# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'K. Vyas' _publ_contact_author_address ; Analytical Chemistry Dr Reddy's Laboratories Ltd Discovery Research Miyapur Hyderabad Andhra Pradesh 500049 INDIA ; _publ_contact_author_email VYASK@DRREDDYS.COM _publ_section_title ; Supramolecular synthon polymorphism in 2:1 co-crystal of 4-hydroxybenzoic acid and 2,3,5,6-tetramethylpyrazine ; loop_ _publ_author_name 'K. Vyas' 'Bukkapattanam R. Sreekanth' 'Vishweshwar Peddy' data_4HBA_TMP_form_1 _database_code_depnum_ccdc_archive 'CCDC 632453' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H24 N2 O6 ' _chemical_formula_moiety 'C8 H12 N2, 2(C7 H6 O3)' _chemical_formula_weight 412.44 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 13.039(7) _cell_length_b 7.401(4) _cell_length_c 22.560(12) _cell_angle_alpha 90 _cell_angle_beta 102.440(5) _cell_angle_gamma 90 _cell_volume 2125.8(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7702 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872.00 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_T_max 0.959 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 24455 _diffrn_reflns_av_R_equivalents 0.060 _diffrn_reflns_theta_max 27.51 _diffrn_measured_fraction_theta_max 0.9771 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.9771 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5150 _reflns_number_gt 1964 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1210 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 5150 _refine_ls_number_parameters 602 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 7999.9600 10996.6000 3059.0400 ; _refine_ls_shift/su_max 0.1630 _refine_diff_density_max 0.30 _refine_diff_density_min -0.31 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 291.2(27) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #=============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.6.0' _computing_molecular_graphics 'X-seed 2.0' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.8429(3) 0.6929(7) 0.5851(2) 1.000 0.0579(14) . . N2 N Uani 0.6288(3) 0.6832(7) 0.5422(2) 1.000 0.0625(14) . . C29 C Uani 0.8018(4) 0.7194(9) 0.5268(2) 1.000 0.0648(18) . . C30 C Uani 0.6948(4) 0.7163(9) 0.5053(2) 1.000 0.0641(18) . . C31 C Uani 0.6707(4) 0.6576(7) 0.6014(2) 1.000 0.0558(16) . . C32 C Uani 0.7796(3) 0.6645(8) 0.6235(2) 1.000 0.0549(14) . . C33 C Uani 0.8773(4) 0.7513(12) 0.4855(2) 1.000 0.098(3) . . C34 C Uani 0.6449(4) 0.7520(10) 0.4394(2) 1.000 0.114(4) . . C35 C Uani 0.5956(4) 0.6251(11) 0.6414(2) 1.000 0.080(2) . . C36 C Uani 0.8272(4) 0.6378(9) 0.6894(2) 1.000 0.074(2) . . N3 N Uani -0.8784(3) 0.6931(7) -0.0930(2) 1.000 0.0602(14) . . N4 N Uani -0.6641(3) 0.6722(7) -0.0529(2) 1.000 0.0624(14) . . C37 C Uani -0.8356(4) 0.6539(8) -0.0350(2) 1.000 0.0610(16) . . C38 C Uani -0.7280(4) 0.6407(8) -0.0144(2) 1.000 0.0554(16) . . C39 C Uani -0.7072(4) 0.7083(9) -0.1113(2) 1.000 0.0628(18) . . C40 C Uani -0.8152(4) 0.7166(7) -0.1317(2) 1.000 0.0559(16) . . C41 C Uani -0.9113(4) 0.6309(12) 0.0064(2) 1.000 0.092(3) . . C42 C Uani -0.6784(4) 0.6000(11) 0.0499(2) 1.000 0.085(2) . . C43 C Uani -0.6348(4) 0.7379(13) -0.1540(2) 1.000 0.099(3) . . C44 C Uani -0.8680(4) 0.7463(9) -0.1971(2) 1.000 0.077(2) . . O1 O Uani 1.5007(3) 1.4117(6) 0.7666(2) 1.000 0.0849(16) . . O2 O Uani 1.6106(3) 1.1788(6) 0.7856(2) 1.000 0.0807(14) . . O3 O Uani 1.9181(3) 1.8298(6) 0.8747(2) 1.000 0.0738(16) . . C1 C Uani 1.6785(4) 1.4711(7) 0.8126(2) 1.000 0.0528(16) . . C2 C Uani 1.7799(3) 1.4065(7) 0.8340(2) 1.000 0.0514(16) . . C3 C Uani 1.8602(4) 1.5226(9) 0.8541(2) 1.000 0.0606(18) . . C4 C Uani 1.8432(4) 1.7055(8) 0.8552(2) 1.000 0.0531(16) . . C5 C Uani 1.7415(4) 1.7748(8) 0.8338(2) 1.000 0.0575(16) . . C6 C Uani 1.6605(4) 1.6556(8) 0.8136(2) 1.000 0.0589(16) . . C7 C Uani 1.5933(4) 1.3440(7) 0.7871(2) 1.000 0.0567(17) . . O4 O Uani 0.1223(3) 0.6237(7) 0.2589(2) 1.000 0.0892(18) . . O5 O Uani 0.0061(3) 0.7217(8) 0.3100(2) 1.000 0.0946(18) . . O6 O Uani 0.4077(4) 0.7074(12) 0.5217(2) 1.000 0.113(2) . . C8 C Uani 0.1777(4) 0.6772(8) 0.3645(2) 1.000 0.0659(17) . . C9 C Uani 0.1553(4) 0.7272(9) 0.4184(3) 1.000 0.075(2) . . C10 C Uani 0.2331(4) 0.7348(11) 0.4711(3) 1.000 0.080(2) . . C11 C Uani 0.3354(4) 0.6938(11) 0.4686(3) 1.000 0.084(2) . . C12 C Uani 0.3579(4) 0.6356(11) 0.4153(3) 1.000 0.091(3) . . C13 C Uani 0.2791(4) 0.6260(10) 0.3621(3) 1.000 0.0754(19) . . C14 C Uani 0.0946(4) 0.6771(9) 0.3083(3) 1.000 0.074(2) . . O7 O Uani 1.4666(3) 0.9609(6) 0.7291(2) 1.000 0.0803(16) . . O8 O Uani 1.3556(3) 1.1932(6) 0.7130(2) 1.000 0.0769(14) . . O9 O Uani 1.0457(3) 0.5582(6) 0.6123(2) 1.000 0.0826(16) . . C15 C Uani 1.2891(3) 0.9061(8) 0.6818(2) 1.000 0.0518(14) . . C16 C Uani 1.1892(4) 0.9750(8) 0.6625(2) 1.000 0.0594(17) . . C17 C Uani 1.1056(4) 0.8624(8) 0.6389(2) 1.000 0.0632(17) . . C18 C Uani 1.1231(3) 0.6734(8) 0.6348(2) 1.000 0.0570(16) . . C19 C Uani 1.2231(4) 0.6080(7) 0.6550(2) 1.000 0.0587(17) . . C20 C Uani 1.3064(4) 0.7176(8) 0.6780(2) 1.000 0.0582(16) . . C21 C Uani 1.3733(4) 1.0266(9) 0.7096(2) 1.000 0.0584(18) . . O10 O Uani -0.1458(3) 0.7635(8) 0.2137(2) 1.000 0.0965(18) . . O11 O Uani -0.0302(3) 0.6773(8) 0.1601(2) 1.000 0.0913(18) . . O12 O Uani -0.4470(3) 0.6206(9) -0.0407(2) 1.000 0.098(2) . . C22 C Uani -0.2085(4) 0.6982(9) 0.1093(2) 1.000 0.0657(17) . . C23 C Uani -0.1873(4) 0.6402(9) 0.0550(2) 1.000 0.0707(19) . . C24 C Uani -0.2663(4) 0.6157(10) 0.0059(3) 1.000 0.079(2) . . C25 C Uani -0.3732(4) 0.6506(10) 0.0094(3) 1.000 0.076(2) . . C26 C Uani -0.3919(4) 0.7161(9) 0.0634(3) 1.000 0.077(2) . . C27 C Uani -0.3103(4) 0.7366(8) 0.1134(3) 1.000 0.0696(19) . . C28 C Uani -0.1217(4) 0.7159(8) 0.1635(3) 1.000 0.0684(19) . . H331 H Uiso 0.88570 0.87840 0.48300 1.000 0.1190 calc R H332 H Uiso 0.84870 0.70140 0.44670 1.000 0.1200 calc R H333 H Uiso 0.94330 0.69750 0.50240 1.000 0.1190 calc R H341 H Uiso 0.63550 0.64150 0.41760 1.000 0.1350 calc R H342 H Uiso 0.68930 0.82820 0.42200 1.000 0.1350 calc R H343 H Uiso 0.57890 0.81020 0.43590 1.000 0.1350 calc R H351 H Uiso 0.57710 0.73660 0.65710 1.000 0.0980 calc R H352 H Uiso 0.62850 0.54880 0.67380 1.000 0.0980 calc R H353 H Uiso 0.53410 0.56790 0.61890 1.000 0.0980 calc R H361 H Uiso 0.84220 0.51330 0.69710 1.000 0.0880 calc R H362 H Uiso 0.77940 0.67800 0.71290 1.000 0.0880 calc R H363 H Uiso 0.89060 0.70530 0.69890 1.000 0.0880 calc R H411 H Uiso -0.91900 0.74650 0.02320 1.000 0.1140 calc R H412 H Uiso -0.88220 0.54690 0.03730 1.000 0.1140 calc R H413 H Uiso -0.97750 0.59070 -0.01610 1.000 0.1140 calc R H421 H Uiso -0.66900 0.47300 0.05410 1.000 0.1030 calc R H422 H Uiso -0.72230 0.64150 0.07560 1.000 0.1020 calc R H423 H Uiso -0.61200 0.65830 0.06090 1.000 0.1030 calc R H431 H Uiso -0.62130 0.86390 -0.15510 1.000 0.1220 calc R H432 H Uiso -0.66690 0.69540 -0.19330 1.000 0.1220 calc R H433 H Uiso -0.57070 0.67550 -0.13920 1.000 0.1220 calc R H441 H Uiso -0.87690 0.63260 -0.21710 1.000 0.0910 calc R H442 H Uiso -0.82420 0.82150 -0.21520 1.000 0.0910 calc R H443 H Uiso -0.93480 0.80040 -0.19920 1.000 0.0910 calc R H2 H Uiso 1.79380 1.28060 0.83330 1.000 0.0620 calc R H3 H Uiso 1.92890 1.47700 0.86930 1.000 0.0710 calc R H5 H Uiso 1.72880 1.90120 0.83410 1.000 0.0690 calc R H6 H Uiso 1.59180 1.70270 0.79940 1.000 0.0710 calc R H101 H Uiso 1.44410 1.33390 0.74960 1.000 0.0980 calc R H103 H Uiso 1.977(3) 1.781(6) 0.886(2) 1.000 0.031(11) d . H9 H Uiso 0.08510 0.75750 0.41990 1.000 0.0920 calc R H10 H Uiso 0.21550 0.76980 0.50820 1.000 0.0970 calc R H12 H Uiso 0.42760 0.60100 0.41410 1.000 0.1100 calc R H13 H Uiso 0.29530 0.58680 0.32510 1.000 0.0900 calc R H104 H Uiso 0.07110 0.62020 0.22190 1.000 0.1070 calc R H106 H Uiso 0.471(6) 0.72(2) 0.518(4) 1.000 0.17(4) d . H16 H Uiso 1.17710 1.10100 0.66520 1.000 0.0700 calc R H17 H Uiso 1.03680 0.90930 0.62470 1.000 0.0770 calc R H19 H Uiso 1.23490 0.48150 0.65380 1.000 0.0700 calc R H20 H Uiso 1.37560 0.67140 0.69090 1.000 0.0710 calc R H107 H Uiso 1.52380 1.03620 0.74720 1.000 0.0940 calc R H109 H Uiso 0.974(6) 0.64(2) 0.612(4) 1.000 0.22(5) d . H23 H Uiso -0.11710 0.61680 0.05170 1.000 0.0860 calc R H24 H Uiso -0.25130 0.57510 -0.03130 1.000 0.0980 calc R H26 H Uiso -0.46170 0.74550 0.06610 1.000 0.0920 calc R H27 H Uiso -0.32510 0.77710 0.15060 1.000 0.0860 calc R H110 H Uiso -0.09360 0.77290 0.25010 1.000 0.1140 calc R H112 H Uiso -0.512(6) 0.64(2) -0.030(3) 1.000 0.19(4) 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 0.051(2) 0.065(3) 0.057(2) -0.006(2) 0.010(2) -0.009(2) N2 0.061(2) 0.077(3) 0.050(2) 0.003(2) 0.013(2) 0.004(2) C29 0.058(3) 0.086(4) 0.047(2) 0.002(3) 0.004(2) -0.002(3) C30 0.078(3) 0.081(4) 0.032(2) 0.000(3) 0.009(2) -0.008(3) C31 0.071(3) 0.056(3) 0.042(2) 0.006(2) 0.016(2) 0.001(3) C32 0.052(2) 0.067(3) 0.046(2) -0.010(3) 0.011(2) -0.004(3) C33 0.092(4) 0.145(8) 0.062(3) 0.003(4) 0.028(3) -0.029(5) C34 0.086(4) 0.203(10) 0.050(3) 0.031(5) 0.007(3) -0.004(6) C35 0.060(3) 0.114(6) 0.072(3) 0.003(4) 0.026(2) 0.000(4) C36 0.080(3) 0.093(5) 0.047(2) 0.002(3) 0.011(2) 0.002(4) N3 0.065(2) 0.061(3) 0.056(2) -0.005(2) 0.016(2) -0.003(2) N4 0.063(2) 0.077(3) 0.049(2) -0.003(2) 0.016(2) 0.001(2) C37 0.076(3) 0.060(3) 0.050(2) -0.002(2) 0.020(2) -0.017(3) C38 0.061(3) 0.058(3) 0.047(2) -0.001(2) 0.011(2) -0.005(3) C39 0.059(3) 0.086(4) 0.045(2) 0.002(3) 0.015(2) 0.007(3) C40 0.065(3) 0.053(3) 0.050(2) -0.004(2) 0.013(2) 0.006(3) C41 0.079(3) 0.131(7) 0.074(3) 0.016(4) 0.034(3) -0.011(5) C42 0.080(3) 0.122(6) 0.054(3) 0.012(4) 0.017(2) -0.008(4) C43 0.091(4) 0.157(8) 0.057(3) 0.004(4) 0.031(3) -0.005(5) C44 0.095(4) 0.082(5) 0.050(3) 0.006(3) 0.009(3) 0.017(4) O1 0.049(2) 0.084(3) 0.112(3) -0.010(3) -0.004(2) 0.000(2) O2 0.066(2) 0.054(2) 0.112(3) 0.001(2) -0.003(2) -0.002(2) O3 0.056(2) 0.067(3) 0.090(3) -0.013(2) -0.003(2) -0.005(2) C1 0.067(3) 0.051(3) 0.045(2) -0.001(2) 0.022(2) 0.001(2) C2 0.041(2) 0.050(3) 0.063(3) 0.004(2) 0.011(2) 0.011(2) C3 0.040(2) 0.081(4) 0.057(3) -0.010(3) 0.002(2) 0.006(3) C4 0.056(3) 0.057(3) 0.045(2) -0.008(2) 0.008(2) 0.001(2) C5 0.067(3) 0.052(3) 0.054(2) -0.002(2) 0.014(2) 0.010(3) C6 0.049(2) 0.075(4) 0.053(2) -0.012(3) 0.012(2) 0.003(3) C7 0.053(3) 0.052(3) 0.063(3) -0.004(3) 0.008(2) -0.005(2) O4 0.073(2) 0.110(4) 0.085(3) 0.007(3) 0.018(2) 0.005(3) O5 0.064(2) 0.118(4) 0.100(3) -0.014(3) 0.014(2) -0.001(3) O6 0.077(3) 0.179(6) 0.079(3) 0.007(4) 0.008(2) 0.011(4) C8 0.054(3) 0.059(3) 0.082(3) 0.000(3) 0.009(2) -0.010(3) C9 0.066(3) 0.074(4) 0.089(4) 0.015(4) 0.023(3) 0.000(3) C10 0.074(4) 0.095(5) 0.073(3) 0.006(4) 0.019(3) 0.005(4) C11 0.070(3) 0.090(5) 0.088(4) 0.023(4) 0.008(3) -0.001(4) C12 0.063(3) 0.109(6) 0.104(5) 0.008(5) 0.024(3) 0.005(4) C13 0.064(3) 0.086(4) 0.076(3) -0.006(3) 0.015(3) -0.005(3) C14 0.065(3) 0.058(4) 0.101(4) 0.006(3) 0.020(3) -0.014(3) O7 0.058(2) 0.068(3) 0.110(3) -0.002(3) 0.007(2) 0.001(2) O8 0.066(2) 0.056(2) 0.101(3) -0.004(2) 0.001(2) 0.002(2) O9 0.071(2) 0.072(3) 0.104(3) -0.033(3) 0.017(2) -0.016(2) C15 0.030(2) 0.077(3) 0.044(2) 0.000(2) -0.002(2) 0.004(2) C16 0.063(3) 0.051(3) 0.060(3) -0.004(3) 0.004(2) -0.004(3) C17 0.072(3) 0.057(3) 0.064(3) 0.005(3) 0.022(2) -0.003(3) C18 0.045(2) 0.065(3) 0.062(3) -0.004(3) 0.014(2) 0.004(3) C19 0.059(3) 0.045(3) 0.070(3) -0.005(3) 0.009(2) 0.001(2) C20 0.061(3) 0.057(3) 0.058(2) 0.000(3) 0.016(2) 0.009(3) C21 0.049(3) 0.081(4) 0.046(2) 0.009(3) 0.012(2) 0.004(3) O10 0.071(2) 0.123(4) 0.090(3) -0.006(3) 0.005(2) 0.020(3) O11 0.055(2) 0.121(4) 0.099(3) 0.000(3) 0.019(2) -0.004(3) O12 0.061(2) 0.144(5) 0.086(3) 0.000(3) 0.012(2) 0.010(3) C22 0.058(3) 0.062(3) 0.079(3) 0.015(3) 0.019(2) -0.005(3) C23 0.059(3) 0.077(4) 0.079(3) 0.025(3) 0.021(3) 0.001(3) C24 0.074(3) 0.100(5) 0.072(3) 0.018(4) 0.035(3) 0.008(4) C25 0.058(3) 0.086(5) 0.086(4) 0.006(4) 0.017(3) 0.007(3) C26 0.047(3) 0.084(4) 0.100(4) -0.005(4) 0.014(3) 0.019(3) C27 0.072(3) 0.066(4) 0.077(3) -0.002(3) 0.030(3) 0.014(3) C28 0.073(3) 0.046(3) 0.089(4) 0.007(3) 0.024(3) -0.008(3) # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.297(7) . . no O2 C7 1.245(7) . . no O3 C4 1.345(7) . . no O1 H101 0.9500 . . no O3 H103 0.84(4) . . no O4 C14 1.305(8) . . no O5 C14 1.209(7) . . no O6 C11 1.359(8) . . no O4 H104 0.9500 . . no O6 H106 0.85(9) . . no O7 C21 1.296(7) . . no O8 C21 1.260(8) . . no O9 C18 1.335(7) . . no O7 H107 0.9500 . . no O9 H109 1.11(11) . . no N1 C29 1.324(6) . . no N1 C32 1.336(6) . . no N2 C31 1.343(6) . . no N2 C30 1.343(7) . . no O10 C28 1.288(8) . . no O11 C28 1.245(7) . . no O12 C25 1.336(8) . . no O10 H110 0.9500 . . no O12 H112 0.94(9) . . no N3 C40 1.335(7) . . no N3 C37 1.339(6) . . no N4 C38 1.347(7) . . no N4 C39 1.343(6) . . no C29 C30 1.375(7) . . no C29 C33 1.513(7) . . no C30 C34 1.512(6) . . no C31 C32 1.401(7) . . no C31 C35 1.487(7) . . no C32 C36 1.496(6) . . no C33 H332 0.9500 . . no C33 H331 0.9500 . . no C33 H333 0.9500 . . no C34 H341 0.9500 . . no C34 H343 0.9500 . . no C34 H342 0.9500 . . no C35 H351 0.9500 . . no C35 H352 0.9500 . . no C35 H353 0.9500 . . no C36 H362 0.9500 . . no C36 H361 0.9500 . . no C36 H363 0.9500 . . no C37 C38 1.383(7) . . no C37 C41 1.508(7) . . no C38 C42 1.486(7) . . no C39 C40 1.385(7) . . no C39 C43 1.503(7) . . no C40 C44 1.504(6) . . no C41 H411 0.9500 . . no C41 H412 0.9500 . . no C41 H413 0.9500 . . no C42 H421 0.9500 . . no C42 H423 0.9500 . . no C42 H422 0.9500 . . no C43 H431 0.9500 . . no C43 H432 0.9500 . . no C43 H433 0.9500 . . no C44 H441 0.9500 . . no C44 H443 0.9500 . . no C44 H442 0.9500 . . no C1 C2 1.391(7) . . no C1 C6 1.387(8) . . no C1 C7 1.475(7) . . no C2 C3 1.355(7) . . no C3 C4 1.373(9) . . no C4 C5 1.407(8) . . no C5 C6 1.376(8) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C8 C14 1.480(8) . . no C8 C13 1.388(8) . . no C8 C9 1.362(8) . . no C9 C10 1.388(9) . . no C10 C11 1.381(8) . . no C11 C12 1.367(9) . . no C12 C13 1.404(9) . . no C9 H9 0.9500 . . no C10 H10 0.9500 . . no C12 H12 0.9500 . . no C13 H13 0.9500 . . no C15 C21 1.448(8) . . no C15 C20 1.419(8) . . no C15 C16 1.379(7) . . no C16 C17 1.384(8) . . no C17 C18 1.424(8) . . no C18 C19 1.373(7) . . no C19 C20 1.365(8) . . no C16 H16 0.9500 . . no C17 H17 0.9500 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C22 C28 1.482(8) . . no C22 C23 1.381(7) . . no C22 C27 1.380(8) . . no C23 C24 1.353(8) . . no C24 C25 1.436(8) . . no C25 C26 1.381(9) . . no C26 C27 1.382(9) . . no C23 H23 0.9500 . . no C24 H24 0.9500 . . no C26 H26 0.9500 . . no C27 H27 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H101 120.00 . . . no C4 O3 H103 111(3) . . . no C14 O4 H104 119.00 . . . no C11 O6 H106 115(6) . . . no C21 O7 H107 121.00 . . . no C18 O9 H109 103(6) . . . no C29 N1 C32 119.6(4) . . . no C30 N2 C31 117.7(4) . . . no C28 O10 H110 121.00 . . . no C25 O12 H112 106(5) . . . no C37 N3 C40 118.8(4) . . . no C38 N4 C39 118.7(4) . . . no C30 C29 C33 122.1(4) . . . no N1 C29 C33 117.2(4) . . . no N1 C29 C30 120.7(5) . . . no N2 C30 C34 116.4(4) . . . no N2 C30 C29 121.4(4) . . . no C29 C30 C34 122.2(4) . . . no C32 C31 C35 122.6(4) . . . no N2 C31 C32 120.9(4) . . . no N2 C31 C35 116.5(4) . . . no N1 C32 C36 118.9(4) . . . no N1 C32 C31 119.7(4) . . . no C31 C32 C36 121.4(4) . . . no H331 C33 H332 111.00 . . . no C29 C33 H332 109.00 . . . no C29 C33 H333 110.00 . . . no C29 C33 H331 107.00 . . . no H332 C33 H333 110.00 . . . no H331 C33 H333 109.00 . . . no H341 C34 H343 110.00 . . . no C30 C34 H343 111.00 . . . no H342 C34 H343 109.00 . . . no C30 C34 H342 110.00 . . . no C30 C34 H341 110.00 . . . no H341 C34 H342 109.00 . . . no H351 C35 H353 109.00 . . . no H352 C35 H353 110.00 . . . no C31 C35 H352 108.00 . . . no C31 C35 H351 110.00 . . . no H351 C35 H352 110.00 . . . no C31 C35 H353 110.00 . . . no H361 C36 H363 110.00 . . . no C32 C36 H363 108.00 . . . no H362 C36 H363 111.00 . . . no C32 C36 H361 110.00 . . . no H361 C36 H362 110.00 . . . no C32 C36 H362 109.00 . . . no N3 C37 C38 121.5(4) . . . no C38 C37 C41 122.4(4) . . . no N3 C37 C41 116.1(4) . . . no N4 C38 C37 119.7(4) . . . no C37 C38 C42 122.6(4) . . . no N4 C38 C42 117.7(5) . . . no N4 C39 C43 118.0(4) . . . no C40 C39 C43 121.0(4) . . . no N4 C39 C40 121.0(4) . . . no C39 C40 C44 123.4(4) . . . no N3 C40 C44 116.4(4) . . . no N3 C40 C39 120.2(4) . . . no C37 C41 H412 108.00 . . . no C37 C41 H413 110.00 . . . no H411 C41 H413 109.00 . . . no C37 C41 H411 107.00 . . . no H411 C41 H412 111.00 . . . no H412 C41 H413 111.00 . . . no H421 C42 H423 109.00 . . . no H421 C42 H422 110.00 . . . no C38 C42 H422 110.00 . . . no H422 C42 H423 109.00 . . . no C38 C42 H423 110.00 . . . no C38 C42 H421 109.00 . . . no H432 C43 H433 110.00 . . . no H431 C43 H432 110.00 . . . no C39 C43 H431 108.00 . . . no H431 C43 H433 109.00 . . . no C39 C43 H432 110.00 . . . no C39 C43 H433 109.00 . . . no C40 C44 H441 109.00 . . . no H442 C44 H443 111.00 . . . no C40 C44 H442 108.00 . . . no H441 C44 H443 109.00 . . . no H441 C44 H442 110.00 . . . no C40 C44 H443 109.00 . . . no C6 C1 C7 121.2(5) . . . no C2 C1 C7 119.7(5) . . . no C2 C1 C6 119.0(5) . . . no C1 C2 C3 120.4(5) . . . no C2 C3 C4 121.0(5) . . . no O3 C4 C5 115.3(5) . . . no O3 C4 C3 124.9(5) . . . no C3 C4 C5 119.8(5) . . . no C4 C5 C6 118.7(5) . . . no C1 C6 C5 121.1(5) . . . no O1 C7 C1 117.3(5) . . . no O1 C7 O2 122.0(5) . . . no O2 C7 C1 120.8(5) . . . no C1 C2 H2 120.00 . . . no C3 C2 H2 119.00 . . . no C4 C3 H3 119.00 . . . no C2 C3 H3 120.00 . . . no C6 C5 H5 121.00 . . . no C4 C5 H5 121.00 . . . no C1 C6 H6 120.00 . . . no C5 C6 H6 118.00 . . . no C13 C8 C14 119.6(5) . . . no C9 C8 C14 120.5(5) . . . no C9 C8 C13 119.9(5) . . . no C8 C9 C10 121.2(5) . . . no C9 C10 C11 119.4(6) . . . no O6 C11 C12 124.0(5) . . . no C10 C11 C12 119.8(6) . . . no O6 C11 C10 116.1(6) . . . no C11 C12 C13 120.8(5) . . . no C8 C13 C12 118.8(6) . . . no O4 C14 C8 116.5(5) . . . no O5 C14 C8 120.0(6) . . . no O4 C14 O5 123.5(6) . . . no C8 C9 H9 119.00 . . . no C10 C9 H9 119.00 . . . no C9 C10 H10 120.00 . . . no C11 C10 H10 121.00 . . . no C13 C12 H12 119.00 . . . no C11 C12 H12 120.00 . . . no C8 C13 H13 121.00 . . . no C12 C13 H13 120.00 . . . no C16 C15 C21 119.0(5) . . . no C20 C15 C21 121.1(4) . . . no C16 C15 C20 119.8(5) . . . no C15 C16 C17 120.7(5) . . . no C16 C17 C18 119.5(5) . . . no O9 C18 C19 119.1(5) . . . no O9 C18 C17 122.3(4) . . . no C17 C18 C19 118.6(5) . . . no C18 C19 C20 122.5(5) . . . no C15 C20 C19 118.9(5) . . . no O7 C21 O8 121.2(5) . . . no O7 C21 C15 119.0(6) . . . no O8 C21 C15 119.8(5) . . . no C17 C16 H16 119.00 . . . no C15 C16 H16 120.00 . . . no C16 C17 H17 121.00 . . . no C18 C17 H17 119.00 . . . no C20 C19 H19 118.00 . . . no C18 C19 H19 119.00 . . . no C19 C20 H20 122.00 . . . no C15 C20 H20 119.00 . . . no C23 C22 C28 119.7(5) . . . no C27 C22 C28 120.1(5) . . . no C23 C22 C27 120.2(5) . . . no C22 C23 C24 120.4(5) . . . no C23 C24 C25 120.5(6) . . . no O12 C25 C24 117.0(6) . . . no C24 C25 C26 118.0(6) . . . no O12 C25 C26 125.0(5) . . . no C25 C26 C27 120.5(5) . . . no C22 C27 C26 120.3(6) . . . no O11 C28 C22 120.0(6) . . . no O10 C28 O11 122.4(6) . . . no O10 C28 C22 117.5(5) . . . no C22 C23 H23 120.00 . . . no C24 C23 H23 119.00 . . . no C23 C24 H24 120.00 . . . no C25 C24 H24 119.00 . . . no C25 C26 H26 119.00 . . . no C27 C26 H26 120.00 . . . no C22 C27 H27 120.00 . . . no C26 C27 H27 119.00 . . . no 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 C32 N1 C29 C30 -0.6(9) . . . . no C32 N1 C29 C33 179.9(6) . . . . no C29 N1 C32 C31 1.9(9) . . . . no C29 N1 C32 C36 -179.0(6) . . . . no C31 N2 C30 C29 1.7(9) . . . . no C31 N2 C30 C34 -177.6(5) . . . . no C30 N2 C31 C32 -0.3(8) . . . . no C30 N2 C31 C35 178.7(6) . . . . no C37 N3 C40 C39 -2.8(8) . . . . no C40 N3 C37 C38 1.2(9) . . . . no C40 N3 C37 C41 179.4(6) . . . . no C37 N3 C40 C44 175.5(5) . . . . no C38 N4 C39 C43 -178.3(6) . . . . no C39 N4 C38 C37 -2.8(9) . . . . no C39 N4 C38 C42 179.6(6) . . . . no C38 N4 C39 C40 1.2(9) . . . . no N1 C29 C30 C34 178.0(6) . . . . no C33 C29 C30 N2 178.3(6) . . . . no C33 C29 C30 C34 -2.5(10) . . . . no N1 C29 C30 N2 -1.3(10) . . . . no N2 C31 C32 N1 -1.5(8) . . . . no C35 C31 C32 N1 179.5(6) . . . . no C35 C31 C32 C36 0.5(9) . . . . no N2 C31 C32 C36 179.5(5) . . . . no N3 C37 C38 N4 1.7(9) . . . . no N3 C37 C38 C42 179.1(6) . . . . no C41 C37 C38 N4 -176.4(6) . . . . no C41 C37 C38 C42 1.0(10) . . . . no N4 C39 C40 N3 1.7(9) . . . . no N4 C39 C40 C44 -176.5(6) . . . . no C43 C39 C40 N3 -178.8(6) . . . . no C43 C39 C40 C44 3.0(10) . . . . no C6 C1 C2 C3 -1.6(7) . . . . no C7 C1 C2 C3 175.9(4) . . . . no C2 C1 C6 C5 1.8(7) . . . . no C7 C1 C6 C5 -175.8(4) . . . . no C2 C1 C7 O1 -178.6(4) . . . . no C2 C1 C7 O2 1.5(7) . . . . no C6 C1 C7 O1 -1.1(7) . . . . no C6 C1 C7 O2 178.9(5) . . . . no C1 C2 C3 C4 1.6(7) . . . . no C2 C3 C4 O3 179.6(5) . . . . no C2 C3 C4 C5 -1.6(7) . . . . no O3 C4 C5 C6 -179.4(4) . . . . no C3 C4 C5 C6 1.7(7) . . . . no C4 C5 C6 C1 -1.8(7) . . . . no C13 C8 C9 C10 2.5(10) . . . . no C14 C8 C9 C10 -177.5(6) . . . . no C9 C8 C13 C12 -3.1(10) . . . . no C14 C8 C13 C12 176.9(6) . . . . no C9 C8 C14 O4 -178.6(6) . . . . no C9 C8 C14 O5 0.0(10) . . . . no C13 C8 C14 O4 1.4(9) . . . . no C13 C8 C14 O5 -179.9(7) . . . . no C8 C9 C10 C11 1.1(11) . . . . no C9 C10 C11 O6 178.8(7) . . . . no C9 C10 C11 C12 -4.0(12) . . . . no O6 C11 C12 C13 -179.7(8) . . . . no C10 C11 C12 C13 3.4(12) . . . . no C11 C12 C13 C8 0.2(11) . . . . no C20 C15 C16 C17 -0.6(7) . . . . no C21 C15 C16 C17 -176.3(4) . . . . no C16 C15 C20 C19 0.2(7) . . . . no C21 C15 C20 C19 175.8(4) . . . . no C16 C15 C21 O7 178.3(4) . . . . no C16 C15 C21 O8 -3.6(7) . . . . no C20 C15 C21 O7 2.7(7) . . . . no C20 C15 C21 O8 -179.2(4) . . . . no C15 C16 C17 C18 0.3(7) . . . . no C16 C17 C18 O9 -179.8(4) . . . . no C16 C17 C18 C19 0.5(7) . . . . no O9 C18 C19 C20 179.3(4) . . . . no C17 C18 C19 C20 -1.0(7) . . . . no C18 C19 C20 C15 0.6(7) . . . . no C27 C22 C23 C24 -1.9(10) . . . . no C28 C22 C23 C24 177.0(6) . . . . no C23 C22 C27 C26 0.5(10) . . . . no C28 C22 C27 C26 -178.4(6) . . . . no C23 C22 C28 O10 -177.3(6) . . . . no C23 C22 C28 O11 -0.5(9) . . . . no C27 C22 C28 O10 1.6(9) . . . . no C27 C22 C28 O11 178.4(6) . . . . no C22 C23 C24 C25 0.4(11) . . . . no C23 C24 C25 O12 -179.0(7) . . . . no C23 C24 C25 C26 2.5(11) . . . . no O12 C25 C26 C27 177.8(7) . . . . no C24 C25 C26 C27 -3.8(10) . . . . no C25 C26 C27 C22 2.4(10) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H101 O8 0.9500 1.6400 2.583(6) 172.00 . yes O3 H103 N3 0.84(4) 1.95(4) 2.786(6) 173(4) 1_866 yes O4 H104 O11 0.9500 1.7500 2.678(6) 163.00 . yes O6 H106 N2 0.85(9) 2.03(8) 2.825(7) 155(11) . yes O7 H107 O2 0.9500 1.6500 2.592(6) 171.00 . yes O9 H109 N1 1.11(11) 1.73(9) 2.768(6) 153(10) . yes O10 H110 O5 0.9500 1.7000 2.624(6) 162.00 . yes O12 H112 N4 0.94(9) 1.95(8) 2.811(6) 151(7) . yes #============================================================================== # End of CIF #============================================================================== # Attachment '4HBA_TMP_Form2.cif' data_4HBA_TMP_form_2 _database_code_depnum_ccdc_archive 'CCDC 632454' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H24 N2 O6 ' _chemical_formula_moiety 'C8 H12 N2, 2(C7 H6 O3)' _chemical_formula_weight 412.44 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 10.5495(11) _cell_length_b 10.3154(9) _cell_length_c 10.2205(11) _cell_angle_alpha 90 _cell_angle_beta 109.904(4) _cell_angle_gamma 90 _cell_volume 1045.8(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3714 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436.00 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.986 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 12161 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.9835 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.9835 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2371 _reflns_number_gt 1382 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.0740 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2371 _refine_ls_number_parameters 155 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 2621.9300 3565.3300 955.7050 ; _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.31 _refine_diff_density_min -0.32 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 72.4(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #=============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.6.0' _computing_molecular_graphics 'X-Seed 2.0' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.4586(2) 0.1084(2) 0.4201(2) 1.000 0.0450(5) . . C8 C Uani 0.4152(2) -0.0083(2) 0.3674(2) 1.000 0.0445(6) . . C9 C Uani 0.4568(2) -0.1194(2) 0.4478(2) 1.000 0.0434(6) . . C10 C Uani 0.3201(2) -0.0130(2) 0.2197(2) 1.000 0.0703(10) . . C11 C Uani 0.4137(2) -0.2526(2) 0.3942(2) 1.000 0.0603(8) . . O1 O Uani 0.35820(10) 0.3258(2) 0.2732(2) 1.000 0.0574(5) . . O2 O Uani 0.24745(13) 0.33630(10) 0.42240(10) 1.000 0.0527(5) . . O3 O Uani -0.0336(2) 0.7861(2) -0.0030(2) 1.000 0.0592(6) . . C1 C Uani 0.1904(2) 0.4857(2) 0.2347(2) 1.000 0.0393(6) . . C2 C Uani 0.0998(2) 0.5532(2) 0.2805(2) 1.000 0.0438(6) . . C3 C Uani 0.0246(2) 0.6539(2) 0.2030(2) 1.000 0.0457(6) . . C4 C Uani 0.0404(2) 0.6890(2) 0.0785(2) 1.000 0.0445(6) . . C5 C Uani 0.1329(2) 0.6242(2) 0.0332(2) 1.000 0.0490(7) . . C6 C Uani 0.2069(2) 0.5234(2) 0.1101(2) 1.000 0.0458(6) . . C7 C Uani 0.2658(2) 0.3770(2) 0.3174(2) 1.000 0.0416(6) . . H101 H Uiso 0.36980 -0.02160 0.15820 1.000 0.0790 calc R H102 H Uiso 0.26170 -0.08540 0.20900 1.000 0.0790 calc R H103 H Uiso 0.26820 0.06440 0.19860 1.000 0.0790 calc R H111 H Uiso 0.47640 -0.28680 0.35510 1.000 0.0730 calc R H112 H Uiso 0.41130 -0.30640 0.46880 1.000 0.0730 calc R H113 H Uiso 0.32660 -0.24970 0.32510 1.000 0.0730 calc R H1 H Uiso 0.388(3) 0.238(3) 0.324(3) 1.000 0.128(11) d . H2 H Uiso 0.08860 0.52920 0.36560 1.000 0.0540 calc R H3 H Uiso -0.03700 0.69990 0.23530 1.000 0.0570 calc R H5 H Uiso 0.14610 0.65020 -0.05040 1.000 0.0620 calc R H6 H Uiso 0.26900 0.47790 0.07800 1.000 0.0580 calc R H30 H Uiso -0.100(3) 0.812(3) 0.028(3) 1.000 0.105(10) 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 0.0439(9) 0.0437(9) 0.0478(9) 0.0052(7) 0.0162(7) 0.0043(7) C8 0.0419(10) 0.0490(11) 0.0410(10) 0.0016(9) 0.0122(8) 0.0031(9) C9 0.0368(9) 0.0461(11) 0.0476(11) 0.0000(9) 0.0147(8) 0.0009(8) C10 0.075(2) 0.070(2) 0.0512(13) 0.0005(12) 0.0026(11) 0.0043(13) C11 0.0610(10) 0.0475(12) 0.072(2) -0.0073(11) 0.0221(11) -0.0038(10) O1 0.0599(9) 0.0570(9) 0.0651(10) 0.0163(8) 0.0342(7) 0.0185(7) O2 0.0506(8) 0.0622(9) 0.0478(8) 0.0103(7) 0.0199(6) 0.0043(7) O3 0.0647(10) 0.0622(10) 0.0606(9) 0.0203(8) 0.0342(8) 0.0216(8) C1 0.0359(9) 0.0401(10) 0.0411(10) -0.0019(8) 0.0119(7) -0.0034(7) C2 0.0469(10) 0.0491(11) 0.0377(9) 0.0004(8) 0.0174(8) 0.0006(9) C3 0.0454(10) 0.0510(11) 0.0451(10) 0.0002(9) 0.0211(8) 0.0077(9) C4 0.0423(10) 0.0456(11) 0.0471(11) 0.0034(9) 0.0170(8) 0.0020(9) C5 0.0518(11) 0.0575(12) 0.0443(11) 0.0085(10) 0.0251(9) 0.0041(10) C6 0.0441(10) 0.0503(11) 0.0500(11) 0.0029(9) 0.0250(9) 0.0042(9) C7 0.0389(10) 0.0444(11) 0.0427(10) -0.0023(8) 0.0153(8) -0.0064(8) # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.316(3) . . no O2 C7 1.228(2) . . no O3 C4 1.365(3) . . no O1 H1 1.04(3) . . no O3 H30 0.90(3) . . no N1 C9 1.346(3) . 3_656 no N1 C8 1.335(3) . . no C8 C9 1.391(3) . . no C8 C10 1.502(3) . . no C9 C11 1.492(3) . . no C10 H101 0.9500 . . no C10 H103 0.9500 . . no C10 H102 0.9500 . . no C11 H112 0.9500 . . no C11 H113 0.9500 . . no C11 H111 0.9500 . . no C1 C7 1.465(3) . . no C1 C2 1.386(3) . . no C1 C6 1.398(3) . . no C2 C3 1.381(3) . . no C3 C4 1.387(3) . . no C4 C5 1.386(3) . . no C5 C6 1.375(3) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 108.2(18) . . . no C4 O3 H30 110.7(19) . . . no C8 N1 C9 120.01(19) . . 3_656 no C9 C8 C10 122.37(18) . . . no N1 C8 C10 117.05(18) . . . no N1 C8 C9 120.58(19) . . . no N1 C9 C8 119.41(19) 3_656 . . no N1 C9 C11 117.46(18) 3_656 . . no C8 C9 C11 123.12(18) . . . no C8 C10 H103 110.00 . . . no C8 C10 H101 110.00 . . . no C8 C10 H102 109.00 . . . no H102 C10 H103 109.00 . . . no H101 C10 H102 109.00 . . . no H101 C10 H103 109.00 . . . no C9 C11 H111 109.00 . . . no H111 C11 H112 109.00 . . . no C9 C11 H112 109.00 . . . no C9 C11 H113 110.00 . . . no H112 C11 H113 109.00 . . . no H111 C11 H113 110.00 . . . no C2 C1 C7 119.40(18) . . . no C6 C1 C7 121.80(19) . . . no C2 C1 C6 118.81(19) . . . no C1 C2 C3 120.76(19) . . . no C2 C3 C4 119.8(2) . . . no O3 C4 C3 122.0(2) . . . no C3 C4 C5 119.93(19) . . . no O3 C4 C5 118.13(19) . . . no C4 C5 C6 120.07(19) . . . no C1 C6 C5 120.6(2) . . . no O2 C7 C1 123.36(19) . . . no O1 C7 O2 121.22(19) . . . no O1 C7 C1 115.41(18) . . . no C1 C2 H2 120.00 . . . no C3 C2 H2 120.00 . . . no C2 C3 H3 120.00 . . . no C4 C3 H3 120.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C1 C6 H6 119.00 . . . no C5 C6 H6 120.00 . . . no 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 C9 N1 C8 C9 -0.1(3) 3_656 . . . no C9 N1 C8 C10 179.5(2) 3_656 . . . no C8 N1 C9 C8 0.1(3) . . 3_656 3_656 no C8 N1 C9 C11 -179.0(2) . . 3_656 3_656 no N1 C8 C9 C11 -179.0(2) . . . . no N1 C8 C9 N1 0.1(3) . . . 3_656 no C10 C8 C9 C11 1.5(3) . . . . no C10 C8 C9 N1 -179.5(2) . . . 3_656 no C6 C1 C2 C3 1.6(3) . . . . no C7 C1 C2 C3 -178.3(2) . . . . no C2 C1 C6 C5 -1.1(3) . . . . no C7 C1 C6 C5 178.7(2) . . . . no C2 C1 C7 O1 -174.15(19) . . . . no C2 C1 C7 O2 4.6(3) . . . . no C6 C1 C7 O1 6.0(3) . . . . no C6 C1 C7 O2 -175.21(19) . . . . no C1 C2 C3 C4 -0.6(3) . . . . no C2 C3 C4 O3 178.7(2) . . . . no C2 C3 C4 C5 -0.9(3) . . . . no O3 C4 C5 C6 -178.2(2) . . . . no C3 C4 C5 C6 1.4(3) . . . . no C4 C5 C6 C1 -0.4(3) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 N1 1.04(3) 1.68(3) 2.706(3) 171(2) . yes O3 H30 O2 0.90(3) 1.81(3) 2.702(3) 170(3) 2_555 yes #============================================================================== # End of CIF #==============================================================================