data_2203258 loop_ _publ_author_name '\'Ismail \,Celik' 'Osman \,Cakmak' 'Mehmet Akkurt' 'Cem C\"uneyt Ersanl\?i' 'Orhan B\"uy\"ukg\"ung\"or' _publ_section_title ; 2,3,-exo,exo-5,6-tetrabromo-bicyclo[2.2.1]hept-2-ene ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o468 _journal_page_last o470 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac ? _chemical_formula_moiety 'C7 H6 Br4' _chemical_formula_structural ? _chemical_formula_sum 'C7 H6 Br4' _chemical_formula_weight 409.72 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ; 2,3,-exo,exo-5,6-tetrabromo-bicyclo[2.2.1]hept-2-ene ; _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_space_group_name_H-M 'P n m a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.681(5) _cell_length_b 12.040(5) _cell_length_c 12.326(5) _cell_measurement_reflns_used 1296 _cell_measurement_temperature 293 _cell_measurement_theta_max 29.47 _cell_measurement_theta_min 2.36 _cell_volume 991.5(9) _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEPIII (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al. 1999)' _diffrn_ambient_temperature 293 _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.924 _diffrn_measured_fraction_theta_max 0.924 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS2' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.153 _diffrn_reflns_av_sigmaI/netI 0.0829 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 16499 _diffrn_reflns_reduction_process ' ?' _diffrn_reflns_theta_full 29.47 _diffrn_reflns_theta_max 29.47 _diffrn_reflns_theta_min 2.36 _diffrn_standards_decay_% negligible _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 16.171 _exptl_absorpt_correction_T_max 0.198 _exptl_absorpt_correction_T_min 0.057 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Cubic fit to sin(theta)/lambda - 24 parameters (Parkin et al., 1995) ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.745 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _refine_diff_density_max 0.826 _refine_diff_density_min -0.597 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_extinction_coef 0.0015(3) _refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints ? _refine_ls_number_parameters 53 _refine_ls_number_reflns 1330 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.005 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0477 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+0.4407P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.0915 _reflns_number_gt 813 _reflns_number_total 1330 _reflns_threshold_expression I>2\s(I) loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,1/2-z -x,1/2+y,-z -x,-y,-z 1/2+x,y,1/2-z 1/2-x,1/2+y,1/2+z x,1/2-y,z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0594(4) 0.0383(3) 0.0629(4) -0.0051(3) 0.0161(3) 0.0005(3) Br2 0.0622(4) 0.0719(5) 0.0545(4) 0.0198(4) 0.0121(3) -0.0052(3) C1 0.040(3) 0.041(3) 0.034(3) -0.003(2) 0.003(2) -0.003(2) C2 0.044(3) 0.042(3) 0.048(3) 0.005(3) -0.003(3) 0.002(3) C3 0.044(3) 0.052(3) 0.039(3) 0.008(2) 0.003(3) -0.005(2) C4 0.050(5) 0.055(5) 0.052(5) 0.0000 -0.007(4) 0.0000 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Br1 0.37445(11) 0.11473(5) 0.60301(5) 0.0535(2) Uani . . 1.000 Br Br2 1.00100(11) 0.10403(6) 0.32581(5) 0.0629(3) Uani . . 1.000 Br C1 0.5578(8) 0.1861(4) 0.5005(4) 0.0383(17) Uani . . 1.000 C C2 0.7751(9) 0.1593(5) 0.5310(5) 0.0447(17) Uani . . 1.000 C C3 0.8990(9) 0.1973(5) 0.4329(5) 0.0450(17) Uani . . 1.000 C C4 0.8242(14) 0.25000 0.6135(7) 0.052(3) Uani . . 1.000 C H1 0.53030 0.15900 0.42700 0.0460 Uiso calc R 1.000 H H2 0.79960 0.08300 0.55530 0.0540 Uiso calc R 1.000 H H4A 0.96330 0.25000 0.63620 0.0630 Uiso calc R 1.000 H H4B 0.73590 0.25000 0.67600 0.0630 Uiso calc R 1.000 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Br -0.2901 2.4595 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Br1 C1 C2 . . . 110.0(4) yes Br1 C1 C1 . . 8_555 116.0(3) yes C1 C1 C2 8_555 . . 102.1(4) yes C1 C2 C3 . . . 104.8(5) yes C1 C2 C4 . . . 102.5(5) yes C3 C2 C4 . . . 101.3(5) yes Br2 C3 C2 . . . 125.2(4) yes Br2 C3 C3 . . 8_555 127.1(5) yes C2 C3 C3 . . 8_555 107.3(5) no C2 C4 C2 . . 8_555 91.3(6) yes Br1 C1 H1 . . . 109.45 no C2 C1 H1 . . . 109.50 no C1 C1 H1 8_555 . . 109.44 no C1 C2 H2 . . . 115.48 no C3 C2 H2 . . . 115.47 no C4 C2 H2 . . . 115.51 no C2 C4 H4A . . . 113.42 no C2 C4 H4B . . . 113.45 no H4A C4 H4B . . . 110.69 no C2 C4 H4A 8_555 . . 113.42 no C2 C4 H4B 8_555 . . 113.45 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C1 . . 1.958(5) yes Br2 C3 . . 1.862(6) yes C1 C2 . . 1.534(8) yes C1 C1 . 8_555 1.539(7) yes C2 C3 . . 1.535(9) yes C2 C4 . . 1.528(9) yes C3 C3 . 8_555 1.269(9) yes C1 H1 . . 0.9803 no C2 H2 . . 0.9800 no C4 H4A . . 0.9705 no C4 H4B . . 0.9703 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br1 Br2 3.742(3) . 5_656 no Br1 Br1 3.257(3) . 8_555 no Br1 Br2 3.895(3) . 2_655 no Br2 Br1 3.742(3) . 5_656 no Br2 Br2 3.828(3) . 6_555 no Br2 Br2 3.515(3) . 8_555 no Br2 Br1 3.895(3) . 2_654 no Br2 Br2 3.828(3) . 6_455 no Br1 H4B 3.0485 . . no Br1 H4A 3.2195 . 1_455 no Br1 H4A 3.2195 . 8_455 no Br2 H2 2.9988 . 5_756 no Br2 H1 3.1917 . 6_555 no C3 H1 3.0111 . 8_555 no H1 Br2 3.1917 . 6_455 no H1 C3 3.0111 . 8_555 no H2 Br2 2.9988 . 5_756 no H4A Br1 3.2195 . 1_655 no H4A Br1 3.2195 . 8_655 no H4B Br1 3.0485 . . no H4B Br1 3.0485 . 8_555 no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br1 C1 C2 C3 . . . . 168.1(4) yes Br1 C1 C2 C4 . . . . -86.6(5) yes C1 C1 C2 C3 8_555 . . . -68.2(5) no C1 C1 C2 C4 8_555 . . . 37.2(5) no Br1 C1 C1 Br1 . . 8_555 8_555 0.0(5) no Br1 C1 C1 C2 . . 8_555 8_555 119.6(4) yes C2 C1 C1 Br1 . . 8_555 8_555 -119.6(4) no C2 C1 C1 C2 . . 8_555 8_555 0.0(5) no C1 C2 C3 Br2 . . . . -101.2(5) yes C1 C2 C3 C3 . . . 8_555 71.9(6) no C4 C2 C3 Br2 . . . . 152.6(5) yes C4 C2 C3 C3 . . . 8_555 -34.3(7) no C1 C2 C4 C2 . . . 8_555 -57.7(6) no C3 C2 C4 C2 . . . 8_555 50.3(6) no Br2 C3 C3 Br2 . . 8_555 8_555 0.0(9) no Br2 C3 C3 C2 . . 8_555 8_555 172.9(4) yes C2 C3 C3 Br2 . . 8_555 8_555 -172.9(4) no C2 C3 C3 C2 . . 8_555 8_555 0.0(7) no