#------------------------------------------------------------------------------ #$Date: 2020-02-11 04:11:45 +0200 (Tue, 11 Feb 2020) $ #$Revision: 248019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557291.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_1557291 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 'C8 H6 N4 O' _chemical_formula_sum 'C8 H6 N4 O' _chemical_formula_weight 174.17 _chemical_melting_point 385 _chemical_name_systematic 3-phenoxy-s-tetrazine _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _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 105.056(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.7358(3) _cell_length_b 5.14454(12) _cell_length_c 14.9437(4) _cell_measurement_reflns_used 5042 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 28.2460 _cell_measurement_theta_min 3.8220 _cell_volume 797.02(4) _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 0.999 _diffrn_measured_fraction_theta_max 0.897 _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 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_unetI/netI 0.0151 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.897 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 9349 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.897 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.233 _diffrn_reflns_theta_min 2.823 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray source' _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86585 _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 1.451 _exptl_crystal_description tablet _exptl_crystal_F_000 360 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.197 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.012(2) _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 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 1936 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0345 _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^)+(0.0344P)^2^+0.2119P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0801 _refine_ls_wR_factor_ref 0.0868 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1614 _reflns_number_total 1936 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06169j2.cif _cod_data_source_block 4 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557291 _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 0.902 _oxdiff_exptl_absorpt_empirical_full_max 1.241 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL gd1809_mo_a.res in P2(1)/c x.res created by SHELXL-2018/3 at 11:16:16 on 16-Oct-2018 REM Old TITL GD1809_Mo in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.154, Rweak 0.150, Alpha 0.012 REM 0.413 for 190 systematic absences, Orientation as input REM Formula found by SHELXT: C9 O1 CELL 0.71073 10.7358 5.14454 14.9437 90 105.056 90 ZERR 4 0.0003 0.00012 0.0004 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 32 24 16 4 L.S. 4 PLAN 10 TEMP -113 BOND $H CONF fmap 2 acta WGHT 0.034400 0.211900 EXTI 0.011828 FVAR 5.59380 O1 4 0.652892 0.114475 0.729530 11.00000 0.03918 0.03570 = 0.04050 -0.01138 0.01980 -0.01266 N2 3 0.556459 0.189539 0.841965 11.00000 0.02636 0.03394 = 0.03543 0.00438 0.01097 -0.00073 N3 3 0.542732 0.336023 0.910871 11.00000 0.03051 0.04279 = 0.03366 0.00429 0.01361 0.00182 N5 3 0.710813 0.614551 0.892749 11.00000 0.03755 0.03682 = 0.03155 -0.00587 0.01420 -0.00445 N6 3 0.726933 0.466548 0.823547 11.00000 0.02987 0.03238 = 0.03067 -0.00415 0.01185 -0.00398 C1 1 0.646990 0.266658 0.800304 11.00000 0.02440 0.02860 = 0.02872 0.00092 0.00793 0.00022 C4 1 0.618421 0.545621 0.931884 11.00000 0.03978 0.04298 = 0.03369 -0.00416 0.01742 -0.00106 AFIX 43 H4 2 0.604556 0.655585 0.979454 11.00000 -1.20000 AFIX 0 C5 1 0.748512 0.162508 0.681575 11.00000 0.02899 0.02858 = 0.02926 -0.00779 0.01042 -0.00577 C6 1 0.849387 -0.009113 0.696156 11.00000 0.03551 0.03107 = 0.03699 0.00082 0.00559 0.00026 AFIX 43 H6 2 0.857060 -0.146619 0.739685 11.00000 -1.20000 AFIX 0 C7 1 0.940002 0.023166 0.645703 11.00000 0.03049 0.03693 = 0.05223 -0.00550 0.01082 0.00479 AFIX 43 H7 2 1.010974 -0.093006 0.654752 11.00000 -1.20000 AFIX 0 C8 1 0.927667 0.222816 0.582515 11.00000 0.03502 0.03980 = 0.04130 -0.01137 0.01849 -0.00633 AFIX 43 H8 2 0.990240 0.244189 0.548336 11.00000 -1.20000 AFIX 0 C9 1 0.824329 0.392157 0.568773 11.00000 0.04533 0.03507 = 0.03545 0.00185 0.01528 -0.00077 AFIX 43 H9 2 0.815885 0.529173 0.524982 11.00000 -1.20000 AFIX 0 C10 1 0.732923 0.362317 0.618838 11.00000 0.03334 0.03285 = 0.03964 -0.00008 0.01196 0.00549 AFIX 43 H10 2 0.661471 0.477229 0.609886 11.00000 -1.20000 AFIX 0 HKLF 4 REM gd1809_mo_a.res in P2(1)/c REM wR2 = 0.0868, GooF = S = 1.048, Restrained GooF = 1.048 for all data REM R1 = 0.0345 for 1614 Fo > 4sig(Fo) and 0.0445 for all 1936 data REM 119 parameters refined using 0 restraints END WGHT 0.0344 0.2120 REM Highest difference peak 0.197, deepest hole -0.186, 1-sigma level 0.034 Q1 1 0.7637 0.3151 0.6754 11.00000 0.05 0.20 Q2 1 0.7792 0.0257 0.6737 11.00000 0.05 0.19 Q3 1 0.8185 0.1440 0.7087 11.00000 0.05 0.18 Q4 1 0.7610 0.3156 0.5797 11.00000 0.05 0.16 Q5 1 0.5064 0.2760 0.9528 11.00000 0.05 0.15 Q6 1 0.9123 0.0393 0.6851 11.00000 0.05 0.15 Q7 1 0.9571 0.1713 0.6353 11.00000 0.05 0.15 Q8 1 0.7317 0.2231 0.6399 11.00000 0.05 0.14 Q9 1 0.7203 0.3093 0.8361 11.00000 0.05 0.14 Q10 1 0.8947 0.3340 0.5994 11.00000 0.05 0.14 ; _shelx_res_checksum 90414 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O1 O 0.65289(8) 0.11448(16) 0.72953(6) 0.0367(2) Uani 1 1 d . . N2 N 0.55646(8) 0.18954(19) 0.84196(6) 0.0314(2) Uani 1 1 d . . N3 N 0.54273(9) 0.3360(2) 0.91087(6) 0.0347(2) Uani 1 1 d . . N5 N 0.71081(9) 0.6146(2) 0.89275(6) 0.0343(2) Uani 1 1 d . . N6 N 0.72693(9) 0.46655(19) 0.82355(6) 0.0302(2) Uani 1 1 d . . C1 C 0.64699(10) 0.2667(2) 0.80030(7) 0.0270(2) Uani 1 1 d . . C4 C 0.61842(12) 0.5456(3) 0.93188(8) 0.0374(3) Uani 1 1 d . . H4 H 0.604556 0.655585 0.979454 0.045 Uiso 1 1 calc R U C5 C 0.74851(10) 0.1625(2) 0.68158(7) 0.0284(2) Uani 1 1 d . . C6 C 0.84939(11) -0.0091(2) 0.69616(8) 0.0352(3) Uani 1 1 d . . H6 H 0.857060 -0.146619 0.739685 0.042 Uiso 1 1 calc R U C7 C 0.94000(11) 0.0232(2) 0.64570(9) 0.0399(3) Uani 1 1 d . . H7 H 1.010974 -0.093006 0.654752 0.048 Uiso 1 1 calc R U C8 C 0.92767(11) 0.2228(2) 0.58252(8) 0.0371(3) Uani 1 1 d . . H8 H 0.990240 0.244189 0.548336 0.045 Uiso 1 1 calc R U C9 C 0.82433(12) 0.3922(2) 0.56877(8) 0.0377(3) Uani 1 1 d . . H9 H 0.815885 0.529173 0.524982 0.045 Uiso 1 1 calc R U C10 C 0.73292(11) 0.3623(2) 0.61884(8) 0.0348(3) Uani 1 1 d . . H10 H 0.661471 0.477229 0.609886 0.042 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 O1 0.0392(5) 0.0357(5) 0.0405(5) -0.0114(4) 0.0198(4) -0.0127(4) N2 0.0264(5) 0.0339(5) 0.0354(5) 0.0044(4) 0.0110(4) -0.0007(4) N3 0.0305(5) 0.0428(6) 0.0337(5) 0.0043(4) 0.0136(4) 0.0018(4) N5 0.0375(5) 0.0368(5) 0.0315(5) -0.0059(4) 0.0142(4) -0.0044(4) N6 0.0299(5) 0.0324(5) 0.0307(5) -0.0042(4) 0.0119(4) -0.0040(4) C1 0.0244(5) 0.0286(5) 0.0287(5) 0.0009(4) 0.0079(4) 0.0002(4) C4 0.0398(6) 0.0430(7) 0.0337(6) -0.0042(5) 0.0174(5) -0.0011(5) C5 0.0290(5) 0.0286(5) 0.0293(5) -0.0078(4) 0.0104(4) -0.0058(4) C6 0.0355(6) 0.0311(6) 0.0370(6) 0.0008(5) 0.0056(5) 0.0003(5) C7 0.0305(6) 0.0369(7) 0.0522(7) -0.0055(6) 0.0108(5) 0.0048(5) C8 0.0350(6) 0.0398(7) 0.0413(6) -0.0114(5) 0.0185(5) -0.0063(5) C9 0.0453(7) 0.0351(6) 0.0354(6) 0.0019(5) 0.0153(5) -0.0008(5) C10 0.0333(6) 0.0329(6) 0.0396(6) -0.0001(5) 0.0120(5) 0.0055(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 '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 C1 O1 C5 119.30(8) N3 N2 C1 115.82(9) N2 N3 C4 117.46(9) C4 N5 N6 116.96(10) C1 N6 N5 116.16(9) N6 C1 O1 120.20(9) N6 C1 N2 127.19(10) O1 C1 N2 112.60(9) N5 C4 N3 126.25(11) N5 C4 H4 116.9 N3 C4 H4 116.9 C6 C5 C10 122.86(10) C6 C5 O1 116.96(10) C10 C5 O1 120.01(10) C5 C6 C7 118.26(11) C5 C6 H6 120.9 C7 C6 H6 120.9 C8 C7 C6 120.37(11) C8 C7 H7 119.8 C6 C7 H7 119.8 C7 C8 C9 120.11(11) C7 C8 H8 119.9 C9 C8 H8 119.9 C8 C9 C10 120.15(11) C8 C9 H9 119.9 C10 C9 H9 119.9 C5 C10 C9 118.25(11) C5 C10 H10 120.9 C9 C10 H10 120.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.3306(13) O1 C5 1.4180(13) N2 N3 1.3148(13) N2 C1 1.3431(13) N3 C4 1.3375(16) N5 C4 1.3240(15) N5 N6 1.3312(12) N6 C1 1.3266(14) C4 H4 0.9500 C5 C6 1.3701(16) C5 C10 1.3719(16) C6 C7 1.3869(17) C6 H6 0.9500 C7 C8 1.3781(18) C7 H7 0.9500 C8 C9 1.3833(17) C8 H8 0.9500 C9 C10 1.3884(16) C9 H9 0.9500 C10 H10 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 0.55(14) C4 N5 N6 C1 0.88(15) N5 N6 C1 O1 177.36(9) N5 N6 C1 N2 -3.82(16) C5 O1 C1 N6 2.33(15) C5 O1 C1 N2 -176.65(9) N3 N2 C1 N6 3.07(16) N3 N2 C1 O1 -178.04(9) N6 N5 C4 N3 2.64(18) N2 N3 C4 N5 -3.40(18) C1 O1 C5 C6 107.19(12) C1 O1 C5 C10 -77.38(13) C10 C5 C6 C7 0.63(17) O1 C5 C6 C7 175.92(10) C5 C6 C7 C8 -0.22(18) C6 C7 C8 C9 -0.21(18) C7 C8 C9 C10 0.26(18) C6 C5 C10 C9 -0.59(17) O1 C5 C10 C9 -175.73(10) C8 C9 C10 C5 0.13(18)