Supplementary data for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'S. Parsons' _publ_contact_author_address ; School of Chemistry University of Edinburgh Kings Buildings West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email S.PARSONS@ED.AC.UK _publ_section_title ; The Effect of Pressure and Substituents on the Size of Pseudo-Macrocyclic Cavities in Salicylaldoxime Ligands ; loop_ _publ_author_name 'Simon Parsons' 'Ross Forgan' 'Elna Pidcock' 'P. Tasker' 'John E. Warren' 'Peter A. Wook' data_Cl00kbar _database_code_depnum_ccdc_archive 'CCDC 656839' _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 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 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 _chemical_name_common 3-chlorosalicylaldoxime #END data_MeO00kbar _database_code_depnum_ccdc_archive 'CCDC 656840' _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' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 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 _chemical_name_common 3-Methoxysalicylaldoxime #END data_Me00kbar _database_code_depnum_ccdc_archive 'CCDC 656841' _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' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 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 _chemical_name_common 3-Methylsalicylaldoxime #END data_tBu00kbar _database_code_depnum_ccdc_archive 'CCDC 656842' _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' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 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 _chemical_name_common 3-tButylsalicylaldoxime #END data_Me13kbar _database_code_depnum_ccdc_archive 'CCDC 657063' _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 12.998(3) _cell_length_b 3.6988(5) _cell_length_c 13.9167(16) _cell_angle_alpha 90 _cell_angle_beta 90.99(2) _cell_angle_gamma 90 _cell_volume 669.0(2) _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 0.0000 0.0000 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 0.0010 0.0010 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 0.0030 0.0020 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 = 1.50 Fooo = 320.00 Mu = 1.09 M = 151.16 # Found Formula = C8 H9 N1 O2 # Dc = 1.50 FOOO = 320.00 Mu = 1.09 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 590 _cell_measurement_theta_min 4 _cell_measurement_theta_max 18 _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 1.501 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.109 # Sheldrick geometric approximatio 0.98 0.98 _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 0.98 _diffrn_measurement_device_type 'Bruker-Nonius ApexII CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.45770 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 1300000 _diffrn_reflns_number 6638 _reflns_number_total 878 _diffrn_reflns_av_R_equivalents 0.233 # Number of reflections with Friedels Law is 965 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2052 _diffrn_reflns_theta_min 3.671 _diffrn_reflns_theta_max 19.114 _diffrn_measured_fraction_theta_max 0.427 _diffrn_reflns_theta_full 15.865 _diffrn_measured_fraction_theta_full 0.464 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _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 -6 _reflns_limit_h_max 6 _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 -0.23 _refine_diff_density_max 0.22 _refine_ls_number_reflns 876 _refine_ls_number_restraints 2 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.1210 _refine_ls_wR_factor_ref 0.2116 _refine_ls_goodness_of_fit_ref 1.0159 #_reflns_number_all 876 _refine_ls_R_factor_all 0.1210 _refine_ls_wR_factor_all 0.2116 # 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 502 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_gt 0.1777 _refine_ls_shift/su_max 0.000124 # 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^) + ( 0.12P)^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: 020_ALERT_3_A The value of Rint is greater than 0.10 ......... 0.23 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.46 088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.26 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 213_ALERT_2_C Atom N2 has ADP max/min Ratio ............. 4.00 oblate 230_ALERT_2_C Hirshfeld Test Diff for O1 - N2 .. 5.59 su 230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.12 su 241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.52 This is probably due to the lack of information in one direction which occurs as a result of the Merrill-Bassett diamond-anvil cell shading a significant region of reciprocal space. The effect of this shading is often to cause a smearing out of electron density in one particular direction. 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 #------------------------------------------------------------------------------- 13.23 0.500 0.479 698 334 364 14.58 0.550 0.457 923 422 501 15.94 0.600 0.464 1219 566 653 #----------------------------------------------------------- ACTA Min. Res. ---- 17.31 0.650 0.441 1544 681 863 18.69 0.700 0.428 1912 819 1093 19.11 0.715 0.427 2055 878 1177 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.5676(6) 0.0569(9) 0.63626(17) 0.0500 1.0000 Uani D . . . . . N2 N 0.4738(6) 0.2126(8) 0.60941(18) 0.0263 1.0000 Uani . . . . . . C3 C 0.4055(7) 0.1744(9) 0.67248(19) 0.0471 1.0000 Uani . . . . . . C4 C 0.3019(7) 0.3172(8) 0.65689(19) 0.0329 1.0000 Uani . . . . . . C5 C 0.2696(8) 0.4789(9) 0.56934(18) 0.0474 1.0000 Uani . . . . . . O5 O 0.3376(5) 0.5013(6) 0.49422(14) 0.0368 1.0000 Uani D . . . . . C6 C 0.1722(8) 0.6102(10) 0.5553(2) 0.0320 1.0000 Uani . . . . . . C61 C 0.1409(7) 0.7720(9) 0.45932(19) 0.0503 1.0000 Uani . . . . . . C7 C 0.1032(7) 0.5865(9) 0.6310(2) 0.0394 1.0000 Uani . . . . . . C8 C 0.1350(9) 0.4352(12) 0.7187(2) 0.0588 1.0000 Uani . . . . . . C9 C 0.2309(8) 0.3040(11) 0.7310(2) 0.0475 1.0000 Uani . . . . . . H1 H 0.621(6) 0.141(17) 0.609(5) 0.0754 1.0000 Uiso D . . . . . H3 H 0.4221 0.0518 0.7293 0.0562 1.0000 Uiso R . . . . . H5 H 0.392(5) 0.384(13) 0.514(3) 0.0547 1.0000 Uiso D . . . . . H611 H 0.0751 0.8841 0.4621 0.0749 1.0000 Uiso R . . . . . H612 H 0.1902 0.9514 0.4417 0.0746 1.0000 Uiso R . . . . . H613 H 0.1382 0.5885 0.4116 0.0745 1.0000 Uiso R . . . . . H7 H 0.0362 0.6728 0.6222 0.0482 1.0000 Uiso R . . . . . H8 H 0.0891 0.4242 0.7686 0.0710 1.0000 Uiso R . . . . . H9 H 0.2501 0.2001 0.7902 0.0565 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 0.056(13) 0.0608(18) 0.0334(13) 0.0059(10) 0.0081(19) 0.012(3) N2 0.006(13) 0.0438(17) 0.0293(13) 0.0026(10) 0.0016(18) 0.011(2) C3 0.088(15) 0.0361(18) 0.0170(12) -0.0002(9) 0.0001(19) 0.002(3) C4 0.047(14) 0.0300(16) 0.0213(13) -0.0020(9) 0.0001(19) 0.001(2) C5 0.092(15) 0.0321(18) 0.0181(13) -0.0033(10) 0.007(2) 0.005(3) O5 0.030(11) 0.0570(17) 0.0235(10) 0.0049(8) 0.0075(15) 0.007(2) C6 0.038(14) 0.0332(17) 0.0253(14) -0.0045(10) 0.004(2) -0.001(3) C61 0.084(15) 0.0414(18) 0.0258(14) -0.0008(10) -0.003(2) 0.011(3) C7 0.040(15) 0.0464(19) 0.0321(15) -0.0054(11) 0.004(2) 0.005(3) C8 0.103(19) 0.048(2) 0.0255(15) -0.0015(12) 0.010(2) -0.005(4) C9 0.082(16) 0.038(2) 0.0232(14) -0.0011(11) 0.010(2) -0.005(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.8(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 O1 . N2 . 1.393(11) yes O1 . H1 . 0.86(5) no N2 . C3 . 1.266(9) yes C3 . C4 . 1.460(13) yes C3 . H3 . 0.933 no C4 . C5 . 1.415(6) yes C4 . C9 . 1.396(9) yes C5 . O5 . 1.383(7) yes C5 . C6 . 1.367(13) yes O5 . H5 . 0.87(5) no C6 . C61 . 1.513(6) yes C6 . C7 . 1.398(8) yes C61 . H611 . 0.952 no C61 . H612 . 0.958 no C61 . H613 . 0.949 no C7 . C8 . 1.398(7) yes C7 . H7 . 0.933 no C8 . C9 . 1.346(15) yes C8 . H8 . 0.924 no C9 . H9 . 0.939 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 . 116(6) no O1 . N2 . C3 . 112.8(4) yes N2 . C3 . C4 . 120.8(4) yes N2 . C3 . H3 . 119.2 no C4 . C3 . H3 . 120.0 no C3 . C4 . C5 . 122.7(6) yes C3 . C4 . C9 . 119.9(4) yes C5 . C4 . C9 . 117.4(7) yes C4 . C5 . O5 . 119.5(7) yes C4 . C5 . C6 . 122.2(6) yes O5 . C5 . C6 . 118.3(4) yes C5 . O5 . H5 . 105(4) no C5 . C6 . C61 . 120.1(6) yes C5 . C6 . C7 . 118.4(4) yes C61 . C6 . C7 . 121.6(8) yes C6 . C61 . H611 . 111.3 no C6 . C61 . H612 . 109.2 no H611 . C61 . H612 . 108.3 no C6 . C61 . H613 . 109.9 no H611 . C61 . H613 . 108.5 no H612 . C61 . H613 . 109.4 no C6 . C7 . C8 . 119.9(8) yes C6 . C7 . H7 . 119.3 no C8 . C7 . H7 . 120.8 no C7 . C8 . C9 . 121.0(7) yes C7 . C8 . H8 . 119.2 no C9 . C8 . H8 . 119.9 no C4 . C9 . C8 . 121.1(4) yes C4 . C9 . H9 . 119.5 no C8 . C9 . H9 . 119.4 no _chemical_name_common 3-Methylsalicylaldoxime #END data_Me22kbar _database_code_depnum_ccdc_archive 'CCDC 657064' _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 12.941(4) _cell_length_b 3.6146(5) _cell_length_c 13.7188(17) _cell_angle_alpha 90 _cell_angle_beta 91.47(2) _cell_angle_gamma 90 _cell_volume 641.5(2) _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 0.0000 0.0000 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 0.4899 20.6593 0.2620 7.7404 0.1968 49.5519 0.0499 2.2016 0.0013 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0030 0.0020 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' N 0.0010 0.0010 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' _cell_formula_units_Z 4 # Given Formula = C8 H9 N1 O2 # Dc = 1.57 Fooo = 320.00 Mu = 1.14 M = 151.16 # Found Formula = C8 H9 N1 O2 # Dc = 1.57 FOOO = 320.00 Mu = 1.14 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 755 _cell_measurement_theta_min 4 _cell_measurement_theta_max 19 _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 1.565 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.114 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Bruker-Nonius ApexII CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.45770 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 2200000 _diffrn_reflns_number 6282 _reflns_number_total 822 _diffrn_reflns_av_R_equivalents 0.157 # Number of reflections with Friedels Law is 909 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1957 _diffrn_reflns_theta_min 3.754 _diffrn_reflns_theta_max 19.078 _diffrn_measured_fraction_theta_max 0.421 _diffrn_reflns_theta_full 16.217 _diffrn_measured_fraction_theta_full 0.458 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _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 -6 _reflns_limit_h_max 6 _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 1.79 _oxford_diffrn_Wilson_scale 0.06 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.19 _refine_diff_density_max 0.32 _refine_ls_number_reflns 818 _refine_ls_number_restraints 2 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.1022 _refine_ls_wR_factor_ref 0.1964 _refine_ls_goodness_of_fit_ref 1.0253 #_reflns_number_all 818 _refine_ls_R_factor_all 0.1022 _refine_ls_wR_factor_all 0.1964 # 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 517 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_gt 0.1640 _refine_ls_shift/su_max 0.000146 # 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^) + ( 0.13P)^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: 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.46 020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.16 088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.72 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.72 This is probably due to the lack of information in one direction which occurs as a result of the Merrill-Bassett diamond-anvil cell shading a significant region of reciprocal space. The effect of this shading is often to cause a smearing out of electron density in one particular direction. 417_ALERT_2_C Short Inter D-H..H-D H1 .. H5 .. 2.12 Ang. 432_ALERT_2_C Short Inter X...Y Contact O1 .. C3 .. 2.98 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 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 #------------------------------------------------------------------------------- 13.23 0.500 0.476 675 321 354 14.58 0.550 0.449 881 396 485 15.94 0.600 0.453 1167 529 638 #----------------------------------------------------------- ACTA Min. Res. ---- 17.31 0.650 0.443 1477 654 823 18.69 0.700 0.422 1827 771 1056 19.08 0.714 0.421 1952 822 1130 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.5690(5) 0.0441(7) 0.63604(16) 0.0465 1.0000 Uani D . . . . . N2 N 0.4733(6) 0.2047(7) 0.60906(17) 0.0290 1.0000 Uani . . . . . . C3 C 0.4039(6) 0.1615(8) 0.67290(18) 0.0295 1.0000 Uani . . . . . . C4 C 0.3041(6) 0.3097(8) 0.65798(17) 0.0335 1.0000 Uani . . . . . . C5 C 0.2692(7) 0.4755(8) 0.56861(18) 0.0370 1.0000 Uani . . . . . . O5 O 0.3361(4) 0.5022(6) 0.49341(13) 0.0298 1.0000 Uani D . . . . . C6 C 0.1710(7) 0.6102(9) 0.55388(18) 0.0349 1.0000 Uani . . . . . . C61 C 0.1405(6) 0.7763(8) 0.45696(18) 0.0421 1.0000 Uani . . . . . . C7 C 0.1020(6) 0.5833(8) 0.6300(2) 0.0252 1.0000 Uani . . . . . . C8 C 0.1333(7) 0.4279(10) 0.7195(2) 0.0316 1.0000 Uani . . . . . . C9 C 0.2300(7) 0.2925(9) 0.73242(18) 0.0375 1.0000 Uani . . . . . . H1 H 0.610(8) 0.195(19) 0.610(5) 0.0700 1.0000 Uiso D . . . . . H3 H 0.4201 0.0263 0.7302 0.0354 1.0000 Uiso R . . . . . H5 H 0.399(4) 0.414(17) 0.505(4) 0.0452 1.0000 Uiso D . . . . . H611 H 0.0747 0.8969 0.4589 0.0626 1.0000 Uiso R . . . . . H612 H 0.1913 0.9556 0.4389 0.0621 1.0000 Uiso R . . . . . H613 H 0.1371 0.5816 0.4097 0.0617 1.0000 Uiso R . . . . . H7 H 0.0349 0.6705 0.6206 0.0298 1.0000 Uiso R . . . . . H8 H 0.0868 0.4132 0.7705 0.0382 1.0000 Uiso R . . . . . H9 H 0.2486 0.1837 0.7925 0.0441 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 0.065(11) 0.0477(15) 0.0271(11) 0.0064(8) 0.0036(16) 0.013(2) N2 0.032(11) 0.0337(14) 0.0211(11) 0.0017(8) 0.0006(17) 0.003(2) C3 0.042(12) 0.0306(15) 0.0158(11) -0.0003(9) 0.0038(17) 0.000(2) C4 0.059(12) 0.0274(14) 0.0143(11) -0.0017(8) 0.0001(18) 0.000(2) C5 0.074(13) 0.0235(14) 0.0140(11) 0.0001(8) 0.0067(18) -0.001(2) O5 0.023(10) 0.0503(15) 0.0167(9) 0.0032(7) 0.0081(14) 0.0062(18) C6 0.063(12) 0.0252(15) 0.0164(12) -0.0027(8) 0.0028(18) 0.001(2) C61 0.075(12) 0.0348(15) 0.0168(11) -0.0001(8) -0.0046(17) 0.009(2) C7 0.010(12) 0.0406(16) 0.0254(13) -0.0037(9) 0.0042(19) 0.002(2) C8 0.032(14) 0.0420(19) 0.0215(13) -0.0005(10) 0.008(2) 0.000(3) C9 0.067(13) 0.0302(16) 0.0152(12) 0.0001(9) 0.0038(18) -0.006(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.5(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 O1 . N2 . 1.408(10) yes O1 . H1 . 0.84(5) no N2 . C3 . 1.280(8) yes C3 . C4 . 1.409(11) yes C3 . H3 . 0.945 no C4 . C5 . 1.428(5) yes C4 . C9 . 1.419(8) yes C5 . O5 . 1.367(6) yes C5 . C6 . 1.371(11) yes O5 . H5 . 0.89(5) no C6 . C61 . 1.502(5) yes C6 . C7 . 1.395(7) yes C61 . H611 . 0.958 no C61 . H612 . 0.960 no C61 . H613 . 0.957 no C7 . C8 . 1.401(6) yes C7 . H7 . 0.930 no C8 . C9 . 1.352(12) yes C8 . H8 . 0.936 no C9 . H9 . 0.939 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(8) no O1 . N2 . C3 . 113.4(3) yes N2 . C3 . C4 . 120.7(3) yes N2 . C3 . H3 . 119.3 no C4 . C3 . H3 . 120.0 no C3 . C4 . C5 . 123.6(5) yes C3 . C4 . C9 . 120.8(4) yes C5 . C4 . C9 . 115.6(6) yes C4 . C5 . O5 . 119.0(6) yes C4 . C5 . C6 . 123.2(5) yes O5 . C5 . C6 . 117.8(3) yes C5 . O5 . H5 . 116(4) no C5 . C6 . C61 . 119.6(5) yes C5 . C6 . C7 . 118.3(4) yes C61 . C6 . C7 . 122.1(7) yes C6 . C61 . H611 . 111.7 no C6 . C61 . H612 . 109.4 no H611 . C61 . H612 . 108.4 no C6 . C61 . H613 . 108.2 no H611 . C61 . H613 . 109.2 no H612 . C61 . H613 . 110.0 no C6 . C7 . C8 . 120.5(7) yes C6 . C7 . H7 . 119.1 no C8 . C7 . H7 . 120.4 no C7 . C8 . C9 . 120.4(6) yes C7 . C8 . H8 . 120.1 no C9 . C8 . H8 . 119.5 no C4 . C9 . C8 . 122.0(4) yes C4 . C9 . H9 . 119.2 no C8 . C9 . H9 . 118.8 no _chemical_name_common 3-Methylsalicylaldoxime #END data_Me35kbar _database_code_depnum_ccdc_archive 'CCDC 657065' _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 12.878(4) _cell_length_b 3.5363(5) _cell_length_c 13.5218(16) _cell_angle_alpha 90 _cell_angle_beta 91.88(2) _cell_angle_gamma 90 _cell_volume 615.5(2) _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 0.0000 0.0000 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 0.0010 0.0010 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 0.0030 0.0020 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 = 1.63 Fooo = 320.00 Mu = 1.18 M = 151.16 # Found Formula = C8 H9 N1 O2 # Dc = 1.63 FOOO = 320.00 Mu = 1.18 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 763 _cell_measurement_theta_min 2 _cell_measurement_theta_max 24 _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 1.631 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.118 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Bruker-Nonius ApexII CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.45770 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 3500000 _diffrn_reflns_number 8856 _reflns_number_total 1402 _diffrn_reflns_av_R_equivalents 0.199 # Number of reflections with Friedels Law is 1517 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3905 _diffrn_reflns_theta_min 2.162 _diffrn_reflns_theta_max 24.659 _diffrn_measured_fraction_theta_max 0.357 _diffrn_reflns_theta_full 18.494 _diffrn_measured_fraction_theta_full 0.421 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 1.61 _oxford_diffrn_Wilson_scale 0.07 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.20 _refine_ls_number_reflns 1395 _refine_ls_number_restraints 2 _refine_ls_number_parameters 107 #_refine_ls_R_factor_ref 0.1299 _refine_ls_wR_factor_ref 0.1948 _refine_ls_goodness_of_fit_ref 1.0041 #_reflns_number_all 1395 _refine_ls_R_factor_all 0.1299 _refine_ls_wR_factor_all 0.1948 # 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 654 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_gt 0.1423 _refine_ls_shift/su_max 0.000205 # 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^ + 0.14P] 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: 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.42 020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.20 026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 417_ALERT_2_B Short Inter D-H..H-D H1 .. H5 .. 2.09 Ang. 432_ALERT_2_C Short Inter X...Y Contact O1 .. C3 .. 2.92 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 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 #------------------------------------------------------------------------------- 13.23 0.500 0.481 651 313 338 14.58 0.550 0.460 853 392 461 15.94 0.600 0.455 1124 511 613 #----------------------------------------------------------- ACTA Min. Res. ---- 17.31 0.650 0.444 1428 634 794 18.69 0.700 0.420 1760 740 1020 20.08 0.750 0.415 2177 903 1274 21.48 0.800 0.396 2650 1049 1601 22.90 0.850 0.372 3145 1170 1975 24.33 0.900 0.364 3767 1370 2397 24.66 0.912 0.357 3925 1402 2523 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.5701(4) 0.0334(6) 0.63649(13) 0.0389 1.0000 Uani D . . . . . N2 N 0.4749(5) 0.1984(6) 0.60907(14) 0.0300 1.0000 Uani . . . . . . C3 C 0.4062(5) 0.1481(7) 0.67347(15) 0.0257 1.0000 Uani . . . . . . C4 C 0.3033(5) 0.3018(6) 0.65865(14) 0.0252 1.0000 Uani . . . . . . C5 C 0.2693(5) 0.4734(7) 0.56803(14) 0.0222 1.0000 Uani . . . . . . O5 O 0.3374(4) 0.5039(5) 0.49213(11) 0.0338 1.0000 Uani D . . . . . C6 C 0.1690(5) 0.6079(7) 0.55316(15) 0.0266 1.0000 Uani . . . . . . C61 C 0.1387(5) 0.7805(7) 0.45475(15) 0.0304 1.0000 Uani . . . . . . C7 C 0.0993(5) 0.5768(7) 0.62928(16) 0.0275 1.0000 Uani . . . . . . C8 C 0.1312(6) 0.4152(8) 0.71995(16) 0.0288 1.0000 Uani . . . . . . C9 C 0.2295(6) 0.2795(8) 0.73367(15) 0.0324 1.0000 Uani . . . . . . H1 H 0.609(6) 0.169(12) 0.594(3) 0.0596 1.0000 Uiso D . . . . . H3 H 0.4230 0.0107 0.7300 0.0318 1.0000 Uiso R . . . . . H5 H 0.398(4) 0.387(12) 0.508(3) 0.0510 1.0000 Uiso D . . . . . H611 H 0.0718 0.8990 0.4580 0.0461 1.0000 Uiso R . . . . . H612 H 0.1885 0.9725 0.4360 0.0450 1.0000 Uiso R . . . . . H613 H 0.1357 0.5904 0.4054 0.0453 1.0000 Uiso R . . . . . H7 H 0.0311 0.6680 0.6198 0.0337 1.0000 Uiso R . . . . . H8 H 0.0838 0.3988 0.7708 0.0365 1.0000 Uiso R . . . . . H9 H 0.2485 0.1661 0.7956 0.0388 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 0.052(8) 0.0371(10) 0.0275(8) 0.0050(7) 0.0021(13) 0.0075(16) N2 0.037(10) 0.0310(10) 0.0225(8) 0.0021(7) 0.0016(14) 0.0028(17) C3 0.034(10) 0.0242(10) 0.0194(8) 0.0001(6) 0.0047(14) 0.0014(17) C4 0.035(9) 0.0226(10) 0.0178(8) -0.0020(6) -0.0003(13) -0.0007(17) C5 0.025(10) 0.0246(11) 0.0174(8) -0.0007(6) 0.0015(13) -0.0011(18) O5 0.043(8) 0.0389(11) 0.0195(7) 0.0046(6) 0.0053(11) 0.0057(16) C6 0.038(9) 0.0229(10) 0.0192(8) -0.0018(7) 0.0005(13) 0.0024(18) C61 0.042(9) 0.0285(10) 0.0205(8) -0.0011(7) 0.0018(14) 0.0058(17) C7 0.026(10) 0.0314(12) 0.0253(9) -0.0018(8) 0.0012(15) 0.0032(18) C8 0.030(11) 0.0351(13) 0.0214(9) -0.0014(8) 0.0061(15) -0.002(2) C9 0.053(11) 0.0279(12) 0.0166(8) -0.0001(7) 0.0011(14) -0.0015(19) _refine_ls_extinction_coef 470(110) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _oxford_refine_ls_scale 4.0(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 O1 . N2 . 1.396(8) yes O1 . H1 . 0.91(4) no N2 . C3 . 1.275(6) yes C3 . C4 . 1.440(9) yes C3 . H3 . 0.926 no C4 . C5 . 1.423(4) yes C4 . C9 . 1.414(6) yes C5 . O5 . 1.377(5) yes C5 . C6 . 1.384(9) yes O5 . H5 . 0.90(5) no C6 . C61 . 1.504(4) yes C6 . C7 . 1.393(6) yes C61 . H611 . 0.959 no C61 . H612 . 0.974 no C61 . H613 . 0.947 no C7 . C8 . 1.402(5) yes C7 . H7 . 0.940 no C8 . C9 . 1.361(10) yes C8 . H8 . 0.935 no C9 . H9 . 0.953 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 . 96(5) no O1 . N2 . C3 . 112.6(3) yes N2 . C3 . C4 . 120.6(3) yes N2 . C3 . H3 . 119.2 no C4 . C3 . H3 . 120.1 no C3 . C4 . C5 . 122.4(4) yes C3 . C4 . C9 . 121.0(3) yes C5 . C4 . C9 . 116.5(5) yes C4 . C5 . O5 . 119.3(5) yes C4 . C5 . C6 . 122.0(4) yes O5 . C5 . C6 . 118.6(3) yes C5 . O5 . H5 . 111(3) no C5 . C6 . C61 . 118.8(4) yes C5 . C6 . C7 . 119.1(3) yes C61 . C6 . C7 . 122.0(5) yes C6 . C61 . H611 . 110.2 no C6 . C61 . H612 . 111.1 no H611 . C61 . H612 . 107.9 no C6 . C61 . H613 . 109.8 no H611 . C61 . H613 . 109.1 no H612 . C61 . H613 . 108.8 no C6 . C7 . C8 . 120.0(6) yes C6 . C7 . H7 . 119.7 no C8 . C7 . H7 . 120.3 no C7 . C8 . C9 . 120.5(5) yes C7 . C8 . H8 . 119.2 no C9 . C8 . H8 . 120.3 no C4 . C9 . C8 . 121.8(3) yes C4 . C9 . H9 . 119.7 no C8 . C9 . H9 . 118.6 no _chemical_name_common 3-Methylsalicylaldoxime #END data_Me42kbar _database_code_depnum_ccdc_archive 'CCDC 657066' _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 12.831(3) _cell_length_b 3.5096(4) _cell_length_c 13.4462(13) _cell_angle_alpha 90 _cell_angle_beta 92.10(2) _cell_angle_gamma 90 _cell_volume 605.11(16) _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 0.0000 0.0000 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 0.0010 0.0010 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 0.0030 0.0020 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 = 1.66 Fooo = 320.00 Mu = 1.20 M = 151.16 # Found Formula = C8 H9 N1 O2 # Dc = 1.66 FOOO = 320.00 Mu = 1.20 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 665 _cell_measurement_theta_min 4 _cell_measurement_theta_max 24 _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 1.659 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.120 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Bruker-Nonius ApexII CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.45770 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 4200000 _diffrn_reflns_number 8863 _reflns_number_total 1415 _diffrn_reflns_av_R_equivalents 0.271 # Number of reflections with Friedels Law is 1530 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3843 _diffrn_reflns_theta_min 3.864 _diffrn_reflns_theta_max 24.667 _diffrn_measured_fraction_theta_max 0.367 _diffrn_reflns_theta_full 18.500 _diffrn_measured_fraction_theta_full 0.428 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _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 -0.32 _refine_diff_density_max 0.23 _refine_ls_number_reflns 1404 _refine_ls_number_restraints 2 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.1608 _refine_ls_wR_factor_ref 0.2400 _refine_ls_goodness_of_fit_ref 0.9604 #_reflns_number_all 1404 _refine_ls_R_factor_all 0.1608 _refine_ls_wR_factor_all 0.2400 # 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 618 _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_gt 0.1729 _refine_ls_shift/su_max 0.000164 # 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^) + ( 0.13P)^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: 020_ALERT_3_A The value of Rint is greater than 0.10 ......... 0.27 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.43 026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 432_ALERT_2_B Short Inter X...Y Contact O1 .. C3 .. 2.89 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.16 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 213_ALERT_2_C Atom C9 has ADP max/min Ratio ............. 3.70 oblate 213_ALERT_2_C Atom C61 has ADP max/min Ratio ............. 4.00 oblate This is probably due to the lack of information in one direction which occurs as a result of the Merrill-Bassett diamond-anvil cell shading a significant region of reciprocal space. The effect of this shading is often to cause a smearing out of electron density in one particular direction. 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 #------------------------------------------------------------------------------- 13.23 0.500 0.488 639 312 327 14.58 0.550 0.473 842 398 444 15.94 0.600 0.463 1091 505 586 #----------------------------------------------------------- ACTA Min. Res. ---- 17.31 0.650 0.455 1399 636 763 18.69 0.700 0.429 1733 743 990 20.08 0.750 0.420 2140 899 1241 21.48 0.800 0.405 2610 1056 1554 22.90 0.850 0.382 3094 1181 1913 24.33 0.900 0.371 3702 1374 2328 24.67 0.912 0.367 3857 1415 2442 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.5711(5) 0.0299(7) 0.63667(15) 0.0388 1.0000 Uani D . . . . . N2 N 0.4756(5) 0.1949(7) 0.60953(15) 0.0220 1.0000 Uani . . . . . . C3 C 0.4057(6) 0.1434(8) 0.67370(17) 0.0280 1.0000 Uani . . . . . . C4 C 0.3022(6) 0.2989(7) 0.65825(16) 0.0189 1.0000 Uani . . . . . . C5 C 0.2695(6) 0.4736(8) 0.56811(15) 0.0142 1.0000 Uani . . . . . . O5 O 0.3370(5) 0.5048(6) 0.49202(13) 0.0323 1.0000 Uani D . . . . . C6 C 0.1687(6) 0.6086(8) 0.55265(16) 0.0179 1.0000 Uani . . . . . . C61 C 0.1377(5) 0.7831(7) 0.45384(16) 0.0170 1.0000 Uani . . . . . . C7 C 0.0983(6) 0.5749(7) 0.62881(17) 0.0221 1.0000 Uani . . . . . . C8 C 0.1306(7) 0.4094(9) 0.72019(18) 0.0254 1.0000 Uani . . . . . . C9 C 0.2301(6) 0.2758(9) 0.73392(17) 0.0168 1.0000 Uani . . . . . . H1 H 0.617(6) 0.136(14) 0.599(4) 0.0582 1.0000 Uiso D . . . . . H3 H 0.4223 0.0003 0.7304 0.0345 1.0000 Uiso R . . . . . H5 H 0.397(4) 0.389(14) 0.502(4) 0.0480 1.0000 Uiso D . . . . . H611 H 0.0689 0.8896 0.4547 0.0262 1.0000 Uiso R . . . . . H612 H 0.1861 0.9832 0.4377 0.0265 1.0000 Uiso R . . . . . H613 H 0.1388 0.5899 0.4031 0.0267 1.0000 Uiso R . . . . . H7 H 0.0305 0.6665 0.6203 0.0270 1.0000 Uiso R . . . . . H8 H 0.0838 0.3850 0.7714 0.0314 1.0000 Uiso R . . . . . H9 H 0.2504 0.1648 0.7969 0.0196 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 0.055(10) 0.0366(12) 0.0251(9) 0.0054(7) 0.0046(15) 0.0116(18) N2 0.015(10) 0.0320(12) 0.0190(8) 0.0015(7) 0.0036(14) 0.0051(18) C3 0.042(11) 0.0260(12) 0.0161(8) -0.0004(7) 0.0051(15) -0.002(2) C4 0.017(10) 0.0234(11) 0.0160(8) -0.0007(7) 0.0026(14) 0.0001(18) C5 0.003(10) 0.0252(12) 0.0146(7) -0.0009(7) 0.0014(13) 0.0006(18) O5 0.042(9) 0.0385(13) 0.0164(7) 0.0022(6) 0.0080(12) 0.0051(17) C6 0.013(10) 0.0251(12) 0.0155(8) -0.0011(7) -0.0010(13) 0.0005(19) C61 0.004(10) 0.0297(12) 0.0168(8) -0.0002(7) -0.0009(13) 0.0074(17) C7 0.016(11) 0.0288(13) 0.0216(9) -0.0010(8) 0.0031(16) 0.0052(18) C8 0.023(12) 0.0360(15) 0.0175(9) -0.0006(8) 0.0068(16) -0.002(3) C9 0.003(12) 0.0305(14) 0.0173(9) -0.0013(8) 0.0033(15) -0.002(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.8(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 O1 . N2 . 1.391(8) yes O1 . H1 . 0.87(4) no N2 . C3 . 1.280(7) yes C3 . C4 . 1.444(11) yes C3 . H3 . 0.932 no C4 . C5 . 1.408(4) yes C4 . C9 . 1.402(7) yes C5 . O5 . 1.369(6) yes C5 . C6 . 1.386(10) yes O5 . H5 . 0.88(5) no C6 . C61 . 1.503(4) yes C6 . C7 . 1.395(6) yes C61 . H611 . 0.959 no C61 . H612 . 0.967 no C61 . H613 . 0.962 no C7 . C8 . 1.408(5) yes C7 . H7 . 0.931 no C8 . C9 . 1.366(11) yes C8 . H8 . 0.933 no C9 . H9 . 0.959 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 . 106(5) no O1 . N2 . C3 . 113.4(3) yes N2 . C3 . C4 . 120.9(3) yes N2 . C3 . H3 . 118.9 no C4 . C3 . H3 . 120.2 no C3 . C4 . C5 . 122.1(5) yes C3 . C4 . C9 . 120.1(3) yes C5 . C4 . C9 . 117.8(6) yes C4 . C5 . O5 . 120.1(6) yes C4 . C5 . C6 . 121.6(5) yes O5 . C5 . C6 . 118.3(3) yes C5 . O5 . H5 . 115(3) no C5 . C6 . C61 . 119.1(4) yes C5 . C6 . C7 . 119.1(3) yes C61 . C6 . C7 . 121.8(6) yes C6 . C61 . H611 . 111.2 no C6 . C61 . H612 . 110.1 no H611 . C61 . H612 . 108.5 no C6 . C61 . H613 . 109.2 no H611 . C61 . H613 . 108.7 no H612 . C61 . H613 . 109.0 no C6 . C7 . C8 . 119.9(6) yes C6 . C7 . H7 . 120.5 no C8 . C7 . H7 . 119.6 no C7 . C8 . C9 . 120.2(5) yes C7 . C8 . H8 . 120.3 no C9 . C8 . H8 . 119.5 no C4 . C9 . C8 . 121.3(3) yes C4 . C9 . H9 . 120.0 no C8 . C9 . H9 . 118.7 no _chemical_name_common 3-Methylsalicylaldoxime #END data_Me49kbar _database_code_depnum_ccdc_archive 'CCDC 657067' _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 12.766(7) _cell_length_b 3.4872(9) _cell_length_c 13.382(3) _cell_angle_alpha 90 _cell_angle_beta 92.27(4) _cell_angle_gamma 90 _cell_volume 595.2(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 0.0000 0.0000 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 0.0010 0.0010 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 0.0030 0.0020 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 = 1.69 Fooo = 320.00 Mu = 1.22 M = 151.16 # Found Formula = C8 H9 N1 O2 # Dc = 1.69 FOOO = 320.00 Mu = 1.22 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 845 _cell_measurement_theta_min 4 _cell_measurement_theta_max 24 _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 1.687 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.122 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_absorpt_correction_T_min 0.35 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Bruker-Nonius ApexII CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.45770 _diffrn_measurement_method \w _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'Model taken from ambient pressure structure' _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_ambient_pressure 4900000 _diffrn_reflns_number 8106 _reflns_number_total 1373 _diffrn_reflns_av_R_equivalents 0.222 # Number of reflections with Friedels Law is 1489 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3781 _diffrn_reflns_theta_min 3.889 _diffrn_reflns_theta_max 24.669 _diffrn_measured_fraction_theta_max 0.362 _diffrn_reflns_theta_full 18.502 _diffrn_measured_fraction_theta_full 0.435 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _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 -0.38 _refine_diff_density_max 0.44 _refine_ls_number_reflns 1371 _refine_ls_number_restraints 2 _refine_ls_number_parameters 107 #_refine_ls_R_factor_ref 0.1606 _refine_ls_wR_factor_ref 0.3178 _refine_ls_goodness_of_fit_ref 0.9284 #_reflns_number_all 1371 _refine_ls_R_factor_all 0.1606 _refine_ls_wR_factor_all 0.3178 # 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 673 _refine_ls_R_factor_gt 0.0987 _refine_ls_wR_factor_gt 0.2423 _refine_ls_shift/su_max 0.000147 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.20P)^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: 020_ALERT_3_A The value of Rint is greater than 0.10 ......... 0.22 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.44 026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 432_ALERT_2_B Short Inter X...Y Contact O1 .. C3 .. 2.87 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.15 Ang. 432_ALERT_2_C Short Inter X...Y Contact C6 .. C61 .. 3.18 Ang. 432_ALERT_2_C Short Inter X...Y Contact C7 .. C8 .. 3.18 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 084_ALERT_2_C High R2 Value .................................. 0.32 The high R2 value is due to the low quality and completeness of the dataset as a result of the high pressure conditions applied to the crystal. 150_ALERT_1_C Volume as Calculated Differs from that Given ... 595.20 Ang-3 This is probably due to a simple rounding error. 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.46 This is probably due to the lack of information in one direction which occurs as a result of the Merrill-Bassett diamond-anvil cell shading a significant region of reciprocal space. The effect of this shading is often to cause a smearing out of electron density in one particular direction. 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 #------------------------------------------------------------------------------- 13.23 0.500 0.484 626 303 323 14.58 0.550 0.472 825 389 436 15.94 0.600 0.464 1076 499 577 #----------------------------------------------------------- ACTA Min. Res. ---- 17.31 0.650 0.459 1370 629 741 18.69 0.700 0.435 1709 744 965 20.08 0.750 0.422 2102 888 1214 21.48 0.800 0.408 2564 1047 1517 22.90 0.850 0.385 3053 1174 1879 24.33 0.900 0.368 3633 1336 2297 24.67 0.912 0.362 3794 1373 2421 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.5711(6) 0.0251(7) 0.63670(17) 0.0384 1.0000 Uani D . . . . . N2 N 0.4762(6) 0.1934(7) 0.60918(17) 0.0337 1.0000 Uani . . . . . . C3 C 0.4059(7) 0.1409(8) 0.67428(19) 0.0326 1.0000 Uani . . . . . . C4 C 0.3052(6) 0.2965(7) 0.65893(18) 0.0304 1.0000 Uani . . . . . . C5 C 0.2676(7) 0.4718(7) 0.56807(18) 0.0284 1.0000 Uani . . . . . . O5 O 0.3368(5) 0.5061(6) 0.49144(15) 0.0332 1.0000 Uani D . . . . . C6 C 0.1699(7) 0.6080(7) 0.55218(18) 0.0268 1.0000 Uani . . . . . . C61 C 0.1385(6) 0.7853(8) 0.45315(18) 0.0274 1.0000 Uani . . . . . . C7 C 0.0979(7) 0.5726(8) 0.6285(2) 0.0301 1.0000 Uani . . . . . . C8 C 0.1305(7) 0.4058(9) 0.7203(2) 0.0349 1.0000 Uani . . . . . . C9 C 0.2297(7) 0.2699(8) 0.73442(19) 0.0303 1.0000 Uani . . . . . . H3 H 0.4233 -0.0021 0.7343 0.0337 1.0000 Uiso R . . . . . H611 H 0.0685 0.8898 0.4554 0.0355 1.0000 Uiso R . . . . . H612 H 0.1857 0.9884 0.4390 0.0362 1.0000 Uiso R . . . . . H613 H 0.1408 0.5885 0.4018 0.0357 1.0000 Uiso R . . . . . H7 H 0.0287 0.6625 0.6183 0.0346 1.0000 Uiso R . . . . . H8 H 0.0842 0.3874 0.7719 0.0401 1.0000 Uiso R . . . . . H9 H 0.2505 0.1573 0.7970 0.0342 1.0000 Uiso R . . . . . H5 H 0.397(4) 0.410(14) 0.510(4) 0.0392 1.0000 Uiso D . . . . . H1 H 0.619(5) 0.115(12) 0.597(3) 0.0326 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 0.051(11) 0.0358(12) 0.0288(10) 0.0054(8) 0.0046(19) 0.0072(18) N2 0.052(11) 0.0276(10) 0.0223(9) -0.0002(7) 0.0071(18) 0.0059(19) C3 0.056(12) 0.0235(11) 0.0191(9) -0.0001(7) 0.0058(18) -0.001(2) C4 0.052(11) 0.0218(10) 0.0180(9) -0.0005(7) 0.0043(17) 0.0003(19) C5 0.046(11) 0.0208(10) 0.0181(9) -0.0016(7) 0.0034(17) -0.0001(19) O5 0.044(11) 0.0353(12) 0.0214(9) 0.0045(7) 0.0114(16) 0.0064(17) C6 0.041(11) 0.0206(10) 0.0193(9) 0.0004(7) 0.0070(17) -0.0006(19) C61 0.035(11) 0.0257(11) 0.0215(10) 0.0000(8) 0.0048(17) 0.0043(19) C7 0.038(13) 0.0282(12) 0.0246(11) -0.0031(8) 0.014(2) -0.001(2) C8 0.055(13) 0.0306(13) 0.0197(10) -0.0012(9) 0.0121(19) -0.007(2) C9 0.046(12) 0.0258(11) 0.0189(10) 0.0009(8) 0.0047(18) 0.007(2) _refine_ls_extinction_coef 3387.332 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 6.7(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 O1 . N2 . 1.383(10) yes O1 . H1 . 0.88(4) no N2 . C3 . 1.289(8) yes C3 . C4 . 1.402(12) yes C3 . H3 . 0.964 no C4 . C5 . 1.427(6) yes C4 . C9 . 1.427(8) yes C5 . O5 . 1.385(7) yes C5 . C6 . 1.343(12) yes O5 . H5 . 0.87(5) no C6 . C61 . 1.503(5) yes C6 . C7 . 1.407(7) yes C61 . H611 . 0.967 no C61 . H612 . 0.954 no C61 . H613 . 0.973 no C7 . C8 . 1.407(6) yes C7 . H7 . 0.942 no C8 . C9 . 1.359(12) yes C8 . H8 . 0.927 no C9 . H9 . 0.953 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 . 108(4) no O1 . N2 . C3 . 112.7(3) yes N2 . C3 . C4 . 120.3(3) yes N2 . C3 . H3 . 119.5 no C4 . C3 . H3 . 120.1 no C3 . C4 . C5 . 124.5(5) yes C3 . C4 . C9 . 120.8(4) yes C5 . C4 . C9 . 114.6(7) yes C4 . C5 . O5 . 117.7(7) yes C4 . C5 . C6 . 124.5(6) yes O5 . C5 . C6 . 117.9(3) yes C5 . O5 . H5 . 110(3) no C5 . C6 . C61 . 120.0(5) yes C5 . C6 . C7 . 118.9(4) yes C61 . C6 . C7 . 121.1(6) yes C6 . C61 . H611 . 110.1 no C6 . C61 . H612 . 109.4 no H611 . C61 . H612 . 108.6 no C6 . C61 . H613 . 108.6 no H611 . C61 . H613 . 110.0 no H612 . C61 . H613 . 110.3 no C6 . C7 . C8 . 119.4(7) yes C6 . C7 . H7 . 120.1 no C8 . C7 . H7 . 120.5 no C7 . C8 . C9 . 120.5(6) yes C7 . C8 . H8 . 120.2 no C9 . C8 . H8 . 119.3 no C4 . C9 . C8 . 122.1(4) yes C4 . C9 . H9 . 118.5 no C8 . C9 . H9 . 119.4 no _chemical_name_common 3-Methylsalicylaldoxime #END data_Me56kbar _database_code_depnum_ccdc_archive 'CCDC 657068' _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 12.750(4) _cell_length_b 3.4482(6) _cell_length_c 13.2910(18) _cell_angle_alpha 90 _cell_angle_beta 92.45(2) _cell_angle_gamma 90 _cell_volume 583.8(2) _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 0.0000 0.0000 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 0.0010 0.0010 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 0.0030 0.0020 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 = 1.72 Fooo = 320.00 Mu = 1.25 M = 151.16 # Found Formula = C8 H9 N1 O2 # Dc = 1.72 FOOO = 320.00 Mu = 1.25 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 783 _cell_measurement_theta_min 2 _cell_measurement_theta_max 24 _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 1.720 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.125 # Sheldrick geometric approximatio 0.98 0.98 _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 0.98 _diffrn_measurement_device_type 'Bruker-Nonius ApexII CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.45770 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 5600000 _diffrn_reflns_number 7902 _reflns_number_total 1281 _diffrn_reflns_av_R_equivalents 0.242 # Number of reflections with Friedels Law is 1396 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3693 _diffrn_reflns_theta_min 2.188 _diffrn_reflns_theta_max 24.631 _diffrn_measured_fraction_theta_max 0.347 _diffrn_reflns_theta_full 18.473 _diffrn_measured_fraction_theta_full 0.420 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _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 -0.22 _refine_diff_density_max 0.18 _refine_ls_number_reflns 1267 _refine_ls_number_restraints 2 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.1285 _refine_ls_wR_factor_ref 0.1739 _refine_ls_goodness_of_fit_ref 1.0230 #_reflns_number_all 1267 _refine_ls_R_factor_all 0.1285 _refine_ls_wR_factor_all 0.1739 # 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 623 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_gt 0.1374 _refine_ls_shift/su_max 0.000193 # 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^) + ( 0.08P)^2^ + 0.07P] 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: 020_ALERT_3_A The value of Rint is greater than 0.10 ......... 0.24 026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.42 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 417_ALERT_2_B Short Inter D-H..H-D H1 .. H5 .. 2.09 Ang. 432_ALERT_2_B Short Inter X...Y Contact O1 .. C3 .. 2.84 Ang. 413_ALERT_2_C Short Inter XH3 .. XHn H7 .. H611 .. 2.12 Ang. 432_ALERT_2_C Short Inter X...Y Contact C3 .. C5 .. 3.17 Ang. 432_ALERT_2_C Short Inter X...Y Contact C3 .. C4 .. 3.18 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.10 Ang. 432_ALERT_2_C Short Inter X...Y Contact C6 .. C61 .. 3.14 Ang. 432_ALERT_2_C Short Inter X...Y Contact C7 .. C8 .. 3.13 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 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 #------------------------------------------------------------------------------- 13.23 0.500 0.476 614 292 322 14.58 0.550 0.454 813 369 444 15.94 0.600 0.439 1038 456 582 #----------------------------------------------------------- ACTA Min. Res. ---- 17.31 0.650 0.440 1347 593 754 18.69 0.700 0.423 1666 704 962 20.08 0.750 0.409 2055 841 1214 21.48 0.800 0.394 2505 986 1519 22.90 0.850 0.369 3005 1108 1897 24.33 0.900 0.350 3558 1247 2311 24.63 0.911 0.347 3689 1281 2408 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.5720(4) 0.0205(6) 0.63691(12) 0.0227 1.0000 Uani D . . . . . N2 N 0.4770(5) 0.1902(6) 0.60896(13) 0.0210 1.0000 Uani . . . . . . C3 C 0.4061(5) 0.1338(6) 0.67442(15) 0.0229 1.0000 Uani . . . . . . C4 C 0.3041(5) 0.2915(6) 0.65913(14) 0.0188 1.0000 Uani . . . . . . C5 C 0.2694(5) 0.4712(6) 0.56814(14) 0.0196 1.0000 Uani . . . . . . O5 O 0.3368(4) 0.5087(5) 0.49140(11) 0.0224 1.0000 Uani D . . . . . C6 C 0.1689(5) 0.6071(7) 0.55153(15) 0.0251 1.0000 Uani . . . . . . C61 C 0.1376(5) 0.7884(6) 0.45204(14) 0.0308 1.0000 Uani . . . . . . C7 C 0.0977(5) 0.5704(7) 0.62822(15) 0.0287 1.0000 Uani . . . . . . C8 C 0.1297(6) 0.4004(8) 0.72047(16) 0.0216 1.0000 Uani . . . . . . C9 C 0.2299(5) 0.2653(7) 0.73493(15) 0.0165 1.0000 Uani . . . . . . H1 H 0.621(5) 0.148(11) 0.597(3) 0.0363 1.0000 Uiso D . . . . . H3 H 0.4224 -0.0092 0.7332 0.0275 1.0000 Uiso R . . . . . H5 H 0.395(4) 0.398(11) 0.507(3) 0.0313 1.0000 Uiso D . . . . . H611 H 0.0736 0.9353 0.4567 0.0444 1.0000 Uiso R . . . . . H612 H 0.1921 0.9698 0.4337 0.0436 1.0000 Uiso R . . . . . H613 H 0.1290 0.5958 0.4003 0.0434 1.0000 Uiso R . . . . . H7 H 0.0284 0.6629 0.6185 0.0368 1.0000 Uiso R . . . . . H8 H 0.0820 0.3817 0.7705 0.0248 1.0000 Uiso R . . . . . H9 H 0.2510 0.1507 0.7981 0.0196 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 0.013(8) 0.0307(9) 0.0242(7) 0.0054(6) 0.0018(12) 0.0088(14) N2 0.021(8) 0.0247(9) 0.0173(7) 0.0007(6) 0.0006(12) 0.0035(15) C3 0.035(9) 0.0178(9) 0.0161(7) -0.0001(6) -0.0002(13) -0.0027(16) C4 0.024(9) 0.0172(9) 0.0154(7) -0.0004(6) -0.0003(13) -0.0006(15) C5 0.027(9) 0.0172(10) 0.0142(7) 0.0003(6) -0.0006(13) 0.0008(16) O5 0.019(8) 0.0308(10) 0.0175(6) 0.0039(6) 0.0060(11) 0.0050(13) C6 0.043(9) 0.0165(9) 0.0153(7) -0.0021(7) 0.0015(13) -0.0004(16) C61 0.058(9) 0.0192(9) 0.0148(7) 0.0002(6) -0.0003(13) 0.0008(15) C7 0.045(10) 0.0233(10) 0.0174(8) -0.0023(7) 0.0024(14) 0.0036(16) C8 0.022(10) 0.0262(12) 0.0173(8) -0.0015(8) 0.0055(14) -0.004(2) C9 0.011(10) 0.0232(11) 0.0153(8) 0.0010(7) 0.0020(13) -0.0001(17) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.15(18) 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 . 1.381(7) yes O1 . H1 . 0.95(4) no N2 . C3 . 1.296(6) yes C3 . C4 . 1.416(9) yes C3 . H3 . 0.940 no C4 . C5 . 1.413(4) yes C4 . C9 . 1.414(6) yes C5 . O5 . 1.368(5) yes C5 . C6 . 1.373(9) yes O5 . H5 . 0.86(4) no C6 . C61 . 1.501(4) yes C6 . C7 . 1.400(6) yes C61 . H611 . 0.964 no C61 . H612 . 0.974 no C61 . H613 . 0.959 no C7 . C8 . 1.404(4) yes C7 . H7 . 0.943 no C8 . C9 . 1.366(10) yes C8 . H8 . 0.921 no C9 . H9 . 0.956 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 . 104(4) no O1 . N2 . C3 . 112.6(3) yes N2 . C3 . C4 . 120.6(3) yes N2 . C3 . H3 . 120.1 no C4 . C3 . H3 . 119.3 no C3 . C4 . C5 . 122.9(4) yes C3 . C4 . C9 . 120.8(3) yes C5 . C4 . C9 . 116.3(5) yes C4 . C5 . O5 . 119.7(5) yes C4 . C5 . C6 . 122.9(4) yes O5 . C5 . C6 . 117.4(3) yes C5 . O5 . H5 . 111(3) no C5 . C6 . C61 . 119.7(4) yes C5 . C6 . C7 . 118.8(3) yes C61 . C6 . C7 . 121.5(5) yes C6 . C61 . H611 . 110.9 no C6 . C61 . H612 . 108.8 no H611 . C61 . H612 . 107.0 no C6 . C61 . H613 . 111.2 no H611 . C61 . H613 . 109.8 no H612 . C61 . H613 . 109.0 no C6 . C7 . C8 . 120.0(5) yes C6 . C7 . H7 . 120.2 no C8 . C7 . H7 . 119.7 no C7 . C8 . C9 . 120.0(5) yes C7 . C8 . H8 . 118.9 no C9 . C8 . H8 . 121.0 no C4 . C9 . C8 . 121.9(3) yes C4 . C9 . H9 . 118.7 no C8 . C9 . H9 . 119.4 no _chemical_name_common 3-Methylsalicylaldoxime #END data_tBu02kbar _database_code_depnum_ccdc_archive 'CCDC 657069' _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 6.5597(7) _cell_length_b 12.8532(9) _cell_length_c 13.479(2) _cell_angle_alpha 69.311(10) _cell_angle_beta 76.054(10) _cell_angle_gamma 79.035(6) _cell_volume 1024.9(2) _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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = 1.25 Fooo = 416.00 Mu = 0.86 M = 386.49 # Found Formula = C11 H15 N1 O2 # Dc = 1.25 FOOO = 416.00 Mu = 0.86 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 1987 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.086 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.28 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48690 _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 'Model taken from ambient structure' _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_ambient_pressure 200000 _diffrn_reflns_number 8650 _reflns_number_total 1697 _diffrn_reflns_av_R_equivalents 0.097 # Number of reflections with Friedels Law is 1697 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4213 _diffrn_reflns_theta_min 1.168 _diffrn_reflns_theta_max 17.747 _diffrn_measured_fraction_theta_max 0.403 _diffrn_reflns_theta_full 13.310 _diffrn_measured_fraction_theta_full 0.465 _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 -9 _diffrn_reflns_limit_l_max 9 _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 9 _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 -0.13 _refine_diff_density_max 0.12 _refine_ls_number_reflns 1688 _refine_ls_number_restraints 76 _refine_ls_number_parameters 265 #_refine_ls_R_factor_ref 0.1207 _refine_ls_wR_factor_ref 0.2004 _refine_ls_goodness_of_fit_ref 0.9155 #_reflns_number_all 1688 _refine_ls_R_factor_all 0.1207 _refine_ls_wR_factor_all 0.2004 # 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 875 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_gt 0.1388 _refine_ls_shift/su_max 0.000225 # 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: 73.2 100. 50.6 9.12 -0.640 ; _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. These hydroxy hydrogen positions were then refined subject to O-H distance restraints of 0.84(5) Angstroms and X-O-H angle restraints of 105(1) degrees for H11 and H12 and 110(1) degrees for H51 and H52. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Global vibration restraints were also applied due to the low quality and completeness of the data. Checkcif Output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.40 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.31 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.47 088_ALERT_3_B Poor Data / Parameter Ratio .................... 6.37 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 16 335_ALERT_2_C Large Benzene C-C Range C42 -C92 0.19 Ang. 360_ALERT_2_C Short C(sp3)-C(sp3) Bond C612 - C632 ... 1.41 Ang. These alerts are due to the relatively low completeness and quality of the data. 732_ALERT_1_B Angle Calc 110(5), Rep 109.9(10) ...... 5.00 su-Ra C52 -O52 -H52 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 110(3), Rep 110.0(10) ...... 3.00 su-Ra C51 -O51 -H51 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 105(3), Rep 105.0(10) ...... 3.00 su-Ra N22 -O12 -H12 1.555 1.555 1.555 These alerts are due to the fact that PLATON calculates esds using only the variances whereas CRYSTALS uses the full variance/covariance matrix. In this case restraints have been applied to the angles and this affects the esds. 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.94 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.30 This is probably due to the lack of information in one direction which occurs as a result of the Merrill-Bassett diamond-anvil cell shading a significant region of reciprocal space. The effect of this shading is often to cause a smearing out of electron density in one particular direction. 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 #------------------------------------------------------------------------------- 14.09 0.500 0.460 2158 992 1166 15.53 0.550 0.443 2852 1264 1588 16.99 0.600 0.418 3695 1543 2152 #----------------------------------------------------------- ACTA Min. Res. ---- 17.75 0.626 0.403 4210 1697 2513 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O11 O 0.9479(8) 0.1015(4) -0.2056(7) 0.0958 1.0000 Uani D U . . . . N21 N 0.8271(8) 0.0918(3) -0.1026(8) 0.0787 1.0000 Uani D U . . . . C31 C 0.6358(9) 0.1385(4) -0.1073(9) 0.0714 1.0000 Uani . U . . . . C41 C 0.4857(10) 0.1427(4) -0.0098(11) 0.0657 1.0000 Uani . U . . . . C51 C 0.5307(9) 0.0976(4) 0.0931(11) 0.0624 1.0000 Uani D U . . . . O51 O 0.7331(6) 0.0424(3) 0.1079(7) 0.0774 1.0000 Uani D U . . . . C61 C 0.3862(9) 0.1057(5) 0.1863(11) 0.0640 1.0000 Uani . U . . . . C611 C 0.4403(10) 0.0591(5) 0.3013(12) 0.0719 1.0000 Uani . U . . . . C621 C 0.4937(10) -0.0682(5) 0.3319(11) 0.0804 1.0000 Uani . U . . . . C631 C 0.6268(11) 0.1121(6) 0.3050(12) 0.0854 1.0000 Uani . U . . . . C641 C 0.2553(14) 0.0818(7) 0.3887(13) 0.1143 1.0000 Uani . U . . . . C71 C 0.1849(11) 0.1599(5) 0.1687(13) 0.0725 1.0000 Uani . U . . . . C81 C 0.1339(11) 0.2028(6) 0.0687(13) 0.0766 1.0000 Uani . U . . . . C91 C 0.2809(9) 0.1950(4) -0.0201(10) 0.0729 1.0000 Uani . U . . . . O12 O 0.3926(10) 0.3542(5) 0.6934(11) 0.0803 1.0000 Uani D U . . . . N22 N 0.3349(11) 0.3841(5) 0.5947(12) 0.0619 1.0000 Uani D U . . . . C32 C 0.1833(10) 0.3331(5) 0.5974(12) 0.0605 1.0000 Uani . U . . . . C42 C 0.0997(9) 0.3485(4) 0.5057(12) 0.0564 1.0000 Uani . U . . . . C52 C 0.1814(9) 0.4157(4) 0.3945(11) 0.0530 1.0000 Uani D U . . . . O52 O 0.3534(6) 0.4696(3) 0.3861(8) 0.0691 1.0000 Uani D U . . . . C62 C 0.1006(10) 0.4256(5) 0.3081(12) 0.0590 1.0000 Uani . U . . . . C612 C 0.2073(9) 0.4922(4) 0.1926(12) 0.0640 1.0000 Uani . U . . . . C622 C 0.1952(11) 0.6162(5) 0.1818(11) 0.0765 1.0000 Uani . U . . . . C632 C 0.4360(11) 0.4412(6) 0.1692(11) 0.0899 1.0000 Uani . U . . . . C642 C 0.0953(11) 0.4887(6) 0.1166(13) 0.0746 1.0000 Uani . U . . . . C72 C -0.0755(8) 0.3728(4) 0.3249(9) 0.0621 1.0000 Uani . U . . . . C82 C -0.1640(11) 0.3078(6) 0.4358(13) 0.0647 1.0000 Uani . U . . . . C92 C -0.0793(10) 0.2971(6) 0.5157(13) 0.0662 1.0000 Uani . U . . . . H11 H 1.071(8) 0.065(7) -0.1945(17) 0.1281 1.0000 Uiso D . . . . . H31 H 0.5928 0.1711 -0.1736 0.0790 1.0000 Uiso R . . . . . H51 H 0.816(6) 0.049(6) 0.045(3) 0.1058 1.0000 Uiso D . . . . . H6211 H 0.5535 -0.0956 0.3960 0.1120 1.0000 Uiso R . . . . . H6212 H 0.3697 -0.1037 0.3451 0.1119 1.0000 Uiso R . . . . . H6213 H 0.5945 -0.0873 0.2741 0.1119 1.0000 Uiso R . . . . . H6311 H 0.6657 0.0775 0.3750 0.1320 1.0000 Uiso R . . . . . H6312 H 0.5866 0.1906 0.2930 0.1320 1.0000 Uiso R . . . . . H6313 H 0.7475 0.1008 0.2501 0.1318 1.0000 Uiso R . . . . . H6411 H 0.3036 0.0618 0.4558 0.1530 1.0000 Uiso R . . . . . H6412 H 0.1452 0.0367 0.3986 0.1528 1.0000 Uiso R . . . . . H6413 H 0.1997 0.1597 0.3666 0.1530 1.0000 Uiso R . . . . . H71 H 0.0822 0.1661 0.2279 0.0828 1.0000 Uiso R . . . . . H81 H -0.0025 0.2375 0.0610 0.0869 1.0000 Uiso R . . . . . H91 H 0.2456 0.2251 -0.0886 0.0809 1.0000 Uiso R . . . . . H12 H 0.464(11) 0.406(4) 0.688(3) 0.1159 1.0000 Uiso D . . . . . H32 H 0.1231 0.2844 0.6637 0.0688 1.0000 Uiso R . . . . . H52 H 0.405(10) 0.441(6) 0.442(5) 0.0970 1.0000 Uiso D . . . . . H6221 H 0.2638 0.6563 0.1102 0.1100 1.0000 Uiso R . . . . . H6222 H 0.0492 0.6484 0.1929 0.1102 1.0000 Uiso R . . . . . H6223 H 0.2651 0.6225 0.2342 0.1099 1.0000 Uiso R . . . . . H6321 H 0.5020 0.4791 0.0964 0.1200 1.0000 Uiso R . . . . . H6322 H 0.4398 0.3636 0.1774 0.1199 1.0000 Uiso R . . . . . H6323 H 0.5131 0.4479 0.2183 0.1200 1.0000 Uiso R . . . . . H6421 H 0.1663 0.5265 0.0446 0.1110 1.0000 Uiso R . . . . . H6422 H -0.0466 0.5242 0.1300 0.1107 1.0000 Uiso R . . . . . H6423 H 0.0899 0.4120 0.1237 0.1107 1.0000 Uiso R . . . . . H72 H -0.1374 0.3781 0.2676 0.0730 1.0000 Uiso R . . . . . H82 H -0.2855 0.2743 0.4481 0.0792 1.0000 Uiso R . . . . . H92 H -0.1387 0.2513 0.5845 0.0758 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 0.068(3) 0.063(2) 0.122(11) -0.025(4) 0.041(5) -0.012(2) N21 0.061(2) 0.039(2) 0.107(10) -0.013(3) 0.026(4) -0.0148(17) C31 0.060(2) 0.034(2) 0.099(8) -0.016(3) 0.024(4) -0.0195(18) C41 0.049(2) 0.031(2) 0.093(7) -0.006(4) 0.017(3) -0.0159(17) C51 0.043(2) 0.030(2) 0.096(7) -0.014(4) 0.015(3) -0.0103(16) O51 0.0436(18) 0.058(2) 0.109(9) -0.019(3) 0.013(3) -0.0034(15) C61 0.045(2) 0.038(2) 0.099(7) -0.023(3) 0.014(3) -0.0154(18) C611 0.051(3) 0.050(2) 0.096(7) -0.019(4) 0.017(4) -0.008(2) C621 0.066(4) 0.050(2) 0.105(11) -0.016(3) 0.009(5) -0.010(2) C631 0.086(4) 0.062(3) 0.111(13) -0.035(6) -0.010(5) -0.014(3) C641 0.097(5) 0.100(5) 0.107(9) -0.033(7) 0.033(6) 0.012(4) C71 0.047(2) 0.049(3) 0.109(9) -0.024(5) 0.013(4) -0.010(2) C81 0.048(3) 0.051(4) 0.113(9) -0.023(5) 0.007(4) -0.002(2) C91 0.054(2) 0.040(2) 0.105(9) -0.014(4) 0.008(3) -0.0088(19) O12 0.074(4) 0.072(3) 0.086(13) -0.003(6) -0.015(5) -0.030(3) N22 0.061(3) 0.049(3) 0.075(12) -0.023(5) 0.004(4) -0.020(3) C32 0.045(3) 0.047(3) 0.080(9) -0.018(5) 0.006(4) -0.012(3) C42 0.036(3) 0.036(2) 0.087(9) -0.014(4) 0.000(3) -0.008(2) C52 0.034(3) 0.032(2) 0.086(8) -0.018(4) 0.003(3) -0.008(2) O52 0.042(2) 0.058(2) 0.095(10) -0.005(3) -0.005(3) -0.0248(17) C62 0.042(3) 0.044(2) 0.087(8) -0.023(4) 0.002(3) -0.009(2) C612 0.045(2) 0.042(2) 0.091(8) -0.007(4) -0.008(4) -0.005(2) C622 0.082(4) 0.046(2) 0.092(14) -0.010(4) -0.010(6) -0.019(3) C632 0.055(3) 0.095(4) 0.090(15) -0.019(6) 0.010(5) 0.009(3) C642 0.067(4) 0.065(4) 0.089(9) -0.026(5) -0.004(5) -0.013(3) C72 0.040(2) 0.050(3) 0.092(9) -0.023(4) -0.002(3) -0.0080(19) C82 0.042(3) 0.062(3) 0.093(10) -0.036(5) 0.010(4) -0.021(3) C92 0.043(3) 0.054(3) 0.092(10) -0.015(5) 0.001(4) -0.019(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.98(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 O11 . N21 . 1.399(10) yes O11 . H11 . 0.87(4) no N21 . C31 . 1.290(9) yes C31 . C41 . 1.451(12) yes C31 . H31 . 0.931 no C41 . C51 . 1.383(19) yes C41 . C91 . 1.398(11) yes C51 . O51 . 1.405(10) yes C51 . C61 . 1.404(13) yes O51 . H51 . 0.87(4) no C61 . C611 . 1.553(19) yes C61 . C71 . 1.403(13) yes C611 . C621 . 1.531(8) yes C611 . C631 . 1.527(13) yes C611 . C641 . 1.538(12) yes C621 . H6211 . 0.960 no C621 . H6212 . 0.957 no C621 . H6213 . 0.964 no C631 . H6311 . 0.964 no C631 . H6312 . 0.959 no C631 . H6313 . 0.972 no C641 . H6411 . 0.963 no C641 . H6412 . 0.966 no C641 . H6413 . 0.963 no C71 . C81 . 1.36(2) yes C71 . H71 . 0.929 no C81 . C91 . 1.366(14) yes C81 . H81 . 0.933 no C91 . H91 . 0.935 no O12 . N22 . 1.375(17) yes O12 . H12 . 0.86(4) no N22 . C32 . 1.278(12) yes C32 . C42 . 1.407(19) yes C32 . H32 . 0.935 no C42 . C52 . 1.468(18) yes C42 . C92 . 1.410(10) yes C52 . O52 . 1.396(8) yes C52 . C62 . 1.349(19) yes O52 . H52 . 0.84(5) no C62 . C612 . 1.551(17) yes C62 . C72 . 1.382(9) yes C612 . C622 . 1.536(7) yes C612 . C632 . 1.524(8) yes C612 . C642 . 1.41(2) yes C622 . H6221 . 0.963 no C622 . H6222 . 0.967 no C622 . H6223 . 0.963 no C632 . H6321 . 0.962 no C632 . H6322 . 0.960 no C632 . H6323 . 0.959 no C642 . H6421 . 0.964 no C642 . H6422 . 0.961 no C642 . H6423 . 0.963 no C72 . C82 . 1.468(17) yes C72 . H72 . 0.932 no C82 . C92 . 1.28(2) yes C82 . H82 . 0.930 no C92 . H92 . 0.941 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 . 105.0(10) no O11 . N21 . C31 . 111.5(9) yes N21 . C31 . C41 . 120.7(11) yes N21 . C31 . H31 . 120.3 no C41 . C31 . H31 . 119.0 no C31 . C41 . C51 . 124.4(7) yes C31 . C41 . C91 . 118.0(12) yes C51 . C41 . C91 . 117.6(8) yes C41 . C51 . O51 . 119.8(7) yes C41 . C51 . C61 . 123.8(7) yes O51 . C51 . C61 . 116.5(12) yes C51 . O51 . H51 . 110.0(10) no C51 . C61 . C611 . 123.6(7) yes C51 . C61 . C71 . 114.9(13) yes C611 . C61 . C71 . 121.5(9) yes C61 . C611 . C621 . 109.1(10) yes C61 . C611 . C631 . 110.6(8) yes C621 . C611 . C631 . 110.1(8) yes C61 . C611 . C641 . 113.1(9) yes C621 . C611 . C641 . 106.7(7) yes C631 . C611 . C641 . 107.2(11) yes C611 . C621 . H6211 . 109.3 no C611 . C621 . H6212 . 110.9 no H6211 . C621 . H6212 . 108.9 no C611 . C621 . H6213 . 110.0 no H6211 . C621 . H6213 . 109.1 no H6212 . C621 . H6213 . 108.5 no C611 . C631 . H6311 . 109.3 no C611 . C631 . H6312 . 109.4 no H6311 . C631 . H6312 . 109.3 no C611 . C631 . H6313 . 110.2 no H6311 . C631 . H6313 . 108.8 no H6312 . C631 . H6313 . 109.8 no C611 . C641 . H6411 . 109.5 no C611 . C641 . H6412 . 109.1 no H6411 . C641 . H6412 . 109.0 no C611 . C641 . H6413 . 109.8 no H6411 . C641 . H6413 . 110.1 no H6412 . C641 . H6413 . 109.2 no C61 . C71 . C81 . 122.8(10) yes C61 . C71 . H71 . 118.4 no C81 . C71 . H71 . 118.8 no C71 . C81 . C91 . 120.3(8) yes C71 . C81 . H81 . 119.7 no C91 . C81 . H81 . 120.0 no C41 . C91 . C81 . 120.6(12) yes C41 . C91 . H91 . 119.3 no C81 . C91 . H91 . 120.0 no N22 . O12 . H12 . 105.0(10) no O12 . N22 . C32 . 112.8(11) yes N22 . C32 . C42 . 123.1(12) yes N22 . C32 . H32 . 118.5 no C42 . C32 . H32 . 118.4 no C32 . C42 . C52 . 126.1(7) yes C32 . C42 . C92 . 120.3(11) yes C52 . C42 . C92 . 113.7(13) yes C42 . C52 . O52 . 113.1(12) yes C42 . C52 . C62 . 124.3(7) yes O52 . C52 . C62 . 122.6(10) yes C52 . O52 . H52 . 109.9(10) no C52 . C62 . C612 . 120.5(7) yes C52 . C62 . C72 . 118.4(10) yes C612 . C62 . C72 . 121.1(13) yes C62 . C612 . C622 . 110.2(9) yes C62 . C612 . C632 . 109.4(9) yes C622 . C612 . C632 . 111.1(5) yes C62 . C612 . C642 . 109.5(7) yes C622 . C612 . C642 . 106.4(10) yes C632 . C612 . C642 . 110.1(11) yes C612 . C622 . H6221 . 109.3 no C612 . C622 . H6222 . 110.2 no H6221 . C622 . H6222 . 108.5 no C612 . C622 . H6223 . 109.4 no H6221 . C622 . H6223 . 109.6 no H6222 . C622 . H6223 . 109.9 no C612 . C632 . H6321 . 110.4 no C612 . C632 . H6322 . 109.7 no H6321 . C632 . H6322 . 108.5 no C612 . C632 . H6323 . 109.7 no H6321 . C632 . H6323 . 109.0 no H6322 . C632 . H6323 . 109.6 no C612 . C642 . H6421 . 109.5 no C612 . C642 . H6422 . 109.4 no H6421 . C642 . H6422 . 110.3 no C612 . C642 . H6423 . 109.6 no H6421 . C642 . H6423 . 109.2 no H6422 . C642 . H6423 . 108.9 no C62 . C72 . C82 . 118.3(12) yes C62 . C72 . H72 . 121.3 no C82 . C72 . H72 . 120.4 no C72 . C82 . C92 . 121.7(7) yes C72 . C82 . H82 . 118.8 no C92 . C82 . H82 . 119.5 no C42 . C92 . C82 . 123.6(13) yes C42 . C92 . H92 . 118.5 no C82 . C92 . H92 . 117.9 no _chemical_name_common 3-tButylsalicylaldoxime #END data_tBu10kbar _database_code_depnum_ccdc_archive 'CCDC 657070' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of hexane/chloroform solution' _audit_creation_date 06-12-18 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-tButylsalicylaldoxime _chemical_melting_point ? _cell_length_a 14.811(3) _cell_length_b 6.4564(7) _cell_length_c 19.759(4) _cell_angle_alpha 90 _cell_angle_beta 94.060(8) _cell_angle_gamma 90 _cell_volume 1884.7(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' 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 -x+1/2,y,-z x+1/2,-y,z -x+1,y+1/2,-z+1/2 x+1,-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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C11 H15 N1 O2 # Dc = 1.36 Fooo = 832.00 Mu = 0.94 M = 193.25 # Found Formula = C11 H15 N1 O2 # Dc = 1.36 FOOO = 832.00 Mu = 0.94 M = 193.25 _chemical_formula_sum 'C11 H15 N1 O2' _chemical_formula_moiety 'C11 H15 N1 O2' _chemical_formula_weight 193.25 _cell_measurement_reflns_used 1386 _cell_measurement_theta_min 2 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.094 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.14 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48690 _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_ambient_pressure 1000000 _diffrn_reflns_number 8727 _reflns_number_total 1163 _diffrn_reflns_av_R_equivalents 0.125 # Number of reflections with Friedels Law is 1220 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1940 _diffrn_reflns_theta_min 2.274 _diffrn_reflns_theta_max 17.757 _diffrn_measured_fraction_theta_max 0.600 _diffrn_reflns_theta_full 13.496 _diffrn_measured_fraction_theta_full 0.677 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -14 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _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 -0.16 _refine_diff_density_max 0.16 _refine_ls_number_reflns 1163 _refine_ls_number_restraints 4 _refine_ls_number_parameters 134 #_refine_ls_R_factor_ref 0.1138 _refine_ls_wR_factor_ref 0.2058 _refine_ls_goodness_of_fit_ref 0.9548 #_reflns_number_all 1163 _refine_ls_R_factor_all 0.1138 _refine_ls_wR_factor_all 0.2058 # 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 630 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_gt 0.1603 _refine_ls_shift/su_max 0.001168 # 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: 79.1 113. 60.5 15.2 0.141 ; _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. These hydroxy hydrogen positions were then refined subject to O-H distance restraints of 0.84(5) Angstroms and X-O-H angle restraints of 105(1) degrees for H1 and 110(1) degrees for H5. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Checkcif output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.63 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.50 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.68 088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.68 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 415_ALERT_2_B Short Inter D-H..H-X H1 .. H623 .. 2.00 Ang. Short contacts are expected at high pressure. 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 These alerts are due to the relatively low completeness and quality of the data. 220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio 242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C61 These alerts are due to the greater flexibility of the tButyl group compared to the rest of the structure, as such the tButyl group atoms have larger thermal parameters. 128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a The non-standard setting was used for refinement due to the large beta angle which arises in the C2/c setting. 152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? This appears to be due to a simple rounding error. 732_ALERT_1_C Angle Calc 110(3), Rep 109.7(10) ...... 3.00 su-Ra C5 -O5 -H5 1.555 1.555 1.555 This alert is due to the fact that PLATON calculates esds using only the variances whereas CRYSTALS uses the full variance/covariance matrix. In this case a restraint has been applied to the angle and this affects the esd. 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 #------------------------------------------------------------------------------- 14.09 0.500 0.677 995 674 321 15.53 0.550 0.652 1312 855 457 16.99 0.600 0.624 1703 1062 641 #----------------------------------------------------------- ACTA Min. Res. ---- 17.76 0.626 0.600 1938 1163 775 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.0861(3) 0.3390(5) 0.2886(2) 0.0479 1.0000 Uani D . . . . . N2 N 0.1494(3) 0.4261(5) 0.2462(2) 0.0377 1.0000 Uani D . . . . . C3 C 0.1225(4) 0.6052(6) 0.2241(3) 0.0377 1.0000 Uani . . . . . . C4 C 0.1755(4) 0.7224(6) 0.1783(3) 0.0291 1.0000 Uani . . . . . . C5 C 0.2543(4) 0.6513(6) 0.1533(3) 0.0313 1.0000 Uani D . . . . . O5 O 0.2858(3) 0.4578(4) 0.1735(2) 0.0486 1.0000 Uani D . . . . . C6 C 0.3043(4) 0.7653(6) 0.1088(3) 0.0363 1.0000 Uani . . . . . . C61 C 0.3896(4) 0.6854(6) 0.0794(3) 0.0380 1.0000 Uani . . . . . . C62 C 0.4622(4) 0.6285(8) 0.1347(3) 0.0595 1.0000 Uani . . . . . . C63 C 0.3664(6) 0.4967(10) 0.0342(4) 0.0837 1.0000 Uani . . . . . . C64 C 0.4335(6) 0.8514(9) 0.0379(4) 0.0718 1.0000 Uani . . . . . . C7 C 0.2689(4) 0.9622(6) 0.0910(3) 0.0450 1.0000 Uani . . . . . . C8 C 0.1906(4) 1.0375(6) 0.1164(3) 0.0363 1.0000 Uani . . . . . . C9 C 0.1421(4) 0.9192(6) 0.1596(3) 0.0417 1.0000 Uani . . . . . . H1 H 0.115(2) 0.234(7) 0.308(2) 0.0733 1.0000 Uiso D . . . . . H3 H 0.0682 0.6602 0.2370 0.0463 1.0000 Uiso R . . . . . H5 H 0.248(3) 0.400(5) 0.199(3) 0.0730 1.0000 Uiso D . . . . . H621 H 0.5091 0.5558 0.1132 0.0889 1.0000 Uiso R . . . . . H622 H 0.4875 0.7531 0.1560 0.0890 1.0000 Uiso R . . . . . H623 H 0.4371 0.5400 0.1686 0.0889 1.0000 Uiso R . . . . . H631 H 0.4208 0.4407 0.0177 0.1252 1.0000 Uiso R . . . . . H632 H 0.3259 0.5361 -0.0038 0.1248 1.0000 Uiso R . . . . . H633 H 0.3385 0.3924 0.0610 0.1249 1.0000 Uiso R . . . . . H641 H 0.4897 0.7992 0.0234 0.1103 1.0000 Uiso R . . . . . H642 H 0.4447 0.9750 0.0649 0.1104 1.0000 Uiso R . . . . . H643 H 0.3932 0.8800 -0.0015 0.1101 1.0000 Uiso R . . . . . H7 H 0.3002 1.0460 0.0618 0.0541 1.0000 Uiso R . . . . . H8 H 0.1699 1.1693 0.1038 0.0441 1.0000 Uiso R . . . . . H9 H 0.0894 0.9692 0.1762 0.0502 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 0.034(3) 0.057(2) 0.055(3) 0.0149(16) 0.022(3) -0.0020(15) N2 0.031(4) 0.046(2) 0.039(3) 0.0006(16) 0.019(3) -0.0037(16) C3 0.029(4) 0.043(2) 0.043(4) -0.0058(18) 0.008(4) -0.0009(18) C4 0.023(4) 0.039(2) 0.028(3) -0.0035(16) 0.015(3) -0.0025(18) C5 0.028(4) 0.035(2) 0.033(4) -0.0022(16) 0.013(3) 0.0031(18) O5 0.048(3) 0.0356(17) 0.063(3) 0.0091(14) 0.009(3) 0.0045(13) C6 0.030(4) 0.042(2) 0.037(4) 0.0059(17) 0.007(4) -0.0071(19) C61 0.038(5) 0.046(3) 0.034(4) 0.0089(18) 0.023(4) 0.0008(19) C62 0.043(5) 0.069(3) 0.067(5) 0.013(3) 0.003(5) 0.001(2) C63 0.067(6) 0.099(5) 0.085(7) -0.043(4) 0.004(6) 0.012(4) C64 0.062(7) 0.094(5) 0.064(6) 0.034(4) 0.037(6) 0.021(3) C7 0.043(4) 0.043(2) 0.050(4) 0.005(2) 0.007(4) -0.001(2) C8 0.040(4) 0.038(2) 0.033(4) 0.0006(17) 0.015(4) 0.002(2) C9 0.035(4) 0.038(2) 0.053(4) 0.0012(19) 0.006(4) 0.0048(18) _refine_ls_extinction_coef 1600(200) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.859(13) 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 . 1.418(7) yes O1 . H1 . 0.87(4) no N2 . C3 . 1.288(5) yes C3 . C4 . 1.453(9) yes C3 . H3 . 0.931 no C4 . C5 . 1.378(9) yes C4 . C9 . 1.404(6) yes C5 . O5 . 1.383(5) yes C5 . C6 . 1.399(9) yes O5 . H5 . 0.86(4) no C6 . C61 . 1.517(9) yes C6 . C7 . 1.410(6) yes C61 . C62 . 1.522(6) yes C61 . C63 . 1.535(7) yes C61 . C64 . 1.523(9) yes C62 . H621 . 0.962 no C62 . H622 . 0.971 no C62 . H623 . 0.974 no C63 . H631 . 0.962 no C63 . H632 . 0.961 no C63 . H633 . 0.966 no C64 . H641 . 0.960 no C64 . H642 . 0.968 no C64 . H643 . 0.964 no C7 . C8 . 1.383(9) yes C7 . H7 . 0.937 no C8 . C9 . 1.385(9) yes C8 . H8 . 0.933 no C9 . H9 . 0.925 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 . 104.4(10) no O1 . N2 . C3 . 110.8(5) yes N2 . C3 . C4 . 120.7(6) yes N2 . C3 . H3 . 120.2 no C4 . C3 . H3 . 119.1 no C3 . C4 . C5 . 123.9(4) yes C3 . C4 . C9 . 116.1(6) yes C5 . C4 . C9 . 120.0(6) yes C4 . C5 . O5 . 118.3(5) yes C4 . C5 . C6 . 123.4(4) yes O5 . C5 . C6 . 118.3(6) yes C5 . O5 . H5 . 109.7(10) no C5 . C6 . C61 . 123.7(4) yes C5 . C6 . C7 . 115.2(6) yes C61 . C6 . C7 . 121.1(5) yes C6 . C61 . C62 . 111.8(5) yes C6 . C61 . C63 . 109.5(5) yes C62 . C61 . C63 . 110.1(4) yes C6 . C61 . C64 . 111.4(5) yes C62 . C61 . C64 . 104.4(5) yes C63 . C61 . C64 . 109.4(7) yes C61 . C62 . H621 . 107.3 no C61 . C62 . H622 . 110.1 no H621 . C62 . H622 . 109.0 no C61 . C62 . H623 . 110.6 no H621 . C62 . H623 . 109.8 no H622 . C62 . H623 . 109.9 no C61 . C63 . H631 . 109.7 no C61 . C63 . H632 . 110.2 no H631 . C63 . H632 . 109.1 no C61 . C63 . H633 . 108.8 no H631 . C63 . H633 . 108.9 no H632 . C63 . H633 . 110.2 no C61 . C64 . H641 . 109.0 no C61 . C64 . H642 . 110.3 no H641 . C64 . H642 . 109.6 no C61 . C64 . H643 . 107.8 no H641 . C64 . H643 . 109.1 no H642 . C64 . H643 . 111.1 no C6 . C7 . C8 . 122.2(6) yes C6 . C7 . H7 . 118.8 no C8 . C7 . H7 . 119.0 no C7 . C8 . C9 . 121.0(5) yes C7 . C8 . H8 . 119.5 no C9 . C8 . H8 . 119.5 no C4 . C9 . C8 . 118.2(7) yes C4 . C9 . H9 . 120.9 no C8 . C9 . H9 . 120.9 no _chemical_name_common 3-tButylsalicylaldoxime #END data_tBu23kbar _database_code_depnum_ccdc_archive 'CCDC 657071' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of hexane/chloroform solution' _audit_creation_date 06-12-18 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-tButylsalicylaldoxime _chemical_melting_point ? _cell_length_a 14.5745(13) _cell_length_b 6.3779(4) _cell_length_c 19.0922(18) _cell_angle_alpha 90 _cell_angle_beta 94.882(4) _cell_angle_gamma 90 _cell_volume 1768.3(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' 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 -x+1/2,y,-z x+1/2,-y,z -x+1,y+1/2,-z+1/2 x+1,-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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C11 H15 N1 O2 # Dc = 1.45 Fooo = 832.00 Mu = 1.00 M = 193.25 # Found Formula = C11 H15 N1 O2 # Dc = 1.45 FOOO = 832.00 Mu = 1.00 M = 193.25 _chemical_formula_sum 'C11 H15 N1 O2' _chemical_formula_moiety 'C11 H15 N1 O2' _chemical_formula_weight 193.25 _cell_measurement_reflns_used 1508 _cell_measurement_theta_min 2 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.100 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.18 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48690 _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 'Model taken from 10kbar structure' _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_ambient_pressure 2300000 _diffrn_reflns_number 8098 _reflns_number_total 1055 _diffrn_reflns_av_R_equivalents 0.125 # Number of reflections with Friedels Law is 1110 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1819 _diffrn_reflns_theta_min 2.307 _diffrn_reflns_theta_max 17.753 _diffrn_measured_fraction_theta_max 0.584 _diffrn_reflns_theta_full 13.315 _diffrn_measured_fraction_theta_full 0.649 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -14 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _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 -0.26 _refine_diff_density_max 0.23 _refine_ls_number_reflns 1055 _refine_ls_number_restraints 4 _refine_ls_number_parameters 134 #_refine_ls_R_factor_ref 0.1063 _refine_ls_wR_factor_ref 0.2247 _refine_ls_goodness_of_fit_ref 0.9844 #_reflns_number_all 1055 _refine_ls_R_factor_all 0.1063 _refine_ls_wR_factor_all 0.2247 # 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 628 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_gt 0.1715 _refine_ls_shift/su_max 0.000056 # 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: 140. 223. 141. 60.5 15.0 ; _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. These hydroxy hydrogen positions were then refined subject to O-H distance restraints of 0.84(5) Angstroms and X-O-H angle restraints of 105(1) degrees for H1 and 110(1) degrees for H5. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Checkcif Output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.61 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.31 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.65 088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.87 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 413_ALERT_2_B Short Inter XH3 .. XHn H631 .. H641 .. 2.08 Ang. 415_ALERT_2_B Short Inter D-H..H-X H1 .. H623 .. 1.96 Ang. 432_ALERT_2_B Short Inter X...Y Contact C64 .. C64 .. 3.01 Ang. 432_ALERT_2_C Short Inter X...Y Contact C3 .. C62 .. 3.10 Ang. Short contacts are expected at high pressure. 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.33 su 230_ALERT_2_C Hirshfeld Test Diff for C6 - C61 .. 5.46 su 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 These alerts are due to the relatively low completeness and quality of the data. 128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a The non-standard setting was used for refinement due to the large beta angle which arises in the C2/c setting. 220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio This alert is due to the greater flexibility of the tButyl group compared to the rest of the structure, as such the tButyl group atoms have larger thermal parameters. 732_ALERT_1_C Angle Calc 110(3), Rep 109.8(10) ...... 3.00 su-Ra C5 -O5 -H5 1.555 1.555 1.555 This alert is due to the fact that PLATON calculates esds using only the variances whereas CRYSTALS uses the full variance/covariance matrix. In this case a restraint has been applied to the angle and this affects the esd. 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 #------------------------------------------------------------------------------- 14.09 0.500 0.644 923 594 329 15.53 0.550 0.627 1230 771 459 16.99 0.600 0.601 1601 963 638 #----------------------------------------------------------- ACTA Min. Res. ---- 17.75 0.626 0.584 1808 1055 753 ; 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 0.0847(3) 0.3417(5) 0.2920(2) 0.0353 1.0000 Uani D . . . . . N2 N 0.1480(3) 0.4263(5) 0.2483(2) 0.0267 1.0000 Uani D . . . . . C3 C 0.1203(4) 0.6098(6) 0.2265(3) 0.0288 1.0000 Uani . . . . . . C4 C 0.1748(4) 0.7274(6) 0.1784(3) 0.0264 1.0000 Uani . . . . . . C5 C 0.2544(4) 0.6512(6) 0.1529(3) 0.0337 1.0000 Uani D . . . . . O5 O 0.2856(3) 0.4557(4) 0.1725(2) 0.0339 1.0000 Uani D . . . . . C6 C 0.3050(4) 0.7697(6) 0.1077(3) 0.0206 1.0000 Uani . . . . . . C61 C 0.3910(4) 0.6848(6) 0.0769(3) 0.0334 1.0000 Uani . . . . . . C62 C 0.4654(4) 0.6186(7) 0.1346(3) 0.0411 1.0000 Uani . . . . . . C63 C 0.3669(5) 0.5005(10) 0.0288(4) 0.0536 1.0000 Uani . . . . . . C64 C 0.4378(5) 0.8537(9) 0.0360(4) 0.0538 1.0000 Uani . . . . . . C7 C 0.2695(4) 0.9685(6) 0.0899(3) 0.0317 1.0000 Uani . . . . . . C8 C 0.1914(4) 1.0472(6) 0.1144(3) 0.0280 1.0000 Uani . . . . . . C9 C 0.1412(4) 0.9270(6) 0.1597(3) 0.0270 1.0000 Uani . . . . . . H1 H 0.113(2) 0.245(8) 0.314(2) 0.0574 1.0000 Uiso D . . . . . H3 H 0.0660 0.6677 0.2404 0.0364 1.0000 Uiso R . . . . . H5 H 0.246(3) 0.393(5) 0.195(3) 0.0533 1.0000 Uiso D . . . . . H621 H 0.5126 0.5404 0.1136 0.0653 1.0000 Uiso R . . . . . H622 H 0.4935 0.7407 0.1586 0.0650 1.0000 Uiso R . . . . . H623 H 0.4390 0.5312 0.1691 0.0650 1.0000 Uiso R . . . . . H631 H 0.4226 0.4318 0.0176 0.0833 1.0000 Uiso R . . . . . H632 H 0.3330 0.5485 -0.0141 0.0828 1.0000 Uiso R . . . . . H633 H 0.3306 0.4001 0.0529 0.0831 1.0000 Uiso R . . . . . H641 H 0.4952 0.7994 0.0216 0.0860 1.0000 Uiso R . . . . . H642 H 0.4508 0.9772 0.0652 0.0861 1.0000 Uiso R . . . . . H643 H 0.3982 0.8921 -0.0051 0.0860 1.0000 Uiso R . . . . . H7 H 0.3015 1.0508 0.0600 0.0400 1.0000 Uiso R . . . . . H8 H 0.1704 1.1815 0.1010 0.0367 1.0000 Uiso R . . . . . H9 H 0.0878 0.9785 0.1773 0.0340 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 0.020(3) 0.0453(19) 0.043(3) 0.0134(15) 0.017(3) -0.0045(14) N2 0.023(4) 0.0335(19) 0.025(3) 0.0011(14) 0.009(3) -0.0054(15) C3 0.026(4) 0.030(2) 0.030(3) -0.0014(16) 0.001(4) 0.0003(17) C4 0.027(4) 0.027(2) 0.024(3) -0.0024(15) -0.002(4) 0.0009(17) C5 0.039(5) 0.0210(19) 0.038(4) 0.0058(17) -0.013(4) -0.0049(19) O5 0.027(3) 0.0225(14) 0.054(3) 0.0083(12) 0.010(2) 0.0030(11) C6 0.020(4) 0.028(2) 0.016(3) -0.0030(14) 0.012(3) 0.0031(16) C61 0.031(5) 0.037(2) 0.033(4) 0.0115(18) 0.005(4) -0.0015(18) C62 0.027(5) 0.052(3) 0.045(4) 0.013(2) 0.004(4) 0.000(2) C63 0.036(6) 0.082(4) 0.045(5) -0.025(3) 0.015(5) 0.008(3) C64 0.034(6) 0.070(4) 0.062(6) 0.033(3) 0.025(5) 0.013(3) C7 0.029(4) 0.033(2) 0.033(4) 0.0082(18) 0.004(4) -0.0021(19) C8 0.027(4) 0.030(2) 0.028(4) 0.0021(17) 0.008(4) 0.0019(19) C9 0.024(4) 0.035(2) 0.023(3) -0.0030(16) 0.008(4) 0.0070(18) _refine_ls_extinction_coef 1600.328 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.868(12) 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 . 1.404(7) yes O1 . H1 . 0.84(4) no N2 . C3 . 1.295(5) yes C3 . C4 . 1.470(9) yes C3 . H3 . 0.933 no C4 . C5 . 1.383(10) yes C4 . C9 . 1.399(5) yes C5 . O5 . 1.368(5) yes C5 . C6 . 1.404(9) yes O5 . H5 . 0.85(4) no C6 . C61 . 1.527(9) yes C6 . C7 . 1.400(5) yes C61 . C62 . 1.538(5) yes C61 . C63 . 1.515(7) yes C61 . C64 . 1.526(9) yes C62 . H621 . 0.965 no C62 . H622 . 0.976 no C62 . H623 . 0.967 no C63 . H631 . 0.962 no C63 . H632 . 0.969 no C63 . H633 . 0.971 no C64 . H641 . 0.965 no C64 . H642 . 0.974 no C64 . H643 . 0.966 no C7 . C8 . 1.363(9) yes C7 . H7 . 0.929 no C8 . C9 . 1.408(10) yes C8 . H8 . 0.938 no C9 . H9 . 0.933 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 . 105.1(10) no O1 . N2 . C3 . 109.6(5) yes N2 . C3 . C4 . 119.5(6) yes N2 . C3 . H3 . 121.0 no C4 . C3 . H3 . 119.5 no C3 . C4 . C5 . 123.6(4) yes C3 . C4 . C9 . 115.3(6) yes C5 . C4 . C9 . 121.1(6) yes C4 . C5 . O5 . 119.6(5) yes C4 . C5 . C6 . 121.8(4) yes O5 . C5 . C6 . 118.6(6) yes C5 . O5 . H5 . 109.8(10) no C5 . C6 . C61 . 122.5(4) yes C5 . C6 . C7 . 115.7(6) yes C61 . C6 . C7 . 121.7(5) yes C6 . C61 . C62 . 111.9(5) yes C6 . C61 . C63 . 110.7(5) yes C62 . C61 . C63 . 109.5(4) yes C6 . C61 . C64 . 111.4(5) yes C62 . C61 . C64 . 104.0(5) yes C63 . C61 . C64 . 109.1(7) yes C61 . C62 . H621 . 109.2 no C61 . C62 . H622 . 111.0 no H621 . C62 . H622 . 108.7 no C61 . C62 . H623 . 110.4 no H621 . C62 . H623 . 108.9 no H622 . C62 . H623 . 108.4 no C61 . C63 . H631 . 109.4 no C61 . C63 . H632 . 110.0 no H631 . C63 . H632 . 109.7 no C61 . C63 . H633 . 109.4 no H631 . C63 . H633 . 108.0 no H632 . C63 . H633 . 110.4 no C61 . C64 . H641 . 109.1 no C61 . C64 . H642 . 110.5 no H641 . C64 . H642 . 108.8 no C61 . C64 . H643 . 109.4 no H641 . C64 . H643 . 109.4 no H642 . C64 . H643 . 109.5 no C6 . C7 . C8 . 123.5(6) yes C6 . C7 . H7 . 117.8 no C8 . C7 . H7 . 118.7 no C7 . C8 . C9 . 120.3(4) yes C7 . C8 . H8 . 120.4 no C9 . C8 . H8 . 119.4 no C8 . C9 . C4 . 117.6(6) yes C8 . C9 . H9 . 121.6 no C4 . C9 . H9 . 120.9 no _chemical_name_common 3-tButylsalicylaldoxime #END data_tBu34kbar _database_code_depnum_ccdc_archive 'CCDC 657072' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of hexane/chloroform solution' _audit_creation_date 06-12-18 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-tButylsalicylaldoxime _chemical_melting_point ? _cell_length_a 14.3941(14) _cell_length_b 6.3329(4) _cell_length_c 18.7250(19) _cell_angle_alpha 90 _cell_angle_beta 95.325(5) _cell_angle_gamma 90 _cell_volume 1699.5(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' 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 -x+1/2,y,-z x+1/2,-y,z -x+1,y+1/2,-z+1/2 x+1,-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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C11 H15 N1 O2 # Dc = 1.51 Fooo = 832.00 Mu = 1.04 M = 193.25 # Found Formula = C11 H15 N1 O2 # Dc = 1.51 FOOO = 832.00 Mu = 1.04 M = 193.25 _chemical_formula_sum 'C11 H15 N1 O2' _chemical_formula_moiety 'C11 H15 N1 O2' _chemical_formula_weight 193.25 _cell_measurement_reflns_used 1549 _cell_measurement_theta_min 3 _cell_measurement_theta_max 15 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.104 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.07 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48690 _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 'Model taken from 10kbar structure' _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_ambient_pressure 3400000 _diffrn_reflns_number 7914 _reflns_number_total 979 _diffrn_reflns_av_R_equivalents 0.106 # Number of reflections with Friedels Law is 1028 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1750 _diffrn_reflns_theta_min 2.327 _diffrn_reflns_theta_max 17.760 _diffrn_measured_fraction_theta_max 0.561 _diffrn_reflns_theta_full 13.320 _diffrn_measured_fraction_theta_full 0.625 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -12 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _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 -0.20 _refine_diff_density_max 0.18 _refine_ls_number_reflns 979 _refine_ls_number_restraints 4 _refine_ls_number_parameters 134 #_refine_ls_R_factor_ref 0.0920 _refine_ls_wR_factor_ref 0.1838 _refine_ls_goodness_of_fit_ref 0.9545 #_reflns_number_all 979 _refine_ls_R_factor_all 0.0920 _refine_ls_wR_factor_all 0.1838 # 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 637 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_gt 0.1438 _refine_ls_shift/su_max 0.000059 # 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: 116. 166. 108. 43.9 11.8 ; _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. These hydroxy hydrogen positions were then refined subject to O-H distance restraints of 0.84(5) Angstroms and X-O-H angle restraints of 105(1) degrees for H1 and 110(1) degrees for H5. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Checkcif Output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.59 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.32 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.63 088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.31 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 413_ALERT_2_B Short Inter XH3 .. XHn H631 .. H641 .. 2.04 Ang. 415_ALERT_2_B Short Inter D-H..H-X H1 .. H623 .. 1.92 Ang. 432_ALERT_2_B Short Inter X...Y Contact C3 .. C62 .. 3.03 Ang. 432_ALERT_2_B Short Inter X...Y Contact C64 .. C64 .. 2.95 Ang. 432_ALERT_2_C Short Inter X...Y Contact C3 .. C5 .. 3.13 Ang. Short contacts are expected at high pressure. 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 6.04 su These alerts are due to the relatively low completeness and quality of the data. 128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a The non-standard setting was used for refinement due to the large beta angle which arises in the C2/c setting. 220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.66 Ratio This alert is due to the greater flexibility of the tButyl group compared to the rest of the structure, as such the tButyl group atoms have larger thermal parameters. 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 #------------------------------------------------------------------------------- 14.09 0.500 0.617 896 553 343 15.53 0.550 0.602 1172 705 467 16.99 0.600 0.574 1545 887 658 #----------------------------------------------------------- ACTA Min. Res. ---- 17.76 0.626 0.561 1744 979 765 ; # End of 'script/refcif.dat' # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.0836(3) 0.3421(4) 0.2950(2) 0.0376 1.0000 Uani D . . . . . N2 N 0.1468(3) 0.4270(5) 0.2502(2) 0.0279 1.0000 Uani D . . . . . C3 C 0.1201(4) 0.6106(5) 0.2278(3) 0.0347 1.0000 Uani . . . . . . C4 C 0.1732(4) 0.7308(5) 0.1794(3) 0.0214 1.0000 Uani . . . . . . C5 C 0.2535(4) 0.6529(5) 0.1529(3) 0.0222 1.0000 Uani D . . . . . O5 O 0.2851(3) 0.4540(4) 0.17186(19) 0.0327 1.0000 Uani D . . . . . C6 C 0.3050(4) 0.7692(5) 0.1071(3) 0.0281 1.0000 Uani . . . . . . C61 C 0.3917(4) 0.6849(6) 0.0767(3) 0.0312 1.0000 Uani . . . . . . C62 C 0.4668(4) 0.6147(6) 0.1359(3) 0.0389 1.0000 Uani . . . . . . C63 C 0.3669(5) 0.4996(8) 0.0256(4) 0.0574 1.0000 Uani . . . . . . C64 C 0.4389(5) 0.8546(8) 0.0359(4) 0.0480 1.0000 Uani . . . . . . C7 C 0.2696(4) 0.9713(6) 0.0890(3) 0.0342 1.0000 Uani . . . . . . C8 C 0.1901(4) 1.0509(6) 0.1143(3) 0.0350 1.0000 Uani . . . . . . C9 C 0.1415(4) 0.9322(6) 0.1596(3) 0.0315 1.0000 Uani . . . . . . H1 H 0.111(2) 0.238(7) 0.314(2) 0.0572 1.0000 Uiso D . . . . . H3 H 0.0659 0.6701 0.2428 0.0398 1.0000 Uiso R . . . . . H5 H 0.249(3) 0.397(5) 0.203(3) 0.0500 1.0000 Uiso D . . . . . H621 H 0.5088 0.5224 0.1141 0.0595 1.0000 Uiso R . . . . . H622 H 0.5007 0.7358 0.1564 0.0598 1.0000 Uiso R . . . . . H623 H 0.4389 0.5391 0.1732 0.0597 1.0000 Uiso R . . . . . H631 H 0.4233 0.4372 0.0120 0.0860 1.0000 Uiso R . . . . . H632 H 0.3292 0.5497 -0.0164 0.0856 1.0000 Uiso R . . . . . H633 H 0.3329 0.3954 0.0507 0.0859 1.0000 Uiso R . . . . . H641 H 0.4979 0.8043 0.0220 0.0728 1.0000 Uiso R . . . . . H642 H 0.4496 0.9806 0.0654 0.0731 1.0000 Uiso R . . . . . H643 H 0.3993 0.8895 -0.0066 0.0733 1.0000 Uiso R . . . . . H7 H 0.3018 1.0557 0.0581 0.0398 1.0000 Uiso R . . . . . H8 H 0.1693 1.1867 0.1007 0.0405 1.0000 Uiso R . . . . . H9 H 0.0885 0.9857 0.1781 0.0371 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 0.031(3) 0.0312(16) 0.051(3) 0.0114(13) 0.005(3) -0.0046(13) N2 0.020(4) 0.0289(17) 0.034(3) 0.0013(14) 0.000(3) -0.0060(15) C3 0.038(5) 0.0241(19) 0.039(4) -0.0024(16) -0.013(4) -0.0021(17) C4 0.017(4) 0.0251(19) 0.023(3) -0.0035(15) 0.006(4) -0.0019(17) C5 0.024(5) 0.0216(18) 0.021(3) -0.0009(14) 0.004(4) -0.0042(17) O5 0.035(3) 0.0218(13) 0.042(3) 0.0071(11) 0.008(3) 0.0025(12) C6 0.028(5) 0.0272(19) 0.028(3) -0.0019(16) -0.006(4) -0.0003(19) C61 0.026(4) 0.032(2) 0.035(4) 0.0069(16) -0.001(4) -0.0014(17) C62 0.033(5) 0.038(2) 0.044(4) 0.0067(18) -0.006(4) 0.0011(18) C63 0.046(6) 0.067(3) 0.057(5) -0.025(3) -0.006(5) 0.005(3) C64 0.033(5) 0.059(3) 0.055(5) 0.031(2) 0.016(5) 0.005(2) C7 0.036(5) 0.028(2) 0.036(4) 0.0051(16) -0.007(4) -0.0027(19) C8 0.044(5) 0.0236(19) 0.036(4) 0.0033(16) -0.008(4) 0.001(2) C9 0.028(5) 0.030(2) 0.036(4) -0.0031(17) -0.003(4) 0.0038(19) _refine_ls_extinction_coef 2295.122 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 1.130(17) 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 . 1.400(7) yes O1 . H1 . 0.83(4) no N2 . C3 . 1.283(5) yes C3 . C4 . 1.454(9) yes C3 . H3 . 0.932 no C4 . C5 . 1.389(9) yes C4 . C9 . 1.393(5) yes C5 . O5 . 1.375(4) yes C5 . C6 . 1.395(9) yes O5 . H5 . 0.90(4) no C6 . C61 . 1.516(9) yes C6 . C7 . 1.407(5) yes C61 . C62 . 1.540(5) yes C61 . C63 . 1.535(6) yes C61 . C64 . 1.516(9) yes C62 . H621 . 0.959 no C62 . H622 . 0.969 no C62 . H623 . 0.965 no C63 . H631 . 0.959 no C63 . H632 . 0.968 no C63 . H633 . 0.969 no C64 . H641 . 0.965 no C64 . H642 . 0.975 no C64 . H643 . 0.960 no C7 . C8 . 1.373(10) yes C7 . H7 . 0.941 no C8 . C9 . 1.373(10) yes C8 . H8 . 0.938 no C9 . H9 . 0.931 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 . 105.0(10) no O1 . N2 . C3 . 110.6(6) yes N2 . C3 . C4 . 121.3(6) yes N2 . C3 . H3 . 120.1 no C4 . C3 . H3 . 118.7 no C3 . C4 . C5 . 122.7(4) yes C3 . C4 . C9 . 117.8(6) yes C5 . C4 . C9 . 119.6(6) yes C4 . C5 . O5 . 120.0(5) yes C4 . C5 . C6 . 122.6(4) yes O5 . C5 . C6 . 117.4(6) yes C5 . O5 . H5 . 109.6(10) no C5 . C6 . C61 . 123.2(4) yes C5 . C6 . C7 . 115.2(6) yes C61 . C6 . C7 . 121.5(6) yes C6 . C61 . C62 . 112.3(5) yes C6 . C61 . C63 . 110.6(4) yes C62 . C61 . C63 . 109.6(3) yes C6 . C61 . C64 . 111.3(4) yes C62 . C61 . C64 . 104.4(4) yes C63 . C61 . C64 . 108.5(6) yes C61 . C62 . H621 . 107.4 no C61 . C62 . H622 . 110.5 no H621 . C62 . H622 . 109.7 no C61 . C62 . H623 . 110.6 no H621 . C62 . H623 . 109.2 no H622 . C62 . H623 . 109.4 no C61 . C63 . H631 . 109.0 no C61 . C63 . H632 . 109.7 no H631 . C63 . H632 . 110.2 no C61 . C63 . H633 . 108.5 no H631 . C63 . H633 . 109.1 no H632 . C63 . H633 . 110.3 no C61 . C64 . H641 . 110.4 no C61 . C64 . H642 . 110.4 no H641 . C64 . H642 . 109.1 no C61 . C64 . H643 . 108.7 no H641 . C64 . H643 . 108.7 no H642 . C64 . H643 . 109.4 no C6 . C7 . C8 . 123.1(6) yes C6 . C7 . H7 . 118.5 no C8 . C7 . H7 . 118.5 no C7 . C8 . C9 . 120.0(4) yes C7 . C8 . H8 . 119.9 no C9 . C8 . H8 . 120.0 no C4 . C9 . C8 . 119.5(6) yes C4 . C9 . H9 . 119.6 no C8 . C9 . H9 . 120.9 no _chemical_name_common 3-tButylsalicylaldoxime #END data_tBu46kbar _database_code_depnum_ccdc_archive 'CCDC 657073' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of hexane/chloroform solution' _audit_creation_date 06-12-18 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-tButylsalicylaldoxime _chemical_melting_point ? _cell_length_a 14.271(4) _cell_length_b 6.3030(9) _cell_length_c 18.459(5) _cell_angle_alpha 90 _cell_angle_beta 95.590(15) _cell_angle_gamma 90 _cell_volume 1652.5(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' 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 -x+1/2,y,-z x+1/2,-y,z -x+1,y+1/2,-z+1/2 x+1,-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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C11 H15 N1 O2 # Dc = 1.55 Fooo = 832.00 Mu = 1.07 M = 193.25 # Found Formula = C11 H15 N1 O2 # Dc = 1.55 FOOO = 832.00 Mu = 1.07 M = 193.25 _chemical_formula_sum 'C11 H15 N1 O2' _chemical_formula_moiety 'C11 H15 N1 O2' _chemical_formula_weight 193.25 _cell_measurement_reflns_used 1338 _cell_measurement_theta_min 2 _cell_measurement_theta_max 15 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.107 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.05 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48690 _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 'Model taken from 10kbar structure' _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_ambient_pressure 4600000 _diffrn_reflns_number 7728 _reflns_number_total 920 _diffrn_reflns_av_R_equivalents 0.119 # Number of reflections with Friedels Law is 967 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1704 _diffrn_reflns_theta_min 2.340 _diffrn_reflns_theta_max 17.769 _diffrn_measured_fraction_theta_max 0.540 _diffrn_reflns_theta_full 13.505 _diffrn_measured_fraction_theta_full 0.599 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -11 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _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 -0.27 _refine_diff_density_max 0.24 _refine_ls_number_reflns 918 _refine_ls_number_restraints 4 _refine_ls_number_parameters 134 #_refine_ls_R_factor_ref 0.1084 _refine_ls_wR_factor_ref 0.2390 _refine_ls_goodness_of_fit_ref 0.9765 #_reflns_number_all 918 _refine_ls_R_factor_all 0.1084 _refine_ls_wR_factor_all 0.2390 # 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 569 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_gt 0.1829 _refine_ls_shift/su_max 0.000056 # 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: 132. 213. 130. 52.1 12.7 ; _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. These hydroxy hydrogen positions were then refined subject to O-H distance restraints of 0.84(5) Angstroms and X-O-H angle restraints of 105(1) degrees for H1 and 110(1) degrees for H5. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Checkcif Output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.57 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.51 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.60 088_ALERT_3_B Poor Data / Parameter Ratio .................... 6.85 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 415_ALERT_2_A Short Inter D-H..H-X H1 .. H623 .. 1.76 Ang. 432_ALERT_2_A Short Inter X...Y Contact C64 .. C64 .. 2.87 Ang. 413_ALERT_2_B Short Inter XH3 .. XHn H631 .. H641 .. 1.96 Ang. 432_ALERT_2_B Short Inter X...Y Contact C3 .. C62 .. 2.99 Ang. 432_ALERT_2_B Short Inter X...Y Contact C3 .. C5 .. 3.08 Ang. 432_ALERT_2_C Short Inter X...Y Contact O5 .. C8 .. 2.99 Ang. Short contacts are expected at high pressure. 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 These alerts are due to the relatively low completeness and quality of the data. 128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a The non-standard setting was used for refinement due to the large beta angle which arises in the C2/c setting. 220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio This alert is due to the greater flexibility of the tButyl group compared to the rest of the structure, as such the tButyl group atoms have larger thermal parameters. 732_ALERT_1_C Angle Calc 105(3), Rep 105.0(10) ...... 3.00 su-Ra N2 -O1 -H1 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 110(3), Rep 109.8(10) ...... 3.00 su-Ra C5 -O5 -H5 1.555 1.555 1.555 These alerts are due to the fact that PLATON calculates esds using only the variances whereas CRYSTALS uses the full variance/covariance matrix. In this case restraints have been applied to the angles and this affects the esds. 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 #------------------------------------------------------------------------------- 14.09 0.500 0.591 876 518 358 15.53 0.550 0.577 1143 659 484 16.99 0.600 0.558 1497 836 661 #----------------------------------------------------------- ACTA Min. Res. ---- 17.77 0.627 0.540 1704 920 784 ; # End of 'script/refcif.dat' # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.0828(4) 0.3416(5) 0.2978(3) 0.0277 1.0000 Uani D . . . . . N2 N 0.1475(4) 0.4267(6) 0.2506(3) 0.0212 1.0000 Uani D . . . . . C3 C 0.1211(5) 0.6102(6) 0.2283(3) 0.0291 1.0000 Uani . . . . . . C4 C 0.1714(5) 0.7304(7) 0.1808(4) 0.0187 1.0000 Uani . . . . . . C5 C 0.2523(5) 0.6549(7) 0.1529(4) 0.0182 1.0000 Uani D . . . . . O5 O 0.2842(3) 0.4533(5) 0.1717(2) 0.0290 1.0000 Uani D . . . . . C6 C 0.3061(5) 0.7705(7) 0.1056(4) 0.0298 1.0000 Uani . . . . . . C61 C 0.3914(5) 0.6840(7) 0.0768(4) 0.0343 1.0000 Uani . . . . . . C62 C 0.4672(5) 0.6106(7) 0.1363(4) 0.0337 1.0000 Uani . . . . . . C63 C 0.3670(6) 0.4998(10) 0.0238(4) 0.0489 1.0000 Uani . . . . . . C64 C 0.4418(7) 0.8544(9) 0.0353(5) 0.0542 1.0000 Uani . . . . . . C7 C 0.2688(5) 0.9727(7) 0.0888(4) 0.0317 1.0000 Uani . . . . . . C8 C 0.1905(5) 1.0548(6) 0.1137(4) 0.0288 1.0000 Uani . . . . . . C9 C 0.1410(5) 0.9348(7) 0.1601(3) 0.0263 1.0000 Uani . . . . . . H1 H 0.107(3) 0.221(7) 0.312(3) 0.0422 1.0000 Uiso D . . . . . H3 H 0.0660 0.6669 0.2442 0.0338 1.0000 Uiso R . . . . . H5 H 0.253(4) 0.403(5) 0.205(3) 0.0431 1.0000 Uiso D . . . . . H621 H 0.5108 0.5207 0.1150 0.0500 1.0000 Uiso R . . . . . H622 H 0.5014 0.7306 0.1580 0.0503 1.0000 Uiso R . . . . . H623 H 0.4392 0.5328 0.1736 0.0502 1.0000 Uiso R . . . . . H631 H 0.4238 0.4411 0.0081 0.0720 1.0000 Uiso R . . . . . H632 H 0.3271 0.5496 -0.0180 0.0719 1.0000 Uiso R . . . . . H633 H 0.3346 0.3915 0.0480 0.0721 1.0000 Uiso R . . . . . H641 H 0.4985 0.7976 0.0189 0.0800 1.0000 Uiso R . . . . . H642 H 0.4577 0.9743 0.0670 0.0799 1.0000 Uiso R . . . . . H643 H 0.4006 0.8989 -0.0061 0.0800 1.0000 Uiso R . . . . . H7 H 0.3008 1.0566 0.0576 0.0369 1.0000 Uiso R . . . . . H8 H 0.1690 1.1889 0.0995 0.0342 1.0000 Uiso R . . . . . H9 H 0.0871 0.9890 0.1777 0.0308 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 0.020(4) 0.036(2) 0.029(4) 0.0084(16) 0.015(4) -0.0010(16) N2 0.015(5) 0.033(2) 0.017(4) 0.0020(17) 0.007(5) -0.0064(18) C3 0.031(6) 0.026(2) 0.029(5) -0.006(2) -0.006(5) 0.000(2) C4 0.011(6) 0.026(2) 0.021(5) -0.0018(19) 0.006(5) 0.000(2) C5 0.017(6) 0.026(2) 0.013(5) 0.0011(18) 0.008(6) -0.001(2) O5 0.032(4) 0.0233(17) 0.033(4) 0.0082(13) 0.012(4) 0.0051(15) C6 0.034(6) 0.024(2) 0.028(5) 0.006(2) -0.010(6) -0.005(2) C61 0.035(7) 0.028(2) 0.038(5) 0.009(2) -0.010(6) -0.001(2) C62 0.024(6) 0.038(3) 0.038(5) 0.006(2) -0.004(5) 0.000(2) C63 0.042(8) 0.067(4) 0.036(6) -0.026(3) -0.003(7) 0.011(3) C64 0.041(7) 0.056(4) 0.064(7) 0.030(3) -0.003(7) 0.004(3) C7 0.042(6) 0.023(2) 0.027(5) 0.0097(19) -0.008(5) -0.001(2) C8 0.037(6) 0.022(2) 0.026(5) 0.009(2) -0.003(5) 0.002(2) C9 0.023(6) 0.029(2) 0.026(5) -0.0025(19) -0.002(5) 0.007(2) _refine_ls_extinction_coef 1000(200) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.661(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 . 1.432(9) yes O1 . H1 . 0.86(4) no N2 . C3 . 1.272(6) yes C3 . C4 . 1.407(12) yes C3 . H3 . 0.936 no C4 . C5 . 1.394(12) yes C4 . C9 . 1.401(6) yes C5 . O5 . 1.383(5) yes C5 . C6 . 1.418(12) yes O5 . H5 . 0.85(4) no C6 . C61 . 1.479(13) yes C6 . C7 . 1.405(6) yes C61 . C62 . 1.536(6) yes C61 . C63 . 1.536(7) yes C61 . C64 . 1.538(12) yes C62 . H621 . 0.954 no C62 . H622 . 0.966 no C62 . H623 . 0.964 no C63 . H631 . 0.961 no C63 . H632 . 0.965 no C63 . H633 . 0.959 no C64 . H641 . 0.960 no C64 . H642 . 0.969 no C64 . H643 . 0.960 no C7 . C8 . 1.350(13) yes C7 . H7 . 0.934 no C8 . C9 . 1.388(12) yes C8 . H8 . 0.928 no C9 . H9 . 0.928 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 . 105.0(10) no O1 . N2 . C3 . 110.4(7) yes N2 . C3 . C4 . 122.6(8) yes N2 . C3 . H3 . 118.5 no C4 . C3 . H3 . 119.0 no C3 . C4 . C5 . 122.5(5) yes C3 . C4 . C9 . 120.1(8) yes C5 . C4 . C9 . 117.3(8) yes C4 . C5 . O5 . 119.0(7) yes C4 . C5 . C6 . 124.7(5) yes O5 . C5 . C6 . 116.2(8) yes C5 . O5 . H5 . 109.8(10) no C5 . C6 . C61 . 123.1(5) yes C5 . C6 . C7 . 112.7(8) yes C61 . C6 . C7 . 124.3(7) yes C6 . C61 . C62 . 113.6(7) yes C6 . C61 . C63 . 111.3(5) yes C62 . C61 . C63 . 109.1(4) yes C6 . C61 . C64 . 111.3(5) yes C62 . C61 . C64 . 103.6(5) yes C63 . C61 . C64 . 107.4(8) yes C61 . C62 . H621 . 109.1 no C61 . C62 . H622 . 110.7 no H621 . C62 . H622 . 108.2 no C61 . C62 . H623 . 110.6 no H621 . C62 . H623 . 108.9 no H622 . C62 . H623 . 109.3 no C61 . C63 . H631 . 109.8 no C61 . C63 . H632 . 110.0 no H631 . C63 . H632 . 109.5 no C61 . C63 . H633 . 109.4 no H631 . C63 . H633 . 109.0 no H632 . C63 . H633 . 109.2 no C61 . C64 . H641 . 110.2 no C61 . C64 . H642 . 109.6 no H641 . C64 . H642 . 109.1 no C61 . C64 . H643 . 108.6 no H641 . C64 . H643 . 109.3 no H642 . C64 . H643 . 110.0 no C6 . C7 . C8 . 125.5(8) yes C6 . C7 . H7 . 116.9 no C8 . C7 . H7 . 117.6 no C7 . C8 . C9 . 119.3(5) yes C7 . C8 . H8 . 121.0 no C9 . C8 . H8 . 119.7 no C4 . C9 . C8 . 120.4(8) yes C4 . C9 . H9 . 119.2 no C8 . C9 . H9 . 120.4 no _chemical_name_common 3-tButylsalicylaldoxime #END data_tBu62kbar _database_code_depnum_ccdc_archive 'CCDC 657074' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of hexane/chloroform solution' _audit_creation_date 06-12-18 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-tButylsalicylaldoxime _chemical_melting_point ? _cell_length_a 14.101(3) _cell_length_b 6.2699(6) _cell_length_c 18.158(3) _cell_angle_alpha 90 _cell_angle_beta 95.817(10) _cell_angle_gamma 90 _cell_volume 1597.1(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' 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 -x+1/2,y,-z x+1/2,-y,z -x+1,y+1/2,-z+1/2 x+1,-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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C11 H15 N1 O2 # Dc = 1.61 Fooo = 832.00 Mu = 1.10 M = 193.25 # Found Formula = C11 H15 N1 O2 # Dc = 1.61 FOOO = 832.00 Mu = 1.10 M = 193.25 _chemical_formula_sum 'C11 H15 N1 O2' _chemical_formula_moiety 'C11 H15 N1 O2' _chemical_formula_weight 193.25 _cell_measurement_reflns_used 1320 _cell_measurement_theta_min 2 _cell_measurement_theta_max 15 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.110 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.29 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48690 _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 'Model taken from 10kbar structure' _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_ambient_pressure 6200000 _diffrn_reflns_number 7429 _reflns_number_total 791 _diffrn_reflns_av_R_equivalents 0.110 # Number of reflections with Friedels Law is 838 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1638 _diffrn_reflns_theta_min 2.356 _diffrn_reflns_theta_max 17.735 _diffrn_measured_fraction_theta_max 0.483 _diffrn_reflns_theta_full 13.656 _diffrn_measured_fraction_theta_full 0.539 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -8 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _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 0.16 _refine_ls_number_reflns 790 _refine_ls_number_restraints 38 _refine_ls_number_parameters 134 #_refine_ls_R_factor_ref 0.0896 _refine_ls_wR_factor_ref 0.1634 _refine_ls_goodness_of_fit_ref 0.9538 #_reflns_number_all 790 _refine_ls_R_factor_all 0.0896 _refine_ls_wR_factor_all 0.1634 # 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 510 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_gt 0.1303 _refine_ls_shift/su_max 0.000072 # 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: 74.7 111. 63.4 21.4 5.21 ; _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. These hydroxy hydrogen positions were then refined subject to O-H distance restraints of 0.84(5) Angstroms and X-O-H angle restraints of 105(1) degrees for H1 and 110(1) degrees for H5. All the remaining hydrogens were refined subject to geometric restraints and then constrained to ride on their host atoms. Global vibration restraints were also applied due to the decreasing quality and completeness of the data. Checkcif Output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.51 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.66 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.54 088_ALERT_3_A Poor Data / Parameter Ratio .................... 5.90 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 432_ALERT_2_A Short Inter X...Y Contact C64 .. C64 .. 2.83 Ang. 413_ALERT_2_B Short Inter XH3 .. XHn H7 .. H633 .. 2.09 Ang. 413_ALERT_2_B Short Inter XH3 .. XHn H631 .. H641 .. 1.96 Ang. 415_ALERT_2_B Short Inter D-H..H-X H1 .. H623 .. 1.95 Ang. 432_ALERT_2_B Short Inter X...Y Contact C3 .. C62 .. 2.92 Ang. 432_ALERT_2_B Short Inter X...Y Contact C3 .. C5 .. 3.02 Ang. 413_ALERT_2_C Short Inter XH3 .. XHn H9 .. H622 .. 2.14 Ang. 432_ALERT_2_C Short Inter X...Y Contact O1 .. C7 .. 2.99 Ang. 432_ALERT_2_C Short Inter X...Y Contact O5 .. C8 .. 2.95 Ang. 432_ALERT_2_C Short Inter X...Y Contact C3 .. C6 .. 3.14 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C4 .. 3.18 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.19 Ang. 432_ALERT_2_C Short Inter X...Y Contact C7 .. C7 .. 3.18 Ang. Short contacts are expected at high pressure. 152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? This appears to be due to a simple rounding error. 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 These alerts are due to the relatively low completeness and quality of the data. 128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a The non-standard setting was used for refinement due to the large beta angle which arises in the C2/c setting. 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 #------------------------------------------------------------------------------- 14.09 0.500 0.533 838 447 391 15.53 0.550 0.515 1110 572 538 16.99 0.600 0.498 1450 722 728 #----------------------------------------------------------- ACTA Min. Res. ---- 17.73 0.626 0.484 1635 791 844 ; 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 0.0827(4) 0.3413(5) 0.2997(2) 0.0324 1.0000 Uani D U . . . . N2 N 0.1462(5) 0.4255(5) 0.2526(3) 0.0249 1.0000 Uani D U . . . . C3 C 0.1194(5) 0.6127(6) 0.2300(3) 0.0224 1.0000 Uani . U . . . . C4 C 0.1731(5) 0.7320(6) 0.1798(3) 0.0208 1.0000 Uani . U . . . . C5 C 0.2536(5) 0.6526(6) 0.1529(3) 0.0205 1.0000 Uani D U . . . . O5 O 0.2828(4) 0.4517(4) 0.1719(2) 0.0302 1.0000 Uani D U . . . . C6 C 0.3066(6) 0.7705(6) 0.1058(3) 0.0216 1.0000 Uani . U . . . . C61 C 0.3923(6) 0.6823(6) 0.0755(3) 0.0270 1.0000 Uani . U . . . . C62 C 0.4692(5) 0.6053(7) 0.1358(3) 0.0324 1.0000 Uani . U . . . . C63 C 0.3639(6) 0.4994(8) 0.0233(3) 0.0376 1.0000 Uani . U . . . . C64 C 0.4421(7) 0.8546(8) 0.0350(4) 0.0401 1.0000 Uani . U . . . . C7 C 0.2700(6) 0.9775(6) 0.0878(3) 0.0225 1.0000 Uani . U . . . . C8 C 0.1880(5) 1.0567(6) 0.1146(3) 0.0237 1.0000 Uani . U . . . . C9 C 0.1411(5) 0.9368(6) 0.1602(3) 0.0224 1.0000 Uani . U . . . . H1 H 0.113(2) 0.242(7) 0.323(2) 0.0494 1.0000 Uiso D . . . . . H3 H 0.0641 0.6741 0.2463 0.0264 1.0000 Uiso R . . . . . H5 H 0.247(3) 0.398(5) 0.204(3) 0.0451 1.0000 Uiso D . . . . . H621 H 0.5082 0.4971 0.1167 0.0480 1.0000 Uiso R . . . . . H622 H 0.5094 0.7252 0.1540 0.0480 1.0000 Uiso R . . . . . H623 H 0.4391 0.5462 0.1772 0.0481 1.0000 Uiso R . . . . . H631 H 0.4212 0.4406 0.0069 0.0564 1.0000 Uiso R . . . . . H632 H 0.3230 0.5513 -0.0189 0.0557 1.0000 Uiso R . . . . . H633 H 0.3309 0.3899 0.0485 0.0558 1.0000 Uiso R . . . . . H641 H 0.5010 0.8017 0.0199 0.0610 1.0000 Uiso R . . . . . H642 H 0.4533 0.9788 0.0661 0.0609 1.0000 Uiso R . . . . . H643 H 0.4018 0.8930 -0.0089 0.0607 1.0000 Uiso R . . . . . H7 H 0.3016 1.0641 0.0561 0.0270 1.0000 Uiso R . . . . . H8 H 0.1665 1.1945 0.1001 0.0281 1.0000 Uiso R . . . . . H9 H 0.0870 0.9860 0.1785 0.0261 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 0.038(5) 0.0251(16) 0.034(3) 0.0068(14) 0.002(3) -0.0024(18) N2 0.030(5) 0.0207(15) 0.023(2) -0.0015(15) -0.002(3) -0.002(2) C3 0.024(4) 0.0203(16) 0.022(2) -0.0047(14) 0.001(2) 0.0003(19) C4 0.019(4) 0.0193(16) 0.022(2) -0.0030(13) -0.005(2) -0.0040(16) C5 0.029(4) 0.0144(15) 0.018(2) -0.0016(13) -0.002(2) 0.0031(17) O5 0.040(5) 0.0152(13) 0.035(3) 0.0035(12) 0.001(3) 0.0057(15) C6 0.024(4) 0.0204(16) 0.019(3) 0.0009(13) -0.005(2) -0.0005(16) C61 0.032(4) 0.0265(19) 0.022(3) 0.0052(15) 0.001(2) 0.0060(19) C62 0.035(6) 0.033(2) 0.028(3) 0.0056(18) -0.003(4) 0.003(2) C63 0.025(8) 0.052(3) 0.035(4) -0.016(2) 0.002(5) 0.007(3) C64 0.038(5) 0.045(2) 0.039(4) 0.019(2) 0.011(3) 0.009(3) C7 0.027(5) 0.0207(17) 0.019(3) 0.0043(15) 0.001(3) 0.0003(19) C8 0.022(5) 0.0190(19) 0.028(3) -0.0013(14) -0.006(3) 0.0030(18) C9 0.020(4) 0.0232(17) 0.023(3) -0.0045(15) -0.002(3) 0.0050(19) _refine_ls_extinction_coef 640(110) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.701(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 O1 . N2 . 1.403(9) yes O1 . H1 . 0.84(4) no N2 . C3 . 1.288(5) yes C3 . C4 . 1.450(11) yes C3 . H3 . 0.943 no C4 . C5 . 1.373(12) yes C4 . C9 . 1.395(6) yes C5 . O5 . 1.358(4) yes C5 . C6 . 1.402(12) yes O5 . H5 . 0.88(4) no C6 . C61 . 1.484(13) yes C6 . C7 . 1.422(6) yes C61 . C62 . 1.538(6) yes C61 . C63 . 1.516(6) yes C61 . C64 . 1.520(11) yes C62 . H621 . 0.961 no C62 . H622 . 0.979 no C62 . H623 . 0.973 no C63 . H631 . 0.962 no C63 . H632 . 0.968 no C63 . H633 . 0.969 no C64 . H641 . 0.959 no C64 . H642 . 0.966 no C64 . H643 . 0.961 no C7 . C8 . 1.392(12) yes C7 . H7 . 0.936 no C8 . C9 . 1.341(11) yes C8 . H8 . 0.944 no C9 . H9 . 0.917 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 . 104.7(10) no O1 . N2 . C3 . 110.7(7) yes N2 . C3 . C4 . 121.0(7) yes N2 . C3 . H3 . 119.8 no C4 . C3 . H3 . 119.2 no C3 . C4 . C5 . 122.6(4) yes C3 . C4 . C9 . 117.3(7) yes C5 . C4 . C9 . 120.1(7) yes C4 . C5 . O5 . 119.1(7) yes C4 . C5 . C6 . 122.4(4) yes O5 . C5 . C6 . 118.5(7) yes C5 . O5 . H5 . 110.1(10) no C5 . C6 . C61 . 122.2(4) yes C5 . C6 . C7 . 114.8(8) yes C61 . C6 . C7 . 123.0(7) yes C6 . C61 . C62 . 113.3(6) yes C6 . C61 . C63 . 109.9(6) yes C62 . C61 . C63 . 109.3(4) yes C6 . C61 . C64 . 110.4(5) yes C62 . C61 . C64 . 103.9(6) yes C63 . C61 . C64 . 109.9(6) yes C61 . C62 . H621 . 110.6 no C61 . C62 . H622 . 110.0 no H621 . C62 . H622 . 109.4 no C61 . C62 . H623 . 109.8 no H621 . C62 . H623 . 108.7 no H622 . C62 . H623 . 108.3 no C61 . C63 . H631 . 107.9 no C61 . C63 . H632 . 109.9 no H631 . C63 . H632 . 109.6 no C61 . C63 . H633 . 110.5 no H631 . C63 . H633 . 109.4 no H632 . C63 . H633 . 109.6 no C61 . C64 . H641 . 110.4 no C61 . C64 . H642 . 110.2 no H641 . C64 . H642 . 110.5 no C61 . C64 . H643 . 108.4 no H641 . C64 . H643 . 107.9 no H642 . C64 . H643 . 109.4 no C6 . C7 . C8 . 122.7(8) yes C6 . C7 . H7 . 119.1 no C8 . C7 . H7 . 118.2 no C7 . C8 . C9 . 119.7(5) yes C7 . C8 . H8 . 118.9 no C9 . C8 . H8 . 121.5 no C4 . C9 . C8 . 120.5(8) yes C4 . C9 . H9 . 118.5 no C8 . C9 . H9 . 121.0 no #END _chemical_name_common 3-tButylsalicylaldoxime #END data_Cl16kbar _database_code_depnum_ccdc_archive 'CCDC 657075' _exptl_crystal_recrystallization_method 'Recrystallisation by pressure from methanol/ethanol solution' _audit_creation_date 06-07-19 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-chlorosalicylaldoxime _chemical_melting_point ? _cell_length_a 12.843(3) _cell_length_b 3.6613(3) _cell_length_c 13.7921(16) _cell_angle_alpha 90 _cell_angle_beta 92.603(13) _cell_angle_gamma 90 _cell_volume 647.88(16) _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 = C6 H6 Cl1 N1 O2 # Dc = 1.64 Fooo = 352.00 Mu = 5.16 M = 159.57 # Found Formula = C7 H6 Cl1 N1 O2 # Dc = 1.76 FOOO = 352.00 Mu = 5.23 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 1569 _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 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.18 _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.523 # Sheldrick geometric approximatio 0.92 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2006/1' _exptl_absorpt_correction_T_min 0.43 _exptl_absorpt_correction_T_max 0.95 _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_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'Model taken from ambient pressure structure' _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_ambient_pressure 1600000 _diffrn_reflns_number 3158 _reflns_number_total 440 _diffrn_reflns_av_R_equivalents 0.064 # Number of reflections with Friedels Law is 470 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1313 _diffrn_reflns_theta_min 2.957 _diffrn_reflns_theta_max 26.288 _diffrn_measured_fraction_theta_max 0.333 _diffrn_reflns_theta_full 25.237 _diffrn_measured_fraction_theta_full 0.357 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -4 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 4 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _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 -0.22 _refine_diff_density_max 0.26 _refine_ls_number_reflns 440 _refine_ls_number_restraints 120 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.0746 _refine_ls_wR_factor_ref 0.1577 _refine_ls_goodness_of_fit_ref 1.0232 #_reflns_number_all 440 _refine_ls_R_factor_all 0.0746 _refine_ls_wR_factor_all 0.1577 # 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 348 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_gt 0.1476 _refine_ls_shift/su_max 0.000218 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 1.62P] ,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(5) Angstroms and X-O-H angle restraints of 105(1) degrees. The remaining hydrogens which were placed geometrically were then constrained to ride on their host atom. The primary geometry (bond lengths and angles) has been restrained to agree with the ambient structure with loose esds on the restraints. Global vibration and thermal similarity restraints were also applied. Checkcif output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.36 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.36 088_ALERT_3_A Poor Data / Parameter Ratio .................... 4.15 340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 15 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 061_ALERT_3_A Tmax/Tmin Range Test RR' too Large ............. 0.47 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. 732_ALERT_1_B Angle Calc 105(4), Rep 105.0(9) ...... 4.44 su-Rat N2 -O1 -H1 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 105(3), Rep 105.0(9) ...... 3.33 su-Rat C5 -O5 -H5 1.555 1.555 1.555 These alerts are due to the fact that PLATON calculates esds using only the variances whereas CRYSTALS uses the full variance/covariance matrix. 152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? This discrepancy is probably simply due to a small rounding error. 432_ALERT_2_C Short Inter X...Y Contact O1 .. C3 .. 2.95 Ang. Noted but no action taken. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.421 679 286 393 23.01 0.550 0.376 897 337 560 25.24 0.600 0.357 1183 422 761 #----------------------------------------------------------- ACTA Min. Res. ---- 26.29 0.623 0.334 1319 440 879 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O -0.0671(8) -0.4508(13) 0.8552(4) 0.0458 1.0000 Uani D U . . . . N2 N 0.0284(11) -0.2956(16) 0.8882(5) 0.0382 1.0000 Uani D U . . . . C3 C 0.1007(12) -0.3392(19) 0.8307(6) 0.0352 1.0000 Uani D U . . . . C4 C 0.2028(9) -0.1912(15) 0.8537(5) 0.0334 1.0000 Uani D U . . . . C5 C 0.2264(9) -0.0234(15) 0.9436(5) 0.0301 1.0000 Uani D U . . . . O5 O 0.1555(9) 0.0088(12) 1.0119(4) 0.0394 1.0000 Uani D U . . . . C6 C 0.3256(8) 0.1104(16) 0.9632(5) 0.0302 1.0000 Uani D U . . . . Cl6 Cl 0.3521(3) 0.3046(4) 1.07660(13) 0.0384 1.0000 Uani D U . . . . C7 C 0.4010(10) 0.0856(17) 0.8980(6) 0.0350 1.0000 Uani D U . . . . C8 C 0.3770(10) -0.0809(17) 0.8073(5) 0.0405 1.0000 Uani D U . . . . C9 C 0.2800(12) -0.2144(16) 0.7870(5) 0.0372 1.0000 Uani D U . . . . H1 H -0.111(3) -0.38(2) 0.895(5) 0.0678 1.0000 Uiso D . . . . . H3 H 0.0883 -0.4662 0.7726 0.0408 1.0000 Uiso R . . . . . H5 H 0.103(4) -0.11(2) 0.990(3) 0.0590 1.0000 Uiso D . . . . . H7 H 0.4680 0.1767 0.9135 0.0418 1.0000 Uiso R . . . . . H8 H 0.4277 -0.1007 0.7622 0.0480 1.0000 Uiso R . . . . . H9 H 0.2647 -0.3262 0.7270 0.0440 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 0.052(12) 0.046(3) 0.039(3) -0.009(2) -0.008(5) -0.012(4) N2 0.043(13) 0.034(3) 0.036(5) 0.000(3) -0.011(6) -0.001(5) C3 0.050(13) 0.029(3) 0.026(5) 0.002(3) -0.011(5) -0.003(6) C4 0.050(13) 0.023(2) 0.027(3) 0.002(3) -0.002(5) -0.006(5) C5 0.036(11) 0.030(3) 0.024(3) 0.005(3) -0.006(5) 0.001(5) O5 0.039(12) 0.047(3) 0.031(3) -0.005(2) 0.000(5) -0.012(4) C6 0.035(11) 0.030(3) 0.025(3) 0.006(3) -0.006(4) 0.003(5) Cl6 0.046(7) 0.0352(8) 0.0326(12) -0.0025(6) -0.009(2) -0.0014(12) C7 0.037(12) 0.033(3) 0.034(3) 0.008(3) 0.000(4) 0.002(5) C8 0.051(13) 0.040(3) 0.030(3) 0.007(3) 0.006(5) 0.000(5) C9 0.057(13) 0.028(3) 0.027(4) 0.004(3) 0.002(5) -0.002(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.33(17) 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 . 1.407(14) yes O1 . H1 . 0.85(4) no N2 . C3 . 1.259(19) yes C3 . C4 . 1.440(15) yes C3 . H3 . 0.933 no C4 . C5 . 1.405(8) yes C4 . C9 . 1.385(15) yes C5 . O5 . 1.343(12) yes C5 . C6 . 1.381(12) yes O5 . H5 . 0.85(4) no C6 . Cl6 . 1.737(6) yes C6 . C7 . 1.354(13) yes C7 . C8 . 1.413(9) yes C7 . H7 . 0.939 no C8 . C9 . 1.355(15) yes C8 . H8 . 0.924 no C9 . H9 . 0.936 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 . 105.0(9) no O1 . N2 . C3 . 113.7(5) yes N2 . C3 . C4 . 120.2(5) yes N2 . C3 . H3 . 120.1 no C4 . C3 . H3 . 119.7 no C3 . C4 . C5 . 121.1(5) yes C3 . C4 . C9 . 120.2(5) yes C5 . C4 . C9 . 118.7(5) yes C4 . C5 . O5 . 122.1(5) yes C4 . C5 . C6 . 119.2(5) yes O5 . C5 . C6 . 118.7(4) yes C5 . O5 . H5 . 105.0(9) no C5 . C6 . Cl6 . 117.6(5) yes C5 . C6 . C7 . 121.8(4) yes Cl6 . C6 . C7 . 120.6(5) yes C6 . C7 . C8 . 118.9(6) yes C6 . C7 . H7 . 120.1 no C8 . C7 . H7 . 121.0 no C7 . C8 . C9 . 120.0(6) yes C7 . C8 . H8 . 119.8 no C9 . C8 . H8 . 120.2 no C4 . C9 . C8 . 121.3(5) yes C4 . C9 . H9 . 119.0 no C8 . C9 . H9 . 119.6 no _chemical_name_common 3-chlorosalicylaldoxime #END data_Cl24kbar _database_code_depnum_ccdc_archive 'CCDC 657076' _exptl_crystal_recrystallization_method 'Recrystallisation by pressure from methanol/ethanol solution' _audit_creation_date 06-07-19 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-chlorosalicylaldoxime _chemical_melting_point ? _cell_length_a 12.748(2) _cell_length_b 3.5954(3) _cell_length_c 13.6496(15) _cell_angle_alpha 90 _cell_angle_beta 93.115(13) _cell_angle_gamma 90 _cell_volume 624.71(15) _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 = C6 H6 Cl1 N1 O2 # Dc = 1.70 Fooo = 352.00 Mu = 5.35 M = 159.57 # Found Formula = C7 H6 Cl1 N1 O2 # Dc = 1.82 FOOO = 352.00 Mu = 5.42 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 1536 _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 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.18 _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.542 # Sheldrick geometric approximatio 0.92 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2006/1' _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.95 _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_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'Model taken from ambient pressure structure' _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_ambient_pressure 2400000 _diffrn_reflns_number 3218 _reflns_number_total 415 _diffrn_reflns_av_R_equivalents 0.060 # Number of reflections with Friedels Law is 446 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1283 _diffrn_reflns_theta_min 2.989 _diffrn_reflns_theta_max 26.415 _diffrn_measured_fraction_theta_max 0.320 _diffrn_reflns_theta_full 25.094 _diffrn_measured_fraction_theta_full 0.354 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -4 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 4 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _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 -0.22 _refine_diff_density_max 0.25 _refine_ls_number_reflns 415 _refine_ls_number_restraints 120 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.0592 _refine_ls_wR_factor_ref 0.1213 _refine_ls_goodness_of_fit_ref 1.0280 #_reflns_number_all 415 _refine_ls_R_factor_all 0.0592 _refine_ls_wR_factor_all 0.1213 # 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 341 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_gt 0.1141 _refine_ls_shift/su_max 0.000472 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.75P] ,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(5) Angstroms and X-O-H angle restraints of 105(1) degrees. The remaining hydrogens which were placed geometrically were then constrained to ride on their host atom. The primary geometry (bond lengths and angles) has been restrained to agree with the ambient structure with loose esds on the restraints. Global vibration and thermal similarity restraints were also applied. Checkcif output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.34 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.35 088_ALERT_3_A Poor Data / Parameter Ratio .................... 3.92 340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 12 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.52 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. 432_ALERT_2_B Short Inter X...Y Contact O1 .. C3 .. 2.89 Ang. Noted but no action taken. 152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? This discrepancy is probably simply due to a small rounding error. 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08 This is probably due to the lack of information in one direction which occurs as a result of the Merrill-Bassett diamond-anvil cell shading a significant region of reciprocal space. The effect of this shading is often to cause a smearing out of electron density in one particular direction. 732_ALERT_1_C Angle Calc 105(3), Rep 105.0(9) ...... 3.33 su-Rat N2 -O1 -H1 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 105(2), Rep 105.0(9) ...... 2.22 su-Rat C5 -O5 -H5 1.555 1.555 1.555 These alerts are due to the fact that PLATON calculates esds using only the variances whereas CRYSTALS uses the full variance/covariance matrix. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.415 660 274 386 23.01 0.550 0.365 862 315 547 25.24 0.600 0.354 1136 402 734 #----------------------------------------------------------- ACTA Min. Res. ---- 26.41 0.626 0.321 1293 415 878 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O -0.0681(7) -0.4622(10) 0.8551(3) 0.0407 1.0000 Uani D U . . . . N2 N 0.0270(10) -0.3016(12) 0.8891(4) 0.0343 1.0000 Uani D U . . . . C3 C 0.0999(11) -0.3451(14) 0.8302(4) 0.0307 1.0000 Uani D U . . . . C4 C 0.2024(8) -0.1947(11) 0.8531(4) 0.0303 1.0000 Uani D U . . . . C5 C 0.2273(8) -0.0233(12) 0.9452(4) 0.0286 1.0000 Uani D U . . . . O5 O 0.1555(7) 0.0098(10) 1.0132(3) 0.0399 1.0000 Uani D U . . . . C6 C 0.3258(7) 0.1111(12) 0.9648(4) 0.0307 1.0000 Uani D U . . . . Cl6 Cl 0.3538(3) 0.3086(3) 1.07917(9) 0.0386 1.0000 Uani D U . . . . C7 C 0.4016(8) 0.0828(13) 0.8993(4) 0.0328 1.0000 Uani D U . . . . C8 C 0.3772(8) -0.0849(12) 0.8077(4) 0.0321 1.0000 Uani D U . . . . C9 C 0.2788(10) -0.2175(12) 0.7865(4) 0.0319 1.0000 Uani D U . . . . H1 H -0.115(2) -0.358(16) 0.890(4) 0.0599 1.0000 Uiso D . . . . . H3 H 0.0873 -0.4808 0.7715 0.0363 1.0000 Uiso R . . . . . H5 H 0.101(3) -0.076(18) 0.987(2) 0.0601 1.0000 Uiso D . . . . . H7 H 0.4697 0.1747 0.9165 0.0386 1.0000 Uiso R . . . . . H8 H 0.4282 -0.1036 0.7625 0.0379 1.0000 Uiso R . . . . . H9 H 0.2630 -0.3310 0.7258 0.0381 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 0.043(11) 0.043(2) 0.036(3) -0.0083(16) -0.002(4) -0.005(3) N2 0.046(11) 0.033(2) 0.023(3) 0.005(2) -0.004(4) -0.009(4) C3 0.045(11) 0.028(2) 0.018(3) 0.008(3) -0.006(5) -0.007(5) C4 0.050(11) 0.022(2) 0.018(2) 0.007(2) 0.000(4) -0.015(4) C5 0.042(10) 0.022(2) 0.020(2) 0.004(2) -0.005(4) 0.001(4) O5 0.049(11) 0.045(2) 0.025(2) -0.0023(18) 0.001(4) -0.007(3) C6 0.046(10) 0.023(2) 0.022(2) 0.004(2) -0.006(4) -0.003(4) Cl6 0.053(6) 0.0325(6) 0.0282(9) -0.0024(5) -0.0112(19) -0.0018(9) C7 0.039(11) 0.030(2) 0.029(2) 0.009(2) -0.007(4) 0.000(4) C8 0.035(11) 0.030(2) 0.030(2) 0.0026(19) -0.002(4) 0.011(4) C9 0.047(11) 0.026(2) 0.022(3) 0.002(2) -0.001(4) -0.003(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.36(14) 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(12) yes O1 . H1 . 0.87(4) no N2 . C3 . 1.271(17) yes C3 . C4 . 1.432(14) yes C3 . H3 . 0.945 no C4 . C5 . 1.420(7) yes C4 . C9 . 1.371(13) yes C5 . O5 . 1.344(10) yes C5 . C6 . 1.358(11) yes O5 . H5 . 0.82(4) no C6 . Cl6 . 1.735(5) yes C6 . C7 . 1.355(11) yes C7 . C8 . 1.408(7) yes C7 . H7 . 0.946 no C8 . C9 . 1.358(13) yes C8 . H8 . 0.921 no C9 . H9 . 0.935 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 . 105.0(9) no O1 . N2 . C3 . 113.0(5) yes N2 . C3 . C4 . 120.3(5) yes N2 . C3 . H3 . 120.2 no C4 . C3 . H3 . 119.5 no C3 . C4 . C5 . 121.0(5) yes C3 . C4 . C9 . 120.3(4) yes C5 . C4 . C9 . 118.7(5) yes C4 . C5 . O5 . 121.5(5) yes C4 . C5 . C6 . 119.3(5) yes O5 . C5 . C6 . 119.3(4) yes C5 . O5 . H5 . 105.0(9) no C5 . C6 . Cl6 . 117.7(5) yes C5 . C6 . C7 . 121.9(4) yes Cl6 . C6 . C7 . 120.3(5) yes C6 . C7 . C8 . 119.1(6) yes C6 . C7 . H7 . 119.2 no C8 . C7 . H7 . 121.6 no C7 . C8 . C9 . 119.7(6) yes C7 . C8 . H8 . 119.7 no C9 . C8 . H8 . 120.6 no C4 . C9 . C8 . 121.3(4) yes C4 . C9 . H9 . 119.1 no C8 . C9 . H9 . 119.6 no _chemical_name_common 3-chlorosalicylaldoxime #END data_Cl34kbar _database_code_depnum_ccdc_archive 'CCDC 657077' _exptl_crystal_recrystallization_method 'Recrystallisation by pressure from methanol/ethanol solution' _audit_creation_date 06-07-19 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-chlorosalicylaldoxime _chemical_melting_point ? _cell_length_a 12.652(4) _cell_length_b 3.5295(4) _cell_length_c 13.509(2) _cell_angle_alpha 90 _cell_angle_beta 93.64(2) _cell_angle_gamma 90 _cell_volume 602.0(2) _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 = C6 H6 Cl1 N1 O2 # Dc = 1.76 Fooo = 352.00 Mu = 5.55 M = 159.57 # Found Formula = C7 H6 Cl1 N1 O2 # Dc = 1.89 FOOO = 352.00 Mu = 5.63 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 1339 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.18 _exptl_crystal_density_diffrn 1.893 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.563 # Sheldrick geometric approximatio 0.92 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2006/1' _exptl_absorpt_correction_T_min 0.37 _exptl_absorpt_correction_T_max 0.95 _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_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'Model taken from ambient pressure structure' _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_ambient_pressure 3400000 _diffrn_reflns_number 2720 _reflns_number_total 416 _diffrn_reflns_av_R_equivalents 0.076 # Number of reflections with Friedels Law is 441 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1194 _diffrn_reflns_theta_min 3.515 _diffrn_reflns_theta_max 26.085 _diffrn_measured_fraction_theta_max 0.346 _diffrn_reflns_theta_full 25.042 _diffrn_measured_fraction_theta_full 0.369 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -4 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 4 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _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 -0.40 _refine_diff_density_max 0.36 _refine_ls_number_reflns 409 _refine_ls_number_restraints 120 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.0973 _refine_ls_wR_factor_ref 0.2271 _refine_ls_goodness_of_fit_ref 1.0203 #_reflns_number_all 409 _refine_ls_R_factor_all 0.0973 _refine_ls_wR_factor_all 0.2271 # 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 319 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_gt 0.2099 _refine_ls_shift/su_max 0.000272 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.13P)^2^ + 2.59P] ,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(5) Angstroms and X-O-H angle restraints of 105(1) degrees. The remaining hydrogens which were placed geometrically were then constrained to ride on their host atom. The primary geometry (bond lengths and angles) has been restrained to agree with the ambient structure with loose esds on the restraints. Global vibration and thermal similarity restraints were also applied. Checkcif output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.37 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.37 088_ALERT_3_A Poor Data / Parameter Ratio .................... 3.86 340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 17 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 061_ALERT_3_A Tmax/Tmin Range Test RR' too Large ............. 0.41 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. 732_ALERT_1_B Angle Calc 105(6), Rep 105.0(9) ...... 6.67 su-Rat N2 -O1 -H1 1.555 1.555 1.555 732_ALERT_1_B Angle Calc 105(4), Rep 105.0(9) ...... 4.44 su-Rat C5 -O5 -H5 1.555 1.555 1.555 731_ALERT_1_C Bond Calc 0.85(9), Rep 0.85(4) ...... 2.25 su-Rat O1 -H1 1.555 1.555 732_ALERT_1_C Angle Calc 119.0(13), Rep 118.9(5) ...... 2.60 su-Rat C5 -C4 -C9 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 119.4(11), Rep 119.4(5) ...... 2.20 su-Rat C4 -C5 -C6 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 118.7(13), Rep 118.8(6) ...... 2.17 su-Rat C6 -C7 -C8 1.555 1.555 1.555 These alerts are due to the fact that PLATON calculates esds using only the variances whereas CRYSTALS uses the full variance/covariance matrix. 213_ALERT_2_C Atom C5 has ADP max/min Ratio ............. 3.70 prolat Noted but no action taken. 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.75 This is probably due to the lack of information in one direction which occurs as a result of the Merrill-Bassett diamond-anvil cell shading a significant region of reciprocal space. The effect of this shading is often to cause a smearing out of electron density in one particular direction. 432_ALERT_2_B Short Inter X...Y Contact O1 .. C3 .. 2.85 Ang. 432_ALERT_2_C Short Inter X...Y Contact Cl6 .. C8 .. 3.21 Ang. 432_ALERT_2_C Short Inter X...Y Contact Cl6 .. C6 .. 3.23 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.16 Ang. 432_ALERT_2_C Short Inter X...Y Contact C7 .. C8 .. 3.19 Ang. Noted but no action taken. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.427 635 271 364 23.01 0.550 0.391 832 325 507 25.24 0.600 0.369 1090 402 688 #----------------------------------------------------------- ACTA Min. Res. ---- 26.08 0.619 0.346 1201 415 786 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O -0.0695(11) -0.4696(19) 0.8549(5) 0.0487 1.0000 Uani D U . . . . N2 N 0.0261(14) -0.308(2) 0.8887(6) 0.0389 1.0000 Uani D U . . . . C3 C 0.0985(15) -0.357(3) 0.8296(7) 0.0386 1.0000 Uani D U . . . . C4 C 0.2031(12) -0.201(2) 0.8533(6) 0.0366 1.0000 Uani D U . . . . C5 C 0.2281(11) -0.020(2) 0.9456(6) 0.0352 1.0000 Uani D U . . . . O5 O 0.1569(11) 0.0088(18) 1.0141(5) 0.0453 1.0000 Uani D U . . . . C6 C 0.3265(9) 0.110(2) 0.9664(6) 0.0364 1.0000 Uani D U . . . . Cl6 Cl 0.3550(4) 0.3132(6) 1.08210(17) 0.0375 1.0000 Uani D U . . . . C7 C 0.4020(12) 0.083(2) 0.9013(7) 0.0351 1.0000 Uani D U . . . . C8 C 0.3767(13) -0.087(2) 0.8094(6) 0.0384 1.0000 Uani D U . . . . C9 C 0.2776(15) -0.228(2) 0.7882(7) 0.0346 1.0000 Uani D U . . . . H1 H -0.114(4) -0.40(4) 0.896(7) 0.0709 1.0000 Uiso D . . . . . H3 H 0.0847 -0.4929 0.7713 0.0450 1.0000 Uiso R . . . . . H5 H 0.099(4) -0.07(4) 0.986(4) 0.0670 1.0000 Uiso D . . . . . H7 H 0.4702 0.1737 0.9182 0.0409 1.0000 Uiso R . . . . . H8 H 0.4277 -0.1037 0.7634 0.0449 1.0000 Uiso R . . . . . H9 H 0.2615 -0.3443 0.7268 0.0400 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 0.070(16) 0.041(4) 0.033(5) -0.002(3) -0.014(7) -0.018(6) N2 0.063(16) 0.028(4) 0.024(6) 0.007(4) -0.012(7) -0.011(6) C3 0.071(17) 0.023(4) 0.020(6) 0.007(4) -0.009(6) -0.010(7) C4 0.074(17) 0.017(3) 0.019(4) 0.003(3) 0.001(5) -0.016(7) C5 0.070(15) 0.024(4) 0.010(4) 0.009(3) -0.004(5) -0.012(6) O5 0.075(15) 0.042(4) 0.019(4) 0.001(3) 0.003(6) -0.017(6) C6 0.066(14) 0.026(4) 0.016(4) 0.002(4) -0.006(5) -0.004(7) Cl6 0.059(10) 0.0293(11) 0.0226(17) -0.0024(8) -0.012(3) -0.0026(15) C7 0.064(15) 0.022(3) 0.018(4) 0.008(3) -0.006(5) -0.002(6) C8 0.065(16) 0.027(4) 0.022(4) -0.001(3) -0.001(6) 0.002(7) C9 0.065(16) 0.017(4) 0.021(5) -0.002(4) -0.006(6) 0.007(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.5(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 O1 . N2 . 1.388(17) yes O1 . H1 . 0.85(4) no N2 . C3 . 1.26(2) yes C3 . C4 . 1.451(18) yes C3 . H3 . 0.929 no C4 . C5 . 1.418(11) yes C4 . C9 . 1.333(17) yes C5 . O5 . 1.336(14) yes C5 . C6 . 1.340(14) yes O5 . H5 . 0.85(4) no C6 . Cl6 . 1.736(8) yes C6 . C7 . 1.342(15) yes C7 . C8 . 1.398(12) yes C7 . H7 . 0.936 no C8 . C9 . 1.361(19) yes C8 . H8 . 0.925 no C9 . H9 . 0.937 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 . 105.0(9) no O1 . N2 . C3 . 112.8(6) yes N2 . C3 . C4 . 119.7(6) yes N2 . C3 . H3 . 120.1 no C4 . C3 . H3 . 120.2 no C3 . C4 . C5 . 121.0(6) yes C3 . C4 . C9 . 120.1(5) yes C5 . C4 . C9 . 118.9(5) yes C4 . C5 . O5 . 121.4(6) yes C4 . C5 . C6 . 119.4(5) yes O5 . C5 . C6 . 119.1(5) yes C5 . O5 . H5 . 105.0(9) no C5 . C6 . Cl6 . 117.9(6) yes C5 . C6 . C7 . 121.8(5) yes Cl6 . C6 . C7 . 120.3(6) yes C6 . C7 . C8 . 118.8(6) yes C6 . C7 . H7 . 119.8 no C8 . C7 . H7 . 121.4 no C7 . C8 . C9 . 119.8(7) yes C7 . C8 . H8 . 119.5 no C9 . C8 . H8 . 120.6 no C8 . C9 . C4 . 121.1(5) yes C8 . C9 . H9 . 119.4 no C4 . C9 . H9 . 119.4 no _chemical_name_common 3-chlorosalicylaldoxime #END data_Cl50kbar _database_code_depnum_ccdc_archive 'CCDC 657078' _exptl_crystal_recrystallization_method 'Recrystallisation by pressure from methanol/ethanol solution' _audit_creation_date 06-07-19 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 3-chlorosalicylaldoxime _chemical_melting_point ? _cell_length_a 12.544(6) _cell_length_b 3.4424(8) _cell_length_c 13.365(5) _cell_angle_alpha 90 _cell_angle_beta 94.44(4) _cell_angle_gamma 90 _cell_volume 575.4(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' 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 = C6 H6 Cl1 N1 O2 # Dc = 1.84 Fooo = 352.00 Mu = 5.81 M = 159.57 # Found Formula = C7 H6 Cl1 N1 O2 # Dc = 1.98 FOOO = 352.00 Mu = 5.89 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 838 _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 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.18 _exptl_crystal_density_diffrn 1.981 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.589 # Sheldrick geometric approximatio 0.93 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2006/1' _exptl_absorpt_correction_T_min 0.27 _exptl_absorpt_correction_T_max 0.94 _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_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'Model taken from ambient pressure structure' _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_ambient_pressure 5000000 _diffrn_reflns_number 3081 _reflns_number_total 351 _diffrn_reflns_av_R_equivalents 0.098 # Number of reflections with Friedels Law is 379 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1118 _diffrn_reflns_theta_min 3.057 _diffrn_reflns_theta_max 25.889 _diffrn_measured_fraction_theta_max 0.314 _diffrn_reflns_theta_full 25.112 _diffrn_measured_fraction_theta_full 0.323 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -3 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 4 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _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 -0.33 _refine_diff_density_max 0.33 _refine_ls_number_reflns 344 _refine_ls_number_restraints 120 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.0775 _refine_ls_wR_factor_ref 0.1234 _refine_ls_goodness_of_fit_ref 0.9958 #_reflns_number_all 344 _refine_ls_R_factor_all 0.0775 _refine_ls_wR_factor_all 0.1234 # 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 231 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_gt 0.1039 _refine_ls_shift/su_max 0.000073 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.71P] ,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(5) Angstroms and X-O-H angle restraints of 105(1) degrees. The remaining hydrogens which were placed geometrically were then constrained to ride on their host atom. The primary geometry (bond lengths and angles) has been restrained to agree with the ambient structure with loose esds on the restraints. Global vibration and thermal similarity restraints were also applied. Checkcif output: 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.34 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.32 088_ALERT_3_A Poor Data / Parameter Ratio .................... 3.25 340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 16 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 061_ALERT_3_A Tmax/Tmin Range Test RR' too Large ............. 0.30 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. 432_ALERT_2_B Short Inter X...Y Contact Cl6 .. C8 .. 3.12 Ang. 432_ALERT_2_B Short Inter X...Y Contact O1 .. C3 .. 2.80 Ang. 432_ALERT_2_C Short Inter X...Y Contact Cl6 .. C6 .. 3.16 Ang. 432_ALERT_2_C Short Inter X...Y Contact C3 .. C5 .. 3.14 Ang. 432_ALERT_2_C Short Inter X...Y Contact C3 .. C4 .. 3.15 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.12 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C6 .. 3.18 Ang. 432_ALERT_2_C Short Inter X...Y Contact C7 .. C8 .. 3.11 Ang. 432_ALERT_2_C Short Inter X...Y Contact C7 .. C9 .. 3.18 Ang. Noted but no action taken - short contacts are expected at high pressure. 732_ALERT_1_B Angle Calc 105(4), Rep 104.9(8) ...... 5.00 su-Rat N2 -O1 -H1 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 119.0(11), Rep 119.1(5) ...... 2.20 su-Rat C5 -C4 -C9 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 121.6(11), Rep 121.7(5) ...... 2.20 su-Rat C4 -C5 -O5 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 105(2), Rep 104.9(8) ...... 2.50 su-Rat C5 -O5 -H5 1.555 1.555 1.555 These alerts are due to the fact that PLATON calculates esds using only the variances whereas CRYSTALS uses the full variance/covariance matrix. 213_ALERT_2_C Atom C3 has ADP max/min Ratio ............. 3.10 oblate Noted but no action taken. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.396 609 241 368 23.01 0.550 0.349 806 281 525 25.24 0.600 0.323 1035 334 701 #----------------------------------------------------------- ACTA Min. Res. ---- 25.89 0.614 0.314 1117 351 766 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O -0.0739(9) -0.4809(14) 0.8546(5) 0.0288 1.0000 Uani D U . . . . N2 N 0.0239(13) -0.312(2) 0.8884(6) 0.0281 1.0000 Uani D U . . . . C3 C 0.0982(14) -0.366(2) 0.8302(6) 0.0218 1.0000 Uani D U . . . . C4 C 0.2014(10) -0.2002(18) 0.8530(5) 0.0216 1.0000 Uani D U . . . . C5 C 0.2283(10) -0.0273(18) 0.9468(6) 0.0233 1.0000 Uani D U . . . . O5 O 0.1571(10) 0.0097(15) 1.0150(5) 0.0318 1.0000 Uani D U . . . . C6 C 0.3282(9) 0.115(2) 0.9687(5) 0.0274 1.0000 Uani D U . . . . Cl6 Cl 0.3559(4) 0.3188(4) 1.08550(16) 0.0318 1.0000 Uani D U . . . . C7 C 0.4066(11) 0.0811(18) 0.9032(6) 0.0250 1.0000 Uani D U . . . . C8 C 0.3805(11) -0.0942(16) 0.8087(5) 0.0220 1.0000 Uani D U . . . . C9 C 0.2791(14) -0.2365(19) 0.7859(6) 0.0223 1.0000 Uani D U . . . . H1 H -0.119(3) -0.38(2) 0.891(5) 0.0441 1.0000 Uiso D . . . . . H3 H 0.0848 -0.5099 0.7705 0.0272 1.0000 Uiso R . . . . . H5 H 0.097(3) -0.03(2) 0.983(2) 0.0481 1.0000 Uiso D . . . . . H7 H 0.4757 0.1703 0.9206 0.0298 1.0000 Uiso R . . . . . H8 H 0.4320 -0.1134 0.7629 0.0269 1.0000 Uiso R . . . . . H9 H 0.2620 -0.3565 0.7242 0.0270 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 0.031(14) 0.030(3) 0.025(4) -0.007(2) 0.001(7) -0.005(4) N2 0.030(14) 0.030(3) 0.023(6) 0.003(4) -0.003(6) -0.005(7) C3 0.035(15) 0.013(3) 0.017(6) 0.010(4) -0.001(6) -0.007(6) C4 0.033(15) 0.019(3) 0.013(4) 0.005(3) 0.001(5) -0.006(6) C5 0.034(12) 0.018(3) 0.017(4) 0.000(3) -0.003(5) 0.005(6) O5 0.045(13) 0.033(2) 0.018(4) -0.005(3) 0.004(5) -0.005(5) C6 0.041(13) 0.025(3) 0.016(4) 0.003(4) -0.003(5) -0.005(7) Cl6 0.050(9) 0.0243(7) 0.0199(13) -0.0007(8) -0.008(3) -0.0009(13) C7 0.033(14) 0.016(3) 0.025(4) 0.002(3) -0.004(4) 0.001(6) C8 0.025(15) 0.019(3) 0.021(3) 0.004(3) -0.003(5) 0.009(5) C9 0.029(15) 0.019(3) 0.018(4) 0.000(3) -0.001(6) 0.003(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.34(15) 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 . 1.400(15) yes O1 . H1 . 0.85(4) no N2 . C3 . 1.27(2) yes C3 . C4 . 1.426(16) yes C3 . H3 . 0.943 no C4 . C5 . 1.404(8) yes C4 . C9 . 1.380(17) yes C5 . O5 . 1.331(14) yes C5 . C6 . 1.356(12) yes O5 . H5 . 0.84(4) no C6 . Cl6 . 1.722(7) yes C6 . C7 . 1.372(14) yes C7 . C8 . 1.415(9) yes C7 . H7 . 0.932 no C8 . C9 . 1.375(15) yes C8 . H8 . 0.926 no C9 . H9 . 0.933 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 . 104.9(8) no O1 . N2 . C3 . 114.0(6) yes N2 . C3 . C4 . 120.5(6) yes N2 . C3 . H3 . 120.2 no C4 . C3 . H3 . 119.3 no C3 . C4 . C5 . 120.7(5) yes C3 . C4 . C9 . 120.0(5) yes C5 . C4 . C9 . 119.1(5) yes C4 . C5 . O5 . 121.7(5) yes C4 . C5 . C6 . 120.0(5) yes O5 . C5 . C6 . 118.3(5) yes C5 . O5 . H5 . 104.9(8) no C5 . C6 . Cl6 . 117.5(5) yes C5 . C6 . C7 . 121.9(4) yes Cl6 . C6 . C7 . 120.5(6) yes C6 . C7 . C8 . 118.5(6) yes C6 . C7 . H7 . 120.8 no C8 . C7 . H7 . 120.6 no C7 . C8 . C9 . 119.8(6) yes C7 . C8 . H8 . 119.7 no C9 . C8 . H8 . 120.6 no C4 . C9 . C8 . 120.7(5) yes C4 . C9 . H9 . 119.3 no C8 . C9 . H9 . 120.0 no _chemical_name_common 3-chlorosalicylaldoxime #END data_MeO14kbar _database_code_depnum_ccdc_archive 'CCDC 657079' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of chloroform solution' _audit_creation_date 06-10-12 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.0765(5) _cell_length_b 7.0982(4) _cell_length_c 15.2455(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1415.08(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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C8 H9 N1 O3 # Dc = 1.57 Fooo = 704.00 Mu = 1.21 M = 167.16 # Found Formula = C8 H9 N1 O3 # Dc = 1.57 FOOO = 704.00 Mu = 1.21 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 2154 _cell_measurement_theta_min 2 _cell_measurement_theta_max 17 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.121 # 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 0.34 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48720 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 1400000 _diffrn_reflns_number 12848 _reflns_number_total 1160 _diffrn_reflns_av_R_equivalents 0.117 # Number of reflections with Friedels Law is 1340 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1455 _diffrn_reflns_theta_min 2.120 _diffrn_reflns_theta_max 17.762 _diffrn_measured_fraction_theta_max 0.798 _diffrn_reflns_theta_full 13.321 _diffrn_measured_fraction_theta_full 0.842 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min 0 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _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 0.15 _refine_ls_number_reflns 1155 _refine_ls_number_restraints 2 _refine_ls_number_parameters 116 #_refine_ls_R_factor_ref 0.0857 _refine_ls_wR_factor_ref 0.1526 _refine_ls_goodness_of_fit_ref 0.9357 #_reflns_number_all 1155 _refine_ls_R_factor_all 0.0857 _refine_ls_wR_factor_all 0.1526 # 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 733 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_gt 0.1218 _refine_ls_shift/su_max 0.000162 # 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: 89.6 143. 86.5 35.2 8.60 ; _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: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.32 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.84 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92 088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.96 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 432_ALERT_2_C Short Inter X...Y Contact C5 .. C7 .. 3.19 Ang. This short intermolecular contact is simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 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 #------------------------------------------------------------------------------- 14.10 0.500 0.836 738 617 121 15.54 0.550 0.827 986 815 171 17.00 0.600 0.808 1284 1037 247 #----------------------------------------------------------- ACTA Min. Res. ---- 17.76 0.626 0.798 1454 1160 294 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.48742(19) -0.0183(4) 0.67811(12) 0.0429 1.0000 Uani D . . . . . N2 N 0.52884(19) 0.1016(4) 0.61483(15) 0.0330 1.0000 Uani . . . . . . C3 C 0.5591(2) 0.2584(6) 0.64472(18) 0.0340 1.0000 Uani . . . . . . C4 C 0.5994(2) 0.4006(5) 0.58545(17) 0.0284 1.0000 Uani . . . . . . C5 C 0.6106(2) 0.3628(5) 0.49583(18) 0.0272 1.0000 Uani . . . . . . O5 O 0.59083(16) 0.1921(4) 0.46076(12) 0.0335 1.0000 Uani D . . . . . C6 C 0.6441(2) 0.5054(5) 0.43900(18) 0.0305 1.0000 Uani . . . . . . O61 O 0.65027(16) 0.4504(4) 0.35281(12) 0.0388 1.0000 Uani . . . . . . C62 C 0.6977(3) 0.5806(6) 0.2945(2) 0.0451 1.0000 Uani . . . . . . C7 C 0.6688(2) 0.6790(6) 0.4718(2) 0.0382 1.0000 Uani . . . . . . C8 C 0.6589(2) 0.7171(6) 0.5611(2) 0.0396 1.0000 Uani . . . . . . C9 C 0.6244(2) 0.5794(5) 0.61742(19) 0.0329 1.0000 Uani . . . . . . H1 H 0.457(3) -0.097(7) 0.648(3) 0.0641 1.0000 Uiso D . . . . . H3 H 0.5546 0.2852 0.7047 0.0411 1.0000 Uiso R . . . . . H5 H 0.568(3) 0.116(6) 0.501(3) 0.0512 1.0000 Uiso D . . . . . H621 H 0.7040 0.5238 0.2373 0.0678 1.0000 Uiso R . . . . . H622 H 0.7649 0.6143 0.3151 0.0682 1.0000 Uiso R . . . . . H623 H 0.6591 0.6939 0.2878 0.0681 1.0000 Uiso R . . . . . H7 H 0.6921 0.7720 0.4339 0.0454 1.0000 Uiso R . . . . . H8 H 0.6768 0.8339 0.5826 0.0472 1.0000 Uiso R . . . . . H9 H 0.6178 0.6014 0.6780 0.0401 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 0.0631(15) 0.042(2) 0.0236(10) 0.0047(10) 0.0028(9) -0.0138(12) N2 0.0387(14) 0.037(2) 0.0239(11) 0.0056(12) 0.0019(9) -0.0014(12) C3 0.0315(14) 0.044(3) 0.0267(13) -0.0040(13) -0.0002(11) -0.0002(13) C4 0.0255(14) 0.031(3) 0.0284(13) -0.0018(13) -0.0006(10) 0.0025(12) C5 0.0259(14) 0.022(3) 0.0332(14) -0.0029(12) -0.0029(10) 0.0013(11) O5 0.0452(12) 0.028(2) 0.0270(10) -0.0029(9) 0.0034(8) -0.0072(9) C6 0.0285(13) 0.034(3) 0.0292(13) 0.0015(13) -0.0029(10) 0.0017(12) O61 0.0475(13) 0.042(2) 0.0269(10) 0.0037(10) 0.0015(8) -0.0061(10) C62 0.0490(19) 0.048(3) 0.0381(16) 0.0112(16) 0.0066(13) -0.0077(16) C7 0.0242(14) 0.047(3) 0.0433(16) 0.0021(17) -0.0007(11) -0.0025(13) C8 0.0296(15) 0.042(3) 0.0475(17) -0.0143(16) 0.0020(12) -0.0018(13) C9 0.0340(15) 0.032(3) 0.0329(14) -0.0080(14) 0.0011(11) 0.0021(13) _refine_ls_extinction_coef 1170(160) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.985(12) 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 . 1.396(3) yes O1 . H1 . 0.83(4) no N2 . C3 . 1.266(5) yes C3 . C4 . 1.454(5) yes C3 . H3 . 0.936 no C4 . C5 . 1.400(4) yes C4 . C9 . 1.398(5) yes C5 . O5 . 1.349(4) yes C5 . C6 . 1.403(5) yes O5 . H5 . 0.87(3) no C6 . O61 . 1.373(3) yes C6 . C7 . 1.369(5) yes O61 . C62 . 1.424(4) yes C62 . H621 . 0.964 no C62 . H622 . 0.963 no C62 . H623 . 0.955 no C7 . C8 . 1.394(4) yes C7 . H7 . 0.929 no C8 . C9 . 1.377(5) yes C8 . H8 . 0.922 no C9 . H9 . 0.940 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 . 102(3) no O1 . N2 . C3 . 114.1(2) yes N2 . C3 . C4 . 120.0(3) yes N2 . C3 . H3 . 120.7 no C4 . C3 . H3 . 119.3 no C3 . C4 . C5 . 120.8(3) yes C3 . C4 . C9 . 119.9(3) yes C5 . C4 . C9 . 119.3(3) yes C4 . C5 . O5 . 122.6(3) yes C4 . C5 . C6 . 119.8(3) yes O5 . C5 . C6 . 117.6(3) yes C5 . O5 . H5 . 110(3) no C5 . C6 . O61 . 113.9(3) yes C5 . C6 . C7 . 119.9(3) yes O61 . C6 . C7 . 126.3(3) yes C6 . O61 . C62 . 116.0(3) yes O61 . C62 . H621 . 109.3 no O61 . C62 . H622 . 110.8 no H621 . C62 . H622 . 108.6 no O61 . C62 . H623 . 112.6 no H621 . C62 . H623 . 107.4 no H622 . C62 . H623 . 108.0 no C6 . C7 . C8 . 120.6(3) yes C6 . C7 . H7 . 119.3 no C8 . C7 . H7 . 120.0 no C7 . C8 . C9 . 120.1(4) yes C7 . C8 . H8 . 119.9 no C9 . C8 . H8 . 120.0 no C4 . C9 . C8 . 120.2(3) yes C4 . C9 . H9 . 118.2 no C8 . C9 . H9 . 121.6 no #END data_MeO27kbar _database_code_depnum_ccdc_archive 'CCDC 657080' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of chloroform solution' _audit_creation_date 06-10-12 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.5814(4) _cell_length_b 7.0265(4) _cell_length_c 15.0188(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1327.71(9) _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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C8 H9 N1 O3 # Dc = 1.67 Fooo = 704.00 Mu = 1.29 M = 167.16 # Found Formula = C8 H9 N1 O3 # Dc = 1.67 FOOO = 704.00 Mu = 1.29 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 2389 _cell_measurement_theta_min 2 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.129 # 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 0.27 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48720 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 2700000 _diffrn_reflns_number 12227 _reflns_number_total 1090 _diffrn_reflns_av_R_equivalents 0.106 # Number of reflections with Friedels Law is 1261 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4232 _diffrn_reflns_theta_min 2.165 _diffrn_reflns_theta_max 17.753 _diffrn_measured_fraction_theta_max 0.799 _diffrn_reflns_theta_full 13.847 _diffrn_measured_fraction_theta_full 0.836 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min 0 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _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 -0.18 _refine_diff_density_max 0.15 _refine_ls_number_reflns 1087 _refine_ls_number_restraints 2 _refine_ls_number_parameters 115 #_refine_ls_R_factor_ref 0.0679 _refine_ls_wR_factor_ref 0.1193 _refine_ls_goodness_of_fit_ref 0.9038 #_reflns_number_all 1087 _refine_ls_R_factor_all 0.0679 _refine_ls_wR_factor_all 0.1193 # 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 743 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_gt 0.0969 _refine_ls_shift/su_max 0.000194 # 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: 62.8 94.3 55.7 20.6 6.40 ; _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: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.85 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.84 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92 088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.45 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 432_ALERT_2_B Short Inter X...Y Contact C5 .. C7 .. 3.09 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C6 .. 3.17 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 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 #------------------------------------------------------------------------------- 14.10 0.500 0.836 696 582 114 15.54 0.550 0.827 927 767 160 17.00 0.600 0.806 1203 970 233 #----------------------------------------------------------- ACTA Min. Res. ---- 17.75 0.626 0.799 1365 1090 275 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.48778(15) -0.0227(4) 0.68007(10) 0.0338 1.0000 Uani D . . . . . N2 N 0.52963(16) 0.1003(4) 0.61613(12) 0.0257 1.0000 Uani . . . . . . C3 C 0.56227(18) 0.2575(5) 0.64700(14) 0.0257 1.0000 Uani . . . . . . C4 C 0.60149(17) 0.4015(4) 0.58626(14) 0.0225 1.0000 Uani . . . . . . C5 C 0.61158(17) 0.3642(4) 0.49534(15) 0.0227 1.0000 Uani . . . . . . O5 O 0.59315(14) 0.1892(3) 0.46024(10) 0.0269 1.0000 Uani D . . . . . C6 C 0.64380(18) 0.5076(4) 0.43717(14) 0.0226 1.0000 Uani . . . . . . O61 O 0.64879(14) 0.4518(3) 0.34959(10) 0.0316 1.0000 Uani . . . . . . C62 C 0.6990(2) 0.5834(5) 0.29099(16) 0.0361 1.0000 Uani . . . . . . C7 C 0.66643(18) 0.6857(4) 0.46929(16) 0.0265 1.0000 Uani . . . . . . C8 C 0.65795(19) 0.7235(5) 0.56003(17) 0.0302 1.0000 Uani . . . . . . C9 C 0.62481(19) 0.5832(4) 0.61773(16) 0.0263 1.0000 Uani . . . . . . H1 H 0.465(3) -0.104(5) 0.641(2) 0.0510 1.0000 Uiso D . . . . . H3 H 0.5593 0.2816 0.7087 0.0310 1.0000 Uiso R . . . . . H5 H 0.570(3) 0.121(5) 0.504(2) 0.0409 1.0000 Uiso D . . . . . H621 H 0.7027 0.5215 0.2330 0.0538 1.0000 Uiso R . . . . . H622 H 0.7700 0.6111 0.3115 0.0543 1.0000 Uiso R . . . . . H623 H 0.6577 0.6994 0.2869 0.0546 1.0000 Uiso R . . . . . H7 H 0.6886 0.7807 0.4296 0.0325 1.0000 Uiso R . . . . . H8 H 0.6744 0.8449 0.5813 0.0360 1.0000 Uiso R . . . . . H9 H 0.6186 0.6082 0.6789 0.0321 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 0.0490(12) 0.0333(17) 0.0190(8) 0.0027(8) 0.0039(7) -0.0119(9) N2 0.0307(11) 0.0247(18) 0.0218(9) 0.0061(9) 0.0023(8) -0.0041(9) C3 0.0274(12) 0.028(2) 0.0215(10) -0.0042(10) 0.0006(9) 0.0015(11) C4 0.0170(11) 0.027(2) 0.0234(11) -0.0020(10) -0.0004(8) 0.0019(9) C5 0.0186(11) 0.025(2) 0.0249(11) -0.0015(10) -0.0023(8) 0.0018(10) O5 0.0353(10) 0.0240(16) 0.0215(8) -0.0024(8) -0.0001(7) -0.0067(8) C6 0.0230(12) 0.022(2) 0.0228(10) 0.0015(10) -0.0017(8) 0.0023(9) O61 0.0375(10) 0.0358(17) 0.0216(8) 0.0033(8) 0.0006(7) -0.0062(8) C62 0.0383(14) 0.044(3) 0.0256(12) 0.0079(12) 0.0045(10) -0.0062(13) C7 0.0198(11) 0.024(2) 0.0355(12) 0.0031(12) 0.0010(9) -0.0003(10) C8 0.0239(12) 0.028(2) 0.0385(13) -0.0100(12) 0.0001(10) -0.0007(10) C9 0.0248(12) 0.025(2) 0.0285(11) -0.0068(11) 0.0010(9) 0.0003(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.154(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 O1 . N2 . 1.395(3) yes O1 . H1 . 0.87(3) no N2 . C3 . 1.267(4) yes C3 . C4 . 1.449(4) yes C3 . H3 . 0.943 no C4 . C5 . 1.396(3) yes C4 . C9 . 1.393(4) yes C5 . O5 . 1.357(3) yes C5 . C6 . 1.394(4) yes O5 . H5 . 0.86(3) no C6 . O61 . 1.374(3) yes C6 . C7 . 1.371(4) yes O61 . C62 . 1.424(3) yes C62 . H621 . 0.974 no C62 . H622 . 0.965 no C62 . H623 . 0.969 no C7 . C8 . 1.393(3) yes C7 . H7 . 0.937 no C8 . C9 . 1.377(4) yes C8 . H8 . 0.934 no C9 . H9 . 0.939 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 . 94(2) no O1 . N2 . C3 . 114.26(19) yes N2 . C3 . C4 . 119.3(2) yes N2 . C3 . H3 . 120.2 no C4 . C3 . H3 . 120.5 no C3 . C4 . C5 . 121.0(3) yes C3 . C4 . C9 . 119.9(2) yes C5 . C4 . C9 . 119.0(2) yes C4 . C5 . O5 . 122.3(2) yes C4 . C5 . C6 . 120.2(3) yes O5 . C5 . C6 . 117.4(2) yes C5 . O5 . H5 . 105(2) no C5 . C6 . O61 . 114.0(3) yes C5 . C6 . C7 . 120.0(2) yes O61 . C6 . C7 . 126.0(2) yes C6 . O61 . C62 . 115.3(2) yes O61 . C62 . H621 . 106.5 no O61 . C62 . H622 . 110.1 no H621 . C62 . H622 . 109.3 no O61 . C62 . H623 . 110.4 no H621 . C62 . H623 . 110.2 no H622 . C62 . H623 . 110.3 no C6 . C7 . C8 . 120.2(3) yes C6 . C7 . H7 . 119.2 no C8 . C7 . H7 . 120.6 no C7 . C8 . C9 . 120.2(3) yes C7 . C8 . H8 . 119.5 no C9 . C8 . H8 . 120.4 no C4 . C9 . C8 . 120.4(2) yes C4 . C9 . H9 . 119.1 no C8 . C9 . H9 . 120.5 no #END data_MeO44kbar _database_code_depnum_ccdc_archive 'CCDC 657081' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of chloroform solution' _audit_creation_date 06-10-12 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.3113(5) _cell_length_b 6.9800(4) _cell_length_c 14.8947(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1279.94(10) _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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C8 H9 N1 O3 # Dc = 1.73 Fooo = 704.00 Mu = 1.34 M = 167.16 # Found Formula = C8 H9 N1 O3 # Dc = 1.73 FOOO = 704.00 Mu = 1.34 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 2349 _cell_measurement_theta_min 3 _cell_measurement_theta_max 19 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.134 # 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 0.21 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48720 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 4400000 _diffrn_reflns_number 12201 _reflns_number_total 1425 _diffrn_reflns_av_R_equivalents 0.110 # Number of reflections with Friedels Law is 1619 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1959 _diffrn_reflns_theta_min 2.191 _diffrn_reflns_theta_max 20.385 _diffrn_measured_fraction_theta_max 0.730 _diffrn_reflns_theta_full 15.493 _diffrn_measured_fraction_theta_full 0.813 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min 0 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _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 -0.19 _refine_diff_density_max 0.25 _refine_ls_number_reflns 1424 _refine_ls_number_restraints 149 _refine_ls_number_parameters 115 #_refine_ls_R_factor_ref 0.0863 _refine_ls_wR_factor_ref 0.1619 _refine_ls_goodness_of_fit_ref 0.8651 #_reflns_number_all 1424 _refine_ls_R_factor_all 0.0863 _refine_ls_wR_factor_all 0.1619 # 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 890 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_gt 0.1252 _refine_ls_shift/su_max 0.000203 # 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: 75.7 117. 69.7 27.2 7.09 ; _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: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 15.49 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.81 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 432_ALERT_2_B Short Inter X...Y Contact C5 .. C7 .. 3.02 Ang. 413_ALERT_2_C Short Inter XH3 .. XHn H9 .. H623 .. 2.10 Ang. 432_ALERT_2_C Short Inter X...Y Contact O5 .. C7 .. 2.96 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C6 .. 3.10 Ang. 432_ALERT_2_C Short Inter X...Y Contact C5 .. C8 .. 3.15 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 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 #------------------------------------------------------------------------------- 14.10 0.500 0.820 672 551 121 15.54 0.550 0.815 898 732 166 17.00 0.600 0.798 1161 926 235 #----------------------------------------------------------- ACTA Min. Res. ---- 18.46 0.650 0.782 1468 1148 320 19.94 0.700 0.752 1833 1378 455 20.38 0.715 0.730 1953 1425 528 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.48832(16) -0.0257(4) 0.68105(10) 0.0303 1.0000 Uani D . . . . . N2 N 0.52970(16) 0.0989(4) 0.61710(11) 0.0225 1.0000 Uani . . . . . . C3 C 0.56425(18) 0.2558(4) 0.64851(14) 0.0229 1.0000 Uani . . . . . . C4 C 0.60256(17) 0.4039(4) 0.58695(13) 0.0201 1.0000 Uani . . . . . . C5 C 0.61199(17) 0.3638(4) 0.49513(13) 0.0185 1.0000 Uani . . . . . . O5 O 0.59428(14) 0.1875(3) 0.46040(10) 0.0239 1.0000 Uani D . . . . . C6 C 0.64287(17) 0.5083(4) 0.43629(13) 0.0201 1.0000 Uani . . . . . . O61 O 0.64787(14) 0.4530(3) 0.34810(10) 0.0277 1.0000 Uani . . . . . . C62 C 0.7005(2) 0.5823(5) 0.28909(15) 0.0304 1.0000 Uani . . . . . . C7 C 0.66558(18) 0.6893(4) 0.46805(15) 0.0233 1.0000 Uani . . . . . . C8 C 0.65729(18) 0.7271(5) 0.55987(16) 0.0249 1.0000 Uani . . . . . . C9 C 0.62541(19) 0.5853(4) 0.61827(14) 0.0234 1.0000 Uani . . . . . . H1 H 0.461(3) -0.116(5) 0.647(2) 0.0451 1.0000 Uiso D . . . . . H3 H 0.5635 0.2794 0.7109 0.0280 1.0000 Uiso R . . . . . H5 H 0.570(3) 0.120(5) 0.504(2) 0.0370 1.0000 Uiso D . . . . . H621 H 0.7047 0.5246 0.2307 0.0457 1.0000 Uiso R . . . . . H622 H 0.7728 0.6092 0.3101 0.0465 1.0000 Uiso R . . . . . H623 H 0.6612 0.7022 0.2850 0.0457 1.0000 Uiso R . . . . . H7 H 0.6860 0.7846 0.4279 0.0284 1.0000 Uiso R . . . . . H8 H 0.6717 0.8499 0.5810 0.0301 1.0000 Uiso R . . . . . H9 H 0.6180 0.6130 0.6797 0.0277 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 0.0425(10) 0.0312(16) 0.0170(7) 0.0040(7) 0.0038(6) -0.0095(8) N2 0.0268(9) 0.0236(16) 0.0171(7) 0.0017(7) 0.0014(6) -0.0024(8) C3 0.0253(10) 0.0240(19) 0.0193(9) -0.0018(8) 0.0003(7) 0.0005(9) C4 0.0195(10) 0.0204(18) 0.0204(9) -0.0022(8) -0.0003(7) 0.0002(8) C5 0.0196(10) 0.0156(17) 0.0204(8) -0.0030(8) -0.0022(7) -0.0012(8) O5 0.0311(9) 0.0225(14) 0.0183(7) -0.0020(6) 0.0003(6) -0.0055(7) C6 0.0185(9) 0.0228(18) 0.0189(9) -0.0013(8) -0.0010(6) -0.0009(8) O61 0.0349(10) 0.0301(15) 0.0182(7) 0.0018(7) 0.0006(6) -0.0049(7) C62 0.0323(12) 0.037(2) 0.0222(10) 0.0048(10) 0.0027(8) -0.0067(11) C7 0.0223(10) 0.0192(19) 0.0284(10) 0.0032(9) -0.0001(8) -0.0019(8) C8 0.0225(10) 0.0200(19) 0.0322(11) -0.0055(9) 0.0009(8) -0.0014(8) C9 0.0232(10) 0.0240(19) 0.0230(9) -0.0053(9) -0.0006(7) 0.0011(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.088(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 O1 . N2 . 1.387(3) yes O1 . H1 . 0.87(3) no N2 . C3 . 1.265(4) yes C3 . C4 . 1.460(4) yes C3 . H3 . 0.944 no C4 . C5 . 1.401(3) yes C4 . C9 . 1.378(4) yes C5 . O5 . 1.353(3) yes C5 . C6 . 1.389(4) yes O5 . H5 . 0.86(3) no C6 . O61 . 1.370(3) yes C6 . C7 . 1.377(4) yes O61 . C62 . 1.416(3) yes C62 . H621 . 0.960 no C62 . H622 . 0.962 no C62 . H623 . 0.969 no C7 . C8 . 1.397(3) yes C7 . H7 . 0.929 no C8 . C9 . 1.375(4) yes C8 . H8 . 0.931 no C9 . H9 . 0.939 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(2) no O1 . N2 . C3 . 114.36(18) yes N2 . C3 . C4 . 119.32(19) yes N2 . C3 . H3 . 120.8 no C4 . C3 . H3 . 119.9 no C3 . C4 . C5 . 119.9(2) yes C3 . C4 . C9 . 120.3(2) yes C5 . C4 . C9 . 119.8(2) yes C4 . C5 . O5 . 122.8(2) yes C4 . C5 . C6 . 119.6(2) yes O5 . C5 . C6 . 117.61(19) yes C5 . O5 . H5 . 105(2) no C5 . C6 . O61 . 114.4(2) yes C5 . C6 . C7 . 120.30(19) yes O61 . C6 . C7 . 125.3(2) yes C6 . O61 . C62 . 115.8(2) yes O61 . C62 . H621 . 108.7 no O61 . C62 . H622 . 110.3 no H621 . C62 . H622 . 109.0 no O61 . C62 . H623 . 111.2 no H621 . C62 . H623 . 109.5 no H622 . C62 . H623 . 108.2 no C6 . C7 . C8 . 119.7(2) yes C6 . C7 . H7 . 119.4 no C8 . C7 . H7 . 121.0 no C7 . C8 . C9 . 120.3(3) yes C7 . C8 . H8 . 119.4 no C9 . C8 . H8 . 120.2 no C4 . C9 . C8 . 120.4(2) yes C4 . C9 . H9 . 119.9 no C8 . C9 . H9 . 119.7 no #END data_MeO53kbar _database_code_depnum_ccdc_archive 'CCDC 657082' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of chloroform solution' _audit_creation_date 06-10-12 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.1340(13) _cell_length_b 6.9421(11) _cell_length_c 14.8065(13) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1247.2(3) _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 0.0010 0.0020 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 0.0030 0.0040 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 = C8 H9 N1 O3 # Dc = 1.78 Fooo = 704.00 Mu = 1.38 M = 167.16 # Found Formula = C8 H9 N1 O3 # Dc = 1.78 FOOO = 704.00 Mu = 1.38 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 2511 _cell_measurement_theta_min 2 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.780 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.138 # 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 0.30 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48720 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 5300000 _diffrn_reflns_number 11069 _reflns_number_total 1033 _diffrn_reflns_av_R_equivalents 0.111 # Number of reflections with Friedels Law is 1194 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1280 _diffrn_reflns_theta_min 2.209 _diffrn_reflns_theta_max 17.749 _diffrn_measured_fraction_theta_max 0.804 _diffrn_reflns_theta_full 13.312 _diffrn_measured_fraction_theta_full 0.847 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _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 -0.24 _refine_diff_density_max 0.24 _refine_ls_number_reflns 1029 _refine_ls_number_restraints 149 _refine_ls_number_parameters 116 #_refine_ls_R_factor_ref 0.0696 _refine_ls_wR_factor_ref 0.1436 _refine_ls_goodness_of_fit_ref 0.8503 #_reflns_number_all 1029 _refine_ls_R_factor_all 0.0696 _refine_ls_wR_factor_all 0.1436 # 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 737 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_gt 0.1230 _refine_ls_shift/su_max 0.000232 # 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: 87.1 137. 83.3 33.6 8.95 ; _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: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.31 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.85 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.87 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 413_ALERT_2_B Short Inter XH3 .. XHn H9 .. H623 .. 2.05 Ang. 432_ALERT_2_B Short Inter X...Y Contact O5 .. C7 .. 2.91 Ang. 432_ALERT_2_B Short Inter X...Y Contact C4 .. C6 .. 3.06 Ang. 432_ALERT_2_B Short Inter X...Y Contact C5 .. C7 .. 2.99 Ang. 432_ALERT_2_C Short Inter X...Y Contact O1 .. C3 .. 2.99 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C8 .. 3.17 Ang. 432_ALERT_2_C Short Inter X...Y Contact C5 .. C8 .. 3.10 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 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 #------------------------------------------------------------------------------- 14.10 0.500 0.840 655 550 105 15.54 0.550 0.828 868 719 149 17.00 0.600 0.813 1131 919 212 #----------------------------------------------------------- ACTA Min. Res. ---- 17.75 0.626 0.805 1284 1033 251 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.48842(16) -0.0289(4) 0.68171(11) 0.0295 1.0000 Uani D . . . . . N2 N 0.52956(17) 0.0982(4) 0.61777(12) 0.0224 1.0000 Uani . . . . . . C3 C 0.56536(19) 0.2552(4) 0.64939(14) 0.0221 1.0000 Uani . . . . . . C4 C 0.60283(18) 0.4030(4) 0.58734(14) 0.0224 1.0000 Uani . . . . . . C5 C 0.61191(18) 0.3644(4) 0.49527(15) 0.0196 1.0000 Uani . . . . . . O5 O 0.59512(14) 0.1868(3) 0.46051(10) 0.0234 1.0000 Uani D . . . . . C6 C 0.64270(19) 0.5096(4) 0.43613(15) 0.0212 1.0000 Uani . . . . . . O61 O 0.64722(15) 0.4535(3) 0.34718(10) 0.0273 1.0000 Uani . . . . . . C62 C 0.7014(2) 0.5846(5) 0.28814(16) 0.0308 1.0000 Uani . . . . . . C7 C 0.66484(19) 0.6909(4) 0.46755(16) 0.0242 1.0000 Uani . . . . . . C8 C 0.65775(19) 0.7289(5) 0.55959(16) 0.0252 1.0000 Uani . . . . . . C9 C 0.6256(2) 0.5869(4) 0.61868(15) 0.0236 1.0000 Uani . . . . . . H1 H 0.454(3) -0.105(5) 0.645(2) 0.0440 1.0000 Uiso D . . . . . H3 H 0.5647 0.2761 0.7112 0.0282 1.0000 Uiso R . . . . . H5 H 0.575(3) 0.121(5) 0.502(2) 0.0357 1.0000 Uiso D . . . . . H621 H 0.7068 0.5239 0.2295 0.0451 1.0000 Uiso R . . . . . H622 H 0.7748 0.6135 0.3097 0.0463 1.0000 Uiso R . . . . . H623 H 0.6589 0.7021 0.2833 0.0462 1.0000 Uiso R . . . . . H7 H 0.6831 0.7866 0.4265 0.0289 1.0000 Uiso R . . . . . H8 H 0.6737 0.8541 0.5803 0.0300 1.0000 Uiso R . . . . . H9 H 0.6194 0.6131 0.6807 0.0288 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 0.0397(11) 0.0320(17) 0.0169(8) 0.0033(7) 0.0021(7) -0.0097(8) N2 0.0282(11) 0.0210(17) 0.0180(9) 0.0063(8) 0.0018(7) -0.0024(9) C3 0.0289(12) 0.017(2) 0.0202(11) -0.0035(9) 0.0009(9) 0.0013(9) C4 0.0185(11) 0.030(2) 0.0192(11) -0.0025(10) -0.0008(8) 0.0013(9) C5 0.0214(12) 0.0162(19) 0.0211(10) -0.0032(9) -0.0011(8) 0.0009(9) O5 0.0300(10) 0.0224(15) 0.0177(8) -0.0015(7) 0.0003(6) -0.0044(7) C6 0.0211(12) 0.023(2) 0.0192(11) -0.0006(10) -0.0012(8) 0.0009(9) O61 0.0354(11) 0.0282(16) 0.0185(9) 0.0012(7) 0.0010(6) -0.0035(8) C62 0.0362(15) 0.036(2) 0.0207(11) 0.0034(11) 0.0027(9) -0.0065(12) C7 0.0197(12) 0.025(2) 0.0281(12) 0.0026(11) 0.0012(8) -0.0014(9) C8 0.0207(12) 0.023(2) 0.0316(12) -0.0035(11) 0.0003(9) 0.0004(9) C9 0.0268(12) 0.023(2) 0.0212(11) -0.0040(10) -0.0003(8) 0.0016(10) _refine_ls_extinction_coef 1010(150) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 1.149(16) 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 . 1.387(3) yes O1 . H1 . 0.86(3) no N2 . C3 . 1.264(4) yes C3 . C4 . 1.450(4) yes C3 . H3 . 0.927 no C4 . C5 . 1.394(3) yes C4 . C9 . 1.386(4) yes C5 . O5 . 1.351(3) yes C5 . C6 . 1.387(4) yes O5 . H5 . 0.81(3) no C6 . O61 . 1.375(3) yes C6 . C7 . 1.369(4) yes O61 . C62 . 1.423(3) yes C62 . H621 . 0.968 no C62 . H622 . 0.967 no C62 . H623 . 0.968 no C7 . C8 . 1.391(3) yes C7 . H7 . 0.927 no C8 . C9 . 1.374(4) yes C8 . H8 . 0.942 no C9 . H9 . 0.939 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 . 98(2) no O1 . N2 . C3 . 114.82(19) yes N2 . C3 . C4 . 118.9(2) yes N2 . C3 . H3 . 119.9 no C4 . C3 . H3 . 121.2 no C3 . C4 . C5 . 120.5(3) yes C3 . C4 . C9 . 120.1(2) yes C5 . C4 . C9 . 119.3(2) yes C4 . C5 . O5 . 122.4(2) yes C4 . C5 . C6 . 119.9(3) yes O5 . C5 . C6 . 117.6(2) yes C5 . O5 . H5 . 106(2) no C5 . C6 . O61 . 114.2(2) yes C5 . C6 . C7 . 120.5(2) yes O61 . C6 . C7 . 125.3(2) yes C6 . O61 . C62 . 115.2(2) yes O61 . C62 . H621 . 107.7 no O61 . C62 . H622 . 110.8 no H621 . C62 . H622 . 108.9 no O61 . C62 . H623 . 109.8 no H621 . C62 . H623 . 109.7 no H622 . C62 . H623 . 110.0 no C6 . C7 . C8 . 119.7(3) yes C6 . C7 . H7 . 118.9 no C8 . C7 . H7 . 121.4 no C7 . C8 . C9 . 120.4(3) yes C7 . C8 . H8 . 118.8 no C9 . C8 . H8 . 120.8 no C4 . C9 . C8 . 120.3(2) yes C4 . C9 . H9 . 119.3 no C8 . C9 . H9 . 120.5 no #END data_MeO60kbar _database_code_depnum_ccdc_archive 'CCDC 657083' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of chloroform solution' _audit_creation_date 06-10-12 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.0702(5) _cell_length_b 6.9200(5) _cell_length_c 14.7703(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1233.70(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 0.0000 0.0010 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 0.0010 0.0020 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 0.0030 0.0040 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 = C8 H9 N1 O3 # Dc = 1.80 Fooo = 704.00 Mu = 1.39 M = 167.16 # Found Formula = C8 H9 N1 O3 # Dc = 1.80 FOOO = 704.00 Mu = 1.39 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 2025 _cell_measurement_theta_min 2 _cell_measurement_theta_max 16 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.139 # 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 0.52 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker-Nonius Apex II CCD' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.48720 _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 'Model taken from ambient pressure structure' _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_ambient_pressure 6000000 _diffrn_reflns_number 11243 _reflns_number_total 1022 _diffrn_reflns_av_R_equivalents 0.097 # Number of reflections with Friedels Law is 1183 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1270 _diffrn_reflns_theta_min 2.216 _diffrn_reflns_theta_max 17.768 _diffrn_measured_fraction_theta_max 0.801 _diffrn_reflns_theta_full 13.326 _diffrn_measured_fraction_theta_full 0.839 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _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 0.20 _refine_ls_number_reflns 1022 _refine_ls_number_restraints 2 _refine_ls_number_parameters 115 #_refine_ls_R_factor_ref 0.0717 _refine_ls_wR_factor_ref 0.1113 _refine_ls_goodness_of_fit_ref 0.9001 #_reflns_number_all 1022 _refine_ls_R_factor_all 0.0717 _refine_ls_wR_factor_all 0.1113 # 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 693 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_gt 0.0890 _refine_ls_shift/su_max 0.000193 # 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: 50.4 71.5 39.7 12.8 3.69 ; _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: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.33 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.84 022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.89 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced and as such the quality of the model is lower. 413_ALERT_2_B Short Inter XH3 .. XHn H9 .. H623 .. 2.04 Ang. 432_ALERT_2_B Short Inter X...Y Contact O5 .. C7 .. 2.90 Ang. 432_ALERT_2_B Short Inter X...Y Contact C4 .. C6 .. 3.05 Ang. 432_ALERT_2_B Short Inter X...Y Contact C5 .. C7 .. 2.97 Ang. 432_ALERT_2_B Short Inter X...Y Contact C5 .. C8 .. 3.08 Ang. 432_ALERT_2_C Short Inter X...Y Contact O1 .. C3 .. 2.97 Ang. 432_ALERT_2_C Short Inter X...Y Contact N2 .. C7 .. 3.02 Ang. 432_ALERT_2_C Short Inter X...Y Contact C4 .. C8 .. 3.16 Ang. These short intermolecular contacts are simply due to the closing up of the voids between the molecules because of the application of hydrostatic pressure. 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 #------------------------------------------------------------------------------- 14.10 0.500 0.837 646 541 105 15.54 0.550 0.830 859 713 146 17.00 0.600 0.809 1120 906 214 #----------------------------------------------------------- ACTA Min. Res. ---- 17.77 0.626 0.802 1275 1022 253 ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 O1 O 0.48836(17) -0.0297(4) 0.68217(12) 0.0277 1.0000 Uani D . . . . . N2 N 0.52925(19) 0.0984(4) 0.61806(14) 0.0209 1.0000 Uani . . . . . . C3 C 0.5659(2) 0.2543(5) 0.64997(16) 0.0224 1.0000 Uani . . . . . . C4 C 0.6035(2) 0.4034(5) 0.58774(16) 0.0193 1.0000 Uani . . . . . . C5 C 0.6124(2) 0.3641(5) 0.49537(16) 0.0190 1.0000 Uani . . . . . . O5 O 0.59544(16) 0.1865(4) 0.46054(12) 0.0216 1.0000 Uani D . . . . . C6 C 0.6424(2) 0.5109(5) 0.43592(16) 0.0198 1.0000 Uani . . . . . . O61 O 0.64688(16) 0.4534(4) 0.34692(11) 0.0257 1.0000 Uani . . . . . . C62 C 0.7020(2) 0.5858(6) 0.28781(17) 0.0295 1.0000 Uani . . . . . . C7 C 0.6641(2) 0.6936(5) 0.46729(17) 0.0221 1.0000 Uani . . . . . . C8 C 0.6570(2) 0.7306(5) 0.55951(18) 0.0227 1.0000 Uani . . . . . . C9 C 0.6257(2) 0.5880(5) 0.61874(17) 0.0235 1.0000 Uani . . . . . . H1 H 0.460(3) -0.120(6) 0.646(2) 0.0414 1.0000 Uiso D . . . . . H3 H 0.5668 0.2770 0.7133 0.0273 1.0000 Uiso R . . . . . H5 H 0.577(3) 0.113(6) 0.499(2) 0.0330 1.0000 Uiso D . . . . . H621 H 0.7050 0.5255 0.2287 0.0434 1.0000 Uiso R . . . . . H622 H 0.7760 0.6101 0.3091 0.0435 1.0000 Uiso R . . . . . H623 H 0.6602 0.7035 0.2843 0.0443 1.0000 Uiso R . . . . . H7 H 0.6840 0.7920 0.4269 0.0266 1.0000 Uiso R . . . . . H8 H 0.6731 0.8555 0.5796 0.0265 1.0000 Uiso R . . . . . H9 H 0.6195 0.6160 0.6802 0.0283 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 0.0390(12) 0.0283(19) 0.0157(9) 0.0029(8) 0.0040(8) -0.0102(10) N2 0.0242(12) 0.0189(19) 0.0194(10) 0.0022(10) 0.0027(8) 0.0005(10) C3 0.0264(14) 0.023(2) 0.0179(12) -0.0029(11) 0.0015(10) 0.0025(12) C4 0.0144(12) 0.025(2) 0.0186(11) -0.0022(11) -0.0004(9) 0.0003(10) C5 0.0151(13) 0.020(2) 0.0217(12) -0.0033(11) -0.0021(9) 0.0016(10) O5 0.0279(10) 0.0194(16) 0.0173(9) -0.0004(8) -0.0007(7) -0.0028(8) C6 0.0166(13) 0.025(2) 0.0174(11) -0.0007(11) -0.0002(9) 0.0021(11) O61 0.0326(11) 0.0289(17) 0.0157(9) 0.0003(8) 0.0018(7) -0.0046(9) C62 0.0299(16) 0.039(3) 0.0199(12) 0.0062(13) 0.0006(10) -0.0054(14) C7 0.0173(13) 0.024(2) 0.0255(13) 0.0038(12) 0.0010(10) 0.0000(11) C8 0.0172(13) 0.020(2) 0.0310(14) -0.0062(12) -0.0003(10) -0.0012(11) C9 0.0208(14) 0.029(2) 0.0209(12) -0.0055(12) 0.0016(10) 0.0023(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.017(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 . 1.388(3) yes O1 . H1 . 0.89(3) no N2 . C3 . 1.257(4) yes C3 . C4 . 1.454(4) yes C3 . H3 . 0.949 no C4 . C5 . 1.395(3) yes C4 . C9 . 1.383(4) yes C5 . O5 . 1.348(4) yes C5 . C6 . 1.391(4) yes O5 . H5 . 0.79(3) no C6 . O61 . 1.375(3) yes C6 . C7 . 1.371(4) yes O61 . C62 . 1.430(4) yes C62 . H621 . 0.968 no C62 . H622 . 0.962 no C62 . H623 . 0.959 no C7 . C8 . 1.389(4) yes C7 . H7 . 0.937 no C8 . C9 . 1.372(4) yes C8 . H8 . 0.934 no C9 . H9 . 0.931 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 . 114.7(2) yes N2 . C3 . C4 . 118.8(2) yes N2 . C3 . H3 . 121.0 no C4 . C3 . H3 . 120.1 no C3 . C4 . C5 . 120.3(3) yes C3 . C4 . C9 . 120.4(2) yes C5 . C4 . C9 . 119.2(3) yes C4 . C5 . O5 . 122.6(3) yes C4 . C5 . C6 . 119.7(3) yes O5 . C5 . C6 . 117.7(2) yes C5 . O5 . H5 . 111(3) no C5 . C6 . O61 . 113.7(3) yes C5 . C6 . C7 . 120.6(2) yes O61 . C6 . C7 . 125.6(3) yes C6 . O61 . C62 . 114.6(3) yes O61 . C62 . H621 . 107.0 no O61 . C62 . H622 . 110.2 no H621 . C62 . H622 . 109.6 no O61 . C62 . H623 . 109.4 no H621 . C62 . H623 . 109.7 no H622 . C62 . H623 . 110.9 no C6 . C7 . C8 . 119.3(3) yes C6 . C7 . H7 . 120.3 no C8 . C7 . H7 . 120.4 no C7 . C8 . C9 . 120.6(3) yes C7 . C8 . H8 . 118.0 no C9 . C8 . H8 . 121.3 no C4 . C9 . C8 . 120.4(3) yes C4 . C9 . H9 . 120.0 no C8 . C9 . H9 . 119.6 no