#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011616.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_2011616 loop_ _publ_author_name 'Quiroga, Jairo' 'Insuasty, Braulio' 'Abonia, Rodrigo' 'Mej\'ia, Diana' 'Cobo, Justo' 'Nogueras, Manuel' 'Sanchez, Adolfo' 'Low, John Nicolson' _publ_section_title ; 5,5-Dimethyl-3-(5-methyl-1H-pyrazol-3-ylamino)cyclohex-3-en-1-one ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1457 _journal_page_last 1459 _journal_paper_doi 10.1107/S0108270100012300 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C12 H17 N3 O' _chemical_formula_sum 'C12 H17 N3 O' _chemical_formula_weight 219.29 _chemical_name_systematic ; 5,5-dimethyl-3-(5-methyl-1H-pyrazol-3-ylamino)cyclohex-3-en-1-one ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.5130(3) _cell_length_b 9.4275(3) _cell_length_c 10.6441(3) _cell_measurement_reflns_used 1515 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.39 _cell_measurement_theta_min 3.25 _cell_volume 1255.65(6) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO _computing_molecular_graphics 'PLATON (Spek, 2000)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .997 _diffrn_measured_fraction_theta_max .997 _diffrn_measurement_device_type 'Nonius 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 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .042 _diffrn_reflns_av_sigmaI/netI .031 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 13142 _diffrn_reflns_theta_full 27.39 _diffrn_reflns_theta_max 27.39 _diffrn_reflns_theta_min 3.25 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .076 _exptl_absorpt_correction_T_max .996 _exptl_absorpt_correction_T_min .981 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 472 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .05 _refine_diff_density_max .31 _refine_diff_density_min -.34 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 148 _refine_ls_number_reflns 1515 _refine_ls_number_restraints 11 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all .057 _refine_ls_R_factor_gt .048 _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^)+(0.0676P)^2^+0.3673P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .122 _reflns_number_gt 1360 _reflns_number_total 1515 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gs1111.cif _cod_data_source_block III _cod_original_sg_symbol_H-M 'Pna 21' _cod_database_code 2011616 _cod_database_fobs_code 2011616 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' 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 1.10964(16) .6399(2) .4368(2) .0290(5) Uani d . 1 . . N C2 1.1109(2) .6181(3) .5613(2) .0301(6) Uani d . 1 . . C C21 1.2104(2) .6322(4) .6382(3) .0458(8) Uani d . 1 . . C C3 1.0084(2) .5815(3) .5951(2) .0279(5) Uani d . 1 . . C C4 .95073(18) .5843(2) .4815(2) .0240(5) Uani d . 1 . . C N5 1.01159(17) .6207(2) .3848(2) .0292(5) Uani d . 1 . . N N6 .84220(15) .5633(2) .45551(19) .0260(4) Uani d . 1 A . N C7 .77125(18) .4823(2) .5174(2) .0262(5) Uani d D 1 . . C C8 .79550(19) .4000(3) .6198(2) .0271(5) Uani d . 1 A . C C9 .7170(2) .3153(3) .6787(2) .0307(6) Uani d . 1 . . C O91 .74012(15) .2407(2) .77250(19) .0410(5) Uani d . 1 A . O C10 .6014(3) .3270(4) .6379(4) .0314(6) Uani d PD .760(5) A 1 C C11 .5903(3) .3668(4) .4991(4) .0314(6) Uani d PD .760(5) A 1 C C12 .6578(3) .5002(4) .4748(4) .0314(6) Uani d PD .760(5) A 1 C C13 .4732(4) .4009(5) .4714(5) .0482(8) Uani d PD .760(5) A 1 C C14 .6256(3) .2456(5) .4150(4) .0482(8) Uani d PD .760(5) A 1 C C10' .6147(9) .2726(14) .6074(12) .0314(6) Uani d PD .240(5) A 2 C C12' .6653(7) .4544(14) .4457(11) .0314(6) Uani d PD .240(5) A 2 C C11' .5716(10) .3953(12) .5242(12) .0314(6) Uani d PD .240(5) A 2 C C13' .4790(12) .3483(19) .4385(15) .0482(8) Uani d PD .240(5) A 2 C C14' .5378(10) .5157(14) .6122(12) .0482(8) Uani d PD .240(5) A 2 C H1 1.1665 .6642 .3932 .035 Uiso calc R 1 . . H H21A 1.2644 .6846 .5902 .069 Uiso calc R 1 . . H H21B 1.2379 .5377 .6589 .069 Uiso calc R 1 . . H H21C 1.1942 .6837 .7159 .069 Uiso calc R 1 . . H H3 .9824 .5594 .6767 .033 Uiso calc R 1 . . H H6 .8171 .6093 .3899 .031 Uiso calc R 1 . . H H8 .8664 .4000 .6516 .033 Uiso calc R 1 . . H H10A .5652 .3998 .6897 .038 Uiso calc PR .760(5) A 1 H H10B .5652 .2352 .6528 .038 Uiso calc PR .760(5) A 1 H H12A .6570 .5218 .3838 .038 Uiso calc PR .760(5) A 1 H H12B .6254 .5816 .5195 .038 Uiso calc PR .760(5) A 1 H H13A .4653 .4261 .3825 .072 Uiso calc PR .760(5) A 1 H H13B .4502 .4809 .5237 .072 Uiso calc PR .760(5) A 1 H H13C .4290 .3178 .4902 .072 Uiso calc PR .760(5) A 1 H H14A .5785 .1638 .4282 .072 Uiso calc PR .760(5) A 1 H H14B .6993 .2191 .4356 .072 Uiso calc PR .760(5) A 1 H H14C .6217 .2755 .3270 .072 Uiso calc PR .760(5) A 1 H H10C .5590 .2447 .6686 .038 Uiso calc PR .240(5) A 2 H H10D .6302 .1894 .5536 .038 Uiso calc PR .240(5) A 2 H H12C .6419 .5446 .4067 .038 Uiso calc PR .240(5) A 2 H H12D .6802 .3868 .3767 .038 Uiso calc PR .240(5) A 2 H H13D .4162 .3264 .4900 .072 Uiso calc PR .240(5) A 2 H H13E .5003 .2637 .3913 .072 Uiso calc PR .240(5) A 2 H H13F .4615 .4250 .3798 .072 Uiso calc PR .240(5) A 2 H H14D .5083 .5940 .5626 .072 Uiso calc PR .240(5) A 2 H H14E .6001 .5491 .6595 .072 Uiso calc PR .240(5) A 2 H H14F .4834 .4809 .6708 .072 Uiso calc PR .240(5) A 2 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 .0253(10) .0349(11) .0268(11) -.0070(8) .0009(8) -.0010(9) C2 .0356(14) .0276(12) .0270(13) -.0040(10) -.0045(11) .0035(10) C21 .0385(15) .0589(19) .0400(16) -.0139(13) -.0125(13) .0093(15) C3 .0312(12) .0311(12) .0213(12) -.0056(9) .0009(10) .0029(10) C4 .0282(11) .0203(10) .0233(11) -.0007(8) .0021(10) .0019(9) N5 .0293(10) .0327(10) .0256(10) -.0064(9) .0017(9) .0023(9) N6 .0268(10) .0274(10) .0237(10) .0016(7) -.0007(8) .0091(8) C7 .0270(11) .0268(11) .0247(12) -.0013(9) .0006(9) .0048(9) C8 .0253(11) .0294(11) .0267(13) -.0035(9) -.0021(10) .0069(10) C9 .0289(12) .0367(13) .0264(12) -.0071(10) -.0043(10) .0087(11) O91 .0418(10) .0488(12) .0324(10) -.0190(9) -.0115(9) .0214(9) C10 .0276(9) .0347(14) .0319(13) -.0034(9) -.0014(8) .0113(10) C11 .0276(9) .0347(14) .0319(13) -.0034(9) -.0014(8) .0113(10) C12 .0276(9) .0347(14) .0319(13) -.0034(9) -.0014(8) .0113(10) C13 .0458(14) .058(2) .0410(17) -.0188(15) -.0101(13) .0110(14) C14 .0458(14) .058(2) .0410(17) -.0188(15) -.0101(13) .0110(14) C10' .0276(9) .0347(14) .0319(13) -.0034(9) -.0014(8) .0113(10) C12' .0276(9) .0347(14) .0319(13) -.0034(9) -.0014(8) .0113(10) C11' .0276(9) .0347(14) .0319(13) -.0034(9) -.0014(8) .0113(10) C13' .0458(14) .058(2) .0410(17) -.0188(15) -.0101(13) .0110(14) C14' .0458(14) .058(2) .0410(17) -.0188(15) -.0101(13) .0110(14) 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 C2 N1 N5 113.1(2) no C2 N1 H1 123.4 no N5 N1 H1 123.4 no N1 C2 C3 106.6(2) no N1 C2 C21 122.5(3) no C3 C2 C21 130.9(3) no C2 C21 H21A 109.5 no C2 C21 H21B 109.5 no H21A C21 H21B 109.5 no C2 C21 H21C 109.5 no H21A C21 H21C 109.5 no H21B C21 H21C 109.5 no C2 C3 C4 104.4(2) no C2 C3 H3 127.8 no C4 C3 H3 127.8 no N5 C4 N6 116.1(2) no N5 C4 C3 112.1(2) no N6 C4 C3 131.6(2) no C4 N5 N1 103.7(2) no C7 N6 C4 128.6(2) no C7 N6 H6 115.7 no C4 N6 H6 115.7 no N6 C7 C8 124.4(2) no N6 C7 C12 114.4(2) no C8 C7 C12 120.9(2) no N6 C7 C12' 114.8(5) no C8 C7 C12' 118.9(5) no C12 C7 C12' 20.3(5) no C7 C8 C9 121.2(2) no C7 C8 H8 119.4 no C9 C8 H8 119.4 no O91 C9 C8 120.7(2) no O91 C9 C10 119.3(2) no C8 C9 C10 119.7(2) no O91 C9 C10' 115.9(5) no C8 C9 C10' 120.4(5) no C10 C9 C10' 23.8(5) no C9 C10 C11 112.4(3) no C9 C10 H10A 109.1 no C11 C10 H10A 109.1 no C9 C10 H10B 109.1 no C11 C10 H10B 109.1 no H10A C10 H10B 107.9 no C14 C11 C10 111.0(3) no C14 C11 C13 108.9(4) no C10 C11 C13 108.9(4) no C14 C11 C12 110.9(3) no C10 C11 C12 108.3(4) no C13 C11 C12 108.7(3) no C7 C12 C11 112.1(3) no C7 C12 H12A 109.2 no C11 C12 H12A 109.2 no C7 C12 H12B 109.2 no C11 C12 H12B 109.2 no H12A C12 H12B 107.9 no C9 C10' C11' 112.0(9) no C9 C10' H10C 109.2 no C11' C10' H10C 109.2 no C9 C10' H10D 109.2 no C11' C10' H10D 109.2 no H10C C10' H10D 107.9 no C11' C12' C7 116.3(9) no C11' C12' H12C 108.2 no C7 C12' H12C 108.2 no C11' C12' H12D 108.2 no C7 C12' H12D 108.2 no H12C C12' H12D 107.4 no C14' C11' C13' 111.6(11) no C14' C11' C12' 105.9(10) no C13' C11' C12' 110.8(11) no C14' C11' C10' 107.4(11) no C13' C11' C10' 112.6(12) no C12' C11' C10' 108.3(10) no C11' C13' H13D 109.5 no C11' C13' H13E 109.5 no H13D C13' H13E 109.5 no C11' C13' H13F 109.5 no H13D C13' H13F 109.5 no H13E C13' H13F 109.5 no C11' C14' H14D 109.5 no C11' C14' H14E 109.5 no H14D C14' H14E 109.5 no C11' C14' H14F 109.5 no H14D C14' H14F 109.5 no H14E C14' H14F 109.5 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 C2 . 1.342(3) no N1 N5 . 1.358(3) no N1 H1 . .8800 no C2 C3 . 1.376(4) no C2 C21 . 1.497(4) no C21 H21A . .9800 no C21 H21B . .9800 no C21 H21C . .9800 no C3 C4 . 1.409(4) no C3 H3 . .9500 no C4 N5 . 1.326(3) no C4 N6 . 1.400(3) yes N6 C7 . 1.343(3) yes N6 H6 . .8800 no C7 C8 . 1.372(3) yes C7 C12 . 1.500(4) no C7 C12' . 1.553(8) no C8 C9 . 1.413(3) yes C8 H8 . .9500 no C9 O91 . 1.255(3) yes C9 C10 . 1.515(4) no C9 C10' . 1.542(12) no C10 C11 . 1.530(5) no C10 H10A . .9900 no C10 H10B . .9900 no C11 C14 . 1.517(6) no C11 C13 . 1.530(6) no C11 C12 . 1.537(5) no C12 H12A . .9900 no C12 H12B . .9900 no C13 H13A . .9800 no C13 H13B . .9800 no C13 H13C . .9800 no C14 H14A . .9800 no C14 H14B . .9800 no C14 H14C . .9800 no C10' C11' . 1.554(14) no C10' H10C . .9900 no C10' H10D . .9900 no C12' C11' . 1.544(15) no C12' H12C . .9900 no C12' H12D . .9900 no C11' C14' . 1.531(15) no C11' C13' . 1.539(15) no C13' H13D . .9800 no C13' H13E . .9800 no C13' H13F . .9800 no C14' H14D . .9800 no C14' H14E . .9800 no C14' H14F . .9800 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 N1 H1 O91 2_764 .88 1.95 2.804(3) 162 y N6 H6 O91 3_654 .88 1.90 2.766(3) 168 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 N5 N1 C2 C3 .3(3) no N5 N1 C2 C21 179.6(2) no N1 C2 C3 C4 .1(3) no C21 C2 C3 C4 -179.0(3) no C2 C3 C4 N5 -.5(3) no C2 C3 C4 N6 -176.6(2) no N6 C4 N5 N1 177.40(19) no C3 C4 N5 N1 .7(3) no C2 N1 N5 C4 -.6(3) no N5 C4 N6 C7 154.4(2) no C3 C4 N6 C7 -29.7(4) no C4 N6 C7 C8 -1.7(4) no C4 N6 C7 C12 171.8(3) no C4 N6 C7 C12' -165.9(6) no N6 C7 C8 C9 -178.8(2) yes C12 C7 C8 C9 8.1(4) no C12' C7 C8 C9 -15.2(7) no C7 C8 C9 O91 -179.9(3) no C7 C8 C9 C10 -6.8(4) no C7 C8 C9 C10' 20.7(7) no O91 C9 C10 C11 -156.5(3) no C8 C9 C10 C11 30.3(5) no C10' C9 C10 C11 -68.3(12) no C9 C10 C11 C14 69.7(4) no C9 C10 C11 C13 -170.5(3) no C9 C10 C11 C12 -52.4(5) no N6 C7 C12 C11 153.5(3) no C8 C7 C12 C11 -32.7(5) no C12' C7 C12 C11 57.8(13) no C14 C11 C12 C7 -68.6(4) no C10 C11 C12 C7 53.5(5) no C13 C11 C12 C7 171.7(3) no O91 C9 C10' C11' 160.7(8) no C8 C9 C10' C11' -38.9(12) no C10 C9 C10' C11' 56.4(10) no N6 C7 C12' C11' -165.1(8) no C8 C7 C12' C11' 29.8(13) no C12 C7 C12' C11' -71.5(15) no C7 C12' C11' C14' 68.8(13) no C7 C12' C11' C13' -170.1(10) no C7 C12' C11' C10' -46.1(15) no C9 C10' C11' C14' -64.7(12) no C9 C10' C11' C13' 172.1(10) no C9 C10' C11' C12' 49.2(14) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 3164613