#------------------------------------------------------------------------------ #$Date: 2018-08-07 15:33:59 +0100 (Tue, 07 Aug 2018) $ #$Revision: 209447 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/04/2000415.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_2000415 loop_ _publ_author_name 'Verdonk, M. L.' 'Kanters, J. A.' 'Kroon, J.' _publ_contact_author ; Marcel L. Verdonk Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht ; _publ_section_title ; Structure of eltoprazine ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2271 _journal_page_last 2273 _journal_paper_doi 10.1107/S0108270192008904 _journal_volume 48 _journal_year 1992 _chemical_formula_moiety 'C12 H17 N2 O2 1+,(Cl 1-)1' _chemical_formula_sum 'C12 H17 Cl N2 O2' _chemical_formula_weight 256.73 _chemical_name_systematic ; 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine hydrochloride ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method 'PLATON TABLE ACC option' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3150(10) _cell_length_b 7.941(2) _cell_length_c 21.393(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 18.01 _cell_measurement_theta_min 15.67 _cell_volume 1242.7(4) _computing_cell_refinement 'SET4 (de Boer, 1984)' _computing_data_reduction 'HELENA (Spek, 1990a)' _computing_molecular_graphics 'EUCLID (Spek, 1982)' _computing_publication_material 'PLATON92 (Spek, 1990b)' _computing_structure_refinement 'SHELX76 (Sheldrick, 1976)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 295 _diffrn_measurement_device 'Enraf Nonius CAD4' _diffrn_measurement_method 'Background-peak-background from \w/2\q scan' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.120 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2998 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 0.10 _diffrn_standards_decay_% 1.2 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.372 _exptl_crystal_description plate _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.48 _refine_diff_density_min -0.48 _refine_ls_goodness_of_fit_obs 1.41 _refine_ls_hydrogen_treatment ; No hydrogen parameters were refined except for an overall displacement parameter ; _refine_ls_matrix_type full _refine_ls_number_constraints 51 _refine_ls_number_parameters 171 _refine_ls_number_reflns 850 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.069 _refine_ls_shift/esd_max 0.091 _refine_ls_shift/esd_mean 0.025 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F)+0.0004F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.063 _reflns_number_observed 850 _reflns_number_total 2639 _reflns_observed_criterion I>2.5\s(I) _cod_data_source_file ab1011.cif _cod_data_source_block eltoprazine _cod_depositor_comments ; Removing duplicate rows from the ATOM_TYPE loop. Antanas Vaitkus, 2018-08-07 Adding the _atom_site_type_symbol data item. Antanas Vaitkus, 2018-08-07 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(F)+0.0004F^2^]' 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^(F)+0.0004F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_formula_sum 'C12 H17 N2 O2 Cl1' _cod_database_code 2000415 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z 1/2-x,-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 O1 0.037(5) 0.047(4) 0.058(5) -0.001(4) -0.009(4) -0.018(4) O2 0.036(5) 0.021(3) 0.048(4) 0.001(4) -0.005(4) -0.001(3) N1 0.042(5) 0.016(4) 0.030(5) 0.005(4) 0.000(4) -0.008(4) N2 0.045(6) 0.040(5) 0.034(5) -0.002(5) -0.019(5) 0.000(4) C1 0.026(6) 0.041(7) 0.013(5) 0.001(6) -0.002(5) 0.001(5) C2 0.033(7) 0.043(7) 0.046(7) 0.000(6) 0.004(6) -0.014(6) C3 0.034(7) 0.036(6) 0.040(6) 0.007(6) 0.014(6) 0.001(5) C4 0.026(6) 0.027(6) 0.034(6) 0.008(5) 0.013(5) 0.008(5) C5 0.028(6) 0.028(6) 0.032(6) -0.009(5) 0.006(5) 0.004(5) C6 0.045(7) 0.022(5) 0.052(7) -0.006(7) 0.000(6) 0.000(6) C7 0.033(7) 0.039(6) 0.038(6) 0.001(7) 0.009(6) 0.011(6) C8 0.026(7) 0.039(7) 0.043(7) 0.003(6) -0.008(6) 0.008(5) C9 0.045(7) 0.045(6) 0.033(6) -0.001(7) -0.004(6) 0.009(6) C10 0.053(8) 0.034(6) 0.040(6) -0.011(6) -0.003(6) -0.004(5) C11 0.024(5) 0.034(5) 0.044(6) 0.007(6) 0.003(6) -0.010(6) C12 0.019(6) 0.046(6) 0.039(6) -0.002(6) 0.013(5) -0.016(6) Cl1 0.052(2) 0.0370(10) 0.059(2) -0.009(2) -0.014(2) -0.002(2) loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type O1 O 0.1400(10) 0.4225(8) 0.0017(3) 0.047(3) Uani O2 O 0.4210(10) 0.4142(7) 0.0945(3) 0.035(2) Uani N1 N 0.4980(10) 0.6923(9) 0.1637(3) 0.029(3) Uani N2 N 0.8300(10) 0.7830(10) 0.2272(4) 0.040(3) Uani C1 C 0.1760(10) 0.5580(10) 0.0392(4) 0.027(3) Uani C2 C 0.2750(10) 0.2890(10) 0.0058(5) 0.041(4) Uani C3 C 0.329(2) 0.2640(10) 0.0716(4) 0.037(4) Uani C4 C 0.3120(10) 0.5560(10) 0.0840(4) 0.029(3) Uani C5 C 0.3470(10) 0.7000(10) 0.1203(4) 0.029(3) Uani C6 C 0.2360(10) 0.8370(10) 0.1130(5) 0.040(4) Uani C7 C 0.0950(10) 0.8340(10) 0.0701(4) 0.037(4) Uani C8 C 0.0650(10) 0.7010(10) 0.0331(5) 0.036(4) Uani C9 C 0.502(2) 0.8310(10) 0.2085(4) 0.041(4) Uani C10 C 0.6470(10) 0.8050(10) 0.2568(4) 0.042(4) Uani C11 C 0.8240(10) 0.6420(10) 0.1808(5) 0.034(3) Uani C12 C 0.6780(10) 0.6770(10) 0.1325(4) 0.035(3) Uani Cl1 Cl 0.8903(4) 0.1561(3) 0.17850(10) 0.0490(10) Uani H1 H 0.867 0.898 0.2035 0.056(7) Uiso H2 H 0.930 0.755 0.2628 0.056(7) Uiso H3 H 0.217 0.174 -0.0123 0.056(7) Uiso H4 H 0.394 0.324 -0.0214 0.056(7) Uiso H5 H 0.421 0.158 0.0747 0.056(7) Uiso H6 H 0.209 0.240 0.0995 0.056(7) Uiso H7 H 0.258 0.948 0.1411 0.056(7) Uiso H8 H 0.007 0.942 0.0662 0.056(7) Uiso H9 H -0.044 0.703 -0.0010 0.056(7) Uiso H10 H 0.530 0.947 0.1838 0.056(7) Uiso H11 H 0.371 0.840 0.2313 0.056(7) Uiso H12 H 0.615 0.694 0.2836 0.056(7) Uiso H13 H 0.651 0.913 0.2874 0.056(7) Uiso H14 H 0.955 0.630 0.1579 0.056(7) Uiso H15 H 0.792 0.525 0.2048 0.056(7) Uiso H16 H 0.673 0.575 0.0991 0.056(7) Uiso H17 H 0.709 0.793 0.1086 0.056(7) Uiso loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H 0 0 International_Tables_Vol_IV_Table_2.3.1 O 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 N 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 Cl 0.132 0.159 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 3 1 2 1 1 2 2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O1 C2 . . . 114.1(7) yes C3 O2 C4 . . . 110.0(7) yes C5 N1 C9 . . . 113.9(8) yes C5 N1 C12 . . . 113.2(6) yes C9 N1 C12 . . . 109.9(8) yes C10 N2 C11 . . . 110.1(6) yes O1 C1 C4 . . . 122.4(7) yes O1 C1 C8 . . . 118.1(7) yes C4 C1 C8 . . . 119.4(8) yes O1 C2 C3 . . . 109.8(8) yes O2 C3 C2 . . . 109.6(7) yes O2 C4 C1 . . . 122.1(7) yes O2 C4 C5 . . . 117.6(7) yes C1 C4 C5 . . . 120.3(7) yes N1 C5 C4 . . . 117.4(7) yes N1 C5 C6 . . . 124.2(8) yes C4 C5 C6 . . . 118.4(7) yes C5 C6 C7 . . . 120.4(8) yes C6 C7 C8 . . . 122.0(7) yes C1 C8 C7 . . . 119.3(8) yes N1 C9 C10 . . . 111.3(8) yes N2 C10 C9 . . . 111.1(8) yes N2 C11 C12 . . . 109.7(6) yes N1 C12 C11 . . . 109.6(7) yes C10 N2 H1 . . . 109.0 no C10 N2 H2 . . . 109.5 no C11 N2 H1 . . . 109.2 no C11 N2 H2 . . . 109.5 no H1 N2 H2 . . . 109.6 no O1 C2 H3 . . . 109.2 no O1 C2 H4 . . . 109.1 no C3 C2 H3 . . . 109.5 no C3 C2 H4 . . . 109 no H3 C2 H4 . . . 110 no O2 C3 H5 . . . 109 no O2 C3 H6 . . . 109.6 no C2 C3 H5 . . . 109.3 no C2 C3 H6 . . . 110 no H5 C3 H6 . . . 110 no C5 C6 H7 . . . 119.9 no C7 C6 H7 . . . 119.7 no C6 C7 H8 . . . 119.0 no C8 C7 H8 . . . 119.0 no C1 C8 H9 . . . 120.1 no C7 C8 H9 . . . 120.6 no N1 C9 H10 . . . 109.0 no N1 C9 H11 . . . 109 no C10 C9 H10 . . . 109 no C10 C9 H11 . . . 109.1 no H10 C9 H11 . . . 109 no N2 C10 H12 . . . 109.0 no N2 C10 H13 . . . 109.0 no C9 C10 H12 . . . 109.1 no C9 C10 H13 . . . 109.2 no H12 C10 H13 . . . 109 no N2 C11 H14 . . . 109.9 no N2 C11 H15 . . . 109 no C12 C11 H14 . . . 109 no C12 C11 H15 . . . 109.1 no H14 C11 H15 . . . 109.3 no N1 C12 H16 . . . 109.2 no N1 C12 H17 . . . 109.3 no C11 C12 H16 . . . 109.8 no C11 C12 H17 . . . 109.4 no H16 C12 H17 . . . 110 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . . 1.370(10) yes O1 C2 . . 1.450(10) yes O2 C3 . . 1.450(10) yes O2 C4 . . 1.400(10) yes N1 C5 . . 1.440(10) yes N1 C9 . . 1.460(10) yes N1 C12 . . 1.480(10) yes N2 C10 . . 1.490(10) yes N2 C11 . . 1.500(10) yes C1 C4 . . 1.380(10) yes C1 C8 . . 1.400(10) yes C2 C3 . . 1.480(10) yes C4 C5 . . 1.410(10) yes C5 C6 . . 1.370(10) yes C6 C7 . . 1.380(10) yes C7 C8 . . 1.340(10) yes C9 C10 . . 1.500(10) yes C11 C12 . . 1.510(10) yes N2 H1 . . 1.08 no N2 H2 . . 1.08 no C2 H3 . . 1.08 no C2 H4 . . 1.08 no C3 H5 . . 1.08 no C3 H6 . . 1.08 no C6 H7 . . 1.08 no C7 H8 . . 1.08 no C8 H9 . . 1.08 no C9 H10 . . 1.08 no C9 H11 . . 1.08 no C10 H12 . . 1.08 no C10 H13 . . 1.08 no C11 H14 . . 1.08 no C11 H15 . . 1.09 no C12 H16 . . 1.08 no C12 H17 . . 1.08 no