Supplementary Material (ESI) for CrystEngComm This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal CrystEngComm loop_ _publ_author_name C.R.Pulham 'David Robert Allan' 'Francesca P. A. Fabbiani' S.Parsons _publ_contact_author_name C.R.Pulham _publ_contact_author_address ; Department of Chemistry The University of Edinburgh West Mains Road Edinburgh SCOTLAND EH9 3JJ ; _publ_contact_author_email C.R.PULHAM@ED.AC.UK _publ_section_title ; An exploration of the polymorphism of piracetam using high pressure ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Siemens Industrial Automation, Inc (1993) SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; data_CRYSTALS_cif_1 _database_code_depnum_ccdc_archive 'CCDC 258689' _audit_creation_date 04-11-10 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'pirh2o in P-1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.9376(2) _cell_length_b 7.4450(2) _cell_length_c 9.1267(2) _cell_angle_alpha 97.732(2) _cell_angle_beta 103.958(2) _cell_angle_gamma 115.766(2) _cell_volume 396.24(2) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 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 2 # Given Formula = C6 H12 N2 O3 # Dc = 1.34 Fooo = 172.00 Mu = 1.08 M = 160.17 # Found Formula = C6 H12 N2 O3 # Dc = 1.34 FOOO = 172.00 Mu = 1.08 M = 160.17 _chemical_formula_sum 'C6 H12 N2 O3' _chemical_formula_moiety 'C6 H10 N2 O2, H2 O' _chemical_compound_source ? _chemical_formula_weight 160.17 _cell_measurement_reflns_used 4605 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.26 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_max 0.45 _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 172 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (Siemens, 1996) The following data are from Sadabs: ; _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 1.00 # Sheldrick geometric approximatio 0.96 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 \w _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _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 9556 _reflns_number_total 2297 _diffrn_reflns_av_R_equivalents 0.039 # Number of reflections with Friedels Law is 2297 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2413 _diffrn_reflns_theta_min 2.391 _diffrn_reflns_theta_max 30.479 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.041 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -10 _reflns_limit_k_max 10 _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 -0.21 _refine_diff_density_max 0.37 _refine_ls_number_reflns 2291 _refine_ls_number_restraints 0 _refine_ls_number_parameters 116 #_refine_ls_R_factor_ref 0.0477 _refine_ls_wR_factor_ref 0.1173 _refine_ls_goodness_of_fit_ref 0.9936 #_reflns_number_all 2291 _refine_ls_R_factor_all 0.0477 _refine_ls_wR_factor_all 0.1173 # 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 1876 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_gt 0.1155 _refine_ls_shift/su_max 0.000184 # 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 ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.728E-01 0.288E-01 0.00 0.00 0.00 0.333 ; # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.59511(15) 0.79848(13) 0.53505(9) 0.0318 1.0000 Uani . . . . . . O2 O 0.26833(13) 0.54605(11) 0.11854(10) 0.0309 1.0000 Uani . . . . . . O11 O 0.36657(19) 0.23023(14) 0.16476(10) 0.0401 1.0000 Uani . . . . . . N1 N 0.69872(14) 0.81983(13) 0.31690(9) 0.0219 1.0000 Uani . . . . . . N2 N 0.20102(16) 0.79665(14) 0.04395(11) 0.0251 1.0000 Uani . . . . . . C1 C 0.69965(17) 0.76700(15) 0.45174(11) 0.0224 1.0000 Uani . . . . . . C2 C 0.84793(18) 0.66660(17) 0.48231(13) 0.0287 1.0000 Uani . . . . . . C3 C 0.9461(2) 0.6772(2) 0.34865(15) 0.0366 1.0000 Uani . . . . . . C4 C 0.82519(19) 0.75767(18) 0.23419(13) 0.0289 1.0000 Uani . . . . . . C5 C 0.55604(17) 0.90132(15) 0.24758(11) 0.0223 1.0000 Uani . . . . . . C6 C 0.32824(17) 0.73136(15) 0.12984(11) 0.0217 1.0000 Uani . . . . . . H9 H 0.062(3) 0.707(3) -0.0144(18) 0.037(4) 1.0000 Uiso . . . . . . H10 H 0.242(2) 0.930(2) 0.0645(16) 0.036(4) 1.0000 Uiso . . . . . . H111 H 0.373(3) 0.227(3) 0.258(2) 0.060(5) 1.0000 Uiso . . . . . . H112 H 0.343(3) 0.339(3) 0.154(2) 0.061(5) 1.0000 Uiso . . . . . . H21 H 0.9727 0.7440 0.5859 0.0340 1.0000 Uiso . . . . . . H22 H 0.7556 0.5191 0.4815 0.0340 1.0000 Uiso . . . . . . H31 H 1.1136 0.7743 0.3897 0.0479 1.0000 Uiso . . . . . . H32 H 0.9158 0.5364 0.2956 0.0479 1.0000 Uiso . . . . . . H41 H 0.9378 0.8789 0.2097 0.0382 1.0000 Uiso . . . . . . H42 H 0.7196 0.6459 0.1346 0.0382 1.0000 Uiso . . . . . . H51 H 0.6366 1.0017 0.1923 0.0270 1.0000 Uiso . . . . . . H52 H 0.5274 0.9749 0.3329 0.0270 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0424(5) 0.0345(4) 0.0282(4) 0.0133(3) 0.0178(3) 0.0226(4) O2 0.0286(4) 0.0191(4) 0.0402(4) 0.0045(3) 0.0030(3) 0.0129(3) O11 0.0715(7) 0.0300(4) 0.0277(4) 0.0110(3) 0.0144(4) 0.0325(5) N1 0.0224(4) 0.0242(4) 0.0219(4) 0.0068(3) 0.0076(3) 0.0135(3) N2 0.0246(4) 0.0216(4) 0.0275(4) 0.0048(3) 0.0041(4) 0.0129(4) C1 0.0225(4) 0.0180(4) 0.0225(4) 0.0048(3) 0.0048(4) 0.0079(4) C2 0.0265(5) 0.0249(5) 0.0337(5) 0.0107(4) 0.0049(4) 0.0135(4) C3 0.0364(6) 0.0421(7) 0.0412(6) 0.0101(5) 0.0120(5) 0.0284(5) C4 0.0295(5) 0.0333(5) 0.0327(5) 0.0106(4) 0.0160(4) 0.0194(4) C5 0.0240(5) 0.0200(4) 0.0234(4) 0.0065(3) 0.0063(4) 0.0118(4) C6 0.0236(5) 0.0207(4) 0.0228(4) 0.0052(3) 0.0079(4) 0.0125(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.87(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.2349(12) yes O2 . C6 . 1.2367(12) yes O11 . H111 . 0.85(2) no O11 . H112 . 0.90(2) no N1 . C1 . 1.3409(12) yes N1 . C4 . 1.4603(12) yes N1 . C5 . 1.4392(12) yes N2 . C6 . 1.3309(12) yes N2 . H9 . 0.870(16) no N2 . H10 . 0.886(16) no C1 . C2 . 1.5103(14) yes C2 . C3 . 1.5290(17) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.5283(16) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.5264(14) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 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 H111 . O11 . H112 . 104.4(17) no C1 . N1 . C4 . 114.52(8) yes C1 . N1 . C5 . 122.38(8) yes C4 . N1 . C5 . 122.41(8) yes C6 . N2 . H9 . 118.8(10) no C6 . N2 . H10 . 120.3(9) no H9 . N2 . H10 . 118.9(15) no N1 . C1 . O1 . 124.16(9) yes N1 . C1 . C2 . 108.86(9) yes O1 . C1 . C2 . 126.98(9) yes C1 . C2 . C3 . 105.53(9) yes C1 . C2 . H21 . 110.451 no C3 . C2 . H21 . 110.447 no C1 . C2 . H22 . 110.452 no C3 . C2 . H22 . 110.449 no H21 . C2 . H22 . 109.465 no C2 . C3 . C4 . 105.80(9) yes C2 . C3 . H31 . 110.383 no C4 . C3 . H31 . 110.377 no C2 . C3 . H32 . 110.383 no C4 . C3 . H32 . 110.385 no H31 . C3 . H32 . 109.463 no C3 . C4 . N1 . 104.46(8) yes C3 . C4 . H41 . 110.716 no N1 . C4 . H41 . 110.714 no C3 . C4 . H42 . 110.706 no N1 . C4 . H42 . 110.703 no H41 . C4 . H42 . 109.464 no N1 . C5 . C6 . 112.23(8) yes N1 . C5 . H51 . 108.776 no C6 . C5 . H51 . 108.777 no N1 . C5 . H52 . 108.778 no C6 . C5 . H52 . 108.782 no H51 . C5 . H52 . 109.467 no C5 . C6 . N2 . 115.66(8) yes C5 . C6 . O2 . 121.03(9) yes N2 . C6 . O2 . 123.30(10) yes data_CRYSTALS_cif_2 _database_code_depnum_ccdc_archive 'CCDC 258690' _audit_creation_date 04-11-09 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title '5678 in P2(1)/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.9537(11) _cell_length_b 5.4541(6) _cell_length_c 13.610(4) _cell_angle_alpha 90 _cell_angle_beta 104.93(2) _cell_angle_gamma 90 _cell_volume 642.2(2) _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 C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H1 N2 O2 # Dc = 1.38 Fooo = 304.00 Mu = 1.08 M = 133.09 # Found Formula = C6 H10 N2 O2 # Dc = 1.47 FOOO = 304.00 Mu = 1.12 M = 142.16 _chemical_formula_sum 'C6 H10 N2 O2' _chemical_formula_moiety 'C6 H10 N2 O2' _chemical_compound_source ? _chemical_formula_weight 142.16 _cell_measurement_reflns_used 379 _cell_measurement_theta_min 4 _cell_measurement_theta_max 26 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type 'Empirical & multi-scan' _exptl_absorpt_process_details ; SHADE (Parsons, 2004) SADABS (Siemens, 1996) The following data are from Sadabs: ; _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_T_max 1.00 # Sheldrick geometric definitions 0.98 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 \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 293 _reflns_number_total 470 #_diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 470 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1369 _diffrn_reflns_number 3718 #_diffrn_radiation_wavelength 0.71073 #_diffrn_reflns_theta_max 26.768 #_diffrn_reflns_theta_min 2.462 #_diffrn_reflns_limit_h_max 11 #_diffrn_reflns_limit_h_min -11 #_diffrn_reflns_limit_k_max 6 #_diffrn_reflns_limit_k_min -6 #_diffrn_reflns_limit_l_max 9 #_diffrn_reflns_limit_l_min -8 _diffrn_reflns_av_R_equivalents 0.0784 #; # Scaled and merged with SORTAV # R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 # R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 #; _diffrn_reflns_theta_min 4.045 _diffrn_reflns_theta_max 26.768 _diffrn_measured_fraction_theta_max 0.344 _diffrn_reflns_theta_full 25.162 _diffrn_measured_fraction_theta_full 0.376 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _reflns_limit_h_min -11 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 9 _oxford_diffrn_Wilson_B_factor 1.57 _oxford_diffrn_Wilson_scale 79.84 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.24 _refine_diff_density_max 0.20 _refine_ls_number_reflns 457 _refine_ls_number_restraints 83 _refine_ls_number_parameters 92 #_refine_ls_R_factor_ref 0.0724 _refine_ls_wR_factor_ref 0.1026 _refine_ls_goodness_of_fit_ref 1.0911 #_reflns_number_all 457 _refine_ls_R_factor_all 0.0724 _refine_ls_wR_factor_all 0.1026 # 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 359 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_gt 0.0957 _refine_ls_shift/su_max 0.000135 # 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 noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.247E-01 0.610 0.00 0.00 0.00 0.333 ; # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.7062(3) 0.1757(5) 0.9364(5) 0.0307 1.0000 Uani . U . . . . C1 C 0.5573(4) 0.1095(7) 0.9011(6) 0.0252 1.0000 Uani . U . . . . C2 C 0.5486(4) -0.1109(7) 0.8347(6) 0.0339 1.0000 Uani . U . . . . C3 C 0.7083(4) -0.1235(7) 0.8121(7) 0.0355 1.0000 Uani . U . . . . C4 C 0.8122(4) 0.0229(7) 0.8972(6) 0.0357 1.0000 Uani . U . . . . O1 O 0.4476(3) 0.2133(4) 0.9236(4) 0.0371 1.0000 Uani . U . . . . C5 C 0.7616(5) 0.3773(7) 1.0053(7) 0.0329 1.0000 Uani . U . . . . C6 C 0.8626(4) 0.3127(7) 1.1086(7) 0.0312 1.0000 Uani . U . . . . N2 N 0.8370(3) 0.1005(6) 1.1492(5) 0.0357 1.0000 Uani . U . . . . O2 O 0.9635(3) 0.4576(5) 1.1517(4) 0.0434 1.0000 Uani . U . . . . H21 H 0.5287 -0.2622 0.8709 0.0411 1.0000 Uiso . . . . . . H22 H 0.4653 -0.0911 0.7703 0.0411 1.0000 Uiso . . . . . . H31 H 0.7449 -0.2971 0.8134 0.0446 1.0000 Uiso . . . . . . H32 H 0.7052 -0.0484 0.7448 0.0446 1.0000 Uiso . . . . . . H41 H 0.8723 -0.0884 0.9519 0.0454 1.0000 Uiso . . . . . . H42 H 0.8855 0.1267 0.8711 0.0454 1.0000 Uiso . . . . . . H51 H 0.6692 0.4660 1.0160 0.0404 1.0000 Uiso . . . . . . H52 H 0.8221 0.4892 0.9721 0.0404 1.0000 Uiso . . . . . . H9 H 0.8940 0.0594 1.2109 0.0420 1.0000 Uiso . . . . . . H10 H 0.7638 0.0014 1.1170 0.0420 1.0000 Uiso . . . . . . 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 0.0268(13) 0.0285(18) 0.037(6) -0.003(2) 0.008(2) -0.0006(12) C1 0.0268(14) 0.030(2) 0.018(9) 0.004(3) 0.004(3) 0.0000(14) C2 0.0309(18) 0.031(2) 0.039(10) -0.004(3) 0.008(3) -0.0018(15) C3 0.038(2) 0.042(3) 0.029(9) -0.002(3) 0.014(3) 0.0026(18) C4 0.0306(18) 0.040(3) 0.041(9) -0.005(3) 0.016(3) -0.0009(16) O1 0.0284(13) 0.0380(16) 0.045(8) 0.000(2) 0.010(3) 0.0067(11) C5 0.034(2) 0.030(2) 0.034(6) -0.001(2) 0.007(2) -0.0031(15) C6 0.0240(17) 0.035(2) 0.035(6) -0.004(3) 0.008(2) 0.0017(15) N2 0.0330(18) 0.042(2) 0.030(9) 0.001(3) 0.003(3) -0.0040(14) O2 0.0380(15) 0.0493(19) 0.039(8) -0.005(2) 0.002(2) -0.0115(11) _refine_ls_extinction_coef 57(17) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _oxford_refine_ls_scale 0.436(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 . C1 . 1.345(5) yes N1 . C4 . 1.463(6) yes N1 . C5 . 1.447(8) yes C1 . C2 . 1.494(8) yes C1 . O1 . 1.238(4) yes C2 . C3 . 1.540(5) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.513(9) yes C3 . H31 . 1.001 no C3 . H32 . 0.997 no C4 . H41 . 1.003 no C4 . H42 . 0.998 no C5 . C6 . 1.504(12) yes C5 . H51 . 1.000 no C5 . H52 . 0.999 no C6 . N2 . 1.327(6) yes C6 . O2 . 1.229(5) yes N2 . H9 . 0.892 no N2 . H10 . 0.875 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 C1 . N1 . C4 . 113.2(4) yes C1 . N1 . C5 . 125.3(4) yes C4 . N1 . C5 . 121.6(3) yes N1 . C1 . C2 . 108.9(3) yes N1 . C1 . O1 . 124.4(5) yes C2 . C1 . O1 . 126.6(4) yes C1 . C2 . C3 . 104.5(3) yes C1 . C2 . H21 . 110.744 no C3 . C2 . H21 . 110.734 no C1 . C2 . H22 . 110.736 no C3 . C2 . H22 . 110.573 no H21 . C2 . H22 . 109.478 no C2 . C3 . C4 . 104.1(5) yes C2 . C3 . H31 . 110.762 no C4 . C3 . H31 . 110.632 no C2 . C3 . H32 . 110.958 no C4 . C3 . H32 . 110.668 no H31 . C3 . H32 . 109.666 no C3 . C4 . N1 . 104.6(3) yes C3 . C4 . H41 . 110.802 no N1 . C4 . H41 . 110.363 no C3 . C4 . H42 . 110.987 no N1 . C4 . H42 . 110.718 no H41 . C4 . H42 . 109.352 no N1 . C5 . C6 . 116.8(4) yes N1 . C5 . H51 . 107.688 no C6 . C5 . H51 . 107.374 no N1 . C5 . H52 . 107.795 no C6 . C5 . H52 . 107.485 no H51 . C5 . H52 . 109.570 no C5 . C6 . N2 . 117.8(5) yes C5 . C6 . O2 . 119.1(5) yes N2 . C6 . O2 . 123.1(7) yes C6 . N2 . H9 . 119.573 no C6 . N2 . H10 . 121.166 no H9 . N2 . H10 . 119.247 no data_CRYSTALS_cif_3 _database_code_depnum_ccdc_archive 'CCDC 258691' _audit_creation_date 04-11-10 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'pirchk in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.7254(2) _cell_length_b 13.2572(4) _cell_length_c 8.0529(2) _cell_angle_alpha 90 _cell_angle_beta 98.603(2) _cell_angle_gamma 90 _cell_volume 709.92(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H10 N2 O2 # Dc = 1.33 Fooo = 304.00 Mu = 1.01 M = 142.16 # Found Formula = C6.00 H10.00 N2 O2 # Dc = 1.33 FOOO = 304.00 Mu = 1.01 M = 142.16 _chemical_formula_sum 'C6 H10 N2 O2' _chemical_formula_moiety 'C6 H10 N2 O2' _chemical_compound_source ? _chemical_formula_weight 142.16 _cell_measurement_reflns_used 2057 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.19 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.41 _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (Siemens, 1996) The following data are from Sadabs: ; _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 1.00 # Sheldrick geometric approximatio 0.98 0.98 _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' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _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 8349 _reflns_number_total 2123 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections with Friedels Law is 2123 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1561 _diffrn_reflns_theta_min 2.984 _diffrn_reflns_theta_max 30.565 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.064 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 1.93 _oxford_diffrn_Wilson_scale 0.78 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom+difmap _refine_diff_density_min -0.24 _refine_diff_density_max 0.24 _refine_ls_number_reflns 1545 _refine_ls_number_restraints 4 _refine_ls_number_parameters 103 #_refine_ls_R_factor_ref 0.0618 _refine_ls_wR_factor_ref 0.0913 _refine_ls_goodness_of_fit_ref 0.9736 #_reflns_number_all 1545 _refine_ls_R_factor_all 0.0618 _refine_ls_wR_factor_all 0.0913 # 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 1215 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_gt 0.0842 _refine_ls_shift/su_max 0.000226 # 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 ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.297E-01 0.00 0.00 0.00 0.00 0.333 ; # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.0858(2) 0.39574(9) 0.14311(15) 0.0235 1.0000 Uani . . . . . . N2 N -0.2925(2) 0.19588(10) 0.08810(18) 0.0286 1.0000 Uani . . . . . . O1 O -0.09626(18) 0.51227(8) 0.26255(15) 0.0371 1.0000 Uani . . . . . . O2 O -0.02721(17) 0.22241(8) 0.28993(13) 0.0305 1.0000 Uani . . . . . . C1 C 0.0662(2) 0.47567(11) 0.24211(18) 0.0249 1.0000 Uani . . . . . . C2 C 0.2718(3) 0.50955(12) 0.3199(2) 0.0328 1.0000 Uani D . . . . . C4 C 0.2929(3) 0.36501(13) 0.1394(2) 0.0339 1.0000 Uani D . . . . . C5 C -0.0837(2) 0.34048(11) 0.05955(19) 0.0271 1.0000 Uani . . . . . . C6 C -0.1322(2) 0.24716(10) 0.15742(18) 0.0230 1.0000 Uani . . . . . . C31 C 0.4134(8) 0.4547(5) 0.2207(8) 0.0399 0.657(14) Uani D . P 1 1 . C32 C 0.4201(18) 0.4322(9) 0.2689(15) 0.0433 0.343(14) Uani D . P 1 2 . H51 H -0.2034 0.3858 0.0445 0.0313 1.0000 Uiso . . . . . . H52 H -0.0530 0.3184 -0.0525 0.0313 1.0000 Uiso . . . . . . H311 H 0.4535 0.5007 0.1338 0.0457 0.657(14) Uiso . . P 1 1 . H312 H 0.5343 0.4317 0.2980 0.0457 0.657(14) Uiso . . P 1 1 . H321 H 0.5333 0.4635 0.2157 0.0498 0.343(14) Uiso . . P 1 2 . H322 H 0.4857 0.3888 0.3661 0.0498 0.343(14) Uiso . . P 1 2 . H411 H 0.3194 0.3546 0.0221 0.0411 0.657(14) Uiso . . P 1 1 . H412 H 0.3265 0.3020 0.2062 0.0411 0.657(14) Uiso . . P 1 1 . H211 H 0.2869 0.5838 0.3090 0.0392 0.657(14) Uiso . . P 1 1 . H212 H 0.2999 0.4895 0.4407 0.0392 0.657(14) Uiso . . P 1 1 . H221 H 0.3021 0.5774 0.2766 0.0392 0.343(14) Uiso . . P 1 2 . H222 H 0.2822 0.5114 0.4445 0.0392 0.343(14) Uiso . . P 1 2 . H421 H 0.3295 0.3762 0.0253 0.0411 0.343(14) Uiso . . P 1 2 . H422 H 0.3108 0.2922 0.1705 0.0411 0.343(14) Uiso . . P 1 2 . H10 H -0.330(3) 0.1425(14) 0.136(2) 0.038(5) 1.0000 Uiso . . . . . . H9 H -0.365(3) 0.2161(13) -0.007(2) 0.037(5) 1.0000 Uiso . . . . . . 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 0.0211(7) 0.0233(6) 0.0261(7) -0.0017(5) 0.0034(5) -0.0002(5) N2 0.0304(8) 0.0267(7) 0.0265(7) 0.0054(6) -0.0033(6) -0.0044(6) O1 0.0324(7) 0.0320(6) 0.0485(8) -0.0069(5) 0.0114(6) 0.0041(5) O2 0.0330(7) 0.0306(6) 0.0251(6) 0.0046(5) -0.0047(5) -0.0026(5) C1 0.0291(9) 0.0216(7) 0.0250(8) 0.0019(6) 0.0067(7) -0.0039(6) C2 0.0339(10) 0.0318(8) 0.0310(9) 0.0036(7) -0.0009(7) -0.0110(7) C4 0.0266(9) 0.0418(9) 0.0350(9) 0.0008(8) 0.0098(7) 0.0074(8) C5 0.0307(9) 0.0242(7) 0.0242(8) 0.0003(6) -0.0030(7) -0.0023(7) C6 0.0247(9) 0.0225(7) 0.0213(7) -0.0027(6) 0.0022(6) 0.0039(6) C31 0.0224(11) 0.059(3) 0.037(3) 0.0092(18) 0.0024(19) -0.0048(16) C32 0.0258(11) 0.063(3) 0.041(3) 0.0092(18) 0.0029(19) -0.0048(16) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.235(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.3444(19) yes N1 . C4 . 1.456(2) yes N1 . C5 . 1.4349(19) yes N2 . C6 . 1.325(2) yes N2 . H10 . 0.863(19) no N2 . H9 . 0.886(18) no O1 . C1 . 1.2286(19) yes O2 . C6 . 1.2326(18) yes C1 . C2 . 1.499(2) yes C2 . C31 . 1.517(5) yes C2 . H211 . 0.995 no C2 . H212 . 0.999 no C2 . C32 . 1.528(8) yes C2 . H221 . 0.997 no C2 . H222 . 0.996 no C4 . C31 . 1.530(6) yes C4 . H411 . 0.997 no C4 . H412 . 1.001 no C4 . C32 . 1.532(14) yes C4 . H421 . 0.997 no C4 . H422 . 0.999 no C5 . C6 . 1.528(2) yes C5 . H51 . 0.997 no C5 . H52 . 0.999 no C31 . H311 . 0.996 no C31 . H312 . 0.995 no C32 . H321 . 1.017 no C32 . H322 . 1.017 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 C1 . N1 . C4 . 114.31(13) yes C1 . N1 . C5 . 122.62(13) yes C4 . N1 . C5 . 122.87(12) yes C6 . N2 . H10 . 120.5(12) no C6 . N2 . H9 . 121.1(11) no H10 . N2 . H9 . 118.4(16) no N1 . C1 . O1 . 123.97(15) yes N1 . C1 . C2 . 108.52(14) yes O1 . C1 . C2 . 127.51(14) yes C1 . C2 . C31 . 104.4(3) yes C1 . C2 . H211 . 111.053 no C31 . C2 . H211 . 110.348 no C1 . C2 . H212 . 110.837 no C31 . C2 . H212 . 110.071 no H211 . C2 . H212 . 109.992 no C1 . C2 . C32 . 106.6(5) yes C1 . C2 . H221 . 110.397 no C32 . C2 . H221 . 109.642 no C1 . C2 . H222 . 110.467 no C32 . C2 . H222 . 109.689 no H221 . C2 . H222 . 110.025 no N1 . C4 . C31 . 102.8(2) yes N1 . C4 . H411 . 111.421 no C31 . C4 . H411 . 110.775 no N1 . C4 . H412 . 111.229 no C31 . C4 . H412 . 110.837 no H411 . C4 . H412 . 109.665 no N1 . C4 . C32 . 105.2(3) yes N1 . C4 . H421 . 110.261 no C32 . C4 . H421 . 110.565 no N1 . C4 . H422 . 110.178 no C32 . C4 . H422 . 110.874 no H421 . C4 . H422 . 109.719 no N1 . C5 . C6 . 112.79(12) yes N1 . C5 . H51 . 108.641 no C6 . C5 . H51 . 108.641 no N1 . C5 . H52 . 108.440 no C6 . C5 . H52 . 108.515 no H51 . C5 . H52 . 109.791 no C5 . C6 . N2 . 114.90(13) yes C5 . C6 . O2 . 121.55(13) yes N2 . C6 . O2 . 123.55(14) yes C4 . C31 . C2 . 105.3(3) yes C4 . C31 . H311 . 110.925 no C2 . C31 . H311 . 109.468 no C4 . C31 . H312 . 111.116 no C2 . C31 . H312 . 109.649 no H311 . C31 . H312 . 110.261 no C4 . C32 . C2 . 104.6(7) yes C4 . C32 . H321 . 109.131 no C2 . C32 . H321 . 113.500 no C4 . C32 . H322 . 109.205 no C2 . C32 . H322 . 113.473 no H321 . C32 . H322 . 106.794 no