#------------------------------------------------------------------------------ #$Date: 2024-05-05 05:16:01 +0300 (Sun, 05 May 2024) $ #$Revision: 291595 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248367.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7248367 loop_ _publ_author_name 'Kupietz, Kamil' 'Gomila, Rosa M.' 'Roisnel, Thierry' 'Frontera, Antonio' 'Gramage-Doria, Rafael' _publ_section_title ; Shortening CN⋯Br--Csp3 halogen bonds via \p-stacking ; _journal_issue 16 _journal_name_full CrystEngComm _journal_page_first 2131 _journal_page_last 2135 _journal_paper_doi 10.1039/D4CE00307A _journal_volume 26 _journal_year 2024 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C8 H5 Br2 N' _chemical_formula_sum 'C8 H5 Br2 N' _chemical_formula_weight 274.95 _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_Hall '-P 2ac 2n' _space_group_name_H-M_alt 'P n m a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_update_record ; 2024-02-01 deposited with the CCDC. 2024-04-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.7185(18) _cell_length_b 7.2021(9) _cell_length_c 8.8003(12) _cell_measurement_reflns_used 4083 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.4537 _cell_measurement_theta_min 2.7498 _cell_measurement_wavelength 0.710730 _cell_volume 869.5(2) _computing_cell_refinement 'APEX3 (Bruker, 2015)' _computing_data_collection 'Bruker APEX3 (Bruker, 2015)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics ; 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)' ; _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2023)' _computing_structure_refinement 'SHELXL-2019_2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018_2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_detector CMOS-PHOTON70 _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_orient_matrix_UB_11 -0.0149689 _diffrn_orient_matrix_UB_12 0.0783379 _diffrn_orient_matrix_UB_13 -0.0522151 _diffrn_orient_matrix_UB_21 0.0423291 _diffrn_orient_matrix_UB_22 0.0805342 _diffrn_orient_matrix_UB_23 0.0463761 _diffrn_orient_matrix_UB_31 0.1313886 _diffrn_orient_matrix_UB_32 -0.0170205 _diffrn_orient_matrix_UB_33 -0.0208897 _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7270 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.468 _diffrn_reflns_theta_min 2.750 _diffrn_source_current 1.00 _diffrn_source_power 50.0 _diffrn_source_voltage 50.00 _exptl_absorpt_coefficient_mu 9.254 _exptl_absorpt_correction_T_max 0.435 _exptl_absorpt_correction_T_min 0.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.100 _exptl_crystal_description prism _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.170 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.090 _refine_diff_density_max 0.721 _refine_diff_density_min -0.604 _refine_diff_density_rms 0.073 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 64 _refine_ls_number_reflns 1074 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0238 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0155P)^2^+1.6587P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.0563 _reflns_number_gt 883 _reflns_number_total 1074 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d4ce00307a2.cif _cod_data_source_block KK007_2 _cod_depositor_comments 'Adding full bibliography for 7248367.cif.' _cod_database_code 7248367 _shelx_res_file ; TITL KK007_2 [Space group= Pnma] job.res created by SHELXL-2019/3 at 14:06:10 on 13-Oct-2023 CELL 0.71073 13.7185 7.2021 8.8003 90.000 90.000 90.000 ZERR 4.00 0.0018 0.0009 0.0012 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, - Z SYMM 1/2 + X, 1/2 - Y, 1/2 - Z SFAC C H BR N UNIT 32 20 8 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.09 0.12 0.17 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.015500 1.658700 FVAR 0.40659 BR1 3 0.206236 0.531611 0.497163 11.00000 0.02691 0.03073 = 0.04492 -0.00872 0.00188 -0.00423 C1 1 0.281294 0.750000 0.438975 10.50000 0.02421 0.03477 = 0.02207 0.00000 0.00559 0.00000 AFIX 13 H1 2 0.288738 0.749999 0.325936 10.50000 -1.20000 AFIX 0 C2 1 0.381054 0.750000 0.509016 10.50000 0.02183 0.02149 = 0.02262 0.00000 0.00256 0.00000 C3 1 0.394149 0.750000 0.665947 10.50000 0.02764 0.03235 = 0.02148 0.00000 0.00578 0.00000 AFIX 43 H3 2 0.338674 0.750000 0.730562 10.50000 -1.20000 AFIX 0 C4 1 0.486231 0.750000 0.729493 10.50000 0.03550 0.03068 = 0.01909 0.00000 -0.00040 0.00000 AFIX 43 H4 2 0.493816 0.750000 0.836794 10.50000 -1.20000 AFIX 0 C5 1 0.567462 0.750000 0.635948 10.50000 0.02511 0.02714 = 0.02817 0.00000 -0.00514 0.00000 AFIX 43 H5 2 0.630802 0.750000 0.679584 10.50000 -1.20000 AFIX 0 C6 1 0.557171 0.750000 0.479664 10.50000 0.02133 0.02717 = 0.02548 0.00000 0.00305 0.00000 AFIX 43 H6 2 0.613112 0.750000 0.416034 10.50000 -1.20000 AFIX 0 C7 1 0.463931 0.750000 0.416080 10.50000 0.02467 0.01697 = 0.01883 0.00000 0.00306 0.00000 C8 1 0.453819 0.750000 0.252669 10.50000 0.02171 0.02295 = 0.02542 0.00000 0.00407 0.00000 N9 4 0.445398 0.750000 0.123496 10.50000 0.03348 0.03778 = 0.02180 0.00000 0.00477 0.00000 HKLF 4 REM KK007_2 [Space group= Pnma] REM wR2 = 0.0563, GooF = S = 1.045, Restrained GooF = 1.045 for all data REM R1 = 0.0238 for 883 Fo > 4sig(Fo) and 0.0316 for all 1074 data REM 64 parameters refined using 0 restraints END WGHT 0.0114 1.7221 REM Highest difference peak 0.721, deepest hole -0.604, 1-sigma level 0.073 Q1 1 0.2169 0.5723 0.4137 11.00000 0.05 0.72 Q2 1 0.3369 0.7500 0.4767 10.50000 0.05 0.28 Q3 1 0.5015 0.7500 0.4497 10.50000 0.05 0.28 Q4 1 0.5179 0.7500 0.6752 10.50000 0.05 0.28 Q5 1 0.4251 0.7765 0.4644 11.00000 0.05 0.26 Q6 1 0.2148 0.5901 0.5622 11.00000 0.05 0.24 Q7 1 0.4564 0.7500 0.3482 10.50000 0.05 0.23 Q8 1 0.3896 0.7860 0.5891 11.00000 0.05 0.23 Q9 1 0.4045 0.7500 0.1952 10.50000 0.05 0.23 Q10 1 0.4392 0.7500 0.6865 10.50000 0.05 0.22 Q11 1 0.2527 0.4575 0.5155 11.00000 0.05 0.21 Q12 1 0.2729 0.7500 0.6793 10.50000 0.05 0.21 Q13 1 0.5998 0.7500 0.8407 10.50000 0.05 0.20 Q14 1 0.2716 0.7500 0.9237 10.50000 0.05 0.19 Q15 1 0.4740 0.8066 0.1721 11.00000 0.05 0.19 Q16 1 0.4141 0.7500 -0.0110 10.50000 0.05 0.19 Q17 1 0.4932 0.7500 0.7718 10.50000 0.05 0.18 Q18 1 0.2773 0.8185 0.3650 11.00000 0.05 0.17 Q19 1 0.4622 0.9434 0.1399 11.00000 0.05 0.17 Q20 1 0.3624 0.7905 0.6929 11.00000 0.05 0.17 ; _shelx_res_checksum 46239 loop_ _space_group_symop_operation_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' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.20624(2) 0.53161(4) 0.49716(3) 0.03419(11) Uani 1 1 d . . . . . C1 C 0.2813(3) 0.750000 0.4390(4) 0.0270(8) Uani 1 2 d S T P . . H1 H 0.288738 0.749999 0.325936 0.032 Uiso 1 2 calc R U P . . C2 C 0.3811(2) 0.750000 0.5090(4) 0.0220(6) Uani 1 2 d S T P . . C3 C 0.3941(3) 0.750000 0.6659(4) 0.0272(8) Uani 1 2 d S T P . . H3 H 0.338674 0.750000 0.730562 0.033 Uiso 1 2 calc R U P . . C4 C 0.4862(3) 0.750000 0.7295(4) 0.0284(8) Uani 1 2 d S T P . . H4 H 0.493816 0.750000 0.836794 0.034 Uiso 1 2 calc R U P . . C5 C 0.5675(3) 0.750000 0.6359(4) 0.0268(8) Uani 1 2 d S T P . . H5 H 0.630802 0.750000 0.679584 0.032 Uiso 1 2 calc R U P . . C6 C 0.5572(3) 0.750000 0.4797(4) 0.0247(7) Uani 1 2 d S T P . . H6 H 0.613112 0.750000 0.416034 0.030 Uiso 1 2 calc R U P . . C7 C 0.4639(3) 0.750000 0.4161(4) 0.0202(7) Uani 1 2 d S T P . . C8 C 0.4538(2) 0.750000 0.2527(4) 0.0234(7) Uani 1 2 d S T P . . N9 N 0.4454(2) 0.750000 0.1235(3) 0.0310(7) Uani 1 2 d S T 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 Br1 0.02691(15) 0.03073(16) 0.04492(17) -0.00872(12) 0.00188(12) -0.00423(10) C1 0.0242(18) 0.035(2) 0.0221(16) 0.000 0.0056(14) 0.000 C2 0.0218(15) 0.0215(16) 0.0226(15) 0.000 0.0026(14) 0.000 C3 0.0276(18) 0.0324(19) 0.0215(16) 0.000 0.0058(14) 0.000 C4 0.036(2) 0.031(2) 0.0191(16) 0.000 -0.0004(14) 0.000 C5 0.0251(18) 0.0271(18) 0.0282(18) 0.000 -0.0051(14) 0.000 C6 0.0213(16) 0.0272(18) 0.0255(17) 0.000 0.0030(14) 0.000 C7 0.0247(17) 0.0170(15) 0.0188(15) 0.000 0.0031(13) 0.000 C8 0.0217(16) 0.0229(17) 0.0254(17) 0.000 0.0041(13) 0.000 N9 0.0335(17) 0.0378(18) 0.0218(15) 0.000 0.0048(13) 0.000 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' 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 Br1 111.96(15) . 7_575 ? C2 C1 Br1 111.96(15) . . ? Br1 C1 Br1 107.66(16) 7_575 . ? C2 C1 H1 108.4 . . ? Br1 C1 H1 108.4 7_575 . ? Br1 C1 H1 108.4 . . ? C3 C2 C7 118.3(3) . . ? C3 C2 C1 121.7(3) . . ? C7 C2 C1 120.0(3) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.6(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.5(3) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C6 C7 C2 120.6(3) . . ? C6 C7 C8 119.1(3) . . ? C2 C7 C8 120.2(3) . . ? N9 C8 C7 179.7(4) . . ? 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 C1 1.948(2) . ? C1 C2 1.501(5) . ? C1 H1 1.0000 . ? C2 C3 1.393(5) . ? C2 C7 1.401(5) . ? C3 C4 1.381(5) . ? C3 H3 0.9500 . ? C4 C5 1.385(5) . ? C4 H4 0.9500 . ? C5 C6 1.383(5) . ? C5 H5 0.9500 . ? C6 C7 1.396(5) . ? C6 H6 0.9500 . ? C7 C8 1.445(5) . ? C8 N9 1.143(4) . ? 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 Br1 C1 C2 C3 60.50(15) 7_575 . . . ? Br1 C1 C2 C3 -60.50(15) . . . . ? Br1 C1 C2 C7 -119.50(15) 7_575 . . . ? Br1 C1 C2 C7 119.50(15) . . . . ? C7 C2 C3 C4 0.000(1) . . . . ? C1 C2 C3 C4 180.000(1) . . . . ? C2 C3 C4 C5 0.000(1) . . . . ? C3 C4 C5 C6 0.000(1) . . . . ? C4 C5 C6 C7 0.000(1) . . . . ? C5 C6 C7 C2 0.000(0) . . . . ? C5 C6 C7 C8 180.000(1) . . . . ? C3 C2 C7 C6 0.000(0) . . . . ? C1 C2 C7 C6 180.000(0) . . . . ? C3 C2 C7 C8 180.000(0) . . . . ? C1 C2 C7 C8 0.000(0) . . . . ?