#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/64/2006441.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_2006441 loop_ _publ_author_name A.Thiruvalluvar V.Parthasarathi D.Natarajan N.Bhavani 'Mohan Bhadbhade' _publ_section_title ; 3,3-Dimethyl-N-nitroso-2-phenyldecahydroquinolin-4-one ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1086 _journal_page_last 1088 _journal_paper_doi 10.1107/S0108270197004770 _journal_volume 53 _journal_year 1997 _chemical_formula_analytical none _chemical_formula_moiety 'C17 H22 N2 O2' _chemical_formula_structural none _chemical_formula_sum 'C17 H22 N2 O2' _chemical_formula_weight 286.37 _chemical_melting_point 372.5(5) _chemical_name_common trans-decahydroquinoline _chemical_name_systematic ; N-Nitroso-3,3-dimethyl-2-phenyldecahydroquinolin-4-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _cell_angle_alpha 90.00 _cell_angle_beta 110.18(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.596(2) _cell_length_b 22.882(11) _cell_length_c 9.311(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 22 _cell_measurement_theta_min 16 _cell_volume 1519.0(9) _computing_cell_refinement SDP _computing_data_collection 'SDP (Frenz, 1978)' _computing_data_reduction SDP _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 298 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2575 _diffrn_reflns_theta_max 65 _diffrn_reflns_theta_min 3.86 _diffrn_standards_decay_% negligible _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.657 _exptl_absorpt_correction_type 'not applied' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'plate like' _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.222 _refine_diff_density_min -0.242 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.076 _refine_ls_goodness_of_fit_obs 1.148 _refine_ls_hydrogen_treatment 'H-atom parameters not refined' _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2563 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_restrained_S_obs 1.148 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_obs .0587 _refine_ls_shift/esd_max -0.006 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0933P)^2^+0.4749P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1681 _refine_ls_wR_factor_obs .1588 _reflns_number_observed 2042 _reflns_number_total 2563 _reflns_observed_criterion I>2\s(I) _cod_data_source_file vj1058.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '372--373' was changed to '372.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '372--373' was changed to '372.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0933P)^2^+0.4749P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0933P)^2^+0.4749P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2006441 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' 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 O4 .0858(14) .0522(11) .0604(11) -.0074(9) .0268(10) -.0197(9) O11 .0685(12) .0556(11) .0473(10) .0061(8) .0165(8) -.0132(8) N1 .0386(9) .0344(9) .0415(10) .0006(7) .0136(7) -.0024(7) C2 .0402(12) .0383(11) .0396(11) -.0007(9) .0196(9) -.0034(9) C3 .0341(11) .0403(12) .0455(12) -.0020(9) .0128(9) -.0020(9) C4 .0409(12) .0417(12) .0387(12) .0022(9) .0086(9) -.0049(9) C5 .078(2) .083(2) .0431(14) -.012(2) .0269(13) -.0057(13) C6 .075(2) .109(3) .052(2) -.014(2) .0313(15) .008(2) C7 .064(2) .084(2) .061(2) -.017(2) .0162(14) .025(2) C8 .059(2) .054(2) .061(2) -.0122(12) .0196(12) .0077(12) C9 .0374(11) .0441(12) .0401(12) -.0006(9) .0106(9) .0037(9) C10 .0368(12) .0522(13) .0379(11) .0008(9) .0106(9) -.0020(9) N11 .0467(11) .0386(10) .0512(12) .0042(8) .0085(9) -.0067(8) C21 .0460(12) .0354(11) .0342(11) -.0016(9) .0126(9) -.0047(8) C22 .0415(12) .0474(13) .0422(12) .0003(10) .0119(9) .0000(9) C23 .0476(14) .063(2) .0549(15) .0062(12) .0093(11) -.0044(12) C24 .065(2) .051(2) .0516(15) .0086(13) -.0031(12) -.0035(11) C25 .090(2) .057(2) .0417(14) -.0082(15) .0080(13) .0097(12) C26 .063(2) .061(2) .0420(13) -.0084(12) .0169(11) .0055(11) C31 .0514(14) .0479(13) .0563(14) -.0105(11) .0173(11) .0003(11) C32 .0342(12) .0591(15) .068(2) -.0021(10) .0143(11) -.0052(12) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O4 .0707(3) .78789(8) -.2969(2) .0657(5) Uani d . 1 . O O11 .2075(3) .97853(8) .1825(2) .0580(5) Uani d . 1 . O N1 .1806(2) .93462(7) -.0291(2) .0382(4) Uani d . 1 . N C2 .1523(3) .87917(9) .0405(2) .0378(5) Uani d . 1 . C C3 .0313(3) .83693(9) -.0840(2) .0402(5) Uani d . 1 . C C4 .1051(3) .83082(9) -.2166(2) .0418(5) Uani d . 1 . C C5 .2072(4) .88474(14) -.4118(3) .0665(8) Uani d . 1 . C C6 .3345(4) .9325(2) -.4326(3) .0763(9) Uani d . 1 . C C7 .2916(4) .99036(15) -.3759(3) .0713(9) Uani d . 1 . C C8 .2972(4) .98748(12) -.2113(3) .0584(7) Uani d . 1 . C C9 .1697(3) .93965(9) -.1900(2) .0412(5) Uani d . 1 . C C10 .2176(3) .88088(10) -.2455(2) .0429(5) Uani d . 1 . C N11 .2048(3) .98380(8) .0493(2) .0477(5) Uani d . 1 . N C21 .3376(3) .85644(9) .1523(2) .0388(5) Uani d . 1 . C C22 .5099(3) .86901(10) .1391(3) .0444(5) Uani d . 1 . C C23 .6748(3) .84968(12) .2465(3) .0574(7) Uani d . 1 . C C24 .6731(4) .81725(11) .3703(3) .0622(7) Uani d . 1 . C C25 .5028(5) .80457(12) .3842(3) .0668(8) Uani d . 1 . C C26 .3389(4) .82364(11) .2780(3) .0555(6) Uani d . 1 . C C31 .0187(3) .77669(11) -.0182(3) .0522(6) Uani d . 1 . C C32 -.1699(3) .86159(12) -.1533(3) .0548(6) Uani d . 1 . C H2 .0824 .8880 .1052 .043 Uiso d . 1 . H H5A .0810 .8916 -.4749 .080 Uiso d . 1 . H H5B .2361 .8468 -.4398 .080 Uiso d . 1 . H H6A .3236 .9340 -.5375 .091 Uiso d . 1 . H H6B .4628 .9233 -.3794 .091 Uiso d . 1 . H H7A .1719 1.0038 -.4392 .086 Uiso d . 1 . H H7B .3725 1.0206 -.3855 .086 Uiso d . 1 . H H8A .4231 .9788 -.1494 .067 Uiso d . 1 . H H8B .2628 1.0242 -.1811 .067 Uiso d . 1 . H H9 .0417 .9478 -.2468 .047 Uiso d . 1 . H H10 .3434 .8728 -.1827 .048 Uiso d . 1 . H H22 .5121 .8920 .0546 .048 Uiso d . 1 . H H23 .7902 .8606 .2358 .060 Uiso d . 1 . H H24 .7847 .8054 .4490 .064 Uiso d . 1 . H H25 .4939 .7828 .4682 .067 Uiso d . 1 . H H26 .2194 .8162 .2856 .062 Uiso d . 1 . H H31A .1393 .7593 .0242 .060 Uiso d . 1 . H H31B -.0246 .7786 .0658 .060 Uiso d . 1 . H H31C -.0626 .7546 -.1008 .060 Uiso d . 1 . H H32A -.2449 .8377 -.2354 .062 Uiso d . 1 . H H32B -.1736 .9002 -.1924 .062 Uiso d . 1 . H H32C -.2137 .8646 -.0696 .062 Uiso d . 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 N11 N1 C2 120.3(2) no N11 N1 C9 116.3(2) no C2 N1 C9 123.2(2) no N1 C2 C21 110.7(2) yes N1 C2 C3 110.3(2) yes C21 C2 C3 118.0(2) no N1 C2 H2 107.0(2) no C21 C2 H2 103.1(2) no C3 C2 H2 106.9(2) no C31 C3 C4 109.5(2) no C31 C3 C2 111.5(2) no C4 C3 C2 112.0(2) no C31 C3 C32 107.9(2) no C4 C3 C32 106.4(2) no C2 C3 C32 109.3(2) no O4 C4 C10 121.6(2) yes O4 C4 C3 120.9(2) yes C10 C4 C3 117.6(2) no C6 C5 C10 111.1(2) no C6 C5 H5A 110.8(3) no C10 C5 H5A 109.0(2) no C6 C5 H5B 113.9(3) no C10 C5 H5B 106.8(2) no H5A C5 H5B 105.0(3) no C7 C6 C5 111.4(2) no C7 C6 H6A 112.0(3) no C5 C6 H6A 108.9(3) no C7 C6 H6B 108.6(3) no C5 C6 H6B 111.0(3) no H6A C6 H6B 104.7(3) no C6 C7 C8 112.5(2) no C6 C7 H7A 110.2(3) no C8 C7 H7A 109.2(3) no C6 C7 H7B 112.5(3) no C8 C7 H7B 109.4(3) no H7A C7 H7B 102.6(3) no C9 C8 C7 111.5(2) no C9 C8 H8A 108.9(2) no C7 C8 H8A 107.0(2) no C9 C8 H8B 110.2(2) no C7 C8 H8B 110.2(2) no H8A C8 H8B 109.0(3) no N1 C9 C8 111.9(2) yes N1 C9 C10 109.8(2) yes C8 C9 C10 110.7(2) no N1 C9 H9 105.6(2) no C8 C9 H9 111.2(2) no C10 C9 H9 107.5(2) no C4 C10 C5 113.0(2) no C4 C10 C9 113.1(2) no C5 C10 C9 110.9(2) no C4 C10 H10 104.7(2) no C5 C10 H10 108.9(2) no C9 C10 H10 105.6(2) no O11 N11 N1 115.0(2) yes C22 C21 C26 117.1(2) no C22 C21 C2 123.1(2) no C26 C21 C2 119.7(2) no C23 C22 C21 121.2(2) no C23 C22 H22 120.4(2) no C21 C22 H22 118.3(2) no C24 C23 C22 120.8(2) no C24 C23 H23 120.4(3) no C22 C23 H23 118.7(3) no C23 C24 C25 118.3(2) no C23 C24 H24 122.5(3) no C25 C24 H24 119.1(3) no C26 C25 C24 121.1(2) no C26 C25 H25 117.2(3) no C24 C25 H25 121.7(3) no C25 C26 C21 121.5(2) no C25 C26 H26 123.0(2) no C21 C26 H26 115.5(2) no C3 C31 H31A 111.1(2) no C3 C31 H31B 112.2(2) no H31A C31 H31B 103.7(2) no C3 C31 H31C 105.6(2) no H31A C31 H31C 112.2(3) no H31B C31 H31C 112.3(2) no C3 C32 H32A 110.9(2) no C3 C32 H32B 113.1(2) no H32A C32 H32B 107.2(3) no C3 C32 H32C 105.1(2) no H32A C32 H32C 114.7(2) no H32B C32 H32C 105.9(3) 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 O4 C4 . 1.207(3) yes O11 N11 . 1.239(2) yes N1 N11 . 1.319(2) no N1 C2 . 1.474(3) yes N1 C9 . 1.476(3) yes C2 C21 . 1.524(3) no C2 C3 . 1.545(3) no C2 H2 . .952(2) no C3 C31 . 1.525(3) no C3 C4 . 1.528(3) no C3 C32 . 1.546(3) no C4 C10 . 1.507(3) no C5 C6 . 1.515(4) no C5 C10 . 1.526(3) no C5 H5A . .948(3) no C5 H5B . .953(3) no C6 C7 . 1.503(5) no C6 H6A . .952(3) no C6 H6B . .952(3) no C7 C8 . 1.520(4) no C7 H7A . .948(3) no C7 H7B . .950(3) no C8 C9 . 1.519(3) no C8 H8A . .951(3) no C8 H8B . .950(3) no C9 C10 . 1.529(3) no C9 H9 . .952(2) no C10 H10 . .951(2) no C21 C22 . 1.386(3) no C21 C26 . 1.388(3) no C22 C23 . 1.379(3) no C22 H22 . .951(2) no C23 C24 . 1.375(4) no C23 H23 . .950(3) no C24 C25 . 1.375(5) no C24 H24 . .949(2) no C25 C26 . 1.367(4) no C25 H25 . .949(3) no C26 H26 . .950(3) no C31 H31A . .951(3) no C31 H31B . .948(2) no C31 H31C . .950(2) no C32 H32A . .952(3) no C32 H32B . .951(3) no C32 H32C . .950(3) no 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 N11 N1 C2 C21 -76.8(2) no C9 N1 C2 C21 107.9(2) no N11 N1 C2 C3 150.8(2) no C9 N1 C2 C3 -24.5(2) no N1 C2 C3 C31 173.3(2) no C21 C2 C3 C31 44.8(2) no N1 C2 C3 C4 50.2(2) no C21 C2 C3 C4 -78.3(2) no N1 C2 C3 C32 -67.4(2) no C21 C2 C3 C32 164.0(2) no C31 C3 C4 O4 31.8(3) no C2 C3 C4 O4 156.0(2) no C32 C3 C4 O4 -84.6(3) no C31 C3 C4 C10 -149.8(2) no C2 C3 C4 C10 -25.5(3) no C32 C3 C4 C10 93.8(2) no C10 C5 C6 C7 -55.2(3) no C5 C6 C7 C8 54.3(3) no C6 C7 C8 C9 -54.2(3) no N11 N1 C9 C8 35.0(3) no C2 N1 C9 C8 -149.6(2) no N11 N1 C9 C10 158.3(2) no C2 N1 C9 C10 -26.3(3) no C7 C8 C9 N1 177.4(2) no C7 C8 C9 C10 54.6(3) no O4 C4 C10 C5 25.1(3) no C3 C4 C10 C5 -153.3(2) no O4 C4 C10 C9 152.3(2) no C3 C4 C10 C9 -26.2(3) no C6 C5 C10 C4 -175.4(2) no C6 C5 C10 C9 56.4(3) no N1 C9 C10 C4 51.7(2) no C8 C9 C10 C4 175.8(2) no N1 C9 C10 C5 179.9(2) no C8 C9 C10 C5 -56.0(3) no C2 N1 N11 O11 2.2(3) no C9 N1 N11 O11 177.8(2) no N1 C2 C21 C22 -27.3(3) no C3 C2 C21 C22 101.1(2) no N1 C2 C21 C26 149.7(2) no C3 C2 C21 C26 -81.9(3) no C26 C21 C22 C23 0.0(3) no C2 C21 C22 C23 177.1(2) no C21 C22 C23 C24 0.0(4) no C22 C23 C24 C25 0.0(4) no C23 C24 C25 C26 0.0(4) no C24 C25 C26 C21 0.0(4) no C22 C21 C26 C25 0.0(4) no C2 C21 C26 C25 -177.2(2) no H9 C9 C10 H10 -176.6(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 21629377