Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Gautam R. Desiraju' 'Roland Boese' 'Archan Dey' 'Ram K. R. Jetti' _publ_contact_author_name 'Prof Gautam R. Desiraju' _publ_contact_author_address ; School of Chemistry University of Hyderabad PO Central University Hyderabad 500046 INDIA ; _publ_contact_author_email DESIRAJU@UOHYD.ERNET.IN _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Supramolecular equivalence of halogen, ethynyl and hydroxy groups. A comparison of the crystal structures of some 4-substituted anilines. ; data_aebdju2a _database_code_CSD 209451 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-ethynylaniline ; _chemical_name_common 4-ethynylaniline _chemical_melting_point 373K _chemical_formula_moiety 'C8 H7 N' _chemical_formula_sum 'C8 H7 N' _chemical_formula_weight 117.15 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 10.423(4) _cell_length_b 7.033(3) _cell_length_c 8.951(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 656.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.83 _exptl_crystal_size_mid 0.67 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.942 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details ; Siemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Siemens SMART CCD area detector system' _diffrn_measurement_method ; Full sphere data collection in omega at 0.3 deg scan width, two runs with 720 frames, phi = 0, 270(deg) two runs with 436 frames, phi = 88, 180 deg) ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4811 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 28.53 _reflns_number_total 866 _reflns_number_gt 753 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART Vers. 5.054 1997/98' _computing_cell_refinement ; BRUKER AXS SAINT program Vers.6.01 ; _computing_data_reduction ; BRUKER AXS SAINT program Vers.6.01 ; _computing_structure_solution ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_structure_refinement ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_molecular_graphics ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_publication_material ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _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^)+(0.1077P)^2^+0.0773P] 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 866 _refine_ls_number_parameters 49 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1528 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 N1 N 0.00608(16) 0.2500 1.2045(2) 0.0647(6) Uani 1 2 d S . . H1A H -0.0222 0.1341 1.2398 0.078 Uiso 1 1 d R . . C1 C 0.55591(15) 0.2500 0.78606(18) 0.0427(4) Uani 1 2 d S . . H1 H 0.6384 0.2500 0.7278 0.051 Uiso 1 2 d SR . . C2 C 0.45854(13) 0.2500 0.85818(16) 0.0360(4) Uani 1 2 d S . . C3 C 0.34198(13) 0.2500 0.94375(15) 0.0343(4) Uani 1 2 d S . . C4 C 0.28385(10) 0.07790(15) 0.98724(12) 0.0388(4) Uani 1 1 d . . . H4 H 0.3224 -0.0540 0.9476 0.047 Uiso 1 1 d R . . C5 C 0.17252(11) 0.07796(15) 1.07226(13) 0.0437(4) Uani 1 1 d . . . H5 H 0.1357 -0.0507 1.1057 0.052 Uiso 1 1 d R . . C6 C 0.11574(15) 0.2500 1.11814(17) 0.0423(4) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0693(11) 0.0549(9) 0.0698(11) 0.000 0.0362(9) 0.000 C1 0.0381(8) 0.0490(9) 0.0409(8) 0.000 -0.0001(6) 0.000 C2 0.0374(8) 0.0376(7) 0.0329(7) 0.000 -0.0065(5) 0.000 C3 0.0362(7) 0.0381(7) 0.0287(7) 0.000 -0.0045(5) 0.000 C4 0.0458(7) 0.0348(6) 0.0358(6) 0.0049(3) 0.0005(4) 0.0049(3) C5 0.0528(7) 0.0373(6) 0.0411(6) 0.0074(4) 0.0070(5) -0.0001(4) C6 0.0470(9) 0.0455(8) 0.0346(8) 0.000 0.0062(6) 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 N1 C6 1.380(2) . ? C1 C2 1.203(2) . ? C2 C3 1.436(2) . ? C3 C4 1.4085(13) . ? C3 C4 1.4085(13) 7_565 ? C4 C5 1.3876(16) . ? C5 C6 1.4082(15) . ? C6 C5 1.4082(15) 7_565 ? 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 C1 C2 C3 179.77(14) . . ? C4 C3 C4 118.50(13) . 7_565 ? C4 C3 C2 120.75(7) . . ? C4 C3 C2 120.75(7) 7_565 . ? C5 C4 C3 120.73(10) . . ? C4 C5 C6 120.77(10) . . ? N1 C6 C5 120.76(7) . . ? N1 C6 C5 120.76(7) . 7_565 ? C5 C6 C5 118.47(14) . 7_565 ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 28.53 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.279 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.054 #END# data_babdju0a _database_code_CSD 209452 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-bromoaniline ; _chemical_name_common 4-bromoaniline _chemical_melting_point 337K _chemical_formula_moiety 'C6 H5 Br N' _chemical_formula_sum 'C6 H5 Br N' _chemical_formula_weight 171.01 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 8.594(2) _cell_length_b 7.6166(19) _cell_length_c 9.469(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 619.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 2537 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 26.76 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 6.513 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.407 _exptl_absorpt_correction_T_max 0.594 _exptl_absorpt_process_details ; Siemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 203(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 'Siemens SMART CCD area detector system' _diffrn_measurement_method ; Full sphere data collection in omega at 0.3 deg scan width, two runs with 720 frames, phi = 0, 270(deg) two runs with 436 frames, phi = 88, 180 deg) ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4777 _diffrn_reflns_av_R_equivalents 0.1079 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 28.42 _reflns_number_total 837 _reflns_number_gt 656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART Vers. 5.054 1997/98' _computing_cell_refinement ; BRUKER AXS SAINT program Vers.6.01 ; _computing_data_reduction ; BRUKER AXS SAINT program Vers.6.01 ; _computing_structure_solution ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_structure_refinement ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_molecular_graphics ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_publication_material ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _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^)+(0.0548P)^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 837 _refine_ls_number_parameters 43 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 0.46228(6) 0.2500 0.70711(5) 0.0335(2) Uani 1 2 d S . . N1 N 1.0055(8) 0.2500 0.2948(5) 0.0535(15) Uani 1 2 d S . . H1 H 1.0556 0.1477 0.2845 0.064 Uiso 0.50 1 d PR . . C1 C 0.8836(6) 0.2500 0.3923(5) 0.0349(11) Uani 1 2 d S . . C2 C 0.8173(4) 0.0929(5) 0.4404(3) 0.0341(8) Uani 1 1 d . . . H2 H 0.8600 -0.0197 0.4082 0.041 Uiso 1 1 d R . . C3 C 0.6947(4) 0.0932(4) 0.5347(3) 0.0308(7) Uani 1 1 d . . . H3 H 0.6567 -0.0001 0.5593 0.037 Uiso 1 1 d R . . C4 C 0.6339(5) 0.2500 0.5808(4) 0.0263(9) Uani 1 2 d S . . 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 0.0346(3) 0.0364(3) 0.0293(3) 0.000 0.00572(19) 0.000 N1 0.056(3) 0.052(4) 0.052(3) 0.000 0.025(2) 0.000 C1 0.035(3) 0.042(3) 0.027(2) 0.000 0.005(2) 0.000 C2 0.0356(18) 0.0347(18) 0.0320(16) -0.0058(14) -0.0013(16) 0.0037(15) C3 0.0341(17) 0.0285(16) 0.0298(15) 0.0001(13) -0.0041(15) -0.0053(14) C4 0.026(2) 0.032(2) 0.0211(19) 0.000 -0.0020(17) 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 Br1 C4 1.899(4) . ? N1 C1 1.396(7) . ? C1 C2 1.401(4) . ? C1 C2 1.401(4) 7_565 ? C2 C3 1.381(5) . ? C3 C4 1.375(4) . ? C4 C3 1.375(4) 7_565 ? 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 N1 C1 C2 121.3(2) . . ? N1 C1 C2 121.3(2) . 7_565 ? C2 C1 C2 117.3(4) . 7_565 ? C3 C2 C1 121.2(3) . . ? C4 C3 C2 119.8(3) . . ? C3 C4 C3 120.6(4) 7_565 . ? C3 C4 Br1 119.7(2) 7_565 . ? C3 C4 Br1 119.7(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.834 _refine_diff_density_min -1.196 _refine_diff_density_rms 0.144 #END# data_aibdju0m _database_code_CSD 209453 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-iodoaniline ; _chemical_name_common 4-iodoaniline _chemical_melting_point 364K _chemical_formula_moiety 'C6 H6 I N' _chemical_formula_sum 'C6 H6 I N' _chemical_formula_weight 219.02 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.422(7) _cell_length_b 4.965(4) _cell_length_c 8.645(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.790(13) _cell_angle_gamma 90.00 _cell_volume 340.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 3102 _cell_measurement_theta_min 5.01 _cell_measurement_theta_max 57.26 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 4.599 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.326 _exptl_absorpt_correction_T_max 0.550 _exptl_absorpt_process_details ; Siemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 'Siemens SMART CCD area detector system' _diffrn_measurement_method ; Full sphere data collection in omega at 0.3 deg scan width, two runs with 720 frames, phi = 0, 270(deg) two runs with 436 frames, phi = 88, 180 deg) ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2964 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0514 _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 -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.63 _reflns_number_total 1630 _reflns_number_gt 1463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART Vers. 5.054 1997/98' _computing_cell_refinement ; BRUKER AXS SAINT program Vers.6.01 ; _computing_data_reduction ; BRUKER AXS SAINT program Vers.6.01 ; _computing_structure_solution ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_structure_refinement ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_molecular_graphics ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _computing_publication_material ; BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME ; _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^)+(0.0579P)^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 0.13(6) _refine_ls_number_reflns 1630 _refine_ls_number_parameters 73 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 I1 I 0.81402(3) 0.0133(3) 0.37331(3) 0.05116(16) Uani 1 1 d . . . N1 N 0.0588(6) 0.3909(10) 0.1151(6) 0.0442(10) Uani 1 1 d . . . H1A H 0.0066 0.3868 0.1924 0.053 Uiso 1 1 d R . . H1B H 0.0413 0.4983 0.0610 0.053 Uiso 1 1 d R . . C1 C 0.2277(7) 0.3105(10) 0.1722(6) 0.0372(9) Uani 1 1 d . . . C2 C 0.2794(7) 0.0931(11) 0.2786(6) 0.0427(11) Uani 1 1 d . . . H2 H 0.1997 0.0043 0.3147 0.051 Uiso 1 1 d R . . C3 C 0.4447(6) 0.0040(17) 0.3338(5) 0.0390(9) Uani 1 1 d . . . H3 H 0.4771 -0.1440 0.4054 0.047 Uiso 1 1 d R . . C4 C 0.5620(6) 0.1381(11) 0.2809(6) 0.0376(10) Uani 1 1 d . . . C5 C 0.5125(8) 0.3490(12) 0.1724(7) 0.0436(11) Uani 1 1 d . . . H5 H 0.5921 0.4354 0.1351 0.052 Uiso 1 1 d R . . C6 C 0.3465(9) 0.4351(11) 0.1179(7) 0.0463(14) Uani 1 1 d . . . H6 H 0.3140 0.5796 0.0435 0.056 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03268(19) 0.0683(3) 0.0489(2) 0.0031(3) 0.00915(12) 0.0027(2) N1 0.036(2) 0.045(2) 0.046(2) 0.005(2) 0.0068(19) 0.0046(19) C1 0.037(2) 0.037(2) 0.033(2) -0.0071(19) 0.0064(18) 0.000(2) C2 0.039(2) 0.046(3) 0.041(2) 0.0021(18) 0.0122(19) -0.0010(18) C3 0.0407(19) 0.038(2) 0.0361(17) 0.003(4) 0.0103(14) 0.010(4) C4 0.035(2) 0.040(2) 0.036(2) -0.0073(18) 0.0098(18) -0.0034(19) C5 0.050(3) 0.043(3) 0.043(2) -0.002(2) 0.023(2) -0.008(2) C6 0.060(4) 0.040(3) 0.036(2) -0.0001(17) 0.013(2) -0.001(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 I1 C4 2.093(5) . ? N1 C1 1.397(7) . ? C1 C6 1.386(8) . ? C1 C2 1.389(7) . ? C2 C3 1.383(7) . ? C3 C4 1.390(8) . ? C4 C5 1.373(8) . ? C5 C6 1.384(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.1(5) . . ? C6 C1 N1 121.2(5) . . ? C2 C1 N1 120.6(5) . . ? C3 C2 C1 122.0(6) . . ? C2 C3 C4 118.5(6) . . ? C5 C4 C3 120.3(5) . . ? C5 C4 I1 121.4(4) . . ? C3 C4 I1 118.3(4) . . ? C4 C5 C6 120.4(5) . . ? C5 C6 C1 120.6(5) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.63 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.240 _refine_diff_density_min -1.074 _refine_diff_density_rms 0.148 #END#