#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200175.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_2200175 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-phenyl-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 o157 _journal_page_last o159 _journal_paper_doi 10.1107/S1600536801001477 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C19 H21 N3 O' _chemical_formula_sum 'C19 H21 N3 O' _chemical_formula_weight 307.39 _chemical_melting_point 502 _chemical_name_systematic ; 3,7,7-Trimethyl-4-phenyl-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 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.00 _cell_angle_beta 96.0340(14) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.0870(5) _cell_length_b 14.1978(5) _cell_length_c 11.1928(8) _cell_measurement_reflns_used 6601 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 1594.08(15) _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 .988 _diffrn_measured_fraction_theta_max .988 _diffrn_measurement_device_type Kappa-CCD _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 .047 _diffrn_reflns_av_sigmaI/netI .110 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 23946 _diffrn_reflns_theta_full 27.63 _diffrn_reflns_theta_max 27.63 _diffrn_reflns_theta_min 2.96 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .081 _exptl_absorpt_correction_T_max .994 _exptl_absorpt_correction_T_min .987 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 656 _exptl_crystal_size_max .16 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .08 _refine_diff_density_max .264 _refine_diff_density_min -.356 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .941 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3681 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .941 _refine_ls_R_factor_all .132 _refine_ls_R_factor_gt .056 _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^)+(0.0733P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .148 _reflns_number_gt 1960 _reflns_number_total 3681 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na6038.cif _cod_data_source_block 1 _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_sg_symbol_H-M 'P 21/n' _cod_database_code 2200175 _cod_database_fobs_code 2200175 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x+1/2, -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 .03979(17) .48816(12) .66069(15) .0288(4) Uani d . 1 . . N N2 .08492(17) .49441(12) .77984(15) .0301(4) Uani d . 1 . . N C3 .1736(2) .42667(14) .81730(18) .0272(5) Uani d . 1 . . C C3A .18685(19) .37042(14) .71874(17) .0248(5) Uani d . 1 . . C C31 .2363(2) .42237(16) .94324(18) .0372(6) Uani d . 1 . . C C4 .26485(19) .28267(13) .69798(17) .0253(5) Uani d . 1 . . C C41 .1994(2) .19599(14) .74721(17) .0253(5) Uani d . 1 . . C C42 .0970(2) .14951(14) .6799(2) .0309(5) Uani d . 1 . . C C43 .0345(2) .07262(15) .7259(2) .0365(6) Uani d . 1 . . C C44 .0739(2) .04152(16) .8410(2) .0405(6) Uani d . 1 . . C C45 .1757(2) .08656(15) .9089(2) .0388(6) Uani d . 1 . . C C46 .2388(2) .16331(14) .86258(19) .0319(5) Uani d . 1 . . C C4A .27697(19) .27521(14) .56348(18) .0248(5) Uani d . 1 . . C C5 .37729(19) .21344(14) .52547(18) .0249(5) Uani d . 1 . . C O51 .45326(13) .16825(10) .59917(12) .0309(4) Uani d . 1 . . O C6 .39161(19) .20477(15) .39318(18) .0294(5) Uani d . 1 . . C C7 .2616(2) .21729(14) .31167(17) .0264(5) Uani d . 1 . . C C71 .2881(2) .22044(16) .17987(18) .0353(6) Uani d . 1 . . C C72 .1679(2) .13499(15) .3284(2) .0352(6) Uani d . 1 . . C C8A .19262(19) .32104(13) .47854(18) .0245(5) Uani d . 1 . . C C8 .1995(2) .31012(14) .34582(17) .0291(5) Uani d . 1 . . C N9 .09775(16) .38222(12) .50788(14) .0286(4) Uani d . 1 . . N C9A .10411(19) .41232(14) .62706(18) .0260(5) Uani d . 1 . . C H2 .0587 .5384 .8276 .036 Uiso calc R 1 . . H H31A .2159 .4802 .9854 .056 Uiso calc PR .50 . . H H31B .3330 .4160 .9437 .056 Uiso calc PR .50 . . H H31C .2012 .3680 .9838 .056 Uiso calc PR .50 . . H H31D .2842 .3626 .9565 .056 Uiso calc PR .50 . . H H31E .1671 .4268 .9982 .056 Uiso calc PR .50 . . H H31F .2989 .4748 .9581 .056 Uiso calc PR .50 . . H H4 .3564 .2895 .7410 .030 Uiso calc R 1 . . H H42 .0689 .1706 .6008 .037 Uiso calc R 1 . . H H43 -.0355 .0413 .6781 .044 Uiso calc R 1 . . H H44 .0306 -.0108 .8730 .049 Uiso calc R 1 . . H H45 .2034 .0652 .9880 .047 Uiso calc R 1 . . H H46 .3096 .1938 .9103 .038 Uiso calc R 1 . . H H6A .4289 .1419 .3779 .035 Uiso calc R 1 . . H H6B .4563 .2526 .3713 .035 Uiso calc R 1 . . H H71A .3314 .1618 .1590 .053 Uiso calc R 1 . . H H71B .3464 .2739 .1670 .053 Uiso calc R 1 . . H H71C .2035 .2276 .1291 .053 Uiso calc R 1 . . H H72A .2097 .0761 .3060 .053 Uiso calc R 1 . . H H72B .0840 .1443 .2772 .053 Uiso calc R 1 . . H H72C .1500 .1317 .4127 .053 Uiso calc R 1 . . H H8A .2522 .3628 .3173 .035 Uiso calc R 1 . . H H8B .1082 .3146 .3040 .035 Uiso calc R 1 . . H H9 .0345 .4022 .4537 .034 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 .0358(10) .0259(10) .0242(10) .0021(8) .0004(8) -.0023(8) N2 .0394(11) .0260(10) .0252(10) -.0006(8) .0045(8) -.0040(8) C3 .0309(11) .0244(11) .0259(12) -.0041(10) .0009(9) .0015(9) C3A .0258(11) .0243(11) .0239(11) -.0021(9) .0011(9) .0013(9) C31 .0477(14) .0353(13) .0277(13) -.0035(11) -.0004(11) -.0030(10) C4 .0257(11) .0263(11) .0229(11) -.0002(9) -.0019(9) .0014(9) C41 .0290(11) .0239(11) .0240(12) .0061(9) .0067(9) -.0003(9) C42 .0332(12) .0329(13) .0265(12) -.0004(10) .0033(10) .0005(10) C43 .0416(13) .0312(13) .0372(14) -.0090(11) .0067(11) -.0029(11) C44 .0548(16) .0268(12) .0421(15) -.0016(11) .0151(13) .0025(11) C45 .0560(15) .0317(13) .0297(13) .0076(12) .0092(12) .0060(11) C46 .0386(13) .0291(12) .0278(12) .0026(10) .0028(10) .0014(10) C4A .0250(11) .0250(11) .0244(11) -.0014(9) .0024(9) .0010(9) C5 .0226(10) .0236(11) .0283(12) -.0036(9) .0008(9) .0020(9) O51 .0306(8) .0309(9) .0304(9) .0041(7) -.0001(7) .0058(7) C6 .0270(11) .0337(12) .0280(12) .0025(10) .0045(9) .0015(10) C7 .0287(11) .0270(11) .0232(12) .0009(9) .0009(9) -.0014(9) C71 .0364(12) .0415(14) .0275(12) .0024(11) .0013(10) -.0027(10) C72 .0366(13) .0312(13) .0373(14) -.0014(10) .0009(10) -.0030(10) C8A .0257(11) .0203(11) .0272(12) -.0006(9) .0018(9) -.0013(9) C8 .0336(12) .0293(12) .0240(12) .0018(10) .0008(9) .0021(9) N9 .0295(10) .0314(10) .0233(10) .0057(8) -.0048(8) -.0036(8) C9A .0285(11) .0225(11) .0267(12) -.0023(9) .0023(9) -.0021(9) 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 101.9(2) yes C3 N2 N1 113.5(2) yes C3 N2 H2 123.2 no N1 N2 H2 123.2 no N2 C3 C3A 106.32(18) no N2 C3 C31 121.77(18) no C3A C3 C31 131.91(19) no C3 C3A C9A 103.99(18) no C3 C3A C4 134.35(19) no C9A C3A C4 121.65(18) 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 C31 H31D 109.5 no H31A C31 H31D 141.1 no H31B C31 H31D 56.3 no H31C C31 H31D 56.3 no C3 C31 H31E 109.5 no H31A C31 H31E 56.3 no H31B C31 H31E 141.1 no H31C C31 H31E 56.3 no H31D C31 H31E 109.5 no C3 C31 H31F 109.5 no H31A C31 H31F 56.3 no H31B C31 H31F 56.3 no H31C C31 H31F 141.1 no H31D C31 H31F 109.5 no H31E C31 H31F 109.5 no C3A C4 C41 111.04(15) no C3A C4 C4A 107.88(16) no C41 C4 C4A 112.48(16) no C3A C4 H4 108.4 no C41 C4 H4 108.4 no C4A C4 H4 108.4 no C42 C41 C46 118.1(2) no C42 C41 C4 121.03(18) no C46 C41 C4 120.82(19) no C41 C42 C43 121.2(2) no C41 C42 H42 119.4 no C43 C42 H42 119.4 no C44 C43 C42 120.0(2) no C44 C43 H43 120.0 no C42 C43 H43 120.0 no C45 C44 C43 119.6(2) no C45 C44 H44 120.2 no C43 C44 H44 120.2 no C44 C45 C46 120.3(2) no C44 C45 H45 119.8 no C46 C45 H45 119.8 no C45 C46 C41 120.8(2) no C45 C46 H46 119.6 no C41 C46 H46 119.6 no C8A C4A C5 119.29(18) no C8A C4A C4 122.85(17) no C5 C4A C4 117.78(17) no O51 C5 C4A 121.50(19) no O51 C5 C6 119.57(18) no C4A C5 C6 118.93(18) no C5 C6 C7 114.34(16) no C5 C6 H6A 108.7 no C7 C6 H6A 108.7 no C5 C6 H6B 108.7 no C7 C6 H6B 108.7 no H6A C6 H6B 107.6 no C8 C7 C72 110.80(16) no C8 C7 C71 109.57(17) no C72 C7 C71 108.32(17) no C8 C7 C6 107.48(17) no C72 C7 C6 109.96(17) no C71 C7 C6 110.71(16) 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 N9 C8A C4A 122.51(18) no N9 C8A C8 114.33(17) no C4A C8A C8 123.14(18) no C8A C8 C7 113.56(17) no C8A C8 H8A 108.9 no C7 C8 H8A 108.9 no C8A C8 H8B 108.9 no C7 C8 H8B 108.9 no H8A C8 H8B 107.7 no C8A N9 C9A 117.66(17) no C8A N9 H9 121.2 no C9A N9 H9 121.2 no N1 C9A C3A 114.26(18) no N1 C9A N9 122.9(2) yes C3A C9A N9 122.65(18) no 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 . 1.332(2) yes N1 N2 . 1.366(2) yes N2 C3 . 1.350(3) yes N2 H2 . .8800 no C3 C3A . 1.380(3) no C3 C31 . 1.484(3) no C3A C9A . 1.387(3) no C3A C4 . 1.505(3) no C31 H31A . .9800 no C31 H31B . .9800 no C31 H31C . .9800 no C31 H31D . .9800 no C31 H31E . .9800 no C31 H31F . .9800 no C4 C41 . 1.526(3) no C4 C4A . 1.527(3) no C4 H4 . 1.0000 no C41 C42 . 1.381(3) no C41 C46 . 1.390(3) no C42 C43 . 1.386(3) no C42 H42 . .9500 no C43 C44 . 1.381(3) no C43 H43 . .9500 no C44 C45 . 1.370(3) no C44 H44 . .9500 no C45 C46 . 1.389(3) no C45 H45 . .9500 no C46 H46 . .9500 no C4A C8A . 1.371(3) no C4A C5 . 1.437(3) no C5 O51 . 1.244(2) no C5 C6 . 1.508(3) no C6 C7 . 1.527(3) no C6 H6A . .9900 no C6 H6B . .9900 no C7 C8 . 1.525(3) no C7 C72 . 1.526(3) no C7 C71 . 1.527(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 C8A N9 . 1.358(2) yes C8A C8 . 1.502(3) no C8 H8A . .9900 no C8 H8B . .9900 no N9 C9A . 1.396(2) yes N9 H9 . .8800 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 2.03 2.861(2) 158 y N9 H9 N1 3_566 .88 2.10 2.885(2) 148 y