#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009070.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_2009070 loop_ _publ_author_name 'Sarkar, Tarun Kumar' 'Basak, Sankar' 'Ghosh, Sunil Kumar' 'Nigam, Gur Dayal' 'Razak, Ibrahim Abdul' 'Shanmuga Sundara Raj, S.' 'Fun, Hoong-Kun' _publ_section_title ;Methyl (SR)-8,10-dichloro-1,2,3,4,5,6-hexahydro-6-hydroxy-1-methyl-1,9-phenanthroline-6-carboxylate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9900128 _journal_paper_doi 10.1107/S0108270199098650 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C15 H16 Cl2 N2 O3' _chemical_formula_weight 343.20 _chemical_name_systematic ; Methyl (SR)-8,10-dichloro-1,2,3,4,5,6-hexahydro-6-hydroxy-1-methyl- 1,9-phenanthroline-6-carboxylate ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.4700(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.99210(10) _cell_length_b 13.2646(2) _cell_length_c 12.1386(2) _cell_measurement_reflns_used 8192 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 3.05 _cell_volume 1608.81(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_publication_material 'SHELXTL (Sheldrick, 1997) and PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measurement_device 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.046 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 11246 _diffrn_reflns_theta_max 28.26 _diffrn_reflns_theta_min 3.05 _exptl_absorpt_coefficient_mu 0.417 _exptl_absorpt_correction_T_max 0.936 _exptl_absorpt_correction_T_min 0.825 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.34 _refine_diff_density_min -0.45 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 3957 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.041 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0739P)^2^+0.0297P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.121 _reflns_number_gt 3182 _reflns_number_total 3957 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0180.cif _cod_data_source_block tks5m _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2009070 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 Cl1 .43218(5) .91832(3) .30303(4) .05230(15) Uani d . 1 . . Cl Cl2 .32579(5) .57368(3) .12787(4) .05663(16) Uani d . 1 . . Cl O1 .67051(10) .73625(8) -.13595(8) .0406(3) Uani d . 1 . . O H1A .7238 .7483 -.1852 .061 Uiso calc R 1 . . H O2 .93475(10) .82297(10) -.04886(11) .0559(3) Uani d . 1 . . O O3 .84768(11) .71866(11) .07601(11) .0579(4) Uani d . 1 . . O N1 .40040(11) .74971(9) .20170(9) .0343(3) Uani d . 1 . . N N2 .70591(13) .99110(10) .22458(10) .0418(3) Uani d . 1 . . N C1 .47829(14) .83148(10) .20314(11) .0322(3) Uani d . 1 . . C C2 .42333(13) .68221(10) .12405(11) .0337(3) Uani d . 1 . . C C3 .51657(13) .69385(10) .04110(11) .0320(3) Uani d . 1 . . C H3A .5255 .6461 -.0145 .038 Uiso calc R 1 . . H C4 .59555(12) .77891(10) .04420(10) .0274(3) Uani d . 1 . . C C5 .69475(12) .80231(10) -.04583(10) .0291(3) Uani d . 1 . . C C6 .67673(14) .91276(11) -.07583(11) .0352(3) Uani d . 1 . . C H6A .7384 .9310 -.1338 .042 Uiso calc R 1 . . H H6B .5863 .9242 -.1026 .042 Uiso calc R 1 . . H C7 .70312(13) .97649(10) .02455(11) .0331(3) Uani d . 1 . . C C8 .76917(17) 1.07748(11) .00827(15) .0452(4) Uani d . 1 . . C H8A .8629 1.0678 -.0092 .054 Uiso calc R 1 . . H H8B .7268 1.1123 -.0530 .054 Uiso calc R 1 . . H C9 .75760(18) 1.14032(13) .11095(17) .0545(5) Uani d . 1 . . C H9A .8155 1.1988 .1058 .065 Uiso calc R 1 . . H H9B .6662 1.1637 .1190 .065 Uiso calc R 1 . . H C10 .79732(18) 1.07761(13) .20888(16) .0523(4) Uani d . 1 . . C H10A .8877 1.0528 .1989 .063 Uiso calc R 1 . . H H10B .7967 1.1194 .2744 .063 Uiso calc R 1 . . H C11 .67008(13) .94220(10) .12557(11) .0309(3) Uani d . 1 . . C C12 .58268(12) .85096(9) .12935(10) .0278(3) Uani d . 1 . . C C13 .84040(13) .78464(11) -.00578(12) .0345(3) Uani d . 1 . . C C14 .9817(2) .6923(2) .1138(2) .0876(8) Uani d . 1 . . C H14A .9766 .6369 .1646 .131 Uiso calc R 1 . . H H14B 1.0217 .7493 .1500 .131 Uiso calc R 1 . . H H14C 1.0352 .6732 .0519 .131 Uiso calc R 1 . . H C15 .7588(2) .92517(16) .31039(16) .0646(5) Uani d . 1 . . C H15A .7669 .9621 .3781 .097 Uiso calc R 1 . . H H15B .8452 .9006 .2891 .097 Uiso calc R 1 . . H H15C .6991 .8693 .3205 .097 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 .0679(3) .0428(2) .0467(2) .00070(17) .0326(2) -.00683(15) Cl2 .0607(3) .0600(3) .0494(3) -.03286(19) .0159(2) -.00407(18) O1 .0391(5) .0558(6) .0271(5) -.0100(4) .0114(4) -.0115(4) O2 .0290(5) .0778(8) .0609(8) -.0107(5) .0091(5) .0097(6) O3 .0343(5) .0810(9) .0585(8) .0090(5) .0034(5) .0304(7) N1 .0337(5) .0411(6) .0283(6) .0001(5) .0102(4) .0055(5) N2 .0464(7) .0454(7) .0337(6) -.0062(5) .0008(5) -.0082(5) C1 .0368(6) .0359(6) .0241(6) .0032(5) .0098(5) .0029(5) C2 .0310(6) .0398(7) .0303(6) -.0067(5) .0044(5) .0042(5) C3 .0311(6) .0377(7) .0272(6) -.0044(5) .0054(5) -.0023(5) C4 .0242(5) .0363(6) .0218(6) .0000(5) .0038(4) .0021(5) C5 .0259(5) .0396(7) .0218(6) -.0039(5) .0058(4) -.0016(5) C6 .0351(6) .0455(7) .0249(6) -.0044(5) .0046(5) .0075(5) C7 .0307(6) .0343(6) .0345(7) -.0021(5) .0042(5) .0045(5) C8 .0438(8) .0415(8) .0502(9) -.0110(6) .0024(7) .0083(6) C9 .0461(9) .0389(8) .0789(13) -.0095(7) .0134(8) -.0072(8) C10 .0462(9) .0557(10) .0552(11) -.0135(7) .0044(8) -.0203(8) C11 .0305(6) .0333(6) .0289(6) .0000(5) .0027(5) -.0010(5) C12 .0290(6) .0320(6) .0225(6) .0010(5) .0042(4) .0031(5) C13 .0283(6) .0442(7) .0311(7) -.0008(5) .0049(5) -.0033(6) C14 .0444(10) .127(2) .0913(17) .0229(12) -.0061(11) .0424(16) C15 .0765(13) .0795(14) .0373(9) -.0032(10) -.0148(9) -.0015(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 C13 O3 C14 116.12(14) C2 N1 C1 117.09(11) C11 N2 C15 114.95(13) C11 N2 C10 113.56(12) C15 N2 C10 109.71(15) N1 C1 C12 125.25(12) N1 C1 Cl1 112.95(9) C12 C1 Cl1 121.71(10) N1 C2 C3 124.35(12) N1 C2 Cl2 116.19(10) C3 C2 Cl2 119.45(10) C4 C3 C2 117.37(12) C3 C4 C12 121.20(11) C3 C4 C5 121.78(11) C12 C4 C5 116.95(11) O1 C5 C4 108.72(10) O1 C5 C6 113.01(11) C4 C5 C6 107.07(10) O1 C5 C13 107.59(10) C4 C5 C13 111.20(10) C6 C5 C13 109.29(10) C7 C6 C5 109.15(11) C11 C7 C6 120.22(12) C11 C7 C8 121.92(13) C6 C7 C8 117.86(12) C9 C8 C7 110.30(13) C10 C9 C8 109.10(14) N2 C10 C9 111.85(14) C7 C11 N2 123.83(12) C7 C11 C12 116.61(12) N2 C11 C12 119.42(11) C1 C12 C4 114.47(11) C1 C12 C11 127.32(12) C4 C12 C11 117.94(11) O2 C13 O3 124.75(13) O2 C13 C5 122.75(13) O3 C13 C5 112.39(11) 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 Cl1 C1 . 1.7374(13) ? Cl2 C2 . 1.7393(13) ? O1 C5 . 1.4208(15) ? O2 C13 . 1.1954(17) ? O3 C13 . 1.3250(18) ? O3 C14 . 1.454(2) ? N1 C2 . 1.3215(18) yes N1 C1 . 1.3349(18) yes N2 C11 . 1.4094(18) ? N2 C15 . 1.456(2) ? N2 C10 . 1.480(2) ? C1 C12 . 1.4045(16) yes C2 C3 . 1.3860(17) yes C3 C4 . 1.3772(18) yes C4 C12 . 1.4143(17) yes C4 C5 . 1.5136(16) ? C5 C6 . 1.5200(19) ? C5 C13 . 1.5484(18) ? C6 C7 . 1.505(2) ? C7 C11 . 1.3513(19) ? C7 C8 . 1.5071(19) ? C8 C9 . 1.505(3) ? C9 C10 . 1.502(3) ? C11 C12 . 1.4934(17) ? 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 O1 H1A N1 4_675 0.82 2.25 3.045(2) 165.26 yes 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 C2 N1 C1 C12 -0.4(2) yes C2 N1 C1 Cl1 176.18(10) ? C1 N1 C2 C3 -4.1(2) ? C1 N1 C2 Cl2 177.09(10) ? N1 C2 C3 C4 4.0(2) ? Cl2 C2 C3 C4 -177.22(10) ? C2 C3 C4 C12 0.58(19) ? C2 C3 C4 C5 -176.29(12) ? C3 C4 C5 O1 11.33(17) ? C12 C4 C5 O1 -165.67(11) ? C3 C4 C5 C6 133.73(13) ? C12 C4 C5 C6 -43.26(14) ? C3 C4 C5 C13 -106.95(14) ? C12 C4 C5 C13 76.06(14) ? O1 C5 C6 C7 179.47(10) ? C4 C5 C6 C7 59.79(13) ? C13 C5 C6 C7 -60.76(13) ? C5 C6 C7 C11 -33.91(17) ? C5 C6 C7 C8 144.95(13) ? C11 C7 C8 C9 -14.8(2) ? C6 C7 C8 C9 166.37(14) ? C7 C8 C9 C10 47.68(18) ? C11 N2 C10 C9 41.98(19) ? C15 N2 C10 C9 172.14(15) ? C8 C9 C10 N2 -63.39(18) ? C6 C7 C11 N2 171.89(13) ? C8 C7 C11 N2 -6.9(2) ? C6 C7 C11 C12 -12.40(19) ? C8 C7 C11 C12 168.79(13) ? C15 N2 C11 C7 -134.36(17) ? C10 N2 C11 C7 -6.9(2) ? C15 N2 C11 C12 50.05(19) ? C10 N2 C11 C12 177.53(13) ? N1 C1 C12 C4 4.43(19) ? Cl1 C1 C12 C4 -171.87(10) ? N1 C1 C12 C11 178.23(13) ? Cl1 C1 C12 C11 1.9(2) ? C3 C4 C12 C1 -4.35(18) ? C5 C4 C12 C1 172.67(11) ? C3 C4 C12 C11 -178.76(12) ? C5 C4 C12 C11 -1.75(17) ? C7 C11 C12 C1 -141.61(14) ? N2 C11 C12 C1 34.3(2) ? C7 C11 C12 C4 31.99(17) ? N2 C11 C12 C4 -152.10(12) ? C14 O3 C13 O2 -0.3(3) yes C14 O3 C13 C5 175.96(18) ? O1 C5 C13 O2 82.27(17) ? C4 C5 C13 O2 -158.78(14) ? C6 C5 C13 O2 -40.79(19) ? O1 C5 C13 O3 -94.06(14) ? C4 C5 C13 O3 24.90(16) ? C6 C5 C13 O3 142.89(13) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9285799 2 PubChem 101000993