4) Uani d . 1 . . N C3 .85750(11) .1469(2) .67517(17) .0199(5) Uani d . 1 . . C C31 .81786(12) .0718(3) .57003(18) .0254(5) Uani d . 1 . . C C3a .90445(11) .2518(2) .69987(16) .0180(5) Uani d . 1 . . C C4 .93151(11) .3198(2) .63608(17) .0178(5) Uani d . 1 . . C C41 .96523(11) .2159(2) .59909(17) .0165(4) Uani d . 1 . . C C42 1.01761(12) .1363(2) .67326(18) .0209(5) Uani d . 1 . . C C43 1.04852(12) .0425(2) .63972(18) .0217(5) Uani d . 1 . . C C44 1.02560(11) .0292(2) .52926(18) .0198(5) Uani d . 1 . . C Cl4 1.06286(3) -.09124(6) .48634(4) .02874(15) Uani d . 1 . . Cl C45 .97350(12) .1061(2) .45389(17) .0214(5) Uani d . 1 . . C C46 .94360(12) .1994(2) .48954(18) .0207(5) Uani d . 1 . . C C4a .97781(11) .4366(2) .70570(17) .0178(5) Uani d . 1 . . C C5 1.00230(11) .5276(2) .65364(17) .0181(5) Uani d . 1 . . C O5 .98308(8) .51332(16) .55532(11) .0239(4) Uani d . 1 . . O C6 1.04798(12) .6457(2) .71622(18) .0230(5) Uani d . 1 . . C C7 1.08601(12) .6270(2) .83932(18) .0230(5) Uani d . 1 . . C C71 1.11769(14) .7664(3) .8925(2) .0301(6) Uani d . 1 . . C C72 1.13858(13) .5163(3) .8729(2) .0332(6) Uani d . 1 . . C C8 1.03685(12) .5848(2) .87447(18) .0232(5) Uani d . 1 . . C C8a .99454(11) .4638(2) .81104(16) .0184(5) Uani d . 1 . . C N9 .97083(10) .38750(18) .86433(14) .0196(4) Uani d . 1 . . N C9a .92577(11) .2843(2) .80607(17) .0182(5) Uani d . 1 . . C O1A .79130(9) -.12932(19) .79244(14) .0376(5) Uani d . 1 . . O C1A .72545(15) -.1122(3) .7110(2) .0455(8) Uani d . 1 . . C C2A .68370(15) -.2230(3) .7226(3) .0437(7) Uani d . 1 . . C H11A .9454 .2233 1.0051 .026 Uiso calc R 1 . . H H11B .8906 .1043 .9634 .026 Uiso calc R 1 . . H H12A .8607 .3953 .9367 .027 Uiso calc R 1 . . H H12B .8073 .2744 .9009 .027 Uiso calc R 1 . . H H132 .8497 .3414 1.2389 .032 Uiso calc R 1 . . H H133 .7871 .4975 1.2755 .034 Uiso calc R 1 . . H H135 .7095 .6554 .9719 .033 Uiso calc R 1 . . H H136 .7692 .4936 .9338 .031 Uiso calc R 1 . . H H31A .7891 .0043 .5771 .038 Uiso calc R 1 . . H H31B .8472 .0230 .5513 .038 Uiso calc R 1 . . H H31C .7912 .1387 .5127 .038 Uiso calc R 1 . . H H4 .8942 .3627 .5699 .021 Uiso calc R 1 . . H H42 1.0327 .1461 .7485 .025 Uiso calc R 1 . . H H43 1.0846 -.0114 .6912 .026 Uiso calc R 1 . . H H45 .9581 .0956 .3786 .026 Uiso calc R 1 . . H H46 .9076 .2531 .4378 .025 Uiso calc R 1 . . H H6A 1.0220 .7324 .6989 .028 Uiso calc R 1 . . H H6B 1.0798 .6575 .6909 .028 Uiso calc R 1 . . H H71A 1.1422 .7555 .9716 .045 Uiso calc R 1 . . H H71B 1.0835 .8367 .8722 .045 Uiso calc R 1 . . H H71C 1.1476 .7957 .8675 .045 Uiso calc R 1 . . H H72A 1.1183 .4286 .8365 .050 Uiso calc R 1 . . H H72B 1.1609 .5032 .9517 .050 Uiso calc R 1 . . H H72C 1.1705 .5457 .8521 .050 Uiso calc R 1 . . H H8A 1.0612 .5603 .9525 .028 Uiso calc R 1 . . H H8B 1.0084 .6653 .8653 .028 Uiso calc R 1 . . H H9 .9744 .4044 .9307 .024 Uiso d R 1 . . H H1A .8102 -.0369 .7797 .045 Uiso d R 1 . . H H1A1 .7214 -.1195 .6387 .055 Uiso calc R 1 . . H H1A2 .7100 -.0188 .7172 .055 Uiso calc R 1 . . H H2A1 .6376 -.2088 .6672 .066 Uiso calc PR .50 . . H H2A2 .6886 -.2167 .7949 .066 Uiso calc PR .50 . . H H2A3 .6979 -.3150 .7132 .066 Uiso calc PR .50 . . H H2A4 .7118 -.2849 .7830 .066 Uiso calc PR .50 . . H H2A5 .6608 -.2770 .6553 .066 Uiso calc PR .50 . . H H2A6 .6515 -.1787 .7370 .066 Uiso calc PR .50 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 .0246(11) .0219(10) .0182(9) -.0045(8) .0139(9) -.0033(8) C11 .0257(13) .0246(12) .0191(11) -.0013(10) .0146(11) .0000(9) C12 .0240(13) .0291(13) .0195(11) .0006(10) .0140(11) .0001(9) C13 .0197(13) .0241(12) .0211(12) -.0056(10) .0126(11) -.0036(9) O133 .0296(10) .0308(9) .0238(8) .0020(8) .0149(8) .0024(7) C131 .0233(13) .0247(12) .0218(12) -.0077(10) .0147(11) -.0053(9) C132 .0290(15) .0274(13) .0241(12) -.0022(11) .0147(12) -.0017(10) C133 .0319(15) .0352(14) .0218(12) -.0021(12) .0170(12) -.0042(10) C134 .0213(13) .0260(13) .0286(12) -.0049(10) .0154(11) -.0076(10) N13 .0225(12) .0341(13) .0372(12) -.0053(10) .0168(10) -.0134(10) O11 .0340(11) .0293(10) .0523(12) -.0025(9) .0254(10) -.0058(9) O12 .0305(11) .0662(13) .0313(10) .0037(10) .0194(9) -.0107(9) C135 .0263(14) .0317(14) .0288(13) -.0001(11) .0173(12) .0004(11) C136 .0272(14) .0339(14) .0207(12) -.0006(12) .0155(11) -.0013(10) N2 .0177(10) .0234(10) .0223(10) -.0010(8) .0111(9) -.0051(8) C3 .0195(13) .0199(11) .0220(11) .0018(9) .0117(10) -.0014(9) C31 .0226(13) .0300(13) .0217(11) -.0042(11) .0098(11) -.0060(10) C3a .0169(12) .0194(11) .0204(11) .0016(9) .0113(10) -.0003(9) C4 .0196(12) .0183(11) .0170(10) .0011(9) .0104(10) -.0013(9) C41 .0175(12) .0161(10) .0191(11) -.0040(9) .0117(10) -.0013(8) C42 .0235(13) .0242(12) .0167(11) -.0010(10) .0113(10) -.0017(9) C43 .0188(12) .0234(12) .0225(11) .0032(10) .0102(10) .0008(9) C44 .0203(13) .0195(11) .0247(12) -.0044(10) .0152(11) -.0053(9) Cl4 .0286(3) .0284(3) .0332(3) .0027(3) .0185(3) -.0073(3) C45 .0261(13) .0226(12) .0162(11) -.0037(10) .0113(11) -.0040(9) C46 .0207(13) .0226(12) .0166(10) -.0012(10) .0079(10) -.0001(9) C4a .0194(12) .0184(11) .0182(10) .0019(9) .0112(10) -.0008(8) C5 .0223(12) .0173(11) .0172(11) .0044(9) .0119(10) .0019(8) O5 .0329(10) .0232(8) .0191(8) .0009(7) .0158(8) .0015(7) C6 .0248(13) .0233(12) .0228(12) -.0051(10) .0134(11) .0003(10) C7 .0230(13) .0248(12) .0214(11) -.0054(10) .0114(11) -.0023(9) C71 .0360(15) .0330(14) .0239(12) -.0110(12) .0171(12) -.0045(10) C72 .0245(14) .0376(15) .0310(13) .0026(12) .0092(12) .0040(12) C8 .0295(14) .0225(12) .0199(11) -.0047(10) .0140(11) -.0029(9) C8a .0200(12) .0185(11) .0186(11) .0033(10) .0111(10) .0030(9) N9 .0275(11) .0215(10) .0144(9) -.0035(8) .0139(9) -.0025(7) C9a .0187(12) .0200(11) .0181(10) .0005(9) .0108(10) -.0011(9) O1A .0351(12) .0364(10) .0334(10) -.0086(9) .0113(9) .0020(8) C1A .0377(18) .0539(19) .0383(16) -.0098(14) .0143(14) .0097(13) C2A .0441(19) .0423(17) .0548(17) -.0079(14) .0324(16) -.0034(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 N2 . 1.377(3) yes N1 C9a . 1.345(3) yes N1 C11 . 1.458(3) yes N2 C3 . 1.340(3) yes C3 C3a . 1.407(3) yes C3 C31 . 1.494(3) no C3a C9a . 1.370(3) yes N13 O11 . 1.220(3) yes N13 O12 . 1.241(3) yes N13 C134 . 1.467(3) yes C11 C12 . 1.520(3) no C11 H11A . .9900 no C11 H11B . .9900 no C12 C13 . 1.502(3) no C12 H12A . .9900 no C12 H12B . .9900 no C13 O133 . 1.221(3) yes C13 C131 . 1.503(3) no C131 C132 . 1.388(3) no C131 C136 . 1.389(4) no C132 C133 . 1.387(3) no C132 H132 . .9500 no C133 C134 . 1.384(3) no C133 H133 . .9500 no C134 C135 . 1.371(3) no C135 C136 . 1.386(3) no C135 H135 . .9500 no C136 H136 . .9500 no C31 H31A . .9800 no C31 H31B . .9800 no C31 H31C . .9800 no C3a C4 . 1.500(3) no C4 C41 . 1.528(3) no C4 C4a . 1.534(3) no C4 H4 . 1.0000 no C41 C42 . 1.384(3) no C41 C46 . 1.387(3) no C42 C43 . 1.389(3) no C42 H42 . .9500 no C43 C44 . 1.390(3) no C43 H43 . .9500 no C44 C45 . 1.372(3) no C44 Cl4 . 1.743(2) no C45 C46 . 1.388(3) no C45 H45 . .9500 no C46 H46 . .9500 no C4a C8a . 1.372(3) no C4a C5 . 1.445(3) yes C5 O5 . 1.245(2) yes C5 C6 . 1.510(3) yes C6 C7 . 1.527(3) no C6 H6A . .9900 no C6 H6B . .9900 no C7 C72 . 1.519(4) no C7 C8 . 1.534(3) no C7 C71 . 1.537(3) no C71 H71A . .9800 no C71 H71B . .9800 no C71 H71C . .9800 no C72 H72A . .9800 no C72 H72B . .9800 no C72 H72C . .9800 no C8 C8a . 1.504(3) no C8 H8A . .9900 no C8 H8B . .9900 no C8a N9 . 1.364(3) no N9 C9a . 1.385(3) no N9 H9 . .9216 no O1A C1A . 1.405(4) no O1A H1A . 1.0514 no C1A C2A . 1.518(4) no C1A H1A1 . .9900 no C1A H1A2 . .9900 no C2A H2A1 . .9800 no C2A H2A2 . .9800 no C2A H2A3 . .9800 no C2A H2A4 . .9800 no C2A H2A5 . .9800 no C2A H2A6 . .9800 no