#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200176.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200176 loop_ _publ_author_name 'Cannon, Debbie' 'Quesada, Antonio' 'Quiroga, Jairo' 'Mej\'ia, Diana' 'Insuasty, Braulio' 'Abonia, Rodrigo' 'Cobo, Justo' 'Nogueras, Manuel' 'S\'anchez, Adolfo' 'Low, John Nicolson' _publ_section_title 3,7,7-Trimethyl-4-(\b-naphthyl)-4,7,8,9-tetrahydro-2H-pyrazolo[3,4-b]quinolin-5(6H)-one _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o160 _journal_page_last o162 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C23 H23 N3 O' _chemical_formula_sum 'C23 H23 N3 O' _chemical_formula_weight 357.44 _chemical_melting_point 602 _chemical_name_systematic ; 3,7,7-Trimethyl-4-(\b-naphthyl)-4,7,8,9-tetrahydro-2H-pyrazolo[3,4-b]- quinolin-5(6H)-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 106.13(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.1222(18) _cell_length_b 15.281(3) _cell_length_c 14.346(3) _cell_measurement_reflns_used 4401 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.56 _cell_measurement_theta_min 1.99 _cell_volume 1921.1(7) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and PLATON (Spek, 2000)' _computing_publication_material 'SHELXL97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150.0(10) _diffrn_measured_fraction_theta_full .992 _diffrn_measured_fraction_theta_max .992 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .062 _diffrn_reflns_av_sigmaI/netI .0628 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 16205 _diffrn_reflns_theta_full 27.56 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 1.99 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .077 _exptl_absorpt_correction_T_max .989 _exptl_absorpt_correction_T_min .974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 760 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .14 _refine_diff_density_max .226 _refine_diff_density_min -.275 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 4401 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all .086 _refine_ls_R_factor_gt .051 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0763P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .137 _reflns_number_gt 2994 _reflns_number_total 4401 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na6039.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1921.0(7) _cod_database_code 2200176 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 -.08690(15) .49567(8) .87092(9) .0266(3) Uani d . 1 . . N N2 -.14671(14) .50100(8) .77261(9) .0271(3) Uani d . 1 . . N C3 -.11695(17) .43020(10) .72492(11) .0259(4) Uani d . 1 . . C C31 -.1677(2) .42393(12) .61717(11) .0358(4) Uani d . 1 . . C C3A -.03500(17) .37374(10) .79488(11) .0245(3) Uani d . 1 . . C C4 .02769(17) .28315(9) .79326(11) .0236(3) Uani d . 1 . . C C41 -.13242(18) .15730(10) .70697(11) .0275(4) Uani d . 1 . . C C42 -.09687(18) .21414(10) .78258(11) .0250(3) Uani d . 1 . . C C43 -.17867(19) .20933(11) .85316(12) .0310(4) Uani d . 1 . . C C44 -.2933(2) .15026(11) .84482(12) .0338(4) Uani d . 1 . . C C45 -.45556(19) .03165(11) .75382(13) .0362(4) Uani d . 1 . . C C46 -.4903(2) -.02461(11) .67764(13) .0407(5) Uani d . 1 . . C C47 -.4042(2) -.02429(12) .61067(14) .0429(5) Uani d . 1 . . C C48 -.2890(2) .03424(11) .61845(13) .0368(4) Uani d . 1 . . C C48A -.25077(17) .09393(10) .69594(11) .0273(4) Uani d . 1 . . C C44A -.33384(18) .09171(10) .76635(11) .0300(4) Uani d . 1 . . C C4A .15391(17) .27030(9) .88723(10) .0233(3) Uani d . 1 . . C C5 .26617(17) .20408(9) .88870(11) .0240(3) Uani d . 1 . . C O51 .26432(13) .15970(7) .81623(8) .0308(3) Uani d . 1 . . O C6 .39283(18) .19092(10) .98122(11) .0274(4) Uani d . 1 . . C C7 .34492(17) .20762(9) 1.07350(11) .0253(4) Uani d . 1 . . C C71 .48401(19) .20359(11) 1.16209(12) .0330(4) Uani d . 1 . . C C72 .22789(19) .13925(10) 1.08329(12) .0316(4) Uani d . 1 . . C C8 .27666(18) .29944(10) 1.06552(11) .0264(4) Uani d . 1 . . C C8A .16174(17) .31720(9) .96983(11) .0236(3) Uani d . 1 . . C N9 .06635(15) .38529(8) .97054(9) .0262(3) Uani d . 1 . . N C9A -.01999(17) .41768(10) .88167(10) .0240(3) Uani d . 1 . . C H2 -.1995 .5462 .7433 .033 Uiso calc R 1 . . H H31A -.2657 .4541 .5925 .054 Uiso calc R 1 . . H H31B -.1795 .3622 .5979 .054 Uiso calc R 1 . . H H31C -.0914 .4513 .5901 .054 Uiso calc R 1 . . H H4 .0724 .2782 .7372 .028 Uiso calc R 1 . . H H41 -.0768 .1598 .6600 .033 Uiso calc R 1 . . H H43 -.1531 .2479 .9072 .037 Uiso calc R 1 . . H H44 -.3468 .1486 .8929 .041 Uiso calc R 1 . . H H45 -.5139 .0307 .7993 .043 Uiso calc R 1 . . H H46 -.5730 -.0643 .6698 .049 Uiso calc R 1 . . H H47 -.4265 -.0655 .5591 .051 Uiso calc R 1 . . H H48 -.2340 .0348 .5711 .044 Uiso calc R 1 . . H H6A .4783 .2306 .9806 .033 Uiso calc R 1 . . H H6B .4309 .1301 .9827 .033 Uiso calc R 1 . . H H71A .4522 .2144 1.2209 .049 Uiso calc R 1 . . H H71B .5581 .2482 1.1562 .049 Uiso calc R 1 . . H H71C .5311 .1456 1.1660 .049 Uiso calc R 1 . . H H72A .1977 .1504 1.1427 .047 Uiso calc R 1 . . H H72B .2730 .0807 1.0865 .047 Uiso calc R 1 . . H H72C .1379 .1428 1.0270 .047 Uiso calc R 1 . . H H8A .2270 .3077 1.1181 .032 Uiso calc R 1 . . H H8B .3602 .3428 1.0753 .032 Uiso calc R 1 . . H H9 .0594 .4082 1.0255 .031 Uiso calc R 1 . . 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 .0290(7) .0236(7) .0251(7) .0037(6) .0042(6) .0018(6) N2 .0272(7) .0246(7) .0268(7) .0048(6) .0030(6) .0038(6) C3 .0245(8) .0269(8) .0265(8) -.0006(7) .0070(7) .0026(7) C31 .0367(10) .0407(10) .0266(8) .0049(8) .0033(7) .0026(8) C3A .0241(8) .0238(8) .0251(8) .0002(6) .0063(6) .0001(7) C4 .0263(8) .0236(8) .0211(7) .0001(6) .0071(6) -.0024(6) C41 .0247(9) .0287(8) .0283(8) .0041(7) .0060(7) -.0029(7) C42 .0252(8) .0216(8) .0250(7) .0043(6) .0018(6) -.0002(6) C43 .0341(10) .0308(8) .0272(8) -.0019(7) .0068(7) -.0029(7) C44 .0347(10) .0373(9) .0311(9) .0001(8) .0119(7) .0027(8) C45 .0282(10) .0323(9) .0448(10) -.0007(7) .0046(8) .0083(8) C46 .0312(10) .0282(9) .0536(11) -.0042(8) -.0033(9) .0058(9) C47 .0374(11) .0304(9) .0509(11) .0000(8) -.0044(9) -.0091(9) C48 .0324(10) .0334(9) .0409(10) .0030(8) .0038(8) -.0090(8) C48A .0228(8) .0229(8) .0320(8) .0048(6) .0007(7) -.0011(7) C44A .0266(9) .0251(8) .0335(9) .0053(7) .0006(7) .0049(7) C4A .0245(8) .0201(7) .0252(8) -.0017(6) .0067(6) -.0008(7) C5 .0250(8) .0201(7) .0285(8) -.0043(6) .0100(7) -.0024(7) O51 .0326(7) .0265(6) .0344(6) -.0002(5) .0112(5) -.0097(5) C6 .0234(9) .0242(8) .0345(9) .0006(6) .0077(7) -.0016(7) C7 .0244(9) .0221(8) .0281(8) .0016(6) .0050(7) .0003(7) C71 .0312(10) .0309(9) .0331(9) .0023(7) .0027(7) .0012(8) C72 .0321(9) .0271(8) .0352(9) -.0003(7) .0086(7) .0027(7) C8 .0301(9) .0225(8) .0244(8) .0014(6) .0042(7) -.0017(7) C8A .0270(9) .0184(7) .0253(8) -.0011(6) .0070(7) .0001(6) N9 .0340(8) .0228(6) .0211(6) .0068(6) .0066(6) -.0006(5) C9A .0261(8) .0207(7) .0248(8) .0010(6) .0063(6) .0010(7) 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 C9A . 1.328(2) yes N1 N2 . 1.366(2) yes N2 C3 . 1.347(2) yes N2 H2 . .8800 no C3 C3A . 1.376(2) no C3 C31 . 1.488(2) no C31 H31A . .9800 no C31 H31B . .9800 no C31 H31C . .9800 no C3A C9A . 1.387(2) no C3A C4 . 1.500(2) no C4 C4A . 1.523(2) no C4 C42 . 1.526(2) no C4 H4 . 1.0000 no C41 C42 . 1.357(2) no C41 C48A . 1.426(2) no C41 H41 . .9500 no C42 C43 . 1.417(2) no C43 C44 . 1.361(2) no C43 H43 . .9500 no C44 C44A . 1.405(2) no C44 H44 . .9500 no C45 C46 . 1.357(2) no C45 C44A . 1.413(2) no C45 H45 . .9500 no C46 C47 . 1.400(3) no C46 H46 . .9500 no C47 C48 . 1.361(2) no C47 H47 . .9500 no C48 C48A . 1.405(2) no C48 H48 . .9500 no C48A C44A . 1.422(2) no C4A C8A . 1.370(2) no C4A C5 . 1.436(2) no C5 O51 . 1.2374(18) no C5 C6 . 1.512(2) no C6 C7 . 1.526(2) no C6 H6A . .9900 no C6 H6B . .9900 no C7 C8 . 1.526(2) no C7 C71 . 1.527(2) no C7 C72 . 1.528(2) 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 . 1.502(2) no C8 H8A . .9900 no C8 H8B . .9900 no C8A N9 . 1.358(2) yes N9 C9A . 1.390(2) yes N9 H9 . .8800 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C9A N1 N2 102.25(12) yes C3 N2 N1 113.42(12) yes C3 N2 H2 123.3 no N1 N2 H2 123.3 no N2 C3 C3A 106.17(13) no N2 C3 C31 122.05(14) no C3A C3 C31 131.78(15) no C3 C31 H31A 109.5 no C3 C31 H31B 109.5 no H31A C31 H31B 109.5 no C3 C31 H31C 109.5 no H31A C31 H31C 109.5 no H31B C31 H31C 109.5 no C3 C3A C9A 104.43(13) no C3 C3A C4 134.37(14) no C9A C3A C4 121.16(13) no C3A C4 C4A 107.63(12) no C3A C4 C42 111.26(12) no C4A C4 C42 111.00(12) no C3A C4 H4 109.0 no C4A C4 H4 109.0 no C42 C4 H4 109.0 no C42 C41 C48A 121.92(15) no C42 C41 H41 119.0 no C48A C41 H41 119.0 no C41 C42 C43 118.81(15) no C41 C42 C4 121.89(14) no C43 C42 C4 119.30(13) no C44 C43 C42 121.05(15) no C44 C43 H43 119.5 no C42 C43 H43 119.5 no C43 C44 C44A 121.18(16) no C43 C44 H44 119.4 no C44A C44 H44 119.4 no C46 C45 C44A 120.88(17) no C46 C45 H45 119.6 no C44A C45 H45 119.6 no C45 C46 C47 120.05(16) no C45 C46 H46 120.0 no C47 C46 H46 120.0 no C48 C47 C46 120.92(17) no C48 C47 H47 119.5 no C46 C47 H47 119.5 no C47 C48 C48A 120.52(18) no C47 C48 H48 119.7 no C48A C48 H48 119.7 no C48 C48A C44A 118.85(15) no C48 C48A C41 122.84(16) no C44A C48A C41 118.30(14) no C44 C44A C45 122.57(16) no C44 C44A C48A 118.71(15) no C45 C44A C48A 118.71(15) no C8A C4A C5 119.39(14) no C8A C4A C4 122.90(13) no C5 C4A C4 117.69(13) no O51 C5 C4A 122.06(14) no O51 C5 C6 119.57(13) no C4A C5 C6 118.35(13) no C5 C6 C7 113.95(12) no C5 C6 H6A 108.8 no C7 C6 H6A 108.8 no C5 C6 H6B 108.8 no C7 C6 H6B 108.8 no H6A C6 H6B 107.7 no C8 C7 C6 107.33(12) no C8 C7 C71 109.07(13) no C6 C7 C71 110.06(13) no C8 C7 C72 110.77(13) no C6 C7 C72 109.95(13) no C71 C7 C72 109.63(13) no C7 C71 H71A 109.5 no C7 C71 H71B 109.5 no H71A C71 H71B 109.5 no C7 C71 H71C 109.5 no H71A C71 H71C 109.5 no H71B C71 H71C 109.5 no C7 C72 H72A 109.5 no C7 C72 H72B 109.5 no H72A C72 H72B 109.5 no C7 C72 H72C 109.5 no H72A C72 H72C 109.5 no H72B C72 H72C 109.5 no C8A C8 C7 113.64(13) no C8A C8 H8A 108.8 no C7 C8 H8A 108.8 no C8A C8 H8B 108.8 no C7 C8 H8B 108.8 no H8A C8 H8B 107.7 no N9 C8A C4A 121.87(14) no N9 C8A C8 114.67(13) no C4A C8A C8 123.45(14) no C8A N9 C9A 117.82(12) yes C8A N9 H9 121.1 no C9A N9 H9 121.1 no N1 C9A C3A 113.73(13) no N1 C9A N9 123.43(13) no C3A C9A N9 122.69(13) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 O51 2_556 .88 1.95 2.810(2) 165 y N9 H9 N1 3_567 .88 2.05 2.878(2) 155 y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C9A N1 N2 C3 -.59(17) no N1 N2 C3 C3A .99(18) no N1 N2 C3 C31 -178.09(14) no N2 C3 C3A C9A -.93(17) no C31 C3 C3A C9A 178.03(16) no N2 C3 C3A C4 176.73(16) no C31 C3 C3A C4 -4.3(3) no C3 C3A C4 C4A 159.62(17) no C9A C3A C4 C4A -23.03(19) no C3 C3A C4 C42 -78.6(2) no C9A C3A C4 C42 98.79(17) no C48A C41 C42 C43 .9(2) no C48A C41 C42 C4 -178.76(13) no C3A C4 C42 C41 120.70(15) no C4A C4 C42 C41 -119.46(16) no C3A C4 C42 C43 -58.94(18) no C4A C4 C42 C43 60.90(18) no C41 C42 C43 C44 -1.4(2) no C4 C42 C43 C44 178.23(14) no C42 C43 C44 C44A .4(3) no C44A C45 C46 C47 .6(2) no C45 C46 C47 C48 -2.6(3) no C46 C47 C48 C48A 2.1(3) no C47 C48 C48A C44A .4(2) no C47 C48 C48A C41 -179.23(15) no C42 C41 C48A C48 -179.72(15) no C42 C41 C48A C44A .6(2) no C43 C44 C44A C45 -177.80(15) no C43 C44 C44A C48A 1.1(2) no C46 C45 C44A C44 -179.24(15) no C46 C45 C44A C48A 1.8(2) no C48 C48A C44A C44 178.70(15) no C41 C48A C44A C44 -1.6(2) no C48 C48A C44A C45 -2.3(2) no C41 C48A C44A C45 177.35(14) no C3A C4 C4A C8A 23.76(19) no C42 C4 C4A C8A -98.22(16) no C3A C4 C4A C5 -158.04(13) no C42 C4 C4A C5 79.98(16) no C8A C4A C5 O51 179.87(14) no C4 C4A C5 O51 1.6(2) no C8A C4A C5 C6 -2.1(2) no C4 C4A C5 C6 179.59(12) no O51 C5 C6 C7 -148.75(14) no C4A C5 C6 C7 33.22(19) no C5 C6 C7 C8 -54.59(16) no C5 C6 C7 C71 -173.17(13) no C5 C6 C7 C72 65.96(17) no C6 C7 C8 C8A 47.89(17) no C71 C7 C8 C8A 167.10(13) no C72 C7 C8 C8A -72.15(17) no C5 C4A C8A N9 174.52(13) no C4 C4A C8A N9 -7.3(2) no C5 C4A C8A C8 -4.2(2) no C4 C4A C8A C8 173.99(13) no C7 C8 C8A N9 160.58(13) no C7 C8 C8A C4A -20.6(2) no C4A C8A N9 C9A -12.4(2) no C8 C8A N9 C9A 166.38(13) no N2 N1 C9A C3A -.06(17) no N2 N1 C9A N9 175.61(14) no C3 C3A C9A N1 .63(18) no C4 C3A C9A N1 -177.41(13) no C3 C3A C9A N9 -175.07(14) no C4 C3A C9A N9 6.9(2) no C8A N9 C9A N1 -162.52(14) no C8A N9 C9A C3A 12.8(2) no _cod_database_fobs_code 2200176