#------------------------------------------------------------------------------ #$Date: 2020-02-11 04:11:45 +0200 (Tue, 11 Feb 2020) $ #$Revision: 248019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557292.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_1557292 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_absolute_configuration ad _chemical_formula_moiety 'C10 H7 N5' _chemical_formula_sum 'C10 H7 N5' _chemical_formula_weight 197.21 _chemical_melting_point 377 _chemical_name_systematic 1-(S-tetrazin-3-yl)-1H-indole _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_Hall 'F 2 -2d' _space_group_name_H-M_alt 'F d d 2' _atom_sites_solution_hydrogens geom _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 16 _cell_length_a 38.7645(3) _cell_length_b 11.93147(14) _cell_length_c 7.70847(8) _cell_measurement_reflns_used 6471 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 73.9210 _cell_measurement_theta_min 4.5210 _cell_volume 3565.30(6) _computing_cell_refinement 'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)' _computing_data_collection 'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)' _computing_data_reduction 'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)' _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-2018 (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 0.992 _diffrn_measured_fraction_theta_max 0.983 _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 0.0132 _diffrn_reflns_av_unetI/netI 0.0076 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_h_min -47 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 8381 _diffrn_reflns_point_group_measured_fraction_full 0.961 _diffrn_reflns_point_group_measured_fraction_max 0.941 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.042 _diffrn_reflns_theta_min 4.563 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray source' _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm. CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018) ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.470 _exptl_crystal_description tablet _exptl_crystal_F_000 1632 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: diethyl ether' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.154 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.028 _refine_ls_abs_structure_details ; Flack x determined using 740 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.01(7) _refine_ls_extinction_coef 0.00026(5) _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 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 1702 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0228 _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^)+(0.0379P)^2^+1.6158P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.0608 _reflns_Friedel_coverage 0.777 _reflns_Friedel_fraction_full 0.925 _reflns_Friedel_fraction_max 0.893 _reflns_number_gt 1689 _reflns_number_total 1702 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06169j2.cif _cod_data_source_block 9 _cod_database_code 1557292 _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. ; _oxdiff_exptl_absorpt_empirical_full_min 0.845 _oxdiff_exptl_absorpt_empirical_full_max 1.165 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL gd1901_cu_a.res in Fdd2 x.res created by SHELXL-2018/3 at 08:55:43 on 22-Jan-2019 REM Old TITL GD1901_Cu in Fdd2 REM SHELXT solution in Fdd2: R1 0.080, Rweak 0.018, Alpha 0.002 REM 1.169 for 63 systematic absences, Orientation as input REM Flack x = -0.029 ( 0.105 ) from 740 Parsons' quotients REM Formula found by SHELXT: N4 N2 CELL 1.54184 38.7645 11.93147 7.70847 90 90 90 ZERR 16 0.0003 0.00014 0.00008 0 0 0 LATT -4 SYMM -X,-Y,+Z SYMM 0.25+X,0.25-Y,0.25+Z SYMM 0.25-X,0.25+Y,0.25+Z SFAC C H N UNIT 160 112 80 TEMP -113 L.S. 4 PLAN 10 BOND $H CONF fmap 2 ACTA WGHT 0.037900 1.615800 EXTI 0.000259 FVAR 2.23389 N1 3 0.292344 0.507340 0.552327 11.00000 0.02559 0.03469 = 0.03537 0.00233 0.00643 0.00182 N2 3 0.262859 0.474946 0.484027 11.00000 0.02357 0.04364 = 0.04370 0.00613 0.00465 0.00148 N3 3 0.292246 0.348416 0.298459 11.00000 0.02756 0.04612 = 0.03561 -0.00203 -0.00229 -0.00624 N4 3 0.322187 0.381252 0.363680 11.00000 0.02317 0.03646 = 0.03233 -0.00362 0.00038 -0.00313 N5 3 0.352002 0.505103 0.542200 11.00000 0.02437 0.02354 = 0.02334 -0.00019 0.00275 0.00117 C1 1 0.321180 0.463580 0.481908 11.00000 0.02436 0.02625 = 0.02370 0.00624 0.00321 0.00010 C2 1 0.264046 0.400066 0.355363 11.00000 0.02394 0.04996 = 0.04092 0.00510 -0.00213 -0.00373 AFIX 43 H2 2 0.242893 0.382156 0.299654 11.00000 -1.20000 AFIX 0 C3 1 0.354699 0.591198 0.666192 11.00000 0.03625 0.02435 = 0.02534 -0.00228 0.00453 0.00306 AFIX 43 H3 2 0.335785 0.629695 0.717096 11.00000 -1.20000 AFIX 0 C4 1 0.388082 0.610653 0.701602 11.00000 0.03721 0.02437 = 0.02805 -0.00303 -0.00050 -0.00189 AFIX 43 H4 2 0.396687 0.664387 0.781590 11.00000 -1.20000 AFIX 0 C5 1 0.408495 0.536163 0.597613 11.00000 0.03036 0.02214 = 0.02370 0.00272 -0.00113 -0.00307 C6 1 0.444079 0.519156 0.582418 11.00000 0.02859 0.03067 = 0.03126 0.00081 -0.00474 -0.00690 AFIX 43 H6 2 0.459818 0.562268 0.649287 11.00000 -1.20000 AFIX 0 C7 1 0.455898 0.438583 0.468478 11.00000 0.02194 0.03261 = 0.03563 0.00240 0.00015 -0.00094 AFIX 43 H7 2 0.479995 0.425948 0.457446 11.00000 -1.20000 AFIX 0 C8 1 0.432838 0.375323 0.369085 11.00000 0.02625 0.02871 = 0.03035 -0.00117 0.00271 0.00151 AFIX 43 H8 2 0.441639 0.320876 0.290810 11.00000 -1.20000 AFIX 0 C9 1 0.397348 0.390120 0.381956 11.00000 0.02563 0.02548 = 0.02701 -0.00258 -0.00040 -0.00185 AFIX 43 H9 2 0.381761 0.346870 0.314411 11.00000 -1.20000 AFIX 0 C10 1 0.385645 0.470874 0.497839 11.00000 0.02253 0.02140 = 0.02197 0.00354 0.00004 -0.00063 HKLF 4 REM gd1901_cu_a.res in Fdd2 REM wR2 = 0.0608, GooF = S = 1.072, Restrained GooF = 1.072 for all data REM R1 = 0.0228 for 1689 Fo > 4sig(Fo) and 0.0230 for all 1702 data REM 137 parameters refined using 1 restraints END WGHT 0.0379 1.6157 REM Highest difference peak 0.154, deepest hole -0.113, 1-sigma level 0.028 Q1 1 0.3998 0.5161 0.5236 11.00000 0.05 0.15 Q2 1 0.3681 0.4815 0.5093 11.00000 0.05 0.13 Q3 1 0.3391 0.4844 0.5277 11.00000 0.05 0.13 Q4 1 0.3893 0.4509 0.4054 11.00000 0.05 0.13 Q5 1 0.4247 0.5432 0.5857 11.00000 0.05 0.12 Q6 1 0.3282 0.6223 0.6628 11.00000 0.05 0.12 Q7 1 0.4164 0.4011 0.3551 11.00000 0.05 0.11 Q8 1 0.4008 0.5896 0.6338 11.00000 0.05 0.11 Q9 1 0.3897 0.4087 0.4709 11.00000 0.05 0.10 Q10 1 0.5000 0.5000 0.5863 10.50000 0.05 0.10 ; _shelx_res_checksum 5611 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' 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 N1 N 0.29234(3) 0.50734(12) 0.55233(18) 0.0319(3) Uani 1 1 d . . N2 N 0.26286(3) 0.47495(13) 0.4840(2) 0.0370(3) Uani 1 1 d . . N3 N 0.29225(3) 0.34842(13) 0.2985(2) 0.0364(4) Uani 1 1 d . . N4 N 0.32219(3) 0.38125(12) 0.36368(17) 0.0307(3) Uani 1 1 d . . N5 N 0.35200(3) 0.50510(10) 0.54220(15) 0.0238(3) Uani 1 1 d . . C1 C 0.32118(4) 0.46358(13) 0.48191(19) 0.0248(3) Uani 1 1 d . . C2 C 0.26405(4) 0.40007(16) 0.3554(2) 0.0383(4) Uani 1 1 d . . H2 H 0.242893 0.382156 0.299654 0.046 Uiso 1 1 calc R U C3 C 0.35470(4) 0.59120(13) 0.6662(2) 0.0286(3) Uani 1 1 d . . H3 H 0.335785 0.629695 0.717096 0.034 Uiso 1 1 calc R U C4 C 0.38808(4) 0.61065(13) 0.7016(2) 0.0299(3) Uani 1 1 d . . H4 H 0.396687 0.664387 0.781590 0.036 Uiso 1 1 calc R U C5 C 0.40850(4) 0.53616(12) 0.5976(2) 0.0254(3) Uani 1 1 d . . C6 C 0.44408(4) 0.51916(13) 0.5824(2) 0.0302(3) Uani 1 1 d . . H6 H 0.459818 0.562268 0.649287 0.036 Uiso 1 1 calc R U C7 C 0.45590(4) 0.43858(14) 0.4685(2) 0.0301(3) Uani 1 1 d . . H7 H 0.479995 0.425948 0.457446 0.036 Uiso 1 1 calc R U C8 C 0.43284(4) 0.37532(14) 0.3691(2) 0.0284(3) Uani 1 1 d . . H8 H 0.441639 0.320876 0.290810 0.034 Uiso 1 1 calc R U C9 C 0.39735(4) 0.39012(13) 0.3820(2) 0.0260(3) Uani 1 1 d . . H9 H 0.381761 0.346870 0.314411 0.031 Uiso 1 1 calc R U C10 C 0.38565(4) 0.47087(12) 0.49784(17) 0.0220(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 N1 0.0256(6) 0.0347(7) 0.0354(7) 0.0023(6) 0.0064(5) 0.0018(5) N2 0.0236(6) 0.0436(8) 0.0437(8) 0.0061(7) 0.0047(6) 0.0015(5) N3 0.0276(7) 0.0461(9) 0.0356(7) -0.0020(7) -0.0023(6) -0.0062(6) N4 0.0232(6) 0.0365(8) 0.0323(7) -0.0036(6) 0.0004(6) -0.0031(5) N5 0.0244(6) 0.0235(6) 0.0233(6) -0.0002(5) 0.0027(5) 0.0012(4) C1 0.0244(7) 0.0263(8) 0.0237(7) 0.0062(6) 0.0032(5) 0.0001(5) C2 0.0239(7) 0.0500(11) 0.0409(9) 0.0051(8) -0.0021(7) -0.0037(7) C3 0.0362(8) 0.0243(8) 0.0253(7) -0.0023(6) 0.0045(6) 0.0031(6) C4 0.0372(8) 0.0244(8) 0.0280(8) -0.0030(6) -0.0005(7) -0.0019(6) C5 0.0304(7) 0.0221(7) 0.0237(6) 0.0027(5) -0.0011(6) -0.0031(6) C6 0.0286(7) 0.0307(8) 0.0313(8) 0.0008(6) -0.0047(6) -0.0069(6) C7 0.0219(6) 0.0326(8) 0.0356(8) 0.0024(7) 0.0001(6) -0.0009(6) C8 0.0262(7) 0.0287(8) 0.0303(8) -0.0012(6) 0.0027(6) 0.0015(6) C9 0.0256(7) 0.0255(8) 0.0270(7) -0.0026(5) -0.0004(6) -0.0019(5) C10 0.0225(6) 0.0214(7) 0.0220(7) 0.0035(5) 0.0000(5) -0.0006(5) 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' N N 0.0311 0.0180 '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 N2 N1 C1 116.44(14) N1 N2 C2 117.61(14) N4 N3 C2 117.28(15) N3 N4 C1 116.71(13) C1 N5 C3 123.88(12) C1 N5 C10 128.18(12) C3 N5 C10 107.93(12) N4 C1 N1 125.58(14) N4 C1 N5 117.95(13) N1 C1 N5 116.43(14) N3 C2 N2 125.69(15) N3 C2 H2 117.2 N2 C2 H2 117.2 C4 C3 N5 109.63(13) C4 C3 H3 125.2 N5 C3 H3 125.2 C3 C4 C5 108.11(13) C3 C4 H4 125.9 C5 C4 H4 125.9 C6 C5 C10 119.62(14) C6 C5 C4 132.87(14) C10 C5 C4 107.51(12) C7 C6 C5 118.78(14) C7 C6 H6 120.6 C5 C6 H6 120.6 C6 C7 C8 120.82(14) C6 C7 H7 119.6 C8 C7 H7 119.6 C9 C8 C7 121.65(15) C9 C8 H8 119.2 C7 C8 H8 119.2 C10 C9 C8 117.18(14) C10 C9 H9 121.4 C8 C9 H9 121.4 C9 C10 C5 121.95(13) C9 C10 N5 131.23(13) C5 C10 N5 106.82(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 N2 1.3164(19) N1 C1 1.3479(18) N2 C2 1.336(2) N3 N4 1.3241(18) N3 C2 1.329(2) N4 C1 1.341(2) N5 C1 1.3744(18) N5 C3 1.4070(19) N5 C10 1.4087(18) C2 H2 0.9500 C3 C4 1.343(2) C3 H3 0.9500 C4 C5 1.435(2) C4 H4 0.9500 C5 C6 1.399(2) C5 C10 1.408(2) C6 C7 1.380(2) C6 H6 0.9500 C7 C8 1.399(2) C7 H7 0.9500 C8 C9 1.391(2) C8 H8 0.9500 C9 C10 1.390(2) C9 H9 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 N1 N2 C2 1.7(2) C2 N3 N4 C1 0.2(2) N3 N4 C1 N1 7.2(2) N3 N4 C1 N5 -175.23(14) N2 N1 C1 N4 -8.2(2) N2 N1 C1 N5 174.17(12) C3 N5 C1 N4 -179.92(14) C10 N5 C1 N4 -1.2(2) C3 N5 C1 N1 -2.1(2) C10 N5 C1 N1 176.61(13) N4 N3 C2 N2 -6.6(3) N1 N2 C2 N3 5.5(3) C1 N5 C3 C4 178.25(13) C10 N5 C3 C4 -0.70(16) N5 C3 C4 C5 0.44(18) C3 C4 C5 C6 -179.39(16) C3 C4 C5 C10 -0.01(18) C10 C5 C6 C7 0.3(2) C4 C5 C6 C7 179.64(17) C5 C6 C7 C8 0.3(2) C6 C7 C8 C9 -0.6(3) C7 C8 C9 C10 0.1(2) C8 C9 C10 C5 0.5(2) C8 C9 C10 N5 -179.26(15) C6 C5 C10 C9 -0.8(2) C4 C5 C10 C9 179.74(13) C6 C5 C10 N5 179.06(13) C4 C5 C10 N5 -0.41(16) C1 N5 C10 C9 1.6(2) C3 N5 C10 C9 -179.50(15) C1 N5 C10 C5 -178.22(13) C3 N5 C10 C5 0.67(15)