#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012228.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_2012228 loop_ _publ_author_name 'Usman, Anwar' 'Razak, Ibrahim Abdul' 'Chantrapromma, Suchada' 'Fun, Hoong-Kun' 'Sarkar, Tarun K.' 'Basak, Sankar' 'Nigam, Gur Dayal' _publ_section_title ; Methyl (SR)-10-chloro-1,2,3,4,5,6-hexahydro-6-hydroxy-8-methoxy-1-methyl-1,9-phenanthroline-6-carboxylate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1116 _journal_page_last 1117 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C16 H19 Cl N2 O4' _chemical_formula_sum 'C16 H19 Cl N2 O4' _chemical_formula_weight 338.78 _chemical_melting_point 426 _chemical_name_systematic ; Methyl (SR)-10-chloro-1,2,3,4,5,6-hexahydro-6-hydroxy-8-methoxy-1-methyl- 1,9-phenanthroline-6-carboxylate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL97 _cell_angle_alpha 100.5740(10) _cell_angle_beta 101.7510(10) _cell_angle_gamma 111.8820(10) _cell_formula_units_Z 2 _cell_length_a 9.2081(4) _cell_length_b 9.4835(4) _cell_length_c 11.1287(6) _cell_measurement_reflns_used 3323 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 1.95 _cell_volume 846.14(7) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PARST95 (Nardelli, 1995) and PLATON (Spek, 1990)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .955 _diffrn_measured_fraction_theta_max .955 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .057 _diffrn_reflns_av_sigmaI/netI .110 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6088 _diffrn_reflns_theta_full 28.24 _diffrn_reflns_theta_max 28.24 _diffrn_reflns_theta_min 1.95 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .247 _exptl_absorpt_correction_T_max .948 _exptl_absorpt_correction_T_min .895 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour 'yellowish green' _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 356 _exptl_crystal_size_max .46 _exptl_crystal_size_mid .36 _exptl_crystal_size_min .22 _refine_diff_density_max .63 _refine_diff_density_min -.62 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .939 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 3990 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all .939 _refine_ls_R_factor_all .111 _refine_ls_R_factor_gt .076 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1071P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .209 _reflns_number_gt 2299 _reflns_number_total 3990 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1492.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '426K' was changed to '426' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012228 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_type_symbol Cl1 .45819(11) .21311(9) .18714(8) .0550(3) Uani d . 1 Cl O1 .3028(2) .7970(3) .3657(2) .0503(6) Uani d . 1 O H1A .3411 .8839 .4188 .075 Uiso calc R 1 H O2 -.0171(3) .3112(3) .0170(2) .0575(6) Uani d . 1 O O3 .5669(3) .8382(2) .2006(2) .0521(6) Uani d . 1 O O4 .6409(3) 1.0135(3) .3897(2) .0564(7) Uani d . 1 O N1 .2167(3) .2805(3) .0998(2) .0391(6) Uani d . 1 N N2 .7440(3) .5413(3) .3051(3) .0481(7) Uani d . 1 N C1 .3702(4) .3479(3) .1796(3) .0362(6) Uani d . 1 C C2 .4532(3) .5035(3) .2557(3) .0323(6) Uani d . 1 C C3 .6239(3) .5831(3) .3428(3) .0361(6) Uani d . 1 C C4 .9080(5) .6318(8) .3933(5) .108(2) Uani d D 1 C H4A .9669 .5658 .3879 .130 Uiso calc R 1 H H4B .9632 .7219 .3640 .130 Uiso calc R 1 H C5 .9225(6) .6899(9) .5249(5) .149(3) Uani d D 1 C H5A 1.0357 .7648 .5682 .179 Uiso calc R 1 H H5B .9002 .6015 .5614 .179 Uiso calc R 1 H C6 .8205(4) .7653(5) .5543(4) .0600(10) Uani d D 1 C H6A .8735 .8766 .5587 .072 Uiso calc R 1 H H6B .8065 .7587 .6374 .072 Uiso calc R 1 H C7 .6541(3) .6888(3) .4544(3) .0372(7) Uani d . 1 C C8 .5202(4) .7338(4) .4785(3) .0398(7) Uani d . 1 C H8A .5668 .8331 .5459 .048 Uiso calc R 1 H H8B .4444 .6526 .5056 .048 Uiso calc R 1 H C9 .4305(3) .7510(3) .3549(3) .0362(7) Uani d . 1 C C10 .3563(3) .5894(3) .2559(3) .0315(6) Uani d . 1 C C11 .1993(4) .5246(4) .1770(3) .0401(7) Uani d . 1 C H11A .1362 .5816 .1761 .048 Uiso calc R 1 H C12 .1361(3) .3693(4) .0974(3) .0392(7) Uani d . 1 C C13 .7499(5) .5374(5) .1754(4) .0674(11) Uani d . 1 C H13A .8091 .4777 .1515 .101 Uiso calc R 1 H H13B .8043 .6437 .1708 .101 Uiso calc R 1 H H13C .6404 .4883 .1179 .101 Uiso calc R 1 H C14 .5584(4) .8815(3) .3185(3) .0375(7) Uani d . 1 C C15 .6896(6) .9556(5) .1650(4) .0739(12) Uani d . 1 C H15A .6901 .9110 .0805 .111 Uiso calc R 1 H H15B .7954 .9884 .2247 .111 Uiso calc R 1 H H15C .6650 1.0456 .1663 .111 Uiso calc R 1 H C16 -.0894(5) .1510(4) -.0618(4) .0714(12) Uani d . 1 C H16A -.1965 .1265 -.1155 .107 Uiso calc R 1 H H16B -.0984 .0810 -.0086 .107 Uiso calc R 1 H H16C -.0219 .1379 -.1142 .107 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 Cl1 .0605(6) .0455(5) .0550(5) .0324(4) .0027(4) .0000(4) O1 .0399(12) .0559(13) .0524(14) .0288(11) .0101(10) -.0046(11) O2 .0366(12) .0470(13) .0606(15) .0086(11) -.0128(11) .0016(12) O3 .0679(15) .0448(12) .0315(12) .0122(11) .0191(11) .0043(10) O4 .0703(16) .0379(12) .0477(14) .0123(12) .0257(13) -.0042(11) N1 .0363(14) .0359(13) .0331(13) .0101(11) .0022(11) .0029(11) N2 .0299(13) .0573(16) .0555(17) .0235(13) .0066(12) .0089(14) C1 .0380(16) .0395(16) .0313(15) .0188(14) .0098(13) .0060(13) C2 .0310(15) .0369(15) .0265(14) .0137(12) .0079(11) .0059(12) C3 .0298(15) .0398(16) .0372(16) .0155(13) .0062(12) .0109(13) C4 .044(2) .158(5) .109(4) .061(3) -.002(3) -.006(4) C5 .052(3) .231(8) .113(5) .076(4) -.029(3) -.041(5) C6 .0373(19) .068(2) .051(2) .0119(18) -.0048(16) .0042(18) C7 .0302(15) .0411(16) .0306(15) .0094(13) .0028(12) .0078(13) C8 .0418(17) .0426(17) .0276(15) .0138(14) .0092(13) .0037(13) C9 .0316(15) .0411(16) .0328(15) .0173(13) .0082(12) .0013(13) C10 .0270(14) .0334(14) .0286(14) .0108(12) .0065(11) .0029(11) C11 .0320(15) .0415(16) .0411(17) .0167(13) .0045(13) .0040(14) C12 .0260(15) .0419(17) .0378(16) .0066(13) .0030(12) .0086(14) C13 .060(2) .089(3) .072(3) .040(2) .040(2) .026(2) C14 .0399(16) .0383(16) .0356(16) .0211(14) .0090(13) .0066(14) C15 .098(3) .060(2) .059(2) .019(2) .047(2) .015(2) C16 .050(2) .045(2) .077(3) -.0012(18) -.016(2) .009(2) 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' Cl Cl .1484 .1585 '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 C9 O1 H1A 109.5 ? C12 O2 C16 118.4(3) ? C14 O3 C15 115.9(3) ? C12 N1 C1 116.7(2) ? C3 N2 C4 113.9(3) yes C3 N2 C13 116.8(3) ? C4 N2 C13 109.3(3) ? N1 C1 C2 126.0(3) ? N1 C1 Cl1 112.8(2) ? C2 C1 Cl1 121.1(2) ? C1 C2 C10 114.3(2) ? C1 C2 C3 127.6(3) ? C10 C2 C3 117.9(2) ? C7 C3 N2 124.0(3) yes C7 C3 C2 117.7(2) ? N2 C3 C2 118.3(2) ? C5 C4 N2 117.4(4) ? C5 C4 H4A 108.0 ? N2 C4 H4A 108.0 ? C5 C4 H4B 108.0 ? N2 C4 H4B 108.0 ? H4A C4 H4B 107.2 ? C4 C5 C6 117.8(5) ? C4 C5 H5A 107.9 ? C6 C5 H5A 107.9 ? C4 C5 H5B 107.9 ? C6 C5 H5B 107.9 ? H5A C5 H5B 107.2 ? C5 C6 C7 111.4(3) ? C5 C6 H6A 109.3 ? C7 C6 H6A 109.3 ? C5 C6 H6B 109.3 ? C7 C6 H6B 109.3 ? H6A C6 H6B 108.0 ? C3 C7 C8 119.0(3) yes C3 C7 C6 121.5(3) ? C8 C7 C6 119.5(3) ? C7 C8 C9 108.4(2) yes C7 C8 H8A 110.0 ? C9 C8 H8A 110.0 ? C7 C8 H8B 110.0 ? C9 C8 H8B 110.0 ? H8A C8 H8B 108.4 ? O1 C9 C8 114.1(2) ? O1 C9 C10 108.4(2) yes C8 C9 C10 106.8(2) yes O1 C9 C14 107.7(2) yes C8 C9 C14 106.9(2) ? C10 C9 C14 113.2(2) ? C11 C10 C2 121.0(3) ? C11 C10 C9 121.9(2) ? C2 C10 C9 116.9(2) ? C10 C11 C12 117.9(3) ? C10 C11 H11A 121.0 ? C12 C11 H11A 121.0 ? N1 C12 O2 120.1(3) ? N1 C12 C11 123.5(3) ? O2 C12 C11 116.4(3) ? N2 C13 H13A 109.5 ? N2 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? N2 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? O4 C14 O3 122.6(3) ? O4 C14 C9 122.9(3) ? O3 C14 C9 114.5(2) ? O3 C15 H15A 109.5 ? O3 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? O3 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? O2 C16 H16A 109.5 ? O2 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? O2 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C1 1.755(3) ? O1 C9 1.417(3) ? O1 H1A .8200 ? O2 C12 1.348(3) ? O2 C16 1.428(4) ? O3 C14 1.329(3) ? O3 C15 1.442(4) ? O4 C14 1.206(3) ? N1 C12 1.314(4) yes N1 C1 1.343(4) yes N2 C3 1.418(4) yes N2 C4 1.450(5) yes N2 C13 1.451(5) ? C1 C2 1.385(4) ? C2 C10 1.415(4) yes C2 C3 1.485(4) yes C3 C7 1.349(4) yes C4 C5 1.426(4) ? C4 H4A .9700 ? C4 H4B .9700 ? C5 C6 1.429(4) ? C5 H5A .9700 ? C5 H5B .9700 ? C6 C7 1.514(4) yes C6 H6A .9700 ? C6 H6B .9700 ? C7 C8 1.503(4) yes C8 C9 1.524(4) yes C8 H8A .9700 ? C8 H8B .9700 ? C9 C10 1.524(4) yes C9 C14 1.541(4) ? C10 C11 1.364(4) ? C11 C12 1.402(4) ? C11 H11A .9300 ? C13 H13A .9600 ? C13 H13B .9600 ? C13 H13C .9600 ? C15 H15A .9600 ? C15 H15B .9600 ? C15 H15C .9600 ? C16 H16A .9600 ? C16 H16B .9600 ? C16 H16C .9600 ? 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 C12 N1 C1 C2 -2.6(4) ? C12 N1 C1 Cl1 173.8(2) ? N1 C1 C2 C10 6.8(4) ? Cl1 C1 C2 C10 -169.3(2) ? N1 C1 C2 C3 -178.5(3) ? Cl1 C1 C2 C3 5.4(4) ? C4 N2 C3 C7 -4.5(5) ? C13 N2 C3 C7 -133.5(3) ? C4 N2 C3 C2 176.8(4) ? C13 N2 C3 C2 47.8(4) ? C1 C2 C3 C7 -142.8(3) ? C10 C2 C3 C7 31.6(4) yes C1 C2 C3 N2 35.9(4) yes C10 C2 C3 N2 -149.6(3) yes C3 N2 C4 C5 28.8(8) ? C13 N2 C4 C5 161.4(6) ? N2 C4 C5 C6 -46.3(10) ? C4 C5 C6 C7 35.1(9) ? N2 C3 C7 C8 174.7(3) ? C2 C3 C7 C8 -6.6(4) ? N2 C3 C7 C6 -4.0(5) ? C2 C3 C7 C6 174.7(3) ? C5 C6 C7 C3 -10.9(6) ? C5 C6 C7 C8 170.4(4) ? C3 C7 C8 C9 -40.5(4) ? C6 C7 C8 C9 138.3(3) ? C7 C8 C9 O1 -178.6(2) ? C7 C8 C9 C10 61.6(3) ? C7 C8 C9 C14 -59.7(3) ? C1 C2 C10 C11 -5.8(4) ? C3 C2 C10 C11 179.1(3) ? C1 C2 C10 C9 169.5(2) ? C3 C2 C10 C9 -5.6(4) ? O1 C9 C10 C11 12.0(4) ? C8 C9 C10 C11 135.3(3) ? C14 C9 C10 C11 -107.4(3) ? O1 C9 C10 C2 -163.3(2) ? C8 C9 C10 C2 -40.0(3) ? C14 C9 C10 C2 77.4(3) ? C2 C10 C11 C12 1.0(4) ? C9 C10 C11 C12 -174.0(3) ? C1 N1 C12 O2 178.1(3) ? C1 N1 C12 C11 -3.1(4) yes C16 O2 C12 N1 1.7(4) yes C16 O2 C12 C11 -177.2(3) ? C10 C11 C12 N1 3.8(5) ? C10 C11 C12 O2 -177.4(3) ? C15 O3 C14 O4 4.1(5) ? C15 O3 C14 C9 -177.8(3) ? O1 C9 C14 O4 67.0(3) ? C8 C9 C14 O4 -56.0(3) ? C10 C9 C14 O4 -173.2(3) yes O1 C9 C14 O3 -111.1(3) ? C8 C9 C14 O3 125.9(3) ? C10 C9 C14 O3 8.7(3) ?