#------------------------------------------------------------------------------ #$Date: 2020-02-11 04:11:45 +0200 (Tue, 11 Feb 2020) $ #$Revision: 248019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557290.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_1557290 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 Cl N4' _chemical_formula_sum 'C2 H Cl N4' _chemical_formula_weight 116.52 _chemical_name_systematic 3-chlorotetrazine _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 difmap _audit_creation_method SHELXL-2018/3 _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 11.2724(5) _cell_length_b 6.2790(4) _cell_length_c 12.5272(7) _cell_measurement_reflns_used 3146 _cell_measurement_temperature 160(1) _cell_measurement_theta_max 74.4240 _cell_measurement_theta_min 7.0950 _cell_volume 886.67(8) _computing_cell_refinement 'CrysAlisPro, Version 1.171.39.13a (Rigaku Oxford Diffraction, 2017)' _computing_data_collection 'CrysAlisPro, Version 1.171.39.13a (Rigaku Oxford Diffraction, 2017)' _computing_data_reduction 'CrysAlisPro, Version 1.171.39.13a (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, 2015)' _computing_structure_solution 'SHELXS-2013 (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 160(1) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0193 _diffrn_reflns_av_unetI/netI 0.0119 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4312 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.503 _diffrn_reflns_theta_min 7.070 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray source' _exptl_absorpt_coefficient_mu 6.417 _exptl_absorpt_correction_T_max 0.858 _exptl_absorpt_correction_T_min 0.382 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; Analytical numeric absorption correction using a multifaceted crystal model [Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897] plus an empirical absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm. CrysAlisPro, Version 1.171.39.13a (Rigaku Oxford Diffraction, 2016) ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.746 _exptl_crystal_description plate _exptl_crystal_F_000 464 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.161 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 68 _refine_ls_number_reflns 903 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0281 _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^)+(0.0494P)^2^+0.2063P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.0772 _reflns_Friedel_coverage 0.000 _reflns_number_gt 883 _reflns_number_total 904 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06169j2.cif _cod_data_source_block 1 _cod_original_cell_volume 886.67(9) _cod_database_code 1557290 _shelx_shelxl_version_number 2018/3 _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. ; _shelx_estimated_absorpt_t_min 0.286 _shelx_estimated_absorpt_t_max 0.882 _oxdiff_exptl_absorpt_empirical_full_min 0.649 _oxdiff_exptl_absorpt_empirical_full_max 1.502 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _shelx_res_file ; TITL exp_1631_a.res in Pbca x.res created by SHELXL-2018/3 at 17:46:24 on 05-Apr-2018 CELL 1.54184 11.272432 6.279025 12.527169 90 90 90 ZERR 8 0.000529 0.000413 0.000658 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 Cl N UNIT 16 8 8 32 L.S. 10 PLAN 20 SIZE 0.02 0.13 0.26 BOND $H CONF fmap 2 acta OMIT 0 2 0 REM REM REM WGHT 0.049400 0.206300 FVAR 6.85556 C1 1 0.625655 0.481454 0.704902 11.00000 0.03045 0.02006 = 0.02499 0.00144 -0.00038 0.00249 C2 1 0.614828 0.562257 0.901187 11.00000 0.03775 0.02731 = 0.02429 -0.00116 0.00156 0.00016 H2 2 0.611767 0.595236 0.973693 11.00000 0.03556 CL1 3 0.632367 0.429527 0.571122 11.00000 0.04837 0.03746 = 0.02222 0.00000 -0.00097 0.00239 N1 4 0.538642 0.386736 0.758730 11.00000 0.03252 0.02346 = 0.02878 -0.00032 0.00204 -0.00256 N2 4 0.533505 0.430566 0.862380 11.00000 0.03492 0.02629 = 0.02882 0.00088 0.00501 -0.00180 N3 4 0.702694 0.652883 0.846902 11.00000 0.03745 0.02740 = 0.02925 -0.00236 -0.00079 -0.00438 N4 4 0.708607 0.610320 0.743233 11.00000 0.03388 0.02639 = 0.02879 0.00185 0.00166 -0.00432 HKLF 4 REM exp_1631_a.res in Pbca REM wR2 = 0.0772, GooF = S = 1.096, Restrained GooF = 1.096 for all data REM R1 = 0.0281 for 883 Fo > 4sig(Fo) and 0.0285 for all 903 data REM 68 parameters refined using 0 restraints END WGHT 0.0494 0.2059 REM Highest difference peak 0.161, deepest hole -0.338, 1-sigma level 0.060 Q1 1 0.5286 0.5544 0.5711 11.00000 0.05 0.16 Q2 1 0.8767 0.5032 0.8789 11.00000 0.05 0.13 Q3 1 0.7514 0.4991 0.5769 11.00000 0.05 0.13 Q4 1 0.7378 0.6453 0.6837 11.00000 0.05 0.13 Q5 1 0.5430 0.2933 0.5709 11.00000 0.05 0.13 Q6 1 0.5245 0.4314 0.5234 11.00000 0.05 0.12 Q7 1 0.6188 0.4868 0.6625 11.00000 0.05 0.12 Q8 1 0.4860 0.3965 0.9135 11.00000 0.05 0.12 Q9 1 0.4392 0.5504 0.7809 11.00000 0.05 0.12 Q10 1 0.6056 0.6033 1.0733 11.00000 0.05 0.11 Q11 1 0.6506 0.5545 0.7214 11.00000 0.05 0.11 Q12 1 0.6268 0.9058 0.9183 11.00000 0.05 0.11 Q13 1 0.7166 0.4325 0.9015 11.00000 0.05 0.11 Q14 1 0.8795 0.5458 0.8299 11.00000 0.05 0.11 Q15 1 0.6232 0.5671 0.9973 11.00000 0.05 0.11 Q16 1 0.6572 0.4058 1.0496 11.00000 0.05 0.11 Q17 1 0.6246 0.3974 1.0499 11.00000 0.05 0.11 Q18 1 0.5922 0.4454 0.7316 11.00000 0.05 0.11 Q19 1 0.7397 0.3166 0.5719 11.00000 0.05 0.11 Q20 1 0.7486 0.5547 0.9310 11.00000 0.05 0.10 ; _shelx_res_checksum 55627 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 C1 C 0.62566(9) 0.4815(2) 0.70490(11) 0.0252(3) Uani 1 1 d C2 C 0.61483(12) 0.5623(2) 0.90119(12) 0.0298(3) Uani 1 1 d H2 H 0.6118(14) 0.595(3) 0.9737(16) 0.036(5) Uiso 1 1 d Cl1 Cl 0.63237(3) 0.42953(6) 0.57112(3) 0.03602(17) Uani 1 1 d N1 N 0.53864(9) 0.38674(17) 0.75873(9) 0.0283(3) Uani 1 1 d N2 N 0.53351(10) 0.43057(17) 0.86238(9) 0.0300(3) Uani 1 1 d N3 N 0.70269(10) 0.65288(18) 0.84690(9) 0.0314(3) Uani 1 1 d N4 N 0.70861(9) 0.61032(17) 0.74323(10) 0.0297(3) Uani 1 1 d 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 C1 0.0305(6) 0.0201(6) 0.0250(7) 0.0014(5) -0.0004(4) 0.0025(4) C2 0.0378(7) 0.0273(7) 0.0243(7) -0.0012(5) 0.0016(5) 0.0002(5) Cl1 0.0484(3) 0.0375(3) 0.0222(2) 0.00000(11) -0.00097(11) 0.00239(12) N1 0.0325(6) 0.0235(5) 0.0288(6) -0.0003(4) 0.0020(4) -0.0026(4) N2 0.0349(6) 0.0263(6) 0.0288(6) 0.0009(4) 0.0050(4) -0.0018(4) N3 0.0374(6) 0.0274(6) 0.0293(6) -0.0024(4) -0.0008(4) -0.0044(4) N4 0.0339(6) 0.0264(6) 0.0288(6) 0.0019(4) 0.0017(4) -0.0043(4) 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' Cl Cl 0.3639 0.7018 '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 0.0151 0 0 -1 0.0091 -4 3 0 0.0648 4 -3 0 0.0648 5 3 -1 0.1311 -5 -3 1 0.0971 6 -2 -1 0.0908 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N4 C1 N1 127.50(13) N4 C1 Cl1 116.11(10) N1 C1 Cl1 116.38(9) N2 C2 N3 126.45(14) N2 C2 H2 118.0(10) N3 C2 H2 115.5(10) N2 N1 C1 115.77(11) C2 N2 N1 117.20(11) N4 N3 C2 116.85(11) C1 N4 N3 116.20(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N4 1.3265(16) C1 N1 1.3306(16) C1 Cl1 1.7090(14) C2 N2 1.3268(18) C2 N3 1.3294(18) C2 H2 0.93(2) N1 N2 1.3285(16) N3 N4 1.3276(16) 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 N4 C1 N1 N2 1.47(18) Cl1 C1 N1 N2 -179.17(9) N3 C2 N2 N1 -1.1(2) C1 N1 N2 C2 -0.16(16) N2 C2 N3 N4 1.2(2) N1 C1 N4 N3 -1.42(19) Cl1 C1 N4 N3 179.22(9) C2 N3 N4 C1 0.07(17) 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 -0.0005 0.0002 0.9996 0.1126 -0.0483 0.0111 0.0005 -0.0002 -0.9996 -0.1126 0.0483 -0.0111 -3.9959 2.9941 -0.0036 0.3236 0.8143 0.2661 3.9959 -2.9941 0.0036 -0.3236 -0.8143 -0.2661 4.9963 2.9997 -1.0012 0.1438 0.4420 -0.8971 -4.9963 -2.9997 1.0012 -0.1438 -0.4420 0.8971 5.9947 -1.9941 -0.9965 -0.3532 -0.6503 -0.6152