# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11095_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Ethenzamide hydrochloride salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 Cl N O2' _chemical_formula_weight 201.65 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' Cl Cl 0.1484 0.1585 '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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5611(6) _cell_length_b 14.9501(11) _cell_length_c 10.3894(6) _cell_angle_alpha 90.00 _cell_angle_beta 123.740(4) _cell_angle_gamma 90.00 _cell_volume 976.60(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7822 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.14 _exptl_crystal_description Needles _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.358 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.8330 _exptl_absorpt_correction_T_max 0.8941 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10823 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 27.14 _reflns_number_total 2168 _reflns_number_gt 1998 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0386P)^2^+0.3135P] 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 2168 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 O11 O -0.34171(14) 0.14391(5) 0.30592(10) 0.02462(19) Uani 1 1 d . . . O21 O -0.17597(13) -0.10446(5) 0.51635(9) 0.02182(18) Uani 1 1 d . . . N11 N -0.29806(15) -0.00191(7) 0.27458(11) 0.0221(2) Uani 1 1 d . . . C1 C -0.25855(16) 0.04870(7) 0.51242(12) 0.0179(2) Uani 1 1 d . . . C6 C -0.28466(17) 0.12247(8) 0.58387(13) 0.0208(2) Uani 1 1 d . . . C5 C -0.26193(18) 0.11355(8) 0.72464(13) 0.0236(2) Uani 1 1 d . . . C4 C -0.20836(17) 0.03079(8) 0.79752(13) 0.0240(2) Uani 1 1 d . . . C3 C -0.17688(17) -0.04287(8) 0.73140(13) 0.0225(2) Uani 1 1 d . . . C2 C -0.20347(16) -0.03495(7) 0.58813(12) 0.0191(2) Uani 1 1 d . . . C11 C -0.29927(16) 0.06255(7) 0.35825(12) 0.0185(2) Uani 1 1 d . . . C21 C -0.15957(19) -0.19460(7) 0.57434(14) 0.0230(2) Uani 1 1 d . . . C22 C -0.1593(2) -0.25656(8) 0.46010(15) 0.0276(3) Uani 1 1 d . . . Cl1 Cl -0.41318(5) 0.139630(18) 0.00510(3) 0.02621(10) Uani 1 1 d . . . H21B H -0.282(2) -0.2064(9) 0.5802(15) 0.024(3) Uiso 1 1 d . . . H21A H -0.029(2) -0.2003(9) 0.6769(16) 0.024(3) Uiso 1 1 d . . . H6 H -0.322(2) 0.1755(10) 0.5335(16) 0.024(3) Uiso 1 1 d . . . H3 H -0.135(2) -0.0971(10) 0.7822(17) 0.026(3) Uiso 1 1 d . . . H22C H -0.162(2) -0.3195(11) 0.4905(18) 0.035(4) Uiso 1 1 d . . . H4 H -0.195(2) 0.0248(10) 0.8971(18) 0.031(4) Uiso 1 1 d . . . H5 H -0.283(2) 0.1637(10) 0.7692(17) 0.030(4) Uiso 1 1 d . . . H22B H -0.283(2) -0.2487(10) 0.3603(19) 0.033(4) Uiso 1 1 d . . . H22A H -0.029(3) -0.2482(10) 0.4584(17) 0.036(4) Uiso 1 1 d . . . H11B H -0.276(2) -0.0545(11) 0.3091(18) 0.036(4) Uiso 1 1 d . . . H11A H -0.330(3) 0.0099(11) 0.182(2) 0.039(4) Uiso 1 1 d . . . H11 H -0.373(3) 0.1453(12) 0.201(3) 0.059(5) 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 O11 0.0330(5) 0.0206(4) 0.0212(4) 0.0025(3) 0.0156(4) 0.0038(3) O21 0.0284(4) 0.0167(4) 0.0244(4) 0.0006(3) 0.0173(3) 0.0015(3) N11 0.0268(5) 0.0215(5) 0.0195(5) -0.0010(4) 0.0138(4) -0.0002(4) C1 0.0150(4) 0.0209(5) 0.0176(5) -0.0017(4) 0.0088(4) -0.0011(4) C6 0.0185(5) 0.0207(5) 0.0215(5) -0.0017(4) 0.0101(4) -0.0001(4) C5 0.0219(5) 0.0270(6) 0.0219(5) -0.0068(4) 0.0122(4) -0.0007(4) C4 0.0206(5) 0.0334(6) 0.0175(5) -0.0017(4) 0.0104(4) -0.0006(4) C3 0.0212(5) 0.0248(6) 0.0215(5) 0.0027(4) 0.0119(4) 0.0009(4) C2 0.0157(5) 0.0214(5) 0.0206(5) -0.0024(4) 0.0103(4) -0.0011(4) C11 0.0146(4) 0.0203(5) 0.0200(5) -0.0008(4) 0.0093(4) -0.0009(4) C21 0.0251(5) 0.0174(5) 0.0273(6) 0.0023(4) 0.0150(5) 0.0006(4) C22 0.0302(6) 0.0211(6) 0.0308(6) -0.0027(5) 0.0165(5) 0.0001(5) Cl1 0.03860(18) 0.02136(15) 0.02249(16) -0.00030(9) 0.01933(13) -0.00021(10) _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 O11 C11 1.2978(13) . ? O11 H11 0.97(2) . ? O21 C2 1.3606(13) . ? O21 C21 1.4531(13) . ? N11 C11 1.3013(14) . ? N11 H11B 0.842(17) . ? N11 H11A 0.870(17) . ? C1 C6 1.4032(15) . ? C1 C2 1.4115(15) . ? C1 C11 1.4681(14) . ? C6 C5 1.3810(16) . ? C6 H6 0.905(15) . ? C5 C4 1.3883(17) . ? C5 H5 0.939(15) . ? C4 C3 1.3868(16) . ? C4 H4 0.987(15) . ? C3 C2 1.3920(15) . ? C3 H3 0.923(15) . ? C21 C22 1.5065(16) . ? C21 H21B 0.978(13) . ? C21 H21A 0.974(14) . ? C22 H22C 0.996(16) . ? C22 H22B 0.943(16) . ? C22 H22A 1.002(16) . ? 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 C11 O11 H11 109.8(11) . . ? C2 O21 C21 119.01(8) . . ? C11 N11 H11B 118.8(11) . . ? C11 N11 H11A 119.2(11) . . ? H11B N11 H11A 121.9(15) . . ? C6 C1 C2 119.10(10) . . ? C6 C1 C11 117.42(10) . . ? C2 C1 C11 123.44(9) . . ? C5 C6 C1 120.86(11) . . ? C5 C6 H6 120.8(9) . . ? C1 C6 H6 118.3(9) . . ? C6 C5 C4 119.39(11) . . ? C6 C5 H5 119.2(9) . . ? C4 C5 H5 121.4(9) . . ? C3 C4 C5 121.06(10) . . ? C3 C4 H4 120.1(9) . . ? C5 C4 H4 118.8(9) . . ? C4 C3 C2 119.97(11) . . ? C4 C3 H3 120.8(9) . . ? C2 C3 H3 119.2(9) . . ? O21 C2 C3 123.08(10) . . ? O21 C2 C1 117.32(9) . . ? C3 C2 C1 119.60(10) . . ? O11 C11 N11 120.40(10) . . ? O11 C11 C1 116.26(9) . . ? N11 C11 C1 123.33(10) . . ? O21 C21 C22 106.30(9) . . ? O21 C21 H21B 109.1(8) . . ? C22 C21 H21B 110.8(8) . . ? O21 C21 H21A 109.6(8) . . ? C22 C21 H21A 111.3(8) . . ? H21B C21 H21A 109.7(11) . . ? C21 C22 H22C 108.8(9) . . ? C21 C22 H22B 110.7(9) . . ? H22C C22 H22B 106.5(13) . . ? C21 C22 H22A 111.6(9) . . ? H22C C22 H22A 108.5(12) . . ? H22B C22 H22A 110.6(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 C2 C1 C6 C5 -1.49(16) . . . . ? C11 C1 C6 C5 176.05(10) . . . . ? C1 C6 C5 C4 1.30(16) . . . . ? C6 C5 C4 C3 0.15(17) . . . . ? C5 C4 C3 C2 -1.40(17) . . . . ? C21 O21 C2 C3 12.55(15) . . . . ? C21 O21 C2 C1 -168.36(9) . . . . ? C4 C3 C2 O21 -179.75(10) . . . . ? C4 C3 C2 C1 1.18(16) . . . . ? C6 C1 C2 O21 -178.88(9) . . . . ? C11 C1 C2 O21 3.73(15) . . . . ? C6 C1 C2 C3 0.24(15) . . . . ? C11 C1 C2 C3 -177.15(10) . . . . ? C6 C1 C11 O11 4.68(14) . . . . ? C2 C1 C11 O11 -177.90(10) . . . . ? C6 C1 C11 N11 -174.06(10) . . . . ? C2 C1 C11 N11 3.37(16) . . . . ? C2 O21 C21 C22 172.79(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.355 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 947738' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12007_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Ethenzamide hydrobromide salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 Br N O2' _chemical_formula_weight 246.11 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' Br Br -0.2901 2.4595 '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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6316(6) _cell_length_b 15.2521(11) _cell_length_c 10.6249(6) _cell_angle_alpha 90.00 _cell_angle_beta 124.184(4) _cell_angle_gamma 90.00 _cell_volume 1023.06(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6464 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.44 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 3.986 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.2221 _exptl_absorpt_correction_T_max 0.3359 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11566 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2330 _reflns_number_gt 2028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0233P)^2^+0.3807P] 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 2330 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0508 _refine_ls_wR_factor_gt 0.0489 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _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 -0.3425(2) 0.14018(8) -0.18504(15) 0.0325(3) Uani 1 1 d . . . O10 O -0.1779(2) -0.10508(8) 0.01378(14) 0.0283(3) Uani 1 1 d . . . N1 N -0.2952(2) -0.00147(11) -0.21875(18) 0.0277(3) Uani 1 1 d . . . C1 C -0.1581(4) -0.25308(14) -0.0433(3) 0.0377(4) Uani 1 1 d . . . C2 C -0.1597(3) -0.19397(12) 0.0686(2) 0.0307(4) Uani 1 1 d . . . C3 C -0.2048(3) 0.02419(13) 0.2935(2) 0.0319(4) Uani 1 1 d . . . C4 C -0.2564(3) 0.10581(13) 0.2247(2) 0.0305(4) Uani 1 1 d . . . C5 C -0.1771(3) -0.04727(13) 0.2265(2) 0.0295(4) Uani 1 1 d . . . C6 C -0.2803(3) 0.11598(12) 0.0872(2) 0.0269(4) Uani 1 1 d . . . C7 C -0.2039(2) -0.03778(11) 0.08612(19) 0.0237(3) Uani 1 1 d . . . C8 C -0.2570(2) 0.04470(10) 0.01473(18) 0.0222(3) Uani 1 1 d . . . C9 C -0.2982(2) 0.05988(11) -0.13576(18) 0.0231(3) Uani 1 1 d . . . Br1 Br 0.40829(3) -0.141942(11) 0.495462(19) 0.03137(7) Uani 1 1 d . . . H2B H -0.027(3) -0.1969(12) 0.171(2) 0.028(5) Uiso 1 1 d . . . H6 H -0.320(3) 0.1686(14) 0.038(2) 0.030(5) Uiso 1 1 d . . . H2A H -0.282(3) -0.2058(12) 0.074(2) 0.024(5) Uiso 1 1 d . . . H4 H -0.274(3) 0.1541(13) 0.270(2) 0.033(5) Uiso 1 1 d . . . H1C H -0.156(3) -0.3138(16) -0.018(2) 0.041(6) Uiso 1 1 d . . . H1E H -0.275(3) -0.0514(15) -0.188(2) 0.035(6) Uiso 1 1 d . . . H1B H -0.284(4) -0.2466(14) -0.143(3) 0.044(6) Uiso 1 1 d . . . H1D H -0.329(3) 0.0092(15) -0.309(3) 0.046(6) Uiso 1 1 d . . . H3 H -0.194(3) 0.0167(14) 0.387(3) 0.044(6) Uiso 1 1 d . . . H5 H -0.140(3) -0.1028(15) 0.275(2) 0.039(6) Uiso 1 1 d . . . H1A H -0.032(4) -0.2457(14) -0.044(2) 0.046(6) Uiso 1 1 d . . . H1F H -0.362(4) 0.1454(16) -0.271(3) 0.064(8) 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 O1 0.0458(8) 0.0276(7) 0.0275(7) 0.0033(5) 0.0228(6) 0.0054(6) O10 0.0364(7) 0.0218(6) 0.0316(7) 0.0017(5) 0.0222(6) 0.0024(5) N1 0.0342(8) 0.0270(8) 0.0240(8) -0.0005(6) 0.0177(7) -0.0002(6) C1 0.0418(11) 0.0264(10) 0.0441(12) -0.0027(9) 0.0237(10) 0.0005(8) C2 0.0318(9) 0.0244(9) 0.0364(10) 0.0042(7) 0.0195(9) 0.0006(7) C3 0.0270(9) 0.0482(11) 0.0202(9) -0.0009(8) 0.0130(7) -0.0004(8) C4 0.0290(9) 0.0361(10) 0.0265(9) -0.0086(8) 0.0157(8) -0.0018(8) C5 0.0271(9) 0.0350(10) 0.0267(9) 0.0048(7) 0.0153(7) 0.0021(7) C6 0.0252(8) 0.0277(9) 0.0268(9) -0.0025(7) 0.0141(7) 0.0005(7) C7 0.0200(8) 0.0270(8) 0.0252(8) -0.0023(7) 0.0135(7) -0.0009(6) C8 0.0197(7) 0.0255(8) 0.0216(8) -0.0022(6) 0.0117(6) -0.0018(6) C9 0.0194(7) 0.0257(8) 0.0238(8) -0.0014(6) 0.0120(7) -0.0017(6) Br1 0.04499(12) 0.02628(10) 0.02695(10) -0.00020(7) 0.02272(9) 0.00000(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 O1 C9 1.300(2) . ? O1 H1F 0.84(3) . ? O10 C7 1.362(2) . ? O10 C2 1.451(2) . ? N1 C9 1.295(2) . ? N1 H1E 0.81(2) . ? N1 H1D 0.86(2) . ? C1 C2 1.498(3) . ? C1 H1C 0.96(2) . ? C1 H1B 0.95(2) . ? C1 H1A 0.97(2) . ? C2 H2B 0.99(2) . ? C2 H2A 0.984(18) . ? C3 C5 1.381(3) . ? C3 C4 1.384(3) . ? C3 H3 0.95(2) . ? C4 C6 1.376(3) . ? C4 H4 0.93(2) . ? C5 C7 1.395(2) . ? C5 H5 0.95(2) . ? C6 C8 1.400(2) . ? C6 H6 0.91(2) . ? C7 C8 1.406(2) . ? C8 C9 1.464(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 C9 O1 H1F 111.9(17) . . ? C7 O10 C2 119.27(13) . . ? C9 N1 H1E 118.4(15) . . ? C9 N1 H1D 121.1(15) . . ? H1E N1 H1D 120(2) . . ? C2 C1 H1C 111.2(12) . . ? C2 C1 H1B 111.3(13) . . ? H1C C1 H1B 105.1(18) . . ? C2 C1 H1A 112.5(13) . . ? H1C C1 H1A 104.5(18) . . ? H1B C1 H1A 111.6(18) . . ? O10 C2 C1 106.56(15) . . ? O10 C2 H2B 107.1(11) . . ? C1 C2 H2B 112.9(11) . . ? O10 C2 H2A 108.4(11) . . ? C1 C2 H2A 111.7(11) . . ? H2B C2 H2A 109.9(15) . . ? C5 C3 C4 121.23(17) . . ? C5 C3 H3 119.5(13) . . ? C4 C3 H3 119.3(13) . . ? C6 C4 C3 119.37(17) . . ? C6 C4 H4 119.1(13) . . ? C3 C4 H4 121.6(13) . . ? C3 C5 C7 119.75(17) . . ? C3 C5 H5 120.8(13) . . ? C7 C5 H5 119.4(13) . . ? C4 C6 C8 120.97(17) . . ? C4 C6 H6 120.8(12) . . ? C8 C6 H6 118.1(12) . . ? O10 C7 C5 123.03(16) . . ? O10 C7 C8 117.33(14) . . ? C5 C7 C8 119.63(15) . . ? C6 C8 C7 119.04(15) . . ? C6 C8 C9 117.52(15) . . ? C7 C8 C9 123.40(14) . . ? N1 C9 O1 120.45(16) . . ? N1 C9 C8 123.66(16) . . ? O1 C9 C8 115.89(14) . . ? 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 C7 O10 C2 C1 173.66(15) . . . . ? C5 C3 C4 C6 -0.1(3) . . . . ? C4 C3 C5 C7 -0.8(3) . . . . ? C3 C4 C6 C8 1.2(3) . . . . ? C2 O10 C7 C5 11.7(2) . . . . ? C2 O10 C7 C8 -169.32(15) . . . . ? C3 C5 C7 O10 179.57(16) . . . . ? C3 C5 C7 C8 0.6(3) . . . . ? C4 C6 C8 C7 -1.4(2) . . . . ? C4 C6 C8 C9 176.18(15) . . . . ? O10 C7 C8 C6 -178.52(14) . . . . ? C5 C7 C8 C6 0.5(2) . . . . ? O10 C7 C8 C9 4.0(2) . . . . ? C5 C7 C8 C9 -176.96(15) . . . . ? C6 C8 C9 N1 -175.57(16) . . . . ? C7 C8 C9 N1 1.9(3) . . . . ? C6 C8 C9 O1 3.4(2) . . . . ? C7 C8 C9 O1 -179.08(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.287 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 947739' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11119_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Salicylamide hydrochloride salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H8 Cl N O2' _chemical_formula_weight 173.59 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0833(6) _cell_length_b 5.1811(4) _cell_length_c 16.3294(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.0110(10) _cell_angle_gamma 90.00 _cell_volume 768.37(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4421 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.31 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.442 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8789 _exptl_absorpt_correction_T_max 0.9208 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8245 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.31 _reflns_number_total 1733 _reflns_number_gt 1497 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0386P)^2^+0.2737P] 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 1733 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 0.35259(4) 0.05903(7) 0.90308(2) 0.02705(13) Uani 1 1 d . . . O2 O 0.39085(11) 0.5501(2) 1.22230(7) 0.0236(2) Uani 1 1 d . . . O11 O 0.20077(12) 0.4728(2) 0.99085(6) 0.0260(3) Uani 1 1 d . . . C5 C 0.06396(16) 1.0560(3) 1.14186(9) 0.0234(3) Uani 1 1 d . . . C4 C 0.12541(17) 1.0794(3) 1.22042(9) 0.0231(3) Uani 1 1 d . . . C11 C 0.27612(15) 0.4971(3) 1.05907(8) 0.0198(3) Uani 1 1 d . . . C1 C 0.22595(14) 0.6944(3) 1.11652(8) 0.0182(3) Uani 1 1 d . . . C2 C 0.28457(14) 0.7172(3) 1.19653(8) 0.0189(3) Uani 1 1 d . . . N11 N 0.38969(14) 0.3529(3) 1.07446(8) 0.0256(3) Uani 1 1 d . . . C3 C 0.23378(16) 0.9129(3) 1.24762(9) 0.0219(3) Uani 1 1 d . . . C6 C 0.11472(15) 0.8651(3) 1.09060(9) 0.0216(3) Uani 1 1 d . . . H3 H 0.2756(19) 0.927(3) 1.3000(11) 0.027(4) Uiso 1 1 d . . . H6 H 0.0749(18) 0.846(3) 1.0367(10) 0.026(4) Uiso 1 1 d . . . H11B H 0.433(2) 0.370(4) 1.1214(13) 0.041(5) Uiso 1 1 d . . . H4 H 0.091(2) 1.210(4) 1.2546(11) 0.038(5) Uiso 1 1 d . . . H5 H -0.013(2) 1.167(4) 1.1242(11) 0.037(5) Uiso 1 1 d . . . H11A H 0.414(2) 0.238(4) 1.0400(12) 0.042(5) Uiso 1 1 d . . . H2 H 0.388(2) 0.531(4) 1.2714(14) 0.042(6) Uiso 1 1 d . . . H11 H 0.242(2) 0.354(5) 0.9590(14) 0.056(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 Cl1 0.0324(2) 0.0302(2) 0.01855(19) -0.00548(13) -0.00069(14) 0.00422(15) O2 0.0255(5) 0.0279(6) 0.0172(5) 0.0020(4) -0.0021(4) 0.0057(4) O11 0.0338(6) 0.0264(6) 0.0178(5) -0.0039(4) -0.0046(4) 0.0039(4) C5 0.0223(7) 0.0205(7) 0.0275(8) 0.0042(6) 0.0022(6) 0.0029(6) C4 0.0252(7) 0.0191(7) 0.0253(7) -0.0031(6) 0.0060(6) -0.0009(6) C11 0.0221(7) 0.0197(6) 0.0175(6) 0.0016(5) 0.0018(5) -0.0025(5) C1 0.0200(6) 0.0168(6) 0.0178(6) 0.0010(5) 0.0018(5) -0.0015(5) C2 0.0181(6) 0.0193(7) 0.0192(7) 0.0019(5) 0.0009(5) -0.0019(5) N11 0.0254(6) 0.0283(7) 0.0231(6) -0.0065(5) -0.0013(5) 0.0059(5) C3 0.0241(7) 0.0228(7) 0.0189(7) -0.0014(5) 0.0011(5) -0.0027(6) C6 0.0229(7) 0.0226(7) 0.0192(7) 0.0026(5) -0.0010(5) -0.0006(6) _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 O2 C2 1.3581(16) . ? O2 H2 0.81(2) . ? O11 C11 1.3031(17) . ? O11 H11 0.89(2) . ? C5 C6 1.380(2) . ? C5 C4 1.395(2) . ? C5 H5 0.950(19) . ? C4 C3 1.377(2) . ? C4 H4 0.936(19) . ? C11 N11 1.2946(19) . ? C11 C1 1.4657(19) . ? C1 C6 1.4024(19) . ? C1 C2 1.4070(18) . ? C2 C3 1.3965(19) . ? N11 H11B 0.86(2) . ? N11 H11A 0.85(2) . ? C3 H3 0.933(18) . ? C6 H6 0.951(17) . ? 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 C2 O2 H2 110.5(15) . . ? C11 O11 H11 110.3(14) . . ? C6 C5 C4 119.17(13) . . ? C6 C5 H5 120.2(12) . . ? C4 C5 H5 120.6(11) . . ? C3 C4 C5 120.96(13) . . ? C3 C4 H4 120.4(12) . . ? C5 C4 H4 118.6(12) . . ? N11 C11 O11 121.00(13) . . ? N11 C11 C1 122.26(13) . . ? O11 C11 C1 116.73(12) . . ? C6 C1 C2 119.09(13) . . ? C6 C1 C11 118.49(12) . . ? C2 C1 C11 122.41(12) . . ? O2 C2 C3 121.22(12) . . ? O2 C2 C1 119.31(12) . . ? C3 C2 C1 119.47(13) . . ? C11 N11 H11B 117.8(14) . . ? C11 N11 H11A 119.4(13) . . ? H11B N11 H11A 122.6(19) . . ? C4 C3 C2 120.27(13) . . ? C4 C3 H3 121.7(11) . . ? C2 C3 H3 118.0(11) . . ? C5 C6 C1 121.02(13) . . ? C5 C6 H6 120.6(11) . . ? C1 C6 H6 118.4(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.31 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.323 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 947740' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_test3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Ethenzamide HNO3 salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H57 N15 O37' _chemical_formula_weight 1508.15 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 Hexagonal _symmetry_space_group_name_H-M R3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' _cell_length_a 38.522(5) _cell_length_b 38.522(5) _cell_length_c 3.9027(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5015.6(12) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needles _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2346 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.9809 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19178 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_h_max 49 _diffrn_reflns_limit_k_min -49 _diffrn_reflns_limit_k_max 49 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.39 _reflns_number_total 4982 _reflns_number_gt 3734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _refine_ls_number_reflns 4982 _refine_ls_number_parameters 367 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.2149 _refine_ls_wR_factor_gt 0.2001 _refine_ls_goodness_of_fit_ref 1.517 _refine_ls_restrained_S_all 1.520 _refine_ls_shift/su_max 0.285 _refine_ls_shift/su_mean 0.053 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 O35 O 0.64095(11) 0.09688(12) 0.4825(10) 0.0384(9) Uani 1 1 d . . . O34 O 0.55719(12) 0.11159(11) -0.0687(11) 0.0420(9) Uani 1 1 d . . . N33 N 0.56960(14) 0.06588(14) 0.1835(13) 0.0391(11) Uani 1 1 d . . . C32 C 0.64954(15) 0.13364(16) 0.3860(13) 0.0321(11) Uani 1 1 d . . . C31 C 0.61984(15) 0.13765(16) 0.2044(12) 0.0323(11) Uani 1 1 d . . . C30 C 0.62725(18) 0.17492(17) 0.1078(15) 0.0386(13) Uani 1 1 d . A . H30A H 0.6073 0.1774 -0.0150 0.046 Uiso 1 1 calc R . . C29 C 0.58040(16) 0.10349(15) 0.1046(13) 0.0323(11) Uani 1 1 d . . . C27 C 0.68503(16) 0.16721(19) 0.4549(13) 0.0375(13) Uani 1 1 d . . . H27A H 0.7055 0.1650 0.5714 0.045 Uiso 1 1 calc R . . C26 C 0.69171(18) 0.2053(2) 0.3547(17) 0.0501(17) Uani 1 1 d . A . H26A H 0.7165 0.2286 0.4065 0.060 Uiso 1 1 calc R . . C25 C 0.66286(18) 0.20872(19) 0.1848(17) 0.0442(14) Uani 1 1 d . . . C23 C 0.67142(15) 0.09197(16) 0.6477(14) 0.0366(12) Uani 1 1 d . . . H23A H 0.6797 0.1078 0.8624 0.044 Uiso 1 1 calc R . . H23B H 0.6951 0.1021 0.4963 0.044 Uiso 1 1 calc R . . C22 C 0.6562(2) 0.0490(2) 0.7266(18) 0.0499(15) Uani 1 1 d . . . H22A H 0.6775 0.0461 0.8363 0.075 Uiso 1 1 calc R . . H22B H 0.6480 0.0334 0.5138 0.075 Uiso 1 1 calc R . . H22C H 0.6332 0.0392 0.8817 0.075 Uiso 1 1 calc R . . O16 O 0.35907(11) -0.09644(12) -0.2965(9) 0.0367(9) Uani 1 1 d . . . O15 O 0.44299(12) -0.11114(12) 0.2482(11) 0.0443(9) Uani 1 1 d . . . N14 N 0.43114(14) -0.06691(14) -0.0108(13) 0.0390(11) Uani 1 1 d . . . C13 C 0.42062(14) -0.10278(16) 0.0764(14) 0.0311(11) Uani 1 1 d . . . C12 C 0.35117(17) -0.13406(18) -0.2021(12) 0.0352(12) Uani 1 1 d . . . C11 C 0.38129(16) -0.13682(16) -0.0236(12) 0.0321(11) Uani 1 1 d . . . C10 C 0.37348(16) -0.17552(15) 0.0734(14) 0.0335(12) Uani 1 1 d . A . H10A H 0.3934 -0.1783 0.1928 0.040 Uiso 1 1 calc R . . C9 C 0.31372(17) -0.16927(18) -0.2755(14) 0.0418(14) Uani 1 1 d . . . H9A H 0.2933 -0.1671 -0.3930 0.050 Uiso 1 1 calc R . . C8 C 0.3464(2) -0.0486(2) -0.5549(16) 0.0462(14) Uani 1 1 d . . . H8A H 0.3270 -0.0436 -0.6759 0.069 Uiso 1 1 calc R . . H8B H 0.3699 -0.0405 -0.7006 0.069 Uiso 1 1 calc R . . H8C H 0.3546 -0.0330 -0.3421 0.069 Uiso 1 1 calc R . . C7 C 0.30755(16) -0.20531(17) -0.1782(15) 0.0412(14) Uani 1 1 d . A . H7A H 0.2826 -0.2286 -0.2287 0.049 Uiso 1 1 calc R . . C6 C 0.33724(19) -0.20938(18) -0.0027(17) 0.0441(14) Uani 1 1 d . . . C5 C 0.32751(18) -0.0923(2) -0.4724(15) 0.0475(16) Uani 1 1 d . . . H5A H 0.3039 -0.1009 -0.3215 0.057 Uiso 1 1 calc R . . H5B H 0.3189 -0.1086 -0.6843 0.057 Uiso 1 1 calc R . . N18 N 0.6675(3) 0.2435(3) 0.094(3) 0.0797(17) Uani 0.637(9) 1 d P A 1 O17 O 0.6985(3) 0.2734(3) 0.138(4) 0.126(3) Uani 0.637(9) 1 d P A 1 O19 O 0.6389(3) 0.2444(3) -0.051(4) 0.122(3) Uani 0.637(9) 1 d P A 1 N18' N 0.3292(5) -0.2479(6) 0.104(6) 0.0797(17) Uani 0.363(9) 1 d P A 2 O17' O 0.2954(6) -0.2781(6) 0.030(8) 0.126(3) Uani 0.363(9) 1 d P A 2 O19' O 0.3546(6) -0.2521(6) 0.293(7) 0.122(3) Uani 0.363(9) 1 d P A 2 O100 O 0.6667 0.3333 -0.24(3) 0.60(7) Uani 1 3 d S . . N28 N 0.5287(8) -0.0302(13) 0.438(6) 0.040(2) Uani 0.624(6) 1 d PDU B 1 O21 O 0.50691(19) -0.0171(2) 0.363(2) 0.0498(15) Uani 0.624(6) 1 d PDU B 1 O20 O 0.5065(4) -0.0694(5) 0.518(3) 0.069(4) Uani 0.624(6) 1 d PDU B 1 O24 O 0.56502(19) -0.0117(2) 0.455(2) 0.0474(15) Uani 0.624(6) 1 d PDU B 1 N28' N 0.5293(13) -0.033(2) 0.378(11) 0.040(2) Uani 0.376(6) 1 d PDU B 2 O21' O 0.5177(3) -0.0247(3) 0.152(4) 0.0498(15) Uani 0.376(6) 1 d PDU B 2 O20' O 0.5131(8) -0.0681(8) 0.390(6) 0.069(4) Uani 0.376(6) 1 d PDU B 2 O24' O 0.5558(3) -0.0099(4) 0.609(3) 0.0474(15) Uani 0.376(6) 1 d PDU B 2 N4 N 0.4734(10) 0.0307(13) -0.281(7) 0.027(2) Uani 0.434(4) 1 d PDU C 1 O3 O 0.4360(8) 0.0140(8) -0.265(7) 0.061(4) Uani 0.434(4) 1 d PDU C 1 O2 O 0.4971(2) 0.0636(2) -0.407(2) 0.0334(10) Uani 0.434(4) 1 d PDU C 1 O1 O 0.4928(3) 0.0163(3) -0.213(2) 0.0459(14) Uani 0.434(4) 1 d PDU C 1 N4' N 0.4701(7) 0.0325(9) -0.212(5) 0.027(2) Uani 0.566(4) 1 d PDU C 2 O3' O 0.4377(6) 0.0084(6) -0.377(4) 0.061(4) Uani 0.566(4) 1 d PDU C 2 O2' O 0.48846(18) 0.07094(18) -0.2383(16) 0.0334(10) Uani 0.566(4) 1 d PDU C 2 O1' O 0.4810(2) 0.02208(19) 0.0218(18) 0.0459(14) Uani 0.566(4) 1 d PDU C 2 H14A H 0.404(2) -0.069(2) -0.04(2) 0.11(3) Uiso 1 1 d . . . H33B H 0.5847(9) 0.0591(9) 0.332(8) 0.005(7) Uiso 1 1 d . . . H33A H 0.5440(9) 0.0444(9) 0.123(7) 0.005(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 O35 0.0304(19) 0.045(2) 0.041(2) -0.0028(17) -0.0040(16) 0.0192(17) O34 0.034(2) 0.035(2) 0.058(3) 0.0050(18) -0.0074(18) 0.0169(17) N33 0.032(2) 0.036(2) 0.046(3) 0.001(2) -0.001(2) 0.014(2) C32 0.022(2) 0.040(3) 0.034(3) -0.003(2) 0.006(2) 0.015(2) C31 0.028(2) 0.039(3) 0.027(3) -0.006(2) 0.005(2) 0.014(2) C30 0.040(3) 0.037(3) 0.041(3) -0.003(2) 0.001(2) 0.021(2) C29 0.038(3) 0.033(2) 0.026(3) -0.001(2) 0.003(2) 0.018(2) C27 0.029(2) 0.059(4) 0.028(3) -0.003(2) 0.002(2) 0.024(3) C26 0.036(3) 0.052(4) 0.047(4) -0.016(3) 0.006(3) 0.010(3) C25 0.039(3) 0.044(3) 0.046(3) 0.002(3) 0.018(3) 0.018(3) C23 0.031(2) 0.043(3) 0.036(3) -0.001(2) -0.001(2) 0.019(2) C22 0.050(3) 0.065(4) 0.045(3) 0.002(3) 0.000(3) 0.037(3) O16 0.038(2) 0.046(2) 0.032(2) 0.0058(16) 0.0003(16) 0.0245(18) O15 0.039(2) 0.041(2) 0.049(2) 0.0031(19) -0.0045(19) 0.0166(18) N14 0.037(2) 0.037(3) 0.047(3) 0.001(2) -0.006(2) 0.021(2) C13 0.021(2) 0.042(3) 0.033(3) 0.001(2) 0.0039(19) 0.018(2) C12 0.041(3) 0.048(3) 0.019(2) -0.003(2) 0.005(2) 0.023(2) C11 0.034(3) 0.040(3) 0.025(3) 0.001(2) 0.007(2) 0.021(2) C10 0.030(2) 0.036(3) 0.034(3) 0.001(2) 0.012(2) 0.016(2) C9 0.036(3) 0.042(3) 0.036(3) -0.014(2) 0.000(2) 0.011(2) C8 0.058(3) 0.063(4) 0.032(3) 0.001(3) -0.010(3) 0.042(3) C7 0.030(3) 0.043(3) 0.039(3) -0.011(3) 0.005(2) 0.009(2) C6 0.047(3) 0.035(3) 0.047(4) -0.012(2) 0.001(3) 0.018(3) C5 0.046(3) 0.089(5) 0.025(3) -0.002(3) -0.004(2) 0.047(3) N18 0.048(3) 0.058(3) 0.119(5) -0.007(3) 0.003(3) 0.016(3) O17 0.075(4) 0.060(4) 0.220(8) -0.003(4) 0.002(4) 0.016(3) O19 0.075(4) 0.072(5) 0.214(9) 0.012(5) -0.027(5) 0.034(4) N18' 0.048(3) 0.058(3) 0.119(5) -0.007(3) 0.003(3) 0.016(3) O17' 0.075(4) 0.060(4) 0.220(8) -0.003(4) 0.002(4) 0.016(3) O19' 0.075(4) 0.072(5) 0.214(9) 0.012(5) -0.027(5) 0.034(4) O100 0.32(2) 0.32(2) 1.2(2) 0.000 0.000 0.161(11) N28 0.036(3) 0.039(5) 0.046(8) 0.005(7) -0.008(4) 0.020(2) O21 0.043(3) 0.045(3) 0.074(4) 0.007(2) -0.007(3) 0.031(2) O20 0.053(6) 0.038(2) 0.097(11) 0.035(6) -0.025(6) 0.008(3) O24 0.024(3) 0.052(3) 0.063(4) 0.013(3) -0.005(2) 0.016(2) N28' 0.036(3) 0.039(5) 0.046(8) 0.005(7) -0.008(4) 0.020(2) O21' 0.043(3) 0.045(3) 0.074(4) 0.007(2) -0.007(3) 0.031(2) O20' 0.053(6) 0.038(2) 0.097(11) 0.035(6) -0.025(6) 0.008(3) O24' 0.024(3) 0.052(3) 0.063(4) 0.013(3) -0.005(2) 0.016(2) N4 0.030(4) 0.032(4) 0.024(8) -0.002(5) 0.005(5) 0.019(3) O3 0.038(3) 0.039(5) 0.086(12) -0.004(5) -0.026(6) 0.005(3) O2 0.031(2) 0.033(2) 0.037(3) -0.0017(19) -0.0052(19) 0.0158(18) O1 0.049(3) 0.031(2) 0.034(2) 0.009(2) -0.010(2) 0.002(2) N4' 0.030(4) 0.032(4) 0.024(8) -0.002(5) 0.005(5) 0.019(3) O3' 0.038(3) 0.039(5) 0.086(12) -0.004(5) -0.026(6) 0.005(3) O2' 0.031(2) 0.033(2) 0.037(3) -0.0017(19) -0.0052(19) 0.0158(18) O1' 0.049(3) 0.031(2) 0.034(2) 0.009(2) -0.010(2) 0.002(2) _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 O35 C32 1.337(7) . ? O35 C23 1.432(6) . ? O34 C29 1.278(7) . ? N33 C29 1.328(7) . ? N33 H33B 0.95(3) . ? N33 H33A 0.95(3) . ? C32 C27 1.358(8) . ? C32 C31 1.418(7) . ? C31 C30 1.369(8) . ? C31 C29 1.481(8) . ? C30 C25 1.372(9) . ? C30 H30A 0.9500 . ? C27 C26 1.412(9) . ? C27 H27A 0.9500 . ? C26 C25 1.356(10) . ? C26 H26A 0.9500 . ? C25 N18 1.308(13) . ? C23 C22 1.486(9) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? O16 C12 1.374(7) . ? O16 C5 1.473(7) . ? O15 C13 1.254(6) . ? N14 C13 1.276(7) . ? N14 H14A 1.03(8) . ? C13 C11 1.477(8) . ? C12 C11 1.402(8) . ? C12 C9 1.431(8) . ? C11 C10 1.417(7) . ? C10 C6 1.385(8) . ? C10 H10A 0.9500 . ? C9 C7 1.341(9) . ? C9 H9A 0.9500 . ? C8 C5 1.498(9) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C7 C6 1.408(9) . ? C7 H7A 0.9500 . ? C6 N18' 1.42(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N18 O17 1.186(14) . ? N18 O19 1.256(15) . ? N18' O17' 1.27(3) . ? N18' O19' 1.30(3) . ? N28 O21 1.21(4) . ? N28 O24 1.21(3) . ? N28 O20 1.35(5) . ? N28' O21' 1.10(6) . ? N28' O20' 1.19(8) . ? N28' O24' 1.31(5) . ? N4 O1 1.16(4) . ? N4 O2 1.23(4) . ? N4 O3 1.25(5) . ? N4' O1' 1.16(3) . ? N4' O2' 1.29(3) . ? N4' O3' 1.30(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 C32 O35 C23 118.8(4) . . ? C29 N33 H33B 123.0(18) . . ? C29 N33 H33A 121.1(18) . . ? H33B N33 H33A 115(3) . . ? O35 C32 C27 123.4(5) . . ? O35 C32 C31 118.0(5) . . ? C27 C32 C31 118.5(5) . . ? C30 C31 C32 119.7(5) . . ? C30 C31 C29 116.3(5) . . ? C32 C31 C29 124.1(5) . . ? C31 C30 C25 121.4(6) . . ? C31 C30 H30A 119.3 . . ? C25 C30 H30A 119.3 . . ? O34 C29 N33 120.9(5) . . ? O34 C29 C31 117.1(4) . . ? N33 C29 C31 122.0(5) . . ? C32 C27 C26 120.5(5) . . ? C32 C27 H27A 119.7 . . ? C26 C27 H27A 119.7 . . ? C25 C26 C27 120.3(6) . . ? C25 C26 H26A 119.8 . . ? C27 C26 H26A 119.9 . . ? N18 C25 C26 122.2(7) . . ? N18 C25 C30 118.2(8) . . ? C26 C25 C30 119.6(6) . . ? O35 C23 C22 110.4(4) . . ? O35 C23 H23A 109.6 . . ? C22 C23 H23A 109.6 . . ? O35 C23 H23B 109.6 . . ? C22 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C12 O16 C5 118.7(5) . . ? C13 N14 H14A 102(4) . . ? O15 C13 N14 122.2(5) . . ? O15 C13 C11 116.4(5) . . ? N14 C13 C11 121.4(5) . . ? O16 C12 C11 117.3(5) . . ? O16 C12 C9 122.2(5) . . ? C11 C12 C9 120.5(5) . . ? C12 C11 C10 117.6(5) . . ? C12 C11 C13 125.8(5) . . ? C10 C11 C13 116.6(5) . . ? C6 C10 C11 121.2(6) . . ? C6 C10 H10A 119.4 . . ? C11 C10 H10A 119.4 . . ? C7 C9 C12 119.8(6) . . ? C7 C9 H9A 120.1 . . ? C12 C9 H9A 120.1 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.4 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 C7 C6 121.3(5) . . ? C9 C7 H7A 119.3 . . ? C6 C7 H7A 119.4 . . ? C10 C6 C7 119.5(6) . . ? C10 C6 N18' 120.9(10) . . ? C7 C6 N18' 119.6(9) . . ? O16 C5 C8 105.0(5) . . ? O16 C5 H5A 110.7 . . ? C8 C5 H5A 110.7 . . ? O16 C5 H5B 110.8 . . ? C8 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? O17 N18 O19 120.5(14) . . ? O17 N18 C25 120.8(13) . . ? O19 N18 C25 118.6(10) . . ? O17' N18' O19' 120(2) . . ? O17' N18' C6 119(2) . . ? O19' N18' C6 120.9(17) . . ? O21 N28 O24 127(4) . . ? O21 N28 O20 110(2) . . ? O24 N28 O20 123(3) . . ? O21' N28' O20' 107(4) . . ? O21' N28' O24' 131(7) . . ? O20' N28' O24' 122(6) . . ? O1 N4 O2 105(3) . . ? O1 N4 O3 126(4) . . ? O2 N4 O3 128(4) . . ? O1' N4' O2' 112.2(19) . . ? O1' N4' O3' 122(3) . . ? O2' N4' O3' 124(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.588 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 947741' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12009z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Ethenzamide HClO4 salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 Cl N O6' _chemical_formula_weight 265.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.7925(17) _cell_length_b 14.670(4) _cell_length_c 11.674(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.785(3) _cell_angle_gamma 90.00 _cell_volume 1157.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7207 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.84 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.8882 _exptl_absorpt_correction_T_max 0.9183 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2594 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.38 _reflns_number_total 2594 _reflns_number_gt 2334 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0421P)^2^+0.4111P] 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 2594 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Cl1 Cl 0.26405(8) 0.62584(3) 0.44440(4) 0.03138(13) Uani 1 1 d . . . O14 O 0.2186(2) 0.36642(8) 0.89128(11) 0.0273(3) Uani 1 1 d . . . O16 O 0.3030(3) 0.62461(10) 0.76420(12) 0.0412(4) Uani 1 1 d . . . C13 C 0.2352(3) 0.43014(14) 1.08350(16) 0.0283(4) Uani 1 1 d . . . C12 C 0.2581(3) 0.52585(12) 0.91651(15) 0.0235(4) Uani 1 1 d . . . C11 C 0.2550(3) 0.50631(14) 1.15347(16) 0.0305(4) Uani 1 1 d . . . C10 C 0.2599(3) 0.54147(12) 0.79299(16) 0.0260(4) Uani 1 1 d . . . O9 O 0.2847(3) 0.67701(9) 0.55244(12) 0.0432(4) Uani 1 1 d . . . C8 C 0.2358(3) 0.43866(12) 0.96471(15) 0.0235(4) Uani 1 1 d . . . N15 N 0.2210(3) 0.47969(12) 0.71503(15) 0.0359(4) Uani 1 1 d . . . C7 C 0.2764(3) 0.59277(14) 1.10739(17) 0.0297(4) Uani 1 1 d . . . O6 O 0.0990(3) 0.66054(12) 0.37297(15) 0.0520(5) Uani 1 1 d . . . O5 O 0.2337(3) 0.53164(10) 0.46992(13) 0.0539(5) Uani 1 1 d . . . C4 C 0.2098(3) 0.27527(13) 0.93938(18) 0.0330(4) Uani 1 1 d . . . C3 C 0.2776(3) 0.60198(13) 0.99000(17) 0.0273(4) Uani 1 1 d . . . O2 O 0.4388(3) 0.63750(14) 0.38857(17) 0.0593(5) Uani 1 1 d . . . C1 C 0.2041(4) 0.21012(15) 0.8397(2) 0.0434(6) Uani 1 1 d . . . H3 H 0.293(3) 0.6587(16) 0.9573(19) 0.031(6) Uiso 1 1 d . . . H4B H 0.331(4) 0.2654(16) 0.997(2) 0.044(7) Uiso 1 1 d . . . H11 H 0.255(4) 0.4951(14) 1.2339(19) 0.029(5) Uiso 1 1 d . . . H1C H 0.319(5) 0.2179(18) 0.795(2) 0.049(7) Uiso 1 1 d . . . H7 H 0.291(3) 0.6437(15) 1.1537(19) 0.029(6) Uiso 1 1 d . . . H13 H 0.222(4) 0.3742(16) 1.115(2) 0.037(6) Uiso 1 1 d . . . H15B H 0.195(4) 0.425(2) 0.735(2) 0.048(7) Uiso 1 1 d . . . H4A H 0.101(4) 0.2689(15) 0.981(2) 0.034(6) Uiso 1 1 d . . . H1B H 0.089(5) 0.2218(18) 0.788(3) 0.053(8) Uiso 1 1 d . . . H16 H 0.296(4) 0.6335(18) 0.694(2) 0.049(7) Uiso 1 1 d . . . H1A H 0.216(5) 0.147(2) 0.872(3) 0.066(9) Uiso 1 1 d . . . H151 H 0.224(4) 0.4908(17) 0.641(2) 0.046(7) 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 Cl1 0.0449(3) 0.0253(2) 0.0233(2) -0.00090(17) 0.00024(19) -0.0013(2) O14 0.0362(7) 0.0193(6) 0.0263(6) -0.0023(5) 0.0036(5) -0.0003(6) O16 0.0706(12) 0.0271(7) 0.0249(7) 0.0027(6) -0.0002(7) -0.0074(8) C13 0.0284(9) 0.0283(9) 0.0284(9) 0.0015(7) 0.0046(7) 0.0000(8) C12 0.0205(8) 0.0240(8) 0.0255(8) -0.0010(6) 0.0000(7) 0.0019(7) C11 0.0291(10) 0.0387(10) 0.0239(9) -0.0034(8) 0.0040(7) 0.0008(8) C10 0.0253(9) 0.0239(9) 0.0281(9) 0.0009(7) -0.0006(7) 0.0017(7) O9 0.0778(12) 0.0270(7) 0.0238(7) -0.0019(5) 0.0001(8) -0.0030(7) C8 0.0204(9) 0.0235(8) 0.0262(9) -0.0026(7) 0.0010(7) 0.0018(7) N15 0.0573(13) 0.0282(9) 0.0219(8) -0.0007(6) 0.0031(8) -0.0045(8) C7 0.0283(10) 0.0315(10) 0.0291(9) -0.0082(8) 0.0016(8) 0.0004(8) O6 0.0607(12) 0.0478(9) 0.0436(9) -0.0013(8) -0.0140(8) 0.0083(9) O5 0.1021(15) 0.0225(7) 0.0364(8) -0.0006(6) 0.0043(9) -0.0069(9) C4 0.0408(12) 0.0221(9) 0.0356(10) 0.0011(8) 0.0023(10) 0.0004(8) C3 0.0264(9) 0.0238(9) 0.0313(9) -0.0025(7) 0.0004(7) 0.0005(7) O2 0.0551(12) 0.0765(14) 0.0488(10) -0.0098(10) 0.0173(9) -0.0121(10) C1 0.0583(16) 0.0245(10) 0.0455(13) -0.0053(9) -0.0037(12) 0.0047(10) _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 Cl1 O2 1.421(2) . ? Cl1 O6 1.4225(18) . ? Cl1 O5 1.4329(16) . ? Cl1 O9 1.4624(14) . ? O14 C8 1.361(2) . ? O14 C4 1.454(2) . ? O16 C10 1.306(2) . ? O16 H16 0.83(3) . ? C13 C11 1.383(3) . ? C13 C8 1.393(3) . ? C13 H13 0.91(2) . ? C12 C3 1.406(2) . ? C12 C8 1.412(3) . ? C12 C10 1.461(2) . ? C11 C7 1.391(3) . ? C11 H11 0.95(2) . ? C10 N15 1.293(2) . ? N15 H15B 0.86(3) . ? N15 H151 0.88(3) . ? C7 C3 1.378(3) . ? C7 H7 0.92(2) . ? C4 C1 1.503(3) . ? C4 H4B 1.02(3) . ? C4 H4A 0.93(3) . ? C3 H3 0.93(2) . ? C1 H1C 0.98(3) . ? C1 H1B 0.95(3) . ? C1 H1A 0.99(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 O2 Cl1 O6 109.49(12) . . ? O2 Cl1 O5 110.85(13) . . ? O6 Cl1 O5 110.21(12) . . ? O2 Cl1 O9 108.77(11) . . ? O6 Cl1 O9 108.87(10) . . ? O5 Cl1 O9 108.60(9) . . ? C8 O14 C4 118.51(14) . . ? C10 O16 H16 114.2(18) . . ? C11 C13 C8 120.38(18) . . ? C11 C13 H13 119.8(15) . . ? C8 C13 H13 119.8(15) . . ? C3 C12 C8 118.92(16) . . ? C3 C12 C10 117.89(16) . . ? C8 C12 C10 123.18(16) . . ? C13 C11 C7 121.07(17) . . ? C13 C11 H11 115.7(13) . . ? C7 C11 H11 123.2(13) . . ? N15 C10 O16 120.58(18) . . ? N15 C10 C12 124.28(17) . . ? O16 C10 C12 115.14(16) . . ? O14 C8 C13 123.27(17) . . ? O14 C8 C12 117.41(15) . . ? C13 C8 C12 119.31(16) . . ? C10 N15 H15B 119.5(18) . . ? C10 N15 H151 122.4(17) . . ? H15B N15 H151 118(2) . . ? C3 C7 C11 119.03(17) . . ? C3 C7 H7 119.5(13) . . ? C11 C7 H7 121.5(13) . . ? O14 C4 C1 106.54(17) . . ? O14 C4 H4B 108.9(14) . . ? C1 C4 H4B 112.2(14) . . ? O14 C4 H4A 111.1(14) . . ? C1 C4 H4A 112.3(14) . . ? H4B C4 H4A 105.9(19) . . ? C7 C3 C12 121.29(17) . . ? C7 C3 H3 120.7(14) . . ? C12 C3 H3 118.0(14) . . ? C4 C1 H1C 112.0(16) . . ? C4 C1 H1B 109.5(17) . . ? H1C C1 H1B 106(2) . . ? C4 C1 H1A 107.4(17) . . ? H1C C1 H1A 106(2) . . ? H1B C1 H1A 116(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 C8 C13 C11 C7 -0.2(3) . . . . ? C3 C12 C10 N15 -171.7(2) . . . . ? C8 C12 C10 N15 7.6(3) . . . . ? C3 C12 C10 O16 7.7(3) . . . . ? C8 C12 C10 O16 -172.97(18) . . . . ? C4 O14 C8 C13 -3.4(3) . . . . ? C4 O14 C8 C12 175.64(16) . . . . ? C11 C13 C8 O14 179.47(18) . . . . ? C11 C13 C8 C12 0.4(3) . . . . ? C3 C12 C8 O14 -179.59(16) . . . . ? C10 C12 C8 O14 1.1(3) . . . . ? C3 C12 C8 C13 -0.5(3) . . . . ? C10 C12 C8 C13 -179.83(18) . . . . ? C13 C11 C7 C3 0.1(3) . . . . ? C8 O14 C4 C1 -176.52(18) . . . . ? C11 C7 C3 C12 -0.2(3) . . . . ? C8 C12 C3 C7 0.4(3) . . . . ? C10 C12 C3 C7 179.75(19) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.263 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 947742' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12013_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'SalicylamidE HNO3 salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H8 N2 O5' _chemical_formula_weight 200.15 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2073(7) _cell_length_b 5.0535(3) _cell_length_c 16.9090(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.7910(10) _cell_angle_gamma 90.00 _cell_volume 843.31(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5239 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.29 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9551 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8523 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.30 _reflns_number_total 1901 _reflns_number_gt 1662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0468P)^2^+0.2091P] 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 1901 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 O14 O 0.07178(9) 0.08918(17) 0.41741(5) 0.0312(2) Uani 1 1 d . . . O13 O 0.29838(9) -0.46304(18) 0.46117(5) 0.0305(2) Uani 1 1 d . . . N12 N 0.14151(10) -0.3340(2) 0.52606(6) 0.0256(2) Uani 1 1 d . . . O11 O 0.12741(9) -0.60891(18) 0.65397(5) 0.0315(2) Uani 1 1 d . . . N10 N 0.11443(10) 0.07010(19) 0.35467(6) 0.0250(2) Uani 1 1 d . . . C9 C 0.29240(11) -0.6977(2) 0.58081(7) 0.0245(2) Uani 1 1 d . . . O8 O 0.07077(10) 0.22101(19) 0.29639(5) 0.0377(2) Uani 1 1 d . . . O7 O 0.20224(9) -0.10127(19) 0.35089(5) 0.0353(2) Uani 1 1 d . . . C6 C 0.23991(11) -0.4883(2) 0.52124(7) 0.0237(2) Uani 1 1 d . . . C5 C 0.23355(11) -0.7554(2) 0.64554(7) 0.0254(3) Uani 1 1 d . . . C4 C 0.39402(13) -1.1070(3) 0.68888(8) 0.0335(3) Uani 1 1 d . . . C3 C 0.28446(13) -0.9637(3) 0.69840(7) 0.0308(3) Uani 1 1 d . . . C2 C 0.40455(12) -0.8454(3) 0.57284(8) 0.0292(3) Uani 1 1 d . . . C1 C 0.45566(13) -1.0477(3) 0.62653(8) 0.0332(3) Uani 1 1 d . . . H3 H 0.2418(15) -1.005(3) 0.7400(9) 0.036(4) Uiso 1 1 d . . . H2 H 0.4448(14) -0.804(3) 0.5302(8) 0.031(4) Uiso 1 1 d . . . H12B H 0.1032(15) -0.351(3) 0.5668(9) 0.035(4) Uiso 1 1 d . . . H12A H 0.1136(15) -0.202(3) 0.4887(10) 0.037(4) Uiso 1 1 d . . . H1 H 0.5330(16) -1.144(3) 0.6215(9) 0.040(4) Uiso 1 1 d . . . H4 H 0.4283(14) -1.251(3) 0.7255(9) 0.035(4) Uiso 1 1 d . . . H11 H 0.1112(18) -0.636(4) 0.7022(11) 0.050(5) Uiso 1 1 d . . . H13 H 0.261(2) -0.326(4) 0.4251(12) 0.064(5) 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 O14 0.0400(5) 0.0316(5) 0.0270(4) 0.0008(3) 0.0178(4) 0.0041(4) O13 0.0340(5) 0.0325(5) 0.0297(4) 0.0038(4) 0.0170(4) 0.0034(4) N12 0.0291(5) 0.0264(5) 0.0235(5) 0.0015(4) 0.0107(4) 0.0014(4) O11 0.0386(5) 0.0336(5) 0.0274(4) 0.0024(3) 0.0177(4) 0.0046(4) N10 0.0286(5) 0.0249(5) 0.0230(5) -0.0030(4) 0.0094(4) -0.0025(4) C9 0.0260(5) 0.0225(6) 0.0246(5) -0.0026(4) 0.0057(4) -0.0024(4) O8 0.0535(6) 0.0366(5) 0.0263(4) 0.0065(4) 0.0164(4) 0.0127(4) O7 0.0392(5) 0.0394(5) 0.0320(5) 0.0047(4) 0.0177(4) 0.0124(4) C6 0.0255(5) 0.0240(6) 0.0225(5) -0.0037(4) 0.0079(4) -0.0040(4) C5 0.0279(6) 0.0252(6) 0.0229(5) -0.0043(4) 0.0060(4) -0.0032(4) C4 0.0364(7) 0.0270(6) 0.0309(6) 0.0013(5) -0.0032(5) -0.0001(5) C3 0.0378(7) 0.0294(6) 0.0238(6) 0.0001(5) 0.0051(5) -0.0049(5) C2 0.0275(6) 0.0300(6) 0.0306(6) -0.0034(5) 0.0083(5) -0.0016(5) C1 0.0278(6) 0.0307(7) 0.0384(7) -0.0039(5) 0.0033(5) 0.0031(5) _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 O14 N10 1.2490(12) . ? O13 C6 1.3090(13) . ? N12 C6 1.2904(15) . ? O11 C5 1.3494(14) . ? N10 O8 1.2358(13) . ? N10 O7 1.2597(13) . ? C9 C2 1.4019(16) . ? C9 C5 1.4069(16) . ? C9 C6 1.4648(16) . ? C5 C3 1.3929(17) . ? C4 C3 1.3756(19) . ? C4 C1 1.3915(19) . ? C2 C1 1.3779(18) . ? 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 O8 N10 O14 119.79(10) . . ? O8 N10 O7 120.01(9) . . ? O14 N10 O7 120.20(9) . . ? C2 C9 C5 119.05(11) . . ? C2 C9 C6 118.88(10) . . ? C5 C9 C6 122.07(10) . . ? N12 C6 O13 120.43(11) . . ? N12 C6 C9 123.15(10) . . ? O13 C6 C9 116.41(10) . . ? O11 C5 C3 121.67(11) . . ? O11 C5 C9 118.82(11) . . ? C3 C5 C9 119.50(11) . . ? C3 C4 C1 120.91(12) . . ? C4 C3 C5 120.26(12) . . ? C1 C2 C9 120.85(12) . . ? C2 C1 C4 119.38(12) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.276 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 947743' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12027_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Salicylamide HClO4 salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H8 Cl N O6' _chemical_formula_weight 237.59 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' Cl Cl 0.1484 0.1585 '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 18.6631(17) _cell_length_b 5.1858(5) _cell_length_c 20.1660(18) _cell_angle_alpha 90.00 _cell_angle_beta 106.8520(10) _cell_angle_gamma 90.00 _cell_volume 1867.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3231 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.44 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.419 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8846 _exptl_absorpt_correction_T_max 0.9284 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8748 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2123 _reflns_number_gt 1715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0407P)^2^+1.8027P] 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 2123 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 0.12975(2) 0.42906(8) 0.42066(2) 0.02411(14) Uani 1 1 d . . . O13 O -0.00244(8) 0.9579(3) 0.32993(7) 0.0292(3) Uani 1 1 d . . . O12 O -0.14934(9) 1.0605(3) 0.44672(8) 0.0340(4) Uani 1 1 d . . . O11 O 0.07559(7) 0.4163(3) 0.45952(7) 0.0315(3) Uani 1 1 d . . . C10 C -0.04432(10) 0.9762(3) 0.37150(9) 0.0210(4) Uani 1 1 d . . . C9 C -0.20694(11) 1.5701(4) 0.31796(10) 0.0279(4) Uani 1 1 d . . . O8 O 0.09515(9) 0.5659(3) 0.35674(7) 0.0385(4) Uani 1 1 d . . . O7 O 0.19425(8) 0.5684(3) 0.45994(8) 0.0375(4) Uani 1 1 d . . . C6 C -0.15713(11) 1.5336(4) 0.27953(10) 0.0266(4) Uani 1 1 d . . . N12 N -0.03465(9) 0.8252(3) 0.42437(8) 0.0243(3) Uani 1 1 d . . . C5 C -0.15268(10) 1.2174(3) 0.39226(9) 0.0235(4) Uani 1 1 d . . . C4 C -0.10146(10) 1.1779(3) 0.35394(9) 0.0204(4) Uani 1 1 d . . . C3 C -0.10494(10) 1.3389(4) 0.29710(9) 0.0236(4) Uani 1 1 d . . . O2 O 0.14983(8) 0.1767(3) 0.40546(9) 0.0416(4) Uani 1 1 d . . . C1 C -0.20539(11) 1.4138(4) 0.37349(10) 0.0275(4) Uani 1 1 d . . . H3 H -0.0702(10) 1.311(4) 0.2705(9) 0.016(5) Uiso 1 1 d . . . H9 H -0.2451(12) 1.702(4) 0.3050(11) 0.033(6) Uiso 1 1 d . . . H6 H -0.1590(11) 1.637(4) 0.2417(11) 0.029(6) Uiso 1 1 d . . . H12B H -0.0645(12) 0.834(4) 0.4487(11) 0.030(6) Uiso 1 1 d . . . H1 H -0.2371(13) 1.437(4) 0.4004(11) 0.037(6) Uiso 1 1 d . . . H12A H 0.0000(13) 0.704(5) 0.4339(12) 0.035(6) Uiso 1 1 d . . . H13 H 0.0286(15) 0.860(5) 0.3420(13) 0.043(8) Uiso 1 1 d . . . H12 H -0.1824(16) 1.098(5) 0.4635(15) 0.061(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 Cl1 0.0217(2) 0.0223(2) 0.0306(2) -0.00021(18) 0.01116(18) 0.00470(17) O13 0.0267(7) 0.0346(8) 0.0309(7) 0.0050(6) 0.0158(6) 0.0101(6) O12 0.0407(9) 0.0336(8) 0.0379(8) 0.0130(7) 0.0273(7) 0.0169(7) O11 0.0262(7) 0.0326(8) 0.0411(8) 0.0116(6) 0.0182(6) 0.0077(6) C10 0.0195(9) 0.0208(9) 0.0230(9) -0.0040(7) 0.0065(7) -0.0013(7) C9 0.0247(10) 0.0238(10) 0.0309(10) -0.0008(8) 0.0014(8) 0.0053(8) O8 0.0456(9) 0.0450(9) 0.0292(8) 0.0075(7) 0.0175(7) 0.0205(7) O7 0.0267(7) 0.0448(9) 0.0431(9) -0.0116(7) 0.0134(7) -0.0077(7) C6 0.0288(10) 0.0243(10) 0.0237(9) 0.0026(8) 0.0028(8) -0.0006(8) N12 0.0240(8) 0.0239(8) 0.0272(8) 0.0033(7) 0.0111(7) 0.0079(7) C5 0.0252(9) 0.0216(9) 0.0248(9) 0.0004(7) 0.0091(8) 0.0032(7) C4 0.0198(9) 0.0186(9) 0.0223(9) -0.0020(7) 0.0056(7) 0.0005(7) C3 0.0232(9) 0.0254(10) 0.0222(9) -0.0011(7) 0.0068(8) -0.0014(7) O2 0.0349(8) 0.0268(8) 0.0628(11) -0.0094(7) 0.0140(8) 0.0101(6) C1 0.0240(9) 0.0288(10) 0.0315(10) -0.0014(8) 0.0111(8) 0.0063(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 Cl1 O2 1.4191(15) . ? Cl1 O7 1.4302(15) . ? Cl1 O8 1.4489(14) . ? Cl1 O11 1.4491(13) . ? O13 C10 1.305(2) . ? O12 C5 1.354(2) . ? C10 N12 1.293(2) . ? C10 C4 1.462(2) . ? C9 C1 1.376(3) . ? C9 C6 1.385(3) . ? C6 C3 1.376(3) . ? C5 C1 1.390(3) . ? C5 C4 1.408(2) . ? C4 C3 1.404(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 O2 Cl1 O7 110.67(9) . . ? O2 Cl1 O8 109.70(9) . . ? O7 Cl1 O8 109.38(10) . . ? O2 Cl1 O11 110.12(9) . . ? O7 Cl1 O11 109.29(9) . . ? O8 Cl1 O11 107.62(8) . . ? N12 C10 O13 121.28(17) . . ? N12 C10 C4 123.43(16) . . ? O13 C10 C4 115.28(16) . . ? C1 C9 C6 121.04(18) . . ? C3 C6 C9 119.74(18) . . ? O12 C5 C1 121.58(17) . . ? O12 C5 C4 118.64(16) . . ? C1 C5 C4 119.78(17) . . ? C3 C4 C5 118.92(16) . . ? C3 C4 C10 118.75(16) . . ? C5 C4 C10 122.33(16) . . ? C6 C3 C4 120.54(17) . . ? C9 C1 C5 119.98(18) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.302 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 947744' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11178_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Acetaminophen hydrobromide monohydrate salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 Br N O3' _chemical_formula_weight 250.10 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.8473(4) _cell_length_b 23.1474(15) _cell_length_c 7.2982(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.9480(10) _cell_angle_gamma 90.00 _cell_volume 982.49(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5665 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 27.51 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 4.159 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.4614 _exptl_absorpt_correction_T_max 0.5214 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 11212 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2268 _reflns_number_gt 1963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0292P)^2^+0.4237P] 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 2268 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0619 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _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 Br1 Br 0.42976(4) 0.326406(9) 0.49785(3) 0.02504(9) Uani 1 1 d . . . C1 C -0.0007(4) 0.45571(9) 0.2446(3) 0.0198(4) Uani 1 1 d . . . N1 N -0.0113(3) 0.39402(8) 0.2398(3) 0.0225(4) Uani 1 1 d . . . C7 C -0.1704(4) 0.35918(10) 0.1634(3) 0.0221(5) Uani 1 1 d . . . C6 C 0.2100(4) 0.47902(10) 0.3143(3) 0.0236(5) Uani 1 1 d . . . O4 O 0.0789(3) 0.63356(7) 0.2715(3) 0.0280(4) Uani 1 1 d . . . C3 C -0.1503(4) 0.55135(10) 0.1952(3) 0.0236(5) Uani 1 1 d . . . C2 C -0.1812(4) 0.49210(10) 0.1848(3) 0.0227(5) Uani 1 1 d . . . C5 C 0.2400(4) 0.53804(10) 0.3248(3) 0.0238(5) Uani 1 1 d . . . C4 C 0.0596(4) 0.57467(9) 0.2661(3) 0.0216(4) Uani 1 1 d . . . O7 O -0.3555(3) 0.38055(7) 0.0807(2) 0.0247(4) Uani 1 1 d . . . C8 C -0.1301(4) 0.29582(10) 0.1712(4) 0.0278(5) Uani 1 1 d . . . H1 H 0.108(4) 0.3790(10) 0.296(3) 0.018(6) Uiso 1 1 d . . . H5 H 0.387(5) 0.5535(11) 0.371(3) 0.031(7) Uiso 1 1 d . . . H2 H -0.324(5) 0.4767(12) 0.131(4) 0.038(7) Uiso 1 1 d . . . H6 H 0.338(5) 0.4530(12) 0.358(4) 0.037(7) Uiso 1 1 d . . . H3 H -0.274(5) 0.5771(12) 0.158(3) 0.031(7) Uiso 1 1 d . . . H8C H 0.006(5) 0.2864(12) 0.253(4) 0.040(8) Uiso 1 1 d . . . H8B H -0.111(5) 0.2817(13) 0.059(4) 0.042(8) Uiso 1 1 d . . . H4 H 0.191(6) 0.6388(15) 0.320(5) 0.053(11) Uiso 1 1 d . . . H8A H -0.258(5) 0.2774(13) 0.222(4) 0.047(8) Uiso 1 1 d . . . H7 H -0.446(6) 0.3583(18) 0.047(5) 0.066(12) Uiso 1 1 d . . . O10 O 0.3481(3) 0.31090(9) -0.0549(3) 0.0325(4) Uani 1 1 d . . . H10B H 0.343(7) 0.3159(16) -0.159(6) 0.074(14) Uiso 1 1 d . . . H10A H 0.374(5) 0.2798(16) -0.041(4) 0.043(10) 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 Br1 0.02588(13) 0.01820(12) 0.02974(13) -0.00030(9) -0.00327(9) 0.00231(9) C1 0.0219(10) 0.0198(11) 0.0176(10) 0.0012(8) 0.0018(8) -0.0003(8) N1 0.0214(9) 0.0191(10) 0.0262(10) 0.0035(8) -0.0015(8) 0.0022(8) C7 0.0242(11) 0.0214(11) 0.0210(11) 0.0023(9) 0.0042(9) 0.0001(9) C6 0.0206(10) 0.0251(11) 0.0244(11) 0.0019(9) -0.0016(9) 0.0045(9) O4 0.0259(9) 0.0185(8) 0.0380(10) -0.0009(7) -0.0042(8) 0.0012(7) C3 0.0214(11) 0.0232(12) 0.0257(12) 0.0026(9) -0.0008(9) 0.0045(9) C2 0.0189(10) 0.0243(12) 0.0243(11) 0.0006(9) 0.0001(9) -0.0015(9) C5 0.0215(11) 0.0232(11) 0.0253(12) -0.0013(9) -0.0037(9) -0.0002(9) C4 0.0247(11) 0.0196(11) 0.0209(11) 0.0005(9) 0.0036(9) 0.0004(9) O7 0.0225(8) 0.0210(8) 0.0290(9) 0.0035(7) -0.0058(7) -0.0018(7) C8 0.0271(13) 0.0204(12) 0.0350(14) 0.0024(10) -0.0007(11) 0.0016(10) O10 0.0387(10) 0.0203(10) 0.0350(11) 0.0036(8) -0.0122(8) -0.0013(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 C2 1.385(3) . ? C1 C6 1.393(3) . ? C1 N1 1.429(3) . ? N1 C7 1.311(3) . ? C7 O7 1.283(3) . ? C7 C8 1.486(3) . ? C6 C5 1.378(3) . ? O4 C4 1.368(3) . ? C3 C2 1.384(3) . ? C3 C4 1.390(3) . ? C5 C4 1.386(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 C2 C1 C6 119.7(2) . . ? C2 C1 N1 124.8(2) . . ? C6 C1 N1 115.49(19) . . ? C7 N1 C1 130.7(2) . . ? O7 C7 N1 119.3(2) . . ? O7 C7 C8 121.4(2) . . ? N1 C7 C8 119.2(2) . . ? C5 C6 C1 120.4(2) . . ? C2 C3 C4 120.7(2) . . ? C3 C2 C1 119.6(2) . . ? C6 C5 C4 120.1(2) . . ? O4 C4 C5 122.9(2) . . ? O4 C4 C3 117.7(2) . . ? C5 C4 C3 119.4(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.732 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 947745' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11050_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Phenacetin hemi hydrochloride' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H27 Cl N2 O4' _chemical_formula_weight 394.89 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' Cl Cl 0.1484 0.1585 '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 26.813(5) _cell_length_b 5.6138(11) _cell_length_c 13.838(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.014(2) _cell_angle_gamma 90.00 _cell_volume 2082.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7694 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 27.53 _exptl_crystal_description Needles _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9513 _exptl_absorpt_correction_T_max 0.9692 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11859 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.57 _reflns_number_total 2384 _reflns_number_gt 2318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0790P)^2^+0.3431P] 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 2384 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 O4 O 0.25506(4) -0.4618(2) -0.10313(10) 0.0360(3) Uani 1 1 d . . . O7 O 0.03204(4) -0.8648(2) -0.02986(10) 0.0308(3) Uani 1 1 d . . . N1 N 0.04787(4) -0.5471(2) -0.12453(10) 0.0238(3) Uani 1 1 d . . . H1 H 0.0340 -0.4372 -0.1610 0.029 Uiso 1 1 calc R . . C41 C 0.27992(6) -0.2682(4) -0.14965(14) 0.0375(4) Uani 1 1 d . . . H41B H 0.2687 -0.1147 -0.1219 0.045 Uiso 1 1 calc R . . H41A H 0.2723 -0.2682 -0.2197 0.045 Uiso 1 1 calc R . . C42 C 0.33528(7) -0.3002(4) -0.13361(17) 0.0450(5) Uani 1 1 d . . . H42C H 0.3534 -0.1691 -0.1646 0.068 Uiso 1 1 calc R . . H42B H 0.3460 -0.4519 -0.1618 0.068 Uiso 1 1 calc R . . H42A H 0.3423 -0.3002 -0.0641 0.068 Uiso 1 1 calc R . . C2 C 0.13064(7) -0.6996(3) -0.06865(14) 0.0319(4) Uani 1 1 d . . . H2 H 0.1158 -0.8332 -0.0378 0.038 Uiso 1 1 calc R . . C7 C 0.01661(6) -0.7013(3) -0.08494(12) 0.0240(3) Uani 1 1 d . . . C5 C 0.17463(6) -0.3057(3) -0.15707(14) 0.0326(4) Uani 1 1 d . . . H5 H 0.1895 -0.1712 -0.1871 0.039 Uiso 1 1 calc R . . C3 C 0.18173(7) -0.6687(3) -0.06638(15) 0.0335(4) Uani 1 1 d . . . H3 H 0.2019 -0.7831 -0.0344 0.040 Uiso 1 1 calc R . . C6 C 0.12322(6) -0.3368(3) -0.15978(14) 0.0299(4) Uani 1 1 d . . . H6 H 0.1030 -0.2221 -0.1916 0.036 Uiso 1 1 calc R . . C4 C 0.20401(5) -0.4734(3) -0.11001(12) 0.0270(3) Uani 1 1 d . . . C1 C 0.10097(5) -0.5332(3) -0.11659(11) 0.0234(3) Uani 1 1 d . . . C8 C -0.03777(6) -0.6738(3) -0.10829(13) 0.0278(3) Uani 1 1 d . . . H8C H -0.0569 -0.7972 -0.0746 0.042 Uiso 1 1 calc R . . H8B H -0.0427 -0.6901 -0.1782 0.042 Uiso 1 1 calc R . . H8A H -0.0492 -0.5163 -0.0874 0.042 Uiso 1 1 calc R . . Cl1 Cl 0.0000 -0.14912(8) -0.2500 0.03176(16) Uani 1 2 d S . . H7 H 0.0106(13) -0.951(6) -0.012(3) 0.017(9) Uiso 0.50 1 d P . . 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 O4 0.0182(5) 0.0406(7) 0.0491(7) 0.0105(5) -0.0011(5) -0.0030(5) O7 0.0235(5) 0.0350(6) 0.0338(6) 0.0108(5) -0.0030(5) -0.0101(5) N1 0.0180(5) 0.0242(6) 0.0293(6) 0.0036(5) -0.0001(5) -0.0022(4) C41 0.0218(7) 0.0476(11) 0.0432(9) 0.0108(9) -0.0012(7) -0.0083(7) C42 0.0211(8) 0.0617(12) 0.0522(12) 0.0089(10) 0.0006(8) -0.0082(8) C2 0.0251(8) 0.0253(7) 0.0453(10) 0.0097(7) -0.0014(7) -0.0019(6) C7 0.0200(7) 0.0263(7) 0.0256(7) -0.0030(6) 0.0009(5) -0.0035(5) C5 0.0240(7) 0.0314(8) 0.0424(10) 0.0124(7) -0.0016(7) -0.0057(6) C3 0.0255(8) 0.0285(8) 0.0464(10) 0.0091(7) -0.0033(7) 0.0024(6) C6 0.0228(8) 0.0286(8) 0.0382(9) 0.0112(6) -0.0030(7) -0.0027(5) C4 0.0183(6) 0.0300(8) 0.0326(8) 0.0015(6) -0.0006(6) -0.0014(6) C1 0.0190(6) 0.0241(7) 0.0270(7) -0.0006(6) 0.0014(6) -0.0034(5) C8 0.0182(7) 0.0308(8) 0.0344(9) -0.0042(6) 0.0010(6) -0.0022(5) Cl1 0.0343(3) 0.0230(2) 0.0379(3) 0.000 -0.0088(3) 0.000 _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 O4 C4 1.3736(17) . ? O4 C41 1.428(2) . ? O7 C7 1.263(2) . ? N1 C7 1.324(2) . ? N1 C1 1.4301(17) . ? C41 C42 1.512(2) . ? C2 C3 1.381(2) . ? C2 C1 1.395(2) . ? C7 C8 1.501(2) . ? C5 C4 1.389(2) . ? C5 C6 1.390(2) . ? C3 C4 1.387(2) . ? C6 C1 1.389(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 C4 O4 C41 118.04(13) . . ? C7 N1 C1 129.36(13) . . ? O4 C41 C42 107.57(16) . . ? C3 C2 C1 119.49(15) . . ? O7 C7 N1 121.18(14) . . ? O7 C7 C8 121.52(15) . . ? N1 C7 C8 117.30(15) . . ? C4 C5 C6 119.31(15) . . ? C2 C3 C4 121.12(15) . . ? C1 C6 C5 120.95(14) . . ? O4 C4 C3 115.90(14) . . ? O4 C4 C5 124.41(14) . . ? C3 C4 C5 119.69(14) . . ? C6 C1 C2 119.43(13) . . ? C6 C1 N1 115.97(13) . . ? C2 C1 N1 124.60(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 C4 O4 C41 C42 -178.50(16) . . . . ? C1 N1 C7 O7 1.2(3) . . . . ? C1 N1 C7 C8 -178.77(14) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C41 O4 C4 C3 177.97(16) . . . . ? C41 O4 C4 C5 -1.8(3) . . . . ? C2 C3 C4 O4 -179.93(17) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C6 C5 C4 O4 179.68(17) . . . . ? C6 C5 C4 C3 -0.1(3) . . . . ? C5 C6 C1 C2 0.9(3) . . . . ? C5 C6 C1 N1 -179.63(16) . . . . ? C3 C2 C1 C6 -1.2(3) . . . . ? C3 C2 C1 N1 179.45(16) . . . . ? C7 N1 C1 C6 -174.30(16) . . . . ? C7 N1 C1 C2 5.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.248 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 947746' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11083_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Phenacetin hydrochloride salt trihydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H33 Cl2 N2 O7' _chemical_formula_weight 484.38 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7923(4) _cell_length_b 13.4759(8) _cell_length_c 14.1913(8) _cell_angle_alpha 76.1270(10) _cell_angle_beta 77.3120(10) _cell_angle_gamma 87.9620(10) _cell_volume 1230.08(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6761 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 27.60 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9360 _exptl_absorpt_correction_T_max 0.9557 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14262 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.63 _reflns_number_total 5614 _reflns_number_gt 4454 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] 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 5614 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.315 _refine_ls_restrained_S_all 1.315 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 0.21234(8) 0.94548(4) 0.08278(4) 0.03099(18) Uani 1 1 d . . . Cl2 Cl -0.67938(8) 1.05007(4) 0.39982(4) 0.03368(19) Uani 1 1 d . . . O29 O -0.1520(3) 1.02750(12) 0.19296(14) 0.0377(4) Uani 1 1 d . . . O28 O -0.4725(2) 1.33840(10) 0.06939(10) 0.0218(3) Uani 1 1 d . . . O27 O -1.1440(2) 1.44949(10) -0.19818(11) 0.0296(4) Uani 1 1 d . . . O26 O -1.0232(2) 0.65880(10) 0.42973(10) 0.0218(3) Uani 1 1 d . . . O25 O -0.4934(3) 0.95297(14) 0.22010(16) 0.0423(4) Uani 1 1 d . . . O24 O -0.1034(3) 1.01743(17) 0.36538(16) 0.0495(5) Uani 1 1 d . . . O23 O -0.3377(2) 0.55242(10) 0.69097(11) 0.0298(4) Uani 1 1 d . . . N22 N -0.4108(2) 0.71346(11) 0.61908(11) 0.0168(3) Uani 1 1 d . . . H22A H -0.3788 0.7782 0.6103 0.020 Uiso 1 1 calc R . . C21 C -0.8736(3) 0.67638(14) 0.47530(13) 0.0177(4) Uani 1 1 d . . . N20 N -1.0896(2) 1.28843(11) -0.11883(11) 0.0167(3) Uani 1 1 d . . . H20A H -1.1288 1.2242 -0.1070 0.020 Uiso 1 1 calc R . . C19 C -0.6507(3) 0.78122(14) 0.52172(13) 0.0187(4) Uani 1 1 d . . . H19A H -0.6025 0.8470 0.5202 0.022 Uiso 1 1 calc R . . C18 C -0.9297(3) 1.30496(14) -0.07360(13) 0.0164(4) Uani 1 1 d . . . C17 C -0.6225(3) 1.32159(14) 0.02359(13) 0.0177(4) Uani 1 1 d . . . C16 C -0.6871(3) 1.22519(14) 0.02157(14) 0.0195(4) Uani 1 1 d . . . H16A H -0.6272 1.1652 0.0532 0.023 Uiso 1 1 calc R . . C15 C -0.6381(3) 0.59809(14) 0.57542(14) 0.0202(4) Uani 1 1 d . . . H15A H -0.5827 0.5386 0.6106 0.024 Uiso 1 1 calc R . . C14 C -0.5676(3) 0.69531(14) 0.57285(13) 0.0166(4) Uani 1 1 d . . . C13 C -0.8031(3) 0.77313(14) 0.47261(14) 0.0196(4) Uani 1 1 d . . . H13A H -0.8585 0.8327 0.4377 0.024 Uiso 1 1 calc R . . C12 C -0.8400(3) 1.21814(14) -0.02733(13) 0.0189(4) Uani 1 1 d . . . H12A H -0.8843 1.1527 -0.0292 0.023 Uiso 1 1 calc R . . C11 C -0.8643(3) 1.40172(14) -0.07177(14) 0.0204(4) Uani 1 1 d . . . H11A H -0.9237 1.4616 -0.1038 0.024 Uiso 1 1 calc R . . C10 C -1.2696(3) 0.70622(16) 0.33237(15) 0.0243(4) Uani 1 1 d . . . H10A H -1.3333 0.7638 0.2942 0.036 Uiso 1 1 calc R . . H10B H -1.3722 0.6666 0.3868 0.036 Uiso 1 1 calc R . . H10C H -1.2059 0.6624 0.2887 0.036 Uiso 1 1 calc R . . C9 C -0.3066(3) 0.64830(14) 0.67283(14) 0.0188(4) Uani 1 1 d . . . C8 C -1.1871(3) 1.35414(14) -0.17526(14) 0.0184(4) Uani 1 1 d . . . C7 C -0.7118(3) 1.40912(14) -0.02270(14) 0.0196(4) Uani 1 1 d . . . H7A H -0.6678 1.4745 -0.0206 0.024 Uiso 1 1 calc R . . C6 C -1.1111(3) 0.74632(15) 0.37469(14) 0.0205(4) Uani 1 1 d . . . H6A H -1.0063 0.7866 0.3204 0.025 Uiso 1 1 calc R . . H6B H -1.1734 0.7909 0.4190 0.025 Uiso 1 1 calc R . . C5 C -1.3490(3) 1.31543(15) -0.21444(14) 0.0208(4) Uani 1 1 d . . . H5A H -1.4073 1.3730 -0.2554 0.031 Uiso 1 1 calc R . . H5B H -1.4547 1.2804 -0.1587 0.031 Uiso 1 1 calc R . . H5C H -1.2910 1.2676 -0.2549 0.031 Uiso 1 1 calc R . . C4 C -0.7897(3) 0.58937(14) 0.52614(14) 0.0199(4) Uani 1 1 d . . . H4A H -0.8368 0.5235 0.5270 0.024 Uiso 1 1 calc R . . C3 C -0.3862(3) 1.25030(15) 0.12512(14) 0.0201(4) Uani 1 1 d . . . H3A H -0.3214 1.2062 0.0809 0.024 Uiso 1 1 calc R . . H3B H -0.4922 1.2097 0.1784 0.024 Uiso 1 1 calc R . . C2 C -0.2313(3) 1.29066(16) 0.16930(15) 0.0243(4) Uani 1 1 d . . . H2A H -0.1682 1.2332 0.2080 0.036 Uiso 1 1 calc R . . H2B H -0.2976 1.3341 0.2128 0.036 Uiso 1 1 calc R . . H2C H -0.1277 1.3308 0.1157 0.036 Uiso 1 1 calc R . . C1 C -0.1503(3) 0.68923(15) 0.71408(14) 0.0209(4) Uani 1 1 d . . . H1A H -0.0858 0.6322 0.7526 0.031 Uiso 1 1 calc R . . H1B H -0.2147 0.7334 0.7573 0.031 Uiso 1 1 calc R . . H1C H -0.0483 0.7289 0.6593 0.031 Uiso 1 1 calc R . . H29C H -0.050(5) 0.994(2) 0.162(2) 0.064(9) Uiso 1 1 d . . . H25B H -0.571(6) 0.991(3) 0.271(3) 0.099(12) Uiso 1 1 d . . . H24B H -0.179(5) 1.005(3) 0.415(3) 0.079(13) Uiso 1 1 d . . . H24A H 0.010(5) 1.027(2) 0.370(2) 0.049(9) Uiso 1 1 d . . . H29B H -0.296(5) 1.003(2) 0.199(2) 0.058(8) Uiso 1 1 d . . . H25A H -0.542(5) 0.962(2) 0.171(3) 0.063(10) Uiso 1 1 d . . . H29A H -0.152(5) 1.015(2) 0.263(2) 0.069(10) 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 Cl1 0.0298(3) 0.0186(3) 0.0486(3) -0.0053(2) -0.0197(2) -0.00155(19) Cl2 0.0429(3) 0.0191(3) 0.0444(3) -0.0029(2) -0.0251(3) -0.0039(2) O29 0.0364(9) 0.0334(9) 0.0496(11) -0.0122(8) -0.0206(8) 0.0044(7) O28 0.0226(7) 0.0191(7) 0.0276(7) -0.0030(6) -0.0160(6) -0.0012(5) O27 0.0375(8) 0.0165(7) 0.0413(9) -0.0010(6) -0.0284(7) 0.0004(6) O26 0.0235(7) 0.0181(7) 0.0283(7) -0.0033(5) -0.0170(6) -0.0011(5) O25 0.0352(9) 0.0455(10) 0.0560(12) -0.0184(9) -0.0244(9) 0.0032(8) O24 0.0353(10) 0.0738(14) 0.0473(12) -0.0240(10) -0.0148(9) -0.0009(9) O23 0.0379(8) 0.0164(7) 0.0418(9) -0.0014(6) -0.0286(7) 0.0013(6) N22 0.0189(7) 0.0144(8) 0.0189(7) -0.0034(6) -0.0082(6) -0.0011(6) C21 0.0165(8) 0.0213(10) 0.0176(9) -0.0048(7) -0.0083(7) -0.0009(7) N20 0.0175(7) 0.0147(8) 0.0196(7) -0.0033(6) -0.0085(6) -0.0008(6) C19 0.0204(9) 0.0167(9) 0.0209(9) -0.0046(7) -0.0083(7) -0.0010(7) C18 0.0172(8) 0.0171(9) 0.0163(8) -0.0041(7) -0.0064(7) 0.0001(7) C17 0.0176(8) 0.0205(10) 0.0173(8) -0.0050(7) -0.0075(7) -0.0005(7) C16 0.0214(9) 0.0163(9) 0.0222(9) -0.0012(7) -0.0114(7) 0.0006(7) C15 0.0230(9) 0.0157(9) 0.0232(9) -0.0021(7) -0.0104(7) 0.0009(7) C14 0.0171(8) 0.0169(9) 0.0175(8) -0.0041(7) -0.0069(7) 0.0006(7) C13 0.0214(9) 0.0161(9) 0.0222(9) -0.0014(7) -0.0104(7) 0.0014(7) C12 0.0217(9) 0.0158(9) 0.0207(9) -0.0036(7) -0.0083(7) -0.0014(7) C11 0.0228(9) 0.0167(9) 0.0232(9) -0.0032(7) -0.0101(7) 0.0022(7) C10 0.0215(9) 0.0315(11) 0.0230(9) -0.0065(8) -0.0115(8) 0.0004(8) C9 0.0181(8) 0.0200(9) 0.0196(9) -0.0041(7) -0.0073(7) -0.0001(7) C8 0.0178(8) 0.0189(9) 0.0199(9) -0.0045(7) -0.0070(7) 0.0008(7) C7 0.0227(9) 0.0140(9) 0.0245(9) -0.0042(7) -0.0098(7) -0.0023(7) C6 0.0186(9) 0.0214(10) 0.0229(9) -0.0026(7) -0.0103(7) 0.0014(7) C5 0.0193(9) 0.0245(10) 0.0218(9) -0.0061(8) -0.0105(7) 0.0014(7) C4 0.0222(9) 0.0147(9) 0.0249(9) -0.0036(7) -0.0104(7) -0.0023(7) C3 0.0181(9) 0.0211(10) 0.0230(9) -0.0035(7) -0.0106(7) 0.0016(7) C2 0.0218(9) 0.0316(11) 0.0236(9) -0.0076(8) -0.0124(8) 0.0007(8) C1 0.0202(9) 0.0226(10) 0.0227(9) -0.0053(8) -0.0110(7) 0.0017(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 O28 C17 1.374(2) . ? O28 C3 1.443(2) . ? O27 C8 1.276(2) . ? O26 C21 1.373(2) . ? O26 C6 1.439(2) . ? O23 C9 1.271(2) . ? N22 C9 1.314(2) . ? N22 C14 1.424(2) . ? C21 C13 1.394(3) . ? C21 C4 1.396(3) . ? N20 C8 1.310(2) . ? N20 C18 1.426(2) . ? C19 C14 1.384(3) . ? C19 C13 1.389(2) . ? C18 C12 1.388(3) . ? C18 C11 1.400(2) . ? C17 C7 1.394(3) . ? C17 C16 1.394(3) . ? C16 C12 1.388(2) . ? C15 C4 1.388(3) . ? C15 C14 1.400(2) . ? C11 C7 1.388(3) . ? C10 C6 1.514(2) . ? C9 C1 1.497(2) . ? C8 C5 1.496(2) . ? C3 C2 1.514(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 C17 O28 C3 117.72(14) . . ? C21 O26 C6 117.58(14) . . ? C9 N22 C14 129.90(16) . . ? O26 C21 C13 124.41(17) . . ? O26 C21 C4 115.70(16) . . ? C13 C21 C4 119.89(16) . . ? C8 N20 C18 129.91(16) . . ? C14 C19 C13 121.33(17) . . ? C12 C18 C11 119.69(17) . . ? C12 C18 N20 116.37(15) . . ? C11 C18 N20 123.92(16) . . ? O28 C17 C7 115.52(15) . . ? O28 C17 C16 124.41(17) . . ? C7 C17 C16 120.07(16) . . ? C12 C16 C17 119.02(17) . . ? C4 C15 C14 119.44(18) . . ? C19 C14 C15 119.57(17) . . ? C19 C14 N22 116.08(16) . . ? C15 C14 N22 124.34(16) . . ? C19 C13 C21 119.13(17) . . ? C16 C12 C18 121.23(17) . . ? C7 C11 C18 119.27(18) . . ? O23 C9 N22 121.36(16) . . ? O23 C9 C1 120.08(16) . . ? N22 C9 C1 118.56(16) . . ? O27 C8 N20 121.11(16) . . ? O27 C8 C5 120.02(16) . . ? N20 C8 C5 118.86(16) . . ? C11 C7 C17 120.71(17) . . ? O26 C6 C10 106.95(15) . . ? C15 C4 C21 120.64(17) . . ? O28 C3 C2 106.56(15) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.681 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 947747' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12008_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Phenacetin hemi hydrobromide' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H54 Br2 N4 O8' _chemical_formula_weight 878.69 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' Br Br -0.2901 2.4595 '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3000(7) _cell_length_b 12.1554(7) _cell_length_c 28.5010(14) _cell_angle_alpha 90.00 _cell_angle_beta 111.742(2) _cell_angle_gamma 90.00 _cell_volume 4279.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9560 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.39 _exptl_crystal_description Needles _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 1.947 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.6117 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48114 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.45 _reflns_number_total 9746 _reflns_number_gt 7848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0358P)^2^+1.1817P] 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 9746 _refine_ls_number_parameters 703 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _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 O38 O -0.09037(11) 0.14561(11) 0.00410(4) 0.0449(3) Uani 1 1 d . . . O45 O -0.38991(11) -0.39617(11) -0.50146(4) 0.0440(3) Uani 1 1 d . . . O49 O -0.26125(9) -0.11619(9) -0.20679(4) 0.0299(3) Uani 1 1 d . . . O52 O -0.25300(9) -0.24454(9) -0.27076(4) 0.0298(3) Uani 1 1 d . . . N46 N -0.30649(12) 0.05974(12) -0.20047(5) 0.0293(3) Uani 1 1 d . . . N47 N -0.14920(12) -0.35896(12) -0.29540(5) 0.0289(3) Uani 1 1 d . . . C3 C -0.4495(2) -0.4733(2) -0.58351(8) 0.0525(6) Uani 1 1 d . . . C4 C -0.11717(18) 0.03742(17) -0.06687(7) 0.0474(5) Uani 1 1 d . . . C5 C -0.16813(17) 0.01136(17) -0.11716(7) 0.0445(5) Uani 1 1 d . . . C7 C -0.0471(2) 0.2337(2) 0.08282(8) 0.0497(5) Uani 1 1 d . . . C9 C -0.37521(19) -0.4888(2) -0.52929(8) 0.0478(5) Uani 1 1 d . . . C11 C -0.25271(16) -0.46930(16) -0.42479(7) 0.0401(5) Uani 1 1 d . . . C13 C -0.11694(18) 0.23913(18) 0.02752(7) 0.0428(5) Uani 1 1 d . . . C14 C -0.34629(16) -0.30126(16) -0.42529(7) 0.0378(4) Uani 1 1 d . . . C15 C -0.08658(15) -0.30690(16) -0.20761(7) 0.0314(4) Uani 1 1 d . . . C17 C -0.19569(15) -0.45640(15) -0.37337(7) 0.0359(4) Uani 1 1 d . . . C18 C -0.28906(16) -0.28782(15) -0.37437(7) 0.0364(4) Uani 1 1 d . . . C20 C -0.37352(16) -0.02433(16) -0.28280(7) 0.0335(4) Uani 1 1 d . . . C22 C -0.22662(15) 0.19759(15) -0.07701(7) 0.0357(4) Uani 1 1 d . . . C27 C -0.27832(15) 0.17172(15) -0.12770(6) 0.0327(4) Uani 1 1 d . . . C28 C -0.14575(15) 0.12948(15) -0.04629(6) 0.0347(4) Uani 1 1 d . . . C30 C -0.16783(13) -0.30129(13) -0.26011(6) 0.0267(3) Uani 1 1 d . . . C34 C -0.21304(13) -0.36649(13) -0.34787(6) 0.0283(3) Uani 1 1 d . . . C35 C -0.32888(14) -0.39152(15) -0.45089(6) 0.0341(4) Uani 1 1 d . . . C39 C -0.25046(13) 0.07863(14) -0.14799(6) 0.0284(3) Uani 1 1 d . . . C43 C -0.30952(13) -0.02892(13) -0.22727(6) 0.0272(3) Uani 1 1 d . . . O42 O 0.42056(11) -0.37749(11) 0.00997(5) 0.0465(3) Uani 1 1 d . . . O50 O 0.23764(9) -0.14410(9) -0.20764(4) 0.0293(3) Uani 1 1 d . . . N41 N 0.20164(11) -0.32101(12) -0.19682(5) 0.0291(3) Uani 1 1 d . . . C1 C 0.4616(2) -0.4518(3) 0.09147(8) 0.0570(6) Uani 1 1 d . . . C8 C 0.39393(17) -0.28222(17) -0.06453(7) 0.0447(5) Uani 1 1 d . . . C12 C 0.34221(17) -0.26373(16) -0.11567(7) 0.0419(5) Uani 1 1 d . . . C19 C 0.36433(15) -0.36859(15) -0.04085(6) 0.0357(4) Uani 1 1 d . . . C24 C 0.39220(18) -0.4647(2) 0.03636(7) 0.0458(5) Uani 1 1 d . . . C26 C 0.12930(16) -0.24613(16) -0.28117(7) 0.0325(4) Uani 1 1 d . . . C29 C 0.28223(15) -0.43911(16) -0.06910(7) 0.0366(4) Uani 1 1 d . . . C31 C 0.25849(13) -0.33289(14) -0.14378(6) 0.0284(3) Uani 1 1 d . . . C33 C 0.23020(15) -0.42024(15) -0.12049(7) 0.0343(4) Uani 1 1 d . . . C48 C 0.19371(13) -0.23488(13) -0.22589(6) 0.0267(3) Uani 1 1 d . . . O40 O 0.90036(11) -0.37212(11) 0.00722(5) 0.0452(3) Uani 1 1 d . . . O51 O 0.75874(9) -0.52119(9) -0.22546(4) 0.0308(3) Uani 1 1 d . . . N44 N 0.65938(12) -0.40396(12) -0.19916(5) 0.0297(3) Uani 1 1 d . . . C2 C 0.9547(2) -0.3001(3) 0.09013(8) 0.0573(6) Uani 1 1 d . . . C6 C 0.85854(16) -0.46369(16) -0.06966(7) 0.0378(4) Uani 1 1 d . . . C10 C 0.88193(19) -0.2827(2) 0.03596(8) 0.0486(5) Uani 1 1 d . . . C16 C 0.80147(16) -0.47585(15) -0.12088(7) 0.0361(4) Uani 1 1 d . . . C21 C 0.83930(15) -0.37544(15) -0.04346(6) 0.0350(4) Uani 1 1 d . . . C23 C 0.76167(16) -0.29787(17) -0.06908(7) 0.0403(4) Uani 1 1 d . . . C25 C 0.70527(15) -0.30968(16) -0.12047(7) 0.0373(4) Uani 1 1 d . . . C32 C 0.67585(13) -0.46161(13) -0.23518(6) 0.0278(3) Uani 1 1 d . . . C36 C 0.59347(15) -0.45256(15) -0.28754(7) 0.0307(4) Uani 1 1 d . . . C37 C 0.72393(13) -0.39774(14) -0.14678(6) 0.0290(4) Uani 1 1 d . . . Br1 Br -0.053290(14) -0.035722(14) -0.250310(7) 0.03756(6) Uani 1 1 d . . . Br2 Br 0.454647(14) -0.230396(14) -0.240397(7) 0.03687(6) Uani 1 1 d . . . H41 H 0.1673(16) -0.3785(16) -0.2106(7) 0.039(6) Uiso 1 1 d . . . H46 H -0.3402(15) 0.1109(16) -0.2154(7) 0.032(5) Uiso 1 1 d . . . H26C H 0.1029(15) -0.3170(17) -0.2885(7) 0.038(5) Uiso 1 1 d . . . H17 H -0.1443(17) -0.5075(17) -0.3555(7) 0.042(5) Uiso 1 1 d . . . H18 H -0.2955(17) -0.2262(17) -0.3580(8) 0.046(6) Uiso 1 1 d . . . H11 H -0.2382(16) -0.5290(16) -0.4402(7) 0.038(5) Uiso 1 1 d . . . H25 H 0.6555(18) -0.2575(17) -0.1370(8) 0.048(6) Uiso 1 1 d . . . H20C H -0.4050(17) 0.0444(17) -0.2929(7) 0.043(6) Uiso 1 1 d . . . H12 H 0.3635(17) -0.2085(17) -0.1304(8) 0.046(6) Uiso 1 1 d . . . H33 H 0.1775(16) -0.4680(16) -0.1393(7) 0.040(5) Uiso 1 1 d . . . H20B H -0.3254(17) -0.0424(16) -0.2999(8) 0.045(6) Uiso 1 1 d . . . H27 H -0.3327(16) 0.2186(16) -0.1491(7) 0.039(5) Uiso 1 1 d . . . H36C H 0.5502(17) -0.3888(18) -0.2919(7) 0.047(6) Uiso 1 1 d . . . H44 H 0.6026(16) -0.3584(16) -0.2089(7) 0.039(5) Uiso 1 1 d . . . H29 H 0.2624(16) -0.4993(17) -0.0527(8) 0.046(6) Uiso 1 1 d . . . H15B H -0.0413(17) -0.3683(18) -0.2027(8) 0.050(6) Uiso 1 1 d . . . H36B H 0.5494(17) -0.5162(18) -0.2930(8) 0.046(6) Uiso 1 1 d . . . H36A H 0.6276(17) -0.4506(17) -0.3113(8) 0.049(6) Uiso 1 1 d . . . H14 H -0.3963(17) -0.2496(16) -0.4437(8) 0.042(5) Uiso 1 1 d . . . H26B H 0.1761(18) -0.2262(17) -0.2993(8) 0.050(6) Uiso 1 1 d . . . H26A H 0.0728(17) -0.1977(18) -0.2878(8) 0.047(6) Uiso 1 1 d . . . H6 H 0.9106(17) -0.5168(17) -0.0525(8) 0.049(6) Uiso 1 1 d . . . H3A H -0.526(2) -0.4694(18) -0.5862(9) 0.060(7) Uiso 1 1 d . . . H16 H 0.8137(18) -0.5351(19) -0.1372(8) 0.060(7) Uiso 1 1 d . . . H23 H 0.7465(17) -0.2382(17) -0.0525(8) 0.050(6) Uiso 1 1 d . . . H15 H -0.0461(18) -0.2431(18) -0.2032(8) 0.050(6) Uiso 1 1 d . . . H47 H -0.0930(17) -0.4001(16) -0.2847(7) 0.042(6) Uiso 1 1 d . . . H7A H 0.028(2) 0.2347(17) 0.0876(8) 0.051(6) Uiso 1 1 d . . . H22 H -0.2468(17) 0.2633(17) -0.0642(8) 0.049(6) Uiso 1 1 d . . . H13A H -0.2004(19) 0.2344(16) 0.0200(8) 0.050(6) Uiso 1 1 d . . . H1A H 0.538(2) -0.4572(18) 0.0972(9) 0.059(7) Uiso 1 1 d . . . H10A H 0.8035(19) -0.2846(18) 0.0314(8) 0.057(7) Uiso 1 1 d . . . H24A H 0.3142(19) -0.4584(17) 0.0319(8) 0.053(6) Uiso 1 1 d . . . H20A H -0.4260(17) -0.0774(18) -0.2895(8) 0.048(6) Uiso 1 1 d . . . H8 H 0.4519(19) -0.2363(19) -0.0445(9) 0.063(7) Uiso 1 1 d . . . H5 H -0.1477(18) -0.0479(18) -0.1301(8) 0.055(6) Uiso 1 1 d . . . H13B H -0.1054(17) 0.3022(18) 0.0112(8) 0.045(6) Uiso 1 1 d . . . H2C H 0.940(2) -0.371(2) 0.1016(10) 0.084(10) Uiso 1 1 d . . . H7C H -0.061(2) 0.295(2) 0.0990(10) 0.074(8) Uiso 1 1 d . . . H2B H 1.033(2) -0.300(2) 0.0948(9) 0.065(7) Uiso 1 1 d . . . H9B H -0.295(2) -0.4876(19) -0.5240(8) 0.059(7) Uiso 1 1 d . . . H15C H -0.1192(18) -0.3107(18) -0.1841(8) 0.053(6) Uiso 1 1 d . . . H4 H -0.062(2) -0.0054(19) -0.0453(9) 0.062(7) Uiso 1 1 d . . . H3C H -0.434(2) -0.402(2) -0.5959(9) 0.074(8) Uiso 1 1 d . . . H7B H -0.063(2) 0.162(2) 0.0969(9) 0.073(8) Uiso 1 1 d . . . H50 H 0.239(2) -0.090(3) -0.2366(11) 0.106(10) Uiso 1 1 d . . . H24B H 0.4039(18) -0.5347(19) 0.0222(8) 0.054(7) Uiso 1 1 d . . . H9A H -0.3926(19) -0.553(2) -0.5148(9) 0.060(7) Uiso 1 1 d . . . H3B H -0.442(2) -0.536(2) -0.6015(10) 0.077(8) Uiso 1 1 d . . . H49 H -0.257(2) -0.174(3) -0.2333(11) 0.102(10) Uiso 1 1 d . . . H10B H 0.8966(19) -0.2158(19) 0.0221(9) 0.056(7) Uiso 1 1 d . . . H1C H 0.450(2) -0.377(2) 0.1043(10) 0.083(9) Uiso 1 1 d . . . H2A H 0.950(2) -0.241(2) 0.1102(11) 0.087(9) Uiso 1 1 d . . . H1B H 0.453(2) -0.512(2) 0.1111(11) 0.093(10) 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 O38 0.0519(8) 0.0466(8) 0.0238(6) -0.0080(6) -0.0005(6) 0.0145(6) O45 0.0492(8) 0.0492(8) 0.0258(6) -0.0040(6) 0.0048(6) 0.0160(6) O49 0.0351(6) 0.0279(6) 0.0244(6) -0.0030(5) 0.0084(5) 0.0031(5) O52 0.0297(6) 0.0289(6) 0.0284(6) -0.0065(5) 0.0079(5) 0.0005(5) N46 0.0304(8) 0.0280(8) 0.0243(7) -0.0011(6) 0.0042(6) 0.0058(6) N47 0.0298(8) 0.0286(8) 0.0261(7) 0.0005(6) 0.0078(6) 0.0060(6) C3 0.0543(14) 0.0642(16) 0.0301(10) -0.0093(10) 0.0052(10) 0.0098(12) C4 0.0509(12) 0.0434(12) 0.0314(10) -0.0055(8) -0.0042(9) 0.0210(9) C5 0.0499(12) 0.0386(11) 0.0330(10) -0.0097(8) 0.0013(9) 0.0193(9) C7 0.0506(14) 0.0608(15) 0.0309(10) -0.0124(10) 0.0071(9) 0.0033(11) C9 0.0514(13) 0.0543(14) 0.0300(10) -0.0098(9) 0.0059(9) 0.0136(11) C11 0.0467(11) 0.0367(10) 0.0317(9) -0.0070(8) 0.0086(8) 0.0124(8) C13 0.0486(12) 0.0462(12) 0.0281(9) -0.0094(9) 0.0078(9) 0.0076(9) C14 0.0435(11) 0.0380(10) 0.0299(9) 0.0043(8) 0.0111(8) 0.0142(8) C15 0.0341(10) 0.0284(9) 0.0283(9) -0.0021(7) 0.0076(8) -0.0004(8) C17 0.0390(10) 0.0341(10) 0.0299(9) 0.0007(7) 0.0071(8) 0.0122(8) C18 0.0465(11) 0.0319(10) 0.0307(9) -0.0002(7) 0.0141(8) 0.0119(8) C20 0.0366(10) 0.0334(10) 0.0248(9) -0.0022(7) 0.0048(8) 0.0005(8) C22 0.0407(10) 0.0321(9) 0.0296(9) -0.0060(7) 0.0078(8) 0.0097(8) C27 0.0345(9) 0.0317(9) 0.0278(9) -0.0014(7) 0.0068(7) 0.0092(7) C28 0.0373(10) 0.0370(10) 0.0236(8) -0.0040(7) 0.0040(7) 0.0026(8) C30 0.0297(9) 0.0227(8) 0.0276(8) -0.0016(6) 0.0103(7) -0.0044(7) C34 0.0302(9) 0.0303(9) 0.0245(8) 0.0004(6) 0.0102(7) 0.0016(7) C35 0.0360(9) 0.0391(10) 0.0249(8) -0.0006(7) 0.0086(7) 0.0055(8) C39 0.0289(8) 0.0306(9) 0.0225(8) -0.0029(6) 0.0055(7) 0.0006(7) C43 0.0239(8) 0.0301(9) 0.0270(8) -0.0022(7) 0.0087(7) -0.0027(6) O42 0.0506(8) 0.0544(9) 0.0247(6) 0.0081(6) 0.0025(6) -0.0131(7) O50 0.0339(6) 0.0275(6) 0.0255(6) 0.0025(5) 0.0097(5) -0.0030(5) N41 0.0294(8) 0.0288(8) 0.0243(7) 0.0014(6) 0.0046(6) -0.0047(6) C1 0.0539(15) 0.0836(19) 0.0282(10) 0.0131(11) 0.0091(10) -0.0038(13) C8 0.0473(12) 0.0412(11) 0.0320(10) 0.0044(8) -0.0011(9) -0.0162(9) C12 0.0466(11) 0.0374(11) 0.0316(9) 0.0091(8) 0.0028(8) -0.0158(9) C19 0.0374(10) 0.0392(10) 0.0255(9) 0.0047(7) 0.0061(7) -0.0018(8) C24 0.0435(12) 0.0606(14) 0.0308(10) 0.0128(9) 0.0109(9) -0.0040(10) C26 0.0346(10) 0.0333(10) 0.0255(9) 0.0015(7) 0.0063(8) 0.0009(8) C29 0.0391(10) 0.0378(10) 0.0298(9) 0.0070(8) 0.0093(8) -0.0071(8) C31 0.0279(8) 0.0296(9) 0.0244(8) 0.0024(6) 0.0060(7) -0.0007(7) C33 0.0335(9) 0.0348(10) 0.0303(9) 0.0027(7) 0.0069(8) -0.0074(8) C48 0.0241(8) 0.0296(9) 0.0270(8) 0.0010(7) 0.0102(7) 0.0022(6) O40 0.0497(8) 0.0533(9) 0.0261(6) -0.0036(6) 0.0065(6) 0.0160(7) O51 0.0300(6) 0.0307(6) 0.0288(6) -0.0062(5) 0.0076(5) 0.0018(5) N44 0.0303(8) 0.0307(8) 0.0268(7) 0.0004(6) 0.0089(6) 0.0059(6) C2 0.0574(15) 0.0773(18) 0.0307(11) -0.0114(12) 0.0089(10) 0.0097(13) C6 0.0440(11) 0.0384(10) 0.0293(9) 0.0047(8) 0.0117(8) 0.0136(8) C10 0.0477(13) 0.0598(15) 0.0339(10) -0.0109(10) 0.0100(9) 0.0120(11) C16 0.0447(11) 0.0331(10) 0.0309(9) 0.0013(8) 0.0142(8) 0.0112(8) C21 0.0369(10) 0.0403(10) 0.0268(9) 0.0008(7) 0.0106(7) 0.0048(8) C23 0.0442(11) 0.0400(11) 0.0336(10) -0.0066(8) 0.0110(8) 0.0115(9) C25 0.0372(10) 0.0370(10) 0.0346(10) -0.0006(8) 0.0099(8) 0.0129(8) C32 0.0309(9) 0.0229(8) 0.0292(8) -0.0004(6) 0.0104(7) -0.0042(7) C36 0.0319(9) 0.0277(9) 0.0297(9) -0.0020(7) 0.0082(7) -0.0022(8) C37 0.0301(9) 0.0313(9) 0.0257(8) 0.0006(7) 0.0103(7) 0.0011(7) Br1 0.02955(10) 0.02725(9) 0.04823(11) 0.00608(7) 0.00549(8) -0.00121(7) Br2 0.02917(10) 0.02827(10) 0.04573(11) -0.00679(7) 0.00522(8) 0.00157(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 O38 C28 1.364(2) . ? O38 C13 1.427(2) . ? O45 C35 1.369(2) . ? O45 C9 1.432(2) . ? O49 C43 1.2651(19) . ? O49 H49 1.05(3) . ? O52 C30 1.2635(19) . ? O52 H49 1.38(3) . ? N46 C43 1.313(2) . ? N46 C39 1.421(2) . ? N46 H46 0.792(19) . ? N47 C30 1.322(2) . ? N47 C34 1.423(2) . ? N47 H47 0.86(2) . ? C3 C9 1.506(3) . ? C3 H3A 0.99(3) . ? C3 H3C 0.99(3) . ? C3 H3B 0.94(3) . ? C4 C5 1.376(3) . ? C4 C28 1.381(3) . ? C4 H4 0.93(2) . ? C5 C39 1.388(2) . ? C5 H5 0.90(2) . ? C7 C13 1.506(3) . ? C7 H7A 0.96(2) . ? C7 H7C 0.93(3) . ? C7 H7B 1.01(3) . ? C9 H9B 1.02(2) . ? C9 H9A 0.95(2) . ? C11 C35 1.384(2) . ? C11 C17 1.387(2) . ? C11 H11 0.91(2) . ? C13 H13A 1.05(2) . ? C13 H13B 0.94(2) . ? C14 C18 1.376(2) . ? C14 C35 1.384(2) . ? C14 H14 0.92(2) . ? C15 C30 1.488(2) . ? C15 H15B 0.94(2) . ? C15 H15 0.93(2) . ? C15 H15C 0.92(2) . ? C17 C34 1.378(2) . ? C17 H17 0.92(2) . ? C18 C34 1.393(2) . ? C18 H18 0.90(2) . ? C20 C43 1.495(2) . ? C20 H20C 0.93(2) . ? C20 H20B 0.96(2) . ? C20 H20A 0.92(2) . ? C22 C28 1.382(2) . ? C22 C27 1.387(2) . ? C22 H22 0.96(2) . ? C27 C39 1.382(2) . ? C27 H27 0.95(2) . ? O42 C19 1.366(2) . ? O42 C24 1.429(2) . ? O50 C48 1.2666(19) . ? O50 H50 1.06(3) . ? N41 C48 1.315(2) . ? N41 C31 1.425(2) . ? N41 H41 0.85(2) . ? C1 C24 1.506(3) . ? C1 H1A 0.98(2) . ? C1 H1C 1.02(3) . ? C1 H1B 0.95(3) . ? C8 C12 1.380(3) . ? C8 C19 1.382(3) . ? C8 H8 0.95(2) . ? C12 C31 1.388(2) . ? C12 H12 0.89(2) . ? C19 C29 1.387(2) . ? C24 H24A 1.00(2) . ? C24 H24B 0.98(2) . ? C26 C48 1.495(2) . ? C26 H26C 0.92(2) . ? C26 H26B 0.97(2) . ? C26 H26A 0.92(2) . ? C29 C33 1.388(2) . ? C29 H29 0.96(2) . ? C31 C33 1.376(2) . ? C33 H33 0.92(2) . ? O40 C21 1.371(2) . ? O40 C10 1.436(2) . ? O51 C32 1.261(2) . ? N44 C32 1.327(2) . ? N44 C37 1.422(2) . ? N44 H44 0.89(2) . ? C2 C10 1.503(3) . ? C2 H2C 0.96(3) . ? C2 H2B 1.00(3) . ? C2 H2A 0.94(3) . ? C6 C16 1.381(2) . ? C6 C21 1.384(3) . ? C6 H6 0.94(2) . ? C10 H10A 1.00(2) . ? C10 H10B 0.96(2) . ? C16 C37 1.395(2) . ? C16 H16 0.90(2) . ? C21 C23 1.389(3) . ? C23 C25 1.384(3) . ? C23 H23 0.93(2) . ? C25 C37 1.381(2) . ? C25 H25 0.91(2) . ? C32 C36 1.493(2) . ? C36 H36C 0.95(2) . ? C36 H36B 0.95(2) . ? C36 H36A 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 C28 O38 C13 118.44(14) . . ? C35 O45 C9 117.80(14) . . ? C43 O49 H49 112.5(16) . . ? C30 O52 H49 116.1(12) . . ? C43 N46 C39 129.50(15) . . ? C43 N46 H46 116.3(14) . . ? C39 N46 H46 114.2(14) . . ? C30 N47 C34 128.78(15) . . ? C30 N47 H47 115.0(13) . . ? C34 N47 H47 116.1(13) . . ? C9 C3 H3A 110.4(14) . . ? C9 C3 H3C 109.3(15) . . ? H3A C3 H3C 106(2) . . ? C9 C3 H3B 107.1(16) . . ? H3A C3 H3B 108(2) . . ? H3C C3 H3B 116(2) . . ? C5 C4 C28 121.47(17) . . ? C5 C4 H4 121.7(14) . . ? C28 C4 H4 116.8(14) . . ? C4 C5 C39 119.50(17) . . ? C4 C5 H5 120.4(14) . . ? C39 C5 H5 120.1(14) . . ? C13 C7 H7A 110.8(13) . . ? C13 C7 H7C 109.0(16) . . ? H7A C7 H7C 108(2) . . ? C13 C7 H7B 108.3(14) . . ? H7A C7 H7B 108.2(19) . . ? H7C C7 H7B 113(2) . . ? O45 C9 C3 107.28(18) . . ? O45 C9 H9B 104.9(13) . . ? C3 C9 H9B 113.6(13) . . ? O45 C9 H9A 107.4(14) . . ? C3 C9 H9A 112.1(14) . . ? H9B C9 H9A 111.0(19) . . ? C35 C11 C17 119.70(17) . . ? C35 C11 H11 122.1(12) . . ? C17 C11 H11 118.2(12) . . ? O38 C13 C7 106.93(17) . . ? O38 C13 H13A 106.7(11) . . ? C7 C13 H13A 113.9(12) . . ? O38 C13 H13B 107.8(13) . . ? C7 C13 H13B 113.8(13) . . ? H13A C13 H13B 107.3(17) . . ? C18 C14 C35 120.99(17) . . ? C18 C14 H14 121.3(13) . . ? C35 C14 H14 117.7(13) . . ? C30 C15 H15B 112.0(13) . . ? C30 C15 H15 105.4(13) . . ? H15B C15 H15 109.7(18) . . ? C30 C15 H15C 111.7(13) . . ? H15B C15 H15C 107.4(18) . . ? H15 C15 H15C 110.5(19) . . ? C34 C17 C11 120.92(17) . . ? C34 C17 H17 118.5(12) . . ? C11 C17 H17 120.6(12) . . ? C14 C18 C34 119.80(17) . . ? C14 C18 H18 121.5(13) . . ? C34 C18 H18 118.6(13) . . ? C43 C20 H20C 112.0(12) . . ? C43 C20 H20B 107.7(12) . . ? H20C C20 H20B 110.8(17) . . ? C43 C20 H20A 106.5(13) . . ? H20C C20 H20A 110.3(18) . . ? H20B C20 H20A 109.4(17) . . ? C28 C22 C27 119.56(16) . . ? C28 C22 H22 121.3(13) . . ? C27 C22 H22 119.1(13) . . ? C39 C27 C22 121.01(16) . . ? C39 C27 H27 118.9(12) . . ? C22 C27 H27 120.1(12) . . ? O38 C28 C4 115.96(16) . . ? O38 C28 C22 124.82(16) . . ? C4 C28 C22 119.23(16) . . ? O52 C30 N47 120.71(15) . . ? O52 C30 C15 121.27(15) . . ? N47 C30 C15 118.02(15) . . ? C17 C34 C18 119.21(15) . . ? C17 C34 N47 116.98(15) . . ? C18 C34 N47 123.79(15) . . ? O45 C35 C14 115.99(15) . . ? O45 C35 C11 124.63(16) . . ? C14 C35 C11 119.37(16) . . ? C27 C39 C5 119.21(15) . . ? C27 C39 N46 117.08(15) . . ? C5 C39 N46 123.66(15) . . ? O49 C43 N46 121.25(15) . . ? O49 C43 C20 120.83(15) . . ? N46 C43 C20 117.91(15) . . ? C19 O42 C24 117.98(15) . . ? C48 O50 H50 110.9(17) . . ? C48 N41 C31 129.51(15) . . ? C48 N41 H41 117.4(13) . . ? C31 N41 H41 113.0(13) . . ? C24 C1 H1A 111.6(14) . . ? C24 C1 H1C 110.7(15) . . ? H1A C1 H1C 107(2) . . ? C24 C1 H1B 112.0(18) . . ? H1A C1 H1B 101(2) . . ? H1C C1 H1B 114(2) . . ? C12 C8 C19 121.24(17) . . ? C12 C8 H8 121.0(14) . . ? C19 C8 H8 117.8(14) . . ? C8 C12 C31 119.35(17) . . ? C8 C12 H12 119.9(13) . . ? C31 C12 H12 120.8(13) . . ? O42 C19 C8 115.77(16) . . ? O42 C19 C29 124.78(16) . . ? C8 C19 C29 119.45(16) . . ? O42 C24 C1 107.01(18) . . ? O42 C24 H24A 109.8(12) . . ? C1 C24 H24A 109.4(12) . . ? O42 C24 H24B 108.4(13) . . ? C1 C24 H24B 112.9(13) . . ? H24A C24 H24B 109.3(18) . . ? C48 C26 H26C 110.2(12) . . ? C48 C26 H26B 107.8(13) . . ? H26C C26 H26B 112.0(17) . . ? C48 C26 H26A 105.4(13) . . ? H26C C26 H26A 109.7(18) . . ? H26B C26 H26A 111.5(17) . . ? C19 C29 C33 119.20(17) . . ? C19 C29 H29 119.3(12) . . ? C33 C29 H29 121.5(12) . . ? C33 C31 C12 119.54(16) . . ? C33 C31 N41 117.22(15) . . ? C12 C31 N41 123.20(15) . . ? C31 C33 C29 121.20(17) . . ? C31 C33 H33 119.6(12) . . ? C29 C33 H33 119.2(12) . . ? O50 C48 N41 121.19(15) . . ? O50 C48 C26 120.63(15) . . ? N41 C48 C26 118.17(15) . . ? C21 O40 C10 117.64(14) . . ? C32 N44 C37 129.20(15) . . ? C32 N44 H44 116.7(12) . . ? C37 N44 H44 113.9(12) . . ? C10 C2 H2C 109.8(17) . . ? C10 C2 H2B 112.3(14) . . ? H2C C2 H2B 107(2) . . ? C10 C2 H2A 110.7(18) . . ? H2C C2 H2A 114(2) . . ? H2B C2 H2A 103(2) . . ? C16 C6 C21 120.93(17) . . ? C16 C6 H6 119.1(13) . . ? C21 C6 H6 120.0(13) . . ? O40 C10 C2 107.35(18) . . ? O40 C10 H10A 107.3(13) . . ? C2 C10 H10A 111.9(13) . . ? O40 C10 H10B 107.7(14) . . ? C2 C10 H10B 113.1(14) . . ? H10A C10 H10B 109.1(19) . . ? C6 C16 C37 119.70(17) . . ? C6 C16 H16 119.7(14) . . ? C37 C16 H16 120.6(15) . . ? O40 C21 C6 115.82(16) . . ? O40 C21 C23 124.66(16) . . ? C6 C21 C23 119.52(16) . . ? C25 C23 C21 119.46(17) . . ? C25 C23 H23 119.0(13) . . ? C21 C23 H23 121.5(13) . . ? C37 C25 C23 121.27(17) . . ? C37 C25 H25 120.1(13) . . ? C23 C25 H25 118.7(13) . . ? O51 C32 N44 120.99(15) . . ? O51 C32 C36 121.34(15) . . ? N44 C32 C36 117.66(15) . . ? C32 C36 H36C 112.1(12) . . ? C32 C36 H36B 106.5(12) . . ? H36C C36 H36B 109.8(18) . . ? C32 C36 H36A 110.4(13) . . ? H36C C36 H36A 108.5(17) . . ? H36B C36 H36A 109.6(17) . . ? C25 C37 C16 119.11(16) . . ? C25 C37 N44 116.82(15) . . ? C16 C37 N44 124.05(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 C28 C4 C5 C39 -0.3(4) . . . . ? C35 O45 C9 C3 -179.03(19) . . . . ? C28 O38 C13 C7 177.84(19) . . . . ? C35 C11 C17 C34 -0.6(3) . . . . ? C35 C14 C18 C34 -0.6(3) . . . . ? C28 C22 C27 C39 0.2(3) . . . . ? C13 O38 C28 C4 -179.6(2) . . . . ? C13 O38 C28 C22 0.2(3) . . . . ? C5 C4 C28 O38 179.1(2) . . . . ? C5 C4 C28 C22 -0.7(3) . . . . ? C27 C22 C28 O38 -179.07(18) . . . . ? C27 C22 C28 C4 0.7(3) . . . . ? C34 N47 C30 O52 1.7(3) . . . . ? C34 N47 C30 C15 -179.30(16) . . . . ? C11 C17 C34 C18 0.0(3) . . . . ? C11 C17 C34 N47 -178.69(18) . . . . ? C14 C18 C34 C17 0.6(3) . . . . ? C14 C18 C34 N47 179.21(17) . . . . ? C30 N47 C34 C17 -159.84(17) . . . . ? C30 N47 C34 C18 21.5(3) . . . . ? C9 O45 C35 C14 -179.38(19) . . . . ? C9 O45 C35 C11 1.0(3) . . . . ? C18 C14 C35 O45 -179.67(18) . . . . ? C18 C14 C35 C11 0.0(3) . . . . ? C17 C11 C35 O45 -179.74(19) . . . . ? C17 C11 C35 C14 0.6(3) . . . . ? C22 C27 C39 C5 -1.1(3) . . . . ? C22 C27 C39 N46 -178.95(17) . . . . ? C4 C5 C39 C27 1.1(3) . . . . ? C4 C5 C39 N46 178.8(2) . . . . ? C43 N46 C39 C27 -167.42(17) . . . . ? C43 N46 C39 C5 14.9(3) . . . . ? C39 N46 C43 O49 2.8(3) . . . . ? C39 N46 C43 C20 -178.26(17) . . . . ? C19 C8 C12 C31 0.3(3) . . . . ? C24 O42 C19 C8 179.3(2) . . . . ? C24 O42 C19 C29 -0.9(3) . . . . ? C12 C8 C19 O42 -179.2(2) . . . . ? C12 C8 C19 C29 1.0(3) . . . . ? C19 O42 C24 C1 -176.97(19) . . . . ? O42 C19 C29 C33 179.09(18) . . . . ? C8 C19 C29 C33 -1.1(3) . . . . ? C8 C12 C31 C33 -1.6(3) . . . . ? C8 C12 C31 N41 -179.06(19) . . . . ? C48 N41 C31 C33 162.59(17) . . . . ? C48 N41 C31 C12 -19.9(3) . . . . ? C12 C31 C33 C29 1.5(3) . . . . ? N41 C31 C33 C29 179.11(17) . . . . ? C19 C29 C33 C31 -0.1(3) . . . . ? C31 N41 C48 O50 -2.2(3) . . . . ? C31 N41 C48 C26 179.06(16) . . . . ? C21 O40 C10 C2 177.7(2) . . . . ? C21 C6 C16 C37 0.6(3) . . . . ? C10 O40 C21 C6 -179.17(19) . . . . ? C10 O40 C21 C23 0.7(3) . . . . ? C16 C6 C21 O40 179.72(18) . . . . ? C16 C6 C21 C23 -0.2(3) . . . . ? O40 C21 C23 C25 179.73(19) . . . . ? C6 C21 C23 C25 -0.4(3) . . . . ? C21 C23 C25 C37 0.6(3) . . . . ? C37 N44 C32 O51 -0.7(3) . . . . ? C37 N44 C32 C36 179.84(16) . . . . ? C23 C25 C37 C16 -0.2(3) . . . . ? C23 C25 C37 N44 178.16(18) . . . . ? C6 C16 C37 C25 -0.4(3) . . . . ? C6 C16 C37 N44 -178.61(17) . . . . ? C32 N44 C37 C25 162.30(18) . . . . ? C32 N44 C37 C16 -19.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.302 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 947748' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11291_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Phenacetin hydrobromide trihydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H33 Br2 N2 O7' _chemical_formula_weight 573.30 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8379(8) _cell_length_b 13.7200(16) _cell_length_c 14.2131(17) _cell_angle_alpha 76.208(2) _cell_angle_beta 77.572(2) _cell_angle_gamma 87.122(2) _cell_volume 1264.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3985 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.40 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 586 _exptl_absorpt_coefficient_mu 3.245 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.5354 _exptl_absorpt_correction_T_max 0.6418 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13797 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 26.71 _reflns_number_total 5297 _reflns_number_gt 4457 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0606P)^2^+0.3442P] 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 5297 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.002 _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 Br1 Br 0.27577(4) 0.554697(18) 0.931444(19) 0.02340(9) Uani 1 1 d . . . Br2 Br 1.17086(4) 0.451063(19) 0.60360(2) 0.02842(10) Uani 1 1 d . . . O27 O 0.9741(3) 0.55357(18) 0.78743(19) 0.0381(5) Uani 1 1 d . . . O26 O -0.0270(3) 0.15790(14) 0.93033(14) 0.0228(4) Uani 1 1 d . . . O25 O 0.6391(3) 0.04938(14) 1.20084(15) 0.0299(5) Uani 1 1 d . . . N24 N 0.5850(3) 0.20638(16) 1.11891(15) 0.0175(4) Uani 1 1 d . . . H24A H 0.6242 0.2692 1.1060 0.021 Uiso 1 1 calc R . . C23 C 0.4251(3) 0.19024(19) 1.07419(18) 0.0171(5) Uani 1 1 d . . . C22 C 0.6822(4) 0.14187(19) 1.17626(18) 0.0196(5) Uani 1 1 d . . . C21 C 0.1812(4) 0.26784(19) 0.97934(18) 0.0193(5) Uani 1 1 d . . . H21A H 0.1192 0.3266 0.9482 0.023 Uiso 1 1 calc R . . C20 C 0.2121(4) 0.0880(2) 1.02256(19) 0.0203(5) Uani 1 1 d . . . H20A H 0.1700 0.0237 1.0206 0.024 Uiso 1 1 calc R . . C19 C 0.3336(4) 0.27516(19) 1.02838(18) 0.0185(5) Uani 1 1 d . . . H19A H 0.3753 0.3395 1.0304 0.022 Uiso 1 1 calc R . . C18 C 0.1211(4) 0.17379(19) 0.97659(18) 0.0187(5) Uani 1 1 d . . . C17 C -0.1167(4) 0.2434(2) 0.87588(19) 0.0210(5) Uani 1 1 d . . . H17A H -0.0136 0.2835 0.8229 0.025 Uiso 1 1 calc R . . H17B H -0.1816 0.2866 0.9205 0.025 Uiso 1 1 calc R . . C16 C 0.3645(4) 0.0957(2) 1.07150(19) 0.0210(5) Uani 1 1 d . . . H16A H 0.4266 0.0370 1.1028 0.025 Uiso 1 1 calc R . . C15 C 0.8442(4) 0.1808(2) 1.21359(19) 0.0221(5) Uani 1 1 d . . . H15A H 0.9035 0.1249 1.2553 0.033 Uiso 1 1 calc R . . H15B H 0.7874 0.2294 1.2526 0.033 Uiso 1 1 calc R . . H15C H 0.9477 0.2136 1.1573 0.033 Uiso 1 1 calc R . . C14 C -0.2701(4) 0.2051(2) 0.8315(2) 0.0242(6) Uani 1 1 d . . . H14A H -0.3345 0.2620 0.7937 0.036 Uiso 1 1 calc R . . H14B H -0.3714 0.1657 0.8846 0.036 Uiso 1 1 calc R . . H14C H -0.2041 0.1627 0.7875 0.036 Uiso 1 1 calc R . . O13 O 0.4753(3) 0.15677(14) 0.42993(14) 0.0232(4) Uani 1 1 d . . . O12 O 1.1636(3) 0.05095(14) 0.68883(16) 0.0308(5) Uani 1 1 d . . . N11 N 1.0843(3) 0.20847(16) 0.61925(15) 0.0172(4) Uani 1 1 d . . . H11A H 1.1145 0.2720 0.6108 0.021 Uiso 1 1 calc R . . C10 C 1.1908(4) 0.1444(2) 0.67226(18) 0.0194(5) Uani 1 1 d . . . C9 C 0.6907(4) 0.26777(19) 0.47371(19) 0.0203(5) Uani 1 1 d . . . H9A H 0.6335 0.3263 0.4390 0.024 Uiso 1 1 calc R . . C8 C 0.8613(4) 0.0964(2) 0.57494(19) 0.0211(5) Uani 1 1 d . . . H8A H 0.9188 0.0379 0.6095 0.025 Uiso 1 1 calc R . . C7 C 0.7101(4) 0.0879(2) 0.52567(19) 0.0211(5) Uani 1 1 d . . . H7A H 0.6654 0.0233 0.5260 0.025 Uiso 1 1 calc R . . C6 C 0.9278(3) 0.19117(19) 0.57327(17) 0.0175(5) Uani 1 1 d . . . C5 C 0.6241(4) 0.17314(19) 0.47595(18) 0.0184(5) Uani 1 1 d . . . C4 C 0.8420(4) 0.2758(2) 0.52285(18) 0.0196(5) Uani 1 1 d . . . H4A H 0.8874 0.3404 0.5219 0.024 Uiso 1 1 calc R . . C3 C 0.2291(4) 0.2031(2) 0.3327(2) 0.0254(6) Uani 1 1 d . . . H3A H 0.1648 0.2599 0.2946 0.038 Uiso 1 1 calc R . . H3B H 0.1280 0.1645 0.3865 0.038 Uiso 1 1 calc R . . H3C H 0.2932 0.1599 0.2890 0.038 Uiso 1 1 calc R . . C2 C 0.3852(4) 0.2418(2) 0.37555(19) 0.0228(5) Uani 1 1 d . . . H2A H 0.4877 0.2814 0.3218 0.027 Uiso 1 1 calc R . . H2B H 0.3221 0.2855 0.4199 0.027 Uiso 1 1 calc R . . C1 C 1.3448(4) 0.1850(2) 0.71323(19) 0.0219(5) Uani 1 1 d . . . H1A H 1.4121 0.1293 0.7511 0.033 Uiso 1 1 calc R . . H1B H 1.2797 0.2281 0.7568 0.033 Uiso 1 1 calc R . . H1C H 1.4436 0.2243 0.6587 0.033 Uiso 1 1 calc R . . O29 O 0.6548(3) 0.46557(16) 0.81410(17) 0.0321(5) Uani 1 1 d . . . O30 O 0.6096(4) 0.4842(3) 0.6408(2) 0.0618(9) Uani 1 1 d . . . H29C H 0.783(6) 0.506(3) 0.804(3) 0.059(12) Uiso 1 1 d . . . H29B H 0.558(5) 0.490(2) 0.850(2) 0.030(9) Uiso 1 1 d . . . H30B H 0.693(6) 0.502(3) 0.591(3) 0.057(13) Uiso 1 1 d . . . H30A H 0.516(5) 0.474(3) 0.628(2) 0.031(10) Uiso 1 1 d . . . H27A H 1.045(6) 0.533(3) 0.738(3) 0.068(14) Uiso 1 1 d . . . H29A H 0.648(6) 0.477(3) 0.747(3) 0.063(13) Uiso 1 1 d . . . H27B H 1.029(6) 0.541(3) 0.841(3) 0.064(13) 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 Br1 0.02044(14) 0.01915(15) 0.03245(16) -0.00416(11) -0.01173(11) 0.00057(10) Br2 0.03523(17) 0.01963(16) 0.03335(17) -0.00134(11) -0.01838(13) -0.00238(11) O27 0.0314(11) 0.0497(15) 0.0409(13) -0.0159(11) -0.0194(11) 0.0047(10) O26 0.0217(9) 0.0203(10) 0.0299(10) -0.0034(8) -0.0161(8) 0.0006(7) O25 0.0341(11) 0.0177(10) 0.0423(12) 0.0008(8) -0.0266(9) 0.0012(8) N24 0.0172(10) 0.0166(11) 0.0187(10) -0.0021(8) -0.0061(8) 0.0005(8) C23 0.0158(11) 0.0184(13) 0.0169(11) -0.0027(10) -0.0053(9) 0.0019(9) C22 0.0168(11) 0.0225(14) 0.0194(12) -0.0038(10) -0.0060(10) 0.0039(10) C21 0.0193(12) 0.0179(13) 0.0200(12) -0.0004(10) -0.0083(10) 0.0033(10) C20 0.0219(12) 0.0186(13) 0.0229(13) -0.0054(10) -0.0094(10) 0.0011(10) C19 0.0195(12) 0.0174(13) 0.0195(12) -0.0031(10) -0.0073(10) 0.0000(10) C18 0.0154(11) 0.0234(14) 0.0177(12) -0.0036(10) -0.0055(9) -0.0001(10) C17 0.0181(12) 0.0241(14) 0.0225(13) -0.0039(11) -0.0104(10) 0.0041(10) C16 0.0227(12) 0.0181(13) 0.0219(13) -0.0019(10) -0.0085(10) 0.0060(10) C15 0.0172(12) 0.0285(15) 0.0221(13) -0.0036(11) -0.0105(10) 0.0014(10) C14 0.0216(13) 0.0283(15) 0.0250(13) -0.0055(11) -0.0113(11) 0.0026(11) O13 0.0230(9) 0.0205(10) 0.0292(10) -0.0023(8) -0.0161(8) 0.0009(7) O12 0.0350(11) 0.0197(10) 0.0433(12) -0.0010(9) -0.0276(10) 0.0023(8) N11 0.0188(10) 0.0144(11) 0.0191(10) -0.0016(8) -0.0080(8) 0.0014(8) C10 0.0176(12) 0.0232(14) 0.0173(12) -0.0034(10) -0.0056(10) 0.0025(10) C9 0.0212(12) 0.0187(13) 0.0215(13) -0.0015(10) -0.0099(10) 0.0039(10) C8 0.0232(12) 0.0172(13) 0.0232(13) -0.0016(10) -0.0095(10) 0.0039(10) C7 0.0220(12) 0.0183(13) 0.0251(13) -0.0041(10) -0.0103(10) 0.0005(10) C6 0.0158(11) 0.0214(13) 0.0156(11) -0.0035(10) -0.0057(9) 0.0023(9) C5 0.0161(11) 0.0239(14) 0.0160(12) -0.0040(10) -0.0064(9) 0.0016(10) C4 0.0214(12) 0.0178(13) 0.0203(12) -0.0027(10) -0.0081(10) 0.0003(10) C3 0.0215(13) 0.0321(16) 0.0244(13) -0.0052(12) -0.0106(11) 0.0009(11) C2 0.0197(12) 0.0279(15) 0.0210(13) -0.0019(11) -0.0100(10) 0.0031(10) C1 0.0189(12) 0.0266(14) 0.0219(13) -0.0042(11) -0.0107(10) 0.0036(10) O29 0.0287(11) 0.0359(12) 0.0357(12) -0.0117(10) -0.0129(10) 0.0060(9) O30 0.0265(13) 0.129(3) 0.0365(15) -0.0286(16) -0.0078(12) -0.0095(15) _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 O26 C18 1.373(3) . ? O26 C17 1.432(3) . ? O25 C22 1.265(3) . ? N24 C22 1.311(3) . ? N24 C23 1.427(3) . ? C23 C19 1.383(3) . ? C23 C16 1.393(4) . ? C22 C15 1.497(3) . ? C21 C18 1.385(4) . ? C21 C19 1.392(3) . ? C20 C18 1.391(4) . ? C20 C16 1.392(4) . ? C17 C14 1.507(3) . ? O13 C5 1.376(3) . ? O13 C2 1.429(3) . ? O12 C10 1.263(3) . ? N11 C10 1.314(3) . ? N11 C6 1.425(3) . ? C10 C1 1.496(3) . ? C9 C5 1.388(4) . ? C9 C4 1.389(3) . ? C8 C7 1.391(4) . ? C8 C6 1.392(4) . ? C7 C5 1.389(4) . ? C6 C4 1.387(4) . ? C3 C2 1.511(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 C18 O26 C17 118.35(19) . . ? C22 N24 C23 129.8(2) . . ? C19 C23 C16 119.7(2) . . ? C19 C23 N24 116.5(2) . . ? C16 C23 N24 123.8(2) . . ? O25 C22 N24 121.2(2) . . ? O25 C22 C15 120.6(2) . . ? N24 C22 C15 118.2(2) . . ? C18 C21 C19 119.2(2) . . ? C18 C20 C16 120.4(2) . . ? C23 C19 C21 121.1(2) . . ? O26 C18 C21 124.0(2) . . ? O26 C18 C20 115.8(2) . . ? C21 C18 C20 120.2(2) . . ? O26 C17 C14 107.5(2) . . ? C20 C16 C23 119.4(2) . . ? C5 O13 C2 118.3(2) . . ? C10 N11 C6 130.1(2) . . ? O12 C10 N11 121.2(2) . . ? O12 C10 C1 120.6(2) . . ? N11 C10 C1 118.2(2) . . ? C5 C9 C4 119.1(2) . . ? C7 C8 C6 119.5(2) . . ? C5 C7 C8 120.5(2) . . ? C4 C6 C8 119.6(2) . . ? C4 C6 N11 116.2(2) . . ? C8 C6 N11 124.2(2) . . ? O13 C5 C9 123.8(2) . . ? O13 C5 C7 116.0(2) . . ? C9 C5 C7 120.2(2) . . ? C6 C4 C9 121.1(2) . . ? O13 C2 C3 107.5(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.71 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.711 _refine_diff_density_min -0.779 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 947749'