#------------------------------------------------------------------------------ #$Date: 2020-02-11 04:11:45 +0200 (Tue, 11 Feb 2020) $ #$Revision: 248019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557294.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_1557294 loop_ _publ_author_name 'Schnell, Simon D.' 'Hoff, Lukas V.' 'Panchagnula, Advaita' 'Wurzenberger, Maximilian Hans Horst' 'Klapoetke, Thomas M.' 'Sieber, Simon' 'Linden, Anthony' 'Gademann, Karl' _publ_section_title ; 3-Bromotetrazine: Labelling of Macromolecules via Monosubstituted Bifunctional s-Tetrazines ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC06169J _journal_year 2020 _chemical_formula_moiety 'C2 H Br N4' _chemical_formula_sum 'C2 H Br N4' _chemical_formula_weight 160.98 _chemical_melting_point 344 _chemical_name_systematic 3-bromotetrazine _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/1 _audit_update_record ; 2019-10-11 deposited with the CCDC. 2020-02-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.7468(5) _cell_length_b 5.60166(19) _cell_length_c 12.9507(4) _cell_measurement_reflns_used 2980 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 73.5270 _cell_measurement_theta_min 3.3990 _cell_volume 924.72(6) _computing_cell_refinement 'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)' _computing_data_collection 'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)' _computing_data_reduction 'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-2018 and PLATON (Spek, 2015)' _computing_structure_refinement 'SHELXL-2018 (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT-2014 (Sheldrick, 2015a)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 160(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 10.3801 _diffrn_detector_type 'Atlas CCD area detector on \k goniostat' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device 'four-circle \k-geometry diffractometer' _diffrn_measurement_device_type 'Oxford Diffraction SuperNova, dual radiation diffractometer' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_unetI/netI 0.0133 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4719 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.945 _diffrn_reflns_theta_min 6.838 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray source' _exptl_absorpt_coefficient_mu 10.963 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.481 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; Numerical absorption correction based on gaussian integration over a multifaceted crystal model plus an empirical absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm. CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2015) ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 2.313 _exptl_crystal_description plate _exptl_crystal_F_000 608 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.324 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.067 _refine_ls_extinction_coef 0.00063(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018 (Sheldrick, 2015b)' _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 65 _refine_ls_number_reflns 926 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0189 _refine_ls_R_factor_gt 0.0185 _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^)+(0.0285P)^2^+0.4717P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.0516 _reflns_Friedel_coverage 0.000 _reflns_number_gt 904 _reflns_number_total 926 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06169j2.cif _cod_data_source_block 2 _cod_database_code 1557294 _shelx_shelxl_version_number 2018/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _oxdiff_exptl_absorpt_empirical_full_min 0.742 _oxdiff_exptl_absorpt_empirical_full_max 1.469 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL gd1803_a.res in Pbca x.res created by SHELXL-2018/1 at 17:51:47 on 06-Mar-2018 REM Old TITL GD1803 in Pbca REM SHELXT solution in Pbca REM R1 0.073, Rweak 0.003, Alpha 0.019, Orientation as input REM Formula found by SHELXT: C6 Br CELL 1.54184 12.7468 5.60166 12.9507 90 90 90 ZERR 8 0.0005 0.00019 0.0004 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H Br N UNIT 16 8 8 32 TEMP -113 L.S. 10 PLAN 10 BOND $H CONF fmap 2 ACTA WGHT 0.028500 0.471700 EXTI 0.000631 FVAR 3.50941 BR1 3 0.646811 0.323707 0.475037 11.00000 0.03190 0.03146 = 0.01984 0.00168 0.00010 -0.00041 N2 4 0.584883 0.680903 0.343886 11.00000 0.02205 0.02423 = 0.03113 -0.00337 0.00169 0.00074 N3 4 0.571151 0.776433 0.250792 11.00000 0.02304 0.02650 = 0.03775 0.00521 -0.00135 0.00076 N5 4 0.663354 0.451197 0.174696 11.00000 0.02637 0.03157 = 0.02160 -0.00037 0.00154 -0.00196 N6 4 0.677312 0.354742 0.267156 11.00000 0.02231 0.02437 = 0.02231 -0.00154 -0.00021 0.00087 C1 1 0.634772 0.472126 0.346045 11.00000 0.01898 0.02126 = 0.02071 0.00008 -0.00100 -0.00137 C4 1 0.609148 0.654714 0.170686 11.00000 0.02616 0.03367 = 0.02916 0.00757 -0.00204 -0.00196 AFIX 43 H4 2 0.596353 0.719338 0.104045 11.00000 -1.20000 AFIX 0 HKLF 4 REM gd1803_a.res in Pbca REM R1 = 0.0185 for 904 Fo > 4sig(Fo) and 0.0189 for all 926 data REM 65 parameters refined using 0 restraints END WGHT 0.0285 0.4717 REM Highest difference peak 0.324, deepest hole -0.434, 1-sigma level 0.067 Q1 1 0.6458 0.1610 0.4383 11.00000 0.05 0.32 Q2 1 0.6600 0.3185 0.2474 11.00000 0.05 0.27 Q3 1 0.6075 0.5819 0.3335 11.00000 0.05 0.27 Q4 1 0.6557 0.4988 0.5201 11.00000 0.05 0.25 Q5 1 0.6424 0.4695 0.4484 11.00000 0.05 0.22 Q6 1 0.6543 0.4269 0.3058 11.00000 0.05 0.22 Q7 1 0.6404 0.3402 0.3875 11.00000 0.05 0.22 Q8 1 0.6518 0.1831 0.3300 11.00000 0.05 0.21 Q9 1 0.6424 0.1541 0.5114 11.00000 0.05 0.20 Q10 1 0.6409 0.5647 0.1814 11.00000 0.05 0.20 ; _shelx_res_checksum 50521 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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 Br1 Br 0.64681(2) 0.32371(4) 0.47504(2) 0.02773(12) Uani 1 1 d . . N2 N 0.58488(13) 0.6809(3) 0.34389(14) 0.0258(4) Uani 1 1 d . . N3 N 0.57115(14) 0.7764(3) 0.25079(15) 0.0291(3) Uani 1 1 d . . N5 N 0.66335(13) 0.4512(3) 0.17470(12) 0.0265(3) Uani 1 1 d . . N6 N 0.67731(13) 0.3547(3) 0.26716(12) 0.0230(3) Uani 1 1 d . . C1 C 0.63477(13) 0.4721(3) 0.34604(14) 0.0203(3) Uani 1 1 d . . C4 C 0.60915(17) 0.6547(3) 0.17069(16) 0.0297(4) Uani 1 1 d . . H4 H 0.596353 0.719338 0.104045 0.036 Uiso 1 1 calc R U 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 0.03190(18) 0.03146(17) 0.01984(15) 0.00168(6) 0.00010(7) -0.00041(7) N2 0.0220(8) 0.0242(8) 0.0311(9) -0.0034(6) 0.0017(7) 0.0007(5) N3 0.0230(8) 0.0265(8) 0.0378(8) 0.0052(7) -0.0014(7) 0.0008(6) N5 0.0264(8) 0.0316(8) 0.0216(7) -0.0004(6) 0.0015(6) -0.0020(6) N6 0.0223(8) 0.0244(7) 0.0223(7) -0.0015(6) -0.0002(6) 0.0009(6) C1 0.0190(8) 0.0213(8) 0.0207(8) 0.0001(7) -0.0010(6) -0.0014(6) C4 0.0262(11) 0.0337(10) 0.0292(10) 0.0076(8) -0.0020(8) -0.0020(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0230 0 0 -1 0.0230 -1 0 0 0.0387 1 0 0 0.0410 1 4 -1 0.1284 5 -3 1 0.0956 -5 -1 0 0.0549 -5 1 0 0.0735 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N3 N2 C1 115.79(16) N2 N3 C4 116.86(16) N6 N5 C4 116.93(16) N5 N6 C1 115.94(15) N6 C1 N2 127.78(17) N6 C1 Br1 115.61(13) N2 C1 Br1 116.61(14) N3 C4 N5 126.53(19) N3 C4 H4 116.7 N5 C4 H4 116.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1 1.8723(19) N2 N3 1.331(2) N2 C1 1.332(2) N3 C4 1.333(3) N5 N6 1.326(2) N5 C4 1.334(3) N6 C1 1.330(2) C4 H4 0.9500 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 C1 N2 N3 C4 -0.5(2) C4 N5 N6 C1 0.4(2) N5 N6 C1 N2 -4.0(3) N5 N6 C1 Br1 175.90(12) N3 N2 C1 N6 4.0(3) N3 N2 C1 Br1 -175.86(13) N2 N3 C4 N5 -2.9(3) N6 N5 C4 N3 3.0(3) loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.0001 0.0008 1.0016 -0.0028 0.1188 -0.0088 -0.0001 -0.0008 -1.0016 0.0028 -0.1188 0.0088 -0.9993 -0.0012 -0.0011 0.0312 0.0092 0.1164 0.9993 0.0012 0.0011 -0.0312 -0.0092 -0.1164 0.9696 3.9958 -1.0084 -1.0890 -0.1317 0.1767 5.0190 -2.9899 1.0131 0.6364 0.0753 -0.8040 -4.9892 -1.0047 -0.0036 0.4214 0.0472 0.5108 -5.0041 0.9930 -0.0076 -0.1089 0.0453 0.6530