# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Ren-Gen Xiong' _publ_contact_author_email XIONGRG@SEU.EDU.CN _publ_section_title ; Reversible phase transition of the 1:1 cocrystal of 1, 4-diazabicyclo-[2.2.2]octane (DABCO) and hydroquinone ; loop_ _publ_author_name 'Ren-Gen Xiong' 'Fang Chen' 'Heng-Yun Ye' 'Wen Zhang' # Attachment 'new2--180C.cif' data_93K _database_code_depnum_ccdc_archive 'CCDC 737143' #TrackingRef 'new2--180C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 N2, C6 H6 O2 ' _chemical_formula_sum 'C12 H18 N2 O2' _chemical_formula_weight 222.28 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 'P 21/n' _symmetry_space_group_name_HALL '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9278(7) _cell_length_b 9.3661(7) _cell_length_c 11.4995(8) _cell_angle_alpha 90.00 _cell_angle_beta 119.034(5) _cell_angle_gamma 90.00 _cell_volume 1123.24(13) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8268 _cell_measurement_theta_min 3.91 _cell_measurement_theta_max 27.44 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8943 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'crystalclear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis-Rapid diffractometer' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10564 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2550 _reflns_number_gt 2079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear (Rigaku, 2005)' _computing_cell_refinement 'crystalclear (Rigaku, 2005)' _computing_data_reduction 'crystalclear (Rigaku, 2005)' _computing_structure_solution 'SHELXtl (Sheldrick, 2008)' _computing_structure_refinement 'SHELXtl (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXtl (Sheldrick, 2008); diamond (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXtl (Sheldrick, 2008)' _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^)+(0.0634P)^2^+0.1809P] 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 2550 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 O1 O 0.13252(8) 0.33809(9) 0.09885(8) 0.0255(2) Uani 1 1 d . . . O2 O -0.10989(8) 0.35039(9) 0.40616(8) 0.0260(2) Uani 1 1 d . . . C1 C -0.05270(10) 0.34860(10) 0.32808(11) 0.0178(2) Uani 1 1 d . . . C3 C -0.05818(10) 0.35322(11) 0.11434(10) 0.0186(2) Uani 1 1 d . . . H3A H -0.1062 0.3596 0.0202 0.022 Uiso 1 1 calc R . . C4 C 0.07506(10) 0.34187(10) 0.17664(10) 0.0174(2) Uani 1 1 d . . . C6 C 0.08071(10) 0.34033(11) 0.39038(10) 0.0189(2) Uani 1 1 d . . . H6A H 0.1289 0.3379 0.4847 0.023 Uiso 1 1 calc R . . C5 C 0.14401(10) 0.33557(11) 0.31555(10) 0.0179(2) Uani 1 1 d . . . H5A H 0.2348 0.3280 0.3593 0.021 Uiso 1 1 calc R . . C2 C -0.12139(10) 0.35523(11) 0.18944(10) 0.0180(2) Uani 1 1 d . . . H2B H -0.2123 0.3612 0.1457 0.022 Uiso 1 1 calc R . . H1 H 0.2213(18) 0.3435(16) 0.1498(17) 0.045(5) Uiso 1 1 d . . . H2 H -0.1987(19) 0.3606(17) 0.3535(17) 0.049(5) Uiso 1 1 d . . . N1 N 0.63069(8) 0.36829(9) 0.28668(8) 0.0161(2) Uani 1 1 d . . . N2 N 0.39093(8) 0.35484(9) 0.21937(8) 0.0156(2) Uani 1 1 d . . . C11 C 0.55203(10) 0.43553(11) 0.15489(10) 0.0181(2) Uani 1 1 d . . . H11B H 0.5625 0.3821 0.0865 0.022 Uiso 1 1 calc R . . H11A H 0.5813 0.5348 0.1567 0.022 Uiso 1 1 calc R . . C9 C 0.46371(10) 0.42758(11) 0.34943(10) 0.0185(2) Uani 1 1 d . . . H9B H 0.4581 0.3712 0.4192 0.022 Uiso 1 1 calc R . . H9A H 0.4260 0.5228 0.3453 0.022 Uiso 1 1 calc R . . C12 C 0.60647(10) 0.44428(11) 0.38509(10) 0.0184(2) Uani 1 1 d . . . H12B H 0.6272 0.5468 0.3861 0.022 Uiso 1 1 calc R . . H12A H 0.6625 0.4049 0.4749 0.022 Uiso 1 1 calc R . . C8 C 0.40846(10) 0.43579(11) 0.11875(10) 0.0184(2) Uani 1 1 d . . . H8B H 0.3789 0.5353 0.1148 0.022 Uiso 1 1 calc R . . H8A H 0.3562 0.3920 0.0301 0.022 Uiso 1 1 calc R . . C10 C 0.58973(10) 0.21752(10) 0.27912(10) 0.0186(2) Uani 1 1 d . . . H10B H 0.6375 0.1727 0.3680 0.022 Uiso 1 1 calc R . . H10A H 0.6097 0.1642 0.2171 0.022 Uiso 1 1 calc R . . C7 C 0.44383(10) 0.20930(11) 0.23034(11) 0.0192(2) Uani 1 1 d . . . H7B H 0.4000 0.1615 0.1426 0.023 Uiso 1 1 calc R . . H7A H 0.4285 0.1522 0.2937 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0155(4) 0.0435(5) 0.0188(4) -0.0053(3) 0.0094(3) -0.0014(3) O2 0.0161(4) 0.0448(5) 0.0193(4) 0.0040(3) 0.0104(3) 0.0009(3) C1 0.0172(5) 0.0176(5) 0.0203(5) 0.0012(4) 0.0104(4) -0.0002(4) C3 0.0160(5) 0.0212(5) 0.0167(5) -0.0023(4) 0.0064(4) -0.0006(4) C4 0.0172(5) 0.0175(5) 0.0194(5) -0.0026(4) 0.0104(4) -0.0014(4) C6 0.0164(5) 0.0224(5) 0.0164(5) 0.0035(4) 0.0066(4) 0.0002(4) C5 0.0131(5) 0.0185(5) 0.0207(5) 0.0013(4) 0.0072(4) 0.0003(4) C2 0.0133(5) 0.0196(5) 0.0199(5) -0.0011(4) 0.0072(4) -0.0002(4) N1 0.0145(4) 0.0186(4) 0.0159(4) 0.0011(3) 0.0079(3) 0.0005(3) N2 0.0141(4) 0.0179(4) 0.0151(4) -0.0008(3) 0.0074(3) -0.0007(3) C11 0.0169(5) 0.0215(5) 0.0173(5) 0.0034(4) 0.0095(4) 0.0000(4) C9 0.0168(5) 0.0227(5) 0.0177(5) -0.0042(4) 0.0099(4) -0.0015(4) C12 0.0165(5) 0.0215(5) 0.0169(5) -0.0040(4) 0.0079(4) -0.0033(4) C8 0.0154(5) 0.0222(5) 0.0168(5) 0.0045(4) 0.0071(4) 0.0024(4) C10 0.0192(5) 0.0159(5) 0.0214(5) 0.0010(4) 0.0102(4) 0.0025(4) C7 0.0191(5) 0.0157(5) 0.0225(5) -0.0009(4) 0.0099(4) -0.0023(4) _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 O1 C4 1.3661(12) . ? O1 H1 0.930(19) . ? O2 C1 1.3661(12) . ? O2 H2 0.936(19) . ? C1 C6 1.3946(15) . ? C1 C2 1.3961(15) . ? C3 C4 1.3946(15) . ? C3 C2 1.3953(14) . ? C3 H3A 0.9500 . ? C4 C5 1.3988(15) . ? C6 C5 1.3941(14) . ? C6 H6A 0.9500 . ? C5 H5A 0.9500 . ? C2 H2B 0.9500 . ? N1 C12 1.4791(13) . ? N1 C11 1.4810(13) . ? N1 C10 1.4829(13) . ? N2 C8 1.4805(13) . ? N2 C9 1.4814(13) . ? N2 C7 1.4815(13) . ? C11 C8 1.5539(14) . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C9 C12 1.5539(14) . ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C12 H12B 0.9900 . ? C12 H12A 0.9900 . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? C10 C7 1.5497(14) . ? C10 H10B 0.9900 . ? C10 H10A 0.9900 . ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? 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 C4 O1 H1 111.5(10) . . ? C1 O2 H2 110.2(10) . . ? O2 C1 C6 118.18(10) . . ? O2 C1 C2 123.13(9) . . ? C6 C1 C2 118.69(10) . . ? C4 C3 C2 120.42(10) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? O1 C4 C3 118.32(9) . . ? O1 C4 C5 122.88(9) . . ? C3 C4 C5 118.80(9) . . ? C5 C6 C1 120.63(10) . . ? C5 C6 H6A 119.7 . . ? C1 C6 H6A 119.7 . . ? C6 C5 C4 120.61(9) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C3 C2 C1 120.82(10) . . ? C3 C2 H2B 119.6 . . ? C1 C2 H2B 119.6 . . ? C12 N1 C11 108.44(8) . . ? C12 N1 C10 108.78(8) . . ? C11 N1 C10 108.53(8) . . ? C8 N2 C9 108.53(8) . . ? C8 N2 C7 108.78(8) . . ? C9 N2 C7 108.70(8) . . ? N1 C11 C8 110.06(8) . . ? N1 C11 H11B 109.6 . . ? C8 C11 H11B 109.6 . . ? N1 C11 H11A 109.6 . . ? C8 C11 H11A 109.6 . . ? H11B C11 H11A 108.2 . . ? N2 C9 C12 110.05(8) . . ? N2 C9 H9B 109.7 . . ? C12 C9 H9B 109.7 . . ? N2 C9 H9A 109.7 . . ? C12 C9 H9A 109.7 . . ? H9B C9 H9A 108.2 . . ? N1 C12 C9 110.22(8) . . ? N1 C12 H12B 109.6 . . ? C9 C12 H12B 109.6 . . ? N1 C12 H12A 109.6 . . ? C9 C12 H12A 109.6 . . ? H12B C12 H12A 108.1 . . ? N2 C8 C11 110.21(8) . . ? N2 C8 H8B 109.6 . . ? C11 C8 H8B 109.6 . . ? N2 C8 H8A 109.6 . . ? C11 C8 H8A 109.6 . . ? H8B C8 H8A 108.1 . . ? N1 C10 C7 110.40(8) . . ? N1 C10 H10B 109.6 . . ? C7 C10 H10B 109.6 . . ? N1 C10 H10A 109.6 . . ? C7 C10 H10A 109.6 . . ? H10B C10 H10A 108.1 . . ? N2 C7 C10 110.01(8) . . ? N2 C7 H7B 109.7 . . ? C10 C7 H7B 109.7 . . ? N2 C7 H7A 109.7 . . ? C10 C7 H7A 109.7 . . ? H7B C7 H7A 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C3 C4 O1 178.99(9) . . . . ? C2 C3 C4 C5 -1.32(14) . . . . ? O2 C1 C6 C5 178.85(9) . . . . ? C2 C1 C6 C5 -1.41(14) . . . . ? C1 C6 C5 C4 1.28(15) . . . . ? O1 C4 C5 C6 179.77(9) . . . . ? C3 C4 C5 C6 0.10(14) . . . . ? C4 C3 C2 C1 1.19(14) . . . . ? O2 C1 C2 C3 179.91(9) . . . . ? C6 C1 C2 C3 0.18(14) . . . . ? C12 N1 C11 C8 -55.58(10) . . . . ? C10 N1 C11 C8 62.44(10) . . . . ? C8 N2 C9 C12 -55.34(10) . . . . ? C7 N2 C9 C12 62.81(10) . . . . ? C11 N1 C12 C9 62.91(10) . . . . ? C10 N1 C12 C9 -54.95(10) . . . . ? N2 C9 C12 N1 -6.48(11) . . . . ? C9 N2 C8 C11 62.66(10) . . . . ? C7 N2 C8 C11 -55.44(10) . . . . ? N1 C11 C8 N2 -6.24(11) . . . . ? C12 N1 C10 C7 62.24(11) . . . . ? C11 N1 C10 C7 -55.57(10) . . . . ? C8 N2 C7 C10 62.39(11) . . . . ? C9 N2 C7 C10 -55.61(11) . . . . ? N1 C10 C7 N2 -5.99(12) . . . . ? 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 O1 H1 N2 0.930(19) 1.782(19) 2.7017(11) 169.7(15) . O2 H2 N1 0.936(19) 1.794(19) 2.7137(12) 166.9(16) 1_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.340 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.054 # Attachment 'shelxl+25C.cif' data_298K _database_code_depnum_ccdc_archive 'CCDC 752515' #TrackingRef 'shelxl+25C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 N2, C6 H6 O2 ' _chemical_formula_sum 'C12 H18 N2 O2' _chemical_formula_weight 222.28 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc ' 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 11.951(2) _cell_length_b 9.5070(19) _cell_length_c 11.672(2) _cell_angle_alpha 90.00 _cell_angle_beta 118.95(3) _cell_angle_gamma 90.00 _cell_volume 1160.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4953 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8977 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'crystalclear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis-Rapid diffractometer' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5864 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1334 _reflns_number_gt 1007 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear (Rigaku, 2005)' _computing_cell_refinement 'crystalclear (Rigaku, 2005)' _computing_data_reduction 'crystalclear (Rigaku, 2005)' _computing_structure_solution 'SHELXtl (Sheldrick, 2008)' _computing_structure_refinement 'SHELXtl (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXtl (Sheldrick, 2008); diamond (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXtl (Sheldrick, 2008)' _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^)+(0.0612P)^2^+0.4180P] 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 SHELXL _refine_ls_extinction_coef 0.030(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1334 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 N2 N 0.38096(12) 0.36036(14) 0.21759(12) 0.0420(4) Uani 1 1 d . . . C9 C 0.45680(16) 0.4305(2) 0.34508(16) 0.0512(5) Uani 1 1 d . . . H9B H 0.4478 0.3797 0.4122 0.061 Uiso 1 1 calc R . . H9A H 0.4253 0.5254 0.3409 0.061 Uiso 1 1 calc R . . C8 C 0.40156(15) 0.43543(19) 0.11938(15) 0.0506(5) Uani 1 1 d . . . H8B H 0.3748 0.5326 0.1144 0.061 Uiso 1 1 calc R . . H8A H 0.3500 0.3927 0.0341 0.061 Uiso 1 1 calc R . . C7 C 0.42864(16) 0.21565(18) 0.22850(18) 0.0542(5) Uani 1 1 d . . . H7B H 0.3822 0.1688 0.1445 0.065 Uiso 1 1 calc R . . H7A H 0.4140 0.1640 0.2917 0.065 Uiso 1 1 calc R . . O1 O 0.12184(13) 0.34462(17) 0.10058(13) 0.0751(5) Uani 1 1 d . . . C3 C -0.06774(16) 0.34645(18) 0.11536(16) 0.0509(5) Uani 1 1 d . . . H3A H -0.1143 0.3483 0.0244 0.061 Uiso 1 1 calc R . . C5 C 0.13127(15) 0.34505(18) 0.31252(16) 0.0477(4) Uani 1 1 d . . . H5A H 0.2202 0.3441 0.3555 0.057 Uiso 1 1 calc R . . C4 C 0.06416(15) 0.34508(17) 0.17675(16) 0.0454(4) Uani 1 1 d . . . H1 H 0.214(3) 0.354(2) 0.151(3) 0.104(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 N2 0.0385(7) 0.0497(8) 0.0402(7) -0.0022(5) 0.0210(6) -0.0013(5) C9 0.0495(10) 0.0633(11) 0.0461(9) -0.0121(8) 0.0272(8) -0.0025(8) C8 0.0456(9) 0.0611(11) 0.0439(8) 0.0118(7) 0.0206(7) 0.0082(7) C7 0.0575(11) 0.0448(10) 0.0615(11) -0.0035(8) 0.0298(9) -0.0090(7) O1 0.0453(8) 0.1347(14) 0.0506(8) -0.0170(7) 0.0273(6) -0.0038(8) C3 0.0417(9) 0.0658(11) 0.0416(8) -0.0104(7) 0.0172(7) 0.0001(7) C5 0.0325(8) 0.0586(10) 0.0482(9) 0.0023(7) 0.0164(7) -0.0009(7) C4 0.0394(9) 0.0514(9) 0.0472(9) -0.0071(7) 0.0225(7) -0.0007(7) _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 N2 C8 1.469(2) . ? N2 C7 1.471(2) . ? N2 C9 1.475(2) . ? C9 C8 1.536(2) 2_655 ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? C8 C9 1.536(2) 2_655 ? C8 H8B 0.9700 . ? C8 H8A 0.9700 . ? C7 C7 1.527(3) 2_655 ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? O1 C4 1.363(2) . ? O1 H1 0.97(3) . ? C3 C5 1.380(2) 2 ? C3 C4 1.380(2) . ? C3 H3A 0.9300 . ? C5 C3 1.380(2) 2 ? C5 C4 1.387(2) . ? C5 H5A 0.9300 . ? 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 C8 N2 C7 108.53(13) . . ? C8 N2 C9 108.33(13) . . ? C7 N2 C9 108.20(13) . . ? N2 C9 C8 110.19(13) . 2_655 ? N2 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 2_655 . ? N2 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 2_655 . ? H9B C9 H9A 108.1 . . ? N2 C8 C9 110.69(12) . 2_655 ? N2 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 2_655 . ? N2 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 2_655 . ? H8B C8 H8A 108.1 . . ? N2 C7 C7 110.65(8) . 2_655 ? N2 C7 H7B 109.5 . . ? C7 C7 H7B 109.5 2_655 . ? N2 C7 H7A 109.5 . . ? C7 C7 H7A 109.5 2_655 . ? H7B C7 H7A 108.1 . . ? C4 O1 H1 113.1(15) . . ? C5 C3 C4 120.70(16) 2 . ? C5 C3 H3A 119.6 2 . ? C4 C3 H3A 119.6 . . ? C3 C5 C4 120.82(15) 2 . ? C3 C5 H5A 119.6 2 . ? C4 C5 H5A 119.6 . . ? O1 C4 C3 118.19(15) . . ? O1 C4 C5 123.35(14) . . ? C3 C4 C5 118.46(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N2 C9 C8 -56.50(16) . . . 2_655 ? C7 N2 C9 C8 60.98(17) . . . 2_655 ? C7 N2 C8 C9 -56.12(17) . . . 2_655 ? C9 N2 C8 C9 61.14(16) . . . 2_655 ? C8 N2 C7 C7 60.4(2) . . . 2_655 ? C9 N2 C7 C7 -56.9(2) . . . 2_655 ? C5 C3 C4 O1 179.12(16) 2 . . . ? C5 C3 C4 C5 -1.2(2) 2 . . . ? C3 C5 C4 O1 179.58(16) 2 . . . ? C3 C5 C4 C3 0.0(2) 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 O1 H1 N2 0.97(3) 1.76(3) 2.717(2) 170(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.199 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.039 # Attachment 'shelxl-60C.cif' data_213K _database_code_depnum_ccdc_archive 'CCDC 752516' #TrackingRef 'shelxl-60C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 N2, C6 H6 O2 ' _chemical_formula_sum 'C12 H18 N2 O2' _chemical_formula_weight 222.28 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc ' 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 11.9322(10) _cell_length_b 9.4337(9) _cell_length_c 11.5728(11) _cell_angle_alpha 90.00 _cell_angle_beta 119.001(7) _cell_angle_gamma 90.00 _cell_volume 1139.35(18) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 8016 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 27.45 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8983 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'crystalclear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis-Rapid diffractometer' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5344 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 27.44 _reflns_number_total 1297 _reflns_number_gt 1197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear (Rigaku, 2005)' _computing_cell_refinement 'crystalclear (Rigaku, 2005)' _computing_data_reduction 'crystalclear (Rigaku, 2005)' _computing_structure_solution 'SHELXtl (Sheldrick, 2008)' _computing_structure_refinement 'SHELXtl (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXtl (Sheldrick, 2008); diamond (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXtl (Sheldrick, 2008)' _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^)+(0.0724P)^2^+0.4603P] 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 1297 _refine_ls_number_parameters 77 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 C3 C -0.06893(11) 0.34652(12) 0.11341(11) 0.0338(3) Uani 1 1 d . . . H3A H -0.1165 0.3484 0.0207 0.041 Uiso 1 1 calc R . . C4 C 0.06397(11) 0.34509(11) 0.17521(11) 0.0306(3) Uani 1 1 d . . . C5 C 0.13233(11) 0.34516(12) 0.31294(11) 0.0323(3) Uani 1 1 d . . . H5A H 0.2224 0.3443 0.3563 0.039 Uiso 1 1 calc R . . C7 C 0.42778(11) 0.21428(12) 0.22698(12) 0.0362(3) Uani 1 1 d . . . H7B H 0.3816 0.1677 0.1407 0.043 Uiso 1 1 calc R . . H7A H 0.4115 0.1608 0.2900 0.043 Uiso 1 1 calc R . . C8 C 0.40110(10) 0.43790(13) 0.11769(10) 0.0325(3) Uani 1 1 d . . . H8B H 0.3750 0.5371 0.1139 0.039 Uiso 1 1 calc R . . H8A H 0.3483 0.3956 0.0303 0.039 Uiso 1 1 calc R . . C9 C 0.45631(10) 0.43122(13) 0.34620(10) 0.0321(3) Uani 1 1 d . . . H9B H 0.4476 0.3785 0.4144 0.039 Uiso 1 1 calc R . . H9A H 0.4237 0.5274 0.3424 0.039 Uiso 1 1 calc R . . N2 N 0.38047(9) 0.36087(10) 0.21688(9) 0.0280(3) Uani 1 1 d . . . O1 O 0.12128(9) 0.34438(12) 0.09805(9) 0.0482(3) Uani 1 1 d . . . H1 H 0.211(2) 0.3505(19) 0.148(2) 0.070(6) 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 C3 0.0299(6) 0.0423(6) 0.0262(5) -0.0057(4) 0.0112(4) 0.0014(4) C4 0.0297(6) 0.0336(6) 0.0306(5) -0.0050(4) 0.0161(4) -0.0021(4) C5 0.0250(5) 0.0388(6) 0.0310(6) 0.0013(4) 0.0118(4) -0.0030(4) C7 0.0436(7) 0.0281(6) 0.0373(6) -0.0032(4) 0.0200(5) -0.0072(4) C8 0.0297(5) 0.0396(6) 0.0270(5) 0.0076(4) 0.0129(4) 0.0044(4) C9 0.0317(6) 0.0397(6) 0.0281(5) -0.0079(4) 0.0170(4) -0.0023(4) N2 0.0274(5) 0.0332(5) 0.0247(4) -0.0024(3) 0.0136(4) -0.0033(3) O1 0.0305(5) 0.0856(8) 0.0317(5) -0.0103(4) 0.0175(4) -0.0044(4) _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 C3 C5 1.3872(16) 2 ? C3 C4 1.3880(17) . ? C3 H3A 0.9400 . ? C4 O1 1.3629(14) . ? C4 C5 1.3946(16) . ? C5 C3 1.3872(16) 2 ? C5 H5A 0.9400 . ? C7 N2 1.4767(15) . ? C7 C7 1.537(2) 2_655 ? C7 H7B 0.9800 . ? C7 H7A 0.9800 . ? C8 N2 1.4765(13) . ? C8 C9 1.5440(15) 2_655 ? C8 H8B 0.9800 . ? C8 H8A 0.9800 . ? C9 N2 1.4786(13) . ? C9 C8 1.5440(15) 2_655 ? C9 H9B 0.9800 . ? C9 H9A 0.9800 . ? O1 H1 0.94(2) . ? 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 C5 C3 C4 120.69(11) 2 . ? C5 C3 H3A 119.7 2 . ? C4 C3 H3A 119.7 . . ? O1 C4 C3 118.24(11) . . ? O1 C4 C5 123.20(11) . . ? C3 C4 C5 118.56(11) . . ? C3 C5 C4 120.74(10) 2 . ? C3 C5 H5A 119.6 2 . ? C4 C5 H5A 119.6 . . ? N2 C7 C7 110.41(6) . 2_655 ? N2 C7 H7B 109.6 . . ? C7 C7 H7B 109.6 2_655 . ? N2 C7 H7A 109.6 . . ? C7 C7 H7A 109.6 2_655 . ? H7B C7 H7A 108.1 . . ? N2 C8 C9 110.28(8) . 2_655 ? N2 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 2_655 . ? N2 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 2_655 . ? H8B C8 H8A 108.1 . . ? N2 C9 C8 110.22(8) . 2_655 ? N2 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 2_655 . ? N2 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 2_655 . ? H9B C9 H9A 108.1 . . ? C8 N2 C7 108.73(9) . . ? C8 N2 C9 108.37(9) . . ? C7 N2 C9 108.50(9) . . ? C4 O1 H1 112.4(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C3 C4 O1 179.03(11) 2 . . . ? C5 C3 C4 C5 -1.28(14) 2 . . . ? O1 C4 C5 C3 179.72(11) . . . 2 ? C3 C4 C5 C3 0.04(14) . . . 2 ? C9 C8 N2 C7 -55.76(11) 2_655 . . . ? C9 C8 N2 C9 61.98(10) 2_655 . . . ? C7 C7 N2 C8 61.47(14) 2_655 . . . ? C7 C7 N2 C9 -56.19(14) 2_655 . . . ? C8 C9 N2 C8 -56.17(10) 2_655 . . . ? C8 C9 N2 C7 61.72(11) 2_655 . . . ? 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 O1 H1 N2 0.94(2) 1.79(2) 2.7122(13) 170.5(19) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.211 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.095