# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Peter Tasker' _publ_contact_author_address ; University of Edinburgh N2.16, Joseph Black Building King's Buildings West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email 'PETER.TASKER@ED.AC.UK; S9902405@SMS.ED.AC.UK' _publ_section_title ; Supramolecular chemistry in metal recovery; H-bond buttressing to tune extractant strength ; loop_ _publ_author_name 'Peter Tasker' 'John Campbell' 'Ross Forgan' 'David K. Henderson' 'Fiona E. McAllister' ; S.Parsons ; 'Elna Pidcock' 'Ronald M. Swart' 'Peter Wood' data_L1H _database_code_depnum_ccdc_archive 'CCDC 629858' _audit_update_record ; 2007-08-03 # Formatted by publCIF ; _chemical_compound_source 'R. Forgan' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of hexane/chloroform solution' _audit_creation_date 05-06-13 _audit_creation_method CRYSTALS_ver_12.82 _chemical_name_common salicylaldoxime _chemical_name_systematic '2-hydroxybenzaldehyde oxime' _chemical_melting_point 59-61 _chemical_formula_sum 'C7 H7 N1 O2' _chemical_formula_moiety 'C7 H7 N1 O2' _chemical_formula_weight 137.14 _cell_length_a 10.346(4) _cell_length_b 5.0294(17) _cell_length_c 13.478(5) _cell_angle_alpha 90 _cell_angle_beta 112.21(2) _cell_angle_gamma 90 _cell_volume 649.3(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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' # Given Formula = C7 H7 N1 O2 # Dc = 1.40 Fooo = 288.00 Mu = 1.04 M = 137.14 # Found Formula = C7 H7 N1 O2 # Dc = 1.40 FOOO = 288.00 Mu = 1.04 M = 137.14 _cell_measurement_reflns_used 930 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _cell_measurement_temperature 273 _cell_formula_units_Z 4 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.26 _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.104 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker SMART Apex CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _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_ambient_temperature 273 _diffrn_reflns_number 6424 _reflns_number_total 1982 _diffrn_reflns_av_R_equivalents 0.047 # Number of reflections with Friedels Law is 1982 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2009 _diffrn_reflns_theta_min 2.136 _diffrn_reflns_theta_max 30.660 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 29.434 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -14 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _refine_diff_density_max 0.25 _refine_ls_number_reflns 1982 _refine_ls_number_restraints 84 _refine_ls_number_parameters 97 #_refine_ls_R_factor_ref 0.1042 _refine_ls_wR_factor_ref 0.1745 _refine_ls_goodness_of_fit_ref 0.9148 #_reflns_number_all 1982 _refine_ls_R_factor_all 0.1042 _refine_ls_wR_factor_all 0.1745 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 1019 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_gt 0.1419 _refine_ls_shift/su_max 0.000208 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 0.04P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The hydrogens on carbon atoms (H3, H6, H7, H8, H9) were placed geometrically, then refined subject to geometrical restraints and finally allowed to ride on the host carbon. The hydrogens on O1 and O5 were found in a fourier difference map and then refined subject to an O-H distance restraint of 0.82 Angstroms. Used global vibration and thermal similarity restraints. 731_ALERT_1_A Bond Calc 0.82(2), Rep 0.8201(10) ...... 9.90 su-Rat O1 -H1 1.555 1.555 731_ALERT_1_A Bond Calc 0.820(19), Rep 0.8200(10) ...... 9.90 su-Rat O5 -H5 1.555 1.555 These differences in the sus are due to the restraints applied to the O-H bonds for O1-H1 and O5-H5. The values calculated for bond sus by the cif check do not include the full variance/covariance matrix, whereas the values calculated by CRYSTALS do. 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81 Sadabs corrects for all systematic errors that lead to disparities in the intensities of equivalent data. The larger than expected range of transmission is probably due to the absorption effects of the Merrill-Bassett diamond-anvil cell. #============================================================================= Resolution & Completeness Statistics (Cumulative) #============================================================================= Theta sin(th)/Lambda Complete Expected Measured Missing #----------------------------------------------------------------------------- 20.82 0.500 1.000 679 679 0 23.01 0.550 1.000 908 908 0 25.24 0.600 1.000 1166 1166 0 #----------------------------------------------------------- ACTA Min. Res. -- 27.51 0.650 0.999 1491 1490 1 29.84 0.700 0.996 1857 1850 7 32.21 0.750 0.986 2011 1982 29 ; # End of 'script/refcif.dat' 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 O1 O 0.73977(12) 1.0210(3) 0.68075(10) 0.0601 1.0000 Uani D U . . . . N2 N 0.68807(13) 0.8699(3) 0.58726(10) 0.0470 1.0000 Uani . U . . . . C3 C 0.77347(16) 0.6962(4) 0.58178(13) 0.0481 1.0000 Uani . U . . . . C4 C 0.74142(16) 0.5191(3) 0.49063(13) 0.0438 1.0000 Uani . U . . . . C5 C 0.61060(16) 0.5212(3) 0.40569(13) 0.0439 1.0000 Uani . U . . . . O5 O 0.50907(12) 0.6917(3) 0.40416(10) 0.0553 1.0000 Uani D U . . . . C6 C 0.58318(18) 0.3443(4) 0.32144(15) 0.0532 1.0000 Uani . U . . . . C7 C 0.6832(2) 0.1697(4) 0.31882(16) 0.0575 1.0000 Uani . U . . . . C8 C 0.81361(19) 0.1673(4) 0.40143(16) 0.0579 1.0000 Uani . U . . . . C9 C 0.84057(17) 0.3388(4) 0.48613(15) 0.0534 1.0000 Uani . U . . . . H3 H 0.8633 0.6823 0.6391 0.0648 1.0000 Uiso R . . . . . H6 H 0.4943 0.3439 0.2669 0.0734 1.0000 Uiso R . . . . . H7 H 0.6697 0.0489 0.2601 0.0812 1.0000 Uiso R . . . . . H8 H 0.8827 0.0422 0.3992 0.0826 1.0000 Uiso R . . . . . H9 H 0.9324 0.3426 0.5430 0.0738 1.0000 Uiso R . . . . . H1 H 0.6780(19) 1.131(4) 0.672(2) 0.1005 1.0000 Uiso D . . . . . H5 H 0.536(2) 0.793(4) 0.4556(14) 0.0949 1.0000 Uiso D . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0568(7) 0.0641(9) 0.0412(7) -0.0110(6) -0.0022(5) 0.0065(6) N2 0.0465(7) 0.0496(8) 0.0366(7) -0.0030(6) 0.0062(5) -0.0010(6) C3 0.0415(8) 0.0530(10) 0.0418(8) 0.0031(7) 0.0067(6) 0.0023(7) C4 0.0423(7) 0.0423(8) 0.0439(8) 0.0068(6) 0.0131(6) -0.0008(6) C5 0.0424(7) 0.0411(8) 0.0459(9) 0.0038(6) 0.0141(6) 0.0026(6) O5 0.0449(6) 0.0573(8) 0.0498(7) -0.0092(6) 0.0023(5) 0.0096(5) C6 0.0531(9) 0.0523(10) 0.0494(9) -0.0034(7) 0.0139(8) -0.0022(7) C7 0.0697(10) 0.0501(11) 0.0556(10) -0.0016(8) 0.0269(8) 0.0010(8) C8 0.0613(10) 0.0525(11) 0.0648(11) 0.0084(8) 0.0293(8) 0.0136(9) C9 0.0478(9) 0.0545(11) 0.0559(10) 0.0094(8) 0.0173(8) 0.0079(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.59(11) 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 O1 . N2 . 1.3935(18) yes O1 . H1 . 0.8201(10) no N2 . C3 . 1.264(2) yes C3 . C4 . 1.451(2) yes C3 . H3 . 0.960 no C4 . C5 . 1.404(2) yes C4 . C9 . 1.388(2) yes C5 . O5 . 1.3502(19) yes C5 . C6 . 1.385(2) yes O5 . H5 . 0.8200(10) no C6 . C7 . 1.367(2) yes C6 . H6 . 0.935 no C7 . C8 . 1.387(3) yes C7 . H7 . 0.965 no C8 . C9 . 1.373(3) yes C8 . H8 . 0.961 no C9 . H9 . 0.970 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 N2 . O1 . H1 . 103(2) no O1 . N2 . C3 . 113.07(13) yes N2 . C3 . C4 . 122.18(14) yes N2 . C3 . H3 . 119.2 no C4 . C3 . H3 . 118.6 no C3 . C4 . C5 . 121.82(15) yes C3 . C4 . C9 . 120.15(15) yes C5 . C4 . C9 . 118.02(16) yes C4 . C5 . O5 . 121.45(15) yes C4 . C5 . C6 . 119.95(15) yes O5 . C5 . C6 . 118.60(14) yes C5 . O5 . H5 . 111.7(18) no C5 . C6 . C7 . 120.75(17) yes C5 . C6 . H6 . 118.8 no C7 . C6 . H6 . 120.5 no C6 . C7 . C8 . 120.05(18) yes C6 . C7 . H7 . 123.3 no C8 . C7 . H7 . 116.6 no C7 . C8 . C9 . 119.48(16) yes C7 . C8 . H8 . 119.3 no C9 . C8 . H8 . 121.2 no C4 . C9 . C8 . 121.73(17) yes C4 . C9 . H9 . 118.2 no C8 . C9 . H9 . 120.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O5 0.82(2) 2.02(2) 2.793(2) 156(2) 3_676 yes O5 H5 N2 0.820(19) 1.914(19) 2.621(2) 144(2) . yes C6 H6 O1 0.9400 2.5400 3.404(3) 154.00 4_464 yes # Attachment 'L2Hrevised.cif' data_L2H _database_code_depnum_ccdc_archive 'CCDC 656841' _audit_update_record ; 2007-08-03 # Formatted by publCIF ; _chemical_compound_source 'R. Forgan' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of hexane solution' _audit_creation_date 05-11-28 _audit_creation_method CRYSTALS_ver_12.82 _chemical_name_systematic 3-Methylsalicylaldoxime _chemical_melting_point ? _cell_length_a 13.249(4) _cell_length_b 3.9513(11) _cell_length_c 14.402(4) _cell_angle_alpha 90 _cell_angle_beta 90.324(4) _cell_angle_gamma 90 _cell_volume 754.0(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 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' _cell_formula_units_Z 4 # Given Formula = C8 H9 N1 O2 # Dc = 1.33 Fooo = 320.00 Mu = 0.97 M = 151.16 # Found Formula = C8 H9 N1 O2 # Dc = 1.33 FOOO = 320.00 Mu = 0.97 M = 151.16 _chemical_formula_sum 'C8 H9 N1 O2' _chemical_formula_moiety 'C8 H9 N1 O2' _chemical_formula_weight 151.16 _cell_measurement_reflns_used 599 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.097 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details ; Used Oxford Cryosystems low temperature device. Data collection strategy optimised with COSMO. ; _diffrn_measurement_device_type 'Bruker SMART Apex CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _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_ambient_temperature 298 _diffrn_reflns_number 6640 _reflns_number_total 1786 _diffrn_reflns_av_R_equivalents 0.041 # Number of reflections with Friedels Law is 1786 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1947 _diffrn_reflns_theta_min 1.537 _diffrn_reflns_theta_max 28.690 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 26.969 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 5 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.17 _refine_diff_density_max 0.14 _refine_ls_number_reflns 1786 _refine_ls_number_restraints 2 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.1516 _refine_ls_wR_factor_ref 0.1310 _refine_ls_goodness_of_fit_ref 0.6877 #_reflns_number_all 1786 _refine_ls_R_factor_all 0.1516 _refine_ls_wR_factor_all 0.1310 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 627 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_gt 0.1042 _refine_ls_shift/su_max 0.000201 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.00P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The hydrogens were placed geometrically except for H1 and H5 (on O1 and O5 respectively) which were found in a Fourier difference map and then their positions were refined subject to an O-H distance restraint of 0.84 Angstroms. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Checkcif Output: 026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc. The crystal used was very small as it was intended to be used for a high pressure compression study and thus had to be small enough to fit in the diamond anvil cell. As such there seems to be relatively few intense reflections in the dataset. 061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.67 Sadabs corrects for all systematic errors that lead to disparities in the intensities of equivalent data. It is possible that the larger than expected range of transmission is accounted for by crystal decay or absorption by the mounting fibre. 795_ALERT_4_C C-Atom in CIF Coordinate List out of Sequence .. C7 The atom list given is intended to be more chemically significant. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 1.000 779 779 0 23.01 0.550 1.000 1057 1057 0 25.24 0.600 1.000 1371 1371 0 #----------------------------------------------------------- ACTA Min. Res. ---- 27.51 0.650 0.993 1724 1712 12 28.69 0.675 0.917 1947 1786 161 ; # End of 'script/refcif.dat' 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 O1 O 0.56393(13) 0.0895(5) 0.63610(12) 0.0773 1.0000 Uani D . . . . . N2 N 0.47242(14) 0.2337(5) 0.60903(12) 0.0580 1.0000 Uani . . . . . . C3 C 0.40383(17) 0.2023(6) 0.66971(15) 0.0556 1.0000 Uani . . . . . . C4 C 0.30366(16) 0.3371(6) 0.65492(15) 0.0497 1.0000 Uani . . . . . . C5 C 0.27359(16) 0.4870(6) 0.57096(15) 0.0497 1.0000 Uani . . . . . . O5 O 0.34000(11) 0.5118(5) 0.49824(10) 0.0638 1.0000 Uani D . . . . . C6 C 0.17744(16) 0.6125(6) 0.55684(15) 0.0524 1.0000 Uani . . . . . . C61 C 0.14845(18) 0.7666(7) 0.46524(16) 0.0710 1.0000 Uani . . . . . . C7 C 0.10988(17) 0.5872(7) 0.62950(19) 0.0687 1.0000 Uani . . . . . . C8 C 0.13724(19) 0.4437(7) 0.71321(19) 0.0740 1.0000 Uani . . . . . . C9 C 0.23264(19) 0.3204(7) 0.72647(16) 0.0640 1.0000 Uani . . . . . . H1 H 0.606(2) 0.155(9) 0.600(2) 0.1158 1.0000 Uiso D . . . . . H3 H 0.4154 0.0803 0.7225 0.0664 1.0000 Uiso R . . . . . H5 H 0.3990(18) 0.425(7) 0.5127(18) 0.0968 1.0000 Uiso D . . . . . H611 H 0.0804 0.8541 0.4675 0.1060 1.0000 Uiso R . . . . . H612 H 0.1922 0.9549 0.4500 0.1061 1.0000 Uiso R . . . . . H613 H 0.1509 0.6031 0.4177 0.1058 1.0000 Uiso R . . . . . H7 H 0.0434 0.6736 0.6190 0.0810 1.0000 Uiso R . . . . . H8 H 0.0911 0.4301 0.7613 0.0886 1.0000 Uiso R . . . . . H9 H 0.2513 0.2154 0.7839 0.0767 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 O1 0.0634(12) 0.1045(16) 0.0642(12) 0.0189(11) 0.0061(8) 0.0204(12) N2 0.0532(11) 0.0722(15) 0.0486(11) 0.0040(11) 0.0022(9) 0.0083(12) C3 0.0664(16) 0.0573(17) 0.0433(13) 0.0017(13) 0.0017(12) -0.0027(14) C4 0.0522(14) 0.0543(17) 0.0427(13) -0.0054(12) 0.0026(11) -0.0055(12) C5 0.0516(14) 0.0556(17) 0.0420(13) -0.0111(12) 0.0041(10) -0.0057(13) O5 0.0573(10) 0.0905(14) 0.0437(9) 0.0069(10) 0.0085(8) 0.0097(10) C6 0.0504(14) 0.0526(16) 0.0543(14) -0.0128(13) -0.0014(11) -0.0031(13) C61 0.0715(17) 0.0762(19) 0.0651(17) -0.0089(16) -0.0103(13) 0.0109(15) C7 0.0535(15) 0.083(2) 0.0699(18) -0.0172(17) 0.0031(13) 0.0011(15) C8 0.0619(17) 0.096(2) 0.0648(18) -0.0130(18) 0.0202(13) -0.0117(17) C9 0.0683(17) 0.076(2) 0.0475(13) -0.0051(14) 0.0103(12) -0.0172(15) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.006(7) 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 O1 . N2 . 1.393(2) yes O1 . H1 . 0.81(3) no N2 . C3 . 1.271(2) yes C3 . C4 . 1.445(3) yes C3 . H3 . 0.912 no C4 . C5 . 1.402(3) yes C4 . C9 . 1.401(3) yes C5 . O5 . 1.375(2) yes C5 . C6 . 1.381(3) yes O5 . H5 . 0.88(2) no C6 . C61 . 1.501(3) yes C6 . C7 . 1.385(3) yes C61 . H611 . 0.967 no C61 . H612 . 0.969 no C61 . H613 . 0.942 no C7 . C8 . 1.379(4) yes C7 . H7 . 0.956 no C8 . C9 . 1.367(3) yes C8 . H8 . 0.928 no C9 . H9 . 0.957 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 N2 . O1 . H1 . 107(2) no O1 . N2 . C3 . 113.1(2) yes N2 . C3 . C4 . 121.5(2) yes N2 . C3 . H3 . 120.5 no C4 . C3 . H3 . 117.9 no C3 . C4 . C5 . 122.62(19) yes C3 . C4 . C9 . 119.6(2) yes C5 . C4 . C9 . 117.7(2) yes C4 . C5 . O5 . 120.5(2) yes C4 . C5 . C6 . 122.4(2) yes O5 . C5 . C6 . 117.1(2) yes C5 . O5 . H5 . 111.4(16) no C5 . C6 . C61 . 120.4(2) yes C5 . C6 . C7 . 117.6(2) yes C61 . C6 . C7 . 122.0(2) yes C6 . C61 . H611 . 110.5 no C6 . C61 . H612 . 111.1 no H611 . C61 . H612 . 107.0 no C6 . C61 . H613 . 110.5 no H611 . C61 . H613 . 107.7 no H612 . C61 . H613 . 109.8 no C6 . C7 . C8 . 121.5(2) yes C6 . C7 . H7 . 117.0 no C8 . C7 . H7 . 121.5 no C7 . C8 . C9 . 120.5(2) yes C7 . C8 . H8 . 120.3 no C9 . C8 . H8 . 119.2 no C4 . C9 . C8 . 120.3(3) yes C4 . C9 . H9 . 119.0 no C8 . C9 . H9 . 120.6 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O5 0.81(3) 2.06(3) 2.806(3) 153(3) 3_666 yes O5 H5 N2 0.88(2) 1.85(3) 2.608(3) 143(2) . yes _chemical_name_common 3-Methylsalicylaldoxime # Attachment 'L3Hrevised.cif' data_L3H _database_code_depnum_ccdc_archive 'CCDC 656842' _audit_update_record ; 2007-08-03 # Formatted by publCIF ; _chemical_compound_source 'R. Forgan' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of hexane/chloroform solution' _audit_creation_date 07-01-16 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-tButylsalicylaldoxime _chemical_melting_point ? _cell_length_a 6.6132(3) _cell_length_b 13.1087(6) _cell_length_c 13.6382(6) _cell_angle_alpha 68.762(3) _cell_angle_beta 76.739(3) _cell_angle_gamma 79.733(3) _cell_volume 1066.71(9) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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' _cell_formula_units_Z 4 # Given Formula = C11 H15 N1 O2 # Dc = 1.20 Fooo = 416.00 Mu = 0.83 M = 386.49 # Found Formula = C11 H15 N1 O2 # Dc = 1.20 FOOO = 416.00 Mu = 0.83 M = 386.49 _chemical_formula_sum 'C11 H15 N1 O2' _chemical_formula_moiety 'C11 H15 N1 O2' _chemical_formula_weight 193.25 _cell_measurement_reflns_used 3946 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.45 _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.083 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details ; Data collection strategy optimised with COSMO. ; _diffrn_measurement_device_type 'Bruker SMART Apex CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _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_ambient_temperature 298 _diffrn_reflns_number 23029 _reflns_number_total 4351 _diffrn_reflns_av_R_equivalents 0.050 # Number of reflections with Friedels Law is 4351 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4362 _diffrn_reflns_theta_min 1.628 _diffrn_reflns_theta_max 26.370 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.370 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -7 _reflns_limit_h_max 8 _reflns_limit_k_min -14 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.15 _refine_diff_density_max 0.17 _refine_ls_number_reflns 4351 _refine_ls_number_restraints 4 _refine_ls_number_parameters 265 #_refine_ls_R_factor_ref 0.1206 _refine_ls_wR_factor_ref 0.1344 _refine_ls_goodness_of_fit_ref 0.8468 #_reflns_number_all 4351 _refine_ls_R_factor_all 0.1206 _refine_ls_wR_factor_all 0.1344 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2393 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_gt 0.1093 _refine_ls_shift/su_max 0.000129 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # 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: 49.8 79.1 46.6 17.4 3.09 ; _refine_special_details ; The hydrogens were placed geometrically except for H11, H51, H12 and H52 (on O11, O51, O12 and O52 respectively) which were found in a Fourier difference map and then their positions were refined subject to an O-H distance restraint of 0.84 Angstroms. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Checkcif Output: 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 Sadabs corrects for all systematic errors that lead to disparities in the intensities of equivalent data. It is possible that the larger than expected range of transmission is accounted for by crystal decay or absorption by the mounting fibre. 720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 18 795_ALERT_4_C C-Atom in CIF Coordinate List out of Sequence .. C71 796_ALERT_4_C O-Atom in CIF Coordinate List out of Sequence .. O12 The atom labels and list given are intended to be more chemically significant. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 1.000 2247 2246 1 23.01 0.550 1.000 2976 2975 1 25.24 0.600 1.000 3859 3858 1 #----------------------------------------------------------- ACTA Min. Res. ---- 26.37 0.625 0.998 4359 4351 8 ; # End of 'script/refcif.dat' 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 O11 O 0.9449(3) 0.10056(16) -0.20317(13) 0.0634 1.0000 Uani D . . . . . N21 N 0.8262(3) 0.09160(16) -0.10161(14) 0.0482 1.0000 Uani . . . . . . C31 C 0.6417(4) 0.13697(19) -0.10563(18) 0.0463 1.0000 Uani . . . . . . C41 C 0.4914(4) 0.14192(18) -0.01058(17) 0.0418 1.0000 Uani . . . . . . C51 C 0.5413(4) 0.09676(18) 0.09266(17) 0.0411 1.0000 Uani . . . . . . O51 O 0.7349(3) 0.04363(15) 0.10460(13) 0.0528 1.0000 Uani D . . . . . C61 C 0.3968(4) 0.10661(18) 0.18236(18) 0.0436 1.0000 Uani . . . . . . C611 C 0.4507(4) 0.0595(2) 0.29553(18) 0.0508 1.0000 Uani . . . . . . C621 C 0.4983(5) -0.0654(2) 0.3287(2) 0.0636 1.0000 Uani . . . . . . C631 C 0.6384(5) 0.1113(3) 0.2982(2) 0.0711 1.0000 Uani . . . . . . C641 C 0.2685(5) 0.0854(3) 0.3781(2) 0.0865 1.0000 Uani . . . . . . C71 C 0.2015(4) 0.1603(2) 0.1645(2) 0.0539 1.0000 Uani . . . . . . C81 C 0.1483(4) 0.2033(2) 0.0636(2) 0.0580 1.0000 Uani . . . . . . C91 C 0.2922(4) 0.1947(2) -0.0227(2) 0.0528 1.0000 Uani . . . . . . O12 O 0.3935(3) 0.35526(17) 0.69217(14) 0.0692 1.0000 Uani D . . . . . N22 N 0.3353(3) 0.38425(17) 0.59240(14) 0.0506 1.0000 Uani . . . . . . C32 C 0.1858(4) 0.33375(19) 0.59647(17) 0.0465 1.0000 Uani . . . . . . C42 C 0.1000(4) 0.34935(18) 0.50195(17) 0.0416 1.0000 Uani . . . . . . C52 C 0.1856(3) 0.41574(18) 0.39947(17) 0.0389 1.0000 Uani . . . . . . O52 O 0.3523(3) 0.46995(14) 0.38685(12) 0.0537 1.0000 Uani D . . . . . C62 C 0.1057(3) 0.42575(18) 0.30902(17) 0.0405 1.0000 Uani . . . . . . C612 C 0.2056(4) 0.4930(2) 0.19534(17) 0.0472 1.0000 Uani . . . . . . C622 C 0.1907(5) 0.6143(2) 0.1837(2) 0.0637 1.0000 Uani . . . . . . C632 C 0.4321(5) 0.4471(3) 0.1702(2) 0.0755 1.0000 Uani . . . . . . C642 C 0.0928(5) 0.4885(2) 0.1108(2) 0.0665 1.0000 Uani . . . . . . C72 C -0.0681(4) 0.3711(2) 0.3282(2) 0.0543 1.0000 Uani . . . . . . C82 C -0.1579(4) 0.3076(2) 0.4287(2) 0.0604 1.0000 Uani . . . . . . C92 C -0.0732(4) 0.2959(2) 0.5149(2) 0.0549 1.0000 Uani . . . . . . H11 H 1.060(5) 0.058(3) -0.192(3) 0.0861 1.0000 Uiso D . . . . . H31 H 0.5979 0.1673 -0.1709 0.0549 1.0000 Uiso R . . . . . H51 H 0.806(4) 0.046(2) 0.042(2) 0.0747 1.0000 Uiso D . . . . . H6211 H 0.5365 -0.0903 0.3967 0.0919 1.0000 Uiso R . . . . . H6212 H 0.3728 -0.0970 0.3337 0.0918 1.0000 Uiso R . . . . . H6213 H 0.6108 -0.0875 0.2792 0.0915 1.0000 Uiso R . . . . . H6311 H 0.6663 0.0823 0.3697 0.1105 1.0000 Uiso R . . . . . H6312 H 0.6020 0.1892 0.2832 0.1108 1.0000 Uiso R . . . . . H6313 H 0.7615 0.0984 0.2488 0.1111 1.0000 Uiso R . . . . . H6411 H 0.3072 0.0550 0.4471 0.1239 1.0000 Uiso R . . . . . H6412 H 0.1480 0.0506 0.3809 0.1242 1.0000 Uiso R . . . . . H6413 H 0.2345 0.1632 0.3611 0.1248 1.0000 Uiso R . . . . . H71 H 0.1023 0.1672 0.2227 0.0637 1.0000 Uiso R . . . . . H81 H 0.0135 0.2381 0.0557 0.0686 1.0000 Uiso R . . . . . H91 H 0.2604 0.2237 -0.0906 0.0622 1.0000 Uiso R . . . . . H12 H 0.485(5) 0.400(3) 0.677(3) 0.1038 1.0000 Uiso D . . . . . H32 H 0.1257 0.2844 0.6619 0.0522 1.0000 Uiso R . . . . . H52 H 0.386(5) 0.457(2) 0.447(2) 0.0814 1.0000 Uiso D . . . . . H6221 H 0.2640 0.6533 0.1142 0.0967 1.0000 Uiso R . . . . . H6222 H 0.0444 0.6441 0.1892 0.0966 1.0000 Uiso R . . . . . H6223 H 0.2507 0.6240 0.2374 0.0962 1.0000 Uiso R . . . . . H6321 H 0.4949 0.4926 0.1010 0.1060 1.0000 Uiso R . . . . . H6322 H 0.4402 0.3731 0.1691 0.1066 1.0000 Uiso R . . . . . H6323 H 0.5083 0.4464 0.2220 0.1063 1.0000 Uiso R . . . . . H6421 H 0.1602 0.5332 0.0413 0.1045 1.0000 Uiso R . . . . . H6422 H -0.0542 0.5162 0.1234 0.1038 1.0000 Uiso R . . . . . H6423 H 0.1001 0.4133 0.1124 0.1040 1.0000 Uiso R . . . . . H72 H -0.1236 0.3759 0.2694 0.0671 1.0000 Uiso R . . . . . H82 H -0.2756 0.2742 0.4381 0.0747 1.0000 Uiso R . . . . . H92 H -0.1275 0.2517 0.5829 0.0656 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 O11 0.0661(12) 0.0697(13) 0.0367(9) -0.0051(8) -0.0023(8) 0.0010(10) N21 0.0574(13) 0.0472(11) 0.0318(10) -0.0033(8) -0.0057(9) -0.0095(10) C31 0.0591(16) 0.0414(13) 0.0367(12) -0.0021(10) -0.0184(11) -0.0116(12) C41 0.0507(14) 0.0349(11) 0.0389(12) -0.0062(9) -0.0109(10) -0.0112(10) C51 0.0451(13) 0.0378(12) 0.0407(12) -0.0085(9) -0.0129(10) -0.0084(10) O51 0.0467(10) 0.0665(11) 0.0377(9) -0.0111(8) -0.0109(7) 0.0037(8) C61 0.0481(14) 0.0418(13) 0.0422(13) -0.0119(10) -0.0113(11) -0.0083(11) C611 0.0567(15) 0.0558(15) 0.0376(13) -0.0139(11) -0.0085(11) -0.0040(12) C621 0.080(2) 0.0601(17) 0.0437(14) -0.0060(12) -0.0125(13) -0.0115(14) C631 0.093(2) 0.0736(19) 0.0553(16) -0.0182(14) -0.0307(16) -0.0155(17) C641 0.089(2) 0.118(3) 0.0425(16) -0.0285(16) -0.0100(15) 0.016(2) C71 0.0478(15) 0.0599(16) 0.0521(15) -0.0179(12) -0.0081(12) -0.0037(12) C81 0.0476(15) 0.0603(17) 0.0638(17) -0.0161(13) -0.0200(13) 0.0032(12) C91 0.0598(17) 0.0521(15) 0.0460(14) -0.0071(11) -0.0234(12) -0.0065(12) O12 0.0902(15) 0.0802(14) 0.0371(9) 0.0028(9) -0.0278(9) -0.0356(11) N22 0.0617(13) 0.0556(12) 0.0322(10) -0.0024(9) -0.0159(9) -0.0170(10) C32 0.0565(15) 0.0450(13) 0.0318(11) -0.0056(10) -0.0021(10) -0.0128(11) C42 0.0443(13) 0.0421(12) 0.0393(12) -0.0140(10) -0.0078(10) -0.0057(10) C52 0.0385(12) 0.0401(12) 0.0413(12) -0.0148(10) -0.0108(10) -0.0045(10) O52 0.0602(11) 0.0682(12) 0.0347(8) -0.0040(8) -0.0171(8) -0.0290(9) C62 0.0433(13) 0.0416(12) 0.0410(12) -0.0168(10) -0.0139(10) -0.0009(10) C612 0.0556(15) 0.0539(14) 0.0364(12) -0.0147(10) -0.0180(11) -0.0049(11) C622 0.095(2) 0.0521(16) 0.0474(15) -0.0088(12) -0.0262(14) -0.0175(15) C632 0.0642(19) 0.106(2) 0.0437(15) -0.0167(15) -0.0065(13) 0.0008(17) C642 0.085(2) 0.0743(19) 0.0505(15) -0.0206(14) -0.0297(14) -0.0110(16) C72 0.0523(15) 0.0625(17) 0.0572(16) -0.0241(13) -0.0213(12) -0.0053(13) C82 0.0496(15) 0.0706(18) 0.0674(18) -0.0230(15) -0.0106(13) -0.0230(13) C92 0.0543(16) 0.0597(16) 0.0498(14) -0.0147(12) -0.0032(12) -0.0197(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.848(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 O11 . N21 . 1.402(3) yes O11 . H11 . 0.87(3) no N21 . C31 . 1.263(3) yes C31 . C41 . 1.456(3) yes C31 . H31 . 0.925 no C41 . C51 . 1.408(3) yes C41 . C91 . 1.390(3) yes C51 . O51 . 1.359(3) yes C51 . C61 . 1.400(3) yes O51 . H51 . 0.86(3) no C61 . C611 . 1.541(3) yes C61 . C71 . 1.385(3) yes C611 . C621 . 1.526(4) yes C611 . C631 . 1.531(4) yes C611 . C641 . 1.531(4) yes C621 . H6211 . 0.943 no C621 . H6212 . 0.970 no C621 . H6213 . 0.964 no C631 . H6311 . 0.959 no C631 . H6312 . 0.962 no C631 . H6313 . 0.963 no C641 . H6411 . 0.956 no C641 . H6412 . 0.973 no C641 . H6413 . 0.957 no C71 . C81 . 1.387(4) yes C71 . H71 . 0.928 no C81 . C91 . 1.360(4) yes C81 . H81 . 0.937 no C91 . H91 . 0.923 no O12 . N22 . 1.399(2) yes O12 . H12 . 0.86(3) no N22 . C32 . 1.265(3) yes C32 . C42 . 1.459(3) yes C32 . H32 . 0.940 no C42 . C52 . 1.401(3) yes C42 . C92 . 1.392(3) yes C52 . O52 . 1.362(3) yes C52 . C62 . 1.405(3) yes O52 . H52 . 0.85(3) no C62 . C612 . 1.538(3) yes C62 . C72 . 1.387(3) yes C612 . C622 . 1.527(4) yes C612 . C632 . 1.522(4) yes C612 . C642 . 1.533(3) yes C622 . H6221 . 0.959 no C622 . H6222 . 0.973 no C622 . H6223 . 0.965 no C632 . H6321 . 0.959 no C632 . H6322 . 0.967 no C632 . H6323 . 0.954 no C642 . H6421 . 0.968 no C642 . H6422 . 0.974 no C642 . H6423 . 0.971 no C72 . C82 . 1.379(4) yes C72 . H72 . 0.933 no C82 . C92 . 1.363(4) yes C82 . H82 . 0.922 no C92 . H92 . 0.926 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 N21 . O11 . H11 . 106(2) no O11 . N21 . C31 . 112.50(19) yes N21 . C31 . C41 . 122.5(2) yes N21 . C31 . H31 . 119.5 no C41 . C31 . H31 . 118.0 no C31 . C41 . C51 . 122.5(2) yes C31 . C41 . C91 . 118.6(2) yes C51 . C41 . C91 . 119.0(2) yes C41 . C51 . O51 . 118.9(2) yes C41 . C51 . C61 . 121.4(2) yes O51 . C51 . C61 . 119.74(19) yes C51 . O51 . H51 . 108.6(20) no C51 . C61 . C611 . 121.9(2) yes C51 . C61 . C71 . 116.6(2) yes C611 . C61 . C71 . 121.4(2) yes C61 . C611 . C621 . 110.3(2) yes C61 . C611 . C631 . 109.8(2) yes C621 . C611 . C631 . 110.2(2) yes C61 . C611 . C641 . 111.3(2) yes C621 . C611 . C641 . 107.7(2) yes C631 . C611 . C641 . 107.4(2) yes C611 . C621 . H6211 . 107.4 no C611 . C621 . H6212 . 108.8 no H6211 . C621 . H6212 . 109.2 no C611 . C621 . H6213 . 112.1 no H6211 . C621 . H6213 . 109.2 no H6212 . C621 . H6213 . 110.1 no C611 . C631 . H6311 . 108.2 no C611 . C631 . H6312 . 109.3 no H6311 . C631 . H6312 . 106.2 no C611 . C631 . H6313 . 113.1 no H6311 . C631 . H6313 . 110.1 no H6312 . C631 . H6313 . 109.8 no C611 . C641 . H6411 . 109.0 no C611 . C641 . H6412 . 109.6 no H6411 . C641 . H6412 . 107.6 no C611 . C641 . H6413 . 110.7 no H6411 . C641 . H6413 . 109.2 no H6412 . C641 . H6413 . 110.6 no C61 . C71 . C81 . 122.8(2) yes C61 . C71 . H71 . 118.3 no C81 . C71 . H71 . 118.9 no C71 . C81 . C91 . 119.7(2) yes C71 . C81 . H81 . 119.6 no C91 . C81 . H81 . 120.7 no C41 . C91 . C81 . 120.6(2) yes C41 . C91 . H91 . 118.5 no C81 . C91 . H91 . 121.0 no N22 . O12 . H12 . 101(2) no O12 . N22 . C32 . 112.25(18) yes N22 . C32 . C42 . 122.2(2) yes N22 . C32 . H32 . 120.1 no C42 . C32 . H32 . 117.7 no C32 . C42 . C52 . 122.4(2) yes C32 . C42 . C92 . 118.4(2) yes C52 . C42 . C92 . 119.2(2) yes C42 . C52 . O52 . 119.39(18) yes C42 . C52 . C62 . 121.4(2) yes O52 . C52 . C62 . 119.24(19) yes C52 . O52 . H52 . 110(2) no C52 . C62 . C612 . 122.0(2) yes C52 . C62 . C72 . 116.1(2) yes C612 . C62 . C72 . 121.9(2) yes C62 . C612 . C622 . 110.52(19) yes C62 . C612 . C632 . 109.9(2) yes C622 . C612 . C632 . 110.8(2) yes C62 . C612 . C642 . 111.8(2) yes C622 . C612 . C642 . 106.2(2) yes C632 . C612 . C642 . 107.5(2) yes C612 . C622 . H6221 . 108.8 no C612 . C622 . H6222 . 108.7 no H6221 . C622 . H6222 . 108.6 no C612 . C622 . H6223 . 111.5 no H6221 . C622 . H6223 . 109.1 no H6222 . C622 . H6223 . 110.1 no C612 . C632 . H6321 . 109.0 no C612 . C632 . H6322 . 110.6 no H6321 . C632 . H6322 . 108.4 no C612 . C632 . H6323 . 110.7 no H6321 . C632 . H6323 . 108.9 no H6322 . C632 . H6323 . 109.2 no C612 . C642 . H6421 . 108.2 no C612 . C642 . H6422 . 111.2 no H6421 . C642 . H6422 . 109.6 no C612 . C642 . H6423 . 110.5 no H6421 . C642 . H6423 . 109.6 no H6422 . C642 . H6423 . 107.7 no C62 . C72 . C82 . 123.3(2) yes C62 . C72 . H72 . 117.9 no C82 . C72 . H72 . 118.8 no C72 . C82 . C92 . 119.5(2) yes C72 . C82 . H82 . 120.5 no C92 . C82 . H82 . 120.0 no C42 . C92 . C82 . 120.4(2) yes C42 . C92 . H92 . 118.4 no C82 . C92 . H92 . 121.2 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O11 H11 O51 0.87(4) 2.00(4) 2.811(3) 156(3) 2_755 yes O12 H12 O52 0.86(4) 1.99(4) 2.827(3) 164(4) 2_666 yes O51 H51 N21 0.87(3) 1.81(3) 2.597(2) 150(3) . yes O52 H52 N22 0.85(3) 1.84(3) 2.599(2) 148(3) . yes C621 H6213 O51 0.9600 2.4400 3.045(3) 121.00 . yes C631 H6313 O51 0.9600 2.3800 2.981(4) 120.00 . yes C622 H6223 O52 0.9600 2.4200 3.039(3) 122.00 . yes C632 H6323 O52 0.9500 2.3500 2.995(3) 124.00 . yes _chemical_name_common 3-tButylsalicylaldoxime # Attachment 'L4Hrevised.cif' data_L4H _database_code_depnum_ccdc_archive 'CCDC 656840' _audit_update_record ; 2007-08-03 # Formatted by publCIF ; _chemical_compound_source 'R. Forgan' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of chloroform solution' _audit_creation_date 05-12-08 _audit_creation_method CRYSTALS_ver_12.82 _chemical_name_systematic 3-Methoxysalicylaldoxime _chemical_melting_point ? _cell_length_a 13.9108(5) _cell_length_b 7.1936(3) _cell_length_c 15.6965(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1570.73(11) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 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' _cell_formula_units_Z 8 # Given Formula = C7 H9 N1 O3 # Dc = 1.31 Fooo = 704.00 Mu = 1.04 M = 155.15 # Found Formula = C8 H9 N1 O3 # Dc = 1.41 FOOO = 704.00 Mu = 1.09 M = 167.16 _chemical_formula_sum 'C8 H9 N1 O3' _chemical_formula_moiety 'C8 H9 N1 O3' _chemical_formula_weight 167.16 _cell_measurement_reflns_used 1913 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.109 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details ; Used Oxford Cryosystems low temperature device. ; _diffrn_measurement_device_type 'Bruker SMART Apex CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _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_ambient_temperature 298 _diffrn_reflns_number 17158 _reflns_number_total 1615 _diffrn_reflns_av_R_equivalents 0.027 # Number of reflections with Friedels Law is 1615 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1631 _diffrn_reflns_theta_min 2.595 _diffrn_reflns_theta_max 26.517 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.986 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min 0 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.12 _refine_diff_density_max 0.16 _refine_ls_number_reflns 1615 _refine_ls_number_restraints 2 _refine_ls_number_parameters 115 #_refine_ls_R_factor_ref 0.0810 _refine_ls_wR_factor_ref 0.1256 _refine_ls_goodness_of_fit_ref 1.1328 #_reflns_number_all 1615 _refine_ls_R_factor_all 0.0810 _refine_ls_wR_factor_all 0.1256 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 793 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_gt 0.0746 _refine_ls_shift/su_max 0.000201 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # 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: 38.2 60.0 34.6 12.9 1.19 ; _refine_special_details ; The hydrogens were placed geometrically except for H1 and H5 (on O1 and O5 respectively) which were found in a Fourier difference map and then their positions were refined subject to an O-H distance restraint of 0.84 Angstroms. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Checkcif Output: 026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. The crystal used was very small as it was intended to be used for a high pressure compression study and thus had to be small enough to fit in the diamond anvil cell. As such there seems to be relatively few intense reflections in the dataset. 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78 Sadabs corrects for all systematic errors that lead to disparities in the intensities of equivalent data. It is possible that the larger than expected range of transmission is accounted for by crystal decay or absorption by the mounting fibre. 795_ALERT_4_C C-Atom in CIF Coordinate List out of Sequence .. C7 The atom list given is intended to be more chemically significant. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 1.000 820 820 0 23.01 0.550 1.000 1085 1085 0 25.24 0.600 1.000 1426 1426 0 #----------------------------------------------------------- ACTA Min. Res. ---- 26.52 0.628 0.993 1626 1615 11 ; # End of 'script/refcif.dat' 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 O1 O 0.48465(14) -0.0109(3) 0.67399(10) 0.0398 1.0000 Uani D . . . . . N2 N 0.52591(15) 0.1051(3) 0.61253(13) 0.0305 1.0000 Uani . . . . . . C3 C 0.55412(16) 0.2605(4) 0.64192(16) 0.0312 1.0000 Uani . . . . . . C4 C 0.59609(16) 0.3988(3) 0.58484(15) 0.0276 1.0000 Uani . . . . . . C5 C 0.60837(17) 0.3635(3) 0.49795(16) 0.0268 1.0000 Uani . . . . . . O5 O 0.58585(13) 0.1967(2) 0.46236(11) 0.0330 1.0000 Uani D . . . . . C6 C 0.64463(16) 0.5009(3) 0.44381(16) 0.0301 1.0000 Uani . . . . . . O61 O 0.65143(12) 0.4492(3) 0.36008(11) 0.0364 1.0000 Uani . . . . . . C62 C 0.6941(2) 0.5805(4) 0.30307(18) 0.0436 1.0000 Uani . . . . . . C7 C 0.67093(18) 0.6709(4) 0.47694(17) 0.0338 1.0000 Uani . . . . . . C8 C 0.66042(18) 0.7057(4) 0.56397(18) 0.0376 1.0000 Uani . . . . . . C9 C 0.62294(18) 0.5730(4) 0.61711(17) 0.0336 1.0000 Uani . . . . . . H1 H 0.460(2) -0.098(4) 0.641(2) 0.0602 1.0000 Uiso D . . . . . H3 H 0.5475 0.2877 0.7006 0.0381 1.0000 Uiso R . . . . . H5 H 0.566(2) 0.128(4) 0.505(2) 0.0500 1.0000 Uiso D . . . . . H621 H 0.6936 0.5244 0.2466 0.0651 1.0000 Uiso R . . . . . H622 H 0.7592 0.6101 0.3194 0.0656 1.0000 Uiso R . . . . . H623 H 0.6565 0.6949 0.3029 0.0654 1.0000 Uiso R . . . . . H7 H 0.6959 0.7626 0.4415 0.0408 1.0000 Uiso R . . . . . H8 H 0.6785 0.8220 0.5870 0.0446 1.0000 Uiso R . . . . . H9 H 0.6147 0.5979 0.6758 0.0406 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 O1 0.0569(11) 0.0381(10) 0.0243(8) 0.0004(8) 0.0035(8) -0.0126(9) N2 0.0374(11) 0.0299(11) 0.0241(9) 0.0020(9) 0.0011(9) -0.0010(10) C3 0.0318(13) 0.0352(14) 0.0265(11) -0.0049(11) -0.0017(10) 0.0015(11) C4 0.0229(11) 0.0296(13) 0.0302(12) -0.0013(10) -0.0025(10) 0.0024(10) C5 0.0225(11) 0.0250(12) 0.0329(12) -0.0014(11) -0.0029(9) 0.0008(9) O5 0.0428(10) 0.0296(9) 0.0266(9) -0.0021(8) 0.0016(8) -0.0088(8) C6 0.0239(11) 0.0324(13) 0.0339(12) 0.0020(11) -0.0021(10) 0.0035(10) O61 0.0422(10) 0.0379(10) 0.0291(9) 0.0052(8) 0.0019(7) -0.0069(9) C62 0.0455(15) 0.0471(17) 0.0381(14) 0.0113(14) 0.0048(13) -0.0063(13) C7 0.0290(13) 0.0278(13) 0.0446(15) 0.0044(12) 0.0020(11) -0.0009(11) C8 0.0327(13) 0.0280(14) 0.0522(16) -0.0110(12) -0.0001(12) -0.0016(10) C9 0.0305(12) 0.0341(14) 0.0362(13) -0.0084(12) 0.0008(11) 0.0004(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5387(19) 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 O1 . N2 . 1.398(3) yes O1 . H1 . 0.89(3) no N2 . C3 . 1.272(3) yes C3 . C4 . 1.460(4) yes C3 . H3 . 0.947 no C4 . C5 . 1.398(4) yes C4 . C9 . 1.402(3) yes C5 . O5 . 1.361(3) yes C5 . C6 . 1.397(3) yes O5 . H5 . 0.87(3) no C6 . O61 . 1.369(3) yes C6 . C7 . 1.379(4) yes O61 . C62 . 1.430(3) yes C62 . H621 . 0.973 no C62 . H622 . 0.965 no C62 . H623 . 0.975 no C7 . C8 . 1.396(4) yes C7 . H7 . 0.929 no C8 . C9 . 1.371(4) yes C8 . H8 . 0.945 no C9 . H9 . 0.945 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 N2 . O1 . H1 . 100(2) no O1 . N2 . C3 . 113.6(2) yes N2 . C3 . C4 . 120.0(2) yes N2 . C3 . H3 . 120.3 no C4 . C3 . H3 . 119.7 no C3 . C4 . C5 . 121.6(2) yes C3 . C4 . C9 . 119.6(2) yes C5 . C4 . C9 . 118.8(2) yes C4 . C5 . O5 . 122.2(2) yes C4 . C5 . C6 . 120.6(2) yes O5 . C5 . C6 . 117.2(2) yes C5 . O5 . H5 . 105(2) no C5 . C6 . O61 . 114.6(2) yes C5 . C6 . C7 . 119.6(2) yes O61 . C6 . C7 . 125.8(2) yes C6 . O61 . C62 . 116.8(2) yes O61 . C62 . H621 . 107.0 no O61 . C62 . H622 . 111.6 no H621 . C62 . H622 . 109.9 no O61 . C62 . H623 . 109.7 no H621 . C62 . H623 . 110.1 no H622 . C62 . H623 . 108.5 no C6 . C7 . C8 . 120.0(2) yes C6 . C7 . H7 . 120.2 no C8 . C7 . H7 . 119.8 no C7 . C8 . C9 . 120.7(2) yes C7 . C8 . H8 . 120.3 no C9 . C8 . H8 . 119.0 no C4 . C9 . C8 . 120.3(2) yes C4 . C9 . H9 . 119.3 no C8 . C9 . H9 . 120.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O5 0.88(3) 1.88(3) 2.707(2) 155(3) 5_656 yes O5 H5 N2 0.88(3) 1.79(3) 2.586(3) 151(3) . yes C3 H3 O1 0.9500 2.4800 3.368(3) 155.00 4_656 yes _chemical_name_common 3-Methoxysalicylaldoxime # Attachment 'L5Hrevised.cif' data_L5H _database_code_depnum_ccdc_archive 'CCDC 656839' _audit_update_record ; 2007-08-03 # Formatted by publCIF ; _chemical_compound_source 'R. Forgan' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of dichloromethane solution' _audit_creation_date 05-10-11 _audit_creation_method CRYSTALS_ver_12.82 _chemical_name_systematic 3-chlorosalicylaldoxime _chemical_melting_point ? _cell_length_a 13.1506(18) _cell_length_b 3.8859(6) _cell_length_c 14.3115(19) _cell_angle_alpha 90 _cell_angle_beta 91.548(10) _cell_angle_gamma 90 _cell_volume 731.08(18) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C7 H6 Cl1 N1 O2 # Dc = 1.56 Fooo = 352.00 Mu = 4.63 M = 171.58 # Found Formula = C7 H6 Cl1 N1 O2 # Dc = 1.56 FOOO = 352.00 Mu = 4.63 M = 171.58 _chemical_formula_sum 'C7 H6 Cl1 N1 O2' _chemical_formula_moiety 'C7 H6 Cl1 N1 O2' _chemical_formula_weight 171.58 _cell_measurement_reflns_used 2398 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.19 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.24 _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.463 # Sheldrick geometric approximatio 0.90 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.92 _exptl_special_details ; Data collection strategy optimised with COSMO. ; _diffrn_measurement_device_type 'Bruker SMART Apex CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _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_ambient_temperature 298 _diffrn_reflns_number 10310 _reflns_number_total 1955 _diffrn_reflns_av_R_equivalents 0.018 # Number of reflections with Friedels Law is 1955 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2080 _diffrn_reflns_theta_min 2.848 _diffrn_reflns_theta_max 29.726 _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 28.240 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 5 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.12 _refine_diff_density_max 0.21 _refine_ls_number_reflns 1955 _refine_ls_number_restraints 2 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.0618 _refine_ls_wR_factor_ref 0.0831 _refine_ls_goodness_of_fit_ref 0.8005 #_reflns_number_all 1955 _refine_ls_R_factor_all 0.0618 _refine_ls_wR_factor_all 0.0831 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 1127 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_gt 0.0786 _refine_ls_shift/su_max 0.000597 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.00P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The hydrogen atoms were placed geometrically except for those on oxygen atoms (H1 and H5) which were found in a Fourier difference map and then their positions were refined subject to O-H distance restraints of 0.84 Angstroms. The remaining hydrogens which were placed geometrically were then constrained to ride on their host atom. Checkcif output: 912_ALERT_3_B # Missing FCF Reflections Above STH/L=0.6 ...... 128 910_ALERT_3_C # Missing FCF Reflections Below TH(Min) ........ 1 The dataset is 99.9% complete out to 0.77 Angstroms as shown below. 199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K The temperature given is correct. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.999 764 763 1 23.01 0.550 0.999 1024 1023 1 25.24 0.600 0.999 1334 1333 1 #----------------------------------------------------------- ACTA Min. Res. ---- 27.51 0.650 0.999 1671 1670 1 29.73 0.698 0.938 2084 1955 129 ; 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 O1 O -0.06345(9) -0.4133(4) 0.85486(8) 0.0671 1.0000 Uani D . . . . . N2 N 0.02828(9) -0.2715(3) 0.88862(8) 0.0517 1.0000 Uani . . . . . . C3 C 0.10015(11) -0.3086(4) 0.83200(10) 0.0489 1.0000 Uani . . . . . . C4 C 0.20135(10) -0.1724(4) 0.85549(9) 0.0453 1.0000 Uani . . . . . . C5 C 0.22348(10) -0.0185(4) 0.94221(9) 0.0449 1.0000 Uani . . . . . . O5 O 0.15290(8) 0.0132(3) 1.00854(7) 0.0581 1.0000 Uani D . . . . . C6 C 0.32106(11) 0.1050(4) 0.96130(10) 0.0491 1.0000 Uani . . . . . . Cl6 Cl 0.34624(3) 0.28855(11) 1.07007(3) 0.0642 1.0000 Uani . . . . . . C7 C 0.39604(12) 0.0804(4) 0.89671(12) 0.0575 1.0000 Uani . . . . . . C8 C 0.37429(12) -0.0693(4) 0.81102(12) 0.0614 1.0000 Uani . . . . . . C9 C 0.27800(12) -0.1953(4) 0.79045(10) 0.0554 1.0000 Uani . . . . . . H1 H -0.1009(18) -0.346(6) 0.8905(15) 0.1020 1.0000 Uiso D . . . . . H3 H 0.0895 -0.4198 0.7740 0.0602 1.0000 Uiso R . . . . . H5 H 0.1005(13) -0.069(6) 0.9869(12) 0.0871 1.0000 Uiso D . . . . . H7 H 0.4624 0.1691 0.9127 0.0685 1.0000 Uiso R . . . . . H8 H 0.4236 -0.0858 0.7671 0.0735 1.0000 Uiso R . . . . . H9 H 0.2611 -0.2957 0.7302 0.0662 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 O1 0.0546(7) 0.0776(8) 0.0691(8) -0.0165(7) 0.0051(5) -0.0155(6) N2 0.0478(7) 0.0538(7) 0.0536(7) -0.0022(6) 0.0004(6) -0.0044(6) C3 0.0569(9) 0.0441(8) 0.0456(7) 0.0012(7) 0.0023(7) 0.0036(7) C4 0.0477(8) 0.0404(7) 0.0482(8) 0.0063(6) 0.0045(6) 0.0090(6) C5 0.0436(8) 0.0419(7) 0.0493(8) 0.0079(7) 0.0059(6) 0.0066(6) O5 0.0474(6) 0.0730(8) 0.0542(6) -0.0083(6) 0.0078(5) -0.0049(6) C6 0.0480(8) 0.0427(8) 0.0566(8) 0.0097(7) -0.0006(7) 0.0045(7) Cl6 0.0599(3) 0.0645(3) 0.0675(3) -0.0014(2) -0.00932(19) -0.0027(2) C7 0.0437(8) 0.0553(9) 0.0735(11) 0.0156(8) 0.0038(7) 0.0049(7) C8 0.0525(10) 0.0653(10) 0.0673(10) 0.0121(9) 0.0176(8) 0.0125(8) C9 0.0626(9) 0.0531(9) 0.0509(8) 0.0055(7) 0.0092(7) 0.0111(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.036(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 O1 . N2 . 1.4002(16) yes O1 . H1 . 0.76(2) no N2 . C3 . 1.2696(18) yes C3 . C4 . 1.463(2) yes C3 . H3 . 0.942 no C4 . C5 . 1.4010(19) yes C4 . C9 . 1.393(2) yes C5 . O5 . 1.3511(17) yes C5 . C6 . 1.390(2) yes O5 . H5 . 0.813(17) no C6 . Cl6 . 1.7360(16) yes C6 . C7 . 1.373(2) yes C7 . C8 . 1.380(2) yes C7 . H7 . 0.960 no C8 . C9 . 1.382(2) yes C8 . H8 . 0.918 no C9 . H9 . 0.967 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 N2 . O1 . H1 . 101.5(19) no O1 . N2 . C3 . 112.61(12) yes N2 . C3 . C4 . 120.04(13) yes N2 . C3 . H3 . 121.3 no C4 . C3 . H3 . 118.7 no C3 . C4 . C5 . 121.59(13) yes C3 . C4 . C9 . 119.57(13) yes C5 . C4 . C9 . 118.84(14) yes C4 . C5 . O5 . 122.09(12) yes C4 . C5 . C6 . 119.34(13) yes O5 . C5 . C6 . 118.57(13) yes C5 . O5 . H5 . 106.8(14) no C5 . C6 . Cl6 . 118.09(12) yes C5 . C6 . C7 . 121.30(15) yes Cl6 . C6 . C7 . 120.61(12) yes C6 . C7 . C8 . 119.48(15) yes C6 . C7 . H7 . 118.6 no C8 . C7 . H7 . 121.9 no C7 . C8 . C9 . 120.35(15) yes C7 . C8 . H8 . 120.3 no C9 . C8 . H8 . 119.3 no C4 . C9 . C8 . 120.69(15) yes C4 . C9 . H9 . 117.9 no C8 . C9 . H9 . 121.4 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O5 0.77(2) 2.07(2) 2.7834(17) 156(2) 3_557 yes O5 H5 N2 0.813(18) 1.851(19) 2.5891(16) 150.3(17) . yes _chemical_name_common 3-chlorosalicylaldoxime