# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Simon Parsons' 'Russell D. L. Johnstone' 'Alistair Lennie' 'Stewart F. Parker' 'Elna Pidcock' 'Patricia R. Richardson' 'John E. Warren' 'Peter A. Wood' _publ_contact_author_name 'Simon Parsons' _publ_contact_author_email S.PARSONS@ED.AC.UK _publ_section_title ; High-Pressure Polymorphism in Salicylamide ; # Attachment 'all.cif' data_ambient_I.cif _database_code_depnum_ccdc_archive 'CCDC 751100' _oxford_structure_analysis_title 'sp7081 in I2/a' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.8887(8) _cell_length_b 4.9700(3) _cell_length_c 20.9607(19) _cell_angle_alpha 90 _cell_angle_beta 91.546(4) _cell_angle_gamma 90 _cell_volume 1342.19(17) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 1 2/a 1 ' _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 0.0033 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 H7 N1 O2 # Dc = 1.36 Fooo = 576.00 Mu = 1.01 M = 137.14 # Found Formula = C7 H7 N1 O2 # Dc = 1.36 FOOO = 576.00 Mu = 1.01 M = 137.14 _chemical_formula_sum 'C7 H7 N1 O2' _chemical_formula_moiety 'C7 H7 N1 O2' _chemical_compound_source ? _chemical_formula_weight 137.14 _cell_measurement_reflns_used 2947 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.32 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_max 0.57 _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.101 # Sheldrick geometric approximatio 0.96 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _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 293 _diffrn_reflns_number 9399 _reflns_number_total 1778 _diffrn_reflns_av_r_equivalents 0.0370 # Number of reflections with Friedels Law is 1778 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1890 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.944 _diffrn_reflns_theta_max 29.614 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.133 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 2.77 _oxford_diffrn_Wilson_scale 0.39 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.31 _refine_diff_density_max 0.34 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 1778 _refine_ls_number_restraints 1 _refine_ls_number_parameters 95 _oxford_refine_ls_R_factor_ref 0.0947 _refine_ls_wR_factor_ref 0.1382 _refine_ls_goodness_of_fit_ref 1.0989 _refine_ls_shift/su_max 0.000202 # The values computed from all data _oxford_reflns_number_all 1778 _refine_ls_R_factor_all 0.0947 _refine_ls_wR_factor_all 0.1382 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1434 _refine_ls_R_factor_gt 0.0751 _refine_ls_wR_factor_gt 0.1313 # 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^) + ( 0.02P)^2^ + 2.68P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_exptl_refinement ; Checkcif Output: 129_ALERT_4_A Unusual Space-group Specified .................. I12/A1 120_ALERT_1_C Reported SPGR I12/a1 Inconsistent with Explicit I2/A 128_ALERT_4_C Non-standard setting of Space-group C2/c .... I2/a The space group is correct. 912_ALERT_4_B # Missing FCF Reflections Above STh/L= 0.600 111 The data collection strategy used aimed to achieve a complete data set to 2\q = 53 deg. Some higher angle data were collected in the process and these have been included in the refinement. #============================================================================== Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 20.82 0.500 1.000 702 702 0 23.01 0.550 1.000 938 938 0 25.24 0.600 1.000 1210 1210 0 #----------------------------------------------------------- ACTA Min. Res. --- 27.51 0.650 1.000 1551 1551 0 29.61 0.695 0.941 1889 1778 111 061_ALERT_4_C Tmax/Tmin Range Test RR' too Large ............. 0.87 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. 731_ALERT_1_C Bond Calc 0.85(3), Rep 0.846(10) ...... 3.00 su-Ra O2 -H7 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. 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at 293 K. 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1 No action taken. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., 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. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.56161(13) 0.7308(4) 0.55066(9) 0.0389 1.0000 Uani . . . . . . . O1 O 0.39320(11) 0.8299(3) 0.53705(8) 0.0432 1.0000 Uani . . . . . . . O2 O 0.25281(12) 0.5741(4) 0.59183(10) 0.0557 1.0000 Uani D . . . . . . C1 C 0.32922(16) 0.4321(5) 0.62175(11) 0.0390 1.0000 Uani . . . . . . . C2 C 0.43478(15) 0.4781(4) 0.60997(10) 0.0324 1.0000 Uani . . . . . . . C3 C 0.50768(16) 0.3213(5) 0.64293(11) 0.0401 1.0000 Uani . . . . . . . C4 C 0.47929(19) 0.1287(5) 0.68582(12) 0.0467 1.0000 Uani . . . . . . . C5 C 0.3753(2) 0.0860(5) 0.69661(12) 0.0514 1.0000 Uani . . . . . . . C6 C 0.30107(18) 0.2368(5) 0.66501(12) 0.0494 1.0000 Uani . . . . . . . C7 C 0.46246(15) 0.6895(4) 0.56348(10) 0.0324 1.0000 Uani . . . . . . . H1 H 0.5793 0.3485 0.6355 0.0482 1.0000 Uiso . . . . . . . H2 H 0.5307 0.0253 0.7080 0.0560 1.0000 Uiso . . . . . . . H3 H 0.3551 -0.0483 0.7260 0.0619 1.0000 Uiso . . . . . . . H4 H 0.2298 0.2068 0.6729 0.0595 1.0000 Uiso . . . . . . . H5 H 0.5787 0.8572 0.5235 0.0585 1.0000 Uiso . . . . . . . H6 H 0.6102 0.6316 0.5693 0.0585 1.0000 Uiso . . . . . . . H7 H 0.286(2) 0.682(5) 0.5684(12) 0.068(9) 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 N1 0.0314(9) 0.0399(11) 0.0457(10) 0.0044(9) 0.0054(7) -0.0008(8) O1 0.0330(8) 0.0423(9) 0.0546(10) 0.0091(8) 0.0035(7) 0.0030(7) O2 0.0287(8) 0.0621(12) 0.0765(13) 0.0194(10) 0.0044(8) -0.0038(8) C1 0.0336(11) 0.0386(12) 0.0449(12) -0.0030(10) 0.0051(9) -0.0031(10) C2 0.0331(10) 0.0301(11) 0.0341(11) -0.0059(9) 0.0043(8) -0.0038(9) C3 0.0367(11) 0.0395(13) 0.0442(12) -0.0015(10) 0.0026(9) -0.0001(10) C4 0.0547(14) 0.0410(13) 0.0444(13) 0.0040(11) 0.0002(11) 0.0034(12) C5 0.0658(16) 0.0434(14) 0.0455(14) 0.0064(11) 0.0130(12) -0.0072(13) C6 0.0431(12) 0.0515(15) 0.0542(14) 0.0031(12) 0.0134(11) -0.0103(12) C7 0.0320(10) 0.0301(10) 0.0353(10) -0.0062(9) 0.0026(8) -0.0014(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.765(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 N1 . C7 . 1.329(2) yes N1 . H5 . 0.880 no N1 . H6 . 0.880 no O1 . C7 . 1.251(2) yes O2 . C1 . 1.352(3) yes O2 . H7 . 0.846(10) no C1 . C2 . 1.408(3) yes C1 . C6 . 1.384(3) yes C2 . C3 . 1.390(3) yes C2 . C7 . 1.483(3) yes C3 . C4 . 1.370(3) yes C3 . H1 . 0.950 no C4 . C5 . 1.381(4) yes C4 . H2 . 0.950 no C5 . C6 . 1.372(4) yes C5 . H3 . 0.950 no C6 . H4 . 0.950 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 C7 . N1 . H5 . 120.0 no C7 . N1 . H6 . 120.0 no H5 . N1 . H6 . 120.0 no C1 . O2 . H7 . 103.4(20) no O2 . C1 . C2 . 122.0(2) yes O2 . C1 . C6 . 118.0(2) yes C2 . C1 . C6 . 120.0(2) yes C1 . C2 . C3 . 117.7(2) yes C1 . C2 . C7 . 118.74(19) yes C3 . C2 . C7 . 123.53(18) yes C2 . C3 . C4 . 121.9(2) yes C2 . C3 . H1 . 119.0 no C4 . C3 . H1 . 119.0 no C3 . C4 . C5 . 119.5(2) yes C3 . C4 . H2 . 120.3 no C5 . C4 . H2 . 120.3 no C4 . C5 . C6 . 120.3(2) yes C4 . C5 . H3 . 119.9 no C6 . C5 . H3 . 119.9 no C1 . C6 . C5 . 120.5(2) yes C1 . C6 . H4 . 119.7 no C5 . C6 . H4 . 119.7 no C2 . C7 . N1 . 119.46(18) yes C2 . C7 . O1 . 120.32(18) yes N1 . C7 . O1 . 120.2(2) yes _chemical_name_common Salicylamide _exptl_crystal_recrystallization_method 'From MeOH/EtOH' #edit data_0_3GPa_I.cif _database_code_depnum_ccdc_archive 'CCDC 751101' _oxford_structure_analysis_title 'sala01 in I2/a' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.7925(11) _cell_length_b 4.9356(5) _cell_length_c 20.415(5) _cell_angle_alpha 90 _cell_angle_beta 92.266(14) _cell_angle_gamma 90 _cell_volume 1288.0(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 1 2/a 1 ' _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 0.0010 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 8 # Given Formula = C7 H7 N1 O2 # Dc = 1.41 Fooo = 576.00 Mu = 1.05 M = 137.14 # Found Formula = C7 H7 N1 O2 # Dc = 1.41 FOOO = 576.00 Mu = 1.05 M = 137.14 _chemical_formula_sum 'C7 H7 N1 O2' _chemical_formula_moiety 'C7 H7 N1 O2' _chemical_compound_source ? _chemical_formula_weight 137.14 _cell_measurement_reflns_used 780 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.105 # 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 0.86 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type ' synchrotron ' _diffrn_radiation_wavelength 0.47540 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _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 293 _diffrn_ambient_pressure 300000 _diffrn_reflns_number 4875 _reflns_number_total 814 _diffrn_reflns_av_R_equivalents 0.0837 # Number of reflections with Friedels Law is 814 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1960 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 2.959 _diffrn_reflns_theta_max 19.830 _diffrn_measured_fraction_theta_max 0.417 _diffrn_reflns_theta_full 15.269 _diffrn_measured_fraction_theta_full 0.493 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -18 _reflns_limit_h_max 18 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _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 -0.36 _refine_diff_density_max 0.37 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 812 _refine_ls_number_restraints 114 _refine_ls_number_parameters 95 _oxford_refine_ls_R_factor_ref 0.1055 _refine_ls_wR_factor_ref 0.1282 _refine_ls_goodness_of_fit_ref 0.9885 _refine_ls_shift/su_max 0.000178 # The values computed from all data _oxford_reflns_number_all 812 _refine_ls_R_factor_all 0.1055 _refine_ls_wR_factor_all 0.1282 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 520 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_gt 0.1065 # 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^) + ( 0.04P)^2^ + 1.43P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_exptl_refinement ; Checkcif Output: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 15.27 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.49 911_ALERT_3_B # Missing FCF Refl Between THmin & STh/L= 0.600 258 088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.55 910_ALERT_3_C # Missing FCF Reflections Below Th(Min) ........ 6 912_ALERT_4_C # Missing FCF Reflections Above STh/L= 0.600 98 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 129_ALERT_4_A Unusual Space-group Specified .................. I12/A1 120_ALERT_1_C Reported SPGR I12/a1 Inconsistent with Explicit I2/A 128_ALERT_4_C Non-standard setting of Space-group C2/c .... I2/a The space group is correct 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at 293 K 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 114 No action taken ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., 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. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.56146(13) 0.7288(4) 0.5515(2) 0.0432 1.0000 Uani D U . . . . . O1 O 0.39144(11) 0.8308(3) 0.53649(18) 0.0445 1.0000 Uani D U . . . . . O2 O 0.25066(11) 0.5793(4) 0.59330(19) 0.0569 1.0000 Uani D U . . . . . C1 C 0.32746(14) 0.4293(4) 0.6233(2) 0.0388 1.0000 Uani D U . . . . . C2 C 0.43386(13) 0.4726(4) 0.6108(2) 0.0336 1.0000 Uani D U . . . . . C3 C 0.50717(15) 0.3080(5) 0.6437(3) 0.0402 1.0000 Uani D U . . . . . C4 C 0.47825(18) 0.1119(5) 0.6867(3) 0.0468 1.0000 Uani D U . . . . . C5 C 0.37360(19) 0.0729(5) 0.6979(3) 0.0447 1.0000 Uani D U . . . . . C6 C 0.29888(16) 0.2302(5) 0.6661(3) 0.0458 1.0000 Uani D U . . . . . C7 C 0.46147(14) 0.6869(4) 0.5640(2) 0.0344 1.0000 Uani D U . . . . . H1 H 0.5793 0.3327 0.6360 0.0484 1.0000 Uiso . . . . . . . H2 H 0.5299 0.0031 0.7086 0.0563 1.0000 Uiso . . . . . . . H3 H 0.3532 -0.0632 0.7278 0.0542 1.0000 Uiso . . . . . . . H4 H 0.2270 0.2011 0.6738 0.0555 1.0000 Uiso . . . . . . . H5 H 0.5785 0.8571 0.5239 0.0650 1.0000 Uiso . . . . . . . H6 H 0.6105 0.6284 0.5707 0.0650 1.0000 Uiso . . . . . . . H7 H 0.282(2) 0.691(3) 0.5697(7) 0.0684(19) 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 N1 0.0269(8) 0.0370(11) 0.066(7) 0.0051(17) 0.0032(13) -0.0014(7) O1 0.0294(7) 0.0384(10) 0.066(5) 0.0073(14) 0.0009(11) 0.0015(6) O2 0.0248(7) 0.0540(12) 0.092(6) 0.0125(16) 0.0011(12) -0.0011(7) C1 0.0287(9) 0.0358(13) 0.052(6) -0.0018(17) 0.0028(14) -0.0022(8) C2 0.0274(8) 0.0281(12) 0.045(6) -0.0061(16) 0.0017(13) -0.0021(7) C3 0.0308(9) 0.0360(13) 0.053(6) -0.0018(18) -0.0025(15) -0.0002(8) C4 0.0455(11) 0.0369(14) 0.058(7) 0.002(2) -0.001(2) 0.0026(10) C5 0.0537(13) 0.0389(14) 0.042(8) 0.004(2) 0.0118(19) -0.0066(10) C6 0.0362(10) 0.0485(16) 0.054(7) 0.000(2) 0.0113(16) -0.0085(10) C7 0.0285(9) 0.0297(11) 0.045(6) -0.0052(16) 0.0022(14) -0.0009(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 5.6(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 N1 . C7 . 1.331(2) yes N1 . H5 . 0.880 no N1 . H6 . 0.880 no O1 . C7 . 1.258(3) yes O2 . C1 . 1.357(3) yes O2 . H7 . 0.842(9) no C1 . C2 . 1.411(3) yes C1 . C6 . 1.375(4) yes C2 . C3 . 1.393(4) yes C2 . C7 . 1.477(4) yes C3 . C4 . 1.367(5) yes C3 . H1 . 0.950 no C4 . C5 . 1.381(3) yes C4 . H2 . 0.950 no C5 . C6 . 1.374(4) yes C5 . H3 . 0.950 no C6 . H4 . 0.950 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 C7 . N1 . H5 . 120.0 no C7 . N1 . H6 . 120.0 no H5 . N1 . H6 . 120.0 no C1 . O2 . H7 . 105(2) no O2 . C1 . C2 . 121.5(2) yes O2 . C1 . C6 . 118.11(18) yes C2 . C1 . C6 . 120.38(19) yes C1 . C2 . C3 . 117.4(2) yes C1 . C2 . C7 . 118.82(18) yes C3 . C2 . C7 . 123.76(17) yes C2 . C3 . C4 . 121.88(18) yes C2 . C3 . H1 . 119.0 no C4 . C3 . H1 . 119.1 no C3 . C4 . C5 . 119.6(2) yes C3 . C4 . H2 . 120.1 no C5 . C4 . H2 . 120.2 no C4 . C5 . C6 . 120.2(3) yes C4 . C5 . H3 . 119.9 no C6 . C5 . H3 . 119.9 no C1 . C6 . C5 . 120.46(18) yes C1 . C6 . H4 . 119.8 no C5 . C6 . H4 . 119.7 no C2 . C7 . N1 . 119.5(2) yes C2 . C7 . O1 . 120.58(17) yes N1 . C7 . O1 . 119.9(2) yes _chemical_name_common Salicylamide _exptl_crystal_recrystallization_method 'From MeOH/EtOH' # edit data_2_0GPa_I.cif _database_code_depnum_ccdc_archive 'CCDC 751102' _oxford_structure_analysis_title 'sala02 in I2/a' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.5438(6) _cell_length_b 4.8464(3) _cell_length_c 19.203(3) _cell_angle_alpha 90 _cell_angle_beta 93.648(7) _cell_angle_gamma 90 _cell_volume 1165.0(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 1 2/a 1 ' _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 0.0010 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 8 # Given Formula = C7 H7 N1 O2 # Dc = 1.56 Fooo = 576.00 Mu = 1.16 M = 137.14 # Found Formula = C7 H7 N1 O2 # Dc = 1.56 FOOO = 576.00 Mu = 1.16 M = 137.14 _chemical_formula_sum 'C7 H7 N1 O2' _chemical_formula_moiety 'C7 H7 N1 O2' _chemical_compound_source ? _chemical_formula_weight 137.14 _cell_measurement_reflns_used 956 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.116 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47540 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _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 293 _diffrn_ambient_pressure 2000000 _diffrn_reflns_number 4594 _reflns_number_total 753 _diffrn_reflns_av_R_equivalents 0.0618 # Number of reflections with Friedels Law is 753 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1776 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 3.015 _diffrn_reflns_theta_max 19.841 _diffrn_measured_fraction_theta_max 0.427 _diffrn_reflns_theta_full 14.881 _diffrn_measured_fraction_theta_full 0.503 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _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 0.27 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 751 _refine_ls_number_restraints 114 _refine_ls_number_parameters 95 _oxford_refine_ls_R_factor_ref 0.0675 _refine_ls_wR_factor_ref 0.1099 _refine_ls_goodness_of_fit_ref 0.9987 _refine_ls_shift/su_max 0.000158 # The values computed from all data _oxford_reflns_number_all 751 _refine_ls_R_factor_all 0.0675 _refine_ls_wR_factor_all 0.1099 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 564 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_gt 0.1023 # 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^) + ( 0.04P)^2^ + 1.10P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_exptl_refinement ; Checkcif Output: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.88 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.50 088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.91 911_ALERT_3_B # Missing FCF Refl Between THmin & STh/L= 0.600 297 912_ALERT_4_B # Missing FCF Reflections Above STh/L= 0.600 141 910_ALERT_3_C # Missing FCF Reflections Below Th(Min) ........ 6 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 129_ALERT_4_A Unusual Space-group Specified .................. I12/A1 120_ALERT_1_C Reported SPGR I12/a1 Inconsistent with Explicit I2/A 128_ALERT_4_C Non-standard setting of Space-group C2/c .... I2/a The space group is correct. 432_ALERT_2_B Short Inter X...Y Contact C4 .. C7 .. 3.06 Ang. 432_ALERT_2_C Short Inter X...Y Contact N1 .. C7 .. 2.99 Ang. Short contacts are expected at high pressure 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at 293 K 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 114 No action taken ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., 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. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.56081(11) 0.7263(3) 0.55263(18) 0.0254 1.0000 Uani D U . . . . . O1 O 0.38671(10) 0.8294(3) 0.53470(15) 0.0283 1.0000 Uani D U . . . . . O2 O 0.24537(9) 0.5845(3) 0.59580(16) 0.0339 1.0000 Uani D U . . . . . C1 C 0.32266(12) 0.4195(4) 0.62518(19) 0.0221 1.0000 Uani D U . . . . . C2 C 0.43093(12) 0.4577(3) 0.61169(18) 0.0190 1.0000 Uani D U . . . . . C3 C 0.50613(13) 0.2815(4) 0.6450(2) 0.0229 1.0000 Uani D U . . . . . C4 C 0.47653(14) 0.0759(4) 0.6889(2) 0.0272 1.0000 Uani D U . . . . . C5 C 0.36903(16) 0.0396(4) 0.7009(2) 0.0290 1.0000 Uani D U . . . . . C6 C 0.29300(14) 0.2098(4) 0.6689(2) 0.0272 1.0000 Uani D U . . . . . C7 C 0.45867(12) 0.6818(3) 0.56395(18) 0.0184 1.0000 Uani D U . . . . . H1 H 0.5796 0.3047 0.6371 0.0276 1.0000 Uiso . . . . . . . H2 H 0.5291 -0.0413 0.7111 0.0327 1.0000 Uiso . . . . . . . H3 H 0.3482 -0.1029 0.7312 0.0353 1.0000 Uiso . . . . . . . H4 H 0.2197 0.1833 0.6768 0.0329 1.0000 Uiso . . . . . . . H5 H 0.5783 0.8600 0.5245 0.0382 1.0000 Uiso . . . . . . . H6 H 0.6109 0.6221 0.5733 0.0382 1.0000 Uiso . . . . . . . H7 H 0.278(2) 0.696(3) 0.5705(7) 0.0678(18) 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 N1 0.0196(6) 0.0228(8) 0.034(5) 0.0052(11) 0.0040(12) -0.0003(5) O1 0.0210(6) 0.0249(7) 0.039(4) 0.0058(9) 0.0026(9) 0.0016(5) O2 0.0176(6) 0.0331(8) 0.051(4) 0.0091(11) 0.0032(9) -0.0003(5) C1 0.0198(7) 0.0240(9) 0.023(5) -0.0043(12) 0.0019(12) -0.0023(6) C2 0.0199(7) 0.0189(8) 0.019(4) -0.0044(11) 0.0034(11) -0.0012(6) C3 0.0218(7) 0.0234(10) 0.024(5) -0.0016(12) 0.0037(12) 0.0001(6) C4 0.0306(8) 0.0215(9) 0.030(5) 0.0022(13) 0.0032(15) 0.0023(7) C5 0.0350(9) 0.0246(10) 0.028(6) -0.0005(13) 0.0084(14) -0.0054(7) C6 0.0247(8) 0.0300(11) 0.028(5) -0.0030(13) 0.0074(13) -0.0073(6) C7 0.0214(7) 0.0194(8) 0.015(4) -0.0067(11) 0.0026(11) -0.0008(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.37(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 N1 . C7 . 1.331(2) yes N1 . H5 . 0.880 no N1 . H6 . 0.880 no O1 . C7 . 1.256(3) yes O2 . C1 . 1.352(3) yes O2 . H7 . 0.847(9) no C1 . C2 . 1.411(2) yes C1 . C6 . 1.384(4) yes C2 . C3 . 1.397(3) yes C2 . C7 . 1.477(3) yes C3 . C4 . 1.372(4) yes C3 . H1 . 0.950 no C4 . C5 . 1.393(3) yes C4 . H2 . 0.950 no C5 . C6 . 1.376(4) yes C5 . H3 . 0.950 no C6 . H4 . 0.950 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 C7 . N1 . H5 . 120.0 no C7 . N1 . H6 . 120.0 no H5 . N1 . H6 . 120.0 no C1 . O2 . H7 . 105(2) no O2 . C1 . C2 . 121.28(18) yes O2 . C1 . C6 . 118.29(14) yes C2 . C1 . C6 . 120.44(17) yes C1 . C2 . C3 . 117.76(18) yes C1 . C2 . C7 . 118.54(16) yes C3 . C2 . C7 . 123.70(14) yes C2 . C3 . C4 . 121.62(14) yes C2 . C3 . H1 . 119.2 no C4 . C3 . H1 . 119.2 no C3 . C4 . C5 . 119.7(2) yes C3 . C4 . H2 . 120.1 no C5 . C4 . H2 . 120.1 no C4 . C5 . C6 . 120.1(2) yes C4 . C5 . H3 . 120.0 no C6 . C5 . H3 . 120.0 no C1 . C6 . C5 . 120.39(15) yes C1 . C6 . H4 . 119.8 no C5 . C6 . H4 . 119.8 no C2 . C7 . N1 . 119.20(18) yes C2 . C7 . O1 . 120.36(13) yes N1 . C7 . O1 . 120.4(2) yes _chemical_name_common Salicylamide _exptl_crystal_recrystallization_method 'From MeOH/EtOH' #edit data_4_0GPa_I.cif _database_code_depnum_ccdc_archive 'CCDC 751103' _oxford_structure_analysis_title 'sala03 in I2/a' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.3706(7) _cell_length_b 4.7918(3) _cell_length_c 18.398(3) _cell_angle_alpha 90 _cell_angle_beta 94.078(8) _cell_angle_gamma 90 _cell_volume 1087.8(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 1 2/a 1 ' _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 0.0010 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 8 # Given Formula = C7 H7 N1 O2 # Dc = 1.67 Fooo = 576.00 Mu = 1.25 M = 137.14 # Found Formula = C7 H7 N1 O2 # Dc = 1.67 FOOO = 576.00 Mu = 1.25 M = 137.14 _chemical_formula_sum 'C7 H7 N1 O2' _chemical_formula_moiety 'C7 H7 N1 O2' _chemical_compound_source ? _chemical_formula_weight 137.14 _cell_measurement_reflns_used 971 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.125 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47540 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _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 293 _diffrn_ambient_pressure 4000000 _diffrn_reflns_number 4172 _reflns_number_total 721 _diffrn_reflns_av_R_equivalents 0.0581 # Number of reflections with Friedels Law is 721 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1658 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 3.050 _diffrn_reflns_theta_max 19.840 _diffrn_measured_fraction_theta_max 0.435 _diffrn_reflns_theta_full 15.078 _diffrn_measured_fraction_theta_full 0.492 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _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 -0.31 _refine_diff_density_max 0.31 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 720 _refine_ls_number_restraints 114 _refine_ls_number_parameters 95 _oxford_refine_ls_R_factor_ref 0.0722 _refine_ls_wR_factor_ref 0.1193 _refine_ls_goodness_of_fit_ref 0.9982 _refine_ls_shift/su_max 0.000123 # The values computed from all data _oxford_reflns_number_all 720 _refine_ls_R_factor_all 0.0722 _refine_ls_wR_factor_all 0.1193 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 542 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_gt 0.1116 # 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^) + ( 0.05P)^2^ + 1.83P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_exptl_refinement ; Checkcif Output: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 15.08 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.49 088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.58 911_ALERT_3_B # Missing FCF Refl Between THmin & STh/L= 0.600 272 910_ALERT_3_C # Missing FCF Reflections Below Th(Min) ........ 6 912_ALERT_4_C # Missing FCF Reflections Above STh/L= 0.600 100 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 129_ALERT_4_A Unusual Space-group Specified .................. I12/A1 120_ALERT_1_C Reported SPGR I12/a1 Inconsistent with Explicit I2/A 128_ALERT_4_C Non-standard setting of Space-group C2/c .... I2/a The space group is correct 432_ALERT_2_B Short Inter X...Y Contact N1 .. C7 .. 2.87 Ang. 432_ALERT_2_B Short Inter X...Y Contact C4 .. C7 .. 2.96 Ang. 432_ALERT_2_C Short Inter X...Y Contact C7 .. C7 .. 3.12 Ang. Short contacts are expected at high pressure. 731_ALERT_1_C Bond Calc 0.84(2), Rep 0.843(9) ...... 2.22 su-Ra O2 -H7 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. 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at 293 K 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 114 No action taken ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., 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. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.55971(14) 0.7262(3) 0.5526(2) 0.0193 1.0000 Uani D U . . . . . O1 O 0.38309(12) 0.8270(3) 0.53325(19) 0.0235 1.0000 Uani D U . . . . . O2 O 0.24174(11) 0.5831(3) 0.59777(19) 0.0299 1.0000 Uani D U . . . . . C1 C 0.31915(15) 0.4097(4) 0.6260(2) 0.0196 1.0000 Uani D U . . . . . C2 C 0.42875(14) 0.4469(4) 0.6120(2) 0.0178 1.0000 Uani D U . . . . . C3 C 0.50513(16) 0.2653(4) 0.6451(3) 0.0215 1.0000 Uani D U . . . . . C4 C 0.47532(17) 0.0539(4) 0.6904(3) 0.0227 1.0000 Uani D U . . . . . C5 C 0.36613(19) 0.0170(4) 0.7025(3) 0.0240 1.0000 Uani D U . . . . . C6 C 0.28889(17) 0.1922(4) 0.6703(3) 0.0223 1.0000 Uani D U . . . . . C7 C 0.45665(15) 0.6773(4) 0.5628(2) 0.0175 1.0000 Uani D U . . . . . H1 H 0.5794 0.2881 0.6364 0.0264 1.0000 Uiso . . . . . . . H2 H 0.5286 -0.0657 0.7132 0.0292 1.0000 Uiso . . . . . . . H3 H 0.3449 -0.1307 0.7326 0.0267 1.0000 Uiso . . . . . . . H4 H 0.2148 0.1656 0.6787 0.0258 1.0000 Uiso . . . . . . . H5 H 0.5775 0.8655 0.5247 0.0277 1.0000 Uiso . . . . . . . H6 H 0.6105 0.6189 0.5737 0.0277 1.0000 Uiso . . . . . . . H7 H 0.274(3) 0.694(4) 0.5710(8) 0.0675(19) 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 N1 0.0175(7) 0.0168(8) 0.024(6) 0.0015(11) 0.0021(15) -0.0004(6) O1 0.0191(7) 0.0196(7) 0.031(4) 0.0035(9) -0.0002(12) 0.0012(5) O2 0.0151(7) 0.0250(8) 0.049(5) 0.0076(10) 0.0019(13) 0.0005(5) C1 0.0163(8) 0.0190(9) 0.024(5) -0.0019(12) 0.0032(15) 0.0001(7) C2 0.0167(8) 0.0155(8) 0.021(5) -0.0029(11) 0.0025(14) -0.0027(6) C3 0.0171(8) 0.0190(9) 0.029(5) 0.0010(13) 0.0045(15) 0.0004(7) C4 0.0248(9) 0.0167(9) 0.027(5) 0.0000(12) 0.0035(17) 0.0005(8) C5 0.0280(10) 0.0187(9) 0.026(6) 0.0001(13) 0.0060(17) -0.0050(7) C6 0.0214(9) 0.0226(10) 0.023(5) -0.0036(12) 0.0048(16) -0.0052(7) C7 0.0180(8) 0.0138(8) 0.021(5) -0.0025(12) 0.0013(14) 0.0003(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.27(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 N1 . C7 . 1.323(2) yes N1 . H5 . 0.880 no N1 . H6 . 0.880 no O1 . C7 . 1.252(3) yes O2 . C1 . 1.344(3) yes O2 . H7 . 0.843(9) no C1 . C2 . 1.409(2) yes C1 . C6 . 1.391(4) yes C2 . C3 . 1.392(4) yes C2 . C7 . 1.484(3) yes C3 . C4 . 1.377(4) yes C3 . H1 . 0.950 no C4 . C5 . 1.396(3) yes C4 . H2 . 0.949 no C5 . C6 . 1.374(4) yes C5 . H3 . 0.948 no C6 . H4 . 0.950 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 C7 . N1 . H5 . 120.0 no C7 . N1 . H6 . 119.9 no H5 . N1 . H6 . 120.0 no C1 . O2 . H7 . 105(3) no O2 . C1 . C2 . 121.34(19) yes O2 . C1 . C6 . 118.39(16) yes C2 . C1 . C6 . 120.26(18) yes C1 . C2 . C3 . 118.25(19) yes C1 . C2 . C7 . 118.26(18) yes C3 . C2 . C7 . 123.49(16) yes C2 . C3 . C4 . 121.41(16) yes C2 . C3 . H1 . 119.2 no C4 . C3 . H1 . 119.4 no C3 . C4 . C5 . 119.6(2) yes C3 . C4 . H2 . 120.2 no C5 . C4 . H2 . 120.2 no C4 . C5 . C6 . 120.3(2) yes C4 . C5 . H3 . 120.0 no C6 . C5 . H3 . 119.7 no C1 . C6 . C5 . 120.17(17) yes C1 . C6 . H4 . 120.0 no C5 . C6 . H4 . 119.8 no C2 . C7 . N1 . 119.1(2) yes C2 . C7 . O1 . 119.86(16) yes N1 . C7 . O1 . 121.0(2) yes _chemical_name_common Salicylamide _exptl_crystal_recrystallization_method 'From MeOH/EtOH' #edit data_5_1GPa_I.cif _database_code_depnum_ccdc_archive 'CCDC 751104' _oxford_structure_analysis_title 'sala04 in I2/a' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.2791(7) _cell_length_b 4.7643(3) _cell_length_c 17.9649(17) _cell_angle_alpha 90 _cell_angle_beta 93.960(4) _cell_angle_gamma 90 _cell_volume 1048.46(13) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 1 2/a 1 ' _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 0.0016 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 0.0010 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 8 # Given Formula = C7 H7 N1 O2 # Dc = 1.74 Fooo = 576.00 Mu = 1.29 M = 137.14 # Found Formula = C7 H7 N1 O2 # Dc = 1.74 FOOO = 576.00 Mu = 1.29 M = 137.14 _chemical_formula_sum 'C7 H7 N1 O2' _chemical_formula_moiety 'C7 H7 N1 O2' _chemical_compound_source ? _chemical_formula_weight 137.14 _cell_measurement_reflns_used 1238 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.129 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47540 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _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 293 _diffrn_ambient_pressure 5100000 _diffrn_reflns_number 3937 _reflns_number_total 695 _diffrn_reflns_av_R_equivalents 0.0590 # Number of reflections with Friedels Law is 695 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1602 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 3.069 _diffrn_reflns_theta_max 19.858 _diffrn_measured_fraction_theta_max 0.433 _diffrn_reflns_theta_full 15.092 _diffrn_measured_fraction_theta_full 0.511 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _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 0.27 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 692 _refine_ls_number_restraints 114 _refine_ls_number_parameters 95 _oxford_refine_ls_R_factor_ref 0.0657 _refine_ls_wR_factor_ref 0.1239 _refine_ls_goodness_of_fit_ref 1.0462 _refine_ls_shift/su_max 0.000126 # The values computed from all data _oxford_reflns_number_all 692 _refine_ls_R_factor_all 0.0657 _refine_ls_wR_factor_all 0.1239 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 566 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_gt 0.1161 # 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^ + 1.15P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_exptl_refinement ; Checkcif Output: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 15.09 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.51 432_ALERT_2_A Short Inter X...Y Contact C4 .. C7 .. 2.88 Ang. 088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.28 911_ALERT_3_B # Missing FCF Refl Between THmin & STh/L= 0.600 299 912_ALERT_4_B # Missing FCF Reflections Above STh/L= 0.600 145 910_ALERT_3_C # Missing FCF Reflections Below Th(Min) ........ 6 The high pressure cell causes shading of a significant proportion of the sphere of reflections. This means that the completeness is reduced. 120_ALERT_1_C Reported SPGR I12/a1 Inconsistent with Explicit I2/A 128_ALERT_4_C Non-standard setting of Space-group C2/c .... I2/a 129_ALERT_4_A Unusual Space-group Specified .................. I12/A1 The space group is correct. 432_ALERT_2_B Short Inter X...Y Contact N1 .. C7 .. 2.83 Ang. 432_ALERT_2_B Short Inter X...Y Contact C7 .. C7 .. 3.07 Ang. 432_ALERT_2_C Short Inter X...Y Contact C3 .. C7 .. 3.18 Ang. 432_ALERT_2_C Short Inter X...Y Contact C6 .. C6 .. 3.11 Ang. Short contacts are expected at high pressure. 731_ALERT_1_C Bond Calc 0.85(2), Rep 0.848(9) ...... 2.22 su-Ra O2 -H7 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. 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at 293 K. 222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.40 Ratio 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 114 No action taken. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., 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. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.55924(13) 0.7266(3) 0.5530(2) 0.0147 1.0000 Uani D U . . . . . O1 O 0.38107(11) 0.8249(3) 0.53225(18) 0.0225 1.0000 Uani D U . . . . . O2 O 0.23967(10) 0.5807(3) 0.59881(18) 0.0244 1.0000 Uani D U . . . . . C1 C 0.31755(14) 0.4021(4) 0.6268(2) 0.0158 1.0000 Uani D U . . . . . C2 C 0.42767(13) 0.4417(4) 0.6121(2) 0.0139 1.0000 Uani D U . . . . . C3 C 0.50459(14) 0.2570(4) 0.6448(3) 0.0168 1.0000 Uani D U . . . . . C4 C 0.47481(15) 0.0426(4) 0.6906(2) 0.0166 1.0000 Uani D U . . . . . C5 C 0.36511(16) 0.0043(4) 0.7036(2) 0.0194 1.0000 Uani D U . . . . . C6 C 0.28706(15) 0.1817(4) 0.6711(3) 0.0194 1.0000 Uani D U . . . . . C7 C 0.45560(14) 0.6751(4) 0.5630(2) 0.0133 1.0000 Uani D U . . . . . H1 H 0.5793 0.2793 0.6354 0.0202 1.0000 Uiso . . . . . . . H2 H 0.5288 -0.0788 0.7132 0.0200 1.0000 Uiso . . . . . . . H3 H 0.3442 -0.1444 0.7348 0.0235 1.0000 Uiso . . . . . . . H4 H 0.2122 0.1529 0.6791 0.0236 1.0000 Uiso . . . . . . . H5 H 0.5770 0.8674 0.5245 0.0222 1.0000 Uiso . . . . . . . H6 H 0.6106 0.6202 0.5749 0.0222 1.0000 Uiso . . . . . . . H7 H 0.271(3) 0.694(4) 0.5711(8) 0.0680(19) 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 N1 0.0154(7) 0.0154(8) 0.014(5) -0.0004(11) 0.0027(12) 0.0001(5) O1 0.0167(6) 0.0170(7) 0.034(4) 0.0028(9) 0.0017(10) 0.0013(5) O2 0.0128(6) 0.0221(8) 0.038(4) 0.0074(10) 0.0016(11) 0.0007(5) C1 0.0137(7) 0.0165(9) 0.017(5) -0.0048(11) 0.0008(13) 0.0004(6) C2 0.0145(7) 0.0136(9) 0.014(4) -0.0032(11) 0.0028(12) -0.0019(6) C3 0.0157(7) 0.0156(9) 0.019(5) 0.0004(12) 0.0033(13) -0.0006(6) C4 0.0203(8) 0.0168(9) 0.013(5) -0.0003(12) 0.0021(14) 0.0013(6) C5 0.0234(9) 0.0167(10) 0.019(5) -0.0001(12) 0.0050(13) -0.0054(6) C6 0.0173(8) 0.0207(10) 0.021(5) -0.0029(12) 0.0058(13) -0.0042(6) C7 0.0159(8) 0.0135(9) 0.011(4) -0.0044(11) 0.0003(12) -0.0008(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.4(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 N1 . C7 . 1.321(2) yes N1 . H5 . 0.880 no N1 . H6 . 0.880 no O1 . C7 . 1.258(3) yes O2 . C1 . 1.351(3) yes O2 . H7 . 0.848(9) no C1 . C2 . 1.408(2) yes C1 . C6 . 1.385(4) yes C2 . C3 . 1.391(3) yes C2 . C7 . 1.474(3) yes C3 . C4 . 1.377(4) yes C3 . H1 . 0.950 no C4 . C5 . 1.395(3) yes C4 . H2 . 0.950 no C5 . C6 . 1.377(4) yes C5 . H3 . 0.950 no C6 . H4 . 0.950 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 C7 . N1 . H5 . 120.0 no C7 . N1 . H6 . 120.0 no H5 . N1 . H6 . 120.0 no C1 . O2 . H7 . 106(3) no O2 . C1 . C2 . 120.66(19) yes O2 . C1 . C6 . 118.62(16) yes C2 . C1 . C6 . 120.72(18) yes C1 . C2 . C3 . 117.93(19) yes C1 . C2 . C7 . 118.65(17) yes C3 . C2 . C7 . 123.42(15) yes C2 . C3 . C4 . 121.42(15) yes C2 . C3 . H1 . 119.3 no C4 . C3 . H1 . 119.3 no C3 . C4 . C5 . 119.8(2) yes C3 . C4 . H2 . 120.1 no C5 . C4 . H2 . 120.1 no C4 . C5 . C6 . 120.1(2) yes C4 . C5 . H3 . 120.0 no C6 . C5 . H3 . 120.0 no C1 . C6 . C5 . 120.07(16) yes C1 . C6 . H4 . 120.0 no C5 . C6 . H4 . 119.9 no C2 . C7 . N1 . 119.19(19) yes C2 . C7 . O1 . 119.91(15) yes N1 . C7 . O1 . 120.9(2) yes _chemical_name_common Salicylamide _exptl_crystal_recrystallization_method 'From MeOH/EtOH' #edit data_0_2GPa_II.cif _database_code_depnum_ccdc_archive 'CCDC 751105' _oxford_structure_analysis_title 'sali01 in P212121' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 3.8938(4) _cell_length_b 5.5612(6) _cell_length_c 28.566(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 618.6(2) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-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 0.0010 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 = C7 H7 N1 O2 # Dc = 1.47 Fooo = 288.00 Mu = 1.10 M = 137.14 # Found Formula = C7 H7 N1 O2 # Dc = 1.47 FOOO = 288.00 Mu = 1.10 M = 137.14 _chemical_formula_sum 'C7 H7 N1 O2' _chemical_formula_moiety 'C7 H7 N1 O2' _chemical_compound_source ? _chemical_formula_weight 137.14 _cell_measurement_reflns_used 587 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.110 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type ' synchrotron ' _diffrn_radiation_wavelength 0.47540 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _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 293 _diffrn_ambient_pressure 200000 _diffrn_reflns_number 10956 _reflns_number_total 720 _diffrn_reflns_av_R_equivalents 0.1486 # Number of reflections with Friedels Law is 720 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 632 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 2.496 _diffrn_reflns_theta_max 17.277 _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 14.858 _diffrn_measured_fraction_theta_full 0.913 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 33 _reflns_limit_h_min 0 _reflns_limit_h_max 4 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 33 _oxford_diffrn_Wilson_B_factor 2.99 _oxford_diffrn_Wilson_scale 0.21 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.30 _refine_diff_density_max 0.27 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 716 _refine_ls_number_restraints 8 _refine_ls_number_parameters 95 _oxford_refine_ls_R_factor_ref 0.0932 _refine_ls_wR_factor_ref 0.1261 _refine_ls_goodness_of_fit_ref 1.0518 _refine_ls_shift/su_max 0.000112 # The values computed from all data _oxford_reflns_number_all 716 _refine_ls_R_factor_all 0.0932 _refine_ls_wR_factor_all 0.1261 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 434 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_gt 0.1062 # 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 unk _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^) + ( 0.07P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_exptl_refinement ; Checkcif Output: 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.86 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91 911_ALERT_3_B # Missing FCF Refl Between THmin & STh/L= 0.600 61 022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.54 910_ALERT_3_C # Missing FCF Reflections Below Th(Min) ........ 2 912_ALERT_4_C # Missing FCF Reflections Above STh/L= 0.600 3 340_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. 731_ALERT_1_C Bond Calc 0.85(3), Rep 0.847(10) ...... 3.00 su-Ra O2 -H7 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. 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at 293 K 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 8 No action taken ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., 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. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.4602(9) 0.2729(5) 0.30161(14) 0.0468 1.0000 Uani . . . . . . . O1 O 0.1943(7) 0.6177(5) 0.28282(12) 0.0490 1.0000 Uani . . . . . . . O2 O -0.1123(7) 0.8717(5) 0.34323(13) 0.0484 1.0000 Uani D . . . . . . C1 C -0.0145(9) 0.7051(6) 0.37539(18) 0.0352 1.0000 Uani . . . . . . . C2 C 0.1700(8) 0.4979(6) 0.36249(17) 0.0323 1.0000 Uani . . . . . . . C3 C 0.2500(9) 0.3339(6) 0.39776(18) 0.0394 1.0000 Uani . . . . . . . C4 C 0.1557(10) 0.3726(7) 0.44348(19) 0.0434 1.0000 Uani . . . . . . . C5 C -0.0185(11) 0.5811(7) 0.45530(18) 0.0437 1.0000 Uani . . . . . . . C6 C -0.1022(9) 0.7459(7) 0.42178(18) 0.0420 1.0000 Uani . . . . . . . C7 C 0.2747(8) 0.4652(6) 0.31358(18) 0.0349 1.0000 Uani . . . . . . . H1 H 0.3742 0.1919 0.3901 0.0474 1.0000 Uiso . . . . . . . H2 H 0.2106 0.2576 0.4669 0.0515 1.0000 Uiso . . . . . . . H3 H -0.0804 0.6092 0.4869 0.0515 1.0000 Uiso . . . . . . . H4 H -0.2225 0.8875 0.4303 0.0509 1.0000 Uiso . . . . . . . H5 H 0.5234 0.2531 0.2724 0.0693 1.0000 Uiso . . . . . . . H6 H 0.5161 0.1661 0.3230 0.0693 1.0000 Uiso . . . . . . . H7 H -0.031(5) 0.822(7) 0.3175(9) 0.068(2) 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 N1 0.0580(19) 0.0417(19) 0.041(3) -0.0019(19) 0.009(2) 0.0092(17) O1 0.0630(18) 0.0506(17) 0.034(3) 0.0123(15) 0.0077(16) 0.0072(15) O2 0.0611(17) 0.0414(16) 0.043(3) 0.0101(16) 0.0061(16) 0.0126(13) C1 0.0352(17) 0.0298(19) 0.041(4) 0.005(2) -0.003(2) -0.0011(16) C2 0.0311(15) 0.0297(17) 0.036(3) 0.0019(19) 0.0015(18) -0.0043(14) C3 0.042(2) 0.0352(19) 0.041(4) 0.004(2) 0.001(2) 0.0049(18) C4 0.049(2) 0.044(2) 0.038(4) 0.005(2) -0.002(2) -0.0027(19) C5 0.046(2) 0.052(2) 0.033(3) -0.004(2) 0.007(2) -0.005(2) C6 0.045(2) 0.033(2) 0.047(4) -0.005(2) 0.008(2) 0.0017(17) C7 0.0338(18) 0.0348(19) 0.036(3) -0.001(2) 0.0012(18) -0.0039(16) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.31(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C7 . 1.335(5) yes N1 . H5 . 0.877 no N1 . H6 . 0.879 no O1 . C7 . 1.261(5) yes O2 . C1 . 1.359(5) yes O2 . H7 . 0.847(10) no C1 . C2 . 1.407(5) yes C1 . C6 . 1.387(7) yes C2 . C3 . 1.395(6) yes C2 . C7 . 1.467(6) yes C3 . C4 . 1.374(7) yes C3 . H1 . 0.952 no C4 . C5 . 1.385(6) yes C4 . H2 . 0.949 no C5 . C6 . 1.365(6) yes C5 . H3 . 0.948 no C6 . H4 . 0.948 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 C7 . N1 . H5 . 119.8 no C7 . N1 . H6 . 119.8 no H5 . N1 . H6 . 120.4 no C1 . O2 . H7 . 105(3) no O2 . C1 . C2 . 121.6(4) yes O2 . C1 . C6 . 117.7(4) yes C2 . C1 . C6 . 120.7(4) yes C1 . C2 . C3 . 117.4(4) yes C1 . C2 . C7 . 119.6(4) yes C3 . C2 . C7 . 123.0(3) yes C2 . C3 . C4 . 121.7(4) yes C2 . C3 . H1 . 119.3 no C4 . C3 . H1 . 119.1 no C3 . C4 . C5 . 119.6(4) yes C3 . C4 . H2 . 120.2 no C5 . C4 . H2 . 120.2 no C4 . C5 . C6 . 120.5(5) yes C4 . C5 . H3 . 119.7 no C6 . C5 . H3 . 119.8 no C1 . C6 . C5 . 120.1(4) yes C1 . C6 . H4 . 120.2 no C5 . C6 . H4 . 119.7 no C2 . C7 . N1 . 119.6(4) yes C2 . C7 . O1 . 120.8(3) yes N1 . C7 . O1 . 119.6(4) yes _chemical_name_common Salicylamide _exptl_crystal_recrystallization_method 'From MeOH/EtOH'