# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ; The crystal structures of the low-temperature and high-pressure polymorphs of nitric acid ; _publ_contact_author_name 'David Allan' _publ_contact_author_email D.R.ALLAN@ED.AC.UK loop_ _publ_author_name 'David Allan' D.J.Francis W.G.Marshall I.D.H.Oswald C.R.Pulham C.K.Spanswick # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 754934' #TrackingRef '1.cif' _audit_creation_date 06-09-07 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'cp6003 in P2(1)/c' _chemical_name_systematic 'Nitric acid' _chemical_melting_point 231 _cell_length_a 6.3689(3) _cell_length_b 8.6046(4) _cell_length_c 16.4141(9) _cell_angle_alpha 90 _cell_angle_beta 90.055(4) _cell_angle_gamma 90 _cell_volume 899.52(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _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 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' 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' 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 16 # Given Formula = H1 N1 O3 # Dc = 1.86 Fooo = 512.00 Mu = 2.09 M = 252.05 # Found Formula = H1 N1 O3 # Dc = 1.86 FOOO = 512.00 Mu = 2.09 M = 252.05 _chemical_formula_sum 'H1 N1 O3' _chemical_formula_moiety 'H1 N1 O3' _chemical_compound_source ? _chemical_formula_weight 63.01 _cell_measurement_reflns_used 5370 _cell_measurement_theta_min 5 _cell_measurement_theta_max 58 _cell_measurement_temperature 210 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_min 0.48 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_max 4.00 _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.209 # Sheldrick geometric approximatio 0.90 0.90 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.90 _diffrn_measurement_device_type 'Bruker SMART' _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 210 _diffrn_reflns_number 16407 _reflns_number_total 2545 _diffrn_reflns_av_R_equivalents 0.067 # Number of reflections with Friedels Law is 2545 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2620 _diffrn_reflns_theta_min 2.482 _diffrn_reflns_theta_max 29.985 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.786 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 3.11 _oxford_diffrn_Wilson_scale 5.36 _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 0.24 _refine_ls_number_reflns 2538 _refine_ls_number_restraints 7 _refine_ls_number_parameters 161 #_refine_ls_R_factor_ref 0.0532 _refine_ls_wR_factor_ref 0.1166 _refine_ls_goodness_of_fit_ref 1.1800 #_reflns_number_all 2538 _refine_ls_R_factor_all 0.0532 _refine_ls_wR_factor_all 0.1166 # 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 1636 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_gt 0.0987 _refine_ls_shift/su_max 0.000330 # 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 refxyz # 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: 8.73 12.1 3.83 ; # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # 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 N1 N 0.4823(2) 0.57899(11) 0.74389(8) 0.0337 1.0000 Uani . . . . . . O11 O 0.6071(3) 0.57429(16) 0.79805(10) 0.0475 1.0000 Uani . . . . . . O21 O 0.3985(2) 0.70022(14) 0.71704(8) 0.0430 1.0000 Uani . . . . . . O31 O 0.4199(2) 0.45059(17) 0.70694(9) 0.0400 1.0000 Uani D . . . . . H31 H 0.489(4) 0.382(2) 0.7334(12) 0.0500 1.0000 Uiso D . . . . . N2 N 0.0159(2) 0.42559(13) 0.61469(8) 0.0322 1.0000 Uani . . . . . . O12 O -0.1082(3) 0.41815(16) 0.66896(10) 0.0461 1.0000 Uani . . . . . . O22 O 0.0873(2) 0.54270(16) 0.58382(8) 0.0415 1.0000 Uani . . . . . . O32 O 0.0907(2) 0.29161(17) 0.58221(9) 0.0440 1.0000 Uani D . . . . . H32 H 0.032(4) 0.223(2) 0.6117(12) 0.0500 1.0000 Uiso D . . . . . N3 N 0.0146(2) 0.07847(13) 0.36896(9) 0.0338 1.0000 Uani . . . . . . O13 O -0.1050(2) 0.09047(17) 0.42423(9) 0.0480 1.0000 Uani . . . . . . O23 O 0.0875(2) -0.04085(15) 0.34044(9) 0.0427 1.0000 Uani . . . . . . O33 O 0.0806(2) 0.20894(15) 0.33063(9) 0.0429 1.0000 Uani D . . . . . H33 H 0.024(4) 0.281(2) 0.3596(13) 0.0500 1.0000 Uiso D . . . . . N4 N 0.4857(2) 0.25122(14) 0.49189(9) 0.0349 1.0000 Uani D . . . . . O14 O 0.6026(2) 0.25279(17) 0.54855(9) 0.0459 1.0000 Uani . . . . . . O24 O 0.4200(2) 0.37545(16) 0.45656(8) 0.0424 1.0000 Uani D . . . . . O34 O 0.4139(2) 0.12523(17) 0.46010(10) 0.0469 1.0000 Uani D . . . . . H24 H 0.477(6) 0.458(2) 0.481(2) 0.0500 0.5000 Uiso D . . . . . H34 H 0.480(6) 0.047(2) 0.481(2) 0.0500 0.5000 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 0.0324(7) 0.0329(7) 0.0359(6) -0.0017(4) 0.0026(6) -0.0005(4) O11 0.0525(8) 0.0453(8) 0.0447(7) -0.0050(5) -0.0114(7) 0.0049(5) O21 0.0499(7) 0.0263(6) 0.0528(6) 0.0006(5) -0.0054(6) 0.0032(5) O31 0.0442(7) 0.0261(5) 0.0497(6) -0.0019(5) -0.0068(6) 0.0000(5) N2 0.0332(7) 0.0270(6) 0.0363(6) -0.0018(4) -0.0055(5) 0.0012(5) O12 0.0466(8) 0.0478(8) 0.0437(6) -0.0048(5) 0.0102(6) 0.0031(6) O22 0.0503(8) 0.0289(5) 0.0453(6) 0.0025(5) -0.0025(6) -0.0029(6) O32 0.0491(8) 0.0255(5) 0.0576(7) -0.0029(5) 0.0159(6) 0.0011(6) N3 0.0338(6) 0.0274(6) 0.0402(6) -0.0005(4) -0.0053(6) -0.0004(5) O13 0.0480(9) 0.0476(8) 0.0484(6) -0.0013(5) 0.0116(7) -0.0004(6) O23 0.0445(7) 0.0265(6) 0.0573(7) -0.0028(5) 0.0084(6) 0.0034(6) O33 0.0525(8) 0.0264(5) 0.0497(6) 0.0020(5) 0.0046(6) 0.0013(6) N4 0.0319(6) 0.0339(6) 0.0389(6) -0.0023(4) 0.0027(6) 0.0000(6) O14 0.0487(7) 0.0434(8) 0.0456(6) -0.0024(5) -0.0090(7) 0.0004(6) O24 0.0511(7) 0.0296(6) 0.0466(6) 0.0036(5) -0.0002(6) -0.0012(6) O34 0.0476(8) 0.0284(6) 0.0646(8) -0.0048(6) -0.0127(7) 0.0005(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.653(2) loop_ _oxford_twin_element_scale_factors 0.483(3) 0.517(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 . O11 . 1.193(2) yes N1 . O21 . 1.2518(16) yes N1 . O31 . 1.3213(17) yes O31 . H31 . 0.858(16) no N2 . O12 . 1.193(2) yes N2 . O22 . 1.2163(18) yes N2 . O32 . 1.3568(18) yes O32 . H32 . 0.851(16) no N3 . O13 . 1.189(2) yes N3 . O23 . 1.2205(16) yes N3 . O33 . 1.3541(17) yes O33 . H33 . 0.858(16) no N4 . O14 . 1.191(2) yes N4 . O24 . 1.2858(18) yes N4 . O34 . 1.287(2) yes O24 . H24 . 0.887(18) no O34 . H34 . 0.864(18) 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 O11 . N1 . O21 . 125.05(13) yes O11 . N1 . O31 . 120.92(12) yes O21 . N1 . O31 . 114.03(15) yes N1 . O31 . H31 . 101.0(17) no O12 . N2 . O22 . 127.13(14) yes O12 . N2 . O32 . 118.75(13) yes O22 . N2 . O32 . 114.12(14) yes N2 . O32 . H32 . 102.3(16) no O13 . N3 . O23 . 127.58(14) yes O13 . N3 . O33 . 118.80(13) yes O23 . N3 . O33 . 113.62(14) yes N3 . O33 . H33 . 102.2(15) no O14 . N4 . O24 . 123.06(15) yes O14 . N4 . O34 . 123.22(15) yes O24 . N4 . O34 . 113.71(14) yes N4 . O24 . H24 . 109.3(10) no N4 . O34 . H34 . 108.4(10) no # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 754935' #TrackingRef '2.cif' _audit_creation_date 06-09-07 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'cp6003_150 in P2(1)/c' _chemical_name_systematic 'Nitric acid' _chemical_melting_point 231 _cell_length_a 6.3031(2) _cell_length_b 8.5847(2) _cell_length_c 16.3122(4) _cell_angle_alpha 90 _cell_angle_beta 90.039(2) _cell_angle_gamma 90 _cell_volume 882.66(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _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 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' 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' 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 16 # Given Formula = H1 N1 O3 # Dc = 1.90 Fooo = 512.00 Mu = 2.13 M = 252.05 # Found Formula = H1 N1 O3 # Dc = 1.90 FOOO = 512.00 Mu = 2.13 M = 252.05 _chemical_formula_sum 'H1 N1 O3' _chemical_formula_moiety 'H1 N1 O3' _chemical_compound_source ? _chemical_formula_weight 63.01 _cell_measurement_reflns_used 5370 _cell_measurement_theta_min 5 _cell_measurement_theta_max 58 _cell_measurement_temperature 150 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_min 0.48 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_max 4.00 _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.213 # Sheldrick geometric approximatio 0.90 0.90 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.43 _exptl_absorpt_correction_T_max 0.90 _diffrn_measurement_device_type 'Bruker SMART' _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 150 _diffrn_reflns_number 24325 _reflns_number_total 3500 _diffrn_reflns_av_R_equivalents 0.062 # Number of reflections with Friedels Law is 3500 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3675 _diffrn_reflns_theta_min 2.497 _diffrn_reflns_theta_max 34.257 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 31.173 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 3.11 _oxford_diffrn_Wilson_scale 5.36 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.25 _refine_diff_density_max 0.35 _refine_ls_number_reflns 3493 _refine_ls_number_restraints 7 _refine_ls_number_parameters 161 #_refine_ls_R_factor_ref 0.0489 _refine_ls_wR_factor_ref 0.0880 _refine_ls_goodness_of_fit_ref 0.8515 #_reflns_number_all 3493 _refine_ls_R_factor_all 0.0489 _refine_ls_wR_factor_all 0.0880 # 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 2442 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_gt 0.0812 _refine_ls_shift/su_max 0.001280 # 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 refxyz # 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 ; # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # 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 N1 N 0.48115(17) 0.58204(10) 0.74390(6) 0.0218 1.0000 Uani . . . . . . O11 O 0.60744(18) 0.57245(10) 0.79907(6) 0.0319 1.0000 Uani . . . . . . O21 O 0.39964(16) 0.70009(10) 0.71716(6) 0.0290 1.0000 Uani . . . . . . O31 O 0.41865(16) 0.45035(10) 0.70560(6) 0.0266 1.0000 Uani D . . . . . H31 H 0.487(3) 0.381(2) 0.7289(10) 0.0500 1.0000 Uiso D . . . . . N2 N 0.01576(18) 0.42553(10) 0.61486(6) 0.0212 1.0000 Uani . . . . . . O12 O -0.10924(17) 0.41789(10) 0.66972(6) 0.0302 1.0000 Uani . . . . . . O22 O 0.08754(18) 0.54354(11) 0.58335(6) 0.0271 1.0000 Uani . . . . . . O32 O 0.09143(17) 0.29104(12) 0.58198(6) 0.0293 1.0000 Uani D . . . . . H32 H 0.013(3) 0.2258(19) 0.6098(9) 0.0500 1.0000 Uiso D . . . . . N3 N 0.01438(18) 0.07849(11) 0.36857(6) 0.0224 1.0000 Uani . . . . . . O13 O -0.10713(19) 0.08997(10) 0.42487(6) 0.0322 1.0000 Uani . . . . . . O23 O 0.08832(17) -0.04111(11) 0.34003(6) 0.0289 1.0000 Uani . . . . . . O33 O 0.08053(17) 0.20977(11) 0.33046(6) 0.0291 1.0000 Uani D . . . . . H33 H 0.015(3) 0.2784(19) 0.3585(9) 0.0500 1.0000 Uiso D . . . . . N4 N 0.48603(17) 0.25154(12) 0.49160(6) 0.0250 1.0000 Uani D . . . . . O14 O 0.60412(17) 0.25252(12) 0.54924(6) 0.0312 1.0000 Uani . . . . . . O24 O 0.42022(18) 0.37591(11) 0.45608(6) 0.0286 1.0000 Uani D . . . . . O34 O 0.41378(18) 0.12493(11) 0.45978(7) 0.0320 1.0000 Uani D . . . . . H24 H 0.479(5) 0.4552(19) 0.4798(16) 0.0500 0.5000 Uiso D . . . . . H34 H 0.477(5) 0.0488(18) 0.4826(18) 0.0500 0.5000 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 0.0219(5) 0.0191(5) 0.0246(4) -0.0026(3) 0.0031(5) -0.0005(3) O11 0.0328(6) 0.0323(5) 0.0306(5) -0.0043(4) -0.0081(5) 0.0024(4) O21 0.0334(5) 0.0162(4) 0.0374(5) 0.0006(3) -0.0043(4) 0.0020(4) O31 0.0298(5) 0.0158(3) 0.0342(4) -0.0020(3) -0.0064(5) -0.0002(4) N2 0.0207(5) 0.0193(4) 0.0235(4) -0.0012(3) -0.0030(4) 0.0017(5) O12 0.0304(6) 0.0321(5) 0.0280(4) -0.0019(4) 0.0063(4) 0.0003(5) O22 0.0308(5) 0.0204(4) 0.0301(4) 0.0014(3) -0.0024(4) -0.0005(5) O32 0.0310(5) 0.0183(4) 0.0385(5) -0.0019(4) 0.0100(5) 0.0016(5) N3 0.0216(5) 0.0190(4) 0.0266(5) 0.0004(3) -0.0019(4) -0.0004(5) O13 0.0329(6) 0.0303(5) 0.0334(5) -0.0018(4) 0.0072(5) -0.0001(5) O23 0.0296(5) 0.0188(4) 0.0382(5) -0.0020(4) 0.0058(4) 0.0032(5) O33 0.0355(5) 0.0175(4) 0.0342(5) 0.0011(4) 0.0026(4) 0.0015(5) N4 0.0219(5) 0.0258(5) 0.0274(5) -0.0021(4) 0.0029(5) -0.0008(5) O14 0.0312(5) 0.0316(5) 0.0309(5) -0.0025(4) -0.0069(5) 0.0009(6) O24 0.0342(5) 0.0194(4) 0.0322(4) 0.0023(4) -0.0011(4) 0.0001(6) O34 0.0321(5) 0.0184(4) 0.0454(5) -0.0033(4) -0.0098(5) 0.0004(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6594(14) loop_ _oxford_twin_element_scale_factors 0.4775(15) 0.5225(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 N1 . O11 . 1.2039(14) yes N1 . O21 . 1.2170(12) yes N1 . O31 . 1.3503(12) yes O31 . H31 . 0.830(14) no N2 . O12 . 1.1945(14) yes N2 . O22 . 1.2229(13) yes N2 . O32 . 1.3596(13) yes O32 . H32 . 0.875(14) no N3 . O13 . 1.2003(14) yes N3 . O23 . 1.2200(13) yes N3 . O33 . 1.3531(13) yes O33 . H33 . 0.853(14) no N4 . O14 . 1.1987(13) yes N4 . O24 . 1.2835(13) yes N4 . O34 . 1.2876(14) yes O24 . H24 . 0.865(17) no O34 . H34 . 0.850(17) 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 O11 . N1 . O21 . 127.13(10) yes O11 . N1 . O31 . 118.77(9) yes O21 . N1 . O31 . 114.10(11) yes N1 . O31 . H31 . 103.8(13) no O12 . N2 . O22 . 127.21(10) yes O12 . N2 . O32 . 118.73(10) yes O22 . N2 . O32 . 114.05(10) yes N2 . O32 . H32 . 98.0(11) no O13 . N3 . O23 . 127.24(10) yes O13 . N3 . O33 . 118.69(10) yes O23 . N3 . O33 . 114.06(10) yes N3 . O33 . H33 . 100.4(11) no O14 . N4 . O24 . 123.27(11) yes O14 . N4 . O34 . 122.77(11) yes O24 . N4 . O34 . 113.96(10) yes N4 . O24 . H24 . 108.4(9) no N4 . O34 . H34 . 107.9(9) no # Attachment '3.cif' #TrackingRef '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 754936' #TrackingRef '3.cif' _audit_creation_date 09-05-08 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 'nitr01 in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ _cell_length_a 7.3163(4) _cell_length_b 8.4176(11) _cell_length_c 7.3135(11) _cell_angle_alpha 90 _cell_angle_beta 116.895(6) _cell_angle_gamma 90 _cell_volume 401.69(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 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 = H0.50 N0.50 O1.50 # Dc = 1.04 Fooo = 256.00 Mu = 1.17 M = 63.01 # Found Formula = H1 N1 O3 # Dc = 2.08 FOOO = 256.00 Mu = 2.34 M = 126.03 _chemical_formula_sum 'H1 N1 O3' _chemical_formula_moiety 'H1 N1 O3' _chemical_compound_source ? _chemical_formula_weight 63.01 _cell_measurement_reflns_used 1083 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26 _cell_measurement_temperature 293 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 2.084 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.234 # Sheldrick geometric approximatio 0.95 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.42 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 1505 _reflns_number_total 310 _diffrn_reflns_av_R_equivalents 0.0253 # Number of reflections with Friedels Law is 310 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 812 _diffrn_reflns_theta_min 3.951 _diffrn_reflns_theta_max 26.297 _diffrn_measured_fraction_theta_max 0.381 _diffrn_reflns_theta_full 25.245 _diffrn_measured_fraction_theta_full 0.398 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _reflns_limit_h_min -9 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 6 _oxford_diffrn_Wilson_B_factor 3.26 _oxford_diffrn_Wilson_scale 0.84 _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 0.25 # 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>2.0\s(I) _refine_ls_number_reflns 276 _refine_ls_number_restraints 60 _refine_ls_number_parameters 80 _oxford_refine_ls_R_factor_ref 0.0773 _refine_ls_wR_factor_ref 0.0790 _refine_ls_goodness_of_fit_ref 1.0256 _refine_ls_shift/su_max 0.000057 # The values computed from all data _oxford_reflns_number_all 303 _refine_ls_R_factor_all 0.0889 _refine_ls_wR_factor_all 0.1381 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 276 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_gt 0.0790 # 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 F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refxyz # 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: 0.856 0.668 -0.501E-01 ; # 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. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.7850(10) 0.7329(11) 0.7685(9) 0.0308 1.0000 Uani . U . . . . . O11 O 0.6053(9) 0.7351(9) 0.7218(8) 0.0424 1.0000 Uani . U . . . . . O21 O 0.8967(9) 0.6170(9) 0.8093(9) 0.0420 1.0000 Uani . U . . . . . O31 O 0.8824(10) 0.8711(11) 0.7830(9) 0.0432 1.0000 Uani D U . . . . . H31 H 0.790(13) 0.936(12) 0.753(3) 0.0531 1.0000 Uiso D . . . . . . N2 N 0.2619(9) 0.9267(9) 0.7827(12) 0.0277 1.0000 Uani . U . . . . . O12 O 0.2090(9) 0.9207(8) 0.6021(12) 0.0416 1.0000 Uani . U . . . . . O22 O 0.2781(9) 1.0492(9) 0.8813(11) 0.0421 1.0000 Uani . U . . . . . O32 O 0.3113(9) 0.7909(10) 0.8868(12) 0.0380 1.0000 Uani D U . . . . . H32 H 0.305(5) 0.704(6) 0.834(15) 0.0500 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 0.032(4) 0.034(5) 0.029(4) 0.004(3) 0.015(4) 0.0009(18) O11 0.029(4) 0.055(7) 0.039(6) 0.002(3) 0.012(4) -0.003(2) O21 0.042(4) 0.029(5) 0.056(5) -0.003(3) 0.023(4) 0.000(2) O31 0.034(3) 0.030(4) 0.065(6) 0.000(3) 0.022(4) 0.001(2) N2 0.032(4) 0.014(5) 0.043(4) -0.0004(18) 0.023(4) -0.002(2) O12 0.048(5) 0.034(7) 0.041(4) 0.000(2) 0.019(4) 0.002(3) O22 0.058(5) 0.017(5) 0.057(6) -0.003(3) 0.031(4) 0.008(3) O32 0.052(4) 0.015(5) 0.051(5) 0.002(2) 0.026(3) 0.001(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.014(9) loop_ _oxford_twin_element_scale_factors 0.614(14) 0.386(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 N1 . O11 . 1.200(8) yes N1 . O21 . 1.220(10) yes N1 . O31 . 1.343(11) yes O31 . H31 . 0.820(9) no N2 . O12 . 1.198(9) yes N2 . O22 . 1.233(10) yes N2 . O32 . 1.330(9) yes O32 . H32 . 0.820(9) 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 O11 . N1 . O21 . 127.5(9) yes O11 . N1 . O31 . 118.9(7) yes O21 . N1 . O31 . 113.6(7) yes N1 . O31 . H31 . 100(10) no O12 . N2 . O22 . 125.3(7) yes O12 . N2 . O32 . 117.6(7) yes O22 . N2 . O32 . 117.1(8) yes N2 . O32 . H32 . 124(8) no