# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Cristina Puigjaner' _publ_contact_author_email CRIS@SCT.UB.ES _publ_section_title ; New polymorphic hydrogen bonding donor-acceptor system with two temperature coincident solid-solid transitions ; loop_ _publ_author_name 'Cristina Puigjaner' 'Rafael Barbas' 'Dario Braga' 'Marco Polito' 'Anna Portell' 'Rafel Prohens' # Attachment 'formA.cif' data_c2 _database_code_depnum_ccdc_archive 'CCDC 676071' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 11.403(2) _cell_length_b 4.4101(10) _cell_length_c 30.270(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.807(5) _cell_angle_gamma 90.00 _cell_volume 1495.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7998 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 0.68 _diffrn_reflns_theta_max 26.73 _reflns_number_total 1803 _reflns_number_gt 1422 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1169P)^2^+0.0843P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1803 _refine_ls_number_parameters 201 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1776 _refine_ls_wR_factor_gt 0.1533 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C19 C 0.7329(4) 0.2341(11) 0.62372(15) 0.0452(11) Uani 1 1 d . . . C20 C 0.8215(5) 0.3444(18) 0.60204(18) 0.0621(15) Uani 1 1 d . . . H30 H 0.9013 0.3043 0.6139 0.074 Uiso 1 1 calc R . . C21 C 0.7926(6) 0.5111(19) 0.56339(19) 0.0718(18) Uani 1 1 d . . . H29 H 0.8530 0.5798 0.5491 0.086 Uiso 1 1 calc R . . C22 C 0.6772(8) 0.5780(19) 0.54559(19) 0.081(2) Uani 1 1 d . . . H28 H 0.6584 0.6919 0.5193 0.097 Uiso 1 1 calc R . . C23 C 0.5870(6) 0.473(2) 0.5672(2) 0.079(2) Uani 1 1 d . . . H27 H 0.5076 0.5197 0.5556 0.094 Uiso 1 1 calc R . . C24 C 0.6156(5) 0.3011(17) 0.60590(18) 0.0614(15) Uani 1 1 d . . . H26 H 0.5552 0.2298 0.6200 0.074 Uiso 1 1 calc R . . C25 C 0.7640(5) 0.0412(13) 0.66595(15) 0.0512(12) Uani 1 1 d . . . H32A H 0.7191 -0.1466 0.6614 0.061 Uiso 1 1 calc R . . H32B H 0.8482 -0.0097 0.6708 0.061 Uiso 1 1 calc R . . C26 C 0.8120(4) 0.3812(11) 0.73035(16) 0.0409(11) Uani 1 1 d . . . C27 C 0.9347(4) 0.4842(13) 0.73038(16) 0.0478(12) Uani 1 1 d . . . C28 C 0.9283(4) 0.6753(12) 0.76953(17) 0.0454(11) Uani 1 1 d . . . C29 C 0.8066(4) 0.5606(11) 0.76864(15) 0.0399(10) Uani 1 1 d . . . C30 C 0.7414(4) 0.8133(12) 0.83196(14) 0.0479(12) Uani 1 1 d . . . H37A H 0.6697 0.9317 0.8320 0.057 Uiso 1 1 calc R . . H37B H 0.8063 0.9530 0.8306 0.057 Uiso 1 1 calc R . . C31 C 0.7697(4) 0.6311(11) 0.87481(16) 0.0454(11) Uani 1 1 d . . . C32 C 0.8855(5) 0.5562(18) 0.89420(19) 0.0648(17) Uani 1 1 d . . . H40 H 0.9475 0.6200 0.8804 0.078 Uiso 1 1 calc R . . C33 C 0.9122(6) 0.391(2) 0.9332(2) 0.081(2) Uani 1 1 d . . . H100 H 0.9911 0.3442 0.9456 0.097 Uiso 1 1 calc R . . C34 C 0.8201(8) 0.294(2) 0.95394(18) 0.083(2) Uani 1 1 d . . . H101 H 0.8367 0.1827 0.9804 0.100 Uiso 1 1 calc R . . C35 C 0.7040(6) 0.365(2) 0.93497(19) 0.077(2) Uani 1 1 d . . . H112 H 0.6420 0.2996 0.9487 0.093 Uiso 1 1 calc R . . C36 C 0.6793(5) 0.529(2) 0.89643(17) 0.0641(17) Uani 1 1 d . . . H39 H 0.6003 0.5738 0.8841 0.077 Uiso 1 1 calc R . . N3 N 0.7387(3) 0.1916(11) 0.70569(13) 0.0477(10) Uani 1 1 d . . . H3 H 0.6715 0.1543 0.7136 0.057 Uiso 1 1 calc R . . N4 N 0.7235(3) 0.6161(10) 0.79218(12) 0.0468(10) Uani 1 1 d . . . H4 H 0.6548 0.5323 0.7839 0.056 Uiso 1 1 calc R . . O1 O 0.9964(3) 0.8568(10) 0.79325(11) 0.0587(10) Uani 1 1 d . . . O2 O 1.0096(3) 0.4379(11) 0.70623(12) 0.0610(11) Uani 1 1 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 C19 0.039(2) 0.044(3) 0.053(3) -0.010(2) 0.0101(19) -0.005(2) C20 0.047(3) 0.074(4) 0.070(3) -0.012(4) 0.025(2) -0.014(3) C21 0.071(4) 0.083(5) 0.066(3) 0.001(4) 0.026(3) -0.022(4) C22 0.112(6) 0.077(5) 0.053(3) 0.006(3) 0.015(3) -0.015(5) C23 0.063(4) 0.091(5) 0.078(4) 0.003(4) 0.003(3) 0.010(4) C24 0.045(3) 0.070(4) 0.069(3) 0.000(3) 0.011(2) -0.001(3) C25 0.044(3) 0.044(3) 0.064(3) -0.004(3) 0.007(2) -0.003(2) C26 0.0254(19) 0.038(2) 0.059(3) 0.007(2) 0.0065(18) -0.0091(19) C27 0.025(2) 0.051(3) 0.066(3) 0.007(2) 0.006(2) -0.009(2) C28 0.027(2) 0.045(2) 0.064(3) 0.006(2) 0.0058(19) -0.015(2) C29 0.0235(19) 0.043(2) 0.052(2) 0.006(2) 0.0037(18) -0.0056(18) C30 0.035(2) 0.046(3) 0.063(3) -0.004(3) 0.012(2) -0.003(2) C31 0.035(2) 0.048(3) 0.055(3) -0.012(2) 0.011(2) -0.004(2) C32 0.035(2) 0.084(4) 0.075(4) 0.006(4) 0.010(2) -0.002(3) C33 0.059(4) 0.109(6) 0.072(3) 0.009(5) 0.002(3) 0.007(5) C34 0.109(6) 0.089(5) 0.049(3) 0.003(4) 0.011(3) -0.020(5) C35 0.072(4) 0.102(6) 0.062(3) -0.012(4) 0.023(3) -0.034(4) C36 0.046(3) 0.090(5) 0.059(3) -0.013(4) 0.016(2) -0.015(3) N3 0.0299(18) 0.052(2) 0.061(2) 0.001(2) 0.0073(17) -0.014(2) N4 0.0299(17) 0.050(2) 0.061(2) -0.002(2) 0.0097(17) -0.0093(19) O1 0.0362(17) 0.063(2) 0.075(2) -0.007(2) 0.0065(16) -0.0241(19) O2 0.0266(15) 0.082(3) 0.078(2) -0.004(2) 0.0188(16) -0.0121(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C19 C24 1.377(7) . ? C19 C20 1.392(7) . ? C19 C25 1.521(7) . ? C20 C21 1.369(9) . ? C20 H30 0.9300 . ? C21 C22 1.358(10) . ? C21 H29 0.9300 . ? C22 C23 1.398(10) . ? C22 H28 0.9300 . ? C23 C24 1.382(9) . ? C23 H27 0.9300 . ? C24 H26 0.9300 . ? C25 N3 1.449(7) . ? C25 H32A 0.9700 . ? C25 H32B 0.9700 . ? C26 N3 1.312(6) . ? C26 C29 1.414(7) . ? C26 C27 1.471(5) . ? C27 O2 1.241(6) . ? C27 C28 1.467(7) . ? C28 O1 1.245(6) . ? C28 C29 1.473(5) . ? C29 N4 1.311(6) . ? C30 N4 1.468(6) . ? C30 C31 1.509(6) . ? C30 H37A 0.9700 . ? C30 H37B 0.9700 . ? C31 C32 1.381(7) . ? C31 C36 1.396(7) . ? C32 C33 1.373(9) . ? C32 H40 0.9300 . ? C33 C34 1.388(11) . ? C33 H100 0.9300 . ? C34 C35 1.376(10) . ? C34 H101 0.9300 . ? C35 C36 1.356(10) . ? C35 H112 0.9300 . ? C36 H39 0.9300 . ? N3 H3 0.8600 . ? N4 H4 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C24 C19 C20 118.6(5) . . ? C24 C19 C25 120.4(5) . . ? C20 C19 C25 121.1(5) . . ? C21 C20 C19 120.7(6) . . ? C21 C20 H30 119.7 . . ? C19 C20 H30 119.7 . . ? C22 C21 C20 121.1(6) . . ? C22 C21 H29 119.4 . . ? C20 C21 H29 119.4 . . ? C21 C22 C23 119.1(6) . . ? C21 C22 H28 120.5 . . ? C23 C22 H28 120.5 . . ? C24 C23 C22 120.1(6) . . ? C24 C23 H27 120.0 . . ? C22 C23 H27 120.0 . . ? C19 C24 C23 120.5(6) . . ? C19 C24 H26 119.8 . . ? C23 C24 H26 119.8 . . ? N3 C25 C19 113.0(5) . . ? N3 C25 H32A 109.0 . . ? C19 C25 H32A 109.0 . . ? N3 C25 H32B 109.0 . . ? C19 C25 H32B 109.0 . . ? H32A C25 H32B 107.8 . . ? N3 C26 C29 134.6(4) . . ? N3 C26 C27 134.5(5) . . ? C29 C26 C27 90.8(4) . . ? O2 C27 C28 135.6(5) . . ? O2 C27 C26 135.1(5) . . ? C28 C27 C26 89.2(4) . . ? O1 C28 C27 135.7(4) . . ? O1 C28 C29 135.6(5) . . ? C27 C28 C29 88.7(4) . . ? N4 C29 C26 134.1(4) . . ? N4 C29 C28 134.5(5) . . ? C26 C29 C28 91.3(4) . . ? N4 C30 C31 111.3(4) . . ? N4 C30 H37A 109.4 . . ? C31 C30 H37A 109.4 . . ? N4 C30 H37B 109.4 . . ? C31 C30 H37B 109.4 . . ? H37A C30 H37B 108.0 . . ? C32 C31 C36 117.1(5) . . ? C32 C31 C30 121.8(5) . . ? C36 C31 C30 121.1(5) . . ? C33 C32 C31 122.2(6) . . ? C33 C32 H40 118.9 . . ? C31 C32 H40 118.9 . . ? C32 C33 C34 119.2(6) . . ? C32 C33 H100 120.4 . . ? C34 C33 H100 120.4 . . ? C35 C34 C33 119.5(6) . . ? C35 C34 H101 120.3 . . ? C33 C34 H101 120.3 . . ? C36 C35 C34 120.5(6) . . ? C36 C35 H112 119.7 . . ? C34 C35 H112 119.7 . . ? C35 C36 C31 121.5(6) . . ? C35 C36 H39 119.2 . . ? C31 C36 H39 119.2 . . ? C26 N3 C25 124.0(4) . . ? C26 N3 H3 118.0 . . ? C25 N3 H3 118.0 . . ? C29 N4 C30 123.6(4) . . ? C29 N4 H4 118.2 . . ? C30 N4 H4 118.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O2 0.86 2.05 2.845(5) 152.7 3_445 N4 H4 O1 0.86 2.03 2.837(5) 155.1 3_445 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.392 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.114 # Attachment 'formC.cif' data_new _database_code_depnum_ccdc_archive 'CCDC 686074' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.4956(18) _cell_length_b 6.0254(3) _cell_length_c 8.1984(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.760(6) _cell_angle_gamma 90.00 _cell_volume 1495.97(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10891 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 29.14 _reflns_number_total 1775 _reflns_number_gt 1155 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.6010P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1775 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1277 _refine_ls_R_factor_gt 0.0760 _refine_ls_wR_factor_ref 0.1971 _refine_ls_wR_factor_gt 0.1771 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.37528(8) 0.2731(4) 0.0596(3) 0.0446(6) Uani 1 1 d . . . C2 C 0.36165(10) 0.0927(5) 0.1456(4) 0.0603(8) Uani 1 1 d . . . H2 H 0.3801 -0.0298 0.1643 0.072 Uiso 1 1 calc R . . C3 C 0.32140(11) 0.0930(6) 0.2032(4) 0.0730(9) Uani 1 1 d . . . H3 H 0.3128 -0.0282 0.2621 0.088 Uiso 1 1 calc R . . C4 C 0.29384(11) 0.2698(7) 0.1749(4) 0.0809(11) Uani 1 1 d . . . H4 H 0.2662 0.2684 0.2124 0.097 Uiso 1 1 calc R . . C5 C 0.30681(11) 0.4483(6) 0.0915(5) 0.0856(11) Uani 1 1 d . . . H5 H 0.2880 0.5694 0.0725 0.103 Uiso 1 1 calc R . . C6 C 0.34743(10) 0.4517(5) 0.0349(4) 0.0643(8) Uani 1 1 d . . . H6 H 0.3561 0.5759 -0.0205 0.077 Uiso 1 1 calc R . . C7 C 0.41913(9) 0.2695(4) -0.0072(3) 0.0527(7) Uani 1 1 d . . . H7A H 0.4235 0.1238 -0.0530 0.063 Uiso 1 1 calc R . . H7B H 0.4184 0.3764 -0.0960 0.063 Uiso 1 1 calc R . . C8 C 0.48131(8) 0.1649(3) 0.1915(3) 0.0408(6) Uani 1 1 d . . . C9 C 0.48074(8) -0.0777(4) 0.1869(3) 0.0443(6) Uani 1 1 d . . . N1 N 0.45642(7) 0.3196(3) 0.1134(3) 0.0477(6) Uani 1 1 d . . . O1 O 0.45749(6) -0.2192(3) 0.1111(2) 0.0566(6) Uani 1 1 d . . . H100 H 0.4653(10) 0.458(5) 0.143(4) 0.068(9) Uiso 1 1 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 C1 0.0526(14) 0.0400(14) 0.0398(13) -0.0055(10) -0.0006(11) -0.0008(11) C2 0.0627(18) 0.0487(17) 0.0688(18) 0.0068(13) 0.0052(15) -0.0031(13) C3 0.0632(19) 0.080(2) 0.075(2) 0.0084(17) 0.0058(16) -0.0159(18) C4 0.0536(18) 0.109(3) 0.082(2) -0.008(2) 0.0139(17) -0.006(2) C5 0.068(2) 0.082(2) 0.105(3) -0.005(2) 0.003(2) 0.026(2) C6 0.0723(19) 0.0472(16) 0.0726(19) 0.0037(14) 0.0050(16) 0.0081(15) C7 0.0677(17) 0.0414(15) 0.0506(15) -0.0005(11) 0.0134(13) 0.0023(13) C8 0.0496(13) 0.0239(11) 0.0530(14) -0.0005(10) 0.0233(10) 0.0006(10) C9 0.0575(15) 0.0243(12) 0.0561(15) -0.0017(10) 0.0267(11) -0.0017(10) N1 0.0527(13) 0.0263(11) 0.0666(14) -0.0026(10) 0.0172(11) -0.0006(10) O1 0.0742(13) 0.0262(9) 0.0713(13) -0.0069(8) 0.0168(10) -0.0050(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.371(4) . ? C1 C2 1.386(4) . ? C1 C7 1.504(4) . ? C2 C3 1.366(4) . ? C2 H2 0.9300 . ? C3 C4 1.360(5) . ? C3 H3 0.9300 . ? C4 C5 1.358(5) . ? C4 H4 0.9300 . ? C5 C6 1.373(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.448(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.319(3) . ? C8 C8 1.401(5) 2_655 ? C8 C9 1.462(3) . ? C9 O1 1.230(3) . ? C9 C9 1.471(6) 2_655 ? N1 H100 0.90(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.2(3) . . ? C6 C1 C7 121.3(2) . . ? C2 C1 C7 120.4(2) . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 120.4(3) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N1 C7 C1 114.1(2) . . ? N1 C7 H7A 108.7 . . ? C1 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C1 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? N1 C8 C8 135.05(14) . 2_655 ? N1 C8 C9 133.6(2) . . ? C8 C8 C9 91.36(15) 2_655 . ? O1 C9 C8 135.3(3) . . ? O1 C9 C9 136.10(14) . 2_655 ? C8 C9 C9 88.62(15) . 2_655 ? C8 N1 C7 123.0(2) . . ? C8 N1 H100 113(2) . . ? C7 N1 H100 124(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H100 O1 0.90(3) 1.97(3) 2.779(3) 148(3) 1_565 _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.277 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.047