#------------------------------------------------------------------------------ #$Date: 2014-01-12 11:04:44 +0000 (Sun, 12 Jan 2014) $ #$Revision: 92407 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238950.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2238950 loop_ _publ_author_name 'Seidel, Nadine' 'Seichter, Wilhelm' 'Weber, Edwin' _publ_section_title ; 5-Bromobenzene-1,3-dicarbonitrile ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1732 _journal_page_last o1733 _journal_paper_doi 10.1107/S1600536813028857 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C8 H3 Br N2' _chemical_formula_moiety 'C8 H3 Br N2' _chemical_formula_sum 'C8 H3 Br N2' _chemical_formula_weight 207.03 _chemical_name_systematic ; 5-Bromobenzene-1,3-dicarbonitrile ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 93.719(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 13.3019(4) _cell_length_b 15.7762(5) _cell_length_c 7.4265(2) _cell_measurement_reflns_used 7273 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 29.12 _cell_measurement_theta_min 2.58 _cell_volume 1555.19(8) _computing_cell_refinement 'SAINT-NT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT-NT (Bruker, 2007)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEXII CCD area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 16811 _diffrn_reflns_theta_full 29.15 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 1.53 _exptl_absorpt_coefficient_mu 5.213 _exptl_absorpt_correction_T_max 0.6805 _exptl_absorpt_correction_T_min 0.2026 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2007)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.603 _refine_diff_density_min -0.577 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 4198 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0308 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0289P)^2^+1.0903P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0718 _refine_ls_wR_factor_ref 0.0783 _reflns_number_gt 3436 _reflns_number_total 4198 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL Nase_1 in P2(1)/c CELL 0.71073 13.3019 15.7762 7.4265 90.000 93.719 90.000 ZERR 8.00 0.0004 0.0005 0.0002 0.000 0.002 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N Br UNIT 64 24 16 8 OMIT -3 58.3 L.S. 20 ACTA BOND $H FMAP 2 PLAN 5 SIZE 0.080 0.430 0.450 WPDB CONF WGHT 0.028900 1.090300 FVAR 0.093730 TEMP -100 MOLE 1 Br1 4 0.882696 0.402498 0.121473 11.000000 0.037970 = 0.029120 0.032470 -0.003010 0.003080 -0.013250 N1 3 0.842599 0.791840 0.289322 11.000000 0.035910 = 0.037180 0.094690 0.000660 0.003240 0.006960 N2 3 1.277712 0.566499 0.470641 11.000000 0.030900 = 0.029710 0.048320 -0.003200 -0.003550 0.006170 C1 1 0.945715 0.501498 0.216595 11.000000 0.031980 = 0.024350 0.023420 0.000270 0.004690 -0.008090 C2 1 1.045613 0.497660 0.281545 11.000000 0.031050 = 0.020860 0.023640 0.001240 0.004210 -0.001630 AFIX 43 H2 2 1.082331 0.446079 0.278736 11.000000 -1.200000 AFIX 0 C3 1 1.091022 0.571628 0.351333 11.000000 0.026210 = 0.023820 0.022930 0.001230 0.002920 -0.000780 C4 1 1.038782 0.647514 0.356647 11.000000 0.027000 = 0.022330 0.030390 -0.000920 0.002270 -0.002070 AFIX 43 H4 2 1.070330 0.697119 0.405915 11.000000 -1.200000 AFIX 0 C5 1 0.938869 0.649190 0.287925 11.000000 0.025320 = 0.026250 0.035010 0.001260 0.003920 0.000530 C6 1 0.891449 0.576490 0.216868 11.000000 0.022640 = 0.032200 0.032840 0.002240 0.002570 -0.003500 AFIX 43 H6 2 0.823377 0.578378 0.169665 11.000000 -1.200000 AFIX 0 C7 1 0.884201 0.728465 0.288435 11.000000 0.026320 = 0.031400 0.055440 0.000110 0.002430 0.000390 C8 1 1.195799 0.568693 0.417871 11.000000 0.029750 = 0.020040 0.031870 -0.001470 0.001620 0.001370 MOLE 2 Br1A 4 0.370700 0.099566 0.082173 11.000000 0.036070 = 0.033080 0.042930 -0.000270 0.001860 -0.014490 N1A 3 0.378978 0.495950 0.078172 11.000000 0.048200 = 0.038730 0.050570 0.006150 -0.000390 0.012420 N2A 3 0.782261 0.240247 0.386153 11.000000 0.029680 = 0.025870 0.039430 0.001090 -0.003940 0.001180 C1A 1 0.446337 0.198633 0.135225 11.000000 0.027490 = 0.026510 0.025600 -0.000740 0.005250 -0.005270 C2A 1 0.404018 0.277355 0.102509 11.000000 0.022210 = 0.036630 0.024420 0.001300 0.002170 -0.001490 AFIX 43 H2A 2 0.336367 0.282346 0.054273 11.000000 -1.200000 AFIX 0 C3A 1 0.462045 0.349706 0.141307 11.000000 0.028050 = 0.025380 0.023660 0.000690 0.001750 0.003950 C4A 1 0.561222 0.343545 0.212669 11.000000 0.028890 = 0.022600 0.023970 -0.000900 0.000510 0.000050 AFIX 43 H4A 2 0.600588 0.392870 0.238062 11.000000 -1.200000 AFIX 0 C5A 1 0.601099 0.262732 0.245798 11.000000 0.023260 = 0.025310 0.021230 -0.000110 0.001660 0.000560 C6A 1 0.544700 0.189625 0.207387 11.000000 0.026750 = 0.021780 0.026190 0.000390 0.005560 -0.000420 AFIX 43 H6A 2 0.572893 0.135034 0.230040 11.000000 -1.200000 AFIX 0 C7A 1 0.416740 0.432013 0.106802 11.000000 0.031630 = 0.033040 0.030230 0.001800 0.000350 0.003170 C8A 1 0.703122 0.251809 0.322960 11.000000 0.030800 = 0.019450 0.028190 0.000380 0.001310 0.000180 HKLF 4 END ; _[local]_cod_data_source_file zp2009.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2238950 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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity Br Br1 -0.117304(18) 0.402498(14) 0.12147(3) 0.03315(8) Uani d . 1 1 N N1 -0.15740(18) 0.79184(15) 0.2893(4) 0.0560(7) Uani d . 1 1 N N2 0.27771(15) 0.56650(13) 0.4706(3) 0.0366(5) Uani d . 1 1 C C1 -0.05428(17) 0.50150(13) 0.2166(3) 0.0265(4) Uani d . 1 1 C C2 0.04561(16) 0.49766(13) 0.2815(3) 0.0251(4) Uani d . 1 1 H H2 0.0823 0.4461 0.2787 0.030 Uiso calc R 1 1 C C3 0.09102(17) 0.57163(13) 0.3513(3) 0.0243(4) Uani d . 1 1 C C4 0.03878(16) 0.64751(13) 0.3566(3) 0.0266(4) Uani d . 1 1 H H4 0.0703 0.6971 0.4059 0.032 Uiso calc R 1 1 C C5 -0.06113(17) 0.64919(14) 0.2879(3) 0.0288(4) Uani d . 1 1 C C6 -0.10855(17) 0.57649(14) 0.2169(3) 0.0292(4) Uani d . 1 1 H H6 -0.1766 0.5784 0.1697 0.035 Uiso calc R 1 1 C C7 -0.11580(18) 0.72847(15) 0.2884(4) 0.0377(6) Uani d . 1 1 C C8 0.19580(17) 0.56869(13) 0.4179(3) 0.0272(4) Uani d . 1 1 Br Br1A 0.370700(19) 0.099566(15) 0.08217(4) 0.03739(8) Uani d . 1 1 N N1A 0.37898(18) 0.49595(14) 0.0782(3) 0.0460(6) Uani d . 1 1 N N2A 0.78226(14) 0.24025(12) 0.3862(3) 0.0319(4) Uani d . 1 1 C C1A 0.44634(16) 0.19863(13) 0.1352(3) 0.0264(4) Uani d . 1 1 C C2A 0.40402(17) 0.27736(14) 0.1025(3) 0.0277(4) Uani d . 1 1 H H2A 0.3364 0.2823 0.0543 0.033 Uiso calc R 1 1 C C3A 0.46205(16) 0.34971(13) 0.1413(3) 0.0257(4) Uani d . 1 1 C C4A 0.56122(16) 0.34354(13) 0.2127(3) 0.0252(4) Uani d . 1 1 H H4A 0.6006 0.3929 0.2381 0.030 Uiso calc R 1 1 C C5A 0.60110(15) 0.26273(13) 0.2458(3) 0.0233(4) Uani d . 1 1 C C6A 0.54470(16) 0.18963(12) 0.2074(3) 0.0247(4) Uani d . 1 1 H H6A 0.5729 0.1350 0.2300 0.030 Uiso calc R 1 1 C C7A 0.41674(18) 0.43201(15) 0.1068(3) 0.0317(5) Uani d . 1 1 C C8A 0.70312(17) 0.25181(12) 0.3230(3) 0.0262(4) Uani d . 1 1 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 0.03797(14) 0.02912(13) 0.03247(13) -0.01325(9) 0.00308(10) -0.00301(8) N1 0.0359(12) 0.0372(12) 0.095(2) 0.0070(10) 0.0032(13) 0.0007(13) N2 0.0309(10) 0.0297(10) 0.0483(13) 0.0062(8) -0.0035(9) -0.0032(9) C1 0.0320(11) 0.0244(10) 0.0234(10) -0.0081(8) 0.0047(8) 0.0003(7) C2 0.0310(11) 0.0209(9) 0.0236(10) -0.0016(8) 0.0042(8) 0.0012(7) C3 0.0262(10) 0.0238(9) 0.0229(10) -0.0008(8) 0.0029(8) 0.0012(7) C4 0.0270(11) 0.0223(10) 0.0304(11) -0.0021(8) 0.0023(9) -0.0009(8) C5 0.0253(11) 0.0262(10) 0.0350(12) 0.0005(8) 0.0039(9) 0.0013(8) C6 0.0226(10) 0.0322(11) 0.0328(11) -0.0035(9) 0.0026(9) 0.0022(9) C7 0.0263(12) 0.0314(12) 0.0554(16) 0.0004(10) 0.0024(11) 0.0001(11) C8 0.0297(11) 0.0200(9) 0.0319(11) 0.0014(8) 0.0016(9) -0.0015(8) Br1A 0.03607(14) 0.03308(13) 0.04293(15) -0.01449(9) 0.00186(10) -0.00027(9) N1A 0.0482(14) 0.0387(12) 0.0506(14) 0.0124(10) -0.0004(11) 0.0062(10) N2A 0.0297(10) 0.0259(9) 0.0394(11) 0.0012(8) -0.0039(9) 0.0011(8) C1A 0.0275(11) 0.0265(10) 0.0256(10) -0.0053(8) 0.0053(8) -0.0007(8) C2A 0.0222(10) 0.0366(12) 0.0244(10) -0.0015(9) 0.0022(8) 0.0013(8) C3A 0.0280(11) 0.0254(10) 0.0237(10) 0.0039(8) 0.0018(8) 0.0007(8) C4A 0.0289(11) 0.0226(10) 0.0240(10) 0.0000(8) 0.0005(8) -0.0009(8) C5A 0.0233(10) 0.0253(10) 0.0212(10) 0.0006(8) 0.0017(8) -0.0001(7) C6A 0.0268(10) 0.0218(9) 0.0262(10) -0.0004(8) 0.0056(8) 0.0004(7) C7A 0.0316(12) 0.0330(12) 0.0302(11) 0.0032(10) 0.0003(9) 0.0018(9) C8A 0.0308(11) 0.0194(9) 0.0282(11) 0.0002(8) 0.0013(9) 0.0004(7) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 121.65(19) C2 C1 Br1 119.13(16) C6 C1 Br1 119.21(17) C1 C2 C3 118.31(19) C1 C2 H2 120.8 C3 C2 H2 120.8 C4 C3 C2 121.7(2) C4 C3 C8 119.39(19) C2 C3 C8 118.86(19) C3 C4 C5 118.3(2) C3 C4 H4 120.8 C5 C4 H4 120.8 C4 C5 C6 121.3(2) C4 C5 C7 118.9(2) C6 C5 C7 119.8(2) C1 C6 C5 118.6(2) C1 C6 H6 120.7 C5 C6 H6 120.7 N1 C7 C5 178.8(3) N2 C8 C3 179.7(3) C2A C1A C6A 121.60(19) C2A C1A Br1A 120.23(16) C6A C1A Br1A 118.18(15) C1A C2A C3A 119.1(2) C1A C2A H2A 120.5 C3A C2A H2A 120.5 C4A C3A C2A 121.22(19) C4A C3A C7A 120.2(2) C2A C3A C7A 118.6(2) C3A C4A C5A 118.05(19) C3A C4A H4A 121.0 C5A C4A H4A 121.0 C6A C5A C4A 121.71(19) C6A C5A C8A 117.39(18) C4A C5A C8A 120.90(18) C1A C6A C5A 118.36(19) C1A C6A H6A 120.8 C5A C6A H6A 120.8 N1A C7A C3A 178.4(3) N2A C8A C5A 177.3(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1 1.888(2) N1 C7 1.143(3) N2 C8 1.134(3) C1 C2 1.385(3) C1 C6 1.386(3) C2 C3 1.398(3) C2 H2 0.9500 C3 C4 1.386(3) C3 C8 1.449(3) C4 C5 1.393(3) C4 H4 0.9500 C5 C6 1.396(3) C5 C7 1.447(3) C6 H6 0.9500 Br1A C1A 1.886(2) N1A C7A 1.141(3) N2A C8A 1.139(3) C1A C2A 1.379(3) C1A C6A 1.389(3) C2A C3A 1.397(3) C2A H2A 0.9500 C3A C4A 1.393(3) C3A C7A 1.447(3) C4A C5A 1.397(3) C4A H4A 0.9500 C5A C6A 1.395(3) C5A C8A 1.449(3) C6A H6A 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C4A H4A N2 3_666 0.95 2.69 3.388(3) 130 C4 H4 N2A 3_666 0.95 2.61 3.444(3) 147 C6A H6A N1A 2_645 0.95 2.67 3.563(3) 157 C2 H2 N1 2_545 0.95 2.69 3.624(3) 168 C2A H2A N1 2_545 0.95 2.72 3.435(3) 133 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 C6 C1 C2 C3 1.1(3) Br1 C1 C2 C3 179.95(15) C1 C2 C3 C4 0.0(3) C1 C2 C3 C8 -179.33(19) C2 C3 C4 C5 -0.8(3) C8 C3 C4 C5 178.5(2) C3 C4 C5 C6 0.7(3) C3 C4 C5 C7 -178.5(2) C2 C1 C6 C5 -1.3(3) Br1 C1 C6 C5 179.87(17) C4 C5 C6 C1 0.4(3) C7 C5 C6 C1 179.5(2) C6A C1A C2A C3A 0.7(3) Br1A C1A C2A C3A -179.35(16) C1A C2A C3A C4A -0.2(3) C1A C2A C3A C7A -179.9(2) C2A C3A C4A C5A -0.5(3) C7A C3A C4A C5A 179.2(2) C3A C4A C5A C6A 0.7(3) C3A C4A C5A C8A -178.87(19) C2A C1A C6A C5A -0.4(3) Br1A C1A C6A C5A 179.62(15) C4A C5A C6A C1A -0.3(3) C8A C5A C6A C1A 179.29(19)