#------------------------------------------------------------------------------ #$Date: 2025-08-21 23:24:23 +0100 (Thu, 21 Aug 2025) $ #$Revision: 301857 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/23/7112341.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7112341 loop_ _publ_author_name 'do Pim, Walace D.' 'Oliveira, Willian X. C.' 'Ribeiro, Marcos A.' 'de Faria, \'Erica N' 'Teixeira, Ivo F.' 'Stumpf, Humberto O.' 'Lago, Rochel M.' 'Pereira, Cynthia L. M.' 'Pinheiro, Carlos B.' 'Figueiredo, Jr, Jo\~ao C D' 'Nunes, Wallace C.' 'de Souza, Patterson P.' 'Pedroso, Emerson F.' 'Castellano, Mar\'ia' 'Cano, Joan' 'Julve, Miguel' _publ_section_title ; A pH-triggered bistable copper(II) metallacycle as a reversible emulsion switch for biphasic processes. ; _journal_issue 92 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 10778 _journal_page_last 10780 _journal_paper_doi 10.1039/c3cc46242k _journal_volume 49 _journal_year 2013 _chemical_formula_sum 'C11 H12 N O3' _chemical_formula_weight 206.22 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 93.502(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.6560(2) _cell_length_b 9.1479(2) _cell_length_c 16.3406(4) _cell_measurement_reflns_used 6741 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.4672 _cell_measurement_theta_min 3.2331 _cell_volume 993.10(4) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 10.4186 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0060634 _diffrn_orient_matrix_UB_12 0.0323697 _diffrn_orient_matrix_UB_13 -0.0395423 _diffrn_orient_matrix_UB_21 0.02409 _diffrn_orient_matrix_UB_22 0.0690292 _diffrn_orient_matrix_UB_23 0.0177544 _diffrn_orient_matrix_UB_31 0.1037964 _diffrn_orient_matrix_UB_32 -0.0141319 _diffrn_orient_matrix_UB_33 -0.0036916 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_unetI/netI 0.0198 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 12200 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 3.35 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 436 _exptl_crystal_size_max 0.5761 _exptl_crystal_size_mid 0.175 _exptl_crystal_size_min 0.1204 _refine_diff_density_max 0.254 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.94 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 2039 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.94 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0327 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.1177P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0993 _refine_ls_wR_factor_ref 0.103 _reflns_number_gt 1654 _reflns_number_total 2039 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL edpba_f in P2(1)/c CELL 0.71073 6.6560 9.1479 16.3406 90.000 93.502 90.000 ZERR 4.00 0.0002 0.0002 0.0004 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 44 48 4 12 MERG 2 SHEL 50 0.8 FMAP 2 PLAN 25 ACTA HTAB 2.00000 BOND $H LIST 4 L.S. 20 TEMP -153.00 WGHT 0.047200 0.149700 FVAR 0.15313 O2 4 0.308960 0.098303 0.537130 11.00000 0.04097 0.01693 = 0.05502 0.00274 0.00936 0.00007 O1 4 0.318074 -0.113547 0.607216 11.00000 0.02890 0.01873 = 0.02697 -0.00295 0.00109 -0.00188 N1 3 0.189873 -0.265714 0.482411 11.00000 0.02314 0.01936 = 0.01864 0.00266 0.00021 0.00293 O3 4 0.151459 -0.060987 0.402008 11.00000 0.04005 0.03365 = 0.03853 0.01848 -0.00649 -0.00225 C9 1 0.399276 -0.533177 0.512329 11.00000 0.01843 0.01503 = 0.01726 0.00199 -0.00020 -0.00038 AFIX 23 H9A 2 0.418905 -0.638132 0.525249 11.00000 -1.50000 H9B 2 0.356838 -0.483658 0.562306 11.00000 -1.50000 AFIX 0 C4 1 0.235859 -0.517029 0.444578 11.00000 0.01455 0.02209 = 0.01584 0.00230 0.00316 -0.00270 C8 1 -0.000630 -0.366425 0.362374 11.00000 0.01758 0.03389 = 0.02035 0.00473 0.00162 0.00424 AFIX 43 H8 2 -0.065088 -0.274991 0.352222 11.00000 -1.20000 AFIX 0 C5 1 0.181536 -0.635162 0.394539 11.00000 0.01861 0.02405 = 0.02237 -0.00173 0.00421 -0.00231 AFIX 43 H5 2 0.240587 -0.728109 0.405807 11.00000 -1.20000 AFIX 0 C2 1 0.197911 -0.121432 0.466763 11.00000 0.01612 0.02266 = 0.03123 0.00793 0.00395 0.00316 C3 1 0.140356 -0.382517 0.428036 11.00000 0.01609 0.02360 = 0.01647 0.00185 0.00379 -0.00084 C10 1 0.397909 -0.039469 0.681537 11.00000 0.03541 0.03222 = 0.03230 -0.01514 0.00733 -0.00796 AFIX 23 H10A 2 0.296014 0.028145 0.701840 11.00000 -1.20000 H10B 2 0.519318 0.017658 0.670022 11.00000 -1.20000 AFIX 0 C11 1 0.449800 -0.155317 0.744265 11.00000 0.02765 0.04933 = 0.02430 -0.00949 0.00230 -0.00775 AFIX 133 H11A 2 0.329382 -0.212932 0.753901 11.00000 -1.50000 H11B 2 0.499985 -0.109172 0.795645 11.00000 -1.50000 H11C 2 0.553936 -0.219536 0.724235 11.00000 -1.50000 AFIX 0 C7 1 -0.046291 -0.484831 0.311895 11.00000 0.01620 0.04921 = 0.01880 0.00063 -0.00186 -0.00150 AFIX 43 H7 2 -0.138883 -0.473725 0.265726 11.00000 -1.20000 AFIX 0 C6 1 0.042422 -0.619465 0.328393 11.00000 0.02187 0.03771 = 0.02158 -0.00936 0.00285 -0.00794 AFIX 43 H6 2 0.007983 -0.701052 0.294404 11.00000 -1.20000 AFIX 0 C1 1 0.279745 -0.030854 0.540878 11.00000 0.01867 0.01808 = 0.03731 0.00289 0.00761 0.00365 H1 2 0.228559 -0.286380 0.532954 11.00000 -1.50000 HKLF 4 REM edpba_f in P2(1)/c REM R1 = 0.0325 for 1654 Fo > 4sig(Fo) and 0.0409 for all 2039 data REM 139 parameters refined using 0 restraints END WGHT 0.0471 0.1496 REM Highest difference peak 0.240, deepest hole -0.182, 1-sigma level 0.037 Q1 1 0.3146 -0.5193 0.4768 11.00000 0.05 0.24 Q2 1 0.5000 -0.5000 0.5000 10.50000 0.05 0.23 ; _cod_data_source_file c3cc46242k.txt _cod_data_source_block edpba_f _cod_depositor_comments 'Adding full bibliography for 7112340--7112342.cif.' _cod_database_code 7112341 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O2 O 0.30895(15) 0.09833(10) 0.53717(6) 0.0372(3) Uani 1 1 d . O1 O 0.31811(13) -0.11352(9) 0.60725(5) 0.0247(2) Uani 1 1 d . N1 N 0.18987(14) -0.26575(11) 0.48240(6) 0.0203(2) Uani 1 1 d . O3 O 0.15137(14) -0.06099(11) 0.40201(6) 0.0376(3) Uani 1 1 d . C9 C 0.39927(15) -0.53319(11) 0.51232(7) 0.0167(3) Uani 1 1 d . H9A H 0.4189 -0.6381 0.5252 0.025 Uiso 1 1 calc R H9B H 0.3568 -0.4837 0.5623 0.025 Uiso 1 1 calc R C4 C 0.23584(16) -0.51705(12) 0.44460(6) 0.0173(3) Uani 1 1 d . C8 C -0.00067(18) -0.36643(14) 0.36236(7) 0.0238(3) Uani 1 1 d . H8 H -0.0651 -0.275 0.3522 0.029 Uiso 1 1 calc R C5 C 0.18154(17) -0.63516(13) 0.39452(7) 0.0214(3) Uani 1 1 d . H5 H 0.2407 -0.7281 0.4057 0.026 Uiso 1 1 calc R C2 C 0.19792(17) -0.12148(13) 0.46678(8) 0.0230(3) Uani 1 1 d . C3 C 0.14039(17) -0.38253(13) 0.42806(7) 0.0184(3) Uani 1 1 d . C10 C 0.3979(2) -0.03953(15) 0.68155(8) 0.0329(3) Uani 1 1 d . H10A H 0.296 0.0281 0.7019 0.039 Uiso 1 1 calc R H10B H 0.5193 0.0176 0.67 0.039 Uiso 1 1 calc R C11 C 0.4499(2) -0.15540(16) 0.74427(8) 0.0335(3) Uani 1 1 d . H11A H 0.3295 -0.213 0.7539 0.05 Uiso 1 1 calc R H11B H 0.5001 -0.1093 0.7956 0.05 Uiso 1 1 calc R H11C H 0.554 -0.2196 0.7242 0.05 Uiso 1 1 calc R C7 C -0.04633(17) -0.48476(16) 0.31185(7) 0.0280(3) Uani 1 1 d . H7 H -0.1388 -0.4736 0.2657 0.034 Uiso 1 1 calc R C6 C 0.04236(19) -0.61946(15) 0.32838(7) 0.0267(3) Uani 1 1 d . H6 H 0.0078 -0.7011 0.2944 0.032 Uiso 1 1 calc R C1 C 0.27975(17) -0.03078(13) 0.54091(8) 0.0243(3) Uani 1 1 d . H1 H 0.229(2) -0.2862(17) 0.5333(10) 0.036 Uiso 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0408(6) 0.0168(5) 0.0548(7) 0.0027(4) 0.0093(5) 0.0001(4) O1 0.0288(5) 0.0185(4) 0.0267(5) -0.0030(3) 0.0010(4) -0.0019(3) N1 0.0229(5) 0.0192(5) 0.0187(5) 0.0027(4) 0.0003(4) 0.0029(4) O3 0.0400(6) 0.0333(6) 0.0385(6) 0.0185(4) -0.0064(4) -0.0022(4) C9 0.0182(6) 0.0149(5) 0.0170(5) 0.0022(4) -0.0004(4) -0.0005(4) C4 0.0144(5) 0.0218(6) 0.0158(5) 0.0024(4) 0.0030(4) -0.0027(4) C8 0.0173(6) 0.0340(7) 0.0200(6) 0.0046(5) 0.0016(5) 0.0042(5) C5 0.0185(6) 0.0240(6) 0.0220(6) -0.0017(5) 0.0041(5) -0.0023(4) C2 0.0163(6) 0.0221(6) 0.0309(7) 0.0076(5) 0.0037(5) 0.0029(4) C3 0.0158(5) 0.0234(6) 0.0162(5) 0.0017(4) 0.0037(4) -0.0009(4) C10 0.0351(7) 0.0318(7) 0.0324(7) -0.0149(6) 0.0074(6) -0.0077(6) C11 0.0275(7) 0.0491(9) 0.0240(6) -0.0093(6) 0.0025(5) -0.0076(6) C7 0.0160(6) 0.0490(8) 0.0186(6) 0.0006(6) -0.0020(4) -0.0017(5) C6 0.0215(6) 0.0376(7) 0.0212(6) -0.0090(5) 0.0028(5) -0.0077(5) C1 0.0186(6) 0.0177(6) 0.0373(7) 0.0030(5) 0.0074(5) 0.0036(4) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 9 -2 -4 0.2676 0 0 4 0.0676 0 -13 -4 0.0716 0 -3 0 0.0923 0 3 -22 0.0923 0 -3 -1 0.0585 0 13 5 0.0595 -2 0 1 0.2796 1 3 1 0.1325 1 -4 -2 0.0931 -1 -3 -1 0.0914 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C1 O1 C10 117.01(10) . . C2 N1 C3 129.18(10) . . C2 N1 H1 112.2(10) . . C3 N1 H1 118.5(10) . . C4 C9 C9 111.57(11) . 3_646 C4 C9 H9A 109.3 . . C9 C9 H9A 109.3 3_646 . C4 C9 H9B 109.3 . . C9 C9 H9B 109.3 3_646 . H9A C9 H9B 108 . . C5 C4 C3 118.03(10) . . C5 C4 C9 120.33(10) . . C3 C4 C9 121.59(10) . . C7 C8 C3 119.42(11) . . C7 C8 H8 120.3 . . C3 C8 H8 120.3 . . C6 C5 C4 121.03(11) . . C6 C5 H5 119.5 . . C4 C5 H5 119.5 . . O3 C2 N1 126.84(12) . . O3 C2 C1 119.85(11) . . N1 C2 C1 113.29(10) . . C8 C3 C4 121.20(11) . . C8 C3 N1 121.66(11) . . C4 C3 N1 117.12(10) . . O1 C10 C11 107.29(10) . . O1 C10 H10A 110.3 . . C11 C10 H10A 110.3 . . O1 C10 H10B 110.3 . . C11 C10 H10B 110.3 . . H10A C10 H10B 108.5 . . C10 C11 H11A 109.5 . . C10 C11 H11B 109.5 . . H11A C11 H11B 109.5 . . C10 C11 H11C 109.5 . . H11A C11 H11C 109.5 . . H11B C11 H11C 109.5 . . C8 C7 C6 120.25(11) . . C8 C7 H7 119.9 . . C6 C7 H7 119.9 . . C7 C6 C5 120.01(11) . . C7 C6 H6 120 . . C5 C6 H6 120 . . O2 C1 O1 125.22(12) . . O2 C1 C2 122.77(12) . . O1 C1 C2 111.99(10) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O2 C1 1.1991(15) . O1 C1 1.3340(15) . O1 C10 1.4614(15) . N1 C2 1.3458(15) . N1 C3 1.4151(15) . N1 H1 0.876(15) . O3 C2 1.2174(15) . C9 C4 1.5109(15) . C9 C9 1.548(2) 3_646 C9 H9A 0.99 . C9 H9B 0.99 . C4 C5 1.3898(16) . C4 C3 1.4035(16) . C8 C7 1.3838(18) . C8 C3 1.3901(16) . C8 H8 0.95 . C5 C6 1.3872(17) . C5 H5 0.95 . C2 C1 1.5401(18) . C10 C11 1.500(2) . C10 H10A 0.99 . C10 H10B 0.99 . C11 H11A 0.98 . C11 H11B 0.98 . C11 H11C 0.98 . C7 C6 1.3858(19) . C7 H7 0.95 . C6 H6 0.95 . loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139184454