Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Peter G. Jones' 'Fabiola Vancea' _publ_contact_author_name 'Dr Peter G Jones' _publ_contact_author_address ; Institut fur Anorganische und Analytische Chemie der Technischen Universitat Braunschweig Postfach 3329 Braunschweig 38023 GERMANY ; _publ_contact_author_email P.JONES@TU-BS.DE _publ_section_title ; Unexpected isostructurality by permutation of classical and "weak" hydrogen bonds ; data_pic3br _database_code_CSD 213993 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H7 Br2 N' _chemical_formula_weight 252.95 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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.9431(6) _cell_length_b 13.2946(8) _cell_length_c 7.6992(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.125(4) _cell_angle_gamma 90.00 _cell_volume 788.46(9) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 4583 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.5 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 10.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.292 _exptl_absorpt_correction_T_max 0.494 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 SMART 1000 CCD' _diffrn_measurement_method '\w- and \f-scan' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15950 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2308 _reflns_number_gt 2071 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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 'Siemens XP' _computing_publication_material SHELXL-97 _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^)+(0.0269P)^2^+0.2236P] 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 'NH free, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2308 _refine_ls_number_parameters 86 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0488 _refine_ls_wR_factor_gt 0.0480 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 1.17399(2) 0.391939(15) 0.62374(2) 0.02326(6) Uani 1 1 d . . . Br2 Br 0.68386(2) 0.580047(14) 0.78336(2) 0.02107(6) Uani 1 1 d . . . N1 N 0.5932(2) 0.28211(13) 0.4735(2) 0.0217(3) Uani 1 1 d . . . H0 H 0.519(4) 0.307(2) 0.405(4) 0.040(8) Uiso 1 1 d . . . C2 C 0.7211(2) 0.34082(15) 0.5659(2) 0.0213(4) Uani 1 1 d . . . H2 H 0.7104 0.4120 0.5585 0.026 Uiso 1 1 calc R . . C3 C 0.8689(2) 0.29725(14) 0.6722(2) 0.0187(3) Uani 1 1 d . . . C4 C 0.8788(2) 0.19274(15) 0.6786(2) 0.0216(4) Uani 1 1 d . . . H4 H 0.9794 0.1609 0.7493 0.026 Uiso 1 1 calc R . . C5 C 0.7429(3) 0.13506(16) 0.5825(2) 0.0244(4) Uani 1 1 d . . . H5 H 0.7487 0.0637 0.5886 0.029 Uiso 1 1 calc R . . C6 C 0.5991(2) 0.18209(16) 0.4780(2) 0.0235(4) Uani 1 1 d . . . H6 H 0.5052 0.1436 0.4098 0.028 Uiso 1 1 calc R . . C7 C 1.0117(3) 0.36263(19) 0.7741(3) 0.0300(5) Uani 1 1 d . . . H7A H 1.0739 0.3281 0.8852 0.036 Uiso 1 1 calc R . . H7B H 0.9630 0.4262 0.8079 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01809(9) 0.02685(11) 0.02411(10) -0.00028(7) 0.00373(7) -0.00468(7) Br2 0.01900(9) 0.02271(10) 0.02043(9) 0.00124(6) 0.00274(7) 0.00302(6) N1 0.0150(7) 0.0308(9) 0.0180(7) 0.0044(6) 0.0017(6) 0.0041(6) C2 0.0243(9) 0.0189(9) 0.0211(8) 0.0007(6) 0.0065(7) 0.0024(7) C3 0.0161(8) 0.0262(9) 0.0142(7) -0.0025(6) 0.0043(6) -0.0028(7) C4 0.0188(8) 0.0283(10) 0.0165(8) 0.0031(7) 0.0016(7) 0.0067(7) C5 0.0323(11) 0.0189(9) 0.0228(9) 0.0011(7) 0.0081(8) -0.0004(7) C6 0.0202(9) 0.0315(10) 0.0189(8) -0.0014(7) 0.0048(7) -0.0083(7) C7 0.0239(10) 0.0454(13) 0.0215(9) -0.0105(8) 0.0072(8) -0.0128(9) _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 C7 1.970(2) . ? N1 C6 1.331(3) . ? N1 C2 1.340(3) . ? C2 C3 1.384(3) . ? C3 C4 1.392(3) . ? C3 C7 1.491(3) . ? C4 C5 1.382(3) . ? C5 C6 1.377(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 123.44(17) . . ? N1 C2 C3 119.63(18) . . ? C2 C3 C4 118.10(17) . . ? C2 C3 C7 119.60(18) . . ? C4 C3 C7 122.29(18) . . ? C5 C4 C3 120.34(17) . . ? C6 C5 C4 119.28(19) . . ? N1 C6 C5 119.20(18) . . ? C3 C7 Br1 109.19(12) . . ? 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 C6 N1 C2 C3 0.2(3) . . . . ? N1 C2 C3 C4 0.1(3) . . . . ? N1 C2 C3 C7 179.61(16) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C7 C3 C4 C5 179.70(17) . . . . ? C3 C4 C5 C6 1.2(3) . . . . ? C2 N1 C6 C5 0.1(3) . . . . ? C4 C5 C6 N1 -0.8(3) . . . . ? C2 C3 C7 Br1 -89.28(19) . . . . ? C4 C3 C7 Br1 90.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H0 Br2 0.76(3) 2.41(3) 3.1602(17) 168(3) 3_666 C2 H2 Br2 0.95 2.87 3.6397(19) 139.4 . C4 H4 Br2 0.95 2.95 3.7285(19) 140.1 2_746 C5 H5 Br2 0.95 2.97 3.630(2) 127.3 4_565 C7 H7B Br2 0.99 2.99 3.903(2) 154.0 . C4 H4 Br1 0.95 3.00 3.8197(17) 144.9 4_566 C6 H6 Br1 0.95 3.03 3.9131(19) 155.7 4_465 C5 H5 Br1 0.95 3.14 3.907(2) 139.5 2_746 C7 H7A Br2 0.99 3.05 3.744(2) 128.1 3_767 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.526 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.090