# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Stephen Moggach' ; Dr Stephen Moggach RSE Personal Research Fellow The University of Edinburgh Joseph Black Building West Mains Road Edinburgh EH9 3JJ ; 'Matthew Rosseinsky' '' 'Jamie Gould' '' _publ_contact_author_address ; Dr Stephen Moggach RSE Personal Research Fellow The University of Edinburgh Joseph Black Building West Mains Road Edinburgh EH9 3JJ ; _publ_contact_author_email smoggach@staffmail.ed.ac.uk _publ_contact_author_phone '+44(0)131 6504806' #TrackingRef '- all.cif' _publ_contact_author_name 'Stephen A. Moggach' data_ambient _database_code_depnum_ccdc_archive 'CCDC 856787' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'st0014 in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C8 H18 Cu2 N2 O12' # Given Formula = C10 H20 Cu1 N4 O5 # Dc = 1.57 Fooo = 468.00 Mu = 15.39 M = 169.92 # Found Formula = C8 H18 Cu2 N2 O12 # Dc = 2.12 FOOO = 468.00 Mu = 30.22 M = 230.66 _chemical_formula_sum 'C8 H18 Cu2 N2 O12' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _publ_section_exptl_refinement ; 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 118 A sphere of data was collected, which resulted in a few missing reflections. 915_ALERT_3_C Low Friedel Pair Coverage ...................... 72 Perc. High-friedel coverage is not needed as the hand of the Aspartate ligand is known. 142_ALERT_4_C su on b - Axis Small or Missing ................ 0.00010 Ang. These do appear to be somewhat smaller than expected, yet the statistics produced on final integration appear to be consistent. 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! 153_ALERT_1_G The su's on the Cell Axes are Equal .......... 0.00010 Ang. No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.13 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 9.51720(10) _cell_length_b 10.04180(10) _cell_length_c 7.56210(10) _cell_angle_alpha 90 _cell_angle_beta 93.9840(10) _cell_angle_gamma 90 _cell_volume 720.962(14) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'C 2y' 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.67 _cell_measurement_reflns_used 4234 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 29.5 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.1 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_max 0.2 _exptl_crystal_density_diffrn 2.125 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.022 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 1.0000 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed X-ray tube' _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 5337 _reflns_number_total 1732 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections without Friedels Law is 1732 # Number of reflections with Friedels Law is 1000 # Theoretical number of reflections is about 1067 _diffrn_reflns_theta_min 2.700 _diffrn_reflns_theta_max 30.162 _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 25.034 _diffrn_measured_fraction_theta_full 0.981 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 10 _oxford_diffrn_Wilson_B_factor 1.18 _oxford_diffrn_Wilson_scale 18.32 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.40 _refine_diff_density_max 0.42 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 1732 _refine_ls_number_restraints 1 _refine_ls_number_parameters 110 _oxford_refine_ls_R_factor_ref 0.0254 _refine_ls_wR_factor_ref 0.0513 _refine_ls_goodness_of_fit_ref 0.9748 _refine_ls_shift/su_max 0.0005347 _refine_ls_shift/su_mean 0.0000261 # The values computed from all data _oxford_reflns_number_all 1732 _refine_ls_R_factor_all 0.0254 _refine_ls_wR_factor_all 0.0513 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1607 _refine_ls_R_factor_gt 0.0223 _refine_ls_wR_factor_gt 0.0498 _refine_ls_abs_structure_Flack 0.066(14) _refine_ls_abs_structure_details 'Flack (1983), 732 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.37P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.23637(3) 1.00044(10) 0.87457(3) 0.0150 1.0000 Uani . . . . . . O1 O 0.3289(2) 0.82851(19) 0.8458(2) 0.0213 1.0000 Uani . . . . . . O2 O 0.3899(2) 0.6834(2) 0.6449(2) 0.0200 1.0000 Uani . . . . . . O3 O 0.30706(17) 1.0081(3) 0.12264(19) 0.0176 1.0000 Uani . . . . . . O4 O 0.1185(2) 0.8924(2) 0.1915(3) 0.0203 1.0000 Uani . . . . . . O5 O 0.1285(2) 1.1657(2) 0.8769(2) 0.0222 1.0000 Uani . . . . . . O6 O 0.4270(2) 1.1147(2) 0.7770(3) 0.0266 1.0000 Uani . . . . . . N1 N 0.1454(2) 0.9579(2) 0.6359(3) 0.0142 1.0000 Uani . . . . . . C1 C 0.3220(3) 0.7814(3) 0.6873(3) 0.0148 1.0000 Uani . . . . . . C2 C 0.2258(3) 0.8536(2) 0.5486(3) 0.0134 1.0000 Uani . . . . . . C3 C 0.3148(3) 0.9141(3) 0.4085(3) 0.0151 1.0000 Uani . . . . . . C4 C 0.2365(3) 0.9402(3) 0.2305(3) 0.0139 1.0000 Uani . . . . . . H31 H 0.3531 0.9993 0.4532 0.0186 1.0000 Uiso R . . . . . H32 H 0.3895 0.8525 0.3882 0.0186 1.0000 Uiso R . . . . . H21 H 0.1574 0.7912 0.4914 0.0158 1.0000 Uiso R . . . . . H11 H 0.1383 1.0292 0.5704 0.0178 1.0000 Uiso R . . . . . H12 H 0.0620 0.9296 0.6504 0.0178 1.0000 Uiso R . . . . . H51 H 0.1311 1.2100 0.9715 0.0500 1.0000 Uiso R . . . . . H52 H 0.0501 1.1671 0.8206 0.0500 1.0000 Uiso R . . . . . H62 H 0.5091 1.0925 0.8128 0.0500 1.0000 Uiso R . . . . . H61 H 0.4137 1.1968 0.7896 0.0500 1.0000 Uiso R . . . . . 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 Cu1 0.01923(15) 0.01549(13) 0.00985(12) -0.00029(16) -0.00134(9) 0.00287(17) O1 0.0344(11) 0.0198(9) 0.0090(9) 0.0010(7) -0.0043(8) 0.0073(8) O2 0.0237(10) 0.0170(9) 0.0193(9) -0.0012(8) 0.0011(7) 0.0061(7) O3 0.0194(8) 0.0223(9) 0.0111(7) 0.0017(11) 0.0003(6) 0.0003(12) O4 0.0170(10) 0.0237(10) 0.0195(10) 0.0009(8) -0.0029(7) -0.0035(7) O5 0.0236(10) 0.0206(10) 0.0216(9) -0.0074(8) -0.0048(8) 0.0072(8) O6 0.0220(11) 0.0216(10) 0.0361(12) 0.0029(9) 0.0013(9) 0.0020(8) N1 0.0139(10) 0.0200(11) 0.0089(9) 0.0007(7) 0.0009(8) 0.0029(7) C1 0.0151(13) 0.0137(12) 0.0154(12) 0.0030(9) 0.0005(10) -0.0033(9) C2 0.0190(13) 0.0142(12) 0.0068(10) -0.0009(9) -0.0007(9) 0.0015(10) C3 0.0135(13) 0.0184(13) 0.0130(12) 0.0021(9) -0.0012(9) 0.0000(10) C4 0.0209(14) 0.0123(10) 0.0086(11) -0.0028(9) 0.0015(9) 0.0046(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.17130(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O3 1_556 1.9500(14) yes Cu1 . O1 . 1.9573(18) yes Cu1 . O5 . 1.9522(19) yes Cu1 . O6 . 2.311(2) yes Cu1 . N1 . 1.994(2) yes O1 . C1 . 1.286(3) yes O2 . C1 . 1.231(3) yes O3 . C4 . 1.288(3) yes O4 . C4 . 1.238(3) yes O5 . H51 . 0.841 no O5 . H52 . 0.833 no O6 . H62 . 0.839 no O6 . H61 . 0.840 no N1 . C2 . 1.479(3) yes N1 . H11 . 0.870 no N1 . H12 . 0.857 no C1 . C2 . 1.527(3) yes C2 . C3 . 1.528(3) yes C2 . H21 . 0.982 no C3 . C4 . 1.515(3) yes C3 . H31 . 0.981 no C3 . H32 . 0.962 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 1_556 Cu1 . O1 . 90.79(9) yes O3 1_556 Cu1 . O5 . 95.97(10) yes O1 . Cu1 . O5 . 172.73(8) yes O3 1_556 Cu1 . O6 . 93.53(8) yes O1 . Cu1 . O6 . 91.90(8) yes O5 . Cu1 . O6 . 90.34(8) yes O3 1_556 Cu1 . N1 . 168.17(10) yes O1 . Cu1 . N1 . 83.16(8) yes O5 . Cu1 . N1 . 89.71(8) yes O6 . Cu1 . N1 . 96.81(8) yes Cu1 . O1 . C1 . 115.71(16) yes Cu1 1_554 O3 . C4 . 115.35(16) yes Cu1 . O5 . H51 . 118.2 no Cu1 . O5 . H52 . 117.6 no H51 . O5 . H52 . 113.5 no Cu1 . O6 . H62 . 119.9 no Cu1 . O6 . H61 . 108.8 no H62 . O6 . H61 . 111.6 no Cu1 . N1 . C2 . 110.50(15) yes Cu1 . N1 . H11 . 110.5 no C2 . N1 . H11 . 110.5 no Cu1 . N1 . H12 . 107.6 no C2 . N1 . H12 . 109.6 no H11 . N1 . H12 . 108.1 no O1 . C1 . O2 . 122.9(2) yes O1 . C1 . C2 . 117.0(2) yes O2 . C1 . C2 . 120.1(2) yes C1 . C2 . N1 . 109.5(2) yes C1 . C2 . C3 . 109.3(2) yes N1 . C2 . C3 . 110.9(2) yes C1 . C2 . H21 . 110.3 no N1 . C2 . H21 . 107.5 no C3 . C2 . H21 . 109.3 no C2 . C3 . C4 . 115.0(2) yes C2 . C3 . H31 . 108.5 no C4 . C3 . H31 . 107.7 no C2 . C3 . H32 . 107.9 no C4 . C3 . H32 . 107.0 no H31 . C3 . H32 . 110.7 no C3 . C4 . O3 . 114.1(2) yes C3 . C4 . O4 . 121.8(2) yes O3 . C4 . O4 . 124.0(2) yes _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 14:57:35 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 62,X'S) H ( 61,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 14:57:35 # #LIST 16 NO END ; data_ceth01 _database_code_depnum_ccdc_archive 'CCDC 856788' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'ceth01 in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C4 H9 Cu1 N1 O6' # Given Formula = C4 H7 Cu1 N1 O5 # Dc = 1.98 Fooo = 468.00 Mu = 30.30 M = 212.65 # Found Formula = C4 H9 Cu1 N1 O6 # Dc = 2.14 FOOO = 468.00 Mu = 30.49 M = 230.66 _chemical_formula_sum 'C4 H9 Cu1 N1 O6' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 300000 _publ_section_exptl_refinement ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.423 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 170 915_ALERT_3_B Low Friedel Pair Coverage ...................... 38 Perc. 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 9 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 43 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 13 952_ALERT_5_G Reported and Calculated Lmax Values Differ by .. 6 These are caused by shading of the high-pressure cell. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 11 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 39 All 1,2 and 1,3 distances were restrained on the L-Asp ligand during refinement. Only the Cu-atom was refned with anisotropic displacement parameters, all other non-H atoms were refined isotropically. This strategy was utilised based on the low-completeness of the high-pressure data. 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.11 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 9.4817(3) _cell_length_b 10.0118(3) _cell_length_c 7.5433(7) _cell_angle_alpha 90 _cell_angle_beta 93.856(4) _cell_angle_gamma 90 _cell_volume 714.46(7) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'C 2y' 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.66 _cell_measurement_reflns_used 1800 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 2.144 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.049 # Sheldrick geometric approximatio 0.54 0.74 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.53 _exptl_absorpt_correction_T_max 0.74 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type ' synchrotron' _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 2706 _reflns_number_total 855 _diffrn_reflns_av_R_equivalents 0.044 # Number of reflections without Friedels Law is 855 # Number of reflections with Friedels Law is 465 # Theoretical number of reflections is about 1083 _diffrn_reflns_theta_min 2.962 _diffrn_reflns_theta_max 30.433 _diffrn_measured_fraction_theta_max 0.406 _diffrn_reflns_theta_full 25.564 _diffrn_measured_fraction_theta_full 0.423 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.94 _refine_diff_density_max 0.91 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 846 _refine_ls_number_restraints 39 _refine_ls_number_parameters 55 _oxford_refine_ls_R_factor_ref 0.0397 _refine_ls_wR_factor_ref 0.0873 _refine_ls_goodness_of_fit_ref 0.9221 _refine_ls_shift/su_max 0.0001454 _refine_ls_shift/su_mean 0.0000206 # The values computed from all data _oxford_reflns_number_all 846 _refine_ls_R_factor_all 0.0397 _refine_ls_wR_factor_all 0.0873 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 639 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_gt 0.0700 _refine_ls_abs_structure_Flack 0.27(3) _refine_ls_abs_structure_details 'Flack (1983), 390 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 6.83 8.61 2.63 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.23687(5) 1.00279(15) 0.87375(19) 0.0221 1.0000 Uani . . . . . . C1 C 0.3215(5) 0.7814(4) 0.6847(10) 0.0181(8) 1.0000 Uiso D U . . . . C2 C 0.2257(4) 0.8541(4) 0.5467(10) 0.0161(8) 1.0000 Uiso D U . . . . C3 C 0.3137(5) 0.9156(5) 0.4096(11) 0.0163(8) 1.0000 Uiso D U . . . . C4 C 0.2383(4) 0.9416(5) 0.2298(10) 0.0166(8) 1.0000 Uiso D U . . . . O1 O 0.3301(4) 0.8297(4) 0.8439(11) 0.0234(8) 1.0000 Uiso D U . . . . O2 O 0.3900(4) 0.6836(4) 0.6421(12) 0.0199(8) 1.0000 Uiso D U . . . . O3 O 0.3073(3) 1.0113(5) 0.1250(10) 0.0188(7) 1.0000 Uiso D U . . . . O4 O 0.1186(4) 0.8943(4) 0.1920(12) 0.0188(8) 1.0000 Uiso D U . . . . O5 O 0.1281(4) 1.1683(4) 0.8768(14) 0.0211(9) 1.0000 Uiso D . . . . . O6 O 0.4276(4) 1.1177(4) 0.7749(14) 0.0220(9) 1.0000 Uiso D . . . . . N1 N 0.1450(4) 0.9591(4) 0.6364(14) 0.0168(8) 1.0000 Uiso D U . . . . H61 H 0.4278 1.1986 0.8044 0.0269 1.0000 Uiso DR . . . . . H62 H 0.5044 1.0833 0.8149 0.0269 1.0000 Uiso DR . . . . . H51 H 0.1217 1.1941 0.9821 0.0251 1.0000 Uiso DR . . . . . H52 H 0.0470 1.1485 0.8342 0.0251 1.0000 Uiso DR . . . . . H31 H 0.3495 1.0003 0.4560 0.0195 1.0000 Uiso R . . . . . H32 H 0.3923 0.8560 0.3923 0.0195 1.0000 Uiso R . . . . . H21 H 0.1594 0.7901 0.4886 0.0193 1.0000 Uiso R . . . . . H11 H 0.1412 1.0299 0.5718 0.0201 1.0000 Uiso R . . . . . H12 H 0.0607 0.9306 0.6491 0.0201 1.0000 Uiso R . . . . . 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 Cu1 0.0163(2) 0.0141(3) 0.0351(19) -0.0005(5) -0.0040(3) 0.0025(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3115(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O3 1_556 1.968(7) yes Cu1 . O1 . 1.965(4) yes Cu1 . O5 . 1.953(4) yes Cu1 . O6 . 2.309(6) yes Cu1 . N1 . 1.987(10) yes C1 . C2 . 1.520(7) yes C1 . O1 . 1.292(8) yes C1 . O2 . 1.230(6) yes C2 . C3 . 1.504(7) yes C2 . N1 . 1.490(7) yes C2 . H21 . 0.980 no C3 . C4 . 1.513(8) yes C3 . H31 . 0.970 no C3 . H32 . 0.970 no C4 . O3 . 1.269(7) yes C4 . O4 . 1.245(5) yes O5 . H51 . 0.842 no O5 . H52 . 0.837 no O6 . H61 . 0.840 no O6 . H62 . 0.843 no N1 . H11 . 0.860 no N1 . H12 . 0.860 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 1_556 Cu1 . O1 . 91.3(3) yes O3 1_556 Cu1 . O5 . 95.6(3) yes O1 . Cu1 . O5 . 172.6(3) yes O3 1_556 Cu1 . O6 . 93.8(3) yes O1 . Cu1 . O6 . 91.97(18) yes O5 . Cu1 . O6 . 90.39(19) yes O3 1_556 Cu1 . N1 . 167.7(2) yes O1 . Cu1 . N1 . 82.9(3) yes O5 . Cu1 . N1 . 89.9(3) yes O6 . Cu1 . N1 . 97.1(3) yes C2 . C1 . O1 . 117.1(4) yes C2 . C1 . O2 . 120.3(5) yes O1 . C1 . O2 . 122.6(5) yes C1 . C2 . C3 . 109.5(4) yes C1 . C2 . N1 . 109.2(5) yes C3 . C2 . N1 . 110.4(4) yes C1 . C2 . H21 . 109.2 no C3 . C2 . H21 . 109.2 no N1 . C2 . H21 . 109.3 no C2 . C3 . C4 . 115.9(4) yes C2 . C3 . H31 . 107.9 no C4 . C3 . H31 . 107.9 no C2 . C3 . H32 . 107.9 no C4 . C3 . H32 . 107.9 no H31 . C3 . H32 . 109.5 no C3 . C4 . O3 . 114.9(4) yes C3 . C4 . O4 . 120.6(5) yes O3 . C4 . O4 . 124.5(6) yes C1 . O1 . Cu1 . 115.8(4) yes C4 . O3 . Cu1 1_554 114.8(3) yes Cu1 . O5 . H51 . 110.1 no Cu1 . O5 . H52 . 105.5 no H51 . O5 . H52 . 108.2 no Cu1 . O6 . H61 . 112.5 no Cu1 . O6 . H62 . 110.9 no H61 . O6 . H62 . 108.2 no C2 . N1 . Cu1 . 110.9(4) yes C2 . N1 . H11 . 109.1 no Cu1 . N1 . H11 . 109.1 no C2 . N1 . H12 . 109.1 no Cu1 . N1 . H12 . 109.1 no H11 . N1 . H12 . 109.5 no _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 11:57:33 # #LIST 12 BLOCK SCALE X'S CONT CU(1, U'S) CONT C(1, U[ISO]) UNTIL N(1) CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 11:57:33 # #LIST 16 DIST 0.84, 0.01 = O(6) TO H(61) DIST 0.84, 0.01 = O(6) TO H(62) ANGLE 108, 1 = H(61) TO O(6) TO H(62) DIST 0.84, 0.01 = O(5) TO H(51) DIST 0.84, 0.01 = O(5) TO H(52) ANGLE 108, 1 = H(51) TO O(5) TO H(52) DIST 1.292, 0.01 = C(1) TO O(1) DIST 1.232, 0.01 = C(1) TO O(2) DIST 1.525, 0.01 = C(1) TO C(2) DIST 1.489, 0.01 = C(2) TO N(1) DIST 1.514, 0.01 = C(2) TO C(3) DIST 1.528, 0.01 = C(3) TO C(4) DIST 1.280, 0.01 = C(4) TO O(3) DIST 1.239, 0.01 = C(4) TO O(4) ANGL 123,1= O(2) TO C(1) TO O(1) ANGL 118,1= C(2) TO C(1) TO O(1) ANGL 120,1= C(2) TO C(1) TO O(2) ANGL 109,1= C(1) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO C(1) ANGL 115,1= C(4) TO C(3) TO C(2) ANGL 124,1= O(4) TO C(4) TO O(3) ANGL 114,1= C(3) TO C(4) TO O(3) ANGL 122,1= C(3) TO C(4) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = O(1) TO C(1) VIBR .0, 0.00200 = O(2) TO C(1) VIBR .0, 0.00200 = O(3) TO C(4) VIBR .0, 0.00200 = O(4) TO C(4) VIBR .0, 0.00200 = N(1) TO C(2) VIBR .0, 0.00200 = C(1) TO C(2) VIBR .0, 0.00500 = O(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(2) VIBR .0, 0.00200 = C(2) TO C(3) VIBR .0, 0.00500 = N(1) TO C(1) VIBR .0, 0.00500 = C(3) TO C(1) VIBR .0, 0.00500 = C(3) TO N(1) VIBR .0, 0.00200 = C(3) TO C(4) VIBR .0, 0.00500 = C(4) TO C(2) VIBR .0, 0.00500 = O(3) TO C(3) VIBR .0, 0.00500 = O(4) TO C(3) VIBR .0, 0.00500 = O(4) TO O(3) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.08000 = O(1) TO C(1) U(IJ) .0, 0.08000 = O(2) TO C(1) U(IJ) .0, 0.08000 = O(3) TO C(4) U(IJ) .0, 0.08000 = O(4) TO C(4) U(IJ) .0, 0.08000 = N(1) TO C(2) U(IJ) .0, 0.04000 = C(1) TO C(2) U(IJ) .0, 0.04000 = C(2) TO C(3) U(IJ) .0, 0.04000 = C(3) TO C(4) REM THERMSIM END (DO NOT REMOVE THIS LINE) DISTANCE 0.840000 , 0.010000 = O(5) TO H(52) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 2 2 0 x . -4 -2 1 x . 2 6 3 x . -7 -1 3 x . -7 3 3 x . 2 10 4 x . 4 10 4 x . -3 3 2 x . 2 -4 0 x . data_ceth02 _database_code_depnum_ccdc_archive 'CCDC 856789' #TrackingRef '- all.cif' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'ceth02 in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C4 H9 Cu1 N1 O6' # Given Formula = C4 H7 Cu1 N1 O5 # Dc = 2.02 Fooo = 468.00 Mu = 30.95 M = 212.65 # Found Formula = C4 H9 Cu1 N1 O6 # Dc = 2.19 FOOO = 468.00 Mu = 31.15 M = 230.66 _chemical_formula_sum 'C4 H9 Cu1 N1 O6' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 850000 _publ_section_exptl_refinement ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.422 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 162 915_ALERT_3_B Low Friedel Pair Coverage ...................... 37 Perc. 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 9 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 49 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 8 952_ALERT_5_G Reported and Calculated Lmax Values Differ by .. 6 960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) .. 1 These are caused by shading of the high-pressure cell. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 11 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 37 All 1,2 and 1,3 distances were restrained on the L-Asp ligand during refinement. Only the Cu-atom was refned with anisotropic displacement parameters, all other non-H atoms were refined isotropically. This strategy was utilised based on the low-completeness of the high-pressure data. 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.18 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 9.3964(3) _cell_length_b 9.9334(4) _cell_length_c 7.5076(9) _cell_angle_alpha 90 _cell_angle_beta 93.536(6) _cell_angle_gamma 90 _cell_volume 699.41(9) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'C 2y ' 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.66 _cell_measurement_reflns_used 1748 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 2.190 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.115 # Sheldrick geometric approximatio 0.54 0.73 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.52 _exptl_absorpt_correction_T_max 0.73 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type ' synchrotron' _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 2725 _reflns_number_total 838 _diffrn_reflns_av_R_equivalents 0.039 # Number of reflections without Friedels Law is 838 # Number of reflections with Friedels Law is 456 # Theoretical number of reflections is about 1068 _diffrn_reflns_theta_min 2.987 _diffrn_reflns_theta_max 30.509 _diffrn_measured_fraction_theta_max 0.403 _diffrn_reflns_theta_full 25.017 _diffrn_measured_fraction_theta_full 0.422 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.41 _refine_diff_density_max 0.48 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 834 _refine_ls_number_restraints 37 _refine_ls_number_parameters 55 _oxford_refine_ls_R_factor_ref 0.0417 _refine_ls_wR_factor_ref 0.0565 _refine_ls_goodness_of_fit_ref 0.8356 _refine_ls_shift/su_max 0.0002209 _refine_ls_shift/su_mean 0.0000476 # The values computed from all data _oxford_reflns_number_all 834 _refine_ls_R_factor_all 0.0417 _refine_ls_wR_factor_all 0.0565 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 486 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_gt 0.0514 _refine_ls_abs_structure_Flack 0.23(2) _refine_ls_abs_structure_details 'Flack (1983), 382 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.68P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.23773(4) 1.00347(13) 0.87110(17) 0.0189 1.0000 Uani . . . . . . C1 C 0.3222(4) 0.7808(4) 0.6852(9) 0.0141(8) 1.0000 Uiso D U . . . . C2 C 0.2252(3) 0.8527(4) 0.5484(10) 0.0141(7) 1.0000 Uiso D U . . . . C3 C 0.3152(4) 0.9151(3) 0.4089(11) 0.0153(8) 1.0000 Uiso D U . . . . C4 C 0.2390(3) 0.9421(5) 0.2281(10) 0.0134(7) 1.0000 Uiso D U . . . . O1 O 0.3311(3) 0.8283(3) 0.8453(11) 0.0222(7) 1.0000 Uiso D U . . . . O2 O 0.3896(2) 0.6799(3) 0.6421(10) 0.0154(6) 1.0000 Uiso D U . . . . O3 O 0.3099(2) 1.0138(4) 0.1246(10) 0.0162(6) 1.0000 Uiso D U . . . . O4 O 0.1193(2) 0.8936(3) 0.1851(10) 0.0150(6) 1.0000 Uiso D U . . . . O5 O 0.1277(3) 1.1681(3) 0.8761(11) 0.0212(7) 1.0000 Uiso . . . . . . O6 O 0.4268(3) 1.1182(3) 0.7691(13) 0.0216(7) 1.0000 Uiso . . . . . . N1 N 0.1430(3) 0.9581(3) 0.6406(13) 0.0120(7) 1.0000 Uiso D U . . . . H31 H 0.3517 1.0021 0.4640 0.0201 1.0000 Uiso R . . . . . H32 H 0.4006 0.8577 0.4023 0.0201 1.0000 Uiso R . . . . . H21 H 0.1627 0.7871 0.4920 0.0222 1.0000 Uiso R . . . . . H11 H 0.1392 1.0282 0.5698 0.0207 1.0000 Uiso R . . . . . H12 H 0.0585 0.9285 0.6496 0.0207 1.0000 Uiso R . . . . . H61 H 0.4279 1.2018 0.7843 0.0260 1.0000 Uiso R . . . . . H62 H 0.5055 1.0874 0.8104 0.0260 1.0000 Uiso R . . . . . H51 H 0.1304 1.1914 0.9838 0.0350 1.0000 Uiso R . . . . . H52 H 0.0420 1.1597 0.8398 0.0350 1.0000 Uiso R . . . . . 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 Cu1 0.0163(3) 0.0136(2) 0.027(2) 0.0016(6) -0.0014(4) 0.0026(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2530(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O3 1_556 1.984(7) yes Cu1 . O1 . 1.964(3) yes Cu1 . O5 . 1.936(3) yes Cu1 . O6 . 2.283(5) yes Cu1 . N1 . 1.949(8) yes C1 . C2 . 1.510(6) yes C1 . O1 . 1.289(8) yes C1 . O2 . 1.239(5) yes C2 . C3 . 1.518(7) yes C2 . N1 . 1.496(6) yes C2 . H21 . 0.958 no C3 . C4 . 1.518(8) yes C3 . H31 . 1.010 no C3 . H32 . 0.988 no C4 . O3 . 1.272(6) yes C4 . O4 . 1.248(4) yes O5 . H51 . 0.840 no O5 . H52 . 0.838 no O6 . H61 . 0.838 no O6 . H62 . 0.841 no N1 . H11 . 0.875 no N1 . H12 . 0.853 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 1_556 Cu1 . O1 . 90.7(2) yes O3 1_556 Cu1 . O5 . 95.1(3) yes O1 . Cu1 . O5 . 173.0(2) yes O3 1_556 Cu1 . O6 . 93.9(2) yes O1 . Cu1 . O6 . 92.73(13) yes O5 . Cu1 . O6 . 90.70(14) yes O3 1_556 Cu1 . N1 . 166.98(18) yes O1 . Cu1 . N1 . 83.7(2) yes O5 . Cu1 . N1 . 89.8(2) yes O6 . Cu1 . N1 . 98.0(3) yes C2 . C1 . O1 . 117.6(4) yes C2 . C1 . O2 . 120.1(5) yes O1 . C1 . O2 . 122.3(5) yes C1 . C2 . C3 . 108.9(3) yes C1 . C2 . N1 . 108.9(5) yes C3 . C2 . N1 . 111.0(4) yes C1 . C2 . H21 . 107.9 no C3 . C2 . H21 . 109.0 no N1 . C2 . H21 . 111.1 no C2 . C3 . C4 . 115.9(3) yes C2 . C3 . H31 . 104.9 no C4 . C3 . H31 . 110.2 no C2 . C3 . H32 . 106.7 no C4 . C3 . H32 . 113.4 no H31 . C3 . H32 . 104.9 no C3 . C4 . O3 . 114.2(3) yes C3 . C4 . O4 . 122.0(5) yes O3 . C4 . O4 . 123.8(5) yes C1 . O1 . Cu1 . 114.4(4) yes C4 . O3 . Cu1 1_554 113.3(3) yes Cu1 . O5 . H51 . 105.5 no Cu1 . O5 . H52 . 114.4 no H51 . O5 . H52 . 108.2 no Cu1 . O6 . H61 . 116.9 no Cu1 . O6 . H62 . 112.3 no H61 . O6 . H62 . 107.9 no C2 . N1 . Cu1 . 110.6(3) yes C2 . N1 . H11 . 106.2 no Cu1 . N1 . H11 . 110.7 no C2 . N1 . H12 . 107.7 no Cu1 . N1 . H12 . 112.7 no H11 . N1 . H12 . 108.6 no _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 14:04:57 # #LIST 12 BLOCK SCALE X'S CONT CU(1, U'S) CONT C(1, U[ISO]) UNTIL N(1) CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 14:04:57 # #LIST 16 DIST 1.292, 0.01 = C(1) TO O(1) DIST 1.232, 0.01 = C(1) TO O(2) DIST 1.525, 0.01 = C(1) TO C(2) DIST 1.489, 0.01 = C(2) TO N(1) DIST 1.514, 0.01 = C(2) TO C(3) DIST 1.528, 0.01 = C(3) TO C(4) DIST 1.280, 0.01 = C(4) TO O(3) DIST 1.239, 0.01 = C(4) TO O(4) ANGL 123,1= O(2) TO C(1) TO O(1) ANGL 118,1= C(2) TO C(1) TO O(1) ANGL 120,1= C(2) TO C(1) TO O(2) ANGL 109,1= C(1) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO C(1) ANGL 115,1= C(4) TO C(3) TO C(2) ANGL 124,1= O(4) TO C(4) TO O(3) ANGL 114,1= C(3) TO C(4) TO O(3) ANGL 122,1= C(3) TO C(4) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = O(1) TO C(1) VIBR .0, 0.00200 = O(2) TO C(1) VIBR .0, 0.00200 = O(3) TO C(4) VIBR .0, 0.00200 = O(4) TO C(4) VIBR .0, 0.00200 = N(1) TO C(2) VIBR .0, 0.00200 = C(1) TO C(2) VIBR .0, 0.00500 = O(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(2) VIBR .0, 0.00200 = C(2) TO C(3) VIBR .0, 0.00500 = N(1) TO C(1) VIBR .0, 0.00500 = C(3) TO C(1) VIBR .0, 0.00500 = C(3) TO N(1) VIBR .0, 0.00200 = C(3) TO C(4) VIBR .0, 0.00500 = C(4) TO C(2) VIBR .0, 0.00500 = O(3) TO C(3) VIBR .0, 0.00500 = O(4) TO C(3) VIBR .0, 0.00500 = O(4) TO O(3) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.08000 = O(1) TO C(1) U(IJ) .0, 0.08000 = O(2) TO C(1) U(IJ) .0, 0.08000 = O(3) TO C(4) U(IJ) .0, 0.08000 = O(4) TO C(4) U(IJ) .0, 0.08000 = N(1) TO C(2) U(IJ) .0, 0.04000 = C(1) TO C(2) U(IJ) .0, 0.04000 = C(2) TO C(3) U(IJ) .0, 0.04000 = C(3) TO C(4) REM THERMSIM END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 2 6 3 x . 8 0 3 x . -11 -7 3 x . 7 9 4 x . data_ceth03 _database_code_depnum_ccdc_archive 'CCDC 856790' #TrackingRef '- all.cif' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'ceth03 in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C4 H9 Cu1 N1 O6' # Given Formula = C4 H7 Cu1 N1 O5 # Dc = 2.08 Fooo = 468.00 Mu = 31.86 M = 212.65 # Found Formula = C4 H9 Cu1 N1 O6 # Dc = 2.25 FOOO = 468.00 Mu = 32.05 M = 230.66 _chemical_formula_sum 'C4 H9 Cu1 N1 O6' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 1840000 _publ_section_exptl_refinement ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.421 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 160 915_ALERT_3_B Low Friedel Pair Coverage ...................... 37 Perc. 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 9 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 51 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 8 952_ALERT_5_G Reported and Calculated Lmax Values Differ by .. 6 These are caused by shading of the high-pressure cell. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 11 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 37 All 1,2 and 1,3 distances were restrained on the L-Asp ligand during refinement. Only the Cu-atom was refned with anisotropic displacement parameters, all other non-H atoms were refined isotropically. This strategy was utilised based on the low-completeness of the high-pressure data. 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.26 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 9.2843(3) _cell_length_b 9.8358(4) _cell_length_c 7.4532(7) _cell_angle_alpha 90 _cell_angle_beta 93.071(5) _cell_angle_gamma 90 _cell_volume 679.64(7) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'C 2y ' 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.66 _cell_measurement_reflns_used 1650 _cell_measurement_theta_min 4 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 2.254 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.205 # Sheldrick geometric approximatio 0.53 0.73 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 0.73 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type ' synchrotron' _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 2659 _reflns_number_total 810 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections without Friedels Law is 810 # Number of reflections with Friedels Law is 441 # Theoretical number of reflections is about 1038 _diffrn_reflns_theta_min 3.019 _diffrn_reflns_theta_max 30.517 _diffrn_measured_fraction_theta_max 0.400 _diffrn_reflns_theta_full 25.024 _diffrn_measured_fraction_theta_full 0.421 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.51 _refine_diff_density_max 0.50 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 807 _refine_ls_number_restraints 37 _refine_ls_number_parameters 55 _oxford_refine_ls_R_factor_ref 0.0407 _refine_ls_wR_factor_ref 0.0676 _refine_ls_goodness_of_fit_ref 0.9613 _refine_ls_shift/su_max 0.0001762 _refine_ls_shift/su_mean 0.0000261 # The values computed from all data _oxford_reflns_number_all 807 _refine_ls_R_factor_all 0.0407 _refine_ls_wR_factor_all 0.0676 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 626 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_gt 0.0596 _refine_ls_abs_structure_Flack 0.27(3) _refine_ls_abs_structure_details 'Flack (1983), 369 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 1.33P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.23885(4) 1.00371(13) 0.8696(2) 0.0212 1.0000 Uani . . . . . . C1 C 0.3222(4) 0.7773(4) 0.6839(11) 0.0157(8) 1.0000 Uiso D U . . . . C2 C 0.2241(4) 0.8502(4) 0.5450(11) 0.0152(8) 1.0000 Uiso D U . . . . C3 C 0.3161(4) 0.9145(4) 0.4052(11) 0.0141(8) 1.0000 Uiso D U . . . . C4 C 0.2419(4) 0.9417(5) 0.2217(10) 0.0120(7) 1.0000 Uiso D U . . . . O1 O 0.3344(3) 0.8279(4) 0.8448(12) 0.0211(8) 1.0000 Uiso D U . . . . O2 O 0.3903(3) 0.6752(3) 0.6416(12) 0.0162(7) 1.0000 Uiso D U . . . . O3 O 0.3132(3) 1.0157(4) 0.1180(10) 0.0155(6) 1.0000 Uiso D U . . . . O4 O 0.1210(3) 0.8924(3) 0.1800(11) 0.0150(7) 1.0000 Uiso D U . . . . O5 O 0.1266(3) 1.1693(3) 0.8772(13) 0.0181(8) 1.0000 Uiso . . . . . . O6 O 0.4290(3) 1.1187(3) 0.7629(14) 0.0200(8) 1.0000 Uiso . . . . . . N1 N 0.1417(3) 0.9561(4) 0.6411(14) 0.0137(8) 1.0000 Uiso D U . . . . H31 H 0.3517 1.0006 0.4533 0.0174 1.0000 Uiso R . . . . . H32 H 0.3974 0.8541 0.3888 0.0174 1.0000 Uiso R . . . . . H21 H 0.1572 0.7850 0.4867 0.0184 1.0000 Uiso R . . . . . H11 H 0.1335 1.0275 0.5747 0.0176 1.0000 Uiso R . . . . . H12 H 0.0572 0.9248 0.6596 0.0176 1.0000 Uiso R . . . . . H61 H 0.4198 1.1993 0.7982 0.0253 1.0000 Uiso R . . . . . H62 H 0.5134 1.0931 0.7929 0.0253 1.0000 Uiso R . . . . . H51 H 0.1374 1.2403 0.9381 0.0229 1.0000 Uiso R . . . . . H52 H 0.0404 1.1645 0.8399 0.0229 1.0000 Uiso R . . . . . 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 Cu1 0.0155(2) 0.0130(3) 0.035(3) 0.0000(7) -0.0032(4) 0.0023(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2591(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O3 1_556 1.945(7) yes Cu1 . O4 1_556 2.832(7) yes Cu1 . O1 . 1.957(4) yes Cu1 . O5 . 1.936(3) yes Cu1 . O6 . 2.275(5) yes Cu1 . N1 . 1.942(9) yes C1 . C2 . 1.522(6) yes C1 . O1 . 1.298(8) yes C1 . O2 . 1.237(5) yes C2 . C3 . 1.520(7) yes C2 . N1 . 1.497(7) yes C2 . H21 . 0.978 no C3 . C4 . 1.522(8) yes C3 . H31 . 0.970 no C3 . H32 . 0.973 no C4 . O3 . 1.273(6) yes C4 . O4 . 1.246(4) yes O5 . H51 . 0.835 no O5 . H52 . 0.835 no O6 . H61 . 0.841 no O6 . H62 . 0.842 no N1 . H11 . 0.861 no N1 . H12 . 0.861 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 1_556 Cu1 . O4 1_556 51.56(15) yes O3 1_556 Cu1 . O1 . 90.2(3) yes O4 1_556 Cu1 . O1 . 86.1(2) yes O3 1_556 Cu1 . O5 . 94.9(3) yes O4 1_556 Cu1 . O5 . 94.0(3) yes O1 . Cu1 . O5 . 173.6(2) yes O3 1_556 Cu1 . O6 . 93.5(3) yes O4 1_556 Cu1 . O6 . 144.9(3) yes O1 . Cu1 . O6 . 92.43(15) yes O5 . Cu1 . O6 . 91.20(16) yes O3 1_556 Cu1 . N1 . 167.0(2) yes O4 1_556 Cu1 . N1 . 116.2(2) yes O1 . Cu1 . N1 . 84.0(2) yes O5 . Cu1 . N1 . 90.2(3) yes O6 . Cu1 . N1 . 98.4(3) yes C2 . C1 . O1 . 117.9(4) yes C2 . C1 . O2 . 120.4(5) yes O1 . C1 . O2 . 121.8(5) yes C1 . C2 . C3 . 108.9(3) yes C1 . C2 . N1 . 107.8(5) yes C3 . C2 . N1 . 111.0(4) yes C1 . C2 . H21 . 109.6 no C3 . C2 . H21 . 109.6 no N1 . C2 . H21 . 109.9 no C2 . C3 . C4 . 116.4(3) yes C2 . C3 . H31 . 107.6 no C4 . C3 . H31 . 107.9 no C2 . C3 . H32 . 107.5 no C4 . C3 . H32 . 108.1 no H31 . C3 . H32 . 109.1 no C3 . C4 . O3 . 114.9(3) yes C3 . C4 . O4 . 120.9(5) yes O3 . C4 . O4 . 124.2(5) yes C1 . O1 . Cu1 . 114.1(4) yes C4 . O3 . Cu1 1_554 111.9(3) yes C4 . O4 . Cu1 1_554 70.8(4) yes Cu1 . O5 . H51 . 132.1 no Cu1 . O5 . H52 . 116.8 no H51 . O5 . H52 . 108.2 no Cu1 . O6 . H61 . 105.4 no Cu1 . O6 . H62 . 119.1 no H61 . O6 . H62 . 107.9 no C2 . N1 . Cu1 . 111.2(3) yes C2 . N1 . H11 . 108.9 no Cu1 . N1 . H11 . 109.3 no C2 . N1 . H12 . 108.7 no Cu1 . N1 . H12 . 109.3 no H11 . N1 . H12 . 109.3 no _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 14:09:05 # #LIST 12 BLOCK SCALE X'S CONT CU(1, U'S) CONT C(1, U[ISO]) UNTIL N(1) CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 14:09:05 # #LIST 16 DIST 1.292, 0.01 = C(1) TO O(1) DIST 1.232, 0.01 = C(1) TO O(2) DIST 1.525, 0.01 = C(1) TO C(2) DIST 1.489, 0.01 = C(2) TO N(1) DIST 1.514, 0.01 = C(2) TO C(3) DIST 1.528, 0.01 = C(3) TO C(4) DIST 1.280, 0.01 = C(4) TO O(3) DIST 1.239, 0.01 = C(4) TO O(4) ANGL 123,1= O(2) TO C(1) TO O(1) ANGL 118,1= C(2) TO C(1) TO O(1) ANGL 120,1= C(2) TO C(1) TO O(2) ANGL 109,1= C(1) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO C(1) ANGL 115,1= C(4) TO C(3) TO C(2) ANGL 124,1= O(4) TO C(4) TO O(3) ANGL 114,1= C(3) TO C(4) TO O(3) ANGL 122,1= C(3) TO C(4) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = O(1) TO C(1) VIBR .0, 0.00200 = O(2) TO C(1) VIBR .0, 0.00200 = O(3) TO C(4) VIBR .0, 0.00200 = O(4) TO C(4) VIBR .0, 0.00200 = N(1) TO C(2) VIBR .0, 0.00200 = C(1) TO C(2) VIBR .0, 0.00500 = O(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(2) VIBR .0, 0.00200 = C(2) TO C(3) VIBR .0, 0.00500 = N(1) TO C(1) VIBR .0, 0.00500 = C(3) TO C(1) VIBR .0, 0.00500 = C(3) TO N(1) VIBR .0, 0.00200 = C(3) TO C(4) VIBR .0, 0.00500 = C(4) TO C(2) VIBR .0, 0.00500 = O(3) TO C(3) VIBR .0, 0.00500 = O(4) TO C(3) VIBR .0, 0.00500 = O(4) TO O(3) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.08000 = O(1) TO C(1) U(IJ) .0, 0.08000 = O(2) TO C(1) U(IJ) .0, 0.08000 = O(3) TO C(4) U(IJ) .0, 0.08000 = O(4) TO C(4) U(IJ) .0, 0.08000 = N(1) TO C(2) U(IJ) .0, 0.04000 = C(1) TO C(2) U(IJ) .0, 0.04000 = C(2) TO C(3) U(IJ) .0, 0.04000 = C(3) TO C(4) REM THERMSIM END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details -2 0 1 x . -3 13 3 x . -3 3 2 x . data_ceth04 _database_code_depnum_ccdc_archive 'CCDC 856791' #TrackingRef '- all.cif' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'ceth04 in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C4 H9 Cu1 N1 O6' # Given Formula = C4 H7 Cu1 N1 O6 # Dc = 2.32 Fooo = 468.00 Mu = 33.34 M = 228.65 # Found Formula = C4 H9 Cu1 N1 O6 # Dc = 2.35 FOOO = 468.00 Mu = 33.35 M = 230.66 _chemical_formula_sum 'C4 H9 Cu1 N1 O6' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 3490000 _publ_section_exptl_refinement ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.433 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 149 915_ALERT_3_B Low Friedel Pair Coverage ...................... 37 Perc. 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 12 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 48 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 3 952_ALERT_5_G Reported and Calculated Lmax Values Differ by .. 6 These are caused by shading of the high-pressure cell. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 11 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 37 All 1,2 and 1,3 distances were restrained on the L-Asp ligand during refinement. Only the Cu-atom was refned with anisotropic displacement parameters, all other non-H atoms were refined isotropically. This strategy was utilised based on the low-completeness of the high-pressure data. 033_ALERT_4_C Flack x Parameter Value Deviates from Zero ..... 0.310 The hand is known. 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.48 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 9.1425(9) _cell_length_b 9.7138(11) _cell_length_c 7.361(2) _cell_angle_alpha 90 _cell_angle_beta 92.265(16) _cell_angle_gamma 90 _cell_volume 653.2(2) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall ? 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.66 _cell_measurement_reflns_used 1511 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 2.345 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.335 # Sheldrick geometric approximatio 0.51 0.72 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.72 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type ' synchrotron' _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 2568 _reflns_number_total 786 _diffrn_reflns_av_R_equivalents 0.041 # Number of reflections without Friedels Law is 786 # Number of reflections with Friedels Law is 436 # Theoretical number of reflections is about 996 _diffrn_reflns_theta_min 3.061 _diffrn_reflns_theta_max 30.492 _diffrn_measured_fraction_theta_max 0.413 _diffrn_reflns_theta_full 25.308 _diffrn_measured_fraction_theta_full 0.433 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -1.20 _refine_diff_density_max 0.68 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 786 _refine_ls_number_restraints 37 _refine_ls_number_parameters 55 _oxford_refine_ls_R_factor_ref 0.0548 _refine_ls_wR_factor_ref 0.0916 _refine_ls_goodness_of_fit_ref 0.9333 _refine_ls_shift/su_max 0.0001070 _refine_ls_shift/su_mean 0.0000204 # The values computed from all data _oxford_reflns_number_all 786 _refine_ls_R_factor_all 0.0548 _refine_ls_wR_factor_all 0.0916 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 595 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_gt 0.0667 _refine_ls_abs_structure_Flack 0.31(4) _refine_ls_abs_structure_details 'Flack (1983), 350 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.70P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.24035(7) 1.00462(17) 0.8665(3) 0.0286 1.0000 Uani . . . . . . C1 C 0.3229(7) 0.7738(6) 0.6822(13) 0.0150(10) 1.0000 Uiso D U . . . . C2 C 0.2235(6) 0.8461(5) 0.5418(13) 0.0141(9) 1.0000 Uiso D U . . . . C3 C 0.3183(6) 0.9133(6) 0.4019(14) 0.0140(10) 1.0000 Uiso D U . . . . C4 C 0.2451(5) 0.9427(7) 0.2165(13) 0.0103(9) 1.0000 Uiso D U . . . . O1 O 0.3368(5) 0.8280(5) 0.8417(15) 0.0184(10) 1.0000 Uiso D U . . . . O2 O 0.3903(5) 0.6693(5) 0.6403(17) 0.0161(10) 1.0000 Uiso D U . . . . O3 O 0.3172(4) 1.0194(5) 0.1106(13) 0.0141(9) 1.0000 Uiso D U . . . . O4 O 0.1239(4) 0.8916(5) 0.1761(15) 0.0129(9) 1.0000 Uiso D U . . . . O5 O 0.1264(5) 1.1707(5) 0.879(2) 0.0165(12) 1.0000 Uiso . . . . . . O6 O 0.4302(5) 1.1215(5) 0.754(2) 0.0198(12) 1.0000 Uiso . . . . . . N1 N 0.1399(5) 0.9526(5) 0.6437(17) 0.0140(10) 1.0000 Uiso D U . . . . H31 H 0.3530 1.0003 0.4530 0.0168 1.0000 Uiso R . . . . . H32 H 0.4012 0.8532 0.3846 0.0168 1.0000 Uiso R . . . . . H21 H 0.1563 0.7802 0.4833 0.0170 1.0000 Uiso R . . . . . H11 H 0.1282 1.0246 0.5766 0.0168 1.0000 Uiso R . . . . . H12 H 0.0557 0.9196 0.6683 0.0168 1.0000 Uiso R . . . . . H61 H 0.4190 1.2004 0.7982 0.0248 1.0000 Uiso R . . . . . H62 H 0.5147 1.0948 0.7877 0.0248 1.0000 Uiso R . . . . . H51 H 0.1516 1.2364 0.9474 0.0206 1.0000 Uiso R . . . . . H52 H 0.0380 1.1750 0.8452 0.0206 1.0000 Uiso R . . . . . 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 Cu1 0.0153(3) 0.0123(4) 0.058(3) -0.0032(10) -0.0055(6) 0.0030(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2492(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O4 1_556 2.779(10) yes Cu1 . O3 1_556 1.909(9) yes Cu1 . O1 . 1.941(5) yes Cu1 . O5 . 1.924(5) yes Cu1 . O6 . 2.258(8) yes Cu1 . N1 . 1.916(11) yes C1 . C2 . 1.521(7) yes C1 . O1 . 1.289(9) yes C1 . O2 . 1.233(6) yes C2 . C3 . 1.519(8) yes C2 . N1 . 1.504(8) yes C2 . H21 . 0.975 no C3 . C4 . 1.523(8) yes C3 . H31 . 0.973 no C3 . H32 . 0.970 no C4 . O3 . 1.279(7) yes C4 . O4 . 1.240(5) yes O5 . H51 . 0.838 no O5 . H52 . 0.838 no O6 . H61 . 0.840 no O6 . H62 . 0.842 no N1 . H11 . 0.861 no N1 . H12 . 0.860 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 1_556 Cu1 . O3 1_556 52.9(2) yes O4 1_556 Cu1 . O1 . 85.3(3) yes O3 1_556 Cu1 . O1 . 90.2(3) yes O4 1_556 Cu1 . O5 . 93.8(4) yes O3 1_556 Cu1 . O5 . 94.1(4) yes O1 . Cu1 . O5 . 173.9(2) yes O4 1_556 Cu1 . O6 . 145.5(4) yes O3 1_556 Cu1 . O6 . 92.7(4) yes O1 . Cu1 . O6 . 92.9(2) yes O5 . Cu1 . O6 . 91.3(3) yes O4 1_556 Cu1 . N1 . 114.3(3) yes O3 1_556 Cu1 . N1 . 166.4(3) yes O1 . Cu1 . N1 . 83.7(3) yes O5 . Cu1 . N1 . 91.2(4) yes O6 . Cu1 . N1 . 99.7(4) yes C2 . C1 . O1 . 117.7(5) yes C2 . C1 . O2 . 120.1(6) yes O1 . C1 . O2 . 122.2(6) yes C1 . C2 . C3 . 108.5(5) yes C1 . C2 . N1 . 106.3(5) yes C3 . C2 . N1 . 110.9(5) yes C1 . C2 . H21 . 110.2 no C3 . C2 . H21 . 110.4 no N1 . C2 . H21 . 110.4 no C2 . C3 . C4 . 116.5(4) yes C2 . C3 . H31 . 107.3 no C4 . C3 . H31 . 107.9 no C2 . C3 . H32 . 107.5 no C4 . C3 . H32 . 108.2 no H31 . C3 . H32 . 109.2 no C3 . C4 . O3 . 115.9(4) yes C3 . C4 . O4 . 119.8(6) yes O3 . C4 . O4 . 124.3(6) yes C1 . O1 . Cu1 . 114.7(5) yes C4 . O3 . Cu1 1_554 110.5(4) yes C4 . O4 . Cu1 1_554 70.8(5) yes Cu1 . O5 . H51 . 122.1 no Cu1 . O5 . H52 . 123.1 no H51 . O5 . H52 . 112.3 no Cu1 . O6 . H61 . 102.1 no Cu1 . O6 . H62 . 116.5 no H61 . O6 . H62 . 106.9 no C2 . N1 . Cu1 . 111.9(4) yes C2 . N1 . H11 . 109.1 no Cu1 . N1 . H11 . 108.7 no C2 . N1 . H12 . 109.0 no Cu1 . N1 . H12 . 108.7 no H11 . N1 . H12 . 109.3 no _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 14:16:02 # #LIST 12 BLOCK SCALE X'S CONT CU(1, U'S) CONT C(1, U[ISO]) UNTIL N(1) CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 14:16:02 # #LIST 16 DIST 1.292, 0.01 = C(1) TO O(1) DIST 1.232, 0.01 = C(1) TO O(2) DIST 1.525, 0.01 = C(1) TO C(2) DIST 1.489, 0.01 = C(2) TO N(1) DIST 1.514, 0.01 = C(2) TO C(3) DIST 1.528, 0.01 = C(3) TO C(4) DIST 1.280, 0.01 = C(4) TO O(3) DIST 1.239, 0.01 = C(4) TO O(4) ANGL 123,1= O(2) TO C(1) TO O(1) ANGL 118,1= C(2) TO C(1) TO O(1) ANGL 120,1= C(2) TO C(1) TO O(2) ANGL 109,1= C(1) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO C(1) ANGL 115,1= C(4) TO C(3) TO C(2) ANGL 124,1= O(4) TO C(4) TO O(3) ANGL 114,1= C(3) TO C(4) TO O(3) ANGL 122,1= C(3) TO C(4) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = O(1) TO C(1) VIBR .0, 0.00200 = O(2) TO C(1) VIBR .0, 0.00200 = O(3) TO C(4) VIBR .0, 0.00200 = O(4) TO C(4) VIBR .0, 0.00200 = N(1) TO C(2) VIBR .0, 0.00200 = C(1) TO C(2) VIBR .0, 0.00500 = O(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(2) VIBR .0, 0.00200 = C(2) TO C(3) VIBR .0, 0.00500 = N(1) TO C(1) VIBR .0, 0.00500 = C(3) TO C(1) VIBR .0, 0.00500 = C(3) TO N(1) VIBR .0, 0.00200 = C(3) TO C(4) VIBR .0, 0.00500 = C(4) TO C(2) VIBR .0, 0.00500 = O(3) TO C(3) VIBR .0, 0.00500 = O(4) TO C(3) VIBR .0, 0.00500 = O(4) TO O(3) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.08000 = O(1) TO C(1) U(IJ) .0, 0.08000 = O(2) TO C(1) U(IJ) .0, 0.08000 = O(3) TO C(4) U(IJ) .0, 0.08000 = O(4) TO C(4) U(IJ) .0, 0.08000 = N(1) TO C(2) U(IJ) .0, 0.04000 = C(1) TO C(2) U(IJ) .0, 0.04000 = C(2) TO C(3) U(IJ) .0, 0.04000 = C(3) TO C(4) REM THERMSIM END (DO NOT REMOVE THIS LINE) END ; data_ceth05 _database_code_depnum_ccdc_archive 'CCDC 856792' #TrackingRef '- all.cif' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'ceth05 in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C4 H9 Cu1 N1 O6' # Given Formula = C4 H7 Cu1 N1 O6 # Dc = 2.39 Fooo = 468.00 Mu = 34.25 M = 228.65 # Found Formula = C4 H9 Cu1 N1 O6 # Dc = 2.41 FOOO = 468.00 Mu = 34.26 M = 230.66 _chemical_formula_sum 'C4 H9 Cu1 N1 O6' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 4920000 _publ_section_exptl_refinement ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.416 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 165 915_ALERT_3_B Low Friedel Pair Coverage ...................... 36 Perc. 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 9 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 57 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 6 952_ALERT_5_G Reported and Calculated Lmax Values Differ by .. 6 These are caused by shading of the high-pressure cell. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 11 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 37 All 1,2 and 1,3 distances were restrained on the L-Asp ligand during refinement. Only the Cu-atom was refned with anisotropic displacement parameters, all other non-H atoms were refined isotropically. This strategy was utilised based on the low-completeness of the high-pressure data. 314_ALERT_2_C Check Small Angle for H2O: Metal-O6 -H61 91.95 Deg. Though the angle subtended through the metal-O-H is quite small, the H-bonding interaction O6-H61...O4 that this water molecule makes is quite normal (148 degrees). 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.41 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 9.0447(5) _cell_length_b 9.6337(7) _cell_length_c 7.3016(14) _cell_angle_alpha 90 _cell_angle_beta 91.765(10) _cell_angle_gamma 90 _cell_volume 635.92(14) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'C 2y' 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.66 _cell_measurement_reflns_used 1453 _cell_measurement_theta_min 4 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 2.409 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.426 # Sheldrick geometric approximatio 0.50 0.71 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.71 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type ' synchrotron' _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 2538 _reflns_number_total 728 _diffrn_reflns_av_R_equivalents 0.042 # Number of reflections without Friedels Law is 728 # Number of reflections with Friedels Law is 406 # Theoretical number of reflections is about 964 _diffrn_reflns_theta_min 3.090 _diffrn_reflns_theta_max 30.434 _diffrn_measured_fraction_theta_max 0.397 _diffrn_reflns_theta_full 25.260 _diffrn_measured_fraction_theta_full 0.416 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -13 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.31 _refine_diff_density_max 0.32 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 728 _refine_ls_number_restraints 37 _refine_ls_number_parameters 55 _oxford_refine_ls_R_factor_ref 0.0348 _refine_ls_wR_factor_ref 0.0615 _refine_ls_goodness_of_fit_ref 0.8689 _refine_ls_shift/su_max 0.0001031 _refine_ls_shift/su_mean 0.0000180 # The values computed from all data _oxford_reflns_number_all 728 _refine_ls_R_factor_all 0.0348 _refine_ls_wR_factor_all 0.0615 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 566 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_gt 0.0539 _refine_ls_abs_structure_Flack 0.29(3) _refine_ls_abs_structure_details 'Flack (1983), 322 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 4.85 5.43 1.24 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.24128(6) 1.00711(14) 0.8642(2) 0.0167 1.0000 Uani . . . . . . C1 C 0.3236(5) 0.7724(4) 0.6821(10) 0.0131(8) 1.0000 Uiso D U . . . . C2 C 0.2237(5) 0.8457(4) 0.5422(11) 0.0139(8) 1.0000 Uiso D U . . . . C3 C 0.3200(5) 0.9154(5) 0.4027(11) 0.0124(8) 1.0000 Uiso D U . . . . C4 C 0.2473(5) 0.9453(5) 0.2156(10) 0.0125(8) 1.0000 Uiso D U . . . . O1 O 0.3403(4) 0.8296(4) 0.8405(11) 0.0171(8) 1.0000 Uiso D U . . . . O2 O 0.3913(4) 0.6666(3) 0.6374(12) 0.0140(7) 1.0000 Uiso D U . . . . O3 O 0.3210(3) 1.0242(4) 0.1115(10) 0.0148(8) 1.0000 Uiso D U . . . . O4 O 0.1255(4) 0.8930(4) 0.1691(12) 0.0141(7) 1.0000 Uiso D U . . . . O5 O 0.1267(4) 1.1742(4) 0.8709(13) 0.0164(9) 1.0000 Uiso . . . . . . O6 O 0.4303(4) 1.1261(4) 0.7484(13) 0.0181(9) 1.0000 Uiso . . . . . . N1 N 0.1359(4) 0.9528(4) 0.6383(14) 0.0136(8) 1.0000 Uiso D U . . . . H31 H 0.3530 1.0033 0.4544 0.0155 1.0000 Uiso R . . . . . H32 H 0.4049 0.8562 0.3841 0.0155 1.0000 Uiso R . . . . . H21 H 0.1576 0.7785 0.4801 0.0172 1.0000 Uiso R . . . . . H11 H 0.1242 1.0240 0.5682 0.0170 1.0000 Uiso R . . . . . H12 H 0.0511 0.9189 0.6633 0.0170 1.0000 Uiso R . . . . . H61 H 0.4141 1.1947 0.8154 0.0229 1.0000 Uiso R . . . . . H62 H 0.5119 1.0978 0.7919 0.0229 1.0000 Uiso R . . . . . H51 H 0.1428 1.2452 0.9349 0.0208 1.0000 Uiso R . . . . . H52 H 0.0381 1.1781 0.8341 0.0208 1.0000 Uiso R . . . . . 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 Cu1 0.0144(2) 0.0117(2) 0.0238(18) 0.0001(6) -0.0033(3) 0.0030(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2645(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O4 1_556 2.721(8) yes Cu1 . O3 1_556 1.931(7) yes Cu1 . O1 . 1.940(4) yes Cu1 . O5 . 1.915(4) yes Cu1 . O6 . 2.245(6) yes Cu1 . N1 . 1.951(8) yes C1 . C2 . 1.517(6) yes C1 . O1 . 1.286(8) yes C1 . O2 . 1.238(5) yes C2 . C3 . 1.517(7) yes C2 . N1 . 1.491(7) yes C2 . H21 . 0.983 no C3 . C4 . 1.525(8) yes C3 . H31 . 0.971 no C3 . H32 . 0.970 no C4 . O3 . 1.277(6) yes C4 . O4 . 1.248(5) yes O5 . H51 . 0.838 no O5 . H52 . 0.839 no O6 . H61 . 0.837 no O6 . H62 . 0.841 no N1 . H11 . 0.860 no N1 . H12 . 0.858 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 1_556 Cu1 . O3 1_556 53.91(17) yes O4 1_556 Cu1 . O1 . 84.7(2) yes O3 1_556 Cu1 . O1 . 89.9(2) yes O4 1_556 Cu1 . O5 . 95.5(3) yes O3 1_556 Cu1 . O5 . 95.2(3) yes O1 . Cu1 . O5 . 173.8(2) yes O4 1_556 Cu1 . O6 . 146.2(3) yes O3 1_556 Cu1 . O6 . 92.4(3) yes O1 . Cu1 . O6 . 93.30(19) yes O5 . Cu1 . O6 . 89.96(19) yes O4 1_556 Cu1 . N1 . 113.2(2) yes O3 1_556 Cu1 . N1 . 166.5(2) yes O1 . Cu1 . N1 . 84.5(2) yes O5 . Cu1 . N1 . 89.8(3) yes O6 . Cu1 . N1 . 100.2(3) yes C2 . C1 . O1 . 117.2(4) yes C2 . C1 . O2 . 119.6(5) yes O1 . C1 . O2 . 123.0(5) yes C1 . C2 . C3 . 108.4(4) yes C1 . C2 . N1 . 108.7(5) yes C3 . C2 . N1 . 109.5(4) yes C1 . C2 . H21 . 110.2 no C3 . C2 . H21 . 109.6 no N1 . C2 . H21 . 110.3 no C2 . C3 . C4 . 116.4(4) yes C2 . C3 . H31 . 107.5 no C4 . C3 . H31 . 107.6 no C2 . C3 . H32 . 107.9 no C4 . C3 . H32 . 107.9 no H31 . C3 . H32 . 109.4 no C3 . C4 . O3 . 115.3(4) yes C3 . C4 . O4 . 121.3(5) yes O3 . C4 . O4 . 123.4(5) yes C1 . O1 . Cu1 . 114.6(4) yes C4 . O3 . Cu1 1_554 108.6(3) yes C4 . O4 . Cu1 1_554 72.6(4) yes Cu1 . O5 . H51 . 128.0 no Cu1 . O5 . H52 . 122.8 no H51 . O5 . H52 . 106.8 no Cu1 . O6 . H61 . 91.9 no Cu1 . O6 . H62 . 111.2 no H61 . O6 . H62 . 101.7 no C2 . N1 . Cu1 . 109.3(3) yes C2 . N1 . H11 . 109.2 no Cu1 . N1 . H11 . 109.7 no C2 . N1 . H12 . 109.2 no Cu1 . N1 . H12 . 109.8 no H11 . N1 . H12 . 109.7 no _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 14:20:43 # #LIST 12 BLOCK SCALE X'S CONT CU(1, U'S) CONT C(1, U[ISO]) UNTIL N(1) CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 14:20:43 # #LIST 16 DIST 1.292, 0.01 = C(1) TO O(1) DIST 1.232, 0.01 = C(1) TO O(2) DIST 1.525, 0.01 = C(1) TO C(2) DIST 1.489, 0.01 = C(2) TO N(1) DIST 1.514, 0.01 = C(2) TO C(3) DIST 1.528, 0.01 = C(3) TO C(4) DIST 1.280, 0.01 = C(4) TO O(3) DIST 1.239, 0.01 = C(4) TO O(4) ANGL 123,1= O(2) TO C(1) TO O(1) ANGL 118,1= C(2) TO C(1) TO O(1) ANGL 120,1= C(2) TO C(1) TO O(2) ANGL 109,1= C(1) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO C(1) ANGL 115,1= C(4) TO C(3) TO C(2) ANGL 124,1= O(4) TO C(4) TO O(3) ANGL 114,1= C(3) TO C(4) TO O(3) ANGL 122,1= C(3) TO C(4) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = O(1) TO C(1) VIBR .0, 0.00200 = O(2) TO C(1) VIBR .0, 0.00200 = O(3) TO C(4) VIBR .0, 0.00200 = O(4) TO C(4) VIBR .0, 0.00200 = N(1) TO C(2) VIBR .0, 0.00200 = C(1) TO C(2) VIBR .0, 0.00500 = O(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(2) VIBR .0, 0.00200 = C(2) TO C(3) VIBR .0, 0.00500 = N(1) TO C(1) VIBR .0, 0.00500 = C(3) TO C(1) VIBR .0, 0.00500 = C(3) TO N(1) VIBR .0, 0.00200 = C(3) TO C(4) VIBR .0, 0.00500 = C(4) TO C(2) VIBR .0, 0.00500 = O(3) TO C(3) VIBR .0, 0.00500 = O(4) TO C(3) VIBR .0, 0.00500 = O(4) TO O(3) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.08000 = O(1) TO C(1) U(IJ) .0, 0.08000 = O(2) TO C(1) U(IJ) .0, 0.08000 = O(3) TO C(4) U(IJ) .0, 0.08000 = O(4) TO C(4) U(IJ) .0, 0.08000 = N(1) TO C(2) U(IJ) .0, 0.04000 = C(1) TO C(2) U(IJ) .0, 0.04000 = C(2) TO C(3) U(IJ) .0, 0.04000 = C(3) TO C(4) REM THERMSIM END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 2 2 0 x . 4 10 4 x . -5 -1 2 x . 4 -4 3 x . 1 7 3 x . 5 9 4 x . -3 5 2 x . 6 8 4 x . data_ceth06 _database_code_depnum_ccdc_archive 'CCDC 856793' #TrackingRef '- all.cif' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'ceth06 in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C4 H9 Cu1 N1 O6' # Given Formula = C4 H7 Cu1 N1 O6 # Dc = 2.44 Fooo = 468.00 Mu = 34.99 M = 228.65 # Found Formula = C4 H9 Cu1 N1 O6 # Dc = 2.46 FOOO = 468.00 Mu = 35.00 M = 230.66 _chemical_formula_sum 'C4 H9 Cu1 N1 O6' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 5900000 _publ_section_exptl_refinement ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.420 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 10 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 46 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 2 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 164 915_ALERT_3_B Low Friedel Pair Coverage ...................... 35 Perc. 952_ALERT_5_G Reported and Calculated Lmax Values Differ by .. 6 These are caused by shading of the high-pressure cell. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 11 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 37 All 1,2 and 1,3 distances were restrained on the L-Asp ligand during refinement. Only the Cu-atom was refned with anisotropic displacement parameters, all other non-H atoms were refined isotropically. This strategy was utilised based on the low-completeness of the high-pressure data. 415_ALERT_2_C Short Inter D-H..H-X H21 .. H61 .. 2.11 Ang. Short contacts are expected at high-pressure. 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.48 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 8.9747(5) _cell_length_b 9.5739(6) _cell_length_c 7.2465(11) _cell_angle_alpha 90 _cell_angle_beta 91.332(8) _cell_angle_gamma 90 _cell_volume 622.47(11) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'C 2y' 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.66 _cell_measurement_reflns_used 1340 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 2.461 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.500 # Sheldrick geometric approximatio 0.50 0.70 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_T_max 0.70 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type ' synchrotron' _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 2505 _reflns_number_total 723 _diffrn_reflns_av_R_equivalents 0.043 # Number of reflections without Friedels Law is 723 # Number of reflections with Friedels Law is 401 # Theoretical number of reflections is about 951 _diffrn_reflns_theta_min 3.112 _diffrn_reflns_theta_max 30.515 _diffrn_measured_fraction_theta_max 0.396 _diffrn_reflns_theta_full 25.022 _diffrn_measured_fraction_theta_full 0.420 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.50 _refine_diff_density_max 0.51 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 714 _refine_ls_number_restraints 37 _refine_ls_number_parameters 55 _oxford_refine_ls_R_factor_ref 0.0371 _refine_ls_wR_factor_ref 0.0642 _refine_ls_goodness_of_fit_ref 0.9640 _refine_ls_shift/su_max 0.0002175 _refine_ls_shift/su_mean 0.0000328 # The values computed from all data _oxford_reflns_number_all 714 _refine_ls_R_factor_all 0.0371 _refine_ls_wR_factor_all 0.0642 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 582 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_gt 0.0553 _refine_ls_abs_structure_Flack 0.26(3) _refine_ls_abs_structure_details 'Flack (1983), 322 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 3.98 4.18 0.887 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.24203(7) 1.00677(15) 0.8626(2) 0.0175 1.0000 Uani . . . . . . C1 C 0.3234(6) 0.7702(5) 0.6824(11) 0.0120(8) 1.0000 Uiso D U . . . . C2 C 0.2235(5) 0.8432(5) 0.5418(11) 0.0117(8) 1.0000 Uiso D U . . . . C3 C 0.3210(5) 0.9143(5) 0.4025(12) 0.0114(9) 1.0000 Uiso D U . . . . C4 C 0.2496(5) 0.9443(5) 0.2133(11) 0.0126(8) 1.0000 Uiso D U . . . . O1 O 0.3411(5) 0.8291(4) 0.8404(12) 0.0164(9) 1.0000 Uiso D U . . . . O2 O 0.3909(4) 0.6628(4) 0.6375(13) 0.0129(8) 1.0000 Uiso D U . . . . O3 O 0.3234(4) 1.0249(4) 0.1094(11) 0.0145(9) 1.0000 Uiso D U . . . . O4 O 0.1273(4) 0.8915(4) 0.1658(13) 0.0138(8) 1.0000 Uiso D U . . . . O5 O 0.1254(4) 1.1737(4) 0.8683(15) 0.0159(10) 1.0000 Uiso . . . . . . O6 O 0.4312(5) 1.1279(4) 0.7462(15) 0.0165(10) 1.0000 Uiso . . . . . . N1 N 0.1350(5) 0.9509(4) 0.6395(15) 0.0119(9) 1.0000 Uiso D U . . . . H31 H 0.3530 1.0030 0.4549 0.0141 1.0000 Uiso R . . . . . H32 H 0.4071 0.8554 0.3840 0.0141 1.0000 Uiso R . . . . . H21 H 0.1572 0.7758 0.4793 0.0146 1.0000 Uiso R . . . . . H11 H 0.1223 1.0221 0.5689 0.0148 1.0000 Uiso R . . . . . H12 H 0.0502 0.9164 0.6672 0.0148 1.0000 Uiso R . . . . . H61 H 0.4175 1.2095 0.7847 0.0214 1.0000 Uiso R . . . . . H62 H 0.5115 1.1010 0.7966 0.0214 1.0000 Uiso R . . . . . H51 H 0.1381 1.2448 0.9347 0.0204 1.0000 Uiso R . . . . . H52 H 0.0356 1.1703 0.8333 0.0204 1.0000 Uiso R . . . . . 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 Cu1 0.0140(2) 0.0115(3) 0.027(2) 0.0005(7) -0.0038(4) 0.0028(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2324(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O4 1_556 2.685(8) yes Cu1 . O3 1_556 1.924(8) yes Cu1 . O1 . 1.928(4) yes Cu1 . O5 . 1.911(4) yes Cu1 . O6 . 2.238(6) yes Cu1 . N1 . 1.937(9) yes C1 . C2 . 1.513(7) yes C1 . O1 . 1.283(8) yes C1 . O2 . 1.241(5) yes C2 . C3 . 1.513(8) yes C2 . N1 . 1.490(7) yes C2 . H21 . 0.982 no C3 . C4 . 1.528(8) yes C3 . H31 . 0.971 no C3 . H32 . 0.968 no C4 . O3 . 1.274(7) yes C4 . O4 . 1.249(5) yes O5 . H51 . 0.840 no O5 . H52 . 0.841 no O6 . H61 . 0.840 no O6 . H62 . 0.841 no N1 . H11 . 0.859 no N1 . H12 . 0.857 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 1_556 Cu1 . O3 1_556 54.60(19) yes O4 1_556 Cu1 . O1 . 83.8(3) yes O3 1_556 Cu1 . O1 . 89.5(3) yes O4 1_556 Cu1 . O5 . 96.1(3) yes O3 1_556 Cu1 . O5 . 95.8(3) yes O1 . Cu1 . O5 . 173.4(3) yes O4 1_556 Cu1 . O6 . 146.1(3) yes O3 1_556 Cu1 . O6 . 91.7(3) yes O1 . Cu1 . O6 . 94.1(2) yes O5 . Cu1 . O6 . 89.7(2) yes O4 1_556 Cu1 . N1 . 112.2(2) yes O3 1_556 Cu1 . N1 . 166.2(3) yes O1 . Cu1 . N1 . 84.7(2) yes O5 . Cu1 . N1 . 89.3(3) yes O6 . Cu1 . N1 . 101.2(3) yes C2 . C1 . O1 . 117.2(4) yes C2 . C1 . O2 . 119.4(5) yes O1 . C1 . O2 . 123.2(5) yes C1 . C2 . C3 . 108.3(4) yes C1 . C2 . N1 . 108.3(5) yes C3 . C2 . N1 . 109.2(4) yes C1 . C2 . H21 . 110.5 no C3 . C2 . H21 . 110.0 no N1 . C2 . H21 . 110.4 no C2 . C3 . C4 . 116.5(4) yes C2 . C3 . H31 . 107.6 no C4 . C3 . H31 . 107.5 no C2 . C3 . H32 . 107.9 no C4 . C3 . H32 . 107.8 no H31 . C3 . H32 . 109.5 no C3 . C4 . O3 . 115.5(4) yes C3 . C4 . O4 . 121.2(5) yes O3 . C4 . O4 . 123.2(6) yes C1 . O1 . Cu1 . 114.5(4) yes C4 . O3 . Cu1 1_554 107.7(3) yes C4 . O4 . Cu1 1_554 73.0(4) yes Cu1 . O5 . H51 . 128.6 no Cu1 . O5 . H52 . 118.9 no H51 . O5 . H52 . 108.7 no Cu1 . O6 . H61 . 103.8 no Cu1 . O6 . H62 . 109.1 no H61 . O6 . H62 . 105.8 no C2 . N1 . Cu1 . 109.1(3) yes C2 . N1 . H11 . 109.4 no Cu1 . N1 . H11 . 109.5 no C2 . N1 . H12 . 109.3 no Cu1 . N1 . H12 . 109.6 no H11 . N1 . H12 . 109.9 no _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 14:24:11 # #LIST 12 BLOCK SCALE X'S CONT CU(1, U'S) CONT C(1, U[ISO]) UNTIL N(1) CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 14:24:11 # #LIST 16 DIST 1.292, 0.01 = C(1) TO O(1) DIST 1.232, 0.01 = C(1) TO O(2) DIST 1.525, 0.01 = C(1) TO C(2) DIST 1.489, 0.01 = C(2) TO N(1) DIST 1.514, 0.01 = C(2) TO C(3) DIST 1.528, 0.01 = C(3) TO C(4) DIST 1.280, 0.01 = C(4) TO O(3) DIST 1.239, 0.01 = C(4) TO O(4) ANGL 123,1= O(2) TO C(1) TO O(1) ANGL 118,1= C(2) TO C(1) TO O(1) ANGL 120,1= C(2) TO C(1) TO O(2) ANGL 109,1= C(1) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO C(1) ANGL 115,1= C(4) TO C(3) TO C(2) ANGL 124,1= O(4) TO C(4) TO O(3) ANGL 114,1= C(3) TO C(4) TO O(3) ANGL 122,1= C(3) TO C(4) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = O(1) TO C(1) VIBR .0, 0.00200 = O(2) TO C(1) VIBR .0, 0.00200 = O(3) TO C(4) VIBR .0, 0.00200 = O(4) TO C(4) VIBR .0, 0.00200 = N(1) TO C(2) VIBR .0, 0.00200 = C(1) TO C(2) VIBR .0, 0.00500 = O(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(2) VIBR .0, 0.00200 = C(2) TO C(3) VIBR .0, 0.00500 = N(1) TO C(1) VIBR .0, 0.00500 = C(3) TO C(1) VIBR .0, 0.00500 = C(3) TO N(1) VIBR .0, 0.00200 = C(3) TO C(4) VIBR .0, 0.00500 = C(4) TO C(2) VIBR .0, 0.00500 = O(3) TO C(3) VIBR .0, 0.00500 = O(4) TO C(3) VIBR .0, 0.00500 = O(4) TO O(3) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.08000 = O(1) TO C(1) U(IJ) .0, 0.08000 = O(2) TO C(1) U(IJ) .0, 0.08000 = O(3) TO C(4) U(IJ) .0, 0.08000 = O(4) TO C(4) U(IJ) .0, 0.08000 = N(1) TO C(2) U(IJ) .0, 0.04000 = C(1) TO C(2) U(IJ) .0, 0.04000 = C(2) TO C(3) U(IJ) .0, 0.04000 = C(3) TO C(4) REM THERMSIM END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 4 10 4 x . 3 5 3 x . 1 7 3 x . 5 9 4 x . 8 4 4 x . 4 -4 3 x . 1 -3 0 x . 1 3 0 x . 4 0 1 x . data_ceth07 _database_code_depnum_ccdc_archive 'CCDC 856794' #TrackingRef '- all.cif' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'ceth07 in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C4 H9 Cu1 N1 O6' # Given Formula = C4 H5 Cu1 N1 O6 # Dc = 2.44 Fooo = 468.00 Mu = 35.33 M = 226.63 # Found Formula = C4 H9 Cu1 N1 O6 # Dc = 2.49 FOOO = 468.00 Mu = 35.35 M = 230.66 _chemical_formula_sum 'C4 H9 Cu1 N1 O6' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 6770000 _publ_section_exptl_refinement ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.389 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 171 915_ALERT_3_B Low Friedel Pair Coverage ...................... 34 Perc. 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 14 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 69 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 2 918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc) 1 952_ALERT_5_G Reported and Calculated Lmax Values Differ by .. 6 These are caused by shading of the high-pressure cell. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 11 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 37 All 1,2 and 1,3 distances were restrained on the L-Asp ligand during refinement. Only the Cu-atom was refned with anisotropic displacement parameters, all other non-H atoms were refined isotropically. This strategy was utilised based on the low-completeness of the high-pressure data. 415_ALERT_2_A Short Inter D-H..H-X H21 .. H61 .. 1.74 Ang. Short contacts are expected at high-pressure. 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.40 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 8.9403(6) _cell_length_b 9.5601(8) _cell_length_c 7.2112(14) _cell_angle_alpha 90 _cell_angle_beta 90.949(12) _cell_angle_gamma 90 _cell_volume 616.26(14) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'C 2y' 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.66 _cell_measurement_reflns_used 963 _cell_measurement_theta_min 4 _cell_measurement_theta_max 17 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 2.486 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.535 # Sheldrick geometric approximatio 0.49 0.70 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.56 _exptl_absorpt_correction_T_max 0.70 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type ' synchrotron' _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 2337 _reflns_number_total 674 _diffrn_reflns_av_R_equivalents 0.060 # Number of reflections without Friedels Law is 674 # Number of reflections with Friedels Law is 365 # Theoretical number of reflections is about 942 _diffrn_reflns_theta_min 3.120 _diffrn_reflns_theta_max 30.520 _diffrn_measured_fraction_theta_max 0.363 _diffrn_reflns_theta_full 25.027 _diffrn_measured_fraction_theta_full 0.389 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.81 _refine_diff_density_max 0.76 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 669 _refine_ls_number_restraints 37 _refine_ls_number_parameters 55 _oxford_refine_ls_R_factor_ref 0.0529 _refine_ls_wR_factor_ref 0.0957 _refine_ls_goodness_of_fit_ref 0.8687 _refine_ls_shift/su_max 0.0000760 _refine_ls_shift/su_mean 0.0000126 # The values computed from all data _oxford_reflns_number_all 669 _refine_ls_R_factor_all 0.0529 _refine_ls_wR_factor_all 0.0957 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 512 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_gt 0.0755 _refine_ls_abs_structure_Flack 0.27(5) _refine_ls_abs_structure_details 'Flack (1983), 309 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 7.57 7.70 2.05 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.24241(11) 1.0069(2) 0.8612(4) 0.0237 1.0000 Uani . . . . . . C1 C 0.3248(9) 0.7690(7) 0.6802(15) 0.0154(11) 1.0000 Uiso D U . . . . C2 C 0.2236(7) 0.8414(7) 0.5395(15) 0.0147(11) 1.0000 Uiso D U . . . . C3 C 0.3225(8) 0.9127(8) 0.4006(16) 0.0146(11) 1.0000 Uiso D U . . . . C4 C 0.2511(7) 0.9447(8) 0.2123(15) 0.0139(11) 1.0000 Uiso D U . . . . O1 O 0.3430(7) 0.8286(6) 0.8379(17) 0.0169(12) 1.0000 Uiso D U . . . . O2 O 0.3915(7) 0.6609(6) 0.636(2) 0.0156(12) 1.0000 Uiso D U . . . . O3 O 0.3248(6) 1.0281(6) 0.1121(16) 0.0141(12) 1.0000 Uiso D U . . . . O4 O 0.1292(6) 0.8921(6) 0.1644(19) 0.0141(12) 1.0000 Uiso D U . . . . O5 O 0.1270(7) 1.1746(6) 0.868(3) 0.0194(16) 1.0000 Uiso . . . . . . O6 O 0.4310(8) 1.1288(6) 0.742(2) 0.0192(16) 1.0000 Uiso . . . . . . N1 N 0.1336(7) 0.9483(7) 0.636(2) 0.0144(13) 1.0000 Uiso D U . . . . H31 H 0.3549 1.0009 0.4544 0.0185 1.0000 Uiso R . . . . . H32 H 0.4086 0.8531 0.3816 0.0185 1.0000 Uiso R . . . . . H21 H 0.1587 0.7726 0.4777 0.0156 1.0000 Uiso R . . . . . H11 H 0.1174 1.0187 0.5647 0.0151 1.0000 Uiso R . . . . . H12 H 0.0489 0.9119 0.6667 0.0151 1.0000 Uiso R . . . . . H61 H 0.4365 1.2148 0.7202 0.0246 1.0000 Uiso R . . . . . H62 H 0.5038 1.1081 0.8117 0.0246 1.0000 Uiso R . . . . . H51 H 0.1287 1.2470 0.9338 0.0241 1.0000 Uiso R . . . . . H52 H 0.0405 1.1541 0.8297 0.0241 1.0000 Uiso R . . . . . 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 Cu1 0.0109(4) 0.0166(4) 0.043(3) 0.0011(13) -0.0052(6) 0.0017(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2407(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O4 1_556 2.662(13) yes Cu1 . O3 1_556 1.953(11) yes Cu1 . O1 . 1.936(6) yes Cu1 . O5 . 1.908(7) yes Cu1 . O6 . 2.234(10) yes Cu1 . N1 . 1.959(13) yes C1 . C2 . 1.516(8) yes C1 . O1 . 1.280(9) yes C1 . O2 . 1.237(7) yes C2 . C3 . 1.510(9) yes C2 . N1 . 1.482(8) yes C2 . H21 . 0.979 no C3 . C4 . 1.522(9) yes C3 . H31 . 0.970 no C3 . H32 . 0.969 no C4 . O3 . 1.267(8) yes C4 . O4 . 1.245(7) yes O5 . H51 . 0.839 no O5 . H52 . 0.840 no O6 . H61 . 0.839 no O6 . H62 . 0.840 no N1 . H11 . 0.860 no N1 . H12 . 0.864 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 1_556 Cu1 . O3 1_556 54.9(3) yes O4 1_556 Cu1 . O1 . 83.8(4) yes O3 1_556 Cu1 . O1 . 90.2(4) yes O4 1_556 Cu1 . O5 . 96.4(5) yes O3 1_556 Cu1 . O5 . 94.8(5) yes O1 . Cu1 . O5 . 174.0(4) yes O4 1_556 Cu1 . O6 . 146.2(4) yes O3 1_556 Cu1 . O6 . 91.6(5) yes O1 . Cu1 . O6 . 94.1(3) yes O5 . Cu1 . O6 . 89.1(4) yes O4 1_556 Cu1 . N1 . 111.8(4) yes O3 1_556 Cu1 . N1 . 166.2(4) yes O1 . Cu1 . N1 . 84.3(4) yes O5 . Cu1 . N1 . 90.0(5) yes O6 . Cu1 . N1 . 101.4(5) yes C2 . C1 . O1 . 117.2(5) yes C2 . C1 . O2 . 119.7(6) yes O1 . C1 . O2 . 123.0(6) yes C1 . C2 . C3 . 107.5(5) yes C1 . C2 . N1 . 108.8(6) yes C3 . C2 . N1 . 109.3(6) yes C1 . C2 . H21 . 109.9 no C3 . C2 . H21 . 110.5 no N1 . C2 . H21 . 110.8 no C2 . C3 . C4 . 116.2(5) yes C2 . C3 . H31 . 107.5 no C4 . C3 . H31 . 107.5 no C2 . C3 . H32 . 107.6 no C4 . C3 . H32 . 108.3 no H31 . C3 . H32 . 109.6 no C3 . C4 . O3 . 114.9(5) yes C3 . C4 . O4 . 121.2(6) yes O3 . C4 . O4 . 123.9(6) yes C1 . O1 . Cu1 . 114.6(6) yes C4 . O3 . Cu1 1_554 105.7(5) yes Cu1 1_554 O4 . C4 . 73.6(5) yes Cu1 . O5 . H51 . 134.7 no Cu1 . O5 . H52 . 106.9 no H51 . O5 . H52 . 112.8 no Cu1 . O6 . H61 . 129.0 no Cu1 . O6 . H62 . 103.2 no H61 . O6 . H62 . 107.2 no C2 . N1 . Cu1 . 108.7(5) yes C2 . N1 . H11 . 110.1 no Cu1 . N1 . H11 . 110.5 no C2 . N1 . H12 . 109.1 no Cu1 . N1 . H12 . 109.3 no H11 . N1 . H12 . 109.1 no _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 14:30:01 # #LIST 12 BLOCK SCALE X'S CONT CU(1, U'S) CONT C(1, U[ISO]) UNTIL N(1) CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 14:30:01 # #LIST 16 DIST 1.292, 0.01 = C(1) TO O(1) DIST 1.232, 0.01 = C(1) TO O(2) DIST 1.525, 0.01 = C(1) TO C(2) DIST 1.489, 0.01 = C(2) TO N(1) DIST 1.514, 0.01 = C(2) TO C(3) DIST 1.528, 0.01 = C(3) TO C(4) DIST 1.280, 0.01 = C(4) TO O(3) DIST 1.239, 0.01 = C(4) TO O(4) ANGL 123,1= O(2) TO C(1) TO O(1) ANGL 118,1= C(2) TO C(1) TO O(1) ANGL 120,1= C(2) TO C(1) TO O(2) ANGL 109,1= C(1) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO C(1) ANGL 115,1= C(4) TO C(3) TO C(2) ANGL 124,1= O(4) TO C(4) TO O(3) ANGL 114,1= C(3) TO C(4) TO O(3) ANGL 122,1= C(3) TO C(4) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = O(1) TO C(1) VIBR .0, 0.00200 = O(2) TO C(1) VIBR .0, 0.00200 = O(3) TO C(4) VIBR .0, 0.00200 = O(4) TO C(4) VIBR .0, 0.00200 = N(1) TO C(2) VIBR .0, 0.00200 = C(1) TO C(2) VIBR .0, 0.00500 = O(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(2) VIBR .0, 0.00200 = C(2) TO C(3) VIBR .0, 0.00500 = N(1) TO C(1) VIBR .0, 0.00500 = C(3) TO C(1) VIBR .0, 0.00500 = C(3) TO N(1) VIBR .0, 0.00200 = C(3) TO C(4) VIBR .0, 0.00500 = C(4) TO C(2) VIBR .0, 0.00500 = O(3) TO C(3) VIBR .0, 0.00500 = O(4) TO C(3) VIBR .0, 0.00500 = O(4) TO O(3) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.08000 = O(1) TO C(1) U(IJ) .0, 0.08000 = O(2) TO C(1) U(IJ) .0, 0.08000 = O(3) TO C(4) U(IJ) .0, 0.08000 = O(4) TO C(4) U(IJ) .0, 0.08000 = N(1) TO C(2) U(IJ) .0, 0.04000 = C(1) TO C(2) U(IJ) .0, 0.04000 = C(2) TO C(3) U(IJ) .0, 0.04000 = C(3) TO C(4) REM THERMSIM END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 9 -1 4 x . -1 9 3 x . -6 2 2 x . -5 11 3 x . -2 10 3 x . data_ceth08 _database_code_depnum_ccdc_archive 'CCDC 856795' #TrackingRef '- all.cif' _audit_creation_date 11-07-11 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'jamie in C2' _chemical_name_systematic ? _chemical_name_common CuAsp _chemical_formula_moiety 'C4 H9 Cu1 N1 O6' # Given Formula = C9 H10 Cu1 N1 O6 # Dc = 3.19 Fooo = 468.00 Mu = 36.22 M = 291.73 # Found Formula = C4 H9 Cu1 N1 O6 # Dc = 2.52 FOOO = 468.00 Mu = 35.84 M = 230.66 _chemical_formula_sum 'C4 H9 Cu1 N1 O6' _chemical_compound_source ? _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour blue _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 7890000 _publ_section_exptl_refinement ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.379 026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 36 Perc. 341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang .. 23 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 177 915_ALERT_3_B Low Friedel Pair Coverage ...................... 34 Perc. 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 76 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 2 918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc) 1 952_ALERT_5_G Reported and Calculated Lmax Values Differ by .. 6 These are caused by shading of the high-pressure cell. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 11 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 37 All 1,2 and 1,3 distances were restrained on the L-Asp ligand during refinement. Only the Cu-atom was refned with anisotropic displacement parameters, all other non-H atoms were refined isotropically. This strategy was utilised based on the low-completeness of the high-pressure data. 415_ALERT_2_A Short Inter D-H..H-X H21 .. H61 .. 1.71 Ang. Short contacts are expected at high-pressure. 157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg 89.83 Deg. The structure of the high-pressure phase is refined with a beta angle less than 90 degrees in order to compare it to compression of phase-I more easily (see text). 731_ALERT_1_C Bond Calc 1.29(2), Rep 1.291(9) ...... 2 su-Ra C1 -O1 1.555 1.555 # 8 731_ALERT_1_C Bond Calc 1.51(2), Rep 1.506(9) ...... 2 su-Ra C2 -C3 1.555 1.555 # 10 731_ALERT_1_C Bond Calc 1.49(2), Rep 1.487(9) ...... 2 su-Ra C2 -N1 1.555 1.555 # 11 731_ALERT_1_C Bond Calc 1.53(3), Rep 1.522(9) ...... 3 su-Ra C3 -C4 1.555 1.555 # 13 731_ALERT_1_C Bond Calc 1.28(2), Rep 1.280(9) ...... 2 su-Ra C4 -O3 1.555 1.555 # 16 731_ALERT_1_C Bond Calc 1.24(2), Rep 1.237(9) ...... 2 su-Ra C4 -O4 1.555 1.555 # 17 732_ALERT_1_C Angle Calc 123.0(15), Rep 122.9(7) ...... 2.14 su-Ra O1 -C1 -O2 1.555 1.555 1.555 # 18 732_ALERT_1_C Angle Calc 121.3(17), Rep 121.4(7) ...... 2.43 su-Ra C3 -C4 -O4 1.555 1.555 1.555 # 32 732_ALERT_1_C Angle Calc 125(2), Rep 124.4(7) ...... 2.86 su-Ra O3 -C4 -O4 1.555 1.555 1.555 # 33 The use of restraints in the refinement mean that off diagonal terms in the variance-covariance matrix are significant, and the diagonal approximation used in Platon/Checkcif is badly in error. 004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K 791_ALERT_4_G Note: The Model has Chirality at C2 (Verify) S These are correct. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! No action taken. 794_ALERT_5_G Note: Tentative Bond Valency for Cu1 (II) 2.56 The Cu is in a distorted octahedral geometry, giving rise to the tentative bond valency. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! A shelx weighting scheme was not used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; #end of refcif _cell_length_a 8.9493(9) _cell_length_b 9.6210(13) _cell_length_c 7.059(2) _cell_angle_alpha 90 _cell_angle_beta 89.829(18) _cell_angle_gamma 90 _cell_volume 607.8(2) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'C 2y' 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_weight 230.66 _cell_measurement_reflns_used 781 _cell_measurement_theta_min 4 _cell_measurement_theta_max 18 _cell_measurement_temperature 293 _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 2.521 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.584 # Sheldrick geometric approximatio 0.49 0.70 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.70 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type ' synchrotron' _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 1994 _reflns_number_total 647 _diffrn_reflns_av_R_equivalents 0.091 # Number of reflections without Friedels Law is 647 # Number of reflections with Friedels Law is 347 # Theoretical number of reflections is about 918 _diffrn_reflns_theta_min 3.109 _diffrn_reflns_theta_max 30.384 _diffrn_measured_fraction_theta_max 0.355 _diffrn_reflns_theta_full 25.219 _diffrn_measured_fraction_theta_full 0.379 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -1.16 _refine_diff_density_max 1.08 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 647 _refine_ls_number_restraints 37 _refine_ls_number_parameters 55 _oxford_refine_ls_R_factor_ref 0.0887 _refine_ls_wR_factor_ref 0.2465 _refine_ls_goodness_of_fit_ref 1.0151 _refine_ls_shift/su_max 0.0000432 _refine_ls_shift/su_mean 0.0000083 # The values computed from all data _oxford_reflns_number_all 647 _refine_ls_R_factor_all 0.0887 _refine_ls_wR_factor_all 0.2465 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 230 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_gt 0.1151 _refine_ls_abs_structure_Flack 0.04(12) _refine_ls_abs_structure_details 'Flack (1983), 300 Friedel-pairs' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 14.1 17.3 5.80 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.2440(2) 1.0066(4) 0.8568(8) 0.0274 1.0000 Uani . . . . . . C1 C 0.3265(16) 0.7660(11) 0.682(2) 0.0209(16) 1.0000 Uiso D U . . . . C2 C 0.2262(12) 0.8377(10) 0.538(2) 0.0208(16) 1.0000 Uiso D U . . . . C3 C 0.3240(13) 0.9117(16) 0.396(3) 0.0211(17) 1.0000 Uiso D U . . . . C4 C 0.2519(15) 0.9486(18) 0.207(3) 0.0216(17) 1.0000 Uiso D U . . . . O1 O 0.3486(14) 0.8303(13) 0.840(3) 0.0214(19) 1.0000 Uiso D U . . . . O2 O 0.3902(13) 0.6563(11) 0.640(3) 0.0202(19) 1.0000 Uiso D U . . . . O3 O 0.3271(12) 1.0351(11) 0.108(3) 0.022(2) 1.0000 Uiso D U . . . . O4 O 0.1347(13) 0.8924(12) 0.155(3) 0.0224(19) 1.0000 Uiso D U . . . . O5 O 0.1282(15) 1.1740(13) 0.859(6) 0.023(3) 1.0000 Uiso . . . . . . O6 O 0.4316(15) 1.1328(14) 0.750(5) 0.024(3) 1.0000 Uiso . . . . . . N1 N 0.1321(14) 0.9406(13) 0.640(4) 0.021(2) 1.0000 Uiso D U . . . . H31 H 0.3611 0.9955 0.4544 0.0268 1.0000 Uiso R . . . . . H32 H 0.4068 0.8498 0.3673 0.0268 1.0000 Uiso R . . . . . H21 H 0.1618 0.7692 0.4746 0.0273 1.0000 Uiso R . . . . . H11 H 0.1119 1.0087 0.5665 0.0273 1.0000 Uiso R . . . . . H12 H 0.0500 0.9025 0.6784 0.0273 1.0000 Uiso R . . . . . H61 H 0.4112 1.2175 0.7372 0.0312 1.0000 Uiso R . . . . . H62 H 0.5080 1.1286 0.8185 0.0312 1.0000 Uiso R . . . . . H51 H 0.1508 1.2419 0.9276 0.0264 1.0000 Uiso R . . . . . H52 H 0.0389 1.1840 0.8248 0.0264 1.0000 Uiso R . . . . . 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 Cu1 0.0171(8) 0.0228(10) 0.042(8) -0.001(2) -0.0077(15) 0.0027(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2317(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O4 1_556 2.57(2) yes Cu1 . O3 1_556 1.94(2) yes Cu1 . O1 . 1.942(13) yes Cu1 . O5 . 1.915(14) yes Cu1 . O6 . 2.20(2) yes Cu1 . N1 . 1.94(2) yes C1 . C2 . 1.523(9) yes C1 . O1 . 1.291(9) yes C1 . O2 . 1.235(9) yes C2 . C3 . 1.506(9) yes C2 . N1 . 1.487(9) yes C2 . H21 . 0.983 no C3 . C4 . 1.522(9) yes C3 . H31 . 0.966 no C3 . H32 . 0.971 no C4 . O3 . 1.280(9) yes C4 . O4 . 1.237(9) yes O5 . H51 . 0.840 no O5 . H52 . 0.840 no O6 . H61 . 0.840 no O6 . H62 . 0.840 no N1 . H11 . 0.856 no N1 . H12 . 0.863 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 1_556 Cu1 . O3 1_556 57.2(5) yes O4 1_556 Cu1 . O1 . 81.9(7) yes O3 1_556 Cu1 . O1 . 89.6(6) yes O4 1_556 Cu1 . O5 . 98.6(11) yes O3 1_556 Cu1 . O5 . 94.9(11) yes O1 . Cu1 . O5 . 175.0(9) yes O4 1_556 Cu1 . O6 . 143.6(9) yes O3 1_556 Cu1 . O6 . 86.6(10) yes O1 . Cu1 . O6 . 95.3(6) yes O5 . Cu1 . O6 . 87.2(7) yes O4 1_556 Cu1 . N1 . 108.1(6) yes O3 1_556 Cu1 . N1 . 165.0(7) yes O1 . Cu1 . N1 . 85.1(6) yes O5 . Cu1 . N1 . 90.0(10) yes O6 . Cu1 . N1 . 107.8(10) yes C2 . C1 . O1 . 116.9(7) yes C2 . C1 . O2 . 120.0(7) yes O1 . C1 . O2 . 122.9(7) yes C1 . C2 . C3 . 108.4(8) yes C1 . C2 . N1 . 108.1(8) yes C3 . C2 . N1 . 109.6(8) yes C1 . C2 . H21 . 110.3 no C3 . C2 . H21 . 110.8 no N1 . C2 . H21 . 109.5 no C2 . C3 . C4 . 116.4(7) yes C2 . C3 . H31 . 108.1 no C4 . C3 . H31 . 109.1 no C2 . C3 . H32 . 106.8 no C4 . C3 . H32 . 106.7 no H31 . C3 . H32 . 109.7 no C3 . C4 . O3 . 114.1(7) yes C3 . C4 . O4 . 121.4(7) yes O3 . C4 . O4 . 124.4(7) yes C1 . O1 . Cu1 . 113.4(8) yes C4 . O3 . Cu1 1_554 102.0(8) yes Cu1 1_554 O4 . C4 . 74.7(8) yes Cu1 . O5 . H51 . 121.8 no Cu1 . O5 . H52 . 127.6 no H51 . O5 . H52 . 107.8 no Cu1 . O6 . H61 . 113.9 no Cu1 . O6 . H62 . 113.4 no H61 . O6 . H62 . 106.6 no C2 . N1 . Cu1 . 108.0(9) yes C2 . N1 . H11 . 109.5 no Cu1 . N1 . H11 . 109.8 no C2 . N1 . H12 . 110.5 no Cu1 . N1 . H12 . 109.5 no H11 . N1 . H12 . 109.5 no _iucr_refine_instruction_details_constraints ; # # Punched on 11/07/11 at 14:44:18 # #LIST 12 BLOCK SCALE X'S CONT CU(1, U'S) CONT C(1, U[ISO]) UNTIL N(1) CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) RIDE O ( 5,X'S) H ( 51,X'S) H ( 52,X'S) RIDE O ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/07/11 at 14:44:18 # #LIST 16 DIST 1.292, 0.01 = C(1) TO O(1) DIST 1.232, 0.01 = C(1) TO O(2) DIST 1.525, 0.01 = C(1) TO C(2) DIST 1.489, 0.01 = C(2) TO N(1) DIST 1.514, 0.01 = C(2) TO C(3) DIST 1.528, 0.01 = C(3) TO C(4) DIST 1.280, 0.01 = C(4) TO O(3) DIST 1.239, 0.01 = C(4) TO O(4) ANGL 123,1= O(2) TO C(1) TO O(1) ANGL 118,1= C(2) TO C(1) TO O(1) ANGL 120,1= C(2) TO C(1) TO O(2) ANGL 109,1= C(1) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO N(1) ANGL 110,1= C(3) TO C(2) TO C(1) ANGL 115,1= C(4) TO C(3) TO C(2) ANGL 124,1= O(4) TO C(4) TO O(3) ANGL 114,1= C(3) TO C(4) TO O(3) ANGL 122,1= C(3) TO C(4) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = O(1) TO C(1) VIBR .0, 0.00200 = O(2) TO C(1) VIBR .0, 0.00200 = O(3) TO C(4) VIBR .0, 0.00200 = O(4) TO C(4) VIBR .0, 0.00200 = N(1) TO C(2) VIBR .0, 0.00200 = C(1) TO C(2) VIBR .0, 0.00500 = O(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(1) VIBR .0, 0.00500 = C(2) TO O(2) VIBR .0, 0.00200 = C(2) TO C(3) VIBR .0, 0.00500 = N(1) TO C(1) VIBR .0, 0.00500 = C(3) TO C(1) VIBR .0, 0.00500 = C(3) TO N(1) VIBR .0, 0.00200 = C(3) TO C(4) VIBR .0, 0.00500 = C(4) TO C(2) VIBR .0, 0.00500 = O(3) TO C(3) VIBR .0, 0.00500 = O(4) TO C(3) VIBR .0, 0.00500 = O(4) TO O(3) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.08000 = O(1) TO C(1) U(IJ) .0, 0.08000 = O(2) TO C(1) U(IJ) .0, 0.08000 = O(3) TO C(4) U(IJ) .0, 0.08000 = O(4) TO C(4) U(IJ) .0, 0.08000 = N(1) TO C(2) U(IJ) .0, 0.04000 = C(1) TO C(2) U(IJ) .0, 0.04000 = C(2) TO C(3) U(IJ) .0, 0.04000 = C(3) TO C(4) REM THERMSIM END (DO NOT REMOVE THIS LINE) END ;